Jake’s Dilemma – Mom’s POV

TPK (The Pirate King)

Jake’s Dilemma

My husband and I filed for divorce, and rather than mope around I decided to move closer to my sister Jackie’s house for moral support. I didn’t get as much as I hoped to from my ex-husband, but I did get Jake. Jake has always been a great kid and after seeing the way his father and I fought, I’m not surprised that he wanted to keep living with me. After we got settled into our new house, Jake took note of our swimming pool. Our last house didn’t have one, and he couldn’t wait to try it out. So, we changed into our swimsuits and went for a swim. I had on a bikini, that at this point, was getting close to being a little small on me. I had to be careful wearing it around Jake, didn’t want him to suddenly get the hots for step-mom. I also didn’t want Jake to get sunburned because he would probably whine about it for days, so before he went in I applied sunscreen all over his body. We had a good time thanks to the slide and the diving board at our pool it was quite nice.

After we got out of the pool, I called my sister Jackie to let her know I was coming over for a surprise shopping spree. I left my message on her voicemail and was about to head out. But, before I left I made sure to set the rules for the house, with Jake. No junk food, no leaving the house, and no swimming by himself. Jackie canceled our plans though because she caught a nasty cold. I did go over to her house to wish him well. After that, I left quickly because I did not want to catch her cold. After I pulled into my driveway, I went inside and didn’t see Jake anywhere. Then I noticed the back door hinge lock was off.

If Jake is in the pool I am going to blow up at him.

“JACOB MICHAEL PETIT! What Are You Doing?”

I said because as I looked down across the pool, I could see him standing in the water.

“Mom! I-I thought you were going out with Aunt Jackie…” Jake announced with a very surprised look on his face.

“Your Aunt Jackie called me on my cell phone and canceled. She’s feeling sick today. Now, do you want to explain to me why you’re swimming when I clearly told you not to?”

“Mom, I-I’m sorry. I was just…” Jake stammered out.

I just know he’s going to come up with some excuse about why he’s in the pool, I was beyond angry, so I shouted at him in my scary mother voice.

“Get out of that pool this instant!”

Jake seemed very hesitant to get out of the pool, so I pressed him again.

“What are you waiting for?”

“Can you hand me my towel, please? I’m not wearing anything.” Jake muttered with an embarrassing creak in his voice.


I didn’t know what to say, but I was still upset he broke a rule only mere minutes after I explicitly told him not to.

I said through gritted teeth, “Get out of that pool! Right—Now!”

I was confused but still very much angry. I was NOT going to be bringing Jake his towel.

Besides, I’ve never seen him naked before, I wonder what he actually has down there…

Jake seemed to ponder if he had any other options for the moment, but reluctantly he went over to the ladder. Jake gripped the sides of the ladder and pulled himself out of the pool – naked and in full view of me. I watched as he climbed the ladder and stepped up onto the patio. Before he had a chance to cover himself with his hands, I turned around, grabbed the towel off of the chaise, then turned back and tossed it to him.

Mom’s inner monolog: Oh My God. That’s his penis? It’s—It’s like nothing’s there for a dick, just a small part of the head can be seen, so he has maybe a half-inch in length right now. And SKINNY it’s as thin as my pinky finger, Holy shit Jake. I would feel sorry for you if I wasn’t pissed right now.

“Dry off, get dressed, and then go to your room. I’ll deal with you later.”

I immediately went back inside, I was having a hard time keeping a straight face when confronted with Jake’s baby sized penis. As soon as I was in and Jake was still drying off, I started giggling, then I laughed.

I had to call Jackie and talk to her about this. I went to my room to get privacy in case Jake came inside soon.

“Hey Susan, what’s going on?” -Jackie

“Jake… When I came back to the house, he was in the pool even though I explicitly said not to swim without someone else there.”

“That’s way dangerous!” -Jackie

“Yeah, but that’s not the best part of this story… he was swimming au naturel!”

