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by email@example.com ©2013
Looking back, I’m sure poor Jimmy didn’t know what hit him. In the span of less than a year, his dad started dating, then married, a new woman. He had to move into a strange new house with a strange new stepmom, not to mention a new stepdaughter – me.
Just a few months after the marriage, Jimmy’s dad succumbed to a heart attack at the office and passed away. Jimmy stayed with us, having to quickly adjust to a home life around two women. What made matters worse was that Jimmy was a painfully shy teen, and I could sense this before we even met (we attended the same high school, though I was slightly older than him). But even months later, he was the same awkward boy around us: stuttering, quiet, having trouble even meeting my gaze.
Of course, I won’t deny that I probably made things even harder than necessary for the poor kid. Before our parents marriage I had noticed him staring at me in the hallway (though I had developed early, and was used to receiving that kind of attention), and I took full advantage of the knowledge that Jimmy almost certainly had a little crush on me. I would lounge around in my little t-shirt and boy shorts in front of him, rest my feet on his lap under the guise of “sisterly” bonding, and sweetly ask him for favours like doing my laundry or cleaning my room.
It was all mostly harmless, but I admit that having such control over him was a turn on. Jimmy was such a sweet, innocent kid, but despite being just a little older, I was unequivocally brighter, more streetwise and more mature – especially since in so many of our conversations the blood was no doubt rushing out of his brain and into his dick.
That brightness also translated into my being much more tech savvy (I was actually something of a computer/gadget whiz), which I was beginning to also use to my advantage. I had taken to getting on the family computer after Jimmy and checking the history to see just what he had been up to – the poor kid didn’t even know well enough to activate private browsing mode. I saw the regular stuff – checking scores on ESPN, updating Facebook, whatever. And after jumping on after a few of his late night computer sessions, I found more embarrassing material – swimsuit model galleries, porntube, dirty tumblr sites.
I obviously already assumed that little Jimmy was looking at porno and jacking his cock at some point or another. But now I knew exactly when he was doing it and to what. It was typical teenage boy stuff, nothing good enough to confront him directly over (despite how deliciously embarrassed it would have made him). But I started teasing him with it, putting him off guard without ever tipping my hand that I knew for sure.
“Were you up late last night, kiddo?” I asked him the morning after confirming one of his jerk sessions. Standard fare, really – getting going with a bikini gallery of Brooklyn Decker and finishing on some softcore lesbian videos.
“Oh, um, not really,” he said. “I was just finishing some homework. Why do you ask?”
“Oh, no reason,” I said disinterestedly. “I thought maybe you were working out or something – I heard some grunts coming from downstairs around midnight.”
“Yeah, just a lot of heavy breathing and grunting.” Jimmy was trying so hard to be cool, but I could practically feel him gulping, a hot shade of crimson falling over his face. “Must have just been a dream I was having though.” I let just a brief moment of relief pass through him before continuing my needling. “So what were you up to today, Jimmy? I was thinking about going to the movies and I thought you might want join me.”
“Yeah, I kind of wanted to see that movie Just Go With It – you know, with Adam Sandler and… who’s that girl in it? Brooklyn Decker?”
He sucked in his breath and took on an expression like a cornered animal. Did I know something? What should he admit to? Was he being paranoid? I wanted to burst out laughing but I just smiled.
“That IS it, Brooklyn Decker!” I said. “Did you want to come with me? I just thought you might be interested. She’s awfully pretty, don’t you think?”
I could tell he had no idea how to react. “Um, I better just… just stay in and finish that homework.”
“Okay, hon. You’ll just have to watch Brooklyn some other time.” I relented at last, careful not to reveal for certain that I had been keeping tabs on my little stepbro.
It wasn’t until a few weeks later that I stumbled upon the bit of browsing history that could REALLY be useful. This wasn’t part of a masturbation session at all, just a collection of basic, simple google searches: “What is an average penis size?” “Is my penis size normal?” “How do you know if your penis is big enough?” My little developing brother was worried about his cock size, I realised gleefully! I could have so much fun with this, if I played my cards right…
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It was just a couple days later on a night when my mom had gone out of town on one of her frequent business trips when I started to put my plan into action. I had a good guess by now of the times when Jimmy would generally be going to the computer to whack off, and you could hear a different kind of movement in his step when he was on his way, a sort of bashful, tentative creeping. I listened for his tip-toeing, my cue after waiting ten or fifteen minutes to sneak down after him.
I could hear the unmistakable sounds of my little stepbrother on the other side of the study room door. Careful not to make a sound, I crept up to the door and readied my best expression of shock. Without warning, I flung it open and “accidentally” walked in on Jimmy! His dick was hard in his hand, his pants around his ankles and muted porn played on the desktop computer.
