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After our initial encounter, I eased off of Jimmy for a little while – though not out of any sense of charity or kindness. I didn’t want him to have any inkling that I was purposefully torturing him; the more convincingly I could make it seem as though I wasn’t trying to be malicious but helpful, the deeper it’d hurt him.
For a few days, I made no mention of what had happened between us, nor did I directly reference his dick size around him. He must have been so relieved: I’m sure what he wanted more than anything else was to just pretend it had never happened.
Still, it was obvious that he had residual feelings of humiliation over the incident. He was even quieter than usual around me, and he couldn’t even come close to looking me in the eyes. I even noticed him trembling just a bit every time I would get close to him. It was as if poor little Jimmy could barely function around me, in either body or mind!
But avoiding direct mention didn’t mean that I couldn’t tease Jimmy every now and then. I made sure to use and highlight words like “small” and “tiny” just a BIT more than usual, addressing him as “little bro” more than I ever had. Nothing he could ever take as being a direct slight against him, but just enough to make him wince.
It was especially fun to do that kind of thing at school, when I would catch him in the hallway and other girls were around. Introducing him to friends, I say things like “Jen, have you ever met my LITTLE stepbrother Jimmy? It’s been so nice having a little baby brother around!” He would blush and fall silent in the cutest way! No boy likes to be called “little,” especially when there was always a chance that it was in reference to a inadequate penis. Every time I would call him little with some pretty young girl around, I’m sure it made him wonder: has she told any of her girlfriends about how small my penis is? Have they been laughing about me? How many people know my secret?
Of course, I hadn’t told anybody (putting aside the fact that in truth Jimmy was quite average so there was really nothing to tell). But it gave me such pleasure to think of how insecure it must have made Jimmy, being uncertain exactly who might know about his terrible shame.
After a little while, I was ready for the second phase. I found Jimmy in his room, probably so intimidated by me as usual that he was practically holed up there. “Hey, little brother!” I said.
“Oh, hey,” he said shyly.
“Whatcha doing? Mind if I come in and we have a chat?” I didn’t wait for an answer before sprawling out on his bed and draping my feet across his lap. I wore my mid-length ruffled skirt and had stretched out just enough to give him a tantalising view of my bare thighs and the billowing desire to see more.
“So I was thinking about last week, after I caught you jerking off. Do you remember?” There was no question that he remembered – he would probably never forget! Jimmy nodded slightly, most likely wishing he could run away and hide.
“So I just wanted to tell you again that I’m really sorry if I made you feel bad about having an undersized penis. I mean, I know cock size is one of the most important things that girls care about, but that’s no reason boys should feel insecure about it. It’s not like you can help being small!” I brushed my toes lightly against the head of his covered cock under the guise of stretching.
Jimmy was shaking, and I could see him struggling to form words. “O-okay, Zoe. Thanks. It’s okay though, we don’t have to talk about it.”
“No, but look: what I wanted to tell you is that you may not need to feel insecure at all! I can’t lie, sweetie, your little guy looked super tiny to me, incredibly little.” Jimmy looked to be in such excruciating pain, an agony that probably bled into confusion with the added sensation of my ankle resting against his hardening dick. “But here’s the thing: I’m no expert on penis sizes, Jimmy, I don’t know about inches or average length or anything like that. I just laughed because it looked so cute, like a baby’s pee pee. But I don’t know for sure that you’re not a perfectly normal size.”
“I guess… I guess that’s true, if you say so.”
“Right! So here’s what we need to do, okay? We have to find out what the normal size is, then get you hard and measure your little thing. I bet we find that you’re just fine!”
By now it was hard to tell if Jimmy’s discomfort was from my unwillingness to drop this line of reasoning or from the feeling of his stepsister’s smooth legs dangling just atop his growing cock. “Ummm… I don’t know, Zoe. I think I’d rather just forget about it. I’m just going to try to – try to… ” He sucked in an intense breath as my toes found his no-doubt aching testicles.
