Roommates Stories: Steven
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.
-
Steven (Freshman Year of College)
Steven wasn't my first roommate when I went to my liberal-arts college in upstate New York, but he was one of the first friends I made around the dorm. On the first night a group of us stayed up for hours talking in one of the lounges, and as it turns out 7 of the 8 of us ended up coming out as gay, lesbian, or bi.
My actual first roommate was a moody recluse with muttonchops. I tried to include him in things I got up to, especially the first month, but he never wanted to leave the room and rarely had much to contribute to conversations. With little time alone to myself in the room, and weeks without masturbating, it forced me to be a social butterfly with all the other friends I made in our dorm. My moody roommate dropped out at the end of the first semester, and knowing that Steven had a bad roommate situation, I suggested he move in with me.
At the start of the second semester, we were pretty close to best friends and most of our friends we had in common. Steven was very far from shy: he was loud, proud, and usually tried to make his sexuality the focus of everyone's conversation. Thankfully we had a lot of lesbian friends to cancel him out. We were both pretty modest in the room, changing under a towel and staying fully clothed until underwear to bed. He mostly wore baggy boxers, unless he was expecting to get laid and then he'd wear his tight pink briefs. He had a long-distance relationship going with his older boyfriend in New Jersey, so there were plenty of nights I was "sexiled" to the dorm lounge so he could have cyber-sex. My joke was that he wasn't the only one who needed to jerk off in front of a computer every once in a while. Overall we got along well despite having very different personalities.
During spring break, I was on a school-sponsored trip abroad that left me jet-lagged and overdue on all my homework when I came back to school. Steven had spent his break on a trip down to New Jersey to find out his boyfriend was in love with another man. I think they didn't officially break up for a few days after; Steven went from happily boasting about all the three-ways he had, to devastated and morose.
Steven had a real taste for booze, and even though I drank the second-most after him among our friends, I could always hold it a bit better. One weekend after his breakup, we both came back to the room from separate parties. He was sloshed and dancing around the room eating Doritos, while I was tipsy not messy. We talked for a long time about his breakup, the latest cute boy he saw, a cute boy who I was crushing on from English class, but ultimately the booze caught up with him and he ended up crying in his bed over the breakup.
We had always been physically affectionate with each other, but usually with one or two of our girl-friends in the hug as well. This time I got up in his bed, and held him while he cried. It was a tender moment and even though I wasn't sober I think I gave him some encouraging words. At one word in particular, he interrupted me to give me a small (but wet) kiss on the lips. I hadn't kissed anyone since high school, so this really got my blood stirring. He was smiling and said I was always kind to him and he didn't deserve it. While reassuring him, he went in for another kiss and this time I kissed him back.
Both of us drunk, it was maybe two or three minutes of kissing later before we felt each other's pants bulging. He started giving little moans into my mouth when I pressed my bulge into his, and even though he had these baggy jeans I could feel his hardness pressed up against mine. I broke the kiss to let him know maybe we should stop before we did anything more. He nodded, but also kept thrusting his hips into mine. He moved his arms from behind my back towards my ass and I couldn't resist anymore so I grabbed his hard-on through his jeans.
After a few tugs and his appreciative moans he asked me to take his pants off, and I was more than happy to help. He left his boxers on, but they were thin and tenting. I could see my prize in sight and wanted to even the playing field. I took my shirt and pants off, down to my black briefs. He was able to take his own shirt off, then laid back down on the bed with his boxers tenting. In that moment I finally let myself realize I was attracted to Steven. He was tall and slim, with a little bit of definition to his arms and shoulders, but he had a small soft tummy with a light coating of blonde hair from his chest to his happy trail. His erection went straight up to his belly and looked so inviting I knew I wanted to suck it.
