The Small Dick Club: SPH-THEMED STORIES

Chapters:

Part 1
Part 2
Part 3

*****

Part 1…

Wow. What a night. I’ll tell you one thing, though: I am exhausted. Even though I slept well on that tiny dorm-room cot last night, the experience was so overwhelming that my body is still recovering physically. And boy, I cannot wait to get home so I can take a long, peaceful, Saturday morning nap in my own bed.

But as I shift my car’s transmission from park to drive, I realize I can’t pull out of my parking spot because someone is blocking my path. It appears to be a young college student who’s just finished an early morning run, and now he’s cooling off by walking around in small circles in the middle of the street.

I’m a little annoyed, but as I’m about to tap my horn to alert him, I realize something. Holy shit, I know this boy! Or at least I think I do. He definitely looks familiar, and so I assume he must be from the dorm last night, right? Yeah, I’m pretty sure he is. Although, to be fair, everything about my previous 12 hours is kind of a blur.

It’s obviously not one of the four boys I ended up having sex with. Not only are those guys all still asleep, I assume, but I would definitely recognize them. It’s also not Brad, that nervous virgin from last night who couldn’t make up his mind as to whether he wanted to stay and partake in all of the carnal activities. Brad was a little bigger, kind of chubby, almost, and this kid is definitely on the smaller side, and not very tall either. He is quite sweaty, though!

Oh wait! I know who it is! It’s that boy who ran out of the room in a panic, before we even got to Brad’s dilemma. What was his name? It’s Jack, I think. Yeah, Jack. It’s definitely him!

Oh my god, I need to say hello! Even if it’s just for a second. This kid really is quite cute, though. He’s got curly, light brown hair, and while he’s super short, like probably only 5’6″ or so, that just makes him even more of a cutie. He has an adorable baby face, and while I really didn’t interact that much with him last night, I can safely say he has the youngest look of any of the boys I’ve seen here.

And shit, I just remembered the whole reason he left the dorm room last night! Supposedly, at least according to his friends, they thought he came in his pants while he was watching that Ethan boy finger me, before everything else went down. Holy fuck, I wonder if that’s actually what happened?!? I have to find out. Although I probably shouldn’t just come out and ask him, as I don’t want to embarrass the poor kid. Either way, I am definitely going to say hello.

I shift my car back into park and open the driver’s side door to get out. As I do, I see Jack get a little startled and apologetically put a hand up in my direction.

Jack (while looking bright red from his run and still panting a little): “Oh, I’m so sorry! I didn’t realize someone was there waiting to pull out.”

Me (standing up now and facing Jack): “It’s no problem at all, but hey…”

As I say this, I see on this boy’s face that, while he didn’t initially recognize me, it dawns on him now.

Jack (quietly): “Oh shit.”

Me (cheerfully): “I thought I recognized you! I know you from the dorm last night, right? When we were all hanging out in Chris and Ethan’s room?”

Jack looks quite stunned to be honest, and can only muster up a slight nod in response.

Me: “It’s Jack, right?”

Jack (after a brief pause): “Yeah… well, no. My name’s Jacob, but yeah, I was in the room.”

Shit. I’m an idiot. Yeah, it’s Jake, not Jack.

Me (quickly): “Oh shit, yeah, Jacob. Or Jake, right? Your friends were calling you both, I think? So sorry, I’m still a little hazy on some of the details of last night. It was kinda crazy, ha.”

I purposefully allude to all the fun Jake missed out on by bolting from the room, but the young, sweaty boy doesn’t seem to respond. In fact, I think he might still be in shock that he ran into me this morning.

Me (sticking my hand out): “I’m Becca. Nice to meet you, again.”

Jake (with a nervous laugh while shaking my hand): “Yeah, nice to meet you too, Becca.”

Me: “So, is it okay if I call you Jake? I kinda have a thing for nicknames, but I can also call you Jacob if you’d prefer I use your formal name, since you know, we don’t actually know each other that well.”

Oh god, I’m kind of rambling here. Why am I so nervous? Part of it must be how genuinely exhausted I am, and it’s making me borderline delirious. But I also think it’s because all I can think about is whether this sweet, baby-faced college boy actually did blow his load into his shorts last night because of me. I had all but forgotten this kid existed, and now I’m obsessed with finding out what happened!

Jake (no longer seeming as out of breath now): “Sure, you can call me Jake.”

Jake (kind of squinting as the early morning sun is getting brighter): “Jacob’s not even my real name, but it’s how I always introduce myself. My actual name is Jacobson, but it’s such an odd name that I never really use it.”

Me: “Oh, weird. Yeah, I’ve never heard of that as a first name before. Why did your parents choose that?”

Jake: “It was just my mom. I never knew my father.”

Me (surprised at this revelation for some reason): “Oh. Sorry to hear that.”

I wonder what the back story is there.

Jake (matter-of-factly): “Eh, it is what it is. But yeah, my mom claims she wanted to give me a distinguished first name, and for whatever reason, that’s what she came up with.”

Me (chuckling): “Okay, well, good for her, but I think I’ll stick with calling you Jake, though.”

Jake (starting to loosen up, it seems): “Sounds good. Yeah, she’s literally the only person on earth that calls me Jacobson.”

Jake (after taking a glance up at their dorm, and then back at me): “So you’re just leaving now? You spent the night here??”

Me (with a mischievous grin): “Yeah, I did. I hope that’s okay?”

Jake (still a little red in the face from his run): “Yeah, of course. No judgment here. Was just curious, is all.”

Me: “How about you? Why are you out running so early? What sport do you play?”

Jake (laughs): “Oh, I’m not an athlete like the rest of those guys. I’m just trying to get in shape for the first time in… well… basically my whole life? Ha.”

Me (genuinely surprised): “Oh wow, it seemed like everyone in that room last night was some sort of athlete. That’s great, you’re getting into shape though!”

Jake (holding out his left hand with fingers spread): “Yeah, I’ve found that having tiny hands can be quite the detriment on the athletic fields.”

Ha. His hands really are tiny! I instinctively put my right hand up against his left, and my fingers extend about a half inch beyond his. Holy shit. I’m used to having smaller hands than pretty much any other full-grown adult, so seeing anyone, let alone a male, with smaller hands than me is pretty crazy.

Even more noteworthy, though, is that this is the first instance of physical contact between the two of us, and as we press our palms together, one thing becomes abundantly clear in my mind.

I really, really want to fuck the shit out of this adorable, little curly-haired freshman boy. I also still want to find out if he actually came in his pants last night, but there’s no doubt that both things are true. Although I think they also might be related? Is it possible that part of the reason I actually want to fuck him is that he so innocently and pathetically couldn’t control himself last night?

Seriously, what the fuck is wrong with me? I just got laid by four different freshman boys, and even though their young sperm is still actively making their way through my fallopian tubes as I speak, I’ve already moved on and started fantasizing about my next 18-year-old conquest.

Becca, get a fucking grip! Ooh, that reminds me, though, I definitely need to stop at a pharmacy on my way home to pick up a Plan B pill. And it’s probably better to go to one around here, rather than my normal CVS by my house.

Anyhoo, as Jake and I continue to press our hands together, I look right into his eyes and give him a big smile. However, he then gets a little bit of a serious look on his face as he drops his hand back down.

Jake (much more quietly than he was speaking before): “So did you… Like, do stuff with everyone last night?”

Ha. Awesome. I love this question. It’s on like Donkey Kong.

Before answering, I briefly look up and down the street, confirming there’s not a soul in sight of the two of us, let alone in earshot. It’s not that surprising, considering it’s not even 6:30 yet on a Saturday morning.

Me (matter-of-factly, and speaking at a normal volume): “Yep. Well, not everyone stayed, but in the end, I think it was Chris, Ethan, Raj, and Dave. And we all had a great time, I’d like to think.”

Jake (with eyes wide open): “Oh wow.”

I raise my eyebrows and subtly nod to confirm that yep, you certainly missed out on some fun, young Jacob.

Jake: “What about Brad? Did he stick around?”

Me (with a hint of genuine sadness): “No, unfortunately not. I guess Brad’s a virgin? But anyway, he said the idea of losing his virginity in front of everyone was a little too intimidating. Which I can certainly understand.”

Jake: “Yeah, makes sense.”

I love that I’m recapping all of this with Jake right now.

Me: “Jake, can I ask you a question? And can you answer me honestly?”

Jake (after contemplating for a second): “Uh, sure.”

Me (a little more quietly, out of respect for the inquiry): “Are you a virgin, too?”

Did you think I was going to ask him if he actually came in his pants? Ha. In due time… 😛

Jake (after kind of bouncing his head back and forth in the air): “Uhhh… yeah, I am. Sorry. Is that bad?”

Uh, fuck no, it’s not! I was literally just having an epiphany walking out of this dorm 15 minutes ago, about how much of a fetish I seem to have for fucking virgin boys. It’s something I just never realized, but apparently now is all I want. I probably need to downplay my excitement over his lack of sexual experience at least a little, though, as I don’t want to come across as too creepy.

Me (reassuringly): “Oh no, not at all. It’s totally normal at your age.”

Jake: “Well… It’s not that normal.”

I then realize I probably do need to clarify one important detail, even though I’m 99% sure it’s fine.

Me: “Sorry if you already told me this last night, but you are 18, aren’t you?”

Jake: “Yeah, I turned 18 back in June.”

Me (with a joking scoff): “Yeah, so you’re barely 18. And to be honest, you look like you could be 15.”

Me (continuing): “Plenty of 18-year-olds are still virgins, and honestly, with how innocent you look, I think people would be more surprised if you weren’t a virgin. I swear it’s no big deal.”

Jake (looking appreciative): “Thanks.”

To be honest, it is a little surprising to hear that Jake is still a virgin, simply because of how cute he is. Maybe it’s a height thing? Or a confidence issue based on his height? Regardless, the fact that he’s inexperienced is such a huge fucking turn-on in my book.

Okay, back to the task at hand.

Me: “I mean, hey, look at your friend Brad. He’s still a virgin. And Ethan too, he’s all tall and handsome, and has that deep voice, and he was a virgin all the way until last night!”

Ha, in case it wasn’t clear, I just not so subtly pointed out the fact that Ethan and I definitely had sex last night. I did leave out the part about Ethan having a massive cock, though!

And then I smirk.

Jake: “Holy shit. Are you serious? Did you have sex with all four of them?”

Me (with a stern look of faux offense): “Are you judging me?”

Jake (apologetically): “Oh, I’m so sorry. I swear I wasn’t!”

Me (smiling now): “Relax, I’m just fucking with you. But yeah, I had sex with all four of them, and no joke, it was the most therapeutic night of my entire life.”

Jake looks a little shocked by my revelation. Maybe he thought we all just made out or fooled around or something? Or perhaps he assumed we did more than that, but hearing me say it so matter-of-factly surprised him?

Either way, I figure I’ve waited long enough, and now’s the time to finally ask the question that’s been on my mind since I stepped out of my car.

Me (while placing my hand on his shoulder): “So, no bullshit, did you really cum in your pants last night?”

Jake (startled by my question): “Whaaa??? Who told… how did… who told you that?!?”

Me (trying to be as sympathetic as possible, as I’m almost positive now, based on his reaction, that it’s true): “It’s okay. The guys said it when you left so quickly, but they were just being idiots.”

Jake (trailing off at the end): “Well, they don’t know what happened…”

Me (100% sure now): “Jake. Jake. Look at me.”

Jake, who had been looking down at the ground, returns to making eye contact with me.

Me (with both hands on his shoulders now): “I think it’s super flattering, and unbelievably sexy, that I turned you on enough for that to happen.”

Jake (quietly): “You do?”

Me (softly but emphatically): “Absolutely, I do.”

Me (a little louder now): “And I just have one more question for you.”

Jake (talking as close to me as we have this entire conversation): “What’s that?”

Me (whispering into his ear): “Would you want to have sex with me? Because I would absolutely love to be your first.”

As I pull back away from Jake’s ear, he doesn’t immediately answer me, which is a little surprising.

Jake (looking right into my eyes): “Do you know why I got so worked up last night, to the point where I had that happen?”

Me (extremely curious as to what he’s about to say): “No. Why?”

Jake: “My whole life, I’ve always fantasized that my first time would be with someone like you. Someone around your age.”

Me (with my eyes opened really wide): “Really?!?”

Jake (now seemingly in total control of this conversation somehow): “Yeah, really. I’ve never found girls my own age that attractive, and so seeing and knowing that Ethan was fingering you was just so overwhelming, that as soon as I accidentally brushed my crotch against the side of Chris’s desk in there, it just set me off.”

Me: “Oh my god, Jake. That is so fucking hot. Seriously.”

I still have so many questions, though.

Me (inquisitively): “So did you cum while you were in the room, finish into your underwear, and then leave because you had to clean yourself up?”

Jake (after taking a deep breath): “No, not exactly. I realized I was going to cum, and I couldn’t stop it. Panicked. Ran out of the room and then orgasmed into my khaki shorts while I was in the hallway. Thankfully, no one else was out there.”

Me (giggling): “That. Is. Awesome.”

Jake (laughing now, too): “Actually, it was a pretty awful orgasm. Probably the worst of my entire life.”

Me (speaking really fast): “Oh my god, Jake. I wanna fuck you so badly. Is that weird? Is that bad?”

Jake (finally answering my question): “I would love to have sex with you, Becca.”

Yes!!! Fuck yeah. I am so pumped. I can’t believe it took me this long to realize what an extreme fetish I have for young, innocent, virgin boys, because I am so irrationally excited right now. And just look at this kid! He’s the most adorable one yet! And he has a thing for older women?!? Talk about hitting the fucking jackpot.

Me: “I am so excited, but listen, is it okay if we don’t do it right now? Like maybe we can meet up later this week instead?”

I mean, I really need to clean up my act. Badly. And get some rest as well. The bottom line is, I’m sure we’d both appreciate it if I had some time to recover from everything that happened last night.

Jake (chuckling at my over-the-top exuberance): “Sure, yeah, whenever you want.”

Me (still so excited): “Okay, great.”

Me (sticking my hand out): “Do you have your phone on you?”

Jake (pulling the insides of his pockets out of his running shorts as if to prove he’s telling the truth): “Oh shit. Sorry, I don’t.”

Me (taking my iPhone out): “No biggie. Here, send yourself a text from my phone.”

I open my messages app, tap to create a new thread, then hand the phone to Jake.

Jake (so politely): “I’m just gonna text ‘Hey’ if that’s okay.”

Something about his sweet innocence just turns me on soooooo fucking much.

Me (while suggestively running my hand through his sweaty, curly hair): “That’s perfect.”

Jake (smiling bashfully at my initiation of physical contact): “Okay. All done. Here you go.”

And then, as Jake hands me back my iPhone, I take another glance up and down this sleepy college street. And once I confirm there’s still nobody else around, I lean in and give my new 18-year-old friend a quick, close-mouthed peck on the lips. This makes both of us smile.

Me (as I start slowly backing away to head to my car): “I can’t wait to continue this conversation when I get home!”

And with that, I get back into my car and finally pull out of my parking spot. As I depart, Jake gives me a slight wave, and once I’m finally out of sight, I take a long, deep breath and then follow it with an audible exhale. Suffice to say, I am both very excited and a little nervous about where this next adventure is going to take me.

Despite my preoccupied mind, I do remember to stop and pick up a Plan B pill on my way home. Once I arrive at my house, I take out my phone, put it on silent, and leave it on the counter so I won’t miss any texts from Jake. I’m so pathetic! But sure enough, shortly after noon, I hear a ping, and it’s a simple ‘Hi Becca’ message from Jacob. Yes! I am so pumped.

Our conversation starts innocently enough, but during this time, I start contemplating in my head about how, when, and where it would make sense for us to meet up to have sex. At first, I entertain the thought of heading back to campus and fucking young Jacob right there in his dorm room, but this is unappealing for several reasons.

First off, what if he has a roommate? Wouldn’t we have to worry about him interrupting us? And secondly, what if I ran into any of the other boys from last night? I feel like that would be kind of awkward, at least for me, it would be. And then finally, and this is so dumb, but those dorm beds they have are terrible! Last night was fantastic for so many reasons, but all of it would’ve been so much better had it taken place on a real bed with a real mattress. That’s not too much to ask, is it? So you add up all those reasons, and the dorm is definitely a no-go.

I briefly consider getting a hotel room for our little rendezvous, but it just seems unnecessarily complex and expensive. So in the end, that just leaves one option left, and it’s the clear choice—my bedroom.

Look, this bedroom has been ground zero for everything that was wrong with my relationship with my soon-to-be ex-husband, Greg. And I know he just moved out yesterday, but what better way to kick off this new chapter in my life than to bring someone else into the same bed where I’ve had so many depressing and unfulfilled nights. And who better to do it with than the exact opposite of the celibate 40-year-old asexual man I was married to, but instead a horny 18-year-old virgin who can’t even prevent himself from cumming.

Now, there is one downside to this option, but I don’t think it’s a big deal. If I invite Jake over here, then he’ll obviously know where I live. Initially, I didn’t want any of those boys from the dorm last night to know anything about my real identity, let alone my address. But perhaps Jake is respectful and mature enough that if I ask him to, he’ll be able to keep all of this a secret? It’s worth a shot.

So we discuss over text, and we agree on a plan. Jake is going to come over to my house this upcoming Friday night around 8 o’clock. It turns out that Jake has a car on campus, so he’ll be able to drive over here on his own. In theory, I could’ve picked him up at school and brought him back here, but that would’ve been kind of a pain.

I also ask him about keeping all of this a secret, and not only does he agree to be discreet, but he says that would actually be his preference as well. He said he doesn’t want any of his friends to know, simply because he’s so private. I can tell Jake’s being sincere here, which puts my mind completely at ease about our plan.

So I give him my address, and as I do, I apologize for how far away it is from campus. He actually responds that it’s sort of on the way (but not that close) to where his mom lives, so it’s not that big of a deal at all. Then he jokes that he’s already made that drive a couple of times this fall, but that he’s hoping this weekend will be much more rewarding than his typical trip home. I assure him that it will!

I love the innuendo, and I love that we’re all set for next weekend! We leave it at that, and over the next few days, there’s honestly not too much texting between the two of us. I’m okay with that, as I kind of like building a little mystery and suspense about what’s going to happen on Friday.

I’ll tell you one thing, though: this week sure seems to be dragging on forever! To be honest, it reminds me of how I felt when I was little, counting down the days until Christmas morning. Except in this case, I’m not going to be unwrapping presents under the tree, but instead I’m picturing myself unzipping Jake’s pants while I’m kneeling in front of him.

