Roommates Stories: Warren
I've had a lot of roommates from when I first went to college until I moved in with my partner. In that time I've had a number of sexual experiences with them and wanted to share them here.
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Warren (Sophomore Spring Semester)
Warren was both my first college crush, and my first best friend in college. I had an English elective my freshman year when I was mistakenly studying Pre-Med, and he was one of the only other guys in the class who would actually speak during discussion. He was a big fan of Vonnegut and Hemingway and all my teenage angst dreams were fulfilled. Warren had these bright blue eyes and what seemed like a perpetually sad puppy-dog look on his face, but maybe it was just the 9AM class start time. He was a smoker, always lighting up a hand-rolled cigarette right after class, and for the first time that wasn't a turn-off for me. I struck up a few conversations on our way out of class but I always found it hard to make friends with another guy without outright hitting on him. I also was 90% sure he was straight.
At one point that semester he shaved his head, which made his ears stick out like Mickey Mouse. He got in the habit of wearing a flat hat (or scally cap, newsies hat, I never know what to call them) which definitely added to that hipster vibe everyone was aiming for in college at the time. I teased him a little bit about his hair, and he admitted that his roommate and him had gotten drunk on Southern Comfort and it seemed like a good idea. I mentioned that I liked SoCo too, and he invited me over to finish it off with him at some point that week. That Friday I made myself up to look as casually attractive as possible, headed towards his dorm, and was hoping for a night of drinking and talking literature with a cute guy. Unfortunately, his roommate was also around and the two of them were inseparable. At some point there was a dumb "we're so gay" joke going on between them, so I realized I was wishing for the wrong thing and left.
Warren and I actually became good study buddies as that English class got much harder after midterms; we studied together and helped edit a few papers of each other. He was one of the few friends I had at the time who wasn't convinced that they were smarter than everyone else, and that was very refreshing for me to have. Towards the end of the semester, I actually started smoking one of his hand-rolled cigarettes and I felt comfortable enough to come out to him. He had gotten away with talking about hot girls in class for long enough, so I mentioned Casey, a very tall and athletic blonde rower in my pre-med class. Warren looked surprised and unfazed. He mostly just gave me shit because Casey was outright one of the dumbest jocks on a campus that didn't pride itself on athletics.
That following semester we didn't have any classes together, yet we still made time for each other. Warren had a habit for picking up large handles of booze, then his roommate would disappear, so he'd invite me over to drink and smoke and talk literature, or philosophy, or life. In the later part of spring when I was fucking Steven, he also became a sounding board because they weren't friends, so I could talk about what awkwardness it is to fuck your roommate. He agreed there was a big personality clash but he surprised me with a frank assessment: "Honestly, if my roommate would help me cum then we could just go back to being buds, I'd probably take him up on it for the convenience." I filed this away, but mostly attributed it to the vodka.
Warren's roommate, Tony, was a really unstable personality and they lived together from a random pairing at the start of freshman year through sophomore year. Tony was very energetic and enthusiastic about anything, but he was very flaky and could disappear for a while. Warren was much more laid-back, although he seemed to parrot off Tony's energy. Tony had a long-term girlfriend studying at a larger school about an hour away, and the both of them were planning to study in Europe that Spring. This created an opening in Warren's dorm room and since him and I had been spending a lot of time studying or drinking together that semester while my friendship with Steven was ebbing, Warren asked me to move in as soon as Tony was approved to study abroad.
I spent a few nights over in their room near the end of the semester, not like it was far from my own dorm, but because when Tony had his girlfriend over, her and I were a natural counterbalance to the manic-angst of Tony and Warren. One night, Tony and his girlfriend were already asleep, and a drunk Warren asked me to stay with him that night, "just to cuddle like bros". I didn't want to argue about how gay bros didn't cuddle the same way straight ones did, but it was nice to be held by a man during a cold winter night. The next morning we both slept late, and when Tony's father came to drop something off in the room he woke us up. Warren sprung out of bed to shake his hand, always so formal, while I just mumbled hello with bad bedhed. Tony told us later that his father was impressed that Warren "could get a cute boyfriend since he's a bald fucker".
Warren and I kept in touch during winter break; his parents were heading towards a divorce, his older brothers were nowhere near, and his long-term on-again-off-again high school sweetheart was moving on with another guy. I felt terrible for him and agreed that we'd apply to move back into the dorm a week before classes started. The rest of the dorm was deserted so we made the most of a January in upstate NY. We went skiing once (I hated it) and snowboarding once (we both sucked); we got extra hours at our on-campus jobs, mine in an office, his in the dining halls. With the extra cash, we tried not to blow it all on liquor, but did catch a few movies at the independent movie theatre downtown and snuck in some rum in his sheepskin flask.
