Jack’s Little PP
A Fictional Story by Gayman33.
One day, after class, we were all in the locker room (about 15-20 guys), getting dressed for our afternoon classes, when another student, Bobby, a muscular black jock on the basketball team, decided to give Jack a hard time. As we were getting changed, he snatched Jack’s underwear out of his hands and held them up to the whole class.
“Yo, you see this? Jackson still wears tights-whites,” he laughed, holding them up to the whole room, while Jack embarrassingly tried to cover himself with his gym clothes. “Hey man, why you wear these little boy panties?” Bobby continued to tease.
“Come on man, just give them back,” Jack pleaded with him. While most everybody laughed.
“Naw man, I bet you wear these because you got a little shrimp dick, don’t you?” Bobby asked, playing the room for laughs. “Show everyone, and you can have em back.”
“Please, can I just have my underwear back?” Jack pleaded, reaching for them.
Bobby tried to dodge, still laughing, and tried to toss them to one of his friends to keep them away from Jack. But as he did this, I grabbed them out of the air. “Come on, Bobby, grow up,” I said, handing them back to Jack. “Even if he does have a little dick, he can’t help it.”
The encounter ended there as class was ending and we all had to move on. Jack got dressed quietly, and we all filed back out into the hallway.
But he chased me down. “Hey Jake, just uhm- thank you for helping me there.” He said to me meekly, not making eye contact.
“No worries, Jack, it wasn’t right of Bobby to make fun of you just for wearing boy panties.” I said, “As I said, it’s not your fault if you have a small dick.”
His face got red. “Do you really have to say that? It’s not that small. It’s an alright cock.”
I laughed. “No, Jack,” I said, grabbing my crotch. “I have a cock… what you’ve got is a babydick; I’ve seen it. But it’s not your fault; some guys are just unlucky. Anyway – I’ve got to get to class. See you later.” I walked away chuckling about the experience and figured that, despite Jack’s humiliation, it would end there.
*****
The next day, after school, I was at home when my cell phone buzzed. I opened my phone to see a text, surprisingly from Jack (we weren’t exactly friends outside of school): “Hey man, do you got a second to chat?” It said.
“Sure,” I texted back, my curiosity burning considering our last conversation.
“I don’t really know how to say this… but I was thinking, I mean, you’d know better than anybody,” his response said. “Is my dick really that small?”
“Hahahahahahah,” I texted back immediately. “That’s what you’ve been thinking about? I honestly haven’t given it much thought since yesterday. I’m tied up right now, but yes, it is. I doubt it’s more than 4 inches hard.”
“4 is normal!!”
“No, Jack, 4 is small. I’m like double that when I’m hard,” I said.
“No way. That’s like porn big,” he kept protesting.
“It’s really not. If you want to come over, I’ll show you how much bigger a real cock can be.” I said teasingly, definitely not expecting him to take me up on my offer.
“Can you meet up after 8? That’s when I get off work,” he said.
*****
Later that day
It was around 8:15, and I was waiting for Jackson to arrive at my house. I was pretty skeptical that he would come; after I sent him my address, he only texted me back an “ok” (there were no emojis back in 2009). When my phone buzzed again with a message from Jack: “Hey – my friend just dropped me off; I’m outside your house.”
The little guy actually did it, I thought to myself. “Be right out,” I texted back and headed out to the driveway to meet him. I was an only child, and my bedroom was in the basement of our house at the time. I had three rooms to myself downstairs, right off the side door, so it was easy to bring people in and out of my childhood home without my parents or anyone upstairs noticing too much fuss.
I opened the side door of the house and found Jack standing in my driveway in black jeans, an MCR T-shirt, Vans, and his hair drooping over his eye like usual. I noticed he was tongue-fiddling with his lip piercing and was a little uncomfortable as I confidently stood in front of him, just looking him up and down. “Gotta be honest, I’m surprised you came,” I said to him after a long pause. “I didn’t think you were serious about getting a closer look at my cock.”
