Date: Sat, 8 Jul 2023 13:08:33 -0400 From: Lee Wilson Subject: My Roommate Teaches Me - Chapter 18 This story is an original work of gay fiction. None of the people or events are real. While some of the town names used may be real, any other geographic references (school, events) are purely fictional. Any resemblance to persons living or dead is completely coincidental. This story depicts sexual situations between minor males. If reading this is illegal where you reside, or you are not at least 18 years of age, you are reading at your own risk. This work is the property of the author, Lee R Wilson, and shall not be reproduced and/or re-posted without his permission. Story ©2023 Lee R Wilson. If you enjoy this or the other stories here, why not donate to keep the fun alive? Donate here: https://donate.nifty.org/ My Roommate Teaches Me Key Players: Domenico Martini - 12 Jacob (Jake) Mason - 12 Bill Nelson - 12 Rodney (Rod) Quincy - 12 Marcus King - 12 Donald (Don) Livingston - 12 Gene Jones - 12 Jerry Williams - 12 Supporting Characters: Jim Parkins - 17 - Dorm Floor Monitor I realized in the previous chapter I duplicated the date. Jerry's arrival should have been October 23. Corrected from here forward. (LRW) From Chapter 17 "Go ahead. Prove it's all true." I reach out and take hold of his dick. I start rubbing it because he isn't hard yet, but he's 12 like the rest of us, it doesn't take much to get him hard. I figured he'd say I could stop after I grabbed him and fondled him a little bit. He's got his eyes closed, head back, and is enjoying it, so I keep going. I mouth 'tissues' to Jake because I know it won't be over until he cums. Jerry gets rock hard and I'm stroking his cock. I speed up, slow down, squeeze, release. About a minute after he's hard I feel his dick start to throb so I shove the tissues in front of it, so a) none gets on the floor, and b) he doesn't cum on my face. He starts shooting, probably about 5 spurts go into the tissues. "Ohhhhhhhh, Goddddddddd." He looks like he's about to collapse. Fortunately Bill shoves a desk chair under and behind him. Otherwise I'd have been holding him up by his dick. "Holy fuck. You were right Don. That was fuckin' awesome. Shit you really weren't lying. The old Rod wouldn't have even touched me. Probably turned around half a second after my pants were down. Oh, shit, they're still down." He hurriedly stands and pulls his underwear and pants back up. Now he's embarrassed, having been jerked off by a guy in front of everybody. "Hey, it's cool Jer. Like Don said, we've all done it. No need to feel like you need to crawl into a hole. We're all friends here and this shit doesn't leave the room. Nobody else is gonna know." "Um. OK Domenico. I didn't expect him to do it, but once he started, I couldn't bring myself to stop him. I'm sorry I made him do that in front of you all." Everybody reassures Jerry it was OK, even that it was hot and got the rest of them boned up. I admitted I got hard too. "OK. I just need to sit here and digest this. I mean it was a first for me too. Um, thanks Rod. That did feel really, REALLY good." "Yeah, um, you're welcome. Don't make a habit of it, he he." Jake acts as social director again. "I say to celebrate Jerry's first day here, and first hand job, we head to the pool. Wink, wink." CHAPTER 18 - Jerry Fits In and More Time Goes By It took a few minutes for Jerry to sort through his stuff. Fortunately it was delivered. I joked he'd have to swim naked if it wasn't there. I'm not sure he hated the idea. Anyway, we swam for almost two hours then headed to the showers. Even though it's Sunday afternoon, there's one kid in there. He's in one or more of each of our classes so we all kind of know him. He looks embarrassed so we figure we almost caught him wanking. He's covering himself up but we already saw he was hard. Leave it to Jake to break the ice. "No worries Ken. We were about to do the same thing." "All of you?" "Yeah. You never jerked off with friends?" "Uh uh." Jake takes off his swim suit, the rest of us follow suit. Don isn't hard yet, neither is Gene, but that doesn't last long. We all start jerking off. Ken is just staring at us in disbelief. DM tries to guilt him into joining us. "Just staring is gay, joining us is cool." "Huh? Oh. Um. Maybe I'll just leave." "Suit yourself, but I bet you were doing that here so you wouldn't have to do it in front of your roommate." Ken looks undecided regardless of DM's prompting. Finally he uncovers and starts rubbing. "See was that hard? Well, yeah, I guess it is hard, but was it so difficult to start back up?" "Um. No." He obviously doesn't want to talk and wank, so we all just keep at it. We all keep our hands to ourselves. We all know that if we didn't it would scare him off faster than vampires and zombies. One by one we all cum. After a couple of us do, Ken lets go with a shot that has to go 4 or 5 feet. "Whoa. Way to go Ken. Next time aim better, you missed me." "Oh, yeah. You're Domenico, the, um..." "The gay one. Yep." The rest of us finish off. We all walk back to our rooms, naked as usual. Ken starts to put his underpants on, but stops after we all start walking out naked. He walks into 207 naked. Just before the door closes, we hear his roommate. "What the fuck Ken? Put