By the time I went to college, I had a lot of experience, but only with a few men. Once I was living in the dorms and surrounded by all those horny guys, that quickly changed. It wasn't difficult to find classmates that at least wanted their dicks sucked. Within a couple months, my dorm room was being visited regularly by several horny students knowing I would happily swallow a their loads. While I loved my frequent guests, my roommate had not been a fan of listening to what was happening behind the privacy curtain. He didn't mention it often, but would toss out some passive-aggressive statements occasionally. He usually just put on headphones since our room was small with beds on either side and just the curtain down the middle. My visitors knew to knock, I'd answer, and they'd go to my bed and pull out their cocks.
For the first few months, he only had to listen to some whispers, maybe some slurping, and my guest moaning since I would limit myself to oral while he was there. There was a lot of fucking happening as well, but only when he wasn't in the room. I had a standing meeting three times a week with one guy while my roommate had class. My roommate would sometimes go home for the weekend and I'd have the place to myself. I would also meet older men online and go to their places. This routine went on for months without much resistance from my roommate until one of my regulars decided in the moment that he wanted more. He was a very athletic guy with a nice cock who I would suck a few times a week. On a couple occasions when I had the room to myself, he brought over vodka and we'd drink a bit before we started fooling around. I was the first guy he'd been with and a little liquor made him hornier than usual, so he wanted to fuck. I have always been more than happy to help a man explore his sexuality. Once he got a taste though, he wanted more.
One fateful day not long after our second weekend fling, he showed up to the room for a blowjob after he'd been drinking. It wasn't unusual for him and I had no problem giving him what he wanted. My roommate put his headphones on and I got to it. I sucked my guest for about five minutes before things took a twist. He stopped me and told me he wanted to fuck. In a whispered conversation, I told him I couldn't with my roommate around, but it didn't take much for him to convince me to make an exception. We quickly stripped, I put a condom on him, and I found myself on my stomach with this stud on top of me. It didn't last long. He was inexperienced and was just happy to have a tight hole to fuck. What I wasn't expecting was how loud he would get when he orgasmed. It was a series of "yes" and "fuck yes" followed by several "I'm cumming!" declarations before he shot his load. He got dressed and was out the door after getting what he wanted. Little did I know that my roommate was listening to the whole thing.
I put some shorts on and pulled back the curtain so I could apologize to my roommate about the noise. I was expecting some snide comment, but instead he joked that my guest really enjoyed himself. As a natural flirt, I could only respond by saying that they always do. We turned the TV on and hung out for a while before the second twist of the day happened. The show had a sex scene and I noticed my roommate touching himself through his shorts. I couldn't keep my mouth shut and joked that his girlfriend must not be taking care of him. We didn't talk about personal things much, so he informed me that she broke up with him a little while ago. He had been quieter than usual, but I thought he was upset by my frequent visitors. He was obviously horny, so I offered to give him some privacy while he took care of it. His response caught me completely off guard. He wanted me to suck him. Apparently he'd been curiously listening to the many guys moaning and rationalized that it must feel pretty good if they keep coming back.
I told him to pull out his cock as I got on my knees next to his bed. He laid back as I got started. He was moaning almost immediately. Before long, he was telling me how much better it felt than his ex. He told me that he had been getting hard listening to my guests moan and that hearing the guy fuck me today had been hot. Within minutes, he was pulling my head down on his cock and firing his load down my throat. I gladly swallowed and licked his cock clean. We went back to watching TV with smiles on our faces. Our relationship had just taken an exciting turn, but the fun had only just begun.
Maybe an hour later, there was a knock at our door. Another horny stud needed some relief. I let him in, closed the curtain, and got right to it. Knowing that my roommate was probably listening, I took my time and really tried to make my guest moan. He fed me his cum about fifteen minutes later and was on his way. I opened the curtain to find my roommate waiting for me with his hard cock in his hand. I took the few steps across the room and hit my knees to suck him again. This time he didn't lay back and instead watched me work him like a pro. He told me that he was hoping to hear me get fucked again. That really got me turned on and I told him that he could fuck me if he wanted. I was expecting him to say no, but after a few seconds, he hadn't responded, but I tasted a dose of his precum. I looked up at him while gripping his shaft and knew he wanted it. I stood up, walked back towards my bed, opened the night stand drawer to display an assortment of condoms, dropped my shorts, and climbed on the bed with my butt in the air. Seconds later, he was behind me tearing open a condom.
He wasn't shy about what he wanted and told me that he had fucked his ex in the ass a lot. With one hand on my lower back and the other holding his hard shaft, he lined up and pushed his cock into me for the first time. As he slowly began thrusting, he told me that he had been jerking off thinking about me and some of my frequent guests. Hearing the guy fuck me earlier really got his imagination going. He sped up as he told me how great it felt and that he could see why my visitor had cum so hard. I responded with some words of encouragement and told him that his cock felt amazing inside me. As he went deeper, he said that his ex would complain during anal and he'd have to stop. I assured him that I wanted him to keep going. He wad the confidence of a man that had fucked a lot of ass which was a welcome surprise from the inexperienced guys I typically found on campus. As he grew closer to climax, he asked what position I was in with the earlier guy and then told me to get on my stomach.
He mounted me and drove his cock deep with a strong downward thrust. I could feel him grinding against my prostate almost immediately. I figured he didn't quite know the mechanics of sex with a guy, so I let out a moan and some words of encouragement for him to keep doing it. My earlier fuck wasn't consistent enough with his rhythm to push me over the edge, but my roommate was about to experience the involuntary tightening and shaking of my prostate orgasm. This time I was the one starting to get loud. I begged him to keep going and let him know I was about to cum. He kept pounding me into the mattress with each thrust as I gasped and yelped. I was cumming hard.
I could feel my hole tighten and my body start to shake as my eyes rolled back and jaw dropped. He kept pounding away and let out some sounds of pleasure as well. Another dozen or so thrusts later he let out a long "fuuuuuuck" and I felt his cock pulsate against my hole. It was a magical moment as we orgasmed together. As he stopped thrusting, I could feel his cock twitching while resting deep inside me. He had me pinned to the bed as we both caught or breath. He hadn't even pulled out of me after our first time fucking and he told me that he was looking forward to doing it again. Being a good bottom boy, I let him know that he could fuck me any time. He made me promise not to tell anyone about or fun times, but he knew I wasn't one to fuck and tell. As he dismounted, I caught a glimpse of the condom dangling several ounces of cum from his half-erect cock. Another satisfied customer.
I rolled onto my side to reveal my own sticky mess. It was just another added to the smaller cum stains over the prior few days. We chatted as we cleaned ourselves up. He didn't have any hang-ups about having fucked a guy for the first time. He started asking me questions about my experiences, how long I'd been playing with men, and how many I'd been with. We were flirting heavily for a while after that. He said he was going to hang out naked from now on. As we called it a night, we both went to bed happy.
Dorm life got a whole lot better after that. My roommate would listen to me with other guys and it turned me on knowing he was there. I started letting some of my visitors fuck me if they wanted to. When they left, I would see if my roommate wanted to play. Sometimes he would jerk off while I was getting fucked. I helped him explore what it was like for me as well by finding a friend who I trusted to come play with my roommate a few times. I gave him blowjob lessons and talked him through relaxing while getting fucked. We would shower together sometimes and he'd wake me up to play if he was horny. Everything that happened between us was our sexy secret. I still made sure my regulars were taken care of. We were roommates for another six months or so, but continued to hook up regularly for the following two years until he graduated and moved away.