I played a prank of sorts on the little brother of one of my friends' when I was at his house studying for exams way back in the tenth grade. This was one of my more naughty stunts, and I still laugh thinking about it. I bet you'll laugh too.
I'll link to a much earlier story that also would count as a naughty prank. This is probably my 23rd story posted here!(And yes, they are all true. I guess I had both an overactive sex drive and a good memory as well)
In High School I took final exams very seriously, and religiously I would schedule joint study times before every exam with Vince, a very smart but nerdy bookworm-ish friend of mine. Vince and I didn't do anything else together socially but study. He wasn't into sports, fixing cars or even being outside at all. An early-maturer, by tenth grade Vince already had the beginnings of a receding hairline and a pronounced purplish five o'clock shadow every day by the end of classes. He was skinny as a rail, with unbelievably hairy arms and legs, almost like a monkey. But Vince aced every exam, and he was glad to study together, so as finals approached in tenth grade, as usual I found myself together with in Vince in his family room with our books spread out across the table.
Vince had a little brother named Kenny. While Vince was serious, unfunny and overly-mature, almost like an old man in training waiting for the rest of us to catch up to him, Kenny was quite opposite in every way. He was a little sprite, silly and playful and still a tiny little guy, barely 13 and in the seventh grade. Kenny kept showing up while we worked, inventing a million excuses for needing to be in the room with us. Vince would become visibly irritated, which caused Kenny great delight, as he would goad Vince into chasing him around the room, his face red with anger. Kenny would lightly hop away, causing Vince to get even angrier, till he finally caught Kenny, pummeling the laughing boy with his weak thin wristed, hairy knuckled fists.
My own brother Tad was several years younger than Kenny, and while I certainly understood Vice's frustration with Kenny's annoying behavior, I also enjoyed watching another set of brothers fight it out, with me able to sit back and take the role as the amused spectator.
Rubbing his bruised shoulder, Kenny still smiled as Vince ran up the stairs to find his mother, to ask her to act as warden in this real life drama. He wanted Kenny out of the room, and he had learned enough not to get into trouble himself by hurting Kenny in a way that would make his mother angry at him instead.
Kenny's eyes sparkled with glee as he sat next to me on the sofa. Kenny was a naughty, horny boy, Vince had told me with some disgust. Always trying to peek in girls' windows or up their skirts, and owning a hidden stash of Playboy magazines, Kenny seemingly bordered on a fixation with sex. While overtly disgusting to Vince, this knowledge of Kenny's habits was intoxicating to me.
Left alone in the room with Kenny, I started asking him questions. Delighted at my undivided attention, Kenny moved closer to me and bright eyes shining eagerly answered them all. I knew Vince wouldn't be gone long, so I honed right in to my target.
'You like Playboys?' I asked Kenny.
Kenny's breath caught in his throat as he suddenly stopped laughing and just froze. I'm sure the thoughts raced through his mind... as to if I was simply idly asking if he liked looking at Playboys, or if I had somehow learned that he had a stash, and he must have wondered what I intended to do with the knowledge. 'Vince told me you have them.'
'Yeah, I have some', Kenny admitted in his high, reedy voice, blushing slightly starting with his ears first.
'I like them too', I said. This wasn't a lie. Though I definitely preferred boys to girls, I was so horny all the time myself that sometimes I liked looking at the naked girls in men's magazines while I jerked off. Sure, I would have preferred magazines with naked guys, but I was unaware that anything like that might exist, and wouldn't have taken the risk of being caught dead with them if they did.
'Really?' said Kenny, suddenly interested, his voice turning husky. 'What do YOU have?'
In vivid detail, I began to explain what magazines I looked at, explaining the women in graphic ways, allowing my language to become more and more lewd and pornographic, unnecessarily explaining every scene in explicit detail using language that was doubtlessly highly erotic to him, and I watched Kenny's eyes grow big and round. I clearly had him hooked, and I saw his hand involuntarily brush his crotch as he nudged his (probably) stiffening penis through his pants. I knew Kenny's type, because he was an awful lot like me, I wagered, just younger: easily aroused, and then once excited he wouldn't think so clearly any more. I truly disliked this part of myself... because I wanted to be in control always, but even as a young teenager I feared that I was far more sexually compulsive than other, normal boys. Therefore, knowingly teasing Kenny like this gave me a twisted edge and a forbidden sense of power over him.