There’s also something appealing about the prospect of having some actual one-on-one alone time with Jake. As great as last weekend was, the fact that so many boys were involved made me feel like I didn’t truly connect with any of them. I think part of the issue was that, initially, I had the strongest connection with the soccer player Chris, but by the end, I was most attracted to Ethan, the engineer. And as a result, while I did leave feeling satisfied with the whole experience, I didn’t feel like I formed any meaningful bond with any of the boys individually.

I kind of hope that changes on Friday, when I can actually learn something intimate about young Jacob. The other thing I just can’t stop thinking about, and I know I’m a broken record on this, is the whole idea of Jake cumming in his pants! I love it, but it’s just so pathetic.

And let me clarify. I mean, I’m the one being pathetic here, by obsessing over this one event. I wasn’t trying to say that Jake’s uncontrollable orgasm last Friday night was pathetic! Although I do have to admit it was kind of. 😛

But the idea of Jake cumming in his pants, or shorts, or whatever, has continued to turn me on so much that it even led me to do something I very rarely do, look up porn on the internet! But it didn’t take me long to remember why I never seem to enjoy this experience. I tried to search some sites for anything related to boys cumming in their pants, but anything I found was so ridiculously fake-looking. It would be some well-hung 30-year-old porn star pretending to struggle with premature ejaculation, when obviously the whole thing was completely staged. It was very unsatisfying.

Another thing I find myself fixated on is Jake’s height, and just his small size in general, like how he has such tiny hands and feet. In fact, in some weird way, I find his small stature to be a turn-on??

I can safely say that small men don’t usually do it for me. Like, hypothetically, if I were going out on a date with a guy, there’s no way I would ever consider his being super short to be a turn-on or a positive in any way. Same thing with him having tiny features. I’m sorry if that’s harsh, and who knows, it might not be a total deal breaker for the guy, but it would definitely be one strike against any man like that as a potential suitor.

But maybe that’s just it? I’m definitely not looking at Jake as a potential suitor or as someone I would date. Instead, I’m obviously thinking about this as a one-time adventure. But even more notably, I’m not even thinking about young Jacob as a man. Now I know, legally, he’s 18 years old and officially an adult, but by pretty much any other standard, there’s no way Jake, looking like he does, would ever be considered a grown man.

And maybe it’s because I’m already accepting this fact, that he’s a very, very, young adult, that his small stature is actually a positive, somehow? It’s as if his shortness just makes him even cuter in my eyes. I think it also makes him seem even more naive and innocent, too. Which I’ve already accepted are all huge turn-ons for me now.

Now, even with how aroused I’ve been thinking about Jake, one thing I haven’t done this week, and this is totally on purpose, is orgasm. I’ve spent some time touching myself, as I always do, but over the past few days I’ve made a point of stopping before I get to the point of cumming. I’m doing this because I want to try and build up as much as possible for when Jake gets here, and I think it’s working.

I say that because, regardless of whether I’ve been at home or even at work, this whole week I’ve had this ever-present horniness that seems to permeate all of my thoughts, no matter what else I’m supposed to be doing. I just can’t stop thinking about Jake, his other friends from the dorm, or just sex in general. It’s literally all I can think about. I’m sure it’s related to the fact that I can’t remember the last time I ever went a whole week without bringing myself to orgasm, so I think my body is suffering through some sort of withdrawal here.

Now, even though I’ve been denying myself pleasure, I would assume Jacob has been masturbating like normal this week. Although maybe he’s been thinking about me when he does it, though? That would be nice! I’ve also heard that guys will purposefully jack off right before a known sexual encounter, just to help them last longer. It seems like this strategy would definitely make sense for Jake, given what happened between him and the corner of Chris’s desk last weekend. 😛

I’m not going to lie, though, I hope he’s reigning in his masturbation like I am. I would love for him to come into Friday night with a massive buildup of his own, and then have the same ‘issue’ as last time, except in this instance, I’d get to see it happen firsthand. I’d be so curious to see his facial expression once he passes the point of no return, and then to feel his body coming when it wasn’t supposed to, followed by the mess he makes inside of whatever he was wearing. It’s so hot to think about!

I mean, if he did cum in his pants, I’d assume that wouldn’t be the end of things, and he’d be able to rally for a second go around soon after, right? That’s what being 18 years old is all about! If so, it seems like a total win-win. I would get to watch Jake cum in his pants, which I’ve been obsessing over this whole week. And then afterwards, when we did have sex, he’d be able to last a lot longer than he otherwise would’ve! Ha. A girl can dream, right?

Okay, the night is finally here!

After I get home from work, I grab a small, quick bite to eat and then hop in the shower. I give myself a fresh shave, so I’m nicely clean and smooth all over, but mainly down there, and then I actually take the time to do myself up right. Last weekend, I didn’t really get all dolled up when I went to the dorm, but that was on purpose because I was acting like the whole night was supposed to be a chance encounter. Tonight, I’m not going overboard or anything, but I am spending more time on my hair and makeup than I usually would. I want to look sexy for this boy!

It’s 7:42 pm, and I’m about to head downstairs to wait for Jake when I hear my doorbell. Is that him? Is he early?!?

I turn off the lights in my bathroom, head down my front staircase, and yep, I see him through the window of our front door. And my god, he looks fucking adorable!

Jake is standing there on my porch, and he’s looking around from side to side as if he’s nervous. He’s wearing a button-down shirt tucked into his jeans, his hair looks extra fluffy, and he appears freshly shaved. He looks like a teenager who’s on his way to church or something. I love it.

I quickly open the front door and greet him with a huge smile.

Me (enthusiastically): “I’m so glad you came!”

Jake looks happy to see me, but yep, he looks super nervous.

Me (stepping aside): “Come in…”

Jake (very timidly): “Thanks. Sorry, Becca, I know I’m a little early.”

I usher the shy, sweet boy in, and then I quickly close the door behind him. I had instructed Jake to park in my driveway because he could get a ticket if he parked on the street overnight. Not to be too presumptuous, but I am kind of hoping for a sleepover. 😛

But anyway, Jake followed my instructions, as I can see his Kia Soul sitting in my driveway just in front of my attached garage. It looks to be a pretty old model, and it’s kind of beat up, but hey, a car’s a car, right?

Me (as Jake politely takes off his shoes without being asked): “No problem with the timing. I was just finishing getting ready. How was the drive?”

Jake: “Oh, it was good. No issues. Sorry about my car.”

Me (not sure what he’s referring to): “What do you mean?”

Jake (still seeming very reserved right now): “Oh, just that it’s so old and that it probably looks out of place in front of your house and this nice neighborhood you live in.”

Ironically, our town isn’t really that nice or upscale compared to some of the other areas nearby.

Me (placing my hand on Jake’s shoulder): “Oh, don’t worry about it at all. It got you here, and that’s all that matters!”

Jake (smiling): “Thanks. The car was a present from my mom when I graduated from high school. I know it doesn’t look very nice, and it has a ton of miles on it, but it was kind of a big deal for her to get it for me.”

I’m starting to think that Jake and his family, which sounds like it’s just him and his mother, don’t have much money. This is obviously totally fine, but I’m guessing he might be a little self-conscious about it, considering all the rich kids he goes to school with. I hope he doesn’t think that I would ever care about that!

Me (dropping my hand from his shoulder and taking Jake’s hand in mine): “Can I get you something to drink? Water? Soda? A beer?”

I know young Jacob isn’t of legal drinking age yet, but I figure a beer or two might help calm his nerves.

Jake (quietly): “I’m good. But thanks.”

Hmm. This is all feeling a little awkward. I had initially assumed he was just nervous, but now I’m worried he’s actually having second thoughts about being here. I sure hope it’s the former.

I figure there are two ways to proceed. I could either invite Jake to have a seat in my living room, where the two of us could just chat a little. Hopefully, he would relax, and I could make sure he was completely comfortable before we moved on to anything physical. Or I could take the more direct approach and simply invite him upstairs so we can dive right into whatever’s going to happen. You know, rip that bandaid off! Surprise, surprise, I think I’m going to go the second route.

Me (looking up the stairs while still holding Jake’s hand): “What do you say, can I take you up to my bedroom?”

Jake doesn’t say a word, but simply nods in agreement. Alright, that’s good enough for me. Let’s do this!

I start climbing the stairs, holding on to Jacob’s hand as I ascend. The act of me leading this young boy up to my bedroom is quite poetic. Here Jake is, walking up the stairs under his own power, but I’m also pulling him up, helping him to go just a little bit faster. It’s the perfect metaphor for how I know Jake is excited to have sex and finally lose his virginity, but I’m pretty sure I want it to happen even more than he does.

Once we get to the top of the stairs, I lead him into my bedroom, still holding his hand. We stop for a second in front of my bed, and I turn to face him and take hold of his other hand as well.

Jake (while looking around): “Your bedroom is really nice.”

Me (smiling): “Thanks.”

Jake (now looking right at me): “And sorry I didn’t say it before, but you look really pretty tonight.”

Fuck. The way he just said that sounded so awesomely sincere, like there wasn’t the slightest hint of it being some line or something he was saying because he thought he was supposed to. His delivery makes me feel beautiful, and I love it.

For context, I’m wearing my best pair of jeans and a silk lavender sleeveless V-neck. I have on one of my favorite necklaces, a silver pendant with a ruby-like rhinestone I got in China many years ago, along with some simple pearl earrings. My black bra is just peeking out the sides of my top, and I’m wearing a black thong underneath my jeans to match.

As I mentioned before, Jake is wearing a nice, light-green button-down shirt with a baby-blue checkered pattern. He has it neatly tucked into his pair of jeans, sans belt, and a pair of plain white socks covering his feet.

Me (in response to his telling me how pretty I look): “Awww, you saying that makes me feel so good.”

Jake smiles, and I just can’t help myself. I move in somewhat aggressively for a kiss.

Initially, it feels like Jacob is a little startled by my advance, as he instinctively retreats a few inches back. But after I make contact and we hold our kiss, I feel him actually pressing forward into me a little, too.

Me (after our lips separate with an audible smack): “Can I ask you something personal?”

Jake (starting to seem a little less nervous now, compared to when he was downstairs): “Uhh, sure?”

I know this is an invasive question, but I just really want to know.

Me (matter-of-factly): “Did you masturbate tonight before coming over?”

Jake (seemingly caught off guard by my question): “Uhhhh, noooo? Was I supposed to??”

Ha, I love his answer. He’s too cute. And I can tell from his delivery that he’s definitely telling the truth.

Me (chuckling): “No, not at all. I was just curious because I heard that some guys do that. That’s all.”

Jake (quietly): “Oh, okay. Yeah, no, I didn’t.”

Me: “So when was the last time you did do that then? Masturbate that is.”

Jake (while raising his eyebrows to think): “Ohh, geez. Ummm. I guess Tuesday, I think? Yeah, Tuesday afternoon.”

Fuck, I love this answer as well. Three full days without cumming? That’s an eternity for an 18-year-old boy! He must be primed and ready to pop, one would think.

Me (curiously): “Why have you not done it since then??”

Jake: “Oh… no reason, really, just my roommate mainly. He likes never leaves the room, so it makes it kinda tough to, I guess.”

Hmmm. That seems like a valid reason. That also kind of sucks for Jake to have so little alone time.

Alright, I know this is selfish and manipulative, but I have to do it. I just can’t help myself! I’m going to do a little experiment here and see whether I can get Jake to cum in his pants again. Right here, right now. Please don’t think less of me!

Me (pulling Jake’s body close to mine): “So you were serious when you said you have a thing for older women?”

Jake (nodding slowly at first, then verbally responding): “Yeah, I think so.”

I give Jake another quick kiss, as we continue to stand in the middle of my bedroom, fully clothed.

Me: “That works out well, because to be honest, I’m starting to realize I have a huge thing for teenage boys.”

There we go. I think my plan is starting to work.

Jake (with the amplitude of his breathing starting to increase): “You do?”

Now I’m the one who simply nods in response.

Jake’s inhaling and exhaling continues to get more and more pronounced, but I don’t have any intention of slowing things down. I reach behind my cute, little freshman friend’s waist and use both hands to pull his body into mine.

Me (almost whispering now): “It turns me on so much that you’re a virgin. And I’m sure I would remember it forever, if you would let me be your first.”

And as I say this, I give his adorable little butt a tight squeeze and really press our pelvises together. After holding them against each other for a few seconds, I slowly start moving my hips to grind my crotch against his. I figure this has to feel good to Jake, as it does to me immediately, but it seems to trigger almost a negative response from him. Right after I start this rubbing motion, Jake immediately pulls his midsection back, creating some space between our two bodies.

Jake (a little panicky): “Oh, sorry, that was… I didn’t mean to… that was just a little intense.”

It’s working!! There’s no doubt he’s already getting worried about cumming—time to finish the job.

Now that there’s a little room, I reach down and take Jake’s right hand and slowly move it towards my crotch. Next, I turn his palm so his fingers are vertically oriented, and then I slide his four outstretched fingers right into the slot at the top of my thighs. When I do this, I see Jacob’s jaw literally drop.

Me (as I pull up slightly on Jake’s hand, applying some pressure to my vagina through my jeans): “Oooooh, that feels soooooo good.”

Jake doesn’t say a word but is staring at me with eyes wide open. I then take my free hand and use it to pull Jake’s body back into mine, pinning his hand between our two crotches.

Me (whispering into Jake’s ear again): “Your hand feels soooooo good against my pussy.”

Jake lets out an awkward little grunt and gives off a quick full-body shudder. I think it might be happening?!?

Me (still whispering): “It’s soooo warm.”

Yep. It’s happening. I can’t believe how easy this was!!

Jake abruptly pulls his hand out from between my legs and forcefully takes hold of both of my shoulders. He then lowers his head and buries his face into my clavicle.

Jake (after a pained grunt): “Sorry!! Oh shit. Fuck!”

Oh my god, he’s jizzing in his pants right now. This is so awesome!

Despite his head resting on my collarbone, Jake has pulled his hips back away from my body, as if he’s purposefully trying to shield me from any potential mess.

The truth is, I don’t want or need him to shield me from anything, so I reach down and press my hand against the bulge of his jeans and start rubbing. Even though the denim is a pretty thick material, I want to try to make his orgasm feel as good as possible. I also figure I’ll try to help him cum as much as he can, too, as the bigger the mess, the sexier it’ll be.

As I’m massaging his young cock through his pants, Jake starts panting.

Jake (now pumping his hips rhythmically into the palm of my hand as he grunts): “Oh god… oh god… oh god…”

Me (reassuringly): “Shhhhhh… it’s okay… just cum… just cum as much as you want…”

Finally, Jake’s orgasm subsides, and he quiets down. My hand remains on his crotch, and then for the first time, I feel a little wetness making its way through the thick fabric of his jeans.

Me (pulling my own face back so we can make eye contact again): “You okay? You feel better?”

Jake (looking at me with the sweetest puppy dog eyes): “I’m so sorry. I’m soooo, so sorry.”

Oh my god, you sweet boy. Don’t be sorry! I wanted you to blow your load into your pants so fucking badly. In fact, I was doing everything I could to make it happen! There is absolutely no need to apologize, because I loved watching every second of your gooey, premature orgasm.

Me (clearly hiding my true motives here): “It’s okay. It could happen to anyone.”

I know, I know… I’m going to hell.

Jake (now seeming a little somber): “You probably want me to go, huh?”

Shit. That’s not the reaction I was looking for. Time to correct this before we get too far off course.

Me (emphatically): “Oh my gosh, no! I definitely want you to stay. In fact, I’m even more turned on now than I was a few minutes ago.”

Jake (looking very skeptical): “You are?”

Me: “Absolutely. In fact, how about we survey the damage in your underwear, and maybe I can help you rinse off in the shower? Get you all cleaned up?”

Jake (looking a little more at ease): “Okay. That sounds nice.”

This is perfect. Jake can take a shower and get all squeaky clean and smelling good. And a rinse off should also give his pecker enough time to recover and start getting ready for round two.

So I take my barely legal friend by the hand and lead him into the master bathroom, just past the combination walk-in closet and washer/dryer that’s connected to my bedroom. Once we get in there, I turn the shower on right away because I know it can take a while for the water to heat up.

Me (walking back towards Jake): “Can I take a look at the mess you made in your pants? I’m curious to see it.”

Jake (looking down): “Okay. Sure?”

I grab the two flaps of Jake’s jeans and pop the button open. And as I pull them apart to force his zipper down, I can immediate see the fallout from all the sperm he just expelled.

Jake is wearing a pair of light gray boxer briefs, which I’m pretty sure are the same brand I buy for my son at Sam’s Club. But on the front of them, there’s a vast, dark, wet spot that’s partially hidden behind the tucked-in front flaps of his button-down shirt. It’s worth noting that one of his shirt flaps was not immune to the damage, as it’s got a prominent wet cum spot on it now.

As I see all this, I start unbuttoning Jake’s shirt, and since he’s not wearing anything underneath it, as soon as I remove his long-sleeved collared shirt and toss it onto my tiled bathroom floor, my adorable little boy toy is now topless. And I have to say, he has a really cute chest and upper body.

Next, I start taking off his jeans, which are somewhat tight but not too hard to get off. I toss those aside, then remove Jake’s socks. At this point, I stand back up and admire the sight of what’s in front of me. There’s a teenage boy, still looking completely shocked and nervous, standing in my bathroom, wearing nothing but a pair of cum-soaked boxers. It’s glorious.

I’m about to reach down and remove Jacob’s last remaining article of clothing when he says something unexpected.

Jake (as he turns his head towards the tub that’s across from my shower): “Do you think you could give me a bath instead?”

Hmmm. What an interesting request. Not only the part about taking a bath instead of a shower, but the way he phrased it. Me bath him? I’m definitely OK with whatever makes him comfortable, though.

Me (agreeably): “Sure. No problem.”

I walk over and crank the tub’s faucet on hot before heading over to stop the shower. When I come back, I can feel the water is plenty warm enough, so I pull the rod up to close the drain, and the bathtub starts filling up. I then return my attention to young Jacob.

I don’t bother asking permission, but instead I simply pull his waistband out and peek inside his semen-drenched pair of underwear. And as I do, I get my first glimpse of that tired little guy that just exploded all over the place. And when I say little, I mean it!

Now granted, his penis is clearly soft and flaccid right now after cumming, so I don’t want to assume too much based on its current size, but it’s notable how small it appears. It’s also noteworthy how much cum is covering the entire contents of his undergarment. Holy shit, there’s visible jizz everywhere! There’s cum stretched across the open space where his cock and balls are, as well as all soaked into the interior fabric of the boxer briefs themselves.

I certainly don’t let that deter me, though, as I quickly pull down his underwear, trying my best not to get semen all over his legs as I remove them. Now that he’s completely naked, he looks even more innocent than before, especially considering how his tiny limp penis is barely big enough to poke out from behind his dark brown pubic hair.