some clothes on." We all laugh and go to our separate rooms. I help Jerry put his stuff away and we sit down and catch up with each other. We do put clothes on first. We both think it's a little much to hang out naked. Wanking in the shower is one thing. Plus I think he's still a little uncomfortable about my jerking him off earlier. Well, he asked for it. Monday October 24 We'll leave Rod now and visit once again with Domenico and Jake, from Domenico's perspective. It's after dinner and they're alone in their room. "Jake, now that things are a little settled down, what do you think about us making love?" "You know I want to DM. I just worry about hurting you." "I can handle a little pain, knowing the pleasure is coming." "OK. But I'm going to stop if I think it's hurting you too much." "That's fair." Of course I'll do my best to hide any pain. Jake has fingered my ass a few times since we got the lube, so I can handle some stretching already. We strip and he lubes up my ass and puts in one finger. Not a problem yet. He slides in a second and I flinch a little. "Still OK?" "Yep, each finger takes just a little getting used to." "OK, here comes number 3. This is where you usually stop me." Usually, not gonna happen tonight. I hope. He puts in the third. I flinch again, but it's really not so bad. "Just a little flinch, but you didn't clench your ass muscles this time. I'm going to work them in and out now." The pain is subsiding. It's actually starting to feel good. I moan. I hope Jake doesn't think it's from pain. "Feeling good I guess?" "Mmmm hmmm." "OK, I'm greasing weezer." "Huh?" "Lubing my dick. I'm going to start putting it in as soon as I pull out my fingers." "OK, I'm ready." I hope. I feel the shift from fingers to having his cock right at my anus. He pushes a little. Oh, fuck that hurts, but I try not to let it show. He's partially inside me. Finally. "Doing Ok?" "Yeah, just give me a second." "Just say when you're ready for me to try to push in more." I wait about 10 more seconds before saying OK. He pushes in a little more. It hurts, but not as bad as the first bit. "Still good?" "Yeah. That bit didn't hurt as much. Keep going." We continue like this for a few more minutes and then I feel his pubic hair on my butt cheeks. "You're all the way in." "Yep. Still good?" "Yeah. Start moving out again slow." Jake pulls back a little. After a couple inches with no howl of pain from me, he pushes back in. It's starting to feel better, almost no pain at all. He repeats the out and in motion again. I actually moan with pleasure. "I'm going to speed up just a little." "Oh God that feels good. Keep going." Jake is actually fucking, no, making love to me. "God, your ass is so tight, I'm not going to last long." "That's OK. We can run the marathon another time. It feels good. Go a little faster. I want to feel your cum shooting into me." Jake speeds up a little more. Another 30 or so more seconds and he's grunting. I feel his dick expand inside me and then a warmth fills my insides. Yes, he's cumming in me. "Yessss. I feel you cumming. Oh God, it's so awesome." He stops thrusting and just rests deep inside of me. "It felt awesome to me too. I'm going to let it shrink a little before I pull out. I don't know if it will hurt too much if I pull out fully hard." "That's fine. The longer you're inside me the better." After a minute or so, I feel him getting smaller. He starts sliding out slowly. I think, noooo don't go. But nature refuses my silent request, and he leaves me with an empty feeling. "Mmmm, that was nice, except the part where you pulled out. I wish you could have stayed inside me longer." "Me too, but I kind of didn't have a choice." "I know. Kiss me." We kiss for a few minutes and then he asks 'your turn?' "Yes. I want to try to make you feel as good as I did. I hope I'm big enough." "You'll be perfect, I know it." He gets on his back and pulls his legs back like I was. The first finger doesn't bother him a bit. A small flinch with my second finger. I think he's been ready for me to enter him for a while now, but he knew I wanted him first, so he's been patient. As I push in my third finger, I start lubing my cock. "OK. Making the switch now." "Go ahead." I remove my fingers and push in the head of my dick. He flinches a little, but I can tell it doesn't hurt him as much. "Nice. Keep going. Slow." I push in some more, but it doesn't take me nearly as long to push all the way in as he did. "I feel you up against my cheeks. It feels good, give me just a bit to get used to the feeling." "OK, just say when." He waits what seems like a long time but is probably less than 30 seconds. "OK, go ahead and pull back a little." I do as he asks. It's really tight in there. It feels like I'm not sliding out easily, but I look down and I am almost all the way out so I stop. "Push back in, I hardly feel you anymore." "Sorry, I almost pulled all the way out, it didn't feel like I was moving." I push back in and Jake moans in pleasure. "Oh, God you feel good. Keep going." I try to pay a little closer attention to how far back I pull, trying to keep half my dick in him each time I pull back. "Faster." I speed up a little as requested. "Faster, push harder. God it feels so good." I start thrusting in and out