Back in my 20s I (28 at the time) had a straight roommate, we'll call him Jason.

Years back, when Jason (21) became my roommate, he swore he was fine living with a guy who, as our mutual friend Colin so delicately put it, “always has men lined up to fuck his ass.” Colin said this with the kind of smirk that invited trouble, which is probably why I mockingly slapped him across the face before saying, “Twice a day, minimum. You got a problem with that?”

Jason laughed, brushing off Colin’s teasing. “I’m fine with it. Seriously. The place is big enough, and we’re both adults. I’m not going to freak out just because my roommate has a sex life.”

“Good,” I said. “Because this sex life is loud, proud, and happening regardless.”

That pretty much set the tone for our arrangement. I liked Jason because he wasn’t weird about me being gay, and he liked me because I wasn’t weird about him being straight. We’d known each other for a couple of years already—enough time to get drunk together, laugh over bad hookups, and swap just enough sexual war stories to make things interesting. So when my old roommate moved to Japan with his girlfriend, Jason hinted heavily that we’d make great roommates. He was right.

The first time I brought home a guy from a bar, Jason was already home, watching a movie on his laptop (before streaming, and if you downloaded a movie you had to watch it on a computer). We'd already talked about this kind of scenario, and the guy I was bringing home (Jeff) was warned I had a roommate.

"Jason, this is Jeff." Jason looked up at the guy, intrigued, not showing any signs of annoyance. "Hey" Jason said. Jeff was closer to Jason's age (about 22) and while not shy at the bar, showed no interest in a conversation at 2 in the morning with some roommate (weird!).

Jeff and I got to my room. "I can still fuck you? It won't be too noisy? You can just suck me off if you'd prefer to keep it quiet," he said. "Although I've been grabbing that ass all night and I'd really prefer to fuck."

"All good" I assured him. "I need it pretty bad. The place is pretty big and we have privacy. My roomie just moved in, but we've talked about needing to live our lives and not worry too much about bothering the other guy in situations like this, within reason."

"Nice," Jeff said. "We good to get right to it then?"

"Oh yeah," I said. "Just like we discussed, you fuck me as long as you want, you cum, and you can go. Condoms and lube are in the top dresser drawer."

"Great! Get naked on the bed on all fours and wait."

I did exactly that. I could see Jeff was hard and ready to fuck. I was a little nervous about Jason being in the apartment. We'd exchanged lots of sex stories in our late-night drinking sessions and were pretty comfortable with it, but I wasn't quite sure if he meant it when he said "You can get your ass fucked as much as you want; it won't bother me."

Jeff unzipped as I was getting on the bed, prepared himself, and groped my ass and touched my hole. He applied some lube and pressed his 7" cock against my hole. I moaned a little--not too loud out of respect for my straight roommate in the other room, but I also wanted to enjoy myself. There wasn't much foreplay--within about a couple minutes, Jeff was balls deep in my hole, going slowly, letting me get used to his girth, but also with a bit of impatience. "I really want to start fucking this tight ass; let me know when you're good."

I was ready. My hole was adequately stretched and I needed to get fucked. Jeff started long strokes with his long cock as he grabbed my hips. He was standing on the floor next to the bed, still mostly clothed and still even in his shoes. He wanted to unzip, fuck, cum, zip up, and go. He was a great fuck. He did short bursts and long fucks. There was a lot of clapping of ass cheeks--I'm sure it was pretty clear to Jason that there was full anal sex happening, if he could hear at all. Could he hear? Did I care? Between Jeff's strokes I thought a little bit about it. But mostly I was concentrating on the pleasure, stroking my big 8" cock (yes, a big waste on a bottom like me) as I got fucked from behind.

"I love fucking this ass. I love how you can take my big dick balls deep. I love how you have a bigger dick than me but I'm still the top." He pounded my hole, and his breathing quickened. "I'm gonna cum right up your ass. This feels so good." I was rock hard but not quite ready to cum, but that was fine. We talked about it being a quickie.

About 10 minutes after sticking his dick in my ass, he was shooting cum into the condom in my ass. He let it rest for a bit, then pulled out, and pulled off the condom. "Where should I put this?" he asked.

"You can empty it onto my back and then go if you want," I smirked.

"Fucking hot" he said. He did exactly that, making a big mess in the small of my back. "You were exactly what i needed tonight." He zipped up, slapped my ass, and said, "See ya." He walked out. I heard him exchange a few words with Jason. I heard a laugh (?) and then heard the apartment door open and shut. I guess Jason was cool with the whole thing?