Humiliating My Stepbrother: Part 3
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by firstname.lastname@example.org ©2013
It was hard for Jimmy to look me in the eyes after our most recent and most painful incident, but I acted like we were closer than ever. I still wanted him to see me as his well-intentioned protector, even after all that, and not to withdraw and shrink away after what happened. Besides, being with him was a constant reminder of his debasement, and it was fun to make him so uncomfortable with nothing my than my presence.
I eased up on my direct humiliation of him, wanting to reserve my harshest words for when he was in the throes of the most delirious arousal. Often, I would couch my casual humiliation in the form of innocently curious questions.
Sitting with him just before bed, I would lay my head on his thighs. “You had gym today, didn’t you Jimmy?”
“Yeah, Tuesdays and Thursdays.” There was a bit of a stutter to his response already, my contact alone enough to unnerve him.
“You have to change into your uniform before gym class, don’t you?”
“I was wondering sweetie, does it embarrass you to get naked in the locker room at school? And in the showers? I mean, knowing how much smaller you are than the others, that has to be tough, right?” I was dressed in a tight, basically modest ruffled blouse, but laying at the angle I was, I knew Jimmy could see just a hint of cleavage down my shirt, the bare skin so tantalizingly close.
He trembled slightly. “I just try to be quick,” he sighed. “And to not think about it.”
“Aww… I bet. Have the other men there ever laughed at boys like you? High school guys can be so cruel, do they ever make fun of you for having an undersized, underdeveloped little penis?” I ran my palm idly over his clothed dick.
“N-no. Um… I guess I try to face away and hope they don’t look.”
“Do you ever sneak a peek at the other guys, Jimmy? Ever get curious how much bigger, longer and thicker than you, most guys are down there?”
“No! I wouldn’t do that. I just I just try to be quick.”
“That’s good, sweetie. I know it would really hurt your feelings to see for yourself how very tiny you are compared to normal guys. I’m sure it’s better for a boy with such a baby stub to not try to compare himself. Although” I giggled, and began tickling the undersides of Jimmy’s balls lightly. “Although I have to admit it would be so funny to see your adorable little pee-pee right next to a real cock.” He blushed so hard. “Not to be mean, hon, but it would just make me giggle.”
I also felt it was time to lay down the law and take even greater control of my stepbrother. I sat him down one evening for a “serious talk.”
“Sit down, little brother. This is something we need to talk about.”
He looked to be in great fear of what I might have to say. “What is it, Zoe? I mean, you didn’t… You know… Tell anyone about my…”
“About your little baby dicklette? Oh sweetie, you know I would never do that. I love you, and I just want to make this tough hand you’ve been dealt as easy as possible for you!” He let out a sigh of relief.
“But this is important,” I told him. “And it is about your inadequate penis. Remember how this whole thing started, Jimmy? I caught you watching porn and playing with yourself.” He reddened, seeing this WAS going to be just as uncomfortable a conversation as he’d feared.
“Don’t be embarrassed! It’s like I said, I know it’s something all teenage boys do. And I’m sure you masturbate even more than most boys, because it’s not like you can expect to go out and get laid like a man with a normal sized cock could do.” I could always sense the point when Jimmy would probably rather jump out the window than continue the conversation. This was the point I would always become a bit more aggressive with the way I stroked his penis.
“But here’s the thing, Jimmy: you’re not like regular teenage boys. You know that now. Other guys can jerk off, shoot a load in five minutes and it wouldn’t be a big deal for their regular sex life. But with you it would be different when you want to go out and actually make love to a real woman someday.” I looked into his eyes. “You do want to find a way to someday make love to a real, sexy woman, don’t you little brother?”
He nodded. As mortifying as the “problem” he had come to believe he had was, he couldn’t deny that he still wanted a regular, normal relationship.
“That’s good, babe. We’re going to find a way for you to do that, you know. But young guys are notorious for being quick to cum. You’ve heard that, haven’t you? No girl wants a guy with no stamina, but she’ll be forgiving of a guy with a huge cock, or even an average one. It’s to be expected if you’re with a boy your age, after all.
“But if you go to bed with a girl and she sees that you have a tiny, tiny nub for a penis AND you cum too fast? Honey, she would be furious. A babydick and a minute man would destroy any potential you have. That’s the sort of thing she wouldn’t just laugh you out of bed over, she’d make fun of you with every single one of her girlfriends over. Your reputation would be ruined. Forever.”
I had created a vivid enough scenario to make the possibility seem all too real for Jimmy. “Oh, gosh! I.… I really don’t want that to happen. She would, she would really tell everyone?”