faster and harder like he asks. It's only another minute before I feel my balls pull up and my dick start throbbing. "Oh, God. I'm cumming." "Yesss. I feel you. It's fucking awesome. Push all the way in. I want you to stay inside as long as possible." I do as he asks, but alas, like him, I start shrinking way too soon and slide out. I lean down and kiss him, pretty much collapsing on top of him. Jake nudges me a short time later. "Wow, did I fall asleep lying on top of you?" "You did, but it was nice feeling the closeness afterward. I think we should hit the tissue box. I feel myself leaking and I'm pretty sure you are too." "Oh, shoot. Sorry." "Don't be. It's not a problem." We clean up after we separate. We move over to his bed since mine is a little bit of a mess. I'll be doing laundry tomorrow for sure. We fall asleep in each other's arms. We've all been helping Jerry get acclimated to the school. After 6+ years of public school, joining partway through the semester is an adjustment for him. He's a smart kid, but like Rod told him, the teachers do expect a lot from us. He's starting to feel more comfortable both with the school and the rest of our friends. Soon it becomes time to get ready for the Halloween party. The school provides a bunch of makeup and accessories so people can dress up somewhat if they want. Some kids even go out and pick up real costumes. We all think that's a little beneath us at this point so we all paint each other up as bloody victims of an ax murderer. At first we joke that Don should be the ax murderer since he was so good with the ax at the park. But he passes on that idea and gets bloody like the rest of us. The initial idea was bloody accident victims, but Jake nixed that before he thought I found out about it. Fortunately they realized on their own it would have been an awful idea. Saturday October 29 Halloween is on a Monday so the school set the party for Saturday night. The 8 of us all walk into the gym together, looking like bloody messes. After a few seconds of the rest of the kids staring at us, someone decides we did a good job and starts applauding. We jokingly take bows and head for the drink table. Punch and sodas, but we weren't expecting liquor and beer. Gene speaks up first. "I have to say, we did an excellent job on each other. Although Jake, I think you need a little more blood on you." Gene had a tube of fake blood in his pocket and squirts Jake with it. Aiming for his neck so as to not hit him in the eye. "Gene. I'd kill you if you already didn't look dead." We all joke around for a while drinking and chowing down on the free snacks. After a while Dean Canton gets all of our attention. "I'm glad to see you're all having a good time. This is kind of a tradition here, so I want to take this opportunity to hand out a few awards. Nothing too valuable, consider them status symbols." They're hardly even that. School notebooks, mechanical pencils, things like that. Although there is one pretty big box that nobody can tell what it is. "OK, we'll start with the funniest costume/makeup. That goes to 8th grader Tim Stone. Tim, come on up and pick a prize. Not the box." After handing out prizes for things like ugliest, geekiest, and a host of other, mostly stupid categories, the Dean has only the box left. "The last prize actually goes to a group of, um, quite resourseful, not to mention gross, students. The prize for the goriest costume/makeup is an 8-way tie to the walking cadavers from the second floor of dorm 1. Gene, Bill, Marcus, Don, Domenico, Jake, Rod, and Jerry, come on over and see what's waiting for you in the box." It's way better than the crap everybody else got. A case of 24 cans of monster in a variety of flavors. We get another round of cheers as we show what we got. "Enjoy the food and drinks. Have a good time. Curfew is midnight tonight. Anybody breaking curfew has to clean this mess up tomorrow." He sounds like he's joking, but we all know he's serious. The place is already a mess, so everybody takes the threat seriously. We didn't plan on staying that late anyway. Our plans included a shower to get all the fake blood off of us and then an iPad porn night in room 208. It's Jerry's second, but it's not one he'll forget for a long time. We'll move back into Rod's mind for this piece. We finish in the shower and head back to Jake and DM's room. Naked as usual, although this time there's more of a reason to be naked returning from the showers than usual. We all find a place to sit while Jake cranks up the iPad. Gene says he has an announcement to make. None of us could have ever expected what he was going to say. "So, um. I really want to thank you guys for bringing me into the group. I've always been a bit of a loner, and when James was picking on me, I really thought about hurting myself before I finally broke down and told on him. I mean, really hurting myself. I don't want to say what I mean, but I think you guys know. Even after that, I was so lonely, I wasn't sure I could go on. I've been thinking of a way to repay you guys, while at the same time do something I've always wanted to do but was afraid to..." He hesitates for a couple moments, apparently preparing himself to say what he wants to say. "OK. You guys know that I've considered