I check the bath’s temperature, and it seems reasonable, so I take Jake’s hand and lead him into the tub. And as he sits down into the couple of inches of water that’s filled up so far, he looks back up to me as if to ask, what’s next?

I have to say, there’s something really hot about how Jake is sitting here totally nude in my bathtub, while I’m still completely clothed. There’s a clear power dynamic at play, but I also think it’s because I just love the sight of a naked 18-year-old boy!

Now I know last weekend Jake claimed he was out running because he wanted to get into shape for the first time, but I have to say, he already looks pretty damn fit to me! He’s quite skinny, but what is there has some decent muscle tone, so both his upper and lower bodies look very lovely. There’s no doubt he is very short, though, and for whatever reason, it’s even more apparent now that he’s naked.

I’ll tell you one thing, though. He has one of the cutest outie belly buttons I’ve ever seen! And while he seems to be rocking a full man bush, and of course, he has hair in his armpits, otherwise, it’s notable how not hairy his chest is. It’s basically smooth. In fact, his whole midsection is pretty hairless, other than his pubes, of course.

Speaking of his pubes, one thing his prominent bush does do is highlight just how small his dick is. Again, I’ll definitely give him the benefit of the doubt, because I know boys talk all the time about how some of them are showers, and others are growers. But his little pecker looks so small hidden behind all that hair, that it’s tough to imagine it growing into a full-sized cock. But I’ll tell you one thing, I should know soon enough!

Now, as good as Jake looks naked, I definitely feel the opposite about myself. At my age, despite being in pretty good shape, I’m still self-conscious about my nude body as I approach my 40s. Suffice to say, I have no issue with the fact that Jake is buck-ass naked, and I still get to keep my clothes on.

Jake is now simply sitting in the tub, and once the water level rises to his waist, I turn off the faucet. I figure I don’t want the bathtub to fill up too much, as it obstructs my view! After shutting off the water, I head over to the shower and grab a loofah and some body wash. I mean, he did say he wanted me to bathe him, right?

So I kneel next to the tub, squirt a healthy amount of liquid soap into the loofah, and then lather it all up with my hands. Once it’s good and soapy, I begin to wash Jacob’s very sexy body.

I start with his shoulders and upper back, then move to his chest. He’s looking at me sweetly as I do this, mostly keeping his eyes on me, but occasionally looking down to see what I’m washing. Eventually, I get to his abs, and then without trying to make a big deal about it, I reach down and scrub his genital region. His crotch is basically right where the water level is, so it splashes around quite a bit as I scrub his junk. Considering that’s where all of his cum was, though, I try to do a good job of legitimately washing it. Finally, I reach down and give each of his legs a soapy once-over.

Jake (looking so sweetly): “Thanks for doing this. It’s really nice.”

Me (enjoying this a surprising amount as well): “Yeah, no problem. It’s my pleasure.”

And then I smile.

As I’m taking stock of this whole scene, I realize all of Jake’s newly dirty clothes are still strewn about my bathroom floor. I figure I should probably offer to do something about them, right?

Me: “Hey, do you want me to throw your underwear and the rest of your clothes into the wash? I don’t think they’re really wearable in the state they’re in.”

I chuckle, thinking about how they’re all soaked with 18-year-old boy cum.

Jake (sitting up in the tub to take a look at the floor): “Oh, that’s very nice of you, but it’s okay. I’ll be fine.”

I realize that in addition to being a nice gesture, my washing Jake’s clothes also kind of prevents him from leaving, at least for an hour or two, right?

Me (walking over to gather them): “Nonsense. My washing machine is right here, so I’ll just do a quick load, and then they’ll be clean.”

Jake (seeming genuinely appreciative): “Thanks.”

As I begin to prepare the small load of laundry, I see Jake grab the body wash and re-soap the loofah I had been using on him. Next, I see him lift the right side of his body completely out of the water and begin scrubbing up and down his ass crack. Now, normally, I would probably take great offense to someone using my personal sponge to wash their butt crack, but I figure he’s cute enough that I’ll let this one infraction slide. 😛

Once he’s finished washing himself, I figure I should ask him about the button-down shirt he was wearing.

Me (calling back to Jake): “Hey, are you ok with me throwing your shirt into the wash as well? Or do you only dry clean it?”

Jake (looking totally perplexed): “Dry clean?”

Ha. With that reaction, I’m guessing he’s never had anything dry-cleaned in his life.

Me (smiling): “Nevermind. I’ll include it with the rest.”

I start the small load of laundry and head back to the tub.

Me (crouching back down): “How’s the bath going? Did you remember to wash all of your hard-to-reach places?”

I say that second part as a joke, both alluding to his butt washing, and also phrasing it like something a mother might say to her son. But then it hits me that if I’m trying to have sex with this college boy, which I obviously am, then maybe mom jokes aren’t the best idea.

Me (quickly apologizing): “Sorry if I’m giving off major mom vibes here. I realize that probably isn’t what you want to be envisioning.”

And then I give off another small laugh. But thankfully, Jake smiles and chuckles as well, as if to indicate it’s all good.

Jake (still beaming): “Don’t worry about it. Everything is perfect right now.”

That’s good. I’m really am glad he’s having a good time, as am I. He seems like such a sweet kid, and it also seems like he hasn’t had the easiest life so far, at least from the limited amount he’s told me about his childhood.

I figure if he was fine with my motherly joke a second ago, it’s probably not a big deal if I ask him a little bit about his home life growing up?

Me (trying to get a better picture here): “So has it always just been you and your mom living at home? Do you have any siblings or other family?”

Jake: “Yeah, just my mom and me. But we’ve survived this long. And now I’m in college, so I think we’re doing something right.”

Me: “Yeah, that’s really great.”

Jake (perking up with pride): “I’m actually the first person in my family to ever go to college. But it’s all thanks to my mom. She sacrificed everything, basically.”

It’s really sweet how positively he speaks about his mother. First, it was about the car she got him as a present, and now it’s about the sacrifices she made so he could go to college.

Me (liking this kid more and more every minute that passes): “That’s so awesome. And so cool for your mom. I’m sure she’s so proud.”

Jake smiles.

Me (still curious): “Sorry if this is too personal, and you don’t have to answer. But do you have any relationship at all with your dad?”

Jake (seeming totally fine to answer the question): “Nah. Never met him. And to be honest, I don’t really have any desire to.”

I nod in sympathy.

Jake: “From what I do know, he’s not a very good person. And so meeting him would probably be a bad idea, and I don’t know if I’d be able to control myself. Like, I don’t know what I’d say or what I’d do, but it probably wouldn’t be good.”

Me (feeling bad now for having brought this topic up): “Oh, I’m so sorry, Jake. I didn’t mean to drum up any painful memories.”

Jake (still seeming totally relaxed as he splashes around in the tub): “Oh, it’s okay. It really is.”

Me (placing my arm on his shoulder): “It seems like you’re pretty protective of your mom. That’s really sweet.”

Jake (chuckles): “Yeah, I am. But only because she deserves somebody to take care of her.”

Me (giving in to my curiosity): “So, what would happen when your mom would bring someone home that she was dating? Would you get all over-protective and make sure the guy was good enough for her?”

Jake (looking up at me from the tub): “You know… for whatever reason, that’s never happened. She never really dated anyone, ever, that I can remember.”

Now I’m worried about how lonely this poor woman must be! She raised this kid during what I assume are her prime adult years, and she didn’t even have time for her own relationships? That’s so sad!

Me (showing sympathy): “Aw, that’s too bad.”

Me (trying to make light of the situation): “Here I am, having been separated from my husband for only a week, and I’m already worried about not finding someone!”

Jake (smiles at me): “You’re so pretty, I’m sure you won’t have any problem at all.”

What a sweetie!

Me (after grabbing the loofah from Jake and giving his chest a sensual little scrub): “Well, I know I’m looking forward to getting some of my needs and desires fulfilled tonight, that’s for sure.”

I then raise my eyebrows suggestively and smile, but instead of grinning back as I would’ve expected, Jacob gets a serious look on his face.

Jake (after a few moments pass): “Can I tell you something extremely personal?”

Oh my god, yes. A thousand times, yes. I’m so curious to know what he’s about to say!!

Me (restraining myself): “Of course. If you want to, that is. But yeah, you can tell me anything.”

Jake (clearly really nervous all of the sudden): “I used to… I mean… my mom never had boyfriends… but she would masturbate a lot.”

Oh really?!? This is interesting, and pretty fucking weird that he knows this, but definitely interesting.

Jake (continuing): “I know that… because I… because I would spy on her when she did it.”

Woah. So many fucking questions. Where do I begin??? Be reasonable, Becca. This obviously is a very personal thing for this boy to be sharing, let alone answering questions about.

Me (with a subdued tone): “Wow. That’s interesting. So how exactly did you spy on her?”

My heart is racing now for whatever reason.

Jake: “The very first time, I didn’t know what was going on. The walls in our house are pretty thin, and I heard a weird buzzing noise. I know now that it was her vibrator, but at the time, I had no clue. So I went into her room to tell her I heard something.”

Me (captivated by this tale): “Okay… go on…”

Jake: “She was in there under the covers, but I clearly had startled her. When I told her about the weird noise, she apologized and told me it was nothing to worry about and that I should go back to bed.”

Ha. This actually sounds quite believable. Too funny.

Jake: “So that was the first time. But then I would hear it again and again, but instead of going in and asking her, I would stand outside her room, and since her door was always left open a crack at night, I could see in. And the way her room is, I could actually see her bed through the crack.”

Jake (after pausing and locking eyes with me): “And so I would watch her.”

Wow. This is nuts. First off, there’s no way she didn’t know that he was spying on her, right? I wonder what the story with that is. And secondly, what in the world was running through his mind while he was watching her?!?

Me (totally fascinated by this for some reason): “Did you like watching her? Or did it make you uncomfortable to see your mom do that?”

Jake: “No, I liked watching her.”

Jake (now with a pained look of guilt on his face): “I liked watching her a lot.”

Oh, this sweet boy. Now I feel kind of bad that he feels so bad about this.

Jake (super quietly): “It’s so weird. I know.”

Yeah, it is kind of weird. It definitely is. But it’s still fascinating. Wait a second… is Jake’s attraction to his own mom actually turning me on right now?? Oh my god, it is. Fuck, this must be my horny brain that hasn’t orgasmed for seven straight days taking over right now, because this doesn’t seem like the sort of thing that would typically do it for me. What have I become?!

Me (trying to rein in my pervertedness to show some sympathy): “No, it’s not weird. I’m sure you were just curious.”

I know I’m pathetic, but I need to know more.

Me: “So would you get excited whenever you’d be in bed and you’d first hear that buzzing noise coming from your mom’s room?”

Jake: “Yeah. And whenever she’d go for long stretches without, I’d get kinda down. Like bummed out that she wasn’t doing that.”

Me: “So would you think about her doing that even on nights when she wasn’t?”

Jake: “Yeah, I would.”

Jake (trailing off): “I would fantasize about her a lot…”

Interestingly, he used that word. I had been thinking it, but I didn’t want to say it.

Me (I’m so shameless): “What would you fantasize about with her?”

Jake: “I’d think about how much I loved watching her, and how I wished I could get to see her up close when she was doing that. And I would also think about touching her and what that would be like. But most of all, I fantasize about making her feel good. Making her happy.”

My god. This is all so much to take in, and I’m struggling to process everything he just said. And did he just say fantasize, like in the present tense? Holy shit. This is one hell of a plot twist that just unfolded here. I mean, a couple of minutes ago, I was thinking how sweet it is that he feels so highly of his mother. But wow, I just didn’t realize how deep those feelings actually were!

And holy fuck! I just remembered what Jake said last weekend when we were chatting after his early morning run. He said something to the effect that he had always fantasized about his first time being with someone around my age. Here I was thinking that he had a thing for older women, but instead, maybe it’s just one specific woman he has in mind? His own mother?!?

Me: “How old is your mom, Jake?”

Jake: “She turned 40 this year.”

Yep, that’s me. Holy shit. This all makes sense now. And the bath! The way he asked me to bathe him instead of showering off as I had suggested?!? That’s such a motherly thing to do! Holy fucking shit.

I mean, maybe he doesn’t even realize what he’s doing, and this is all on a subconscious level or something. On the other hand, perhaps he knows exactly what he’s doing. But either way, there’s no doubt in my mind that he’s using me to live out some long-held fantasy of his involving his own mother, at least on some level.

Am I okay with this? God, I think I am, and it’s so fucking weird. But I’m so that fucking turned on right now. I guess this is what I get after two decades of basically being celibate! My sex life goes from absolute nada, to fucking four college boys in their dorm last weekend, to this weekend potentially taking the virginity of this adorable boy who happens to have a crush on his own mom.

Yep. I am nuts. But I don’t care. Okay fuck it, if we’re going to do this, we’re going to do it for real. I can’t believe I’m about to propose this, but here goes nothing…

Me (feeling like the nervous one now): “Is it okay… sorry, let me rephrase… Jacob, would you like… for tonight… for me to pretend to be your mom? Like a roleplay?”

My proposition definitely gets Jake’s attention, and he looks up at me with a kind of confused expression.

Fuck. I shouldn’t have asked that. That was too far over the line, as I’m sure he holds his mom in such high regard that my suggestion is probably insulting. I’ve definitely offended him by asking. Look at his face! Shit.

Jake (after what feels like forever): “You would do that for me??”

Holy shit. Scratch that. He’s definitely not offended.

Me (with my heart beating so intensely): “Yeah, I think so. I think it would be fun. Would it turn you on?”

Jake (quietly): “Oh my god, it would.”

Holy shit. This is awesome. And then I remember one other key detail from our chat last Saturday.

But before revealing that, I stand up and head over to the shower to grab a bottle of shampoo. And as I come back and kneel next to Jake in the bathtub, I squirt a generous amount of the L’Oréal into my hand.

Jake watches intently to see what I’m about to do.

Me (as I deposit my palmful of shampoo into his cute, curly hair): “Okay, Jacobson, we need to wash your hair before we can get you outta the tub.”

Jake looks up at me with such adoration, clearly responding to the fact that I used his full name, which he had told me a week ago that only his mother called him.

And then he lies back, closes his eyes, and exhales, while I begin to lather up his short, light brown, adorable curls.

Jake (with a massive sense of satisfaction and relief): “Oh my god, Mom. This feels soooo good.”

Wow. It’s on. I called him Jacobson, and he called me Mom. I have no idea how this is going to unfold, but it’s going to be really fucking interesting.

I keep on massaging Jake’s scalp with my shampoo-covered hands, doing my best to suds up every last strand of hair. And as I’m doing this, I see his breathing start to pick up. His chest is noticeably expanding and contracting, and I can audibly hear his exhales again. His eyes are still closed, and it seems like he’s in heaven.

Jake (repeating himself): “Oh, Mom, this feels soooooo amazing.”

And then I see it.

Between the body wash we used before and the newly added shampoo, there’s now a decent amount of soapy bubbles sitting on top of the water, still right at Jake’s midsection. But out of this film of cleanliness, I see Jacob’s innocent little, 18-year-old penis start to rise. It happens slowly at first, but then it keeps on growing until it’s all the way out of the water.

Holy shit, his cock looks so good. And remember, before, how I thought it looked like he had a small penis, but I didn’t know for sure because it was totally flaccid? Well, he has a full-on boner right now, and yep, it’s not very big. But I don’t care one bit. It’s the cutest, little rock-hard pecker I’ve ever seen.

It’s fully extended and appears to be only about 3.5 inches long. And while his shaft is also tiny, like not very thick, he has the biggest, plumpest, bright red mushroom tip on the end of it, that appears to be totally engorged with blood right now.

Fuck. That penis looks so goddamn appealing sticking out of that bathwater. It’s so wet, clean, and ready for attention. I want it in my hands. I like it in my pussy. But perhaps most of all, I want it in my fucking mouth. And trust me, that’s a weird thing for me to crave.

I’ve always been happy to give someone a blow job, especially if it’s in return for their going down on me, but I can’t ever remember actually fantasizing about sucking someone’s cock before. I’ve never really wanted or needed to do that to someone, at least never this badly.

And now, as I stare at Jake’s soapy, wet, rock-hard, little lollipop penis, all I can think about is engulfing the entire length of it into my mouth. I want to feel his pubes against my gums, and that giant mushroom head in the back of my throat. And most of all, I want to feel him explode into my mouth, so I can swallow every last drop of cum this adorable 18-year-old boy has to offer.

But perhaps most notably of all, I’m even willing to pretend to be this kid’s mom, if that’s what it takes. In fact, I’ll do anything this boy wants. I just need that fucking cock, in this fucking mouth, right the fuck now.

*****

Part 2…

If my friends could see me now, they would lose their fucking minds. Like seriously, they’d probably try to check me into a mental institution, or at the very least start planning an intervention on my behalf, ha.

And honestly, I probably wouldn’t blame them for reacting that way! I mean, last weekend was crazy enough, but it was literally my first night being separated from my husband, Greg. So I think it was totally natural and even somewhat expected that I would act out and do something crazy. Now granted, fucking four freshman college boys in their dorm room is obviously pretty extreme, but I think you could easily chalk that adventure up to being some sort of a one-off coming-out party. You know, like I was just making up for lost time.

But this situation I’m in right now? Whoa, this is a lot harder to explain, and I think a lot more embarrassing to admit to, if, for some reason, my friends were ever to find out about it. Not only am I seducing another innocent 18-year-old boy, but this time it’s in my own house, and of course, he’s also a virgin, and oh, by the way, we’re going to roleplay where I pretend to be his fucking mom!

I know it’s bad, and I know it’s so weird. But I’m going to let you in on a secret. I don’t care! I’m just so turned on right now, and I’m sure part of the reason why I find it so arousing is that I love the idea that I’m turning young Jacob on as well. And if being with his own mother happens to be his ultimate fantasy, then who am I to judge? We all have our quirks.

I actually feel both surprised and honored that Jake shared such an intimate and potentially embarrassing fantasy with me in the first place. So, as a result, I’m just going to do my best to make the most complete version of his dream scenario come true. And just you wait and see. I’m going to roleplay the fuck out of pretending to be this boy’s mother, and I think it’s going to be great, and no one can convince me otherwise!

And so here Jake is, in my bathtub, lying with his head back against the tub as I finish rinsing the last of the shampoo out of his cute, curly, light brown hair. His petite, but muscular body is naked as can be, while I’m still fully clothed. Meanwhile, I’m leaning over the side of the tub, bathing him, just like a caring mother would.

Me (as I wash the suds off of my hands): “Alright, Jacobson, I think you’re all set! Let’s drain the tub and get you dried off.”

