What’s your gender? Man
How old are you? 51
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, Ph.D., JD, MD)
What’s your occupation? Attorney
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Pansexual
Any other term(s) that describe your sexuality or sexual identity? Slut
How many sexual partners have you had in your life (including oral sex)? 100+
How many hookup stories have you here posted before? 1

Sex With My Roommate

How long ago did this hookup happen? 20 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For less than a month

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? When I was in law school, my roommate Mark was in grad school. We shared a two-bedroom apartment after meeting through campus housing assistance. He was a nice guy, skinny and preppy, with blond hair, blue eyes. He had his group of friends as did I, so we didn’t hang out much together. One afternoon, I came home early from school to find him getting fucked on our couch. The guy was frantic and left as soon as he could get his clothes on. Mark ran after him. When he came back to the apartment, he was mortified that his secret has been found out and afraid I would want to move out because he was gay. Mark and I went to a private Catholic school, so nobody was truly out. Instead of being angry, I simply told him that I hoped he never caught me in the act with a girl or a man. He became the first person I ever came out to, and we developed a nice friendship after that.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? About two weeks later, I came home after Happy Hour on a Friday night and decided to shower before figuring out what I was going to do that night. Mark came home at about the same time. I asked him if he wanted to join me in the shower, partly in jest, partly because I thought it might be fun. He joined me.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? Once he came into the shower with me, we kissed for about a minute, a nice passionate embrace with just enough tongue. Then, we started washing each other over our entire body with a lot of special care around our cocks and asses. After we spent about a half hour getting nice and clean, we got out of the shower, and I started kissing the back of his neck and grinding my cock against his ass, almost penetrating. I fingered his hole, which was nice and lubed up from all the soap. He suggested we move to his bed. He grabbed a condom from his drawer and handed it to me. I got the condom on, put him on his back and raised his legs. My hard cock was inside his hole in seconds, and Mark was screaming with delight. I came in less than a minute given how hard I had gotten in the shower and bathroom afterward. But Mark wouldn’t let me out of this ass when I came. I had softened up some, but not much. He told me to keep fucking him, which I did for another 15 minutes. He came about halfway through this run and having his cum splattered all over us just made it that much hotter. Finally, I came again. We kept fucking all weekend long. He fucked me next. Sometime on Saturday night, we ran out of condoms. Instead of stopping the fucking, we kept going. This was my introduction to barebacking.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? We kept having sex for the rest of the school year, never putting on a condom with each other again. We’d also have sex with others (men for Mark; men and women for me). He graduated and moved to NYC. He called me a few months later to tell me his HIV test came back positive. My test came back negative. Fortunately, I’ve stayed negative since then, and Mark’s meds have worked great. We keep in touch occasionally and did hook up a few years back when I had a business trip to NYC. But I’m married to a woman now, and he has a partner.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Somewhat

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Nobody.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? The riskiness of unprotected sex.

What was the BEST thing about this hookup? The sex.

What was the WORST thing about this hookup? That we started down the road of bareback sex that would lead to Mark becoming POZ.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It made me enjoy sex with men more. It was the first time I had ever known the name of a man I slept with more than 2 hours before having sex with him.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? A little negative

You have a hookup story to share? Submit it here!