That semester we had an unseasonably warm winter, and him and I could frequently walk downtown to get some nature, or culture into our routine. One night we even explored an abandoned factory not too far from campus. Climbing up the decrepit ladders wasn't too fun for me, but watching the sunset on the roof with him was a special moment. We didn't have any classes together, yet we were such great brain-buddies that we had our desks face each other to work on our writing. He even had an old type-writer that we'd write short snippets with; my favorite were dirty limericks I'd leave around his side of the room to make him blush. Our floor of the dorm was just wonderful, I made great friends with 4 of the guys in rooms near ours, and our RA was the coolest we'd ever had (probably because he was buying weed from one of us.)
Warren didn't have much luck with women that semester; well, one girl did sleep with him, and he was an asshole about it and hung her panties on the wall afterwards. I berated him for being such a sexist pig, especially because the girl and I were in a class together, and he relented. I didn't know if it was a libido thing or what but he never seemed to need to be alone in the room, and there were a few times I did have to sexile him for a hookup. The most regular guy I was with (I nicknamed him Seabiscuit because he was hung like a horse and always finished first) was the only guy Warren actually met, and afterwards he told me "you're smart and funny and good-looking, why are you sleeping with him?". I don't think any of my other straight friends gave me the ego-boost that Warren did, not that he was homely but he was about 5'7 and skinny so I think he always thought less of himself.
Warren kind of hit a spiral shortly after midterms; he was doing bad in classes, overslept too much, lost his job at the dining hall, and his parents were using him to fight. One night he hung up on his mother on the phone, and she called campus police saying he was "a danger to himself". My friends and I stayed up most of that night chain-smoking, worried about what would happen to him when he got back from Campus Police. He came in that morning around 4 and just slept until the afternoon. I gave him space during the day, but that night we had a long talk about everything going wrong. I had never seen him cry before, and he wasn't really letting himself, but I pulled him in for a hug and the tears started falling. He asked me to hold him in his bed, and I was happy to be there for him.
The next morning I woke up with Warren in my arms (both of us clothed), and I tried willing my morning wood to go down, but his warm ass up against me was too much. I tried getting up from bed, but he backed up into me and I knew he'd feel my boner against his butt. He mumbled "I know you're hard, but it feels nice to have you so close. Just stay like this for a bit." I was confused to hear this from him, but he grabbed my arms to wrap them around his chest. I dozed with him for a while until he moved my hands down from his chest closer to his waist. "Can you do this for me? Can you make me feel good?" I wasn't sure if he was fully awake or not so I didn't move, but he started shuffling and then moved my hands down until they were on top of his underwear. He definitely had a hard-on through his boxer briefs, and when I tried to move my hand he moaned my name. "Please? I need this so bad." He started thrusting his hips towards my hand, and also backing it up into my now raging boner. "Warren, are you sure?" I asked. He just gave a moan and I moved my hands down inside his underwear. His cock was hard and hot against my fingers, and as I played with the tip a bit it started to leak precum like a faucet. "Oh fuck, I'm so horny dude" he whined, and I moved my body a little closer into him and started pumping on his cock with my hand. My breath on the back of his neck, I asked him "Do you want me to jerk you off? Or do you want me to suck you off?". He gasped and said, "Please suck my dick. Please."
I moved up so he could lie on his back; I threw off the covers and saw him lying there with a tent in his shorts. He opened his eyes, took off his shirt, and I used that chance to lower his boxer briefs until they were around his ankles. Warren's cock was bigger than I expected from what I'd peeked at when he'd be in his underwear around the room, definitely a grower. He had a thick circumcised cock, not unlike my own but longer, and his was angled more upward towards his exposed happy trail. He had very little body hair except for a small patch of pubes, a light happy trail and a small tuft of light brown chest hair right in the center. In that moment, I really wanted to kiss him but was worried it would be too much for my "straight" roommate. "Is it alright?" he asked me when I hesitated. I told him it was perfect, and went right down to his groin, licking up the sides of his hard-on. He moaned, huskily, and I took that as a sign to continue so I took his head in my mouth and started doing circles around the rim with my tongue. With my left hand pumping his shaft, I moved my right hand down to his balls. They were big and warm, although conspicuously smooth like he shaved them regularly. He groaned "fuck yeah" so I pressed my right hand up against the hard spot right behind his balls. He gasped and I made sure to look up, expecting his eyes to be closed, but he was gazing right at me, making eye contact while I was sucking his cock. I started sucking him harder, removing my hand and going right down to the base. I bobbed my head up and down probably a dozen times before he whimpered "I'm gonna shoot!" and I increased my sucking and pressure with my right hand. He shot at least 8 or 9 spurts into my mouth and down my throat before I let up. His eyes were closed, face still scrunched up from his orgasm, but when he opened them he smiled and said "That's easily the best I've ever had. You're amazing dude." I smiled, pleased with my work, and got up.