“Everyone, Jimmy. No question. Most other girls can be really cruel. So you see, your only shot if we can find a girl nice enough to feel sorry for your little lack, is for you to at least have loads of stamina. So we can’t have you jacking off. I don’t want your body getting used to three minute wanks in the shower or before bed.”
“So I just have to quit ejaculating completely?” He asked shyly.
Adorably, he could never bring himself to use anything but the proper terminology. I laughed, and wrapped my hands tightly around his hardening cock. “No, silly. I know how boys your age are, and I know that would be impossible. But you do have to control your orgasms.” Smiling sweetly, I stroked harder up and down and watched his eyes roll back in pleasure. “I have to control your orgasms.”
“That’s right. You’re not going to masturbate anymore. At all. But when I think it’s appropriate, I will help you release.” Now I stroked faster, and caressed his balls. “Wouldn’t you like that, sweetie? If I helped your itty bitty dickie feel good from time to time?”
“I would,” he breathed.
I alternated jerking him slower, then faster for some time. Keeping him just on the edge and then methodically walking him back, I wanted him to truly feel what control was.
“So you have to promise me, okay Jimmy? Remember, this is going to work unless you truly agree never to touch your little boyhood. It’s going to be tough, and you’re going to be aching to rub your widdle babydick, but you’re going to resist. If you feel really desperate, you’ll come to me and ask nicely for me to relieve you.” Even in the throes of excruciating pleasure, I could see how queasy the idea of approaching his beautiful stepsister and asking for sexual relief made him.
“Okay, Zoe,” he said, “I promise.”
“And do you know what, Jimmy? I know you’re going to keep your promise. Do you know why?” Now I intensified my touch, intensified every sensation. “Because I’ll know if you’re lying,” I whispered. “If you cheat and put one finger on that cute little stub of yours, I’ll know if you lie to me about it. And honey, I want to help you, but if you go behind my back and lie to me, there are so many things I can do to make life miserable for a boy with a miniature sized cocklette. So let’s just be honest with each other, because you know everything I do is to help you.”
My step brother quaked in fear of what my words implied. “I won’t lie,” he squeaked. “I won’t cheat and I won’t lie.”
“Good, hon, so promise me: I promise not to cheat and touch my miniscule pee-pee.”
After a good, luxurious stroking of his shaft, he repeated. “I promise not to cheat and touch my miniscule pee-pee.”
“I promise not to stroke my tiny little baby cock.”
“I promise not to stroke…” He hesitated to speak until I hesitated to continue jerking him. “Not to stroke my tiny little baby cock.”
“Good boy,” I said, rubbing him in earnest. “A good little boy. You deserve to cum nice and hard for me. Shoot your little load for me, my little tiny man.” He needed no more than those words and one final stroke from me. I had him fully trained to come on command for me. It was fun to watch the shame flood into him immediately after release, to see those cheeks burn. Now that Jimmy was wholly under my control, the possibilities were limitless.
Jimmy’s most humiliating ordeal yet. Your comments keep me going, so please let me know if you’re enjoying.
I had Jimmy perfectly under my thumb at this point. I had him believing everything I told him, despite the fact that what I told him always seemed to devastate him. Throughout it all, what held it together was that I never gave the poor kid reason to believe I had anything but his best interests at heart. Jimmy stood for my torment (and my torment seemed all the more painful) because with every little word I made him believe I was trying to help.
Occasionally, when Mom was out of town and I sensed my stepbrother was at a breaking point of sexual frustration, I would again give him release while lovingly degrading his cock size. I had no doubt whatsoever that, despite possessing the perpetual horniness of a typical teenage boy, Jimmy was adhering to my orders not to play with himself outside of my watchful gaze.
When the moment struck me and I was feeling particularly generous or cruel (since in truth my jerk sessions with Jimmy were both), I would without warning instruct him to strip. What was so cute was that even as he begins offering less and less resistance, the sheer dread in his eyes never disappeared, and his expression would always carry a silent plea for me not to continue, even if he was incapable of voicing it.
I’d always start from a place that suggested pure charity. “How is your itty peen feeling, baby brother? Don’t you worry about anything at all, okay? We’re going to figure out a way for you to be happy even with an undersized dickie. I’m going to make your boyhood feel good now, and we’ll figure out a way for you to live with a penis size that makes girls giggle.”