“Oh, come on, baby brother! We’ve got to do it. I want to make you feel better. I couldn’t stand it if I had hurt your little feelings for no good reason!”
“Please, Zoe,” he pleaded. “I just want to forget all about it.”
“No way, Jimmy – I want to help you feel better.” I swung my legs up, leaving my stepbrother’s throbbing cock. “Now, let’s see if we can find a ruler.”
I happened to know that Mom didn’t have a ruler or tape measure in the house. That was also why I was able to assume that Jimmy hadn’t had the chance to properly measure his size already. But I made a big production of stomping around the house in search of one before returning. “I can’t find a ruler!” Bless his heart, poor Jimmy looked so relieved!
I let his relief last just a moment before exclaiming, “Wait! I know what we can do – come with me!” I led Jimmy by the hand downstairs to the study, the site of where I first “accidentally” walked in on him masturbating. I let him take the chair in front of the computer and knelt next to him. Kneeling in front, I allowed just the slightest, briefest peek up my skirt. “Here,” I teased, “I know this is your favourite place to sit.” He blushed, and I tussled his hair. “I’m just joking with you, kiddo! Now come on, this is going to make you feel all better, I’m sure of it.”
I opened the web browser and did an image search for a basic ruler. “You see? All we have to is print out this picture and we’ll have a way to measure your pee pee.” The word ‘pee pee’ made him wince every time – it was a wonderful way of insinuating smallness without directly calling his dick small. I knew it left it no doubt that I thought of his penis as akin to an infant’s.
So print out the ruler I did. But poor, technically inept Jimmy had no idea that moments before I came to his room, I did a little messing with the print settings. And instead of leaving the default image scale at 100%, I had changed it to just over 200%. The ruler was printing all right, but it was printing twice big as as the correct image – each inch on the printed ruler on the page was in reality over two inches.
I closed the image tab before Jimmy had a chance to notice the size discrepancy between the image on the monitor and the one being printed. “Now, the first thing we need to do is find out what the average size is.” Without warning, I unzipped Jimmy’s fly and stuck my hand inside. He gasped twice, first in surprise and then in pleasure as I grabbed a hold of his cock, which was still semi-erect from earlier. “We’re going to make this little guy feel all better soon, you’ll see!”
As I begin to type in the search query “What is an average size penis?” (and as I knew it would), Google’s previous search tool completed my request based on Jimmy’s earlier searches. I glanced at Jimmy in mock surprise, and he had the expression of somebody who had been caught. “You’ve searched for this question already? So you DID have some idea that your dick was too little!” I grinned at him. “You told me that you had no idea, that it came as a complete surprise when I told you, but it looks like you MUST have had some idea that you were undersized.”
I kept a hand on Jimmy’s penis as I turned back to the search results. No stroking, no movement at all, just kept it at rest. It didn’t take much more than that to keep him excited, as I could tell the mere presence of my hand had him throbbing. “So, let’s see here: this looks like it should give us an answer.” There was a minor amount of variance in what sites reported as average, with some listing 5-7 inches and others being more specific, so I had determined beforehand which site would list the largest average size. Not to mention that Jimmy was probably still growing, and reading the average size for all adults would make him feel even smaller. “So this says that a normal size penis is about 6.5 inches. That doesn’t seem like that many – I bet yours can make it! Of course, most girls want bigger than just ‘average,’ but let’s just start with confirming that yours is at least normal.”
“Wait, Zoe, I’m. . I’m just not sure I want to go through with this. What if… ” he looked into my eyes with a painfully sincere expression and continued in a soft voice, “what if I still says I’m small?”
“Awwww… Don’t worry, hon, I’m sure it’ll be fine! And isn’t it better for you to find out for sure rather than wonder about it forever? Plus, this way I’ll be here with you – and you know your big step-sis always has your best interests at heart.” Silly Jimmy really did believe this. However much I was hurting him, he would have never believed I was doing it on purpose.