“Seriously?” -Jackie

“Yes, completely naked. I don’t know what to do…”

“Well, you need to punish him obviously.” -Jackie

“Yes, but I’m not sure how… I’ll figure something out.”

“Well, if you come up with a good plan, I’ll help out if you need, Susan.” -Jackie

“Oh, and again, not the best part yet still… When I saw Jake’s penis, it took everything I had in me to not just start laughing out loud. That was the most hilarious thing I’ve ever seen on a grown adult.”

“Was the water cold or something?” -Jackie

“No, our pool is heated… I think Jake just has a really, really, tiny penis.”

“Oh my god, seriously, how big did it look?” -Jackie

“I’m pretty sure my pinky finger is wider than his penis was, and I’m not even sure if it was an inch long.”

“Oh my god, I would have loved to have been there, I probably wouldn’t have as much restraint on my laughter though.” -Jackie

“Well, I think you should come over to my place later tonight after Jake goes to sleep. I have some questions about this situation, that I need answers to, haha.”

“Will do! I’ll shoot for 11:30, sound good?” -Jackie


After hanging up with Jackie, I went to go check on Jake. I’m still not sure how to punish his behavior, but I’m going to figure it out when I’m in there with him.

After I walked into Jake’s room I sat down next to him on the bed.

“First of all, I want to tell you that I’m sorry for yelling at you. I want you to understand that I make these rules for your own safety. The pool is far too dangerous for a little boy to be playing in when nobody is around.”

Jake was about to interject, I could see in his eyes he wanted to say that he’s not a little boy, but he was definitely scared to confront his penis issue with me.

“As punishment for swimming alone, you’re to have no TV and no video games for one week.”

Jake’s inner monolog: That’s totally fine by me. I’m also way glad she didn’t say anything about my penis. God, I hope she didn’t actually see it.

“Now, Jake. Would you like to tell me why you broke the rules and went swimming? And does it have anything to do with the fact that you were au naturel?”

Jake began to speak “Mom, I’m sorry I broke your rules. And I promise I won’t do it again. I went skinny dipping when you weren’t here because I was afraid you’d be offended. You see, lately, I’ve become kind of a naturist. It just feels free and natural to swim nude. I did it all the time when I lived with Dad, and it was no big deal, and I just thought I could keep doing it here. But I didn’t want to offend you. That’s the only reason I broke the rules.”

“And that’s really why you were nude out there?” I looked him dead in the eyes, as I asked, to see if he flinched.

“Yes, Mom. I swear. I wasn’t trying to be bad.” Jake whispered to me with his saddest puppy dog face on.

Mom’s inner monologue: Aha! I’ve got it. Jake is obviously lying here, I know that sad face he uses anytime he tells a lie. I know exactly how to punish you now though, Jake. After this, I doubt you’ll ever disobey me again, haha.

I nodded and smiled. “I must admit that finding you like that gave me quite a shock. I wasn’t sure what to think. But I talked it over with your Aunt Jackie,”

I could see Jake’s face get bright red. Maybe he thinks I told Aunt Jackie about his tiny penis.

“And she actually suggested that it might be something as innocent as what you just said.”

“Really?” Jake piped up a little louder this time.

“Well, she said it was either that or that you were some kind of pervert, but I know that you’re a good little boy. And she did remind me of a few things. Like when we were little kids growing up in France, we would swim nude all the time. And even after we grew up, we would sometimes frequent the au natural beaches. And it was never sexual or perverted. It was free and natural and accepted. You probably don’t remember this, but we even took you to the au naturel beaches more than once when we still lived in France. You couldn’t have been more than 4 years old, but you loved running around naked with your little pee-pee jiggling around.”

Mom’s inner monologue: Ha! I knew it; he’s really embarrassed by his penis size. I just saw his face change to pale terror and then bright red again when I used the phrase “little pee-pee”

“Anyway, all I mean to say is that I shouldn’t be surprised that you found your way back to a naturist lifestyle. Or that your father would approve – that man loved being naked.”