“I really don’t know why I’m here,” he said, kind of defensively. “You were just so assertive on the phone earlier, I felt like I’d disappoint you or something if I didn’t show up.”
“Do you wanna come in? We can hang out in my room for a bit if you want. Nobody will bother us,” I told him.
He nodded and started to follow me inside down the stairs and into the public “living room” between my private bedroom and bathroom in the basement. I remember South Park was playing on the TV when I invited him to sit on the couch.
“Jack, you can relax, little guy. I’m not going to make you do anything you don’t want to do or anything.” I tried to ease his nerves a bit. “I’m not really sure why you texted me earlier either…but you’re here, so we can just hang out if you want.”
“You stood up for me,” he said quietly, his eyes cast downward. “With Bobby. Why’d you do that?” He asked
“I don’t know… he was bullying you for no reason; it didn’t feel right. I guess I didn’t think about it all that much.” I answered honestly. “Plus, I like a boy in briefs. I wanted to see you put them on.”
He was quiet for an extended pause and then said, “I wouldn’t have minded so much if he wasn’t so right. I know my dick is little. I’ve seen you other guys in the locker room. But I didn’t think it was that little.”
I was a bit stunned and didn’t know what to say; this was the first time I’d been in a situation like this. He was confessing a legitimate insecurity to me, and I wasn’t sure if I should contribute to the discussion. “Well… it’s not like micro or any-“
“You’ve seen lots of dicks, right?” He cut me off, finally looked up, and made eye contact with me. “Being gay and everything…”
“Well, I don’t know about lots,” I said jokingly, “but yeah, I guess I’ve had more up-close experience than the average guy in our class”
“I wanna see how much bigger you are than me,” Jack said. “What do I have to compete with?”
“Uhh, Jackson buddy… you might not want to compare yourself to me,” I said. “Given my limited experience, while I can say for sure that you are below average, I’m also above average, so it might not help.”
“Please? It’s all I can think about these last three days, honestly,” he was basically pleading with me.
I looked around the room and nodded my head. “Alright – I’m a little chubbed from this conversation, to be honest,” I said, undoing my belt. “You sure you wanna see it?”
“Yes, please.” his eyes were locked on my zipper by now.
“Ok” I shrugged and pulled my cock out of my pants. Half hard, it was around 6.5-7 inches.
“Oh, my god. Wow. That is really huge,” Jackson said.
“It’s really not that big, a little more than average. Honestly, yours is just so small that it seems big,” I said to him. I waited a beat and said, “Do you want to touch it?”
“I don’t know,” Jack said, never once taking his eyes off of my cock. “What would I do?”
“Just come over here, and get on your knees in front of me. You can grab it with both hands.” I showed him.
“On my knees?” He said.
“You’ll get a better look from there.” I teased. I didn’t know how far he was really going to go, but he was a cute guy staring at my cock so I figured I’d push it.
Jackson moved off the couch and onto his knees almost instinctively, his hands reaching up to grab my cock. I put my hand on the back of his head to move his face closer to my cock, and I saw a look in his eyes that I would go on to see in the eyes of so many cocksuckers after him, the look of just awe and excitement as he felt the weight and girth of my cock in his hands.
Jack looked up at me from his place on his knees, holding my rapidly hardening cock with both of his hands. His light blue eyes fogged over with lust, confusion, and amazement. “It’s so big,” he said barely above a whisper, like he was talking to himself.
“How does it feel? Different than you expected?” I asked.
“I….I don’t know, I didn’t know what to expect,” he stammered. His gaze locked directly on the head of my dick, and his hands somewhat involuntarily jerked me as he kept shifting his grasp between both his hands. “It’s heavy.”
“Just smack it on your hand a few times,” I said, “that way you can really feel the heft behind a real big cock.”
Without any more direction, Jack repositioned himself directly in front of me, on his knees but sitting back on his butt so he was fully underneath my cock. Then with his right hand he lifted it and slapped himself in the cheek with my dick three or four times. “Jesus, I feel like you could knock me out with this thing,” he joked, the nervousness he was feeling clear in his voice.
