Long Time Coming



What’s your gender? Man
How old are you? 35
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: College degree (eg., BA, BS)
What’s your occupation? Business
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 30
How many hookup stories have you here posted before? 0

Long time coming

How long ago did this hookup happen? 1 year

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For more than 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? Paige and I knew each other for over 10 years. We were both part of a big friend circle that centered around a big firm that I worked at with a buddy who had dated her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A group of us were at a bar for Paige’s going away party. She was soon moving to Chicago after nearly a decade in Boston. In our mid-30s, none of us were big drinkers anymore but that night was a special occasion. Around midnight, the party started to wind down and it was determined that I would walk her home and crash on her couch instead of taking a car back to my place across town.

We walked into her apartment and sat down on the couch. Not in the usual “Mike and Paige sitting across the couch drinking tea” position” but rather right next to each other. I could see it coming.

Years of flirting and sexual tension came flooding out and we began to kiss on the couch, in that deep, sexual kissing that serves as abbreviated foreplay when two people can’t wait to fuck. In an instant we were in her bedroom, tossing clothes on to the floor as she climbed on top of me. The conversation went like this: “I’m good. You good?” “YES” and with that I was inside her.

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? It may have been the best sex for a one night stand that I’ve ever had. We both were well into our sexual lives and the sex we had showed it. We effortlessly cycled through positions: cowgirl, doggy, missionary, spoon. We switched to oral at times to mix it up. We knew each other so well that even though we’d never even kissed before that night, the sex just flowed naturally.

With my orgasm approaching, I asked her where she wanted it and she gave me the answer I’d been hoping for. She wrapped a leg around me tightly and I came buckets into her.

We fucked two other times throughout the night and morning, each time ending with mutual orgasms and me cumming inside her.

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? The next morning after one final session, we laughed about how long we’d known each other and what the rest of the group might think.

Now that we’re a plane ride apart, we stay in touch but haven’t had a repeat act. Both of us are in new relationships and I’m not sure what would happen if we got together again. We’re still the same old friends we were before.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) IUD (Intrauterine device), Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Intoxication, Just happened, I don’t know why, just went along with it

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

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? Not at all

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The sex. Breaking years of sexual tension. Her riding my face to orgasm.

What was the WORST thing about this hookup? We had been drinking, would have been more fun sober. We also should have talked more about it afterward. I’d like to know how she feels about it, but there’s still time to ask.

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? Very 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? I love casual sex. I wish society were more accepting of it – and am happy it seems to trend that way. Provided all involved are honest in their participation and understand risks, I think it’s a wonderful thing.

What do you think about the Casual Sex Project? Awesome! I’m new here and can’t wait to explore more. I’ve got a few more stories that I hope to post.

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