Jake (looking up at me with the sweetest eyes): “Thanks, Mom. This was really nice. I can’t remember the last time you bathed me! It’s been so long.”

Yeah, this roleplaying is still going to take some getting used to, but I’m up for the challenge, ha.

Me (brushing off a few bubbles from one of Jake’s shoulders): “You bet!”

I was about to use a generic term of endearment, like sweetheart or Buddy or whatever, but just like how his Mom calls him Jacobson and not Jake or Jacob, I figured I should try to be accurate in how I address him.

Me (leaning in and whispering to Jake): “What does your mom call you in times like this? Like Sweetie or any other nickname like that?”

Jake (recognizing that I broke character and whispering back): “Oh yeah, she calls me Honey or Honey Bear or sometimes just Hon for short.”

Okay perfect. And then Jake nods as if to signal we should resume in character. Fuck, he’s so adorable.

Me (placing my hands on Jake’s waist to guide him up): “Alright, Honey Bear, let’s get you dried off and ready for bed!”

Jake (just beaming with happiness right now): “Sure thing, Mom!”

Yeah, so far all of our dialogue and delivery is probably a little over the top and cheesy, but we’ll work on that. 😛

As Jake stands up, it’s impossible not to notice his rock-hard boner spring up with him, mainly because it’s literally right in front of my face. Fuck, it looks so good.

I’ve already mentioned several times how small his penis is, and even though I obviously haven’t measured it with a ruler or anything, I’m officially pegging it at three and a half inches, fully erect. And I know what you’re thinking. That has to be disappointing, right??

Well, I can’t fully explain it, but it’s not. Not in the least.

I leave Jake standing next to the tub, with his little dick sticking straight out at me, like a hunter dog that’s spotted its target, while I go grab a clean towel to dry him off with. Once I come back, I start with Jacob’s head, and I give his brown curls a frantic rub until they’re all nice and fluffy. It’s notable how easy it is for me to dry Jake’s hair, simply because he’s so short. I know I said before that I thought he was probably 5’6″, but I think that actually might be a little generous.

After using the towel to dry off his ears and face, I move down to his shoulders, then to his chest, making sure to dry his front, back, and sides thoroughly. Jake even lifts his arms high up into the air so I can easily get to his armpits.

Now it’s time for the good stuff. I crouch back down, and my face ends up right back in front of Jake’s now semi-hard pecker. And let me tell you, I want so badly just to take his entire organ into my mouth that I have to use every ounce of willpower I have to resist. I swear I could get both his cock and his balls entirely within my lips right now, and it would be the most satisfying teenaged mouthful I could ever imagine. In fact, I want it so badly that my mouth is literally watering. But still, I restrain myself.

I think it’s actually for the better, though. This tease we’ve entered into, while on some level quite torturous, is also helping build my anticipation. In fact, I really like all this tension and suspense, as there’s joy in the challenge of not giving in. And then on top of that, I feel like it’s also going to lead to an even bigger payoff at the end, when I finally do get to be with young Jacob. I mean, the more teasing we endure now, the more satisfying it’ll be when the fireworks finally go off, right?

And in that sense, this mother-son roleplay we’re partaking in is clearly helping to build the tension, because obviously, if we’re a mother and son, we’re not supposed to be together sexually. And so not only are we pretending that our relationship isn’t sexual, but we know that if anything were to happen physically between us, it would be hugely forbidden, like an enormous taboo. So this just adds one extra layer to the whole will-they-or-won’t-they drama that’s been building for the last half hour.

This makes me think, though, I wonder how Jake is planning for us to cum to this incestuous realization. Like between the two of us, who is ultimately going to make the first move? Who’s going to give in and break down that taboo barrier finally? Does Jake have a specific plan in mind for how he wants all of this to unfold, or is he hoping that I’ll just handle all of that?

I’ll tell you what. For now, I’m just going to go with the flow and see where this whole roleplay leads organically. I kind of like not having a set plan, because I figure no matter what happens, we’re bound to end up fucking each other in the end, right? It’s just a matter of what road we take to get there.

Now that being said, I’m more than happy to add my own contributions to both the tension and the backstory, so to speak. And so now that Jake is all dried off from his bath, I figure there are several motherly things I could do here that aren’t overtly sexual, but hopefully will start ratcheting up this taboo suspense we’re working on building.

So I walk over to the double vanity in my bathroom and open the top middle sliding drawer. In it, I grab two Q-tips and a pair of metallic nail clippers. I don’t even know if Jake saw what I took, but I figure he’ll find out soon enough.

Me (offering my free hand that’s not holding the items): “Here, Honey Bear, let’s go over to the bed.”

Jake starts to walk with me, apparently having no qualms that he’s completely naked.

Me (after stopping in my tracks): “Hon, don’t forget your towel, silly!”

Jake (apologetically): “Oh, sorry, Mom. I don’t know what I was thinking.”

After bending over to retrieve the light green towel from the floor, Jake follows me back into my bedroom, and I have him take a seat at the foot of my bed. I actually pick up his towel and drape it over his shoulders, just so he’s not completely exposed, and also to make sure he doesn’t get too cold. However, this still leaves his 18-year-old cock out in the open for all to see, which I admit probably isn’t the most believable mother-son interaction here, but that’s okay.

Me (as I show him the items in my hand): “Okay, Hon, I’m just gonna clean your ears and check your nails. Is that okay?”

Jake (nods, and then gives me kind of a serious look): “Mom… you can do whatever you want to me. Just tell me what you want me to do.”

Ha. Easy there, cowboy. It seems like Jake might be a little more anxious than I am to get to the good stuff. I kind of like this, though, that I’m the one in control. And it’s definitely not the time to give in to our temptations, at least not yet.

Me (after placing the nail clippers next to him on the bed): “Okay, well I’m gonna start with your ears, Honey.”

Jake gives me a big smile, as if he has no problem with this mother-son character development I’m working on.

I take the first Q-tip, and after bracing the left side of his face with my off hand, I use my right hand to insert the cotton swab just enough to clean out his ear. I give it a few twirls, and lo and behold, quite a lot of wax comes out!

Me (showing Jake the now dark yellow tip): “Jacobson, you really need to be more diligent about cleaning your ears!”

Jake (pretending to be bashful, but seriously, he really does need to clean his ears more often): “Sorry, Mom.”

I then flip the Q-tip around and use the other end to give his left ear another swab, and this one comes out mostly clean.

I then repeat the process with the second Q-tip and his right ear, and it comes out just as waxy. After that, I move on to the following item on my impromptu bedtime checklist, clipping Jake’s nails.

I walk over, grab the small waste basket I keep next to my nightstand, and bring it back to where Jake is sitting on the front of the bed. I part Jake’s naked legs and place it right between his thighs. And then I take his left hand, which I’m still shocked is smaller than mine, and hold his fingers out over the trash, just in front of his exposed penis. To my surprise, his nails are actually in pretty good shape!

I do clip a few of them, and as the clippings fall into the waste basket, I sneak a peek or two at Jake’s adorable little pecker. It still looks as suckable as ever, even if it’s not super hard right now. But then, as I look up at Jake and then back down at his cock, it’s pretty obvious he knows that my focus isn’t solely on his fingernails. He kind of chuckles, and that makes me smile.

Anyhoo, I finish up with Jake’s left hand and then switch to his right, and as I do, I notice his penis is starting to get a little harder.

Me (as I take hold of Jake’s right calf and bring it up to the level of the bed): “Alright, fingernails are done. Let’s check your toenails now.”

Jake’s toes are also in decent shape, and on his right foot, I only have to clip his big toe. But the more noteworthy thing is that with Jake’s leg lifted onto the bed now, in addition to seeing his fully erect cock, I also have a nice view of his balls resting on the edge of my bedspread. He has such a tight little sack, and while that’s not usually a feature on a guy that catches my attention, I guess I’m just so turned on right now that every little piece of Jake’s anatomy is starting to look appealing. God, this might be the horniest I’ve ever been!

And on that note, I think it’s time to take another step forward in this make-believe mother-son adventure. 😛

Before I do, though, I want to clarify one thing. In this whole roleplay, I’m obviously pretending to be Jake’s mom. And clearly, I’m okay with that, as you can tell by my willingness to participate thus far. But one thing I’m purposefully not doing is pretending that Jake is my own son.

I know, I know, that sounds ridiculous. You’re like, that’s the same thing, isn’t it?? Well, to me, it’s not. You see, I have a son, and in fact, he’s basically the same age as Jake. And while I’ll freely admit that I’ve fantasized about my son’s friends on numerous occasions, I have absolutely zero interest in ever thinking about my actual son in that sort of way.

I’m clearly not judging Jake for his thoughts, though, and from the bits and pieces he’s already told me about his mom, it seems like she might have some weird boundary issues with Jake as well, and that’s fine. But the point I want to make is that while I am comfortable helping Jake live out his fantasy about his mom, there are some lines I’m not willing to cross.

Now that I said that, do I think being an actual mom to someone around Jake’s age will be beneficial for this roleplay? Oh, absolutely, I do, and I definitely plan to draw on my real-life experiences as much as I can. But I just wanted to lay this out there: while I am okay with this roleplay as it’s currently progressing, I am not planning to entertain any thoughts of it going in the other direction, if that makes sense.

Okay, with that out of the way, and Jake’s leg up on the bed, and his tiny, little boner pointing straight up at the ceiling, I think it’s time to broach the subject of this barely legal boy’s oh so obvious erection.

Me (as I look up at Jake’s eyes and then back down): “Your little friend down here seems to be all worked up.”

And then I smile.

Jake (with a solid delivery that really sticks to the narrative): “Oh my gosh, Mom. I can’t believe you said that!”

Me (grinning): “What? You didn’t think I had noticed??”

Jake: “Well, no… I mean, yeah, but I can’t believe you pointed that out! And I’m sorry, but I can’t really control that.”

Okay, I have to admit this is legitimately kind of fun.

Me (as I place Jake’s right foot back down on the floor, and then pick up his left one): “Well, Hon, I have to say, he’s certainly a cute little guy. Has he made any new friends at school yet?”

And then I lift my eyebrows suggestively.

Jake (acting all shy): “Mom!”

Me: “What?? I’m just curious if you’ve introduced him to any of the girls in your hall.”

Me (after a slight pause): “Or boys. You know I’d be fine with either.”

Jake (now with a faux annoyed look): “Mom. I’m not into guys like that.”

After a swift glance at Jake’s left foot, which is now on the bed, I realize his nails are all good. So I guide that foot back down to the floor, and now I’m ready to give my full attention to this new topic we have going, because I have to say it’s a lot more interesting than clipping toenails.

Me (defensively): “Okay, okay, I figured you liked girls, but I didn’t wanna assume anything.”

Jake: “Yeah, thanks. But Mom, to answer your question… no, I haven’t introduced my little friend, as you call it, to anyone at school yet.”

Me (as I gently place my hands on his two thighs, forcing them to open up ever so slightly): “So if you haven’t made any special friends at school yet, are you aware of how you can handle this problem yourself?”

Jake (still playing the embarrassed card, but obviously not backing away from the subject): “Oh my god, Mom, are you talking about me jerking off??”

Me (matter-of-factly): “Yep! Jerking off, jacking off, masturbating. Whatever you wanna call it.”

And then I smile again.

Jake (with a deadpanned look on his face): “Yes, Mom, I’m well aware of how that works.”

Me (here’s where I can draw on my real-life experiences as a mom): “Yeah, I know you know all about that. I was obviously kidding. Remember, I’m the one who would wash all your crusty socks, and empty that waste basket of yours, filled to the brim with used tissues, even when you didn’t have a cold.”

Jake (acting like that comment legitimately hit close to home): “Mom!!!”

Jake (with a little bit of a more serious tone): “I mean, you’re not actually trying to make me feel bad for doing that, are you? For touching myself?”

Me (realizing that this is probably a good opportunity to transition this conversation away from the jokes, and into something more real): “No, of course not, Honey Bear. I think it’s totally normal, totally natural, and I’m glad you’re able to do that as much as you want.”

After I say this, for whatever reason, Jake and I both look down at his cock, which is still sticking straight up into the air.

Jake (with a little chuckle, but still kind of a serious tone): “Thanks, Mom. You know my record is eight times in 24 hours? It’s kind of sad, but I wanted to see how many times I could do it in a single day.”

Ha. That’s awesome. And kind of hot to think about him just rubbing his cock raw to keep cumming, over and over and over again. What a little fucking horn dog. I love it!

Me (keeping in the roleplay, but figuring I can ask some follow-up questions): “Jacobson! That is so many times! Did you use any lubricant when you did that?!? I’m worried you could’ve given yourself some serious chaffing.”

Jake (seeming like an open book now): “Ha. Yeah, for probably like the last three or four times, I definitely used some lotion. And then after that day, I don’t think I jerked off again for like a week!”

Me (laughing): “That’s too funny. And too cute. So, if you don’t mind me asking, how do you usually masturbate? Like, do you look at something when you do it?”

Me (whispering for effect here): “Like pornography?”

Ha. I would never usually refer to porn as pornography, but for some reason, I felt like it fit my characterization of Jacobson’s mom.

Jake (after laughing at my delivery on the porn question): “Sometimes, but not always. Sometimes I just close my eyes and imagine a scene in my mind, and that’ll be enough.”

It doesn’t take a genius to know what young Jacob is alluding to here, as he and I both know he’s talking about the scene of his mom (or, in other words, me) masturbating in her (my) own bed. For whatever reason, though, I don’t just want to give in and ask him what scene he’s referring to, as that almost seems too easy. So let’s see how he handles it when I don’t take the bait.

Me (focusing more on him jerking off, than the inspiration of his orgasm): “That’s really cute, imagining you, lying back in your bed, touching yourself with your eyes closed. I can almost picture it.”

And then I give him a big smile.

Jake doesn’t seem too bothered by my redirect, as instead he looks like he’s actually getting even more aroused.

Jake (with a serious tone): “That’s not all I would do.”

Me (playing along): “Oh really?”

Jake: “Can I tell you something really embarrassing?”

Absolutely, you can. But I’m pretty sure I already know what it is. This is where he’s going to bring up the fact that he used to watch me masturbating through the crack in the door. Ha, I just referred to his mom as ‘me’. Clearly, I’m in too deep here with this roleplay!

Me: “Of course you can, Jacobson. You can tell your mother anything.”

Jake (seeming actually kind of nervous?): “Sometimes when I’m alone… sometimes I don’t just touch myself…”

This is interesting. Maybe I don’t know what he’s about to say?

Me (as I give Jake a soft, reassuring rub on his naked thigh): “It’s okay, Hon, you can tell me. I won’t judge.”

Jake (looking right at me): “Sometimes… sometimes, I like to stick things in my butt. And then I cum with them in there.”

Well, isn’t this fucking interesting. I was definitely not expecting him to say what he just said, and I love, love, love this revelation!

This is hot as fuck. I’m sorry if this isn’t your cup of tea, but for me, this twist that Jake just threw out there is a goddamn home run in my book. Thinking about a boy like Jacob, experimenting all alone, by inserting objects up his butt. It’s just so fucking adorably hot and sexy! I’m sorry, it just is.

Me (showing legitimate surprise): “Wow. Hon. That’s definitely interesting, but I think pretty normal, actually.”

I need to know more!

Me (quickly continuing): “What would you stick up there?”

Jake (tentatively): “Oh, um, all sorts of things, I guess…”

Fuck yes. I’m both nodding in anticipation and smiling ear to ear, awaiting further details.

Jake (seeming perhaps surprised and maybe a little relieved that I’m so into this): “Initially. I would stick very thin things, like a pen or a pencil, in there. And then I would just leave them in there while I lay in bed.”

Me (still crouched in front of Jake): “Did you like how that felt?”

Jake (nodding): “I did. And then I moved on to slightly thicker objects like markers. You know, like a Sharpie?”

Right now, I’m picturing Jake, completely naked on his bed, with his legs spread wide open and his feet back up over his head, while he leans forward, stomach all scrunched up, as he works to force a run-of-the-mill black Sharpie pen all the way up his tight, tiny butthole. This is so fucking hot!

Me (so into this): “What else would you put up there? Did you experiment with anything bigger than a marker?”

I know it’s so cliche, but the bigger the object, the hotter this is to imagine.

Jake (appearing to be totally at ease now, sharing everything with me): “Well… the biggest object I ever used was that baseball bat I have in my room.”

Me (flabbergasted): “A baseball bat?!?”

Jake (with a fake annoyed tone): “Mom, not a real bat! You know that miniature souvenir bat, that’s like much smaller than an actual baseball bat.”

Oh my god, I know exactly what he’s talking about. I don’t think we still have it, but my son used to have a mini souvenir bat like that on his bookshelf. And on an unrelated note, holy shit, I had totally forgotten all about our mother-son roleplay here for a second! I guess I was just too engrossed in these tales of anal self-exploration that I had completely forgotten all about our original storyline!

Me: “Oh, of course, Hon! I remember now. That little shiny, wooden souvenir bat, right? It was like maybe 12 or 16 inches long?”

Jake (continuing with his explanation): “Yeah, exactly, you know what I’m talking about. Anyway… so it was quite a bit bigger than a marker in diameter, so that I would get the Vaseline from our bathroom, and I would cover the top part of the bat in it.”

Me (wanting to let him know how much I’m enjoying this): “Oh, Jacobson, I just wanna say how much I love that you’re comfortable enough to share all of this with me. But please, keep going… what did you do after you lubed it up? Was it tough to insert?”

Jake (after pausing to smile at me): “Yeah, it would take some effort. Just to get it started. But eventually, I’d be able to get it in a little, like maybe an inch or so. But that was enough to keep it in. And then…. and then…”

And then Jake pauses as if now he’s back to being nervous to tell me something?

Me (on pins and needles here): “And then what, Honey Bear?”

It’s crazy how that nickname just rolls off my tongue, now.

Jake: “And then I would climb up onto my bed, and you know how my bed is in the corner of my room, like against the wall?”

Me (I obviously didn’t know this, but I do now): “Uh huh, of course.”

Jake (continuing): “Well, then I would back myself up against the wall, and I’d be on all fours, and I would use the wall to force the bat into me. Like it was fucking me.”

Holy fuck. This is the single hottest confession I’ve ever heard.

Me (totally captivated): “How often did you do this? When would you do this??”

Jake: “I only did it a few times. But I remember doing it once during the day, and maybe a couple of times at night when I was in bed?”

Me: “Oh, Hon, was I home when you were doing this?”

Jake (nodding again): “Yeah, every time I did it, I thought you were home. And while I was doing it, I remember constantly watching the door, wondering if you were going to knock, come in, and find me in this position.”