“Hey Jimmy, I was wondering if you’re still – OH MY GOD!” I cried. I covered my mouth with my palm in mock horror. “Oh my god, you’re masturbating!” I exclaimed in a stage whisper.
Jimmy’s horror, of course, was anything but mock. In an instant, I witnessed shock, terror, humiliation and devastation pass through his face. “Zoe? God, oh shit!” He hunched over, fumbling with his waistband as he struggled to pull up his pants.
As natural as can be, I adjusted my expression of surprise into uncontrolled hilarity. I snorted in laughter, tripping over giggles as I cried “I’m sorry, I didn’t mean to…” (giggle, chortle) “… to disturb you!” The look on my face was one of unmistakable mirth. After dragging out my interruption as long as possible, I finally left and shut the door behind me, the horrified look in Jimmy’s eyes still clear in my mind.
Back in my room, I couldn’t help wonder about all the things Jimmy was feeling. He must have felt his life was over, that he’d never be able to look me in the eye again. My laughter must still have been ringing in his ears, and he must have been agonising about just what I had found so funny. I had so much more humiliation planned for him, but for the moment I just left him with his agony.
The one potential hitch in my plan was that Jimmy’s penis, from what I saw, looked to be a perfectly normal size. Not big by any means, and possibly just a shade below average, but certainly not tiny. But this didn’t strike me as being a problem – after all, if he was googling queries and reassurances about his cock size, he was obviously insecure already. I just had to exploit that.
I can’t say why I got such a charge over the prospect of tormenting poor Jimmy like this, over giving him a needless complex and hurting him so deeply. All I knew was that the power I had over him, knowing I could break his fragile psyche, made me unbelievably aroused, both physically and mentally, and I had no qualms about proceeding.
About a half hour later, I visited Jimmy in his bedroom, making sure to knock first. His “come in” was so weak and shaky, I’m sure he would have preferred to crawl into a cave and not see or speak to me for as long as possible.
But that was not to be. I let myself in and sat next to him, now fully dressed, at the edge of the bed, gently rubbing his back. “Hey there, little bro,” I said gently. “How’re you holding up?”
“Er, I’m fine. Fine. I’m sorry. That… you know. I think I’m, I’m just going to go to sleep for the night.”
“No, no, Jimmy, that’s why I came to talk to you. I don’t want things to get weird between us now. You were playing with yourself. It’s okay.” He blushed, and I could practically feel his cheeks burning. “It’s what boys do. But I wanted to apologise for, you know, giggling back there. Well, for bursting out laughing really. I’m sorry, I really just couldn’t help it, little guy. I’m sure you know why though. You understand, right?” My plans for my stepbrother depended so much on not appearing malicious, on coming across as kind and helpful as possible.
He stared at me with a confused look in his eyes. Clearly he didn’t want to say anything, but his expression said it all.
“Oh, honey, you don’t know? You really don’t?” Jimmy slowly and sadly shook his head, obviously curious but so scared about the answer. “Well… just try to forget I said anything then. I don’t know if I can tell you if you don’t already know.”
“No,” he pleaded. “Please. Tell me.” I could tell it hurt to ask me that – finding out the answer was painful, but not knowing was even worse.
“You REALLY don’t know? Mmmm, I hate to be the one to break it to you, but I guess it’s better you find out from me than somebody who would be mean about it. Sweetie, it’s just that… well, it’s just that you have a really small penis. Really small.” That last bit I whispered, acting as though I was choosing my words carefully, that I was trying so hard to spare his feelings.
As I imagined, at that moment crestfallen wouldn’t begin to describe Jimmy’s expression. He swallowed hard, utterly broken hearted. It was if every word I spoke reverberated inside his head like thunder. You. Have. A. Really. Small. Penis.
“Ohhhh, I’m so sorry I had to tell you! But honestly, you really had no idea? Hon, I tried so hard to keep from laughing – I didn’t want to hurt your feelings – but I couldn’t help it. It’s just so, so little!”
My stepbrother genuinely looked as though he was going to cry. “I… I didn’t know,” he whispered, his voice crackling.
“Gosh, now I’ve gone and hurt your feelings!” I got up from the bed and faced Jimmy, bending down eye level with him and placing my hands atop each of his knees. “You know what? I bet it’s not as small as I think! I only saw it for a second, you know. I may have just made a mistake,” I said, as I rubbed my palm up and down his legs over his jeans. “We have to make this okay.” One hand remained on his leg, the other nuzzled his cheek. I adopted a conspiratorial tone. “I need to take another look at it, Jimmy.”
His eyes widened and he practically gasped. “A-another look? You want to…? Are you crazy!”