Jake’s inner monolog: I couldn’t believe it. She was buying my story. She actually thought that I was a naturist and not a pervert. I just had to stick to my story, and everything would be fine.

“But let me ask you this,” I continued. “Were you embarrassed that I saw you naked?”

Just as I figured, Jake piped quickly with “No. I wasn’t embarrassed.”

This time, I made sure to look him directly in the eyes, and I had a full teeth-bearing grin, I was still suppressing my laughter, especially with what I was about to ask him next.

“It didn’t bother you that I saw your little dingaling?”

I saw it; Jake’s eyes went super focused, as he realized what I said.

There was a 5-second pause before Jake said anything else.

“I was scared of being punished, but not embarrassed. Dad says that being nude is a completely natural thing and not something to be ashamed of. Isn’t that true?” he asked, trying to sound innocent. He had on the sad puppy dog face again and was staring me in the eyes.

Mom’s inner monolog: Just you wait, Jake, you’re going to get all the punishment you deserve for breaking my rules AND lying to me.

“Yes, Honey. That is true. And that’s a very mature and healthy attitude to have. Thank you for being honest with me. I feel a lot better about your reasons for breaking the rules. Your punishment for swimming without supervision still stands though – no TV and no video games for a week. And I want you to stay in your room for a while, and think about what you did, and why these rules exist. They really are for your own safety. I’ll come and get you when lunch is ready.”

With that, I gave Jake a hug, said that I loved him, and left, closing the door.

Before I could walk away though, I heard an audible sigh from Jake’s room.

He must have been expecting a lot worse. Oh, I’ll crank his embarrassment up a notch, especially if he’s not willing, to be honest with me.

For now, though, I began to get lunch ready.

I know Jake’s a teenage boy, so I had a pretty good idea that he was jerking away on that tiny penis. For a moment, I pondered how he had to jack something so small… I just assumed in my mind it was one finger and his thumb. I snort laughed out loud a little bit when I thought about it. Jake’s 18, but he’s NOTHING like the men I dated at that age. The smallest one was probably still a solid 7 inches and thick and I could wrap both hands around it and still have room to suck him or jerk him.


Jake collapsed back on his bed with his heart pounding in his chest. He thought to himself

“I did it. I had gotten away with it. She actually believed my story about being a naturist.”

I changed into my own bathing suit. This time it was my bikini, damn, I look pretty good in this. After all, I am only 28, I married Jake’s father when I was just 18. I’m very thin with breasts that I think are ample for my size. I have short brown hair and brown eyes and I have a tan over… mostly all of my body.

It was only 2:30 and I figured I could get Jake to go swim again… I can definitely put his little “nudist claim” to the test.

I called Jake downstairs.

He came down, eyeballing me, he asked what was up. I replied, “I have a surprise for you. Come outside.” With that, I turned and went out the back door. As I turned I know Jake probably got quite a shock. I was wearing my thong bikini. I didn’t mention my ass earlier, did I? Oh, it’s tan and quite rounded. Jake followed me out the door not knowing what else to do or what to say. I made sure to flex and un-flex my ass as I walked, swaying my hips on purpose. I bet I can get Jake nicely worked up like this.

I glanced back over her shoulder to make sure Jake was following and caught him staring slack-jawed right at my ass. Jackpot, I thought. I smiled slightly at Jake, to make him think I didn’t mind, then turned back and continued. As we got to the chaise’s I turned and sat down on one of them and started speaking.

“I don’t know if you’ve noticed the fences back here. They’re called privacy fences. They’re quite tall and block the pool area from the view of the neighboring houses. Well, I had these fences installed so that I could sunbathe and swim topless.” With that, I reached behind my back and untied my bikini top. I then pulled the top off and put it down. I could see the ogling expression on Jake’s face.