At most, I’d bring my full, ruby red lips close enough to his groin for him to feel my warm breath on his cock, but never any closer. Full-on contact with my mouth, a sweet, warm, wet blowjob was held tantalizingly in sight but always out of his grasp. Through it all, he’d try to be so strong, but I wouldn’t let him block out any of my words. In the end he’d grunt the hardest as my expert hands stroked him to orgasm while whispering the meanest of permission: “Go ahead little guy, go ahead and cum. You can let your itsy bitsy dicklette shoot now. It’s time for that babydick to release.”
He would shoot a massive load, his eyelids clenching in such raw excitement. After his orgasm, he would immediately return to the world with utterly sad eyes. By the time I reached my room, I would be in a state of uncontrollable arousal myself. While Jimmy’s orgasms were now a matter of public spectacle, I would lie under in bed under the covers in comfort, barely rubbing my clit for even five minutes before coming breathlessly, often several times in a row. I would always sleep so soundly afterwards.
I had concocted the next phase of Jimmy’s torment with complete precision, but I spun it into action as if the notion had just struck me. “Little bro, I have the best idea!” I told him, when we were alone one night.
“What is it?” He asked anxiously. He had grown nervous about my ideas.
“We’re going to find you the perfect girlfriend. We’re going to make you feel totally confident, and find you somebody who’s totally cool having a tiny cocked boyfriend.” I smiled.
Jimmy looked hesitant but curious. He had now taken his ‘under endowment’ as such gospel that such an idea appealed, but seemed too good to be true. “I but how are we going to do that? I mean, that’s what I want, but…”
“But it doesn’t seem possible that any girl would really be happy with a little pee-pee your size? I know that, silly, but I have the perfect plan. Just come with me!”
I led him back down to the computer room, the sight of our first encounter and so much of his suffering. “Here’s the problem, babe: if you start dating a girl you like, get close to her and after hitting it off, go to bed together, she’s eventually going to see your tiny boyhood, laugh her ass off and hurt your feelings.” My stepbrother blushed, despondent that such an outcome at the reveal of his penis was taken as a given.
“But the only other option is that you ask a girl out and before getting too close, whisper your little secret, that you have a severely undersized dick. The problem there is it’s such a weird thing to say on a first date, she probably won’t want to continue, and she’s likely to have a good giggle when she tells her girlfriends all about it. You don’t want that, do you?” My little puppet shook his head silently, as I knew he would.
“So what we’re going to do is put your profile on a computer dating site. Everything about you – looks, personality, interests, and see what matches come up.”
“Um… But Zoe, wouldn’t wouldn’t the same thing just happen if we go out and she finds out about.”
“About what, sweetie?”
He steeled himself with a sigh. “My small size.”
“Your small size? You mean your tiny sized baby pee-pee, right hon?”
“Th-that’s right,” he whispered as he turned a deep shade of crimson. “My tiny sized b-baby pee-pee.”
Grinning at his embarrassment I continued. “Here’s the great part. We’re going to fill out and post a full profile for you, and we’re going to include a description of how little you are. Length measurement, girth measurement, we’re even going to attach a picture of it.”
All the colour drained out of poor Jimmy’s face. “I can’t do that. Oh gosh, that’s too humiliating. And who would respond to my profile if I do that?”
“That’s the point, darling! The only women who would possibly respond are the ones who know exactly what the situation is going into it, and who would have to be totally cool with it! People have strange fetishes for all sorts of bizarre abnormalities, Jimmy.” I let my description sink it a bit, making it clear that my stepbrother knew I thought of his phallus as nothing short of a deformity. “I mean, I certainly don’t know any women who would actually be okay with an undersized dick, but there HAS to be a few out there.”
Jimmy considered it. It was a debasing, mortifying plan, but I could see that the logic seemed to make a certain amount of sense to him. And the beauty of my plan was that there WAS a logic to it – if, that is, Jimmy actually had a tiny penis, or if I actually planned to do what I said I did. “I guess you’re right, Zoe. It does seem like it could kind of work. But it’s just so embarrassing, admitting what I have down there.”
“What have I been saying all along, little guy? You’re never ever going to deal with this and have a happy, healthy life if you don’t accept your total lack. This is a perfect example: do you want to sit around feeling sorry for yourself and never meet a real girl because you don’t want to admit your smallness, or do you want to acknowledge that you have a micropenis and actually have a real relationship with a beautiful, understanding girl?”
He brightened up a bit at this (of course, it didn’t hurt that I was rubbing my hand all over his cock through his shorts) and agreed. I leapt for the keyboard, letting my hand drift down to his crotch every now and then, caressing his dick just often enough to keep it semi-erect. “Awesome!” I said, “This is going to be so great for you. Let’s get to work on your profile.”
