Gender: Bigendered (although at the time identifying solely as male)
Location: Upstate NY
Highest education received: Post-graduate degree (currently pursuing)
Occupation: Call Center Supervisor
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 hookup stories have you here posted before? 0
At long last…
How long ago did this hookup happen? 3 years ago
How would you best classify this hookup? Best friend sex
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? “Laura” and I had known either other since our first day of high school and we’ve always been, and still are, very close friends. We never dated although I always had feelings for her.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was home in Massachusetts for a few days and my father invited me up to a party his fraternal group was throwing in Boston for Memorial Day. He stayed at a hotel but there wasn’t an extra room for me there, so I called Laura (she lives in Boston) to see if I could crash at her place. We hadn’t seen each other in a few months so she was up for it, suggesting I either “walk off with some liquor from the party” or if that didn’t work to stop at the package store. I left the party early, bought two bottles of wine and I was on the T to Southie.
I got to her place, she popped in a movie and we opened the wine. She knew things weren’t going well with my girlfriend at the time (who had given me permission to open up the relationship after she admitted to being unfaithful) so needless to say we were much physically closer than we might have been otherwise. Imbibed chatting and reminiscing turned into imbibed cuddling, which led to imbibed confessions that we both had feelings for each other in high school (but were either too shy/awkward/attached to say anything) which turned into lots of kissing. I went to the bathroom and when I came back to her room she was naked and suggested I be naked as well.
What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? It was very sensual and romantic, more like incredible relationship sex rather than a drunken hookup. She loved sucking my dick, I returned the favor to her pussy, followed by several different positions along with lots of cuddling and kissing in between. After three or four orgasms for both of us we fell asleep in each others arms. We woke a few hours later, made love again, took a shower together and I cooked her breakfast before work. We then rode the T back to downtown Boston and we shared one more long kiss at South Station together.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? She was on the pill and we also used condoms.
What were your REASONS for having this hookup? Opportunity, I guess.
Were alcohol or drugs involved? If so, how much? Two bottles of wine…
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? I went back to New York a few days later and we started chatting by Skype regularly, sometimes naked, although for the first time in our lives we actually talked about the idea of a relationship and me moving back to MA. I had been considering leaving my unfaithful girlfriend for quite some time and Laura and I were loving the idea of finally giving each other the chance we deserved. Two weeks later JetBlue was running a special and I flew back to Boston to see her. We got a hotel room and spent another night together of passionate lovemaking.
It wasn’t meant to be for us though, I started grad school that fall in another part of NYS, and she ended up meeting the love of her life. They married last year and I couldn’t be happier for her and him – they’re great for each other. Laura and I are still close friends.
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
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 actually believe it needed to happen, Laura and I finally got out ten years of pent up emotions for each other and were in a better place when we met our respective spouses. It also proved to me that we could hook up and not ruin our friendship even in the slightest.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
What did you think about this story? Tell us in the comments – just be nice!
You have a hookup story to share? Submit it here!