Mom’s inner monolog: Oh, yes, Jake, I have your perverted little ass trapped now, don’t I?

Jake was less than 3 feet away from me, and my boobs were completely exposed to him. He couldn’t take his eyes off of them Thanks to my own nude sunbathing, my boobs were completely tanned. My nipples were standing out firm, like little pink pencil erasers.

Even though I was doing this to catch Jake being a pervert, his staring did make me blush, and I smiled as I continued. “It’s not something that I’ve done since I was much younger. Not since we moved to the US, in fact. But since moving to this new house, I’ve really enjoyed the freedom of swimming and lounging around topless. I must admit that when I found out that you were going to be staying with me, I figured that I’d have to put a stop to that. For one thing, I didn’t want to offend you or make you uncomfortable, but the bigger reason was that I was afraid I’d be far too embarrassed.

Nobody has seen me topless in quite a long time. Even when your Aunt Jackie comes over to swim, I wear my more conservative one-piece suit. That’s why I asked you earlier if you were embarrassed by me seeing you nude. Your mature response made me realize that maybe I shouldn’t be so ashamed of my own body. If you don’t have a problem with people seeing your little dingaling, maybe I shouldn’t be so modest about my little boobies.”

Mom’s inner monolog: At this moment, I saw Jake’s delighted face twist down a little bit. His uncontrolled smile flat lined. Yep, he can tell where this is going. I can practically see the frog forming in his throat and the embarrassment burning into his eyes. I continued speaking as I relished his forthcoming embarrassment.

“And so I decided that you can continue your naturist lifestyle here. This is your home now too, Jake, and I want you to feel at home. I want you to feel free to do what you want to do, and know that you won’t be offending me.”

Jake’s inner monolog: I still hadn’t completely processed seeing my very first real bum and my very first real set of boobies. And now it was starting to sink in that my stepmom was giving me permission to be naked in front of her. Why did I have to say that it didn’t bother me? I realized (far too late) that what I should have said was that it did embarrass me. I could have said that I was OK being a naturist around my dad because he’s a guy. I could have said that it was embarrassing having a girl see me. She probably would have accepted that as a valid answer, and that would have been the end of the entire incident. But no, like an idiot, I had said that it didn’t bother or embarrass me at all being naked in front of her. And she had believed me. I couldn’t change my story now. I was stuck with it.

“Well,” I said. “What are you waiting for?” I asked as I smirked unwavering at Jake.

“What? You mean now?” Jake asked with his own cheeks beginning to get rosy.

Jakes’s inner monolog: She couldn’t mean that she wanted me to get undressed now, could she?

“Of course now, silly. Dinner isn’t for a few hours. And I know that you don’t have anything else to do – no TV and no video games, remember?” I giggled out at Jake, as I knew I was grinning so hard the dimples in my cheeks were showing.

Jake was trapped. I was just going to sit there waiting until he took his clothes off. I stared intently as he started taking his shirt off. I could tell his heart was pounding. When his shirt was off, I took it from his hands and tossed it on the chaise next to my bikini top. I didn’t want him to be able to let it cover any of himself up, ha! I tried not to laugh as Jake fumbled with the button and then the zipper of his shorts, as they dropped to the ground he stepped out of them. He was down to just his adorable mighty whitey underpants. I made sure to give him a nice smile of encouragement. (Really I was just trying very hard not to laugh out loud in his face.)

I stared directly at his crotch as he hooked his thumbs into the elastic waistband of his underpants, and quickly slid them down his legs.

He was trying to pretend he wasn’t embarrassed, but here, I could see his tiny pencil thin, toddler length penis… His face was crimson red.

He was avoiding looking me in the face. I’m glad he was, because my smile cracked open, and I almost started laughing. I had to bite my own lip to keep my mouth closed.

He tried to turn and run for the pool immediately after I got a brief look at his meager genitals.

“Jake,” I shouted. “Aren’t you forgetting something?” I made sure to ask with an innocent tone to my voice.