I laid on top of him and we kept kissing, his arms moving to my waistband and mine moving towards his stiff erection. I moved my kissing further down his neck and his moans got louder; he begged me to play with his nipples and I was happy to keep teasing him there. I had never played with a boys nipples, my own aren't sensitive, but for Steven it sent a bolt of lightning straight to his crotch. His thrusting got wild and I looked down to see a small wet spot at the tip of his tented boxers. I didn't want to play around anymore and I moved my head down closer. I unbuttoned his fly but he just lifted his hips and took off his boxers altogether. It was the first uncircumcised cock I ever saw: long but thin, trimmed blonde pubes, and a small drip of precum at the tip with his foreskin still almost entirely covering the red head. I stroked it gently a few times to see how far I could get his foreskin back, then gave a slow lick from the underside up to the tip. Steven was whimpering at this point and said "I need you to release me." I gave a small nod and took his cockhead in my mouth. His precum was so sweet I kept licking at it, before starting to bob my head up and down. I was far from an expert cocksucker (two guys in high school: one once, the other about a dozen times) but with a little bit of suction and two tongue circles around his dick, Steven started grabbing my head. I knew he was close, but he wouldn't let me get off him so I deep-throated him right to the base. In seconds he was shooting long ropes of cum down my throat with my nose pressed up tight against his sweaty crotch. When I finally pulled off, I licked my lips to show I enjoyed it; he gave me a long look and then insisted I cum too.
I flipped on my side and started to pull my briefs off, but his hands took over. He kept kissing me through undressing me until I was naked on his bed with my hard-on pointed straight up. He straddled me with his butt just in front of my dick and I was certain he wanted to ride me. Steven seemed to read my mind and said, "Not tonight, but someday I want to ride that thick cock." He gave a few strokes behind his back before he turned around on top of me and leant down to start licking my hard-on. His hairy ass was right in my face and I wanted to eat his hole but didn't want to push my luck that night. Instead I moaned and played with his balls and softie for a bit while he went to work on me. Maybe it was the booze but Steven gave a very wet and messy blowjob that I couldn't see much of; at least I didn't have to tell him about teeth. I lasted a few minutes but his mouth was like a vacuum cleaner and as soon as I whimpered "I'm close" he went into overdrive and swallowed a huge load from me. He adjusted himself so we were face to face again, we kissed briefly, and before I knew it we were both asleep in each others arms.
I woke up early the next morning with a killer headache, but his hangover was far worse. I took a shower and immediately thought Steven might regret what we did since we were just friends and he was so drunk. When I came back to the room he was still groggy but on his laptop and I asked him how he felt. He glared at me, said his headache was killing him, but then changed to a smile and said it was still the best blowjob he'd had in months. That cut the tension plenty, and I spent the rest of Sunday with some friends mostly happy about what happened, but not telling them anything since they all knew Steven. That night Steven and I talked things out a bit further and he said even though he wasn't in love with me, he liked messing around. I took that as an all clear, and we hooked up again, making out in his bed and sucking each other off.
The rest of the week was busy for us, and it was more comfortable sleeping in our own beds since the dorms had narrow frames, so we didn't do anything again until the weekend. On Friday and Saturday, we each went to separate parties, but each night he called me drunk from his party and asked me to come there. On Friday, I knew the people throwing the party so we hung out for a while until it got time to leave. On the way back to the dorm, Steven begged me to kiss him. I didn't want the extra attention and I told him we could do it in the dorm. That night he blew me, and when I started sucking him he asked me to start fingering him. He had such a tight warm hole it was very hard not to do anything else, but my fingers helped give him an extra large orgasm when he came in my mouth.
On Saturday, he asked me to come to a party in the on-campus apartments on the north end of campus. I didn't know anyone there and didn't want to stay long, even though there were a lot of hot hockey bros there. Steven dragged me to the upstairs bathroom at one point, and started making out with me. I told him I didn't want to kiss near a toilet, and he sighed "fine" before slipping his hands into my pants. I was wearing looser boxer-briefs so he got his hand on my cock quickly and started rubbing me. He whispered "I want to ride your cock tonight" in my ear as I tried not to groan too loud. I eventually pushed him off me and made him leave first so my boner could deflate a bit before rejoining the party. As soon as I got downstairs, Steven finished his drink and said "Ok we're leaving now thanks!" to the rest of the party, grabbed my hand, and headed towards the door.
