What’s your gender? Man
How old are you? 31
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? U.S.
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Writer
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? None
How many sexual partners have you had in your life (including oral sex)? 11
How many hookup stories have you here posted before? None
I Think About it Every Day
How long ago did this hookup happen? 3 years ago
What was your relationship status at the time? Dating casually
How would you best classify this hookup? Friends-with-benefits
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 a short-haired brunette with a kind of impish gaze that had me curious about her. Personality-wise, she was my polar opposite and that’