Jake stopped in his tracks, with his milky white butt completely exposed. He looked over his shoulder, his body shielded his groin from my view. So, I reached into my beach bag and pulled out a bottle of sunscreen.

Mom’s inner monolog: Bet you forgot all about this, huh Jake? Mommy’s secret weapon. Don’t worry darling, I’ll make sure you don’t get any nasty sunburn on your naked little butt or your pale little pee-pee. Oh, I was trying to behave in a motherly way… but I was absolutely cracking up inside as I saw Jake’s face, as soon as he realized I was holding the sun block, he had a look of sheer terror.

Jake’s heart sank. He tried to talk his way out of it. “Come on, Mom,” Jake said trying his best to keep the fear and shame that he was feeling out of his voice. “It’s not even that sunny out.”

“It’s sunny enough to get burned. Get that little butt over here, mister.” I said authoritatively, I also made sure Jake knew I was looking right at his naked butt.

Jake was so embarrassed he backpedaled all the way to me. He didn’t even turn around to walk, haha. He backed up so that he was only about a foot in front of me, so I got to work and started applying the sunscreen to his shoulders. Jake shivered as I touched him.

“Sorry. I guess it’s a little cold”. I apologized, as I continued rubbing it into his skin.

Jake’s inner monolog: It wasn’t the temperature of the lotion that made me shiver, it was the knowledge that someone was touching my bare skin while I stood completely naked and exposed in front of her.

“That’s OK,” Jake croaked out.

Mom’s inner monolog: I’m going to take my time applying Jake’s sunscreen, for one thing, so I can savor this… But also because I need a few minutes to compose myself before Jake turns around and sees my face again. I don’t want it to be obvious to him, that I’m secretly laughing to myself about him and his less than pinky sized excuse for a dick.

I worked my way down each of his arms and then squeezed out more lotion for Jake’s back. Again, he shivered. I moved lower on his back. I bet Jake thinks I’ll let him do his own ass, nope, I began gently massaging his nude cheeks. I chuckled as I said, “Well, it’s obvious that you were telling the truth about spending a lot of time au natural lately. Your cute little derrière has quite a nice tan.” (Jake’s butt wasn’t too tan, I just wanted to make him think I was still falling for his little ploy.)

I made sure to VERY thoroughly apply the lotion to his butt. I even thought about reaching around and doing his front from here, but I decided against it. I want to look directly at his little pee pee before I start applying lotion there. I can’t wait to make him hope I’ll let him do his own penis… Then I’m going to take all that hope away and look directly at him naked, oh man he’ll be mortified.

While I thought, I began working my way down each of his legs. Jake shut his eyes and prepared himself for me to tell him to turn around.

Mom’s inner monolog: Not today Jakey boy, I’m not giving you a chance to get out of this part. I composed my face as best I could to put on a happy mother face, and not a college girl about to laugh her ass off. It was very hard to choke down these laughs, but I was prepared to do it, as I got ready to turn Jake’s whole body around.

I could tell I put Jake slightly off balance, but I grabbed him solidly at his waist and I spun him around so his little dick was mere inches from my face. Jake’s eyes were closed at first, but as he opened them, he realized I was now looking at his naked body and there was nothing he could do. I maintained my tight hold on his waist, so he couldn’t get away from me even if he wanted to.

I watched for a moment because I wanted to see if Jake would be more embarrassed about his tiny dick, or so much of a pervert he was just going to stare at my boobs again… Jake’s eyes went straight to my naked boobs.

I’m glad Jake knows nothing about women, or he’d be able to tell from how hard my nipples are, that I’m turned on right now. Jake himself isn’t turning me on, but the idea of humiliating him like this, completely naked… Now that was actually causing me a little bit of erotic excitement. I always did get a small kick out of humiliating big, strong, men. Especially when they had the type of little weakness Jake does… Right in between their big, strong, legs… A teenie, tiny, fragile, pinky sized flesh rod, pretending to be a penis.