We wrote a fine, accurate profile for Jimmy while I intermittently stroked him. It described him well as a nice, thoughtful, and shy young man. I took a couple snaps of his face with my camera phone for his main profile pics.
When it came time for the phallic portion of his profile, I took the lead and he was more than relieved to leave it to me – at least at first.
Tightening my grip on his cock, I smiled whimsically at him as I nuzzled his neck. “You know what’s next? Right?”
“N-no,” he breathed.
“We need a picture of your dicklette, sweetie.”
The hair on his neck stood up and he looked to be working up the courage to utter something. Even this deep into it, faced with the cold reality of actually having his cock photographed something in him hesitated.
Before he could say a word though, I giggled impishly and snapped a photo. “There we are! I’ll just save the image for safekeeping. But let me just make sure we can actually see your sweet little nub clearly enough.”
I made a production of squinting while Jimmy dealt with the realization that I now had a picture of his dick saved to my phone, and all that implied. “Looks good. Well, as good as it’s going to get anyway. I’ll just sync these pics to the computer and upload them to your profile tomorrow and we’ll be good to go!”
I removed my idle fingers from his penis and began gathering my things. “Wait, are you not going to… Um, I mean d-don’t I get to?”
Poor Jimmy must have had such excruciating blue balls! I could actually see his cock twitching, so close to release. “Get to what, Jimmy?”
“N-nothing. Never mind.”
He couldn’t bring himself to truly ask his stepsister to let him cum, and I was going to enjoy leaving him hanging. “Okay, if you say so. G’night, Jimmy! Be good. I’ll get your profile online first thing tomorrow!”
The first thing I DID do the next day is get his profile up. But unfortunately for him, things would be a bit different than promised. I trashed the phone pic I had snapped of Jimmy. It was of a perfectly average sized erect cock, and if I attached to a dating profile, the most likely response would be a lot of surprised stares for having included it and maybe even a compassionate girl or two who would write to reassure him that his size was just fine.
Instead, I did a quick google search for terms like “smallest penis” or “tiniest cock” and found the website smallest-dick-on-earth.com, otherwise known as ‘The Small Dick Club’. I looked at the Gold Members and they were truly miniscule dick, medically a micropenis most likely – roughly similar in dimension to what I had been falsely telling Jimmy he was.
I also had no intention of putting my stepbrother’s dating profile up on ‘Okcupid’, the popular mainstream online dating site I told him I would upload his information to. Instead, I created an account on a niche site called 7orbetter.com. This was an up-and-coming site used exclusively by size queens with very specific cock requirements, looking specifically to find men who were not just eligible but well hung. If women on ‘Okcupid’ would mostly ignore Jimmy’s profile, women on 7orbetter would be actively hostile towards him for being on it. But of course, my sweet, trusting little victim would never be aware that his dating responses were coming from anyone other than regular, everyday female ‘Okcupid’ users.
After showing Jimmy that his profile had been uploaded, I waited a few days before making my next move. I wanted a few messages to accumulate in his inbox, and I wanted his blue balls to become even more aching. How painful it had to have been him. A horny, healthy, teenage boy, to be walking around with this constant frustrating need to cum, but being unable to. Simply because whether he knew it or not, he’s at my mercy.
Every now and then I would make a pointed remark about his “tininess” or “little problem.” I kept a close watch on his crotch and to my absolute delight, I could see him start to get a bit of a stiffy every time I did so. I was so thrilled that deep within his brain, whether he liked it or not and whether he was aware of it or not, I was implanting an inescapable association between humiliation and arousal.
Finally, it was time. “Come on, Jimmy,” I told him. “Let’s see if your little penis has any takers!”
He was blushing terribly the entire time as we loaded the profile. I think some part of him still couldn’t believe he had actually created a dating profile laying out the complete specifics of his cock size.
I gave Jimmy a comfortable seat and an unobstructed view of the computer monitor. Although I covered up the ‘7orbetter’ logo on the page, I wanted him to see each message directly with his own eyes.
“Let’s take your pants off, honey,” I said, I gave him no reason, nor did I feel the need to. Of course it didn’t hurt that he was probably so desperate to cum that he would do anything that might make that outcome more likely.
He was sitting bottomless beside me, me in a low-cut top and cute pink yoga pants. I prided myself on wearing my prettiest outfits when he was naked in front of me. He tried to hide it, but he would always get so fixated on me, on how perfectly bubbly my ass looked in those yoga pants.
“Are you excited?” I asked.