Okay, that’s it. I’m done. I’m so overwhelmingly turned on right now that I just can’t take it anymore. This buildup is too much, and I need a release; otherwise, I think I’m going to explode.

It’s this mental image I have right now. From everything that Jake just told me, I can’t help but recreate the whole scene in my mind, and it’s simply the hottest fucking thing I’ve ever imagined. It’s this combination of Jacob being so shy and inexperienced, but then for him to have such extreme horniness and sexual curiosity that he would choose to put himself in such a compromised position. It’s such an unbelievable turn on.

In my brain, I see Jacob, kneeling horizontally on top of his twin bed, completely naked. His knees are pressed firmly into his mattress, and his little bare feet are pressed against his bedroom wall. And then, with the side of his face resting against the sheets on his bed, he starts slowly moving his hips backwards, cautiously trying to find the point at which the handle of that miniature baseball bat will first make contact with the wall. And once it does, Jake, having already lubed up that skinny little souvenir bat with tons of Vaseline, will use that immovable wall to force that bat further and further into his tight, tiny rectum.

Oh my fucking god. I can picture Jake’s head lifting with his neck arched back, and his mouth hanging open as five, six, or even seven inches of that thin bat disappears inside of his teenaged body. I can hear his mouth, still agape, let out the softest little groan and whimper, as he tries to cope with the intense pressure coming from the inside of his abdomen.

And as Jake fights his young body’s instinct to expel that object and alleviate the pressure, he diligently keeps pushing it back in, over and over again, as an overwhelming mix of both pleasure and discomfort washes over him. On top of that, he’s constantly peeking over at his door, hoping so desperately that his mom will walk in on him. He wants his own mother to catch him in the act so badly, so she can see him at his most depraved and desperate, in the hopes that she can finally see him for who he is, and know that he’s every bit as horny as she is, if not more so.

Okay, like I said, I’ve hit my breaking point. This whole will-they-or-won’t-they dance has gone on long enough. The time has come for me to break this self-imposed taboo, because Jacobson’s mom has had enough.

I climb up onto the bed and immediately take hold of the insides of Jake’s knees. Initially, this tilts his body back, but it also seems to surprise the hell out of him, as Jake starts scrambling backwards on his elbows towards my headboard. As he does this, I firmly pin his legs open and into a butterfly position, and as a result, his short, little cock ends up completely exposed and sticking straight up into the air.

Now you might think, with how obsessed I’ve been with the idea of sucking off that little lollipop dick, that this would be the time. But believe it or not, that baseball bat story Jake just told me has triggered a brand new desire in me, and it’s the only thing I can think about right now.

Me (while forcefully slapping Jake’s thigh): “Flip over! Get onto your knees.”

Jake looks back at me, but doesn’t immediately comply.

Me (even more sternly): “Jacobson! Get on all fours!”

Jake (as he starts to roll over and reposition himself): “Okay, Mom. Okay, I’ll do it.”

Jake now does as he’s told. And not only does he get on all fours as I had asked, but then he also lowers his face down to the pillows on my bed, and then he raises his beautifully toned, little teen butt up and into the air for me as well. Oh my god, he’s presenting his ass to me. For me to do god knows what with. This is so exciting! To be honest, I’ve never really done any sort of butt stuff with a guy before, but for whatever reason, I really, really want this right now.

Now, during this whole repositioning, while I basically chased Jake across my bed, the towel that had previously been draped over Jake’s shoulders wound up in a lump on my bedspread. I figure we have no need for that anymore, so I casually pick the towel up and throw it onto the floor. This leaves Jake completely naked and with his butt up in the air, while I still have my entire original outfit on, jewelry and all. I know I’ve mentioned this a few times before, but I love the juxtaposition here, where I’m fully clothed, while my 18-year-old virgin friend is totally naked, all the while I’m in complete control of what’s about to happen.

Jake (sounding legitimately nervous, though): “What’re you gonna do to me, Mom?”

Me (as I place my two hands on his super tight butt cheeks that feel oh so heavenly firm): “What would you like me to do, Honey Bear?”

Despite being the one in charge, I’m not opposed to taking suggestions. If they’re good suggestions, after all, like I said, I’m new to this, so I don’t really know what I’m doing here, anyway. 😛

Jake (with voice cracking): “Mom…”

Oh my god. He’s so nervous. In fact, he sounds so anxious that he’s actually making me a little nervous now. My heart is racing.

Jake (after pausing for a moment): “Mom… I want you to do anything you want to me. I just wanna make you happy.”

Fuck. I love this whole ‘doing absolutely anything to please his mom’ angle he’s been consistently pushing from the beginning. Basically, ever since I found out about his feelings for his own mother, he’s been repeating that mantra over and over.

And believe me, I plan to take full advantage of this offer. And as I kneel behind him on my king-sized bed, I use my grip on his two ass cheeks to pull them apart, and for the first time, I get a clear view of his hidden, tiny butthole. Yep, there’s no doubt. His penis can wait, at least for a few minutes, because I need to give this cute, wrinkly, tight, tiny opening of his some serious fucking attention.

I love the fact that he’s fresh out of the bath, too. His asshole looks so squeaky clean, and there’s not a single hair in sight. In fact, his entire ass crack appears to be baby smooth. His butthole is obviously puckered and tightly closed right now, but I can only imagine how easily it’ll open up if presented with the right opportunity. But most of all, the one thing I want to do above all else right now is feel this 18-year-old boy’s tender, tiny anus pressed against my tongue. Is that weird? I don’t know why I want to do this, but all I know is I need to eat this boy’s ass so badly right now.

Me (as I lean in to within six inches of his crack): “Jacobson, it makes me sooooo happy to hear you say that I can do anything I want to you. Because there’s one thing, I really, really, wanna do.”

Jake (desperately): “Oh, Mom, just do the thing you want to do…”

I think he knows.

And so I do it. First, I use my hands to spread his ass a little wider, stretching the skin of his crack as far as it’ll go. Then I move my face in and begin with one giant, wide, long, slow lick. I start at his taint, just above his ballsack, and I traverse all the way up his crack until I reach his little stink star. Except it’s not stinky in the least. It’s absolutely delicious.

I stop right on his button, and I twirl my tongue around and around his sphincter, and I let out the biggest moan of absolute satisfaction. Oh, what a glorious, fucking release this is. I needed this so badly. To finally have a physical connection with this boy, and to do it as his mother, and in the most intimate and extremely submissive act imaginable, eating his asshole.

I close my eyes and just savor the experience. He tastes wonderful, as my body wash in fact, but it’s more about the texture against my tongue than anything else. That wrinkly tiny opening of his, and everything that it represents, to know that it’s on my tongue right now, is just a total mind fuck.

Apparently, it’s pretty intense for young Jacob as well, as I feel him start to squirm, but that just makes me grab ahold of him even tighter, and commit even more to making sure my mouth stays buried between his two ass cheeks.

Jake (panicky): “Ohhhhh… ohhhh… oh my god, Mom.”

Based on his tone, I think he’s enjoying this, but it’s hard to be 100% sure. So I decide to ease up just a tad, and I let go of my tight grip on his buttocks, and instead switch to more of a gentle rubbing. And as my hands start to caress his sides slowly, I start alternating between minor, gentle licks directly on his butthole, intermixed with low, satisfying moans emanating from my mouth, just outside of his opening.

Finally, I pull back a little to both admire my work thus far and check how young Jacob is actually doing with all of this. And as soon as I pause my licking, he lets me know.

Jake (with total contentment in his voice): “Oh, Mom… this feels so good.”

Awesome. And fuck, his asshole looks even more inviting than it did a second ago. It’s all shiny and wet from my tongue.

Jake (almost panting now): “Oh, Mom… I never knew you’d want to do that to me. I looooooove that you wanna do that to me.”

Me: “Oh, Honey… thank you so much for letting me lick you there. You tasted soooooo good.”

Jake (back to sounding desperate again): “Oh, Mom… you’re not done, are you?!? Please don’t stop. Please oh please keep going…”

Oh, Jake, I am just getting started. But instead of diving back in for some additional licks, there’s something else I want to do even more. Penetrate him.

So I take my right index finger, and I start at the bottom of Jake’s right thigh, and I start tracing it super slowly up his leg, over his right butt cheek, across his lower back, down past his left butt cheek, and then right back into his ass crack. And then, without any further delay, I position it right on top of his anus, and I give it the tiniest, little push, but not so much as to break the seal.

Jake (with his face buried into a pillow, so his voice is quite muffled): “Oh fuck… fuck yes… oh my god, yes…”

Ha. There is absolutely no doubt what Jake wants me to do right now. So fuck yeah, I’m going to do it.

However, before I begin, I decide to switch from using my index finger to my middle, you know, just because it’s longer. I also figure I should probably wet it first, so I withdraw my hand and move it up to my mouth. I then give my middle finger a full-mouth suck, making sure to leave plenty of saliva on it. Next, I return my wet digit to Jake’s butthole and complete two quick circles around his sphincter before pushing it in. And holy fuck, it goes in so much more easily than I was anticipating.

Now granted, I only have the tip of my finger inside of him, so just up to my very top knuckle, but it’s crazy how easily that went in, and how little resistance there seems to be if I wanted to go in deeper. And guess what, that’s precisely what I’m going to do.

I give my middle finger a little wiggle while also pressing forward, and my god, I slide my entire finger inside of this boy. The only thing that stops me is my two surrounding knuckles, as the base of my index and ring fingers end up bumping into the sides of his ass crack, halting the plunge. Otherwise, I feel like it could’ve gone in way further.

Jake (gasping): “Holy shit!”

Holy shit is right, because this is incredible. But it’s not just great, as it’s also hot! I wasn’t expecting or prepared for this warmth. This is insane.

I mean, fuck, is this what it feels like for a guy to have sex with someone? To stick his cock in another person? Now obviously I don’t have a penis, but my finger is actually inside of this boy right now! Like I’m a part of him, and he can feel me from within. And let me tell you something, it is fucking hot. Both figuratively, and as I mentioned before, literally hot, like 98.6 degrees hot.

Jake (turning his head to the side so I can hear him more clearly): “Oh, Mom, I can feel you inside me right now…”

Me (as I use my free left hand to start lovingly rubbing his exposed lower back): “Oh, Hon, I am. I’m so deep inside you right now.”

Jake (as I decide to pull my finger back slowly, but still leave the tip of it in): “Oh fuck… oh fuck…”

And then before it ever fully exits, I push my finger all the way back in. Then I pull it mostly out again, but this time I admire how wet and glistening my two lower knuckles are, before sliding them back in, yet again.

I do this over and over, maybe a dozen times. And holy shit, it may just be my finger, but I legitimately feel like I am ass fucking this boy. In some sense, I feel like he’s no longer a virgin. At least his asshole isn’t. And let me tell you something else, I absolutely love this feeling! The power I have right now is intoxicating, as I feel like I have total control over every part of Jake’s being, but most of all his mind. There’s no chance he’s capable of thinking about anything else, other than my finger sliding in and out of his asshole.

Jake (confirming his obsession): “Oh god, yes… keep doing this… don’t ever stop doing this.”

In fact, as I continue finger fucking young Jacob, I notice something. I can see that Jake is starting to move along with me, as his hips are now rocking forward and backward in rhythm with my finger. This gives me an idea.

Me: “Jacobson, I want you to do something for me.”

Jake (so obediently): “Yes, Mom. Anything.”

Ha. Awesome.

Me: “Jacobson, I’m going to leave my hand firm, and not move it, and I want you to use your hips to ass fuck my hand. I want you to fuck it good. Nice and hard. Can you handle that?”

Jacob (quickly): “Yes, Mom. Of course, I can do that for you.”

And then he does exactly as I had envisioned. He starts slowly, but he really is moving his hips forward and back. And while I do my best not to move my hand at all, I see his sphincter sliding up and down my middle finger. Fuck, it’s incredible how tight a seal his asshole is keeping around my finger as it traverses the entire length of it.

Jake (after letting out a loud grunt, like an old man lifting something heavy): “Am I… am I doing a good job??”

Me (as I continue to rub Jake’s lower back with my free hand tenderly): “Oh, Honey Bear, you’re doing an amazing job. You’re fucking Mommy’s hand so good.”

Ha. I think that’s the first time either one of us has referred to me as Mommy.

Fuck, this is hot. But I want more, though. I need more. I need to be deeper inside this boy. So I start slowly, inching my hand forward, moving it closer to Jake, and closer to the bed. He can obviously sense this, and he responds by shifting his hips further and further forward each time, trying to gain a little more room to keep on fucking me. But he’s running out of space.

Soon enough, Jake’s hips are all the way down on the bed, and my right hand has followed them there. There’s no more room for him to escape my middle finger, and his whole midsection is pinned against the mattress, forced to stay where it is because of my finger deep inside of him.

Jake (as I keep my hand where it is, but reorient the rest of my body to be better positioned at Jake’s side): “You’re pressing so hard into me, Mom. It’s really intense.”

Me (as I now begin softly running my free hand higher up over his naked back): “Shhhhhh… Honey. It’s gonna be okay. Shhhhhh… I just wanna do this a little more. It feels so good to me.”

Jake (panting now): “Okay, Mom… It’s okay. I can handle it.”

What a good, obedient boy he’s being. And so I use this opportunity to really start exploring Jake’s rectum by curling, uncurling, and even moving my finger around in circles. And I’ll tell you one thing, it is surprisingly cavernous in there!

While I’m doing this, I switch from giving him a loving back rub to more of a back scratch, as I transition to using my nails, albeit lightly, all over his back and shoulders. It feels kind of appropriate that I’m increasing the sensation, both on the inside and on the outside of his body, at the same time.

With my other hand, the one that’s still buried deep within my 18-year-old friend’s rectum, I continue to explore as much as I can, while really trying to focus on what precisely I’m feeling inside of him.

When I extend my finger to one side or another, I can feel the inside lining of his anal cavity. It’s somehow both smooth and bumpy at the same time, but is pretty consistent in all directions. Even though I’m bumping up against his interior walls, as I said before, there does seem to be a surprising amount of room for me to wiggle my finger around in.

Next, I try to extend my middle finger straight ahead to see how far it’ll go, and as I do, I feel something a little different. It’s like a soft little nub.

Jake (fully alert all of a sudden): “Oh my god, that tickles! That tickles so much!”

I’m guessing my nails on his back are getting to be a little too much for Jake, especially with everything else I’m doing, so I quickly lift my left hand off his upper back.

This is fine, though, as I place this now freehand on one of Jake’s butt cheeks, where I use it to help brace my other hand as it continues to dig around inside this boy’s colon. And while I keep moving my finger all around inside of Jake, I can’t help but get drawn back to that little nub I found before, as something about it is just fun to play with.

Jake (more desperately now): “Oh my god, what’re you doing?? It’s so intense! It’s so weird!”

Oh shit. Maybe it wasn’t my back scratching that Jake was all worked up about a second ago. Perhaps it was because I was rubbing this little nub?? Oh my god. Is this his prostate?!?

Me (as I locate the spot once more and give it its most direct pressure yet): “You mean this?”

Jake (arching his neck back): “Yes!!! What is that?!?”

Me (acting like I’m some sort of an expert, when I had no idea what this was a minute ago): “Oh, Jacobson, that’s your prostate.”

Me (as I continue to focus all my fingers’ attention on this apparent point of maximum stimulation): “What does it feel like, Honey?”

Jake (after taking a few seconds to compose his answer): “It feels like… this intense tickling… coming from my insides. Almost like butterflies in my stomach… but better.”

Fuck, I know I’m a broken record here, but this is so hot.

Now, from what I do know about guys and prostates, which, to be fair, isn’t much, but anyway, I’ve heard that when they have their prostate stimulated like this, it can supposedly cause them to drip cum out of their penis. I think that it’s called milking the prostate? That always sounded so fascinating to me, so it definitely seems like something that I should try to do with young Jacob here, right?

Me (while keeping my middle finger inside Jake): “Okay, Honey Bear, I’m gonna need you to flip over onto your back.”

Jake (seeming a little surprised, but compliant): “Oh, okay, Mom.”

Jake immediately starts rotating, and as he does, I contort my right arm to keep from slipping out of him as he switches positions. At this point, my finger’s been inside his warm, moist asshole for so long that it wouldn’t surprise me if my finger tip had started to prune, ha.

Anyhoo, I’m able to pull off the contorted reposition, as we both adjust our bodies without my finger ever popping out. We end up with Jake now lying flat on his back, with his head resting comfortably on a pillow, and me between his spread open legs. And of course, my middle finger is still plugging his hole.

Jake looks at me, kind of smiles, and then does the sexiest thing. He voluntarily takes hold of his knees, pulls them back, and pushes them apart, and in doing so, forces his legs to open up even wider for me. This tilts his entire lower body back and gives me the best possible access I could ever ask for to his butthole.

Me (with a mischievous grin): “Oh, Honey, you love having your mommy between your legs right now, don’t you?”

Jake (quietly): “Oh, I do, Mommy, I really do.”

Ha. I have him calling me Mommy, now. Awesome.

Me (figuring I should take advantage of this great position, so I start sliding my middle finger in and out of him again): “Do you like it when I do this, Jacobson? Do you like when I finger fuck your tight, little butthole?”

Jake (after closing his eyes): “Oh, Mom, I love it so much. I love that you’re fucking me in the ass. I’ve wanted you to do this for so long.”

Fuck. This is so amazing. You have no idea how many years I spent on this same bed, desperately trying to seduce, convince, reason with, and even beg my husband Greg, to make love to me simply. I’m talking about pleading with him for even ten minutes of just boring, old vanilla sex. And even that was a torturous, painful struggle.

So many times, he’d say yes ahead of time, only to ask us to put it off one more night. So many times, he’d act like he supposedly wanted to, but then blame his back hurting, or stress from work, or having to get up early the next morning, as a valid reason why he couldn’t make love to me after all. I heard every excuse in the book. And not only did the lack of sex hurt from a disappointment standpoint, but even worse, it made me feel so unwanted. So unpretty. So worthless.

But this boy right here, with his legs spread open for me on my bed? Holy fuck, we haven’t even gotten to the actual sex yet, and this is so goddamn fulfilling. I know I said before that last weekend was therapeutic, but this is an absolute joy. I love, love, love how kinky Jake is. And I love even more that he’s only 18!

I also love how he confided his deepest, darkest secret to me. Like, seriously, has Jacob ever told anyone else about his feelings for his mom before? I’m guessing not. But he told me?!? That is so fucking hot.

I love it all so much that I legitimately don’t even care that Jake’s fantasy isn’t even about me. All I know is that I’m the one making his dream come true.

What I do care about is the fact that Jake’s so turned on right now, and that he’s willing to do anything I want. And neither of those things was ever true with my husband. Not even for a second.

