What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Boston USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Scientist
What’s your current relationship status? Single
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 60
How many hookup stories have you here posted before? 1

My Roommate

How long ago did this hookup happen? 20 years

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For 1 to 3 years

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? “C” was 23, chubby, long blonde hair, large breasts, sweet as sugar, a bit naive. Very kind and caring. Her bedroom and mine were two of the three upstairs bedrooms.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was dating A seriously at the time. A week before, I had gone on an interview in another town and had cheated with my ex-girlfriend B. B was about to start a new relationship and I suddenly became obsessed with her – I decided B was the only one for me. So one night after about 4 beers, I called up B and asked her to marry me. She said she would think about it (later said no).
After I hung up I was in complete emotional chaos – dating A, wanting to marry B, then having second thoughts about B. My mind was out of control. I went across the hall to C’s room. I asked if I could talk to her and I said sure. I got under the covers with her. I told her I had just proposed to B and wasn’t sure if it was the right thing. I just poured my heart out. She was really sweet and nice and put her arms around me. I’d always thought she had a crush on me. So after a while, I kissed her and she went with it. We kissed passionately for about 15 minutes. She was wearing a long heavy cotton nightgown. Instead of doing some preliminary touching and seeing how she responded, I just tugged on the nightgown and said: “May I take this off?” She said “Sure” and immediately pulled it over her head. She was starkers underneath it.

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? We kissed and kissed and I caressed her large breasts and fingered her. I fucked her missionary for about 15 minutes but was too drunk to orgasm. Her breasts were so larger they were pendulous which I don’t really like. Although she’d only had a few partners, her pussy was really loose and didn’t
provide much friction. We cuddled and slept.

In the morning I felt crushingly guilty, but I figured, what the hell. We fucked again, this time cowboy. I tried caressing her clit while she rode me but she said she didn’t like it. Even though her pussy was so loose, I was 27 so I eventually came inside her. We cuddled and kissed and I went back to my room. I felt so guilty.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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 talked about it and agreed to keep it on the down low. About 4 months later when I’d broken off with both A and B I went into her room (drunk) one night and had a repeat. Her tits were still unattractive to me, her pussy was still too loose, and that time I didn’t orgasm at all. Neither did she.

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), Intoxication, To cheer myself up, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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? I don’t know / I’m not sure

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? Somewhat

Did your partner get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? A little bit

Why do you regret this hookup? Complex situation, cheating on two girls at once, guilt, and I know it hurt C’s feelings although she never said anything.

What was the BEST thing about this hookup? When I asked if I could take her nightgown off and she did it herself. She went from a conservative girl in thick sleepwear to stark naked in 5 seconds.

What was the WORST thing about this hookup? A little too tipsy, didn’t perform well. Guilt.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

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

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? It’s fine if you are ok with it.

What do you think about the Casual Sex Project? Good.

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