“K-kind of,” he said, “I’m nervous. But I guess that the worst that could happen is that nobody responded.” I smiled. If he thought that was the worst, he would be in for quite a shock.
“Exactly. Now let’s just open your profile inbox and see what we’ve got Look at this! You got almost a dozen responses!” Jimmy brightened considerably. “Didn’t I tell you this would be a great idea, little guy? It looks like there are plenty of women out there who can deal with a teensy little dickie.”
As much as his mind was focused on happy possibilities, his dick twitched and perked up at my emasculating trigger words. I took my stepbrother’s hard cock in hand and softly petted it as we clicked into the responses.
“Here’s one from Julia M, and it looks like she lives nearby. Let’s see what she looks like.” I could tell Jimmy just wanted to read the messages, his curiosity bubbling, but I wanted each of these girls to be as real as possible for him before he read their words.
“Wow, she a knock-out!” I said, and she was. A smooth-skinned, vivacious redhead, her pics were playful but sultry. “What do you think, Jimmy? Isn’t she pretty?”
“She’s amazing,” he said, I’m sure he didn’t think any woman would respond to his profile, let alone one so gorgeous. “Does she really want to go out with me?”
“Let’s see what she has to say.” I clicked over to the inbox, knowing full well this 7orbetter size queen would have something much different to say. Her message, along with her sexy profile pic, displayed for us. I read it out loud to Jimmy, beginning to stroke his dick:
“What the hell is wrong with you, trying to get dates here with a cock so fucking tiny? You really think anybody on this site is going to be interested in your laughable little micro-dick? Fuck off.”
My stepbrother sucked in a breath, taken aback and devastated. I could feel his pulse racing, and his face seemed to burn.
“Oh, sweetie,” I said, “I’m so sorry! I don’t know why she had to be so mean. I mean, you already know you have a super tiny cock, there was no need for her to message you and be so rude. Some women are just too honest for their own good! Let’s keep reading, they have to get better than that.”
“May-maybe we should just quit,” a still shocked Jimmy said. “I don’t know if I want to read anymore. That wasn’t what I was expecting.”
“No, no, silly, we can’t stop now, there’s like ten more messages of girls who probably feel the opposite about your little dicklette and want a date with you!”
I clicked the next profile, again going through the effort of giving Jimmy a better look at the girl. Karla was probably in her late twenties, raven haired with glasses, and gave off the impression of a no-nonsense persona.
I increased the speed of my strokes as I whispered her lines into poor Jimmy’s ear: “I honestly feel like this has to be some kind of joke, but it isn’t very funny.”
The message reads: If you’re serious, there has to be something seriously wrong with you to think your insignificant, miniscule joke of a penis is acceptable here. Please delete your babydick profile, and come back when you grow to ten inches.
Intermittently, my stepbrother would plead not to hear any more replies, but I was insistent that among them would be a gem. Throughout it, he was clearly emotionally wrenched but his cock remained hard as a rock. I kept him on the edge as I went on down the list:
Nicole, a tanned, buxom bleached blonde party girl type: Ew! What are you doing posting pictures of your gross, itty bitty peen here? So disgusting you little perv!
Annie, a brunette girl-next-door type with a sly smile: I just want you to know that my friends and I had a good twenty minute laugh over the size of your tiny, tiny, tiny, TINY dick. I’m completely certain you won’t actually get any dates here, but rest assured you and your cockette did give us a bit of joy.
He was breathing heavy and close to the edge, no longer asking me to stop reading as it became clear how much pleasure their cruel words were bringing him. My fingers played lightly along the tip of his penis.
Mandy, a pixyish Asian young enough to still have adorable baby-fat. Her message said, why would you be trying to meet a girl on this site when you have something so ridiculously small in your pants? We’re looking for somebody with the equipment to please us here, and I can guarantee that ain’t it. I would giggle and kick you out if you tried to trick me into bed with a hamster penis like that.
Jan, an enigmatic brunette with perfect cleavage and the slightest hint of nipples pressing against her tank top: HAHAHAHAHA!! Babydick, babydick, babydick! Dude, you can’t post that shit here and think it’s okay – we’re looking for real men here, not pathetic, infant-sized little boys. Get it through your head that the girls here like big, huge, thick cocks and you have a tiny, laughable, microscopic, miniature little stub, and you won’t ever be able to satisfy us.
There was no going back after this. The slightest touch would have pushed Jimmy over, but I squeezed and jerked furiously as I read Jan’s message. I never saw somebody come so hard. It seemed to drain everything out of him.