Me (forcefully): “Oh, Jacobson, I love the way I’m pounding your ass right now. I’ve wanted to do this to you forever, too, and it turns me on so much that you love it as much as I do.”

Jake (quietly and with his eyes still closed): “Oh, Mom… I want you to fuck me harder. Please give it to me even harder.”

Wow. You don’t have to ask me twice! Did I mention I was having fun before? Because this is about to get even better.

This time, when I withdraw my finger, I actually pull it all the way out, which I hadn’t been doing. Jake gasps. And then I find his opening, wiggle the tip of my finger ever so slightly, and then penetrate him again, plunging my entire middle finger back in, all in one motion.

Jake lets out another huge grunt while he diligently continues to hold his own legs back for me.

Me (sternly): “How did that feel? Did you like that even more?? Did you like feeling me leave and then re-enter you?!?”

Jake (after turning his head to the opposite side): “I did… but I still want it harder. Please, Mom, don’t hold back. Just give it to me, Mom.”

God, it’s impressive how committed he is to calling me Mom. Initially, I had thought that once we started getting physical, we might transition more into just plain old Becca and Jake being together, but that clearly isn’t how this is progressing.

Me (as I withdraw entirely and slam him a few more times, each time harder than the last): “How’s that?!? You definitely like this better now, don’t you?? Your mom’s pretty strong, isn’t she?!?”

And then I think I grunt a little, from all the effort I’m putting into this.

Jake’s cock, by the way, is so goddamn hard, and his mushroom tip is so bright red, it honestly looks like it might explode. And I know I’ve said this before, but he must have the most enormous head on a penis I’ve ever seen, as it just looks enormously out of place. Although, to be fair, it’s also possible it’s a normal-sized head, that just looks huge in comparison to the extremely short and thin shaft he has. Either way, it’s too appealing to resist.

In fact, I have made up my mind right here and now. I mean, this boy said he once jacked off eight times in a day, right? I know I definitely want to end up having sex with him, and I know he already came in his pants a little bit ago, but I can still blow him here, right? If he cums in my mouth, he’ll still be able to rally for a third orgasm later on tonight, right? I bet he will.

So fuck it. I’m going to finger him and suck him off, all in one motion, right the fuck now.

And so the next time I slam my finger into Jake, I leave it in there, and then with him still holding his legs open for me, I dive in face-first, right for his cock.

I use my free left hand to take hold of his small shaft, but then I quickly transition to fitting his cock right into the webbing between my thumb and index fingers. Then I press firmly in and around the base of his penis, which both holds all of his pubes down, but also forces his boner straight up into the air, completely exposing it.

I give Jake one more glance, and with his eyes still closed, I move in. I immediately take that plump mushroom tip of his and audibly slurp it into my mouth. And as I start really sucking on it, like with all the suction power I can muster, I feel Jake react.

Jake (as his abs contract and his upper body lurches forward): “Oh god!!”

With my right middle finger now all the way back inside of Jake, I start wiggling it around while simultaneously beginning the journey of my lips down the shaft of his penis. And while I’m not sure what to expect with such a small dick, it doesn’t take me long to realize that holy shit, I now have the entire length of this boy’s cock inside of my mouth. That was so easy!

I know this because my lips make contact with my hand holding him at the base, and while I can sort of sense his mushroom tip near the back of my throat, I feel like I still have quite a bit of room to spare. And holy fuck, this is incredible. I’ve never been able to suck the entire length of a cock before!

This is such a revelation. I love the fact that I can so easily take his full length! In fact, I want even more. So I remove my left hand from the base of Jake’s penis, and I keep pushing forward until my teeth start to gently press into the soft pubic flesh that surrounds his cock.

And holy shit, I love this feeling, and I love the fact that I’m deep throating this boy like some sort of porn star! I had never contemplated this before, but I guess one huge benefit of being with a tiny cock is the ability to give fantastic blow jobs! Now granted, maybe having actual sex with a three-and-a-half-inch penis will end up being disappointing, but at least for now, I don’t care. And that’s because I am really into this. And you know who else is really into this? Good old Jakey-boy.

After I started blowing him, Jake took both of his hands off of his legs and started holding my head instead. Meanwhile, now that I have his cock securely in the back of my throat, I’m content to shift my focus back to my other project at hand, this boy’s prostate.

It takes some maneuvering, but soon enough, I find that favorite little nub of mine buried deep inside Jake’s rectum. And once I do, Jake goes absolutely nuts.

Jake (with the sound of panic in his voice): “Oh fucking, fuck fuck fuck!!”

Ha. Perfect. Just the reaction I was looking for! Although one downside to having Jake’s cock in my mouth is that I kind of lost the ability to track that whole milking experiment I had wanted to do. Oh well! 😛

Much more importantly, though, I really want this boy to blow his fucking load. So I keep pressing that internal pleasure button of his, and while I do, I switch to an actual slurping and sliding motion up and down Jake’s cock. Each trip down his shaft ends with my teeth making contact once again with his pubic tissue, but Jake certainly doesn’t seem to mind. In fact, I think he’s about to cum.

Yep, he’s definitely cumming. Fuck yeah.

Jake (with the loudest exclamation he’s had so far): “Ooooooooohhhhhhhhh god. Ohhhhhh god.”

And there’s the first squirt. I feel it right at the opening of my esophagus, and it’s both warm and plentiful. And then the second one comes. And holy shit, as he’s jizzing into the back of my throat, I continue to repeatedly press down on that little, soft prostate of his, and I know this sounds crazy, but I swear I’m controlling his orgasm.

I’m timing the pressure of my finger, such that each time I push down on that nub of his, I feel a warm glob hit my uvula. Ha, it’s almost like I’m pressing a dispenser on the top of a lotion bottle and squirting it into my own throat!

Speaking of which, woah this is a lot of cum. It’s all pooling near the back of my tongue, and I haven’t been able to swallow any of it down yet. This is quite overwhelming, as I feel like I’m getting waterboarded with semen. It both tickles and feels like I can’t breathe. And I also feel like it’s about to trigger my gag reflex, and shit, now I even feel it up in my nose.

Me (with a completely involuntary response): “Aaaaaaachoooooo!!!”

Ah, Fuck!

One of the most enormous sneezes of my life comes entirely out of nowhere and blindsides both Jake and me. There is snot everywhere, as it comes out double-barreled from both of my nostrils, and I can feel it all over my lips and chin.

Oh my god. I can’t believe I just did that! I can’t believe I just sneezed right in the middle of giving this sweet boy his first-ever blow job. Come on, Becca, do better!

To be fair, though, Jake doesn’t seem to mind, as now that I take a look at his face, his eyes are closed, his head is resting on the pillow, and he has the look of total contentment on his face. Okay, I guess it wasn’t that much of a disaster.

I definitely need to get myself cleaned up, though. But before I can even do that, I need to extract myself from Jake, ha. Now that the fireworks have ended, I gently slide my middle finger out of Jake’s butt and also remove my mouth from Jake’s completely gooey and semi-soft cock.

And while it’s safe to describe Jake’s crotch as a complete mess right now, there’s no doubt my face is in even worse shape. But as I gingerly start to assess the damage from that disastrous sneeze, I notice something weird about all the boogers and snot that are covering the lower half of my face. They’re very runny. Like so, liquidity in fact, that they’re actually dripping off of my chin.

I’m about to reach for the box of tissues I keep next to my bed, because I don’t want the snot to get all over my sheets, when it finally dawns on me. Holy fuck. These aren’t boogers. I just sneezed a whole bunch of barely legal cum out of my nose!!

Ewwww. That’s kind of gross. And just to ratchet up the embarrassment, right as this is dawning on me, I see Jake open up his eyes for the first time.

Jake (with eyes instantly as wide as saucers): “Oh my god, Mom! Your face!!”

Yeah, thanks, Bud. I hadn’t noticed. And also noteworthy here, you’re still calling me Mom?! I’d think that after blowing such a huge load and seeing the semen eruption that took place from every orifice of my face, perhaps we’d put a pin on this roleplay for a few minutes? But I guess not, ha. But it’s fine, though.

Me (shrugging my shoulders): “Yeah, things got a little messy there.”

Me (pointing to the side of the bed): “Can you grab a few tissues for me?”

Jake (quickly getting me the Kleenex): “Oh, of course! One sec.”

I finally get to start cleaning up my nose, mouth, and chin, and if nothing else, Jake has the sweetest, most appreciative look on his face right now.

Me (after giving my nose a hearty blow to flush any remaining jizz out of my nasal passages): “I feel like there should be a term for what just happened there. Like I gave you a snot job or something.”

Jake (smiling): “Ha. I actually think there is. I think it’s called an Angry Dragon.”

Me (mostly done wiping my face now): “Ah. That does sound vaguely familiar, not that I’ve ever done one before, ha.”

Me (smiling while still holding the tissues in my hand): “So tell me, how was your first Angry Dragon??”

Jake (subtly shaking his head from side to side): “It was so amazing. Thanks…”

Jake (after hesitating, and very timidly): “…Mom?”

Me: “Maybe just Becca for now.”

Jake (smiling): “Yeah, sure, thanks, Becca.”

But don’t think for a second that we’re actually done here. I know Jake has already cum twice, but I have faith in this 18-year-old’s sexual stamina. I’m not worried.

What I am concerned about, though, is how I’m still fully clothed and how that needs to change. Pronto.

Because as much fun as I’ve had probing, licking, and sucking every part of Jacob’s cute, young body, I also think it’s time for some of that physical attention to start making its way back to me. And I actually have just the plan in mind.

Me (as I casually walk over to throw away all the used tissues): “So I hope you’re not planning on leaving just yet, are you?”

Jake (looking so innocent, sitting all naked on my bed): “Oh, no, of course not. I’m up for… I’m up for whatever you… What did you have in mind?”

Me (placing my finger on my lips as if I’m contemplating an idea): “So I was thinking… that we should do one more little scene.”

Jake (very agreeably): “Okay. What do you wanna do?”

Me: “I want you to leave this room, and I want you to stand out there in the hallway, just as you are. Completely naked.”

Jake (looking over at my bedroom door): “Oh, okay. Out there?”

Me (smirking now): “Yep! And I want you to wait out there and listen. I want you to listen for that buzzing noise you said you were always so excited to hear.”

Jake’s eyes instantly light up as he realizes what my plan is. And that the plan is for us to recreate the scene of Jake spying on his mom while she masturbates.

Jake (so excitedly): “Oh my god. Oh my god, I would love that.”

As soon as I see how into this Jake is, I casually start walking over to my closet. Once I’m there, I open the secret special shoebox I keep in the back of my middle shelf, and I retrieve all the vibrators I own. Spoiler alert, it’s not a lot. I only own three.

Anyhoo, I grab the trio of sex toys, and I bring them back and place them on the bed in front of Jake. The first one’s a giant wand with a big, round, vibrating ball on the end. The second one is just a standard brutal white vibrator. Then, finally, there’s an elaborate rabbit toy that has a turning, beaded dildo part along with an extension that’s meant to stimulate the clitoris. The rabbit one, despite being the fanciest of the three, is actually the one I use the least. Anyway, my idea is to see which of these three is most similar to the vibrator Jake’s mom supposedly uses.

Me (looking at Jake): “Okay, so which of these…”

Jake (interrupting me before I could even finish my question): “That one! The white one.”

Jake emphatically points at the basic, hard, white, and smooth 6-inch-long vibrator in the middle of the other two. Okay, apparently this one’s clearly a match?

Me: “Is this similar to what your mom would use?”

Jake (definitely): “That’s exactly what my mom uses.”

Me: “Okay, perfect.”

Jake looks at me with such unbridled anticipation that I’m now 100% confident this boy is going to have zero problem cumming for a third time in a row. I mean, he looks like he just won the lottery, he’s so excited! And it goes without saying, but his excitement makes me excited. I’m so pumped. And so turned on.

Me (as Jake continues to just stare up at me like a puppy dog waiting for a treat): “Well, what are you waiting for?? Get your naked ass out into the fucking hallway!”

Jake (hopping up): “Okay, Mom!”

And as I watch this adorable teenage boy happily bound his way over to my bedroom door, I can’t help but stare at his cute, little, rock-hard butt cheeks as they bounce up and down. Soon enough, he’s going to be inside of me, and my hands will be grabbing onto that perfect 18-year-old ass, pulling it, and him, as hard as I can into me.

But that’s all in due time. Before we even get to that point, I need to recreate this boy’s favorite memory of all, watching his own mom pleasure herself. The only difference is this time, he’s going to have a much, much better view of everything she’s going to do.

*****

Part 3…

My assignment is straightforward. I need to recreate this scene for Jake as best I can so he can live out his ultimate fantasy. I’m realizing, though, that I probably should’ve gathered more information from this 18-year-old virgin before I sent him out into the hallway completely naked, because there are a lot of details I’m still pretty hazy on. It’s fine, though, as I think I have enough to go on, since I already have a general sense of what he and his mom are like.

Anyway, here’s what I do know. I know Jake would peer through the crack of his mother’s bedroom and watch her masturbate with a vibrator. He would stand there and spy on her, while she would bring herself to orgasm, and then he’d retreat to his own bedroom once she was done. So that’s what we’re going to try and recreate here, with the obvious caveat being that I’m expecting our version to have a different ending.

The good news is not only do I know the specific toy Jake’s mom would use on herself, but, as luck would have it, I actually own the same vibrator! So that part is easy.

One thing I don’t know, because I never asked, is what his mom would typically wear while doing this. From the bits and pieces Jake’s told me about her, I find it hard to believe that she’d wear a thong to bed, like I currently have on. Jake has mentioned that his mom never seemed to date, so I’m going to go out on a limb and assume her typical choice of underwear is probably more practical than sexy. Which is fine, as I have a simple pair of white cotton undies I can easily change into.

As I start undressing in my closet, with Jake still patiently waiting in the hallway like a child on timeout, I start thinking about what else I should wear. Maybe I should put on a simple, oversized t-shirt? That seems like something comfortable for Jake’s mom to sleep in night after night, so that’s probably appropriate. Okay, so I think I’ll go with those two pieces of clothing, cotton undies, and a t-shirt. No bra.

Now you’re probably wondering why I’m stressing so much over these seemingly minor details, but it’s simple. I want to make this scene as hot as possible for Jake. He confided in me such a personal thing that he has sexual feelings towards his own mother, and while it was pretty shocking to hear that initially, I’ve come to realize that his act of confessing is definitely a massive turn-on for me. I love knowing his deepest, darkest secrets. And in some weird way, it’s almost like I want to reward him for telling me them.

I kind of also like the challenge of it. I like trying to recreate a scene that captures how he and his mom actually interact, while also making it as hot as possible for Jake. The trouble is, without much information, I’m going to have to improvise a lot. But the good news is, Jake seems to be pretty satisfied with how our roleplay has gone thus far, so I think I’m doing something right!

Okay, it’s time to finish getting ready here. I already picked out the perfect t-shirt, as the baggiest shirt I own also happens to be one I got as a Mother’s Day present many years ago from my own son, that says “Let’s Taco ‘Bout How Great a Mom You Are” with a picture of a giant cartoon taco. I figure it’s appropriate to wear, given our mother-son roleplay, even though it’s corny as shit. Ha, that in itself was a pun, given the corn shell on the taco! 😛

Anyhoo, the only thing left to change is my underwear. But as I take down the black thong I had put on earlier tonight, when I had been dressing to impress, I can’t help but notice how much of a flood zone it is down there. Holy shit.

I honestly can’t remember the last time I was this wet! I’m sure it’s the result of everything that’s gone on over the past hour with Jake. From the initial premature ejaculation incident, to the bath, to all the licking and fingering of his tight, little sexy 18-year-old asshole, to finally getting the chance to engulf that undersized, but engorged penis of his. I think this whole time I’ve been getting more and more turned on, and now I’m simply overflowing with desire, both literally and figuratively.

As I remove my underwear, I can even see the trail of my own cum stretching along with it as I pull the garment down. At first, I think about giving myself a thorough wipe, just so I can start anew with the clean pair of cotton undies, but then I reconsider. I actually think it’s a good thing for Jake to see his mom as wet as possibly, so instead I carefully swap out my underwear while retaining as much of my natural lubrication as I can. I definitely think that’s the way to go.

Alright, let’s do this!

As I climb up onto my bed, for a moment I contemplate whether it would be more accurate for me to be under or over the covers, you know, to be true to how Jake’s mom would actually masturbate. But then I realize there’s probably a limit as to how vital these minor details are, so I’m just not going to worry about it. In other words, I’m going to settle in on top of the covers, and I’m also going to leave the lights on, because I just want Jake to be able to see as much of me as possible.

So I get myself into position. I lie my head back onto my pillow, pull my taco t-shirt up just enough, and then I raise my knees and spread my legs open. And then for the final piece of the puzzle, I pick up my trusty, white vibrator and get it ready to go.

Now, one other difference between this scene and the one Jake described from his own house is that my bed is oriented differently in relation to the door. Jake had talked about how his mom would leave her door open just a crack so that he could watch her through it. With my bedroom, that’s simply not possible. It seems like Jake has already realized this, as he left my door completely open when he went out into the hallway. But again, who really cares if it’s not 100% accurate?

Speaking of Jake in the hallway, though, I actually can’t see him despite the door being wide open, and I also haven’t heard a peep out of him, either. I have to assume he’s still out there, though, right? Standing there all naked, nervous and excited, with his tiny, little penis hanging out, probably still a little droopy from cumming twice tonight already!

It would be kind of funny, though, if he just panicked, had second thoughts, and got the fuck out of here while I was busy changing. I’m guessing that didn’t happen, though. 😛

Actually, scratch that. I’m pretty damn sure he didn’t leave because all of his cum-covered clothes are still in my washing machine! Ha. Nevermind. But that reminds me, I probably should move those over to the dryer at some point, but I’m definitely not bothering with that right now.

Okay, it’s go time. With my legs still spread, I slowly turn the bottom of the vibrator until I feel the battery-powered device come to life. I actually don’t crank it up all the way, but I turn it on just enough so that I’m confident Jake will be able to hear it from the hallway. And so after taking one last glance at my open doorway, I exhale loudly, close my eyes, and place the whirring phallic-shaped device directly onto the cotton fabric covering my clit.

Ohhhh, fuck, this feels good. In fact, this is amazing. Holy shit, did I need this! I mean, seriously, I probably need to come up with a different plan here, because I’m going to orgasm in a matter of seconds if I keep this vibrator pressed against my clit like this. And as great as that would feel in the moment, I definitely don’t want to cum just yet.

