by Everett

Gender: Bigender, although solely identifying as male at the time of this story
Age: 28
Race/ethnicity: White
Current location: Boston
Highest education received: Post-graduate degree (currently pursuing)
Occupation: Web developer
Relationship status: Single
Religious affiliation: United Methodist
How religious are you? Somewhat
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Attracted to women, regardless of my gender presentation or mood
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 2

A Summer Weekend…

How long ago did this hookup happen? 2 years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Friends with benefits

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? “J” and I met on OkCupid over a summer while I was in grad school. I had just gotten out of an emotionally abusive distance relationship and I was looking to find somebody more local and who would be better to me. “J” wasn’t quite local, she was in a city about an hour away from where I lived at the time but we sent messages back and forth a few times, but nothing really came of it. I ended up meeting and starting to see somebody else and deleted my OKC profile. Fast forward a few months and things didn’t work out between me and the new girl. Eventually I was ready to try again and recreated my account. Sure enough, the first person to pop up was “J”, and we started chatting again. This time we exchanged numbers and had phone conversations that went well into the early hours of the morning. She was intelligent, funny, laid back, caring, free spirited, and by her photos really cute too – short Korean American with long black hair, a few visible tattoos on her arms and a gorgeous smile. A few days later I made an excuse to come up to her city and suggested we grab dinner, and she was happy to oblige…

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met in a local coffee bar around 5 in the afternoon. I could tell immediately our dynamic in person was different, and I didn’t think we had the physical chemistry we were hoping for. Nonetheless, I’m a sucker for intelligent conversation (hey, brains are sexy!) so I stuck around. After coffee place closed, she invited me back to her apartment and we could cook dinner, dinner turned into lying out in the park across the street under the stars while we split a pack of cigarettes and drank dogfish beer. I didn’t think we had much physical chemistry but her body language said otherwise, she was very cuddly and by this point it was one in the morning. She suggested I stay over, and we could even put a movie on…

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 went back inside, put something on Netflix and almost immediately started making out. Clothes came off pretty quickly, I went down on her, she sucked my dick for a bit and then we just fucked. Nothing too out of the ordinary or kinky but really satisfying and I felt incredibly comfortable with her – we had a great emotional connection before and it turned out we did have some awesome physical chemistry after all.
We were both exhausted afterwards and fell asleep in each other’s arms.

Did you have an orgasm? Did your partner(s)? I think she had a small one, I did not but it was still satisfying regardless.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condoms, and we talked quite a bit about our histories. We agreed to both get tested if we started to do anything sans-condoms.

What were your REASONS for having this hookup? I was really into her and it just happened.

Were alcohol or drugs involved? If so, how much? We both had a beer or two but we were by no means “drunk”.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? The next morning she had to work but said I was welcome to stick around, later afternoon we could go swimming in the creek. I was intrigued, so I went home to shower and change while she was at work and came back with my bathing suit and a change of clothes. Swimming with her was a lot of fun, lots more deep conversation, this time between kisses and teases under water. We headed back to her place when it started getting dark, had some amazing shower sex and fell asleep cuddling again.
The next morning I had to work, so we said our goodbyes, she said she’d love to see me again, and asked if I was open to the idea of being friends with benefits for a while, with the caveat that it could develop into something more down the road. I was more than happy to oblige, we kissed and I went on my way.
She met the guy who became her boyfriend shortly thereafter and I ended up meeting the woman I would be engaged to for two years, but we stayed in touch for a while until she moved out of state.

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

Was this a consensual and/or wanted experience for you? For your partner? Absolutely on both accounts.

Do you regret this hookup? If so, why? Not at all

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I approached it with the idea that if things worked out it’d be awesome but if not I still got an awesome friend out of it and that’s how she saw it as well. After many years of catholic guilt, I think she was the one who finally helped me let that go and realize that sex can truly be a wonderful thing in it of itself.

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

All things considered, how NEGATIVE was this experience? Not at all negative

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