I laughed and put my hand back on the back of his head and said, “Just don’t hit yourself too hard and you’ll be fine. Here, let’s try this…” I narrated as I moved his hand and laid my now fully hard 8inch dick across his face. “Look at that man, my dick is almost as big as your whole face.”
“I wonder…” he mumbled to himself, picking it up again. “I wonder if I could fit it in my mouth?”
“That’s what you’re thinking about?” I said with a huge smile on my face. “Why don’t you try and find out?”
“I… don’t know what to do,” he said. “What if I do it wrong?”
“You can’t possibly do it wrong,” I told him. “Just put as much of it in your mouth as you can, use your lips and tongue and not your teeth, and just have fun.”
After a second or two of hesitation, Jack took my cock in his mouth, two inches, then three, four… he started to struggle, gagging himself a little bit. I could see the tears welling up in his eyes, but he seemed committed, so I decided that just some encouragement might do the trick.
“You’re doing a great job, little guy, really making my big dick feel good. Keep going.” I put my hand on his head again to guide him and help with the rhythm. “Don’t be afraid to be a little rough; you’re not going to hurt it.”
He kept sucking me off for another few minutes, and I noticed he had his eyes closed by now and seemed to really be getting into it. He was steadying himself against my thigh with one hand and palming his own little dick through his jeans with the other. I took my hand off his head and let him just go to work; he was loving it.
“Is sucking my dick making you hard, Jacky-boy?” I teased him. “That’s ok, stand up and take your pants off.”
Jack quickly stood up, took off his shirt, and pulled down his jeans and underwear, again rocking the tightly-whities that had started this whole affair.
“You know, I think it’s cute you still wear the briefs,” I told him. “And look, you’re rock hard, man. Now is the perfect chance to compare if you still want to.”
He stood in front of me and held my cock in one hand, and his little pp in his other hand, looked down at them, and back at me. “fuck, why do I like this so much?” He asked me.
“Honestly man, I don’t know. But if it feels good, keep doing it. Did you like sucking my dick?” I asked him
“Yeah… I think I really did.”
“Well then… why don’t you finish what you started?” I smirked at him, gently pushing down on his shoulders.
Now he was seated on the edge of my couch, my cock back in his mouth, and he was working it the best he could.
“Go ahead and jerk yourself while you suck me if you want,” I told him.
His hand immediately went to his hard little 4inch peter, jerking himself with just his thumb, index, and forefinger.
“No way that’s how you jerk off?” I laughed at him. I couldn’t help it; this was the first time I’d ever seen someone do a two-finger tug like that. He was obviously embarrassed because he stopped jerking himself right away. “No, no, don’t stop,” I said. “I want to see how you jerk your babydick.”
He kept going on himself, while trying his best to get more and more of my dick in his mouth. For a first timer, he wasn’t bad.
“Ohh fuck I’m going to cum” I said, pushing him off of my dick and onto his back on the couch. I stood over him jerking off while he tugged himself. I took a step back so I could purposely cum all over his hand and little dick as I erupted. “Fuuccckkkkk that’s it Jack, use my nut as lube for your little pp” I remember saying just as he came as well.
A minute passed, and our heart rates slowed. This is the moment I expected some clarity to return to him (and me). I knew that he’d definitely never done that before, so I tried to be tactful.
“I’ll get a towel, just stay there,” I said
“No,” Jack jumped up, covered in both mine and his cum. “Can I just use your bathroom?”
“Yeah, of course,” I said. Showing him where it was, and giving him a towel anyway.
He stayed in the bathroom for some time. 10-15 minutes before he reappeared looking for his clothes. “You’re…you’re not going to tell anyone about this, right?” He asked me sheepishly.
I laughed. “Have you ever heard about any of the other guys in our class I’ve done this with?” I asked him.
“No”
“Well, then you know I can keep a secret. Go ahead and get dressed; I’ll give you a ride home whenever you’re ready.”
The End.
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