“Now, let’s take your shirt and pants off, kiddo. Time to get another look at you.” I pulled his jeans down to his ankles over Jimmy’s stammered objections. I enjoyed the feeling of taking control of my innocent, shy stepbrother; I loved that I felt no need to ask permission before I did such things.
Then, I slipped my fingers inside the waist band of his boxer shorts. “Maybe you should be doing a little strip tease or giving me a little show,” I teased with a laugh. “Here we go… one… .two…” I really drew out the countdown, making Jimmy’s imminent nudity feel that much more dreadful for him. “Three!” I whisked his shorts out of the way.
For a moment, I did nothing but savour the moment with a smile. I wanted to let the imbalance sink in: that I was kneeling next to him, dressed with immaculate style in a frilly yellow skirt, knee-high white socks and a low-cut striped tennis shirt. And he sitting next to me without a stitch, naked from head to toe. Nothing to to cover him, nowhere to hide. The longer I sat there saying nothing at all, the more keenly aware of that he was.
Finally I gave his balls a good grip as I let out another well-rehearsed stifled giggle. The smile on my face I made no attempt to hide. “Now then, sweetie, it’s still so tough for me to tell – are you hard yet?”
“Um… I am, kinda,” he said quietly.
“What’s that, babe? I can’t hear you.” I gripped the shaft of his cock tightly with my warm fingertips. “Oh, you DO have a tiny bit of an erection.” Another stifled giggle, and I made a show of trying to get a serious expression. “Sorry, Jimmy. You know it’s super hard to tell when you’re at full length. Don’t worry about it.”
I begin to stroke him with a soft, feathery touch. “Let’s just make sure you’re as hard as you can possibly get. I don’t want to short-change you here.” At the end of each stroke, I flickered my fingertips at the smooth head of his cock. Jimmy groaned, the ecstasy of my touch intermixing with his horror of being naked in front of his sexy, fully clothed sister and his sharp fear in anticipation of what the ruler might say.
“You’ll going to be so relieved once we measure you. I mean, it still looks minuscule to me, but I’ve never been good with measurements. We’ll see in a moment if I’m wrong about your pee pee being tiny.” I knew I could afford to be meaner at this point, with my expert stroking rendering his brain nearly useless. If he really stopped at thought, he might not have stood for it, but right now, all he wanted was for me to continue jerking his throbbing erection. “You have such a cute baby boner, little brother” I whispered. I massaged his tingling testicles with my free hand.
“Okay, Jimmy, time for the moment of truth.” I reached for the printer tray and pulled out our doctored ruler pic. He looked nearly ready to blow his load, and I’m sure he wished I had forgotten all about the measurements. Still, I had given him as much reason to be optimistic as fearful – I wanted my sweet little Jimmy to be even more crushed by leaving him some false hope before devastating him.
“Wow, you’re so hard,” I said. “I hope you measure up.” I pressed the ruler firmly against his rock hard dick. Jimmy’s penis in reality looked to be about five and a half inches – on the lower side of average, but very much within the normal range. But against the trick ruler I was measuring him with, that 5.5 translated into just over 2.5 inches.
“Oh my gosh, sweetie,” I said with disappointment. My stepbrother had his eyes clenched shut, not being able to bring himself to look. But I wasn’t going to let him off the hook that easily.
“Sweetheart, I think you’d better have a look.” I scooted him over in the chair and sat beside him. Finally, he opened his eyes and had no choice but to examine the ruler placed next to his rigid erection. I whispered directly into his ear: “Jimmy, you have a two and a half inch dickie.”
He gulped, having no idea what to say. I could feel his heart pounding. He looked like he couldn’t believe it (of course, he SHOULDN’T have believed it, but it was hard to argue with the number on the ruler pressed right there against his cock). For good measure I brought the printed sheet up close to his face, my pinkie finger placed at the 2.5 inch mark.