Warren saw my shorts were pretty obscenely tented and said "Do you want me to help with that?" and I was flat out stunned. I really expected him to be the straight guy who gets head but doesn't talk to his cocksucker after, but instead he reached into my waistband and started fondling my stiff cock through my tight briefs. "I mean you can if you want to" I told him, unsure what was going to happen but moving closer to where he was laying in bed. He pulled my briefs down, gave a gulp, and said "I've only done this once before, so let me know if I'm doing something wrong" and immediately closed his lips around my cockhead. I was shocked, but his wet mouth and swirling tongue definitely distracted me. I put my hands on the back of his head, gently, but started to give little thrusts into his mouth. He grazed my head once or twice with his teeth, but after I told him he was all good. It was hot to look down and see my straight roommate bobbing on my dick, yet my eyes did move down to his bare ass while he was moving underneath me. I came very quickly, and warned him before, so he got off my dick and finished me off with his hands. I mostly came on myself, but my first shot did land near him on the bed. I couldn't help but think how hot it would look with my cum covering his face.
"So, done this once before, huh?" I asked as we both laid in his bed after our orgasms had faded. He kind of shrugged and said, "Well yeah, I told you I have older brothers. One of them showed me how to jerk off, but then made me suck him off as payback." I just kind of stared, a little stunned but more impressed because it honestly sounded hot to me. "How old were you?" "Like 15. I was a late comer" he said, chuckling at his own pun. I didn't want to say anything judgmental about it, so I just said "Well, I'm happy you learned how to do both." He smiled and curled up next to me again.
I spent the rest of that day out with my friends, very confused about what happened or what would happen going forward. Warren mostly stayed in the library studying for the next two days, but on Friday after classes we got some time to catch up. We were both relieved at the week being over, and had plans to go to a girl-friend's birthday party off-campus and get drunk. We bought sandwiches and had our older friend buy us a handle of gin to start pre-gaming with ginger ales from the vending machine. Halfway through our first GinGer ale, I asked him straightforwardly "So do you ever want to fool around again? or was that just a one time thing?" Warren blushed a bit, looked at his shoes, but looked back up at me and said "Honestly I'd love to have you suck my dick again, that was great. Not sure if I'd want to suck you again if that's alright." I told him it would be fine, but also suggested he fuck me. "For real? You'd want me to fuck your ass?" and I told him I like fucking and being fucked, but I'd gladly just bottom for a straight guy. He kind of looked down sheepishly and said "To be honest, I'm not sure if I'm 100% straight. I mean I like women a lot, but there are some guys who really turn me on. But you're really just a friend to me, I hope that's ok." I was kind of crushed to hear it: I had always told myself that Warren and I weren't right because he was straight, so it was disappointing to hear that he just wasn't that into me. However, I put on a brave face and said, "Of course. I'm not interested in you like that either, but I'd really love to ride your cock."
We never ended up going to that friend's birthday party; we blamed it on the gin and said we had too much to drink. The reality was that I ran over to a friends room, borrowed their lube, Warren got a couple of condoms out and he fucked me 4 times between Friday night and Sunday morning. The first time was the hardest; we tried doing it missionary but to be honest it weird to have him heaving on top of me and knowing I couldn't kiss him. The second time the next morning was much better in my opinion; I woke him up by sucking on his cock then rode him while holding his hands to the bed. Saturday we did go out for dinner with some friends, just to show our faces, but Warren tapped my foot under the table and I knew it was time to get back to the room. That night he pounded me from behind until I was begging for more (thankfully our neighbors assumed I had a different guy over). And finally on Sunday morning I convinced him to eat my ass before going to town on my hole again. I didn't come from anal, but he agreed to suck me off again. This time he swallowed and I really was struggling to keep it physical and not romantic with him.
The rest of the semester was a complete change for both of us. I realized it wasn't good for me to keep fucking Warren since I definitely had feelings for him. I made a real effort for a relationship with Seabiscuit (bad idea in the long run) and Warren found a girlfriend; unfortunately she was dating one of our other friends at the time they met, which caused a lot of petty drama amongst our friends. The two of them had a hot and cold relationship, but I think she kept him grounded during the last part of the semester.
Warren first transferred to another college after that semester, then took some time off. I was very sad to see him go but realized there was a lot of other stuff going on in his life outside of school; eventually he was able to graduate, albeit a few years after the rest of us. I heard his mother got remarried and his father passed away, but only through a mutual friend. After that semester living together, Warren was never good about texting or calling, so even though I saw him a handful of times before I graduated, it was never planned and he never responded when I reached out to him.
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Thanks for reading! Please feel free to reach out to me if you liked this, or have any questions, comments, or concerns.
Rox815 (at) protonmail (dot) com