As Jake’s eyes gazed up from my boobs to my face, I made sure to be looking right there between his legs, at his PATHETIC excuse for a dick.

Mom’s inner monolog: OH MY GOD, I CAN’T BELIEVE THIS! He has NO PUBES, his dick is LAUGHABLE, this can’t even really be a solid inch long? Can it? His balls are practically non-existent. How is he 18? No girl is ever going to want to fuck this. I can’t believe I’m not laughing at full volume right at his tiny penis RIGHT NOW.

Jake could see that I was looking right at his exposed penis. It was less than a foot in front of my face. Honestly, as close as he was, I still feel like I needed to lean in a little more to be able to make out all the detail. I had a perfect and unobstructed view. I’m glad I can finally get a perfect view of this before I had only caught brief glimpses as Jake had climbed from the pool, and later pulled down his underpants. I was taking in every detail with a smirk on my face. I knew both my dimples were apparent, this was as wide as I could smirk before laughing and losing it. I bit my lower lip to keep from laughing again. I could see that Jake had no pubic hair at all – not even peach fuzz. I could see how small and tight Jake’s balls were. And I could see his SKINNY, TEENIE, TINY, LITTLE, MAYBE ONE INCH penis in full humiliating detail.

Mom’s inner monologue: Is this one inch? Shit, maybe it’s less than an inch? Possibly barely a little longer than one inch? I can’t decide, I really need to measure this to be sure, but seriously… I can understand you being embarrassed Jake, but it’s not cold out… It looks like it’s hanging so it’s not shrinkage… Jake’s normal flaccid size, is basically just one inch long, holy fuck. Even if you’re serious and you like being a nudist Jake, I will MAKE SURE, you are fully embarrassed by this.

I could see that it leaned very slightly to the left. (If you can call it a lean.) I could see how the circumcised head was a different color than the shaft – like a tiny pink army helmet on the world’s tiniest soldier. There could no longer be any doubt – I now knew exactly how underdeveloped my little boy was. After staring right at Jake’s hairless pathetic little penis for about a half a minute (Though I’m sure for Jake, it felt like an eternity.), I finally spoke.

“It certainly looks like your Aunt Jackie was wrong about you being a nasty pervert.” I looked up at Jake’s face. I made sure to make full eye contact. He was crimson red, I’m going to pretend this is normal, but I want you to know Jake, that I see this. As I was making eye contact, I raised my eyebrows slightly, he raised his eyebrows in response, and he gasped in a small amount of air. Good, he sees me looking. I gave him a knowing smirk, though if he’s delusional he probably took it as an encouraging smile, and then I looked right back at Jake’s tiny penis again, knowing that he could see me looking right at it.

Mom’s inner monolog: Yes Jake, we both see it. It’s FUCKING TINY. I’m glad I smirked right at your face before I looked back at your pathetic dick. This is what you get for lying to me. This is what you get for breaking my rules. Unfortunately for you, however, this wouldn’t be nearly as bad… If you didn’t have, an itty, bitty, teenie, tiny, small, little, FUCKING TINY one-inch penis.

Jake’s inner monolog: I knew exactly what she was talking about right away. She was referring to the fact that I didn’t have a boner. The truth, of course, was that the only reason I didn’t have a boner was that I had just jerked off in my room about 10 minutes before this. If I hadn’t done that, I have no doubt in my mind that my penis would have sprung to attention the second I saw my stepmom turn around in her thong. It would have stayed hard all this time (that was of course if it didn’t explode cum all over the place before now – either from seeing my stepmom’s boobs or from her massaging my bum). I don’t know what she would have said or thought if I did have a boner, but thankfully I didn’t. She was staring right at a very soft (as well as very small and very bald) penis.

Jake tried to act like none of this bothered him and that he didn’t know what I was talking about “What do you mean, mom?” he asked innocently.

