Have You Ever: Slept With Your Roommate?

You’ve seen him in his underwear. He’s seen you in yours. Why not take it to the next level and do one another up the butt? Today we’re talking about the sexual tension that can arise when two gay (or not so gay) men are forced to share living quarters, along with the resulting awkwardness, romance or harmless fun that might follow if they decide to fuck.

It could start off as an innocent night of drinking, or it might be a lingering crush that finally explodes when you’re in such close proximity to one another. Perhaps, like Duncan Black and Donny Wright, you got caught in the moment during a moment of compassion and understanding? Whatever the case, if you’ve ever fooled around with a roommate, we want to hear about! Be sure to include all the juicy details.

– Dewitt

Photo credit: Str8 to Gay

Watch Duncan Black and Donny Wright in action, then discuss this topic below:

Duncan Black seduces his roommate Donny Wright to fuck him in a scene for gay porn site Str8 to Gay.

Duncan Black seduces his roommate Donny Wright to fuck him in a scene for gay porn site Str8 to Gay.

Duncan Black seduces his roommate Donny Wright to fuck him in a scene for gay porn site Str8 to Gay.

Duncan Black seduces his roommate Donny Wright to fuck him in a scene for gay porn site Str8 to Gay.

Duncan Black seduces his roommate Donny Wright to fuck him in a scene for gay porn site Str8 to Gay.

Duncan Black seduces his roommate Donny Wright to fuck him in a scene for gay porn site Str8 to Gay.

Duncan Black seduces his roommate Donny Wright to fuck him in a scene for gay porn site Str8 to Gay.

Duncan Black seduces his roommate Donny Wright to fuck him in a scene for gay porn site Str8 to Gay.

Duncan Black seduces his roommate Donny Wright to fuck him in a scene for gay porn site Str8 to Gay.

Duncan Black seduces his roommate Donny Wright to fuck him in a scene for gay porn site Str8 to Gay.

Duncan Black seduces his roommate Donny Wright to fuck him in a scene for gay porn site Str8 to Gay.

Duncan Black seduces his roommate Donny Wright to fuck him in a scene for gay porn site Str8 to Gay.

Duncan Black seduces his roommate Donny Wright to fuck him in a scene for gay porn site Str8 to Gay.

Skip the discussion and watch more of this scene at STR8 TO GAY.

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416 thoughts on “Have You Ever: Slept With Your Roommate?

  1. I FUCKING LOVE Donny Wright especially when his marvelous ass is getting FUCKED !!! Oh and to answer your question Dewitt no he was a tenant LOL !!!

  2. I guess it would help if I’d had roommates that looked like Duncan Black or Donny Wright….

  3. I hooked up with my roommate back in college a few times. The first time was the hottest when no one knew I liked guys. Him and I were walking back from a party a little buzzed. Some flirty touches led to copping a feel and then before I knew it, we hopped a fence to a construction site where we stripped and messed around.

  4. Freshmen year in college, my roommate came back from some league sport all sore and tired. I offered him a massage after his shower. He had his underwear on, I had mine. I started on his back and shoulders and everything was on the up and up, I moved down to the lower back and then the glutes and legs. He rolled over, I noticed a bulge in his shorts. I started on his chest, deliberately lingering around his nipples and I watched his shorts tent even more. I moved down to his stomach and then his legs, I got the nerve to ask if his shorts was constricting and he can take it off if he wanted. He was shy, but he did take them off. I brushed my hands against his nut sack and he moaned, I don’t know what came over me, but the next thing I know, I had his cock in my mouth and before long, I was swallowing his hot load. For the rest of the year, he would ask for a massage every now and then when he came back from playing sports and I happily obliged.

  5. Just out of college I shared a flat with a friend. He was still in school. At one point we had both been dumped by our girlfriends and took solace in each other’s beds. We’d wake in the night our bodies pressed together, our boners hard against the other’s belly. A few nights later I woke to him pumping his hips slowly, rubbing his cock against my belly. I realized it was his precum wet in my navel. He didn’t stop me when I began caressing him. He fucked my hand, his hot load spraying all over my belly. “I’m not gay,” he said, holding me in his arms. “I know you’re not,” I replied. Frotting and body humping happened the next few nights. Next night I took enemas and showered before he got home, condoms and lube by my bed. When he crawled in we didn’t even pretend to fall asleep first. As he got on top and moved against me, I wrapped legs around him. “I want to fuck you,” he said. I rolled a condom on him, lubed it and my hole and he pushed into me in right away. He pumped like five times and came, then rolled away. “I’m not gay,” he said as I held him. “I know.” Fifteen minutes later he had a second condom on and pounded between my legs again, my hands feeling his muscled body flex as it moved. He yelled when he came. I was on all 4s for his third. We started fucking regularly. Morning blow jobs in the shower. Then he got a new girlfriend and it was like it never happened. One night he came home late and slipped into my bed again. He had fucked her and wanted to fuck me. “I’m not gay,” he said, looking down at me, his hips thrusting. “I know,” I said. “I’m bi,” he said. “I know.”

  6. I hooked up with a buddy who then became my roommate down the line. By that point, he had found himself a partner, so we don’t hook up anymore.

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