So I actually take my vibrator and move it away from my vagina and instead start slowly tracing it up and down my thighs. As I do this, my curiosity gets the best of me, and I open my eyes ever so slightly to see if young Jacob has appeared at my door yet. But to my surprise, he hasn’t.

I feel like I need to know when he finally shows up, so what do you think I should do? I do that thing where you squint your eyes and leave them open just the tiniest amount where you can sort of see out between your eyelashes, but it still looks like your eyes are closed to someone else.

And then I move my vibrator back to my clit, and it feels fucking amazing, so I move it away again. Rinse, repeat. I do this a few times.

Still no sign of Jake, though. Fuck it, maybe for some reason he can’t hear the device, so I’m cranking this baby all the way up. Doing this does make it noticeably louder, but it also makes the vibrations almost too intense, so now I’m no longer touching myself with it at all, and instead just kind of holding it above my crotch.

And then through my squinted eyes, I see it. Finally! Jake’s head is ever so slightly popping out from behind the right side of the door frame, and he looks so fucking adorable.

Ha, I wonder if he really couldn’t hear the vibrator at first, and cranking it up is what did it? It’s like the bat signal wasn’t initially bright enough, I guess. 😛

Well, who cares, because Batman is here now! Although, to be honest, Jake is definitely more of a Robin than a Dark Knight, ha, but that’s okay.

I mean, sometimes you want to get wined, dined, and sixty-nined by a dapper Bruce Wayne. And that can be great and all. But other times, it can be appealing to be the one in charge. You know, where you find your own little Robin, and not only do you get to take his virginity and own it forever, but you get to show that shy Boy Wonder a world of pleasure that he never even knew existed. And if you do that, you can be confident that he’s going to remember you for the rest of his life, which is a fantastic thing to think about.

You know what’s less impressive? Jake was just standing there, peeking out from behind the doorway. Why won’t he just come in? I don’t want to have to call him in. I want him to creep up on me while I pretend my eyes are still closed, and then I’m going to open them up and act all surprised that he’s standing there right in front of me. Is that too much to ask?

On top of that, I’m kind of losing interest in this vibrator. I’m still at the point where holding it against my clitoris is too much stimulation, but running it along my thigh is not enough. You know what I want? I want his warm mouth wrapped around my clit, not some cold, complex piece of plastic pressed into it. Come on, Jake, get the fuck in here already!

I will tell you one thing, though, even through my squinted eyes, it’s notable how small and cute Jake appears out there in the hallway. It’s just his head poking out, as that’s the only part of him I can see, but he looks so short! Maybe he’s leaning over, though?

I wonder if he’s still limp from his second cumming, or if there’s any possibility he’s already got a new boner? Not that I would be able to see it, though, as it’s hard enough to see while pretending to have my eyes closed, but also because his itty bitty dick probably isn’t long enough to poke out from behind the doorway, ha.

I kid, I kid. I actually really love the fact that he has such a small penis. I’m sure part of it is the novelty, in that it’s interesting to get to see and feel a pecker that size for the first time. And then there’s also the innocence and youth aspect, where his small cock just makes him seem even younger than he already is. But you add it all up, and it’s definitely not a negative. And I say this even with the expectation that sex with him probably isn’t going to be as fulfilling, but I’m okay with that.

I just really wish Jake would stop hiding and get his ass in here! I know, maybe I need to ham it up a little. Like, make some noise myself? I can do that.

I take my vibrator that’s still running on full blast, and I move it down towards my vagina, and then I press it into my underwear, forcing the fabric against where my opening would be. It feels nice, perhaps even better than when I was stimulating my clit, and I let out a small moan of satisfaction.

Holy shit, am I still so ridiculously wet? In pressing the toy against my underwear, I can feel it sliding around like an oil slick, and I’m sure my cotton undies must be showing visible signs of all this wetness, too. I wonder if Jake can see that from where he is? I hope he can, so that he can know how much he’s turning me on.

Whoa, maybe that did the trick, because here he comes! Jake just took a step out and is now standing right in the middle of my bedroom doorway.

Me (pressing my vibrator even harder into my underwear): “Oooooooooohhhhhhhhhh.”

I think this is working. Now Jake is slowly walking towards me. He’s being very quiet as he approaches, though.

Me (as I move the sex toy back up to my clitoris): “Oh my god…”

Jake continues to tiptoe forward until coming to a stop about three feet in front of the bed. Okay, it’s time to open my eyes.

Me (after immediately locking eyes with Jake): “Oh Jacobson, what took you so long??”

Jake (standing there completely naked, and holy shit, he actually does have a hard-on): “Sorry, Mom… I just… I just wanted to watch you for a bit, first.”

I’m not going to lie, that question I just asked was purposefully misleading.

Me (as my vibrator continues to whir against my pussy): “No, that’s not what I meant.”

As expected, Jake looks confused.

Me (as I spread my legs wider, while moving the toy to the side to give Jake an even better view of my soaking wet undies): “What I meant was, why did it take you so many nights of watching, until you finally walked in here?”

Now obviously, the answer is because all those other nights were real life with his actual mother, and this is all pretend with a woman he knows already wants to have sex with him. But what I’m actually attempting to do here is point out something that I’m 90% sure is true, that his mom has been aware this whole time that he’s been spying on her.

Jake (staying in character without missing a beat): “You’ve known that I’ve been watching you??”

Me (still staring right into Jake’s eyes): “Of course I’ve known, Honey Bear. I’m your mom. I’ve always known you were there, peeking through that crack. I didn’t want to make it obvious that I knew you were there, but I’ve always loved seeing your cute little face staring in at me.”

Jake looks quite stunned. I can only assume he’s contemplating whether his actual mom knows he’s been spying on her and the ramifications of that.

Me (I’m obviously going to keep going with this): “And as much as I always enjoyed having you watch me from afar, I wanted so badly for you to open that door and come on in. It was like every time I saw you appear, I was hoping and praying that would be the night where you’d finally get the courage to come on in… and see up close… exactly what your mom was doing to herself.”

Jake (looking sad, almost?): “Oh, Mom…”

Me: “Yes, Honey?”

Jake (very apologetically): “I’m so sorry, Mom. I wanted to so badly. I swear I did. I’ve always wanted to come in. I’m so, so sorry.”

Aw, poor guy. I’m not actually trying to make him feel bad!

Me (as I turn the vibrator off and place it next to me on the bed): “It’s okay, Jacobson. It’s okay, Honey. Don’t feel bad. All that matters is you’re here now.”

And then I give him a huge smile.

I want to reach out and touch Jake to comfort him, but I’m kind of stuck with my legs spread open, and I don’t really want to get out of this position, as I kind of like how I’m presenting my vagina to him, even if it’s covered.

In fact, I see Jake is now looking right down at my pussy. He must be able to see how wet I am. How wet he’s made me.

Jake (speaking softly, but with an intense look on his face): “Oh my god, Mom.”

Me (sweetly): “What is it, Honey Bear?”

Jake (seeming hesitant): “It’s… it’s… It’s that smell. It’s so strong.”

Ha. Just what every woman wants to hear. It’s obvious what Jake is referring to, though, as I, too, am getting more than a whiff of my vagina, and I’m not even directly in front of it like he is. Interestingly enough, I can’t actually tell from his expression whether Jake thinks my aroma is a good thing or a bad thing.

Me (figuring I might as well be up front): “That’s my vagina you’re smelling, Hon. Is it okay?”

Jake slowly nods.

Me: “Do you like the way it smells?”

I have to keep in mind that while we’re obviously in the middle of this whole elaborate roleplay, I’m pretty sure Jake has never seen any sort of female anatomy in real life before, well, at least not up close. Hence, this is probably the first time this boy has ever been exposed to the smell of pussy. That’s kind of hot to think about.

Jake (nodding again): “I do. And it… it… It smells so familiar, too.”

Ha. Is he going to make a joke about how, since I’m supposed to be his mom, that means 18 years ago he came out of this vagina, and now he’s remembering what it smells like? Obviously, that’s ridiculous, but I wonder if that’s where he’s going with this.

Me (genuinely curious): “What does it remind you of, Honey Bear?”

Jake doesn’t immediately answer.

Jake (seeming timid again): “Can I confess something to you?”

I have to say, I love this trend of Jake confessing various things. Every time he asks that, I’m so excited to hear what he’s about to say next.

Me (trying to downplay my excitement): “Of course, Hon.”

Jake: “Your vagina… it smells so much like your underwear always does.”

Well, well, well… isn’t this interesting.

Jake: “I know that seems obvious, like why wouldn’t it. But it really, really does.”

Okay, so the takeaway here is that Jake has a habit of going through his mom’s underwear drawer.

Jake (very apologetically): “I’m so sorry about this. But whenever you would leave the house, I couldn’t help myself, and I’d often go through your laundry.”

Ah, even more interesting.

Me (this is kind of hot): “And you’d be looking for my dirty underwear?”

Jake (looking like a guilty puppy dog right now): “Yeah.”

I’ve heard that supposedly a lot of vaginas do smell similarly, so I guess it’s not unreasonable that mine really would remind him of his mom’s.

Either way, I need to know more!

Me: “And what would you do with my undies once you found them?”

Jake (after a pronounced swallow): “I would smell them. And I would hold them to my face. And I would lick them. And then I would suck on them.”

Me (I’m not sure if it’s even possible, but I think this is making me even wetter): “Did you like the way they tasted?”

Jake (nods): “I did. And sometimes I would find little bits of residue. Like a dried, crusty white layer on the inside of the crotch. And I would scrape it with my fingernail to loosen it.”

Wow. This is quite graphic and kind of gross. But I love it. I love the shamelessness of it all. And I love the fact that there’s no way he’s making this up.

Jake (continuing): “And then I would lift the underwear to my mouth, and I would push the flaky, little, white, crusty bits onto my tongue. And I would suck on them. And they would melt in my mouth.”

Me (wow, this keeps getting more and more explicit): “So what you’re saying, Jacobson, is that you would secretly raid my dirty underwear, so that you could eat the dried secretions from my vagina? You really would do that?”

Jake (still looking genuinely remorseful): “I would. I’m so sorry, Mom. I’m so weird, and gross, and pathetic. I don’t know why I did that.”

I know why he did it. And he really is all three of those things he just listed, but that’s what I love about this.

Me: “It’s okay, Honey. I’m not mad. I’m not mad at all.”

Me (looking down at my own crotch): “Would you like to take off the underwear I’m wearing right now? And would you like to put them in your mouth, so you could taste all of my secretions… while they’re still wet?

Jake nods again, but more emphatically than before.

Me (this is all so fucking hot): “Because I would love to watch you suck on them… to see how happy it makes you.”

Me (as Jake doesn’t immediately respond): “Well… what’re you waiting for?”

Jake (still looking subdued, but I can sense some combination of nervousness and excitement): “Oh, sorry.”

After apologizing, Jake kneels at the front of my bed, which results in his face ending up mere inches away from my soaking wet crotch. He gingerly slides his fingers under the elastic band at my waist and then starts to remove my underwear slowly. And as he pulls them up my thighs, I can see, hear, and even feel the intensity of his breathing pick up, as his warm breath is noticeable on the inside of my legs.

Once he slides the underwear completely off my feet, Jake then takes my damp, white cotton undies and slowly moves them towards his mouth. But the interesting thing is, even after all this discussion about his mom’s dirty underwear and how much he loved sucking on them, the wet piece of clothing currently balled up in his hand almost seems like an afterthought.

And that’s because this cute, little 18-year-old virgin is staring daggers at my now completely exposed, wide-open pussy. I still have on my ridiculous taco t-shirt, but that’s the only thing I’m wearing right now, and it’s safe to say that Jake is enjoying the view of me being completely bottomless. And with how captivated he looks, it’s also pretty obvious he’s never seen a vagina in real life before. I fucking love this moment!

And with his eyes still glued to my vulva, Jake makes a half-hearted attempt to open his mouth and take a symbolic bite of my undies, but it’s clear that both he and I have already lost interest in this storyline.

Me (staring at Jake, while Jake stares at my vagina): “Honey… would you rather suck on my pussy itself, instead of on my underwear?”

Jake doesn’t bother answering, but instead just casually drops my undies to the floor, takes ahold of my legs, and dives right in. He comes in with the widest tongue I’ve ever seen and just starts licking, from bottom to top. It’s unlike any time I’ve ever been eaten out before, because it’s almost as if it’s non-sexual. You see, usually when a guy goes down on me, there’s clearly an element of him trying to make me feel good. But this is nothing like that.

Instead, this appears to be more about Jake trying to consume me, to devour my vagina, and to get every last drop of my juices into his mouth, as if his life depends on it. And ironically, even though he’s totally focused on what he wants to do, and even though he’s not making any contact with my clitoris, it’s still somehow the hottest instance of oral sex I’ve ever received.

Picture Jake on a sunny, 95-degree summer day, holding the most top-heavy ice cream cone imaginable, dripping on all sides. And then picture the race against time he’s facing, to lick that cone before it melts frantically. That’s how he’s licking me right now, with that sort of gusto, with that sort of urgency, like a boy eating ice cream, and I fucking love it.

He’s also focusing so much on my vaginal opening, as opposed to my clit, as obviously that’s where all of my wetness is coming from. In fact, I wonder if he even knows what a clitoris is? Either way, it’s so unusual to get eaten out this way, but as I said before, it’s incredible.

Me (as I take my right hand and run my fingers through his curly, light brown hair): “Oh, Honey Bear. This feels soooooooo good.”

Jake doesn’t respond or look up; he just keeps licking. My god, imagine me, as someone who went through so many years of having a husband who never wanted to go down on me, how amazing this must be. And it’s not just the physical sensation of being licked, but it’s also the satisfaction and self-assurance that comes with seeing someone enjoy the taste of my vagina this much. It makes me feel so sexy and so beautiful.

But let’s be honest, it also feels pretty damn good physically. But as satisfying as this is, I’m sure it could feel even better, so if this kid doesn’t yet know what a clitoris is, then I think I’m the perfect person to show him.

So I take my left hand, and I add it to the other side of Jake’s head, and I use both hands to not so subtly pull my young lover’s head up a few inches. I think I’m a little too forceful, though, as Jake’s face ends up above my mound, and he gives me the biggest grin, from ear to ear.

Jake (with a sheen of pussy juice glistening all over his face): “Am I doing a good job?”

Me (quietly): “Oh, Honey, you’re doing a great job.”

And then I immediately force his face back down to my pussy, but I make sure to line his mouth up with my clit. I’m mostly successful with my alignment, as Jake resumes his big, wide licks, but this time it’s directly on my little button.

Me (giving him some encouragement): “There we go…”

While this does feel good, and we’re getting closer, it’s still not quite perfect. And while I could probably give him some sort of verbal instruction, I try just to force the result I’m looking for. So I push through his curly hair and take a firm grip on his head, and then I shove his face down into me. This forces Jake to switch from his initial licking technique to more of a sucking sensation that gives me the constant pressure on my clit that I was desperately looking for.

Me (rather loudly): “Oooooooohhhhhh my god, yes. Ooohhhh… keep doing that…”

Holy shit, now this feels incredible! And I needed this so badly, after all the buildup from earlier tonight. But fuck, I think we might already be at the point of having too much of a good thing. Because if he keeps doing this, I’m going to cum, and I don’t want to orgasm just yet. Later on, I definitely do, but not now!

Me (as I use my two handfuls of Jake’s hair to forcefully remove his head from my clit): “Oh, Honey, give me one second here…”

While Jake hovers just above my vagina, he makes eye contact with me again, but doesn’t say a word. Fuck, he looks so adorable. And I love the fact that he’s doing whatever I say right now! Okay, time for a little more sucking.

I push Jake’s head back down into my vagina, and he seems to have learned what I like as his mouth heads straight for my clit again. This time, though, in addition to his lips pressing against the top of my vagina, I can also feel his tongue running circles around my magical little button.

Me (even louder now): “Ohhhh… fuck yesssss…”

Once again, this feels incredible, but once again, I’m already getting too close to cumming. I’m sure you’re like, but why don’t you want to cum? And the answer is, that’s just how I am. Maybe I’m weird, but the reason I don’t want to orgasm just yet is because I need his cock inside of me first, and we still haven’t done that. All the best orgasms I’ve ever had in my life have cum from a combination of fucking and clitoral stimulation at the same time, and tonight deserves nothing but the best, so that’s what I want to do.

And on that note, I do think it’s time to get on with the fucking. So I lurch forward, and I pick petite, little virgin Jake up by his armpits, and I pull him onto the bed with me.

Me (almost angrily): “Get the fuck on the bed!!”

Jake looks completely shocked, and to be honest, a little scared, but I just find that humorous.

Once he’s fully up onto the mattress, I force him down onto his back, and I aim his little, rock-hard three-and-a-half-inch boner that’s once again sticking straight up into the air. I have to hand it to Jake, as while he certainly doesn’t have the most enormous cock, or even an averaged sized one at that, holy shit, can this kid maintain his erections. I mean, not only has he spent the majority of this night stiff as a board, but he barely even needs any time after cumming to get hard again! It’s impressive.

But for all the boners this adorable, diminutive 18-year-old has had in his lifetime, I imagine this one is going to be unlike any before it. And that’s because for the first time, Jake’s tiny pecker is going to end up where it’s always wanted to go, inside a warm, wet pussy.

And as they say, there’s no time like the present, so with Jake now lying flat on his back, and his eyes looking up at me with great anticipation, I climb up over him, straddle his waist, and then use my right hand to guide his small, hard cock into my desperately awaiting vagina.

Me (as Jake’s penis slides in so fucking easily): “Ohhhhhhh… there we go… fuck… I needed this… oh, I needed this so badly.”

Holy shit, it really does feel incredible to finally be fucking this boy, and truth be told, his cock feels great. Who would’ve known, but his three and a half inches are doing the job just fine!

Ha, look at Jake’s eyes! He’s so fucking cute, and his eyes look like they’re going to pop out of his head. And his mouth! His jaw is extended, and he’s breathing so hard that I can see his chest rising and falling.

I lean forward and really start to grind on young Jacob’s midsection, and it feels oh so good. And now Jake puts his hands on my hips, as he gently slides them underneath my dumb oversized taco shirt that I probably should just take off at this point. But I’ll do that in a second, as I really want to focus on how good it feels to rub my clit against this boy’s plentiful pubes.

Me (as I gather my wits enough to form a coherent sentence): “How does it feel… to no longer be a virgin?”

Jake (with a slightly less serious and more relaxed look on his face as compared to when I first inserted him into me): “Oh my god… it feels so good.”

I lean forward a little more, which gives me an even better angle to grind. And I kid you not, this boy’s cock feels so good inside of me. I know I’m repeating myself, but I could not give two shits about how short it is. I know, I’m as surprised as you are! But this is fucking great!