As he caught his breath, I kissed him on the cheek and rose. “That’s all of the messages, Jimmy, I said. “I’m so sorry. I really thought there’d be at least one girl SOMEWHERE who would be interested in your undersized pee-pee, but I guess I just told myself that because I want you to be happy so much. I’ll keep checking your inbox in case a nicer girl writes you, but I won’t make you read the messages anymore, okay sweetie?” Jimmy, exhausted as he was, looked genuinely grateful to hear that. I gave him another kiss on the cheek. “Clean up your mess before you go to bed, hon.”
I too had one of the best orgasms of my life after I had left poor shell-shocked Jimmy and retired to my bedroom. But as satisfying as the moment was, I had planned to humiliate my stepbrother even further.
I kept my promise not to read him anymore indignant emails from the responding size queens. In fact, I deleted his profile all together. But in the meantime, I also created a new one for him, keeping his personality, interests and face pictures exactly the same, and uploading it back up to 7orbetter. But I omitted any written references to his dick size, as well as the images of the tiny micropenis I had attached.
I did a google image search, only this time my search terms were phrases like ‘huge cock’, ‘enormous penis’, or ‘monster sized wang’. When I found the nicest, thickest, hugest one I could possibly find that wasn’t an obvious photoshop, I saved and attached it to my step-bro’s new profile and waited.
During the next week or two, I made a big show of being sweet and nice to Jimmy. I mentioned his smallness only sporadically, and always indirectly and in the context of making him feel better about his “disadvantage. After all, I had big plans, and it just wouldn’t work if he was TOO broken to have a glimmer of hope.
Of course, Jimmy’s ‘monster cock’ profile had racked up plenty of responses in the meantime, including around the area. I carefully read through each of them, in search of just what I was looking for before I found it: Ericka. Ericka was undeniably gorgeous, a spirited looking young woman with flowing, lustrous red hair, but she gave off an aura of approachability rather than intimidation. She looked to have perfect, shapely tits and the rest of her body was just as stunning. Just as importantly, her interests and likes also genuinely seemed to align with Jimmy’s. I knew I had my woman.
I caught Jimmy just after school and told him I had great news. “It’s your dating profile. You’re going to like this, trust me! Just you wait and see.”
He was still reluctant nonetheless. “Zoe, I don’t know. I kind of thought we were just going to forget about the whole thing. After, you know, after how it went last time.”
“Don’t you worry it, little bro, it’s nothing like last time. Remember, that’s why I’ve been screening your inbox for you. I haven’t come to you with mean messages since then, have I? Now follow me!”
Again, taking care only to hide the site logo, I showed him the personal message from Ericka waiting in his inbox. Before I let him read it, again, I navigated to her profile and let him see her pictures and read her intriguing profile. As nervous as he was, he couldn’t help but seem excited. And why wouldn’t he be? She seemed perfect for him, and beautiful to boot.
Still, I giggled to myself when I noticed him trembling as I clicked on her message. He was so petrified that it would be like the first time, and this cute young girl would be singling him out for ridicule!
Ericka’s message was just the opposite though. It was cordial but flirty, connecting directly with him on a few key interests and hobbies they had in common. And his face lit up as he read the last paragraph:
It reads: hey, I just wanted to let you know I haven’t done too much of this online dating, and I’m not in the habit of responding to profiles here. But you’re super cute, and it looks like we have a ton in common, so I thought I’d go for it. And okay, I’d be lying if I didn’t admit your cock is really appealing to me. I don’t want to come across like a slut, but it’s definitely something that really interests me.
Jimmy looked happier than he had been in weeks, both relieved and elated. It was so cute. He was glowing, and probably would have remained that way even I hadn’t made him reply to the message. As excited as he was for the possibility, he was nonetheless still extremely nervous, and I had to lead him every step of the way in responding, having a few conversations, and after a week or two, setting up a time to meet for an actual date.
When the time came around, I knew I had some serious work to do if I were to enjoy the fruits of my labour. It was simple enough, since as I mentioned I was and am rather tech savvy, but it required a little legwork. I wouldn’t be able to witness Jimmy’s first date, but a simple recording device hidden in the wrapping of the small flower arrangement I instructed him to gift her with would let me listen in.
But the main event wouldn’t be the dinner date, but rather my stepbrother’s “special time” afterwards. After we found a nice, classy but non-intimidating restaurant for the pair to get acquainted, I took the liberty of booking an overnight room at a nearby boutique hotel. He was a bit put off initially, both by my presumptions and what it implied.