(Pfft, I’m not going to explain my surprise at your lack of erection. From now on, you’ll be my “little boy”. I’m sure you’re dying inside from embarrassment, but here let me say this just to embarrass you a little more…)

I replied, pretending to look embarrassed by his question: “Oh. Nothing honey. I just mean that you look like a very good little boy.”

I grabbed up the sunscreen bottle again and squeezed more into my hands. I put some on Jake’s face. Then massaged my way down his chest, to his stomach, and stopped right above his pathetic, tiny penis, before reaching for the bottle again.

“I can finish up,” Jake piped up, trying to keep mine from feeling his little penis with my own fingertips.

Mom’s inner monologue: Ha! Like I’m going to let you take this away from me, nope, sorry Jake. Mommy’s going to feel your little pee-pee with her thumb and index finger for long enough to cover the whole thing with sunscreen, probably just one second, hahaha. I wonder if he’ll cum?

I squeezed a bit more into my hand, then put the bottle down as I rubbed my hands together, and said, “Now honey, we went over this yesterday. I’m afraid you’ll miss a spot if you do it yourself. And I don’t want you to get burned. I especially wouldn’t want you to get a sunburn on this cute little dinky of yours.” I let out a small chuckle as I said that last bit. And with that, I reached out and gently massaged Jake’s entire groin area. My hands were slippery with the lotion, but I was very thorough, massaging his tight little balls with my fingertips, and taking special care to wrap my slick index finger and thumb around the base of Jake’s skinny penis and pull – tugging and stretching it as my two fingers slid right up to the circumcised tip.

Mom’s inner monolog: I tried to stretch his tiny penis with my fingers to see it’s stretched length since this often indicated fully erect length according to things like the Kinsey study. As best I could tell… Maybe 2 inches full stretched? Fuck, not only is Jake pathetically skinny, but his dick is probably at best a third of the average length. Haha, I can just imagine Jake trying to pull this out on some college girl, as she laughs. I’d bet the smallest dick she’d ever seen is still going to be about twice as big as Jake’s. In length AND width. Ha.

I did that a couple times with each hand.

Jake’s inner monolog: No one had ever touched me like that, and it felt incredible. Once again, I was grateful that I had just jerked off – If I hadn’t, I’m sure I would have squirted cum all over my stepmom right then and there. Even so, I felt some stirrings in my penis, and I knew that if she continued, I’d get a boner in a matter of seconds. But thankfully she stopped, gave my privates one last look of approval, and then turned to lie down on the chaise.

“Do me a favor, honey, and get my back for me please,” I spoke to Jake as I lied down on the chaise. (I needed to face away from him for a few minutes again so that I could regain my composure. I can’t believe I just personally handled a dick the size of a sharpie top, but thinner…)

Jake just wanted to jump in the water at this point, but he had to do what I asked. At least we weren’t making eye contact, so he can’t see that I’m trying not to laugh still. Jake picked up the bottle of sunscreen and started to rub it into my back. While doing this, of course, Jake’s eyes drifted down to my ass, I’m sure.

Jake’s inner monolog: For having such a skinny frame, she certainly did not have a flat bum. I guess you’d call it a “bubble butt” – two perfectly round cheeks. The string of her thong was lost between them. I finished her back. Then my mom said, “Would you mind getting my derrière, too? I wouldn’t want a burn.”

Jake squeezed out some more lotion and got to it. He couldn’t believe the situation he was in. Here he was standing naked outside, and massaging perfect nude buns he could imagine. For the moment, it didn’t even matter that it was his own stepmother. He was just enjoying the sensation of touching those firm round cheeks.

Mom’s inner monolog: Enjoy this as much as you can Jake, I doubt you’ll be touching many girls naked after this.

Jake probably spent too much time rubbing, and only stopped because he noticed his penis springing to attention. Jake prayed that his stepmom wouldn’t roll over and see it. Jake quickly applied lotion down the backs of her legs, and then said: “All done.”