Jake seems to be thoroughly enjoying himself, too, as he transitions into a huge grin. Although, based on where his eyes are focused, it looks like it’s my shirt that’s making him smile? I guess it is kind of ridiculous that I’m still wearing it.

Me (calling him out): “What’re you grinning at? Is it my stupid t-shirt?? I only put it on because it’s a mom shirt.”

Jake (still beaming): “No, the shirt’s fine. I like the shirt… it’s your boobs…”

Me (a little self-conscious now because I know they’re hanging down all floppy and clearly visible through my neck hole): “Yeah, that’s the one downside to this position. Sorry.”

Jake (subtly shaking his head): “No… don’t apologize. They look amazing.”

Me (as I can’t help but laugh at that): “Ha. If you say so.”

Jake (reiterating): “No. I like them… because they remind me… of when my mom would always tuck me in at night. She’d always wear a nightgown… and it was so loose… and when she’d lean over to kiss me, I could see her boobs like I can see yours now.”

Ha. It tracks that his mom would wear a nightgown. She’s my age, right? Who wears a nightgown these days?! And it’s also notable that we’re apparently taking a break from our roleplay, because Jake just referred to his mom as if she wasn’t here, instead of referring to me playing the part of her. I guess Jake actually losing his virginity was enough to snap us out of the pretend mother-son scene we had been playing up until this point.

Me (perfectly fine to refer to his mom as someone else): “So did you like being able to see your mom’s breasts like that?”

Jake (still struggling a little to speak as I continue to fuck him): “Yeah… I loved looking at them.”

I have to admit, yet again, this is kind of hot to think about.

Me: “Did you ever want to reach out and touch them?”

Jake (with a hint of desperation): “Oh my god, I always wanted to touch them. I wanted to grab them so badly.”

Me: “Well… you can touch mine.”

I assumed Jake might reach out with a hand and softly caress one of my breasts, but instead, as soon as I suggest that, he takes his two hands and shoves them through the neck hole of my shirt and firmly grabs ahold of both of my boobs.

Jake (with eyes closed now): “Ohhhhhh… they feel so good.”

Okay, my shirt needs to come off.

Me (as I start lifting my Mother’s Day taco t-shirt up and over my head): “Here, let me help you.”

Jake removes his hands from my chest just long enough for me to pull my shirt off, at which point his mitts head straight back to where they were before, firmly clamped onto my very modest tits.

Jake (seeming so appreciative): “Oh, Becca, your boobs are amazing!”

Wow. He just called me Becca. He really has moved on from the roleplay. How interesting! Not that I’m complaining, as fuck, this is just so great, either with or without me pretending to be his mom.

It’s so great, in fact, that I need to kiss this boy. Like, really kiss him.

So I lean forward and down, and as I do, I force his hands to come off my chest. Next, my lips head straight for his mouth, while he moves his arms around back to pull me in as well. Once our lips make contact, I immediately force his mouth open, and then I send my tongue past his parted teeth to meet his tongue on its own territory. Mmmmmmm. It’s so good!

I haven’t really made out with Jake yet, and so it’s kind of amazing to have our first passionate kiss happen while he’s already inside of me. But it makes me feel so connected to him. And I have to say, for a virgin, he has a pretty decent fucking rhythm going right now. And he also seems to be showing no warning signs of cumming either, which is fucking amazing, but probably expected given he’s already cum twice tonight. Kudos to me on planning this out perfectly! 😛

But as we continue to kiss and fuck, and his hands are still lovingly rubbing my upper back, I realize something. I’m actually pretty close to cumming! Yep, I think I’m well on my way. And why shouldn’t I be, as this whole night has been building and building to this incredible crescendo?

And don’t worry, there is no need for me to delay my orgasm any longer. I am ready to finally cum all over this sweet boy’s tiny, little, perfect dicklette.

And fuck, his tongue feels so good playing with mine. It’s been so long since I’ve kissed someone like this, and it’s such a great trip down memory lane. I have to say, he’s a surprisingly good kisser, too! God, I love the fact that he’s a virgin, though. He’s like the best possible combination, so young and innocent, but actually not half bad at kissing and fucking.

And I love thinking about how much he would masturbate, and how he’s been waiting for this moment his entire life! And oh my god, I still can’t get over the fact that he used to stick that miniature baseball bat up his own ass. That is still so fucking hot to think about.

But most of all, I can’t stop thinking about Jake and his mom. I don’t think I’ll ever fully come to grips with the fact that he has all these sexual fantasies about his own mother. It’s so crazy, and it’s so amazing that he actually told me about it. But I love that he did.

It’s such a huge turn-on to think about. The naughtiness, the taboo-ness of it. Fuck, I think I need to sit up again. Yeah, I want to cum while riding him. That seems like it’ll feel so amazing.

So I break out of our kiss, and I press my hands into Jake’s shoulders to lift myself. Now I’m back to sitting straight up, but I don’t stop grinding Jake’s cock, not even for a second.

Oh, I’m going to cum. I’m going to cum so hard. There’s no doubt about it. And you know what? It’s this idea of Jake and his mom that’s going to put me over the top. I can’t believe he would spy on her! And I can’t think he would watch his own mom orgasm, and then go back to his own bedroom and jerk off to that. And holy shit, I really can’t get over the fact that he would eat the crusties out of her dirty underwear! And then staring at her boobs in the nightgown. Fuck. It’s all so shamelessly perverted.

And I’m telling you, the mom knew. She probably still knows! There’s no way she doesn’t. She must’ve seen him through that crack in the door. Watching her. I’m sure she did.

And during those goodnight kisses? There’s no way she wouldn’t have seen his eyes peering into her nightgown. Jake wouldn’t have known enough to hide his blatant gawking. In fact, I’m guessing she’d see him staring at her hanging tits and just chuckle to herself at how horny her son must be.

And you know what? I bet she even knows he was going through her underwear. I mean, I know I’d notice something like that in a heartbeat. If my laundry was all askew from being rifled through? Damn straight I would, because again, I would bet anything that Jake wasn’t being meticulous about putting it all back how it was. And given everything else, I’m sure she could put two and two together and know immediate what he had been looking for in that pile of her dirty clothes. Fuck, that’s so hot in itself. It’s so wrong, but so good.

Me (with my eyes closed and hands now on Jake’s chest): “Oh, I’m gonna cum soon.”

Jake: “Oh, Becca, I want you to cum so bad.”

Me (fuck, I can’t believe I’m going to do this, but I am): “Oh, Jacobson… call me Mom. Don’t call me Becca.”

Fuck, now I’m the completely shameless one.

Jake (with immediate compliance): “Oh, Mom, I can’t believe I’m finally getting to fuck you.”

I grind his cock even harder.

Jake (continuing): “I’ve always wanted you more than anyone else. I’ve always wanted your pussy more than anything else. I’ve wanted it forever…”

Oh god, Jake. This is perfect.

Me (opening my eyes now to stare down at this adorable boy): “Oh, I’ve wanted it too, Honey Bear. Your cock is the only one I ever think about. I’ve always known you wanted me, but I could never tell you how much I wanted you. I’ve always wanted your cock in my pussy so badly.”

Jake (looking very serious now): “Oh, Mom, just cum. I want you to cum so hard on my cock. I want you to cum all over it. I wanna give you the best orgasm of your life.”

Oh, this sweet boy. His love for his mom. His desire to consume her vagina. To lick all of her juices. To suck on her dirty underwear. To have her stick objects up his ass. Oh, I wish I could watch Jake’s mom eat his asshole in real life. Fuck. I’m going to cum.

I grind harder than ever before, and yep, I’m cumming. And just as my orgasm commences, Jake sits up and completely surprises me by sucking my entire right boob into his mouth. It’s both shocking and fantastic, as I realize I haven’t had someone suck on me like this since my days of breastfeeding, so long ago.

And at this point, my instincts take over, and I grab hold of the back of Jake’s head with my right hand, while I squeeze my unattended left breast with my other. I continue to buck my hips frantically forward and backward on Jake’s perfect cock, and I cum so fucking hard.

Me (with a great sense of release): “Ohhhhhhhhhh my god.”

The stimulation of my clit, the feeling of his penis up and inside of me, all the forbidden taboo tales and desires, and now this one final element of Jake sucking so hard on my boob, he’s basically breastfeeding from me. It’s all so bizarre, forbidden, sweet, innocent, and extremely perverted.

It really is the best orgasm of my life.

And then it’s done. And I feel so unbelievably good. Euphoric even. But also exhausted. And slowly, my hips stop grinding, and my whole upper body collapses down onto Jake.

Me (with my mouth pressed up against Jake’s collarbone): “Oh my god… that was so incredible.”

Jake doesn’t respond, and considering I can’t see his face, I have no idea how he’s reacting right now. Is he happy? Terrified? Weirded out?

I give him a few more seconds to say something, but still, it’s just silence. My curiosity gets the best of me, so I summon every ounce of strength I have left, and I push myself up so that I can get a view of Jake’s face.

Ha. What a cutie. He has the absolute biggest grin I’ve ever seen, of pretty much anyone ever. In fact, he looks almost too happy to talk, which must be why he didn’t respond before.

Fuck, this makes me feel so good to see that he’s every bit as blissfully content as I am about what just happened. But as perfect as that orgasm was, there’s still one final element that needs to occur to make this an ideal night, truly.

In fact, just the thought of it gives me a second wind.

Me (mere inches from Jake’s face now): “Jacobson, I need you to cum inside of me. I need you to cum inside your mom’s pussy. And I need you to blow the biggest… fucking… load… of your entire life… inside your mom’s pussy. Can you do that for me?”

Yeah, fuck this idea of Jake and Becca having sex. I’m all-in on this fantasy. I’m Jacobson’s mom, and I need my son to fill me up with every last drop he has.

Jake (after nodding ever so subtly): “Can I be on top?”

Fuck yeah, you can. I use my newfound energy to lean back while pulling Jake’s upper body up off the bed. As we do this, we seamlessly flip ourselves over and immediately end up in a standard missionary position, almost like we’re a couple of acrobatic porn stars. Amazingly, I don’t think Jake’s cock ever leaves me during our whole transition.

And now that we’re in Jake’s desired position, he doesn’t waste any time in starting to fuck me, just as passionately as I fucked him a few moments ago.

With my back flat against my soft, pillow-topped mattress, Jake takes ahold of both of my hands and interlocks his fingers with mine. He then pushes them up above my head and pins them down forcefully against the bed. As he does this, he has a look of determination and desire on his face that I’ve never seen him have before, in the brief time that I’ve known him. It’s wonderful.

Me (staring right into Jake’s eyes): “Fuck your mom’s pussy. Fuck it so hard, Jacobson.”

Jake does as he’s told, and he immediately starts pounding me. His pelvis is slapping into mine, and with each thrust, he gives off the cutest little grunt. He’s working so hard that I’m starting to see little beads of sweat forming on the side of his forehead.

In fact, his intensity and rhythm are so impressive that it reminds me of a conversation I once had years ago with a male friend of mine, where this guy was trying to convey to me what it feels like for men to have sex. He explained that the typical motion of a man fucking, and specifically having sex in the missionary position, is one of, if not the most natural and instinctual movements a human male can ever make. He likened it to breathing, and he explained how even the very first time he ever had sex, for whatever reason, it felt like he had been doing it his entire life.

I actually think about that conversation a lot. While I have no idea if all guys would agree with his description of fucking coming as naturally as breathing, as I lie here and see firsthand how Jake is thrusting into me right now, I can’t argue against it. This boy is humping me with such vigor, passion, and competency that if it were any other skill in life, it’s hard to imagine him being this capable, the first time he ever attempted it. But I guess we have evolution to thank, because young Jacob, who’s never fucked anything in his life before tonight, is using his millions of years of caveman instincts to know precisely what to do to me, and to my pussy.

It’s so wonderful, but it’s also time for Jake to cum. I want him to cum so badly, and I want him to cum right now. I’m sure under normal circumstances, any virgin boy would’ve orgasmed long ago just from the grinding I gave him, doubly so when you consider Jake’s history of cumming from simply brushing up against the corner of a desk. 😛

But like I said, he’s already two orgasms in, so I may need to work for this one a little bit. The only catch is, with my hands pinned back as they are, there’s not much I can control right now, so I do the only thing I’m capable of to help facilitate this third orgasm. I spread my legs open a little wider, and I do my best to lift my hips off the bed to meet Jake halfway on every thrust he gives me. This definitely ups the impact of our fucking, and leads to even louder slapping noises every time our pubic areas collide.

Me (figuring I can also use my words to help the cause): “Oh, Jacobson, it’s been soooooooooo long. I waited my whole adult life for this.”

Jake’s mouth opens, and he looks like he might be close. He doesn’t say anything, though.

Me: “I haven’t had sex since the day you were born. I wanted to wait… for you…”

Obviously, I have no idea if that’s true, as all I know is that Jake mentioned his mom never seemed to date anyone. And to be honest, it seems extremely unlikely that she would’ve abstained from sex for that many years of her adult life, but who’s to say it’s not possible?

Jake (finally breaking his silence during his intense fucking of me): “Oh my god, Mom, are you serious?”

I smile and nod to confirm it’s true. Like I said, why not?

Jake (giving off a total O-face right now): “Ohhhh god…”

Me (let’s bring this puppy home): “Oh Honey Bear, this feels like it’s my first time, just like it is for you… Will you deflower me? Will you deflower my pussy that I’ve been saving just for you?”

And with that, my young, adorable 18-year-old friend gets to experience the sensation he’s always dreamed of. Not only is he orgasming into a warm, wet vagina for the very first time, but he’s living out his ultimate fantasy of cumming inside the pussy of his own mom.

It’s fucking incredible.

Jake finally lets go of my hands, and I use their newfound freedom to reach around back and grab ahold of Jake’s tight, little butt cheeks and pull him and his wonderful cock into me even harder.

Jake (with a low, deep moan): “Oh Mom… oh fuck… oh Mom…”

Jake’s whole body is spasming, and I can only imagine the amount of semen he’s currently depositing into my vagina. On the one hand, it’s his third time cumming, so it’s possible there’s not much left. But on the other hand, I saw firsthand, both in his underwear and then into my throat and out my nose, how much this boy can cum, so it seems totally plausible that this load would be just as epic.

Me (speaking softly as not to disturb Jake during his big moment): “Oh, Honey, just fill me up… fill me up with every last drop you have.”

God, I love this. Jake’s definitely reaching the end of his orgasm, though, and I can already feel myself starting to reflect on everything that just happened. Holy shit. What a night.

Me (as Jake starts to quiet down): “Shhhhhh… Hon… shhhhhhh…”

Yep. He’s all done. Jake collapses on top of me, completely spent, but with his penis still inside of me.

Me (starting to rub Jake’s back): “There we go, Honey… that was so special. You made your mom feel so good.”

How fucking insane was all of this? Can you believe that at the start of the night, I was all worked up, obsessed even, about the idea of Jake simply cumming in his pants! And somehow we went from that extremely innocent and naive act of prematurity, to one of the most taboo and perverted fantasies possible, a boy losing his virginity to his own mother.

As I switch to softly caressing Jake’s head, I continue to run through the highlights of this evening in my mind. On top of all the mom stuff, there was also the wonderful exploration of this 18-year-old boy’s butthole. I think what I loved most about that was that he had already been experimenting on his own with anal play, and I just helped him take it to a whole new level. I still love that mental image I have of him forcing that miniature wooden bat up against his bedroom wall. And while I didn’t get to see that for myself, I did get to explore the inside of his young rectum with my own finger, which was pretty fucking crazy in its own right.

Me (as I give Jake’s head a soft kiss while he continues to lie on top of me): “You’re sooooooooo sexy, Honey.”

Ha. And then there was that Angry Dragon I gave him. I bet he never forgets that for the rest of his life!

Jake (mumbling so quietly into my chest, it’s barely audible): “Thanks, Mom. I love you… so much.”

And then there’s that—the whole mother-son aspect. I’ll be the first to admit that I was initially skeptical of this entire roleplay. But holy shit did I end up embracing it by the end. I definitely surprised myself. But as hot as it was, and still is to think about it, I think it’s actually secondary to what I loved most about tonight.

Wait. Holy shit. Jake’s breathing just changed. It’s all rhythmic and measured. He’s fucking asleep! That’s so sweet.

Me (as I ever so gently rub his back again): “Shhhhhhh… there you go, Honey Bear. Get some sleep. You deserve it.”

Let this boy sleep on me all he wants. He can even sleep in me, as I’m pretty sure his cock is still inside my vagina. Although I figure it’s only a matter of time until it softens up enough to slip out, at which point I’m sure my sheets are going to get soaked. Oh well!

Ha. That reminds me, I still haven’t moved Jacob’s laundry load to the dryer. They’re definitely going to be sitting there overnight! 😛

But anyway, where was I? Oh yeah, about to explain what I loved most about tonight. You know what it was? I loved the confessions.

I think the very first one took place last weekend in front of his dorm, when Jake confessed that he actually did come in his shorts, just as all of his friends had surmised. I loved the vulnerability Jake showed when he told me that, not to mention the embarrassment he must’ve endured both at the time it happened and when he rehashed it to me.

Now, obviously, the biggest confession of all was everything to do with his mom. But it wasn’t just the bombshell that he had sexual feelings for her, but also all the little extra confessions along the way. The spying on her masturbating. The watching of the door while he anally masturbated, hoping that she would catch him. The licking and sucking of her dirty underwear. Even the peering at her breasts down her nightgown. Every single time he admitted something new, it just turned me on more and more.

I sweetly give Jake’s curly brown head another kiss, and now he’s full-on snoring on top of me.

Last week, I came to grips with the fact that not only do barely legal boys turn me on, but that the more innocent they are, the better. Basically, bring on all the 18-year-old virgins you got!

But this week, I’ve discovered yet another layer to that fetish. And it’s one that I probably couldn’t even have told you existed, let alone what the name of it is. But I love, love, love this idea of these young, innocent, virgin boys confessing all their greatest secrets and desires to me. And obviously, as you can tell from tonight, literally anything is fair game.

Give me your weirdest masturbation stories. Your biggest crushes, no matter how forbidden they are. Tell me what you’ve always wanted to do to a girl, and who you want her to be, and I’ll become her. Tell me what you want this girl to do to you, and I’ll do it all. And if you like it, I’ll do it all again.

Because what really turns me on the most is turning you on. And it’s hard to imagine anyone getting turned on more than a shy, nervous, horny, perverted, 18-year-old virgin who has secrets he’s scared to death to tell anyone. But there’s no need to be scared, at least not with me. Because not only will I not judge you for your deepest and darkest fantasies, but I’ll do everything humanly possible to make all of them come true.

The End.

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