“I guess I was right all along. You really do have an inadequate dick.” I continued speaking right into his ear, my warm breath raising the hear on his neck. “I”m sorry, babe. I tried to make you feel better. But it looks like you are under-endowed. Severely under-endowed. Gosh, you have like, a third the size of a normal cock.” I resumed stroking him, giving him ripples of pleasure while the heartbreaking news was still sinking in. I wanted his pleasure to always be intimately associated with his humiliation.
“Is it really… Are you su-sure… I. . ah…” He was a stuttering, stammering little mess. He didn’t know what to say, what to do.
“Oh, Jimmy, you can’t possibly still believe you aren’t tiny, can you? I mean, if you were just a bit below normal, it’d be one thing, but… Two. And a Half. Inches.” With each of those words I gave his hard cock another vigorous stroke.
Jimmy’s body gave a quake and I understood that he was on the verge of tears. “Shhh… ” I soothed him. “There, there, little Jimmy. You can’t help having a baby sized dick. You can’t help it that your manhood is more like a boyhood.” I rubbed his back soothingly with one hand while continuing to stroke him off.
“You’ve never been with a girl, have you little guy?” He shook his head. “I didn’t think so. I’m sure if you had had a girlfriend, you would already have known that you aren’t capable of pleasing a woman. It’s so lucky for you that you found out from me, your stepsister, rather than someone else. If a girl you were in love with dumped you because of the stub in your pants, it could have really hurt!”
I continued wanking him, bringing him ever closer to the edge. “You know what, babe, this really isn’t such a bad thing. The important thing is now you know for sure – you won’t have to wonder whether or not you’re small, since you know the truth is that you are small, TOTALLY small. And I bet there are ways of dealing with a tiny pee pee, right?”
He nodded, the pleasure becoming more intense. “Right! But the important thing, if you want to be healthy and find a way to move on, is for you to just accept what you have. No girl is going to like a guy with a babydick who acts like there’s nothing wrong with it; but if you accept it, I’m sure you’ll find a way to deal with it. Right?”
Less certain of this logic, but wanting to do anything so that I would stroke him to orgasm, he reluctantly agreed. “R-right.”
“So you do accept it?”
“And what’s that that you accept, sweetie?”
“Um… ” Jimmy looked lost, a frightened and broken little boy. “That I have a smaller penis.”
“Smaller? What’s that, hon? Don’t you mean a tiny penis?”
“Y-yes, a tiny penis.”
“Say it, Jimmy. This is for your own good, so you can get healthy.”
“I have a tiny penis.” His voice cracked. It was the most painful sentence he’d ever had to utter, and it came just as he was experiencing the greatest pleasure he had ever felt.
“You have a tiny little penis,” I told him. “The thing between your legs is a nub. It’s a shameful dicklette. Yeah?”
His head must have been swimming, but the matter of most importance was no doubt that his full, aching balls were on the edge of exploding. I didn’t need to prod him to repeat after me, just ease my strokes ever so slightly so he got the idea. “I have a nub between my legs,” he exclaimed. “A shameful dicklette!” He was so caught up in the wave of pleasure from his oncoming orgasm that he shouted that crushing statement with vigour.
The stroke of my hands got faster as I felt the hot semen become ready to burst forth, but my uttering’s in his ear got slower, my voice huskier. “Cum for me, sweetie. Go ahead and shoot a load from that inadequate micropenis of yours. Tiny, tiny little man. Come on, my baby-dicked little brother. Come from your itty bitty widdle wee wee.”
I timed it perfectly so that his explosive, unbelievably intense orgasm came just as the cruellest, most dehumanising words were hitting his ears. He ejaculated, load after bitter-sweet load shooting from his cock. Never before had my little step brother felt so much ecstasy or so much humiliation.
“Clean up your mess,” I ordered in a sweetly severe voice, filling him with an extra dose of shame before the aura of his painful orgasm had faded. My victim’s shame had me incredibly turned on, and I had a feeling it was only going to get worse for poor Jimmy.