“Thanks, honey. I can get the front.” And I started to roll over.

Jake’s inner monolog: I couldn’t let my stepmom see me with a boner (especially a boner that I got from rubbing her bum). So I quickly turned away, saying “No problem.” I ran to the pool before she could stop me again and jumped in.

(I saw Jake scamper off quickly to the pool; I figure he had probably gotten erect from putting lotion on me. I didn’t care right now, I decided to get the sun I needed for my tan, and ignore the little pervert for the moment.)

Jake was very relieved to finally have some sort of cover. Jake just wanted to stay in the pool forever (or at least until his boner calmed down). Jake swam to the ladder so he could grab hold of it and catch his breath. His heart was beating a mile a minute, and he was afraid he might have a heart attack if he exerted myself too much. Therefore, he grabbed hold of the ladder and just floated while he tried to collect his thoughts. Jake couldn’t believe what had just happened. Now that he had a minute to think about it, the enormity of what had just happened was starting to sink in. His stepmom had touched his penis! Just thinking this made him very aware of how hard he still was.

Jake looked up to his stepmom to see her sitting up in the chaise.

I was rubbing lotion into my legs, as I looked up very discretely, I could see that Jake was eyeballing me from the pool. The way I was bent over, my boobs were pointing straight down. They were even pointier now, the way they were almost hanging down. And they were jiggling and swaying a little as I applied the lotion to my legs.

(I bet Jake’s got a tiny little hardon in the water, I guess at some point I should go over there and have a look myself.)

Jake couldn’t pull his eyes away. As Jake floated there he drifted a bit to the side and felt a current on his hip. It was the same warm water jet from earlier. Jake knew what he was doing was wrong, but at that point, after everything that had just happened, he couldn’t help it – he floated over a few more inches to position his tiny penis right in front of the water jet. Jake let the warm current caress his puny boner as he stared at his stepmom’s pointy little boobies jiggling as she rubbed her legs.

(That little twerp, he’s positioned so his crotch is lined up with the water jet… Now it makes sense…)

As I finished my legs and sat up to start on my stomach, Jake knew he couldn’t last long. The feeling of the water plus seeing his stepmom almost naked, combined with the memory of those slippery fingers massaging his soft little penis was driving Jake crazy. My hands moved up and up my body, and soon I was rubbing lotion into my boobs.

(Oh my god, is Jake cumming?)

Jake couldn’t stand it anymore. He felt himself start to lose control. Just then, I looked up and (still rubbing my boobs) looked right at Jake and gave him a shy little smile. Jake’s eyes rolled back a little, and he bit back the urge to grunt as he exploded into the water. Jake tried to cover up the involuntary bucking of his hips by pushing back from the ladder and splashing with his arms. Jake prayed I didn’t notice.

Mom’s inner monolog: Oh my God, did Jake just cum in the water while looking at my boobs? This sick pervert. I’m going to find a way to get him back for this later tonight. But what can I come up with that will mortify him even more than this…?

“How’s the water?” I asked, pretending to not know what was going on.

“It’s great. Really warm, but refreshing.” Jake responded swiftly.

I smiled and then put on my sunglasses and laid back to get some sun. Jake stayed there treading water, realizing with mounting shame what had just happened. He had cum from looking at his stepmom’s boobs and from thinking about her touching his tiny penis with her index fingers and thumbs. And she had been looking right at him when he came. The fact that Jake was underwater, and she couldn’t actually see it wasn’t helping. Jake assumed she was being very understanding and supportive of what she thought was a healthy and natural lifestyle choice, and that he had gotten off on it. Jake had never felt like such a pervert in his life.

Mom’s inner monologue: I feel like ordering pizza… Amy works at the closest pizza place… Oh… I have an idea. Jake, you are so fucked for being a pervert and cumming, to my boobs with that water jet. You have no idea what’s in store for you, you baby dick loser.


The End.



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