This is a post about roommate sex, but not about roommate sex I had with my roommate. In fact, I never have had sex with any roommates I’ve had. Yet.
I have, however, had sex with two pairs of different roommates before. Which, in case this title made you too horny to do basic math, amounts to four men, total. All of them separately, but I was sleeping with both of them while they were roommates.
Actually the first set of roommate sex was in my late teens…
It was my boyfriend at the time, the one I loved for the last year of high school and the first year of college. He was the one to whom I lost my virginity. I was into his mind, and the way he stimulated mine. I don’t think either of us were very physically attracted to one another. Our relationship was during the worst phase of physical awkwardness for both of of us, so, we probably learned some unfortunate lessons through bouncing that weird shame back and forth.
After I find out that he cheated on me, through his eventual confession, we work it out by giving me some sort of retribution: I can fool around and he can’t. So for a while I start fucking his friends, without actually really being conscious of it as a bad thing to do. He doesn’t seem to care. It annoys me that it doesn’t bother him. I try harder.
Leave it to me to take that too far and start fucking his roommate…
These young men are both at Caltech. They are both overworked. Both nerdy af. The roommate is definitely underfucked. He had a high school love that he is still somewhat obsessed with. Looking over photos and whimpering her name as a way to connect with me. Coke bottle glasses. A dorky laugh.
And a deep sex drive that my boyfriend does not at all have. The roommate is more communicative, more emotive, and more eager about sex than anyone I have slept with, and that’s what attracts me beyond the first time where my motivations aren’t great. I’m just titillated about fucking my boyfriend’s roommate and also mad at my boyfriend so ready for some revenge porn. That does eventually morph into real desire, just in that he’s more sexually open than anyone I’ve yet been with.
Of course as he fucks me more and more, his obsession with high school gf wanes into heartbreak over me being promised to another. My uneasiness at his obsession with another doesn’t ease with it being about me. He’s at first totally cool with fucking me, especially when boyfriend is not around, but then, less cool. I slowly break his heart.
Part of this might be due to the quintessential roommate sex moment that sticks in my mind to this day.
The boys had a bunk bed. They slept in the same room.
Boyfriend on top and roommate on the bottom. I slept over some half dozen times, in one bed or another. Whilst the other slept in the other bed.
Boyfriend really didn’t care. I think he was just never that into me and only with me because I applied pressure on him to be so, and he was too much of a coward to break it off. He certainly thought I was cool, but he didn’t have the hots for me. Also he’s just not that jealous of a person and kind of detached from the world in general. All this to say, he was tolerant. If I chose to sleep in roommate’s bed underneath him he’d just fall asleep whether or not roommate and I were fooling around.
The other way around though, not so much. Roommate wasn’t down with me sleeping with boyfriend right above him.
And so the quintessential roommate sex is that time when I and my boyfriend both thought that roommate was sleeping, and so quietly, discretely as possible, he massages my clit. Boyfriend is good at making me come. I am getting off on the naughtiness of having sex in the same room as someone else I have sex with and am wet and trying ardently not to breath heavily.
Little wet sounds of finger on clit fill the silent room. The energy of sex takes over any common sense or shame. There’s of course no way that roommate can’t hear this, but we are all teenagers at the time and so we all pretend. Each thrash of cloth on cloth as I curl my toes into the sheet masked with me changing positions just a bit until I can’t focus and I breathe heavily and hold my body still as waves of orgasm take me. My boyfriend takes this as his cue to roll on top of me.
I’m on the pill so he silently mounts me without a condom, which isn’t the smartest choice considering the situation, but everyone knows who’s fucking who anyway, it’s not like we’re not doing it in the same room as my other lover.
And we are, we are doing it, my shy boyfriend has a huge, uncut cock and he eases it into me.
Stretching me open and pinning me. It feels good to lose control and let someone else decide my openness for a moment. I float away. Boyfriend never seems very present for sex. There’s so much he doesn’t express. But as he fills me with his hard cock and the sounds of rhythmic shuffling of sheets and his breath short and hard are joined by the sounds of the whimpering roommate, now audibly crying as my boyfriend comes inside me.
Looking back on this it just makes me laugh, but I also am amazed at my downright cruelty. Women can be awful. So female.
Later after the boyfriend and I break up I have sex a few more times with the roommate. I remember sucking his cock once and him stopping me.
“You’re too good at making me come. I don’t want to come yet. Can you do something else for a while?” he asks.
“You want me to tease you?” I ask, smiling. This is the most open communication I’ve yet had about sex.