myself bisexual for the last little while. That's not really true. I am indeed gay. One of the things I've always wanted to do was, um, give a bunch of guys blowjobs." Like I said, nobody expected anything like that, so we're all kind of shocked. "I like you guys a lot, and not just for helping me fit in. Watching you all jerk off, and sometimes being jerked off, more and more I've wanted to suck you all. Jake and DM, I realize you're boyfriends, so if you don't want me to, I understand. But understand that this is really something I want to do. I'm not forcing anybody obviously, so say no if you want. But I hope at least some of you will let me do this." The shock is wearing off and the little heads around the room are starting to take command over the big heads. Gene is waiting for someone to say something, watching us all get hard. Nobody seems like they want to be first, so I volunteer. "Gene, since I was the first one to offer to jerk you off, I'd be honored to be first in line." "Are you sure Rod? I kind of thought you might be the last to want to get sucked off by another guy." "That was the old Rod, Gene. Plus, I don't think anybody else was going to step up to be the first. I may not have been in the first group to bring you in, ass that I was at the time. I hope you consider me enough of a friend to let me help grant your wish." "Thanks Rod." Gene moves over and kneels in front of me. Somehow I get even harder than I was. Gene leans down and licks my cock. He surprises us all again with his moan of obvious pleasure. He then licks my balls. I spread my legs more to give him better access. Releasing a moan of my own almost without realizing it. He takes my cock into his mouth. It's so awesome that the fact that it's a boy doing it doesn't phase me in the least. I've never gotten a blowjob before, so I don't know if it's a good one or not. Then I figure it's like pizza. It's got to be really awful to be bad. It's not awful. I can tell Gene is enjoying this as much as I am. He's moaning just as much as me. I let him know I'm getting close. "I want to swallow everybody's cum. Please, do it." Hearing that sends me over the edge. I'm thrusting and shaking so hard Gene has to grab my hips to hold on. I'm cumming in someone's mouth for the first time and it feels like I'm never going to stop. I feel Gene swallow and that sends one last shot into his mouth. He swallows again, pulls off my dick, looks up at me, smiles and thanks me. Shit, I should be thanking him, but speech is beyond my capabilities right now. Gene gets up and looks around the room, hoping someone else will speak up. Don hesitantly raises his hand. Gene quickly moves in front of Don and starts on him the same way as with me. I guess he figured stick with what works. It's apparently Don's first as well. He's got his eyes clamped tight, looking like he's fighting hard not to cum. It doesn't take long before he's shuddering, losing that battle. Marcus is next. While Gene is working on him, Jake and Domenico lie down on Jake's bed. Jake pulls his legs up and DM somehow got a tube of lube and is greasing up his cock and Jake's ass. They're not waiting for Gene's blowjob. Marcus is staring at DM's dick sliding into Jake's ass. He shudders and cums too. Gene gets up, looks over at Jake and DM, smiling. Jerry doesn't know whether to look at the fucking or Gene, but he looks toward Gene and nods. Gene kneels in front of him and Jerry goes back to watching DM fuck Jake. He's pumping in and out of Jake's ass slowly, trying to make it last. His face contorts and he speeds up, grunting a few times as he's obviously cumming inside Jake. That's all it takes for Jerry who starts cumming in Gene's mouth. Giving him his fourth drink of cum. Gene gets up, looks over at Bill, who nods. At the same time, Jake and DM have switched positions. It's almost like a previous iPad porn night with the guy with the big dick putting it into the tiny guy's ass. Somehow DM takes it all after a minute or so. As soon as Jake is balls deep, Bill grunts, filling Gene's mouth once again with cum. Gene watches Jake fucking DM for a moment, looks over at me, seeing I'm hard again with all this going on around me and comes back in front of me, smiling. I smile back and nod. Once again, my cock is buried in Gene's mouth. I don't last a whole lot longer this time, but I see Jake's body stiffen and he grunts, filling DM's little ass with cum and I give Gene a second dose of my cum. We all just sit for a moment recovering and digesting what just happened. Gene is the first to speak. "Thanks everybody. I love you all so much. I hope I'll get another chance like this. Maybe not all at once, but even one or two at a time, whenever you want." I'm starting to rethink my idea of Jake being the king of the pervs. Gene is quickly closing the gap. Next up - "Thanksgiving at the Mason's and a Surprise" Author's Note Feel free to drop me a line if you haven't already. I appreciate the comments, good or bad. If you liked this, check out my other stories on nifty: https://www.nifty.org/nifty/gay/young-friends/look-but-dont-look/ (Complete) https://www.nifty.org/nifty/gay/highschool/high-school-cum-boy/ (Complete) https://www.nifty.org/nifty/gay/young-friends/the-gay-boys-of-brumfeld (NEW) LRW