[MM] Cheating on my gf with my roommate

Originally posted about my experience in r/gaystoriesgonewild, someone suggested I should post here.

I was a freshman in college. I always thought I was straight. I was into girls, I fantasized about girls, I dated girls. Specifically, at the time, I was dating someone I knew from high school, call her Kate obviously a fake name). She was in the same friend group since freshman year, and we started dating junior year. We were both studios and were accepted to the same state university–not that surprising since state uni accepts ~40% instate students.

Anyways, first day of college, we drove with each of our families to uni, we unpacked, each had dinner with our family, and met up and explored the campus. Because we had come so early, I had not met my roommate yet. When I came back, it was night, and he had already unpacked his stuffs.

I was surprised when I first met him, let’s call him John. We couldn’t have been any more different. I was moderately tall (5’8) with blondish hair, and slender frame with a boyish look. He was maybe 6’3, with ragged brown hair and beard, with a muscular frame. I felt small in front of him. When we shook hands, I noticed how bigger, and rougher his hands were to my smooth hands.

I got to know John very well over the first semester. He was athletic, though he wasn’t in any sports team, and overall a really nice, if not a little quiet, guy. He wanted to study literature, and was really smart. Over time, I began to develop an inferiority complex towards him. I felt like less of a man, when I was with him, smaller, almost feminine. In fact, I began to be paranoid, analyzing my every action, so that I don’t seem submissive, or feminine, which was hard to do, since he kept paying me strange compliments like “your laugh is so cute” or “your eyes are really green”, which made me even more insecure as a male, since those kind of compliments are what guys say to girls.

It didn’t help that Kate liked John a lot. Even to the point of inviting him out to movies with us, or sometimes talking to him 1 on 1 when I’m not there. It made me feel even more paranoid. I began peeking at him, when he’d come back from shower, or the gym, comparing his muscles with my slender arm.

Sometime between spring break and start of second semester, this inferiority complex took on a sexual nature. One time, when Kate laughed, it reminded me of the compliment John had paid me, and it made me hard instantly. When she moaned, I imagined it was John who was fucking her, not me. That eventually transformed to me fucking John, as Kate. I began to imagine what it was like to have sex as a girl, to be dominated, fucked like one.

Spring semester, rush began. John and I went to events together with a few other friends. One event we got completely drunk, and we were walking back alone. As a joke, he pinched my ass, saying with an ironic machismo voice, “You got a cute ass, baby.” In any other circumstance, I would’ve been like, “dude, fuck off” laughing. In my drunkenness, I was scared how aroused I became. I don’t think I’d ever been so aroused before in my life. I said, almost shyly, girlier than I’d thought i’d sound, “yeah?”

He continued joking, with the same voice, “ooohh yeah, baby, that’s some nice ass.” he groped my ass, stronger this time, and shook it violently. I moaned quietly.

By this time, I think he knew what was happening, and he suddenly fell quiet. When we got to the elevator, he started tentatively caressing my ass. I drew myself close to him, smelling his musk, my dick harder than ever before, as i realize in my drunken stupor that I was submitting sexually to another man. The caress slowly turned into a kneading, making me squirm, as I moaned quietly, not involuntarily, but because I wanted to make him, the male, more horny.

By the time we got to the room, we were half-sober. We started undressing and making out. “Are we really doing this?” he said, looking down at me. I said, timidly, “yeah.”

By this time, he must’ve known I was his bitch. He ordered me to take off his pants, and suck him. My heart was pounding, my dick about to burst, as I knelt in front of another man for the first time, taking off his pants, his boxers, and saw his cock. His was much bigger, 7″, and girthier. I took it in the mouth, feeling it expand and shrink. I imagined I was Kate, pleasure the man I wanted to mate with. I thought I was gonna cum, when he started stroking my hair, telling me, “good boy.”

After a while, he pulled me up gently, whispering, “i’m gonna fuck you.” My heart leapt, and I said meekly, “yes daddy.” That must’ve been too much for him, because I felt his dick spring up. We quickly lubed up and put on a condom.

In doggy position, I felt his dick enter me, I imagined I was Kate, mating with him. “Oh, daddy” I moaned. He liked being called daddy, and he started fucking me. I thought what Kate would think, what my mom would think, her gf, her son, who’s supposed to be the one fucking , being fucked, being used by another man. This thought made me cum, but I was so horny, I was still erect. After first ten minutes, he slowed down, and we switched to missionary position. We started making out while doing it. It became a disturbingly gentle sex, disturbing because it almost felt like the kind of sex I had with my gf. At that moment, I felt I could do anything for him. He “owned” me.

When the sex ended, we slept cuddling. I woke up in the middle of the night, remembered what just happened, and felt a wave of shame wash over me. I took a shower, and went to sleep in my own bed.

That was just the first sex. It became a routine thing with my roommate. I’ll share more ‘incidents’ if people are interested.

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I wrote a second post, which I’ll link shortly.

Source: reddit.com/r/gonewildstories/comments/6hkrex/mm_cheating_on_my_gf_with_my_roommate