“I wouldn’t be able to live with myself if you’re mad at me, especially if it’s over a silly mistake!” My fingertips were drawing closer to his lap, and I could feel the closeness of my warm hand to his crotch quickly melting away resistance. “Now c’mon, let’s take a closer look at what you got. You can only go up in my estimation.”
I didn’t wait for an answer before I unhooked his belt and slid his pants down. He stammered, “Oh! But. .. Zoe… stop…” but he put up no further protest.
I lowered myself to my knees so I was face-to-face (face-to-dick?) with his boxer-covered crotch. Jimmy was trembling so hard that I thought he might pass out, and his heart was beating like a drum. I slipped my hand inside and pulled it out, cradling both the tip of his penis and his balls in my soft hands.
“Oh.” I said nothing more for a full, agonising minute. “Ummm… ” And I let the hint of a giggle enter the timbre of my voice again. “Oh, Jimmy. Please don’t be mad at me,” I said, ‘apologising’ for the full throated laughter in that very statement, “It’s just so hard not to laugh! I just thought… I thought maybe I was mistaken but – but I think maybe I had it right the first time.”
Looking upward, I could see the moisture at the corner of his eyes. “Okay,” he said weakly. “Okay. Okay. Let’s just… . let me just get dressed. Okay.” He was stuttering so cutely!
“Wait, wait!” I moved my hand all over his cock, gripping it more firmly at the shaft now. “We can’t yet. You know what I bet it is? I bet you’re perfectly fine when you’re erect. Your little penis looks super small now, but that’s because I still haven’t seen it hard.” Of course, I knew full well that he was hard as a rock when I walked in on him earlier, but it twisted the knife even further for Jimmy to think I couldn’t even tell that his cock was hard.
“Well, um… we don’t need to do that. Please, please Zoe, just let me get dressed.”
“Of course we need to do that! If we’re going to get a proper look at your dick size, I need to see you with a boner. That’s the only time it really matters.” Poor Jimmy just couldn’t bring himself to admit, to say out loud to me, that I had already seen him with a boner.
“Let’s get these boxers off,” I said. No surprise, being a healthy teenage boy, that it wasn’t long before my manipulations of his cock had Jimmy’s cock springing to life. I ran my hand up and down, squeezing the base, fluttering my little fingers along the head. He groaned, having lost all ability to argue.
Soon, his manhood stood stiff, throbbing with arousal. For just a moment as I gave Jimmy his very first hand job, he shut his eyes and I could hear contented breathing, and the cruelty and agony were forgotten for him. For just a moment.
I snapped him out of it with a poorly stifled laugh. “Oh my god. . This is – this is just what it looked like before. Do you mean to tell me you WERE hard before?” Jimmy had no alternative but to nod ruefully. “Babe, I’m so sorry. I guess I just made things worse, but I couldn’t have imagined that this really is your full, erect size.” As I tormented him, I made no effort to cease my stroking. Up and down, up and down, my wrist flew, becoming quicker and more rhythmic. His balls felt so tight, already full from his previously denied jerk session. “You must be so sad, right? Does it make you sad?”
I could only imagine the conflicting emotions going through Jimmy’s head, being unexpectedly jerked off by his gorgeous stepsister but being simultaneously subjected to such gut-wrenching words. “Jimmy? Did you hear me? Did I make you sad? Does it make you sad knowing you have a boy sized dick?”
I ceased my stroking pointedly, waiting for a response. I could sense he would do anything to have me keep going, and sure enough, he croaked “Yeah,” to my cruel question.
“Yeah? You’re sad your boyhood is inadequate?”
Another question it visibly pained him to answer, but he couldn’t bear to have me quit my furious stroking. “Yeah.”
“I’m sad too, honey. I didn’t mean to hurt your feelings about your little dick.” I stroked harder, faster, pushing him to the edge. “Your penis is just so, so tiny, Jimmy. I just had so laugh because your little penis is so, so tiny,” I whispered, just as I stroked my last furious stroked, feeling the cum course through his shaft. He grunted, and his cock exploded and sprayed cum everywhere, his first ejaculation in front of another human being coming at the hands of a girl relentlessly shaming the size of his cock.
I squeezed, coaxing the last bit of semen out of his dick. Jimmy was dazed, unable to speak and, no doubt, to think. Rising from my knees, I kissed him on the cheek. “Hope that made you feel better, at least a tiny little bit,” I said sweetly, emphasising the words “tiny little” for good measure.
I left for my room without another word. I’m sure by stepbrother felt like he had no idea what just happened, as though he just woke up from a crazy dream. But I had so much more in store for him, soon there would be no doubt just how real all this was.