“I’m just being careful, sweetie,” I told him. “If you don’t end up using it, that’s fine. But you never know! And besides,” I teased, “she did say how interested she was in your cute little pee-pee, didn’t she? That has to mean something, don’t you admit? And trust me, little brother: it’s NOT going to be easy to find another beautiful girl so excited about that widdle nub. If you see any signs that she’s on board for extracurricular activities tonight, kiddo – you take it.”
I let my words sink in. Besides the logic of them (at least according to what he knew), he had to have been aching for such an encounter. Not just the lusty desperation of your average teenage boy, I had teased him many times to the edge over the last week but refrained from allowing him to release. If he were more attentive, he may have found that suspicious, given that my entire rationale for controlling his orgasms was so he would last LONGER, but fortunately, his nervousness and anxiety about the date clouded that sort of rationality.
Beforehand, I showed him the room and fired up the laptop so that he could check his inbox to make sure the date was still set. At least that’s what I told him. The real reason was so I could leave the laptop open, with the webcam software I had set up running on sleep mode. It was a simple matter of setting it up to motion activated so it would stream back to me on our home computer if they came back to the room.
When the big night arrived, I listened sporadically to the interaction over dinner, but frankly, most of the conversation was a snooze. Some playful flirting, predictable jitteriness from Jimmy which Ericka seemed to interpret as adorably bashful, and general getting-to-know-you banter. Happily for my plan, they seemed to be hitting if off perfectly. The ticking time bomb – the comparatively unimpressive package that my kid step-bro was packing compared to what she expected – was only alluded to a few times, but it became a hot topic as it became clear the evening may continue.
“So, Jimmy, I hate to sound so brazen, but we’ve been enjoying ourselves and talking quite a bit, so I suppose I can just bring it up now, right? I mean, we both know there’s a certain something, a certain picture that hasn’t come up yet.”
Even without having the visual, I could practically see Jimmy blush. “Umm, that-that’s true. I don’t exactly know what to do.”
She made it easy on him, interrupting. “Oh, darling, it’s so cute how shy and reserved you are about it! Honestly, I mean that. You haven’t mentioned it once tonight, but honestly you could have. I was so excited when you messaged me back. I know that,” she took on a husky whisper here, “that a cock your size may not be for every woman. But I have to tell you, hon, it’s exactly what I love. It looks perfect to me.”
I was almost positive that Jimmy must have popped a little boner by now at her interest, and felt such a rush of relief and positivity about his endowment for the first time in ages. “That’s so good to hear, Ericka. I mean, I know presenting it in my profile is sort of… bold, but I just didn’t want it to be a surprise. Especially with somebody that I like a lot.”
“Mmmmm… It would be a pleasant surprise for me, hon, trust me on that. And I really like you a lot too. I’d sort of like to keep the night going, you know what I mean?”
“Well, I-I, I don’t want to be too forward, but if you, if you want to, I actually I have a hotel room just a few blocks away for the night.”
“A hotel room?” She said, “Now that IS awfully bold, Jimmy. Kind of presumptuous, don’t you think?”
“No! I mean, I just thought, in case, in case,” he stammered.
“I’m teasing you, sweetie! Confidence is sexy; I like that you made that plan ahead of time. And I’d love to keep things going at your room.”
I probably felt just as much giddiness as my stepbrother at that moment. I couldn’t wait for my plan to unfold.
The two of them sped through dinner and dessert, and clearly Ericka wanted to get to Jimmy’s room with little delay. After a perfunctory tour of the space, my webcam picked up the pair quickly moving closer. It was clear that she was the driving force: I’m sure Jimmy, despite his teenage boy urges, would have been happy to take it as slow as possible, but my girl Ericka knew what she wanted. She practically had to take him by the hand to start making out on the bed.
“You can touch me, baby, it’s okay,” she said, “Put your hands on me.” He tentatively draped his hands along her waist, rather awkwardly as if he were afraid to move them anywhere but the safest of spots. She was dressed in classical, deep blue dress, elegant enough for a first date but not off-putting dressy. The end fell just above her knee, showing enough skin to clearly be provocative and enticing. As she leaned into Jimmy’s, the hemline slid back, almost to her thighs and she made no effort to pull it back down. Jimmy rested a hand timidly on her knee, which Ericka clutched with her own to move it higher up and squeezed to indicate he increase his intensity.
“Jimmy,” she said, drawing him back with a palm on his chest. “I can’t wait any longer. You’re so shy, but you don’t need to be. You know what I want to see. What I NEED to see.” She giggled. “And to touch. And to play with. And to suck. And to have inside me.”
Despite the questionable quality of the webcam, I could see Jimmy perceptibly shaking like a leaf. “I-I well, aren’t we going to do OTHER stuff before we…”
“We will. But I want to see so badly. I can’t wait. Don’t you want to show me that beautiful cock, sweetie? I promise,” she teased. “You’ll get to see all you want of me too. And you’ll get a whole lot more than that.”
Things were moving out of control so quickly for poor Jimmy. I could see he wanted to protest somehow, but the situation was practically out of his hands. And besides, the allure of what Ericka was promising was its own compelling force. He did the easy part first, flipping his shirt over his head and discarding it. Then he unzipped his pants, shimmying out of them – he was so nervous he almost fell over twice manoeuvring out of them. Then came the big moment.
“That’s it, baby. God, I can’t wait. I’m going to make that perfect cock feel so good, I swear. Mmmm, I’ve been dreaming about it.”
He gulped, audibly enough that I could hear it, and steeled himself. I could see him having the same internal debate as to when one is entering a cold swimming pool: get it over with in one swift action, or do it gradually? He chose the former, whisking his boxer shorts down and presenting his package to his date.
There was a silence. If this was a TV sitcom, you would have heard a “sad trombone” sound cue. Ericka’s expression turned from fiery anticipation to wide-eyed disbelief in a flash. She mouthed the word, “What?” And released a gasp.
And then, there was no stopping the torrent. “Are you FUCKING kidding me? This? This??!” There was menace in her voice. Ericka seemed like a nice enough girl, but from her point of view she had been seriously misled.
“W-what’s wrong? I thought you wanted…”
She was in no mood for his perspective. “What I WANTED was a real cock. A big cock. A MAN’S cock. You seriously came to me with this? This inadequate waste of time?”
Of course Jimmy had heard enough and he was reaching for his clothes. Ericka leapt to her feet in response. “Oh no you don’t, little boy.” She stepped onto his underwear, preventing him from covering himself.
“I’m s-sorry, I’m sorry!” He stammered.
“Oh, now you’re sorry? Jesus Christ. Well, you should be sorry. Because you have a sorry little dick. God, you fucking wasted my night with your worthless babydick. Where’s your cock, asshole? Because I was expecting a real cock, and this most certainly isn’t one.”
She was looking him straight in the eye, furious and demanding. And, I was ecstatic to see, my cruel conditioning had proved effective. As demeaning and humiliating as her words were, they were causing him to grow erect. A fact which didn’t escape Ericka’s notice.
“Holy shit,” she chortled, a deep and reverberant laugh. “Are you getting hard?” She dropped to her knees. The proximity of the beautiful girl’s to his penis very quickly exacerbating Jimmy’s condition. “Oh my god, you are. I’m sitting here laughing at your unacceptable disappointment of a penis and that’s giving you a boner?” She looked up at him. Jimmy clenched his eyelids shut in deep, deep shame.
“God, Jimmy, there’s really something wrong with you and your worthless dick.” He looked down. Kneeling before him, he could see down her fashionably low-cut dress to the milky white skin of her generous cleavage. She took hold of his shaft, grasping it with the disdainful quality that a curious child might examine a disgusting reptile.
It was throbbing in her hands. “I’m going to laugh about you with all my friends, weirdo. I’m going to get you blocked from that website, because your dicklette isn’t enough. You would be fucking me if you had the kind of cock I was expecting. But what you have is a joke. Your worthless little loser penis is a terrible, inadequate joke. You are way, way, way too small for me.”
The combination of Ericka’s humiliating words and the soft touch of her hands was more than enough. I could see him trying to fight it, but the outcome was inevitable. Jimmy’s body shook, his fists grew white knuckled. He grunted, yelped. And without warning, he exploded, spraying ropes of cum all over his date’s hand and pretty blue dress.
“OH MY GOD!” She darted away, a horrified and shocked expression, but the damage was done. “Oh my fucking god!” As if removing a radioactive substance, she grabbed a hotel towel and wiped as much of Jimmy’s semen away as she could.
“Wow, thanks for a great date,” she spit out sarcastically. “I’m getting the fuck out of here. I don’t know what the hell you thought you were trying to do, but trying to get laid on that dating site with a dick like yours is pathetic, you LITTLE boy.”
She was halfway down the lobby with a slam of the door before Jimmy’s breathing had even slowed back to normal. The poor boy looked positively shell-shocked. I smiled in satisfaction and shut off the webcam, already knowing Jimmy’s humiliation would bring me my strongest orgasm yet.
To be continued…