'I especially like the ones who have their legs spread just a little so you can see the inside pink part of their pussy', I suggested softly, licking my lips slightly. ' I like it when they tease you by showing you a little bit more pink pussy each time you turn the page to the next one...'
Kenny was getting lost; I could see it in his eyes and hear it in the slightly ragged way he was beginning to breathe. His eyes had glazed over as he imagined the sights that I described. Unconsciously he rubbed at his crotch, and I'm sure he was erect inside his pants. 'Yeahhhh...' he said, imagining the sights I described, the tip of his pink tongue emerging slightly from between his teeth.
'I like to jerk off and come just when I turn to the last page, where you can see everything down there and how luscious and wet it is...'
I had played this card intentionally, putting it on the table, and simultaneously causing his little brain to go into sexual hyper-drive. 'You jerk off when you look at them too, right Kenny?' I asked He stopped staring into space and looked at me intently, his mind registering what I had just said.
'Ummmm... I don't know...', stammered Kenny. He feared a trick, I'm sure.
'Sure you do,' I said. 'It's OK to tell me. I know you do.'
'Maybe I do,' said Kenny suspiciously.
'Oh, I'm sorry!' I apologized. 'I shouldn't have said that. You are too young to know about that stuff. I shouldn't talk to you about that because you are just a little kid. Please just forget I said that, OK?'
Suddenly defiant, Kenny spoke up, 'I can do it! I know about it!'
'No,' I said, turning away. You are just a little kid. 'I know you can't do it yet.'
'Yes I can! Insisted Kenny. ' I can cum! I can!'
Amused by my game of manipulation, I turned towards Kenny and said slyly, 'I don't think you can. Can you prove it?'
'How?' asked Kenny desperately, his burgeoning manhood threatened.
My eyes narrowed with the devilishness of my plot. 'If you really can do it, come back here before I leave with your cum on your hands and show it to me!'
He made a sharp intake of his breath and drew back, fist against his open mouth. 'Ewwwww! That's gross!' squealed Kenny.
'Just as I thought. I knew you can't do it,' I said tauntingly, looking away.
At that moment Vince returned to the room with his rotund mother in tow. 'Get him out of here, Mom!' ordered Vince shrilly, pointing a bony, hairy finger in Kenny's face, his protruding Adam's apple bobbing up and down in his roughly shaven skinny throat as he talked.
'Kenny,' said their Mom sweetly as she flounced across the playroom. 'Please come upstairs and leave the big boys alone.'
Kenny followed her and left the room, but not before shooting a nasty glance back over his shoulder at Vince. His neck still red with residual anger, Vince turned again to the textbooks. 'He is such a little asshole. I hate him,' Vince said.
We continued our studying, but less than an hour later Kenny's little face appeared in the stairway again. Vince whirled, but before he could even react with anger, Kenny looked at me, and thrusting his open palm towards me he said, 'See!' The center of his palm was wet, coated with thin sticky goo, and I was shocked realizing that he had taken my dare; that he had jerked off into his hand, then had quickly brought his little emission down to show me, just to prove he wasn't a baby and that he could make cum.
'See?? SEE WHAT???' yelled Vince. But Kenny ran away and was gone. My face burned red, and Vince turned to look at me. 'What did he show you?' I was at a rare loss for words. Pressing me, Vince realized that there was something going on that he wasn't a part of, so I flat out told him.
Vince regarded me with total disgust. 'That crosses the line!' he told me. 'That is so gross! You shouldn't have done that, Brad.' I knew he was right, and I tried to imagine how I'd have felt if one of my friends played that trick on my brother Tad, but I couldn't begin to do it. But truthfully, I wasn't really sorry about it, not even a little bit.