I lick his balls, snaking my tongue along the crevice between his sack and his thigh and then flatly, broadly, licking the underside. He moans and nods and I alternate between this and sucking him as he teaches me the very beginnings of edging a man with my mouth. He doesn’t know he’s teaching me and I don’t know I’m being taught. We don’t have a word for what we’re doing, but now, more than twenty-five years later, I remember it as the beginning of a new world of pleasure.
I’ll remind you that this was not the only time I had sex with a pair of roommates. The other time is also with a pair of nerds, but this time they’re more unruly, more druggie, more hackery. Eventually I graduate from nerdy men (though I still enjoy them now and then), but at this time I’m exploring the outskirts of the category.
I met The Mad Scientist through his roommate. I had messed around with the roommate months before I ever got with The Mad Scientist.
The roommate and I snuggled all night one night while I was with my previous boyfriend… never was good at monogamy.
Very good at the kind of eroticism that involves a line that I can’t cross. Love toeing that line. And once I get what I want, well, meh. In this case we snuggled a few time but as much as that included very erotic sroking, I still kept to my line. It wasn’t cheating if there were no genitals involved.
I laugh at this today, but dotted lines like these did provide a lot of titillating fun. Hot moments. Feeling the roommates’ erection but ignoring it. Bare skin tingling as every nerve ending takes in his hands traveling over my body. Measured breaths and avoided kisses. Contorted denial.
The roommate and I do not have roommate sex, not at this time.
No, it’s not until months later when I am courting The Mad Scientist, who tonight is not in the mood for me, not until then that I finally fuck the roommate. The Mad Scientist is playing hard to get and I am again using my special lady logic. I am erroneously convinced that me fucking his friends and roommate will somehow make him see how hot I am.
It does actually end up working in that The Mad Scientist and I get together, but I’ll never know whether the roommate sex helped or harmed that effort.
Conveniently the roommate’s room is directly below The Mad Scientist’s room. For a few months I haunt the stairway in between.
The Mad Scientist and I are seeing one another at the time, but have not declared any kind of relationship yet. We’re getting serious and it triggers him, which triggers me. The roommate and I know that could be our last chance to fuck before I end up in another monogamous relationship.
One summer night, we take that chance.
Of course now that I’m in my twenties alcohol is involved in this roommate sex. I’m good and drunk and certainly this encounter isn’t the best showcase of consent, but it’s not like I didn’t want it. There was no sober conversation that I recall. He takes advantage of me and I like it.
What I do remember is being drunk and woozy and feeling good. Lying on my back with a pillow under my ass. The roommate sitting on his haunches in front of me putting a condom on his small dick while he rubs it to get hard. I remember him talking dirty, but not what he said.
Then he kneels up and shoves into me. The angle he chose felt so good I melted into him and the bed. Letting him have me. Letting him use me.
He grabs my hand and puts my finger on my clit, etlling me to get myself off.
Tries different heights until he gets what he wants and then he fucks me like a bunny rabbit. Short, shallow strokes that move my finger along my clit without me having to do anything to get a rub. I am surprised by how sexual he is, before he’d seemed so sensual I thought he didn’t have a savage edge, but now here he is essentially using my pussy to jerk himself off and telling me how much I like it.
He wants me to come but doesn’t really care if I do, red-faced and leaning into his fuck. He grabs me by the thighs and jiggle-fucks me fast and hard, staring down at his dick quickly moving in and out of my slick pussy, licking his lips, holding his breath and exploding into a convulsive orgasm.
“Yesss….” he hisses.
And so, that year at Burning Man, I have sex with both The Mad Scientist and his roommate, but not together. Neither of them are into that, even at Burning Man, which kind of bums me out. No MMF threesome for me, yet.
The roommate comes to me, visiting me in the top bunk of my RV. The small space restricts our movement and cramps our style. He doesn’t come, no real room for him to move, but he makes me come a few times. He’s a soft man, a layer of fat padding even his hands. His wide, soft fingers stroke my clit in broad circles that make me greedy for his touch and annoyed with anything more spindly.
The dust and the heat. Spray bottle cool-downs. Sweating, waves of rolling tension release. I yelp as I come. I don’t put any effort at all into turning him on, I just take as many orgasms as he’ll give me because they feel good at his fat hands and I’m pouring all my effort into dressing up in cute latex outfits to try to seduce The Mad Scientist.
A couple months later The Mad Scientist and I commit to being sexually exclusive, at least for the next four years or so. Thus ends my fun romps with his roommate, but we stay friends, and he does those favors for me – the kind that let me know without a doubt that he still wants to fuck me.
This goes on for many years, even after the roommate falls in love, but stops before he gets married. By then though, I have left Los Angeles and the crowd I played with there far behind, and haven’t had any roommate sex anywhere else since.
More Sex From My Teens and Twenties: