My Roommate



What’s your gender? Man
How old are you? 53
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
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Scientist
What’s your current relationship status? Single
Religious affiliation: Unworried
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 60
How many hookup stories have you here posted before? 2

My Roommate

How long ago did this hookup happen? 17 years

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than 6 months

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? She was 23, I was 32. I bought a house but needed to rent one room. She was in a purportedly monogamous relationship but her bf lived in another state. She was short, fit, super cute, great smile, tight ass, b cups.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We became inseparable. Went out to dinner, to movies, etc. Often would sleep platonically in the same bed. After perhaps six months, we went for it. We were sleeping together and we just stripped and had at each other. She was super fun in bed, tight body, loved oral, open minded.

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 fucked like bunnies for ~10 days. Then her bf came for the weekend. She clearly was expecting me to be upset – and then that would lead (in her mind) to us being a couple. I wanted to be single so I didn’t care that her bf was there. She was upset and broke off.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

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

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

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

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? Somewhat

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Great sex

What was the WORST thing about this hookup? Over too soon

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

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