It was at least a 15-minute walk down the hill to our dorm, but Steven was staggering and trying not to throw up. We stopped by some bushes near a baseball field, and he got on his hands and knees. Instead of puking, he took his pants off. "Do me here. I can't wait." I had neither a condom nor lube, and didn't want to get in trouble with campus police (Headline: Drunk freshmen found fucking on the side of a well-lit field). I just pulled him back up and said we can do it in the room. When I finally got him back to the dorm, he collapsed in his bed fully clothed and I knew it wouldn't be a good idea to do anything. I filled his water bottle and climbed into my own bed, but boldly I jerked off right on top of the covers. I thought Steven was asleep, until right after I came on my chest and he whispered "That was hot". I laughed and fell asleep.
The next morning Steven was awake before me and we got breakfast separately. When I came back to the dorm to study, he was completely naked on his bed, faced down, looking at his laptop. He turned his head to me in the doorway, smirked, and said "I didn't forget about last night. You're going to fuck me now." I don't think I had ever seen his ass in bright daylight before; it was covered in a soft blonde peach fuzz, and perfectly toned but still nice and plump. I hurried to strip off my clothes while Steven grabbed a big bottle of lube from his desk drawer, and then we started making out in his bed. I don't think we kissed for long at all before he lubed up my fingers and then his ass, and directed me to start fingering him. I told him how I wanted him on the bed: face down, ass up. He obliged and after fingering him for a while (one then two then three) I put on a condom and gave my hard cock a good amount of lube and slowly started pressing at his hole. Even thought it wasn't as tight I still inched my way in slowly. He was moaning and groaning with his head in his pillow. I asked if it was alright, but before I got an answer he backed his ass up until my whole dick was inside him. We held it there for a few agonizing moments before he started moving back and forth. Steven was a true power bottom, and even though I liked setting the speed and keeping my hands on his hips, before I finished he had me on my back and was riding me into submission. I came with little warning and after my second shot in his warm hole, it gripped me like a vice and he started to cum. I reached around to help finish him off and soon enough we had a couple of sticky messes. I licked his cum off my hand and he went to the bathroom to clean his ass up.
Unfortunately, we didn't have much sex after that day. The following weekend we fucked once more, and one time he blew me and even fingered me a bit. I always wanted Steven to be the first guy to fuck me, since he was the first guy I topped, but it never happened. He got a boyfriend in a week or two, and after Steven drunkenly asked me and him to do a three-way, it got awkward (I was down for it, but his boyfriend was not interested.) The two of them slept over once, but his boyfriend snored so loudly I made him promise that they would spend nights in his dorm from then on.
Semester came to an end, and we went back home planning to be roommates the next semester. We didn't stay in touch as much as I wanted. Steven seemed to bounce from his ex to a new boyfriend to a week in Provincetown to Fire Island, and I had to work a summer job in my hometown (thankfully I found a fuck-buddy). When we came back to campus, we started to hang out in different circles. He got a vaporizer and was almost always high, while I changed majors and had a ton of coursework. I heard from a mutual girl-friend at one point that semester Steven was bragging that his personal count of men he'd slept with went from 4 (not sure if he was including me) to 22. He brought some of them back to the room, but they never stayed over. I generally gave him privacy and would study in the library or lounges. About the only benefit that semester was that we would hang around the room naked together. He also started wearing more jock straps so I got to see his cute butt a lot more often. Unfortunately, we also had a first floor room with a window facing the quad, so it was either dark and naked or sunlit and clothed.
At the end of the semester, my best friend Warren had an opening in his room while his roommate was studying abroad, so I jumped at the chance to bunk with him instead. Steven and I left on fairly good terms even if we weren't much for buddies. I bought pot from him once before we graduated, and since then all I know is that he's living in the same college town, selling pot, and in a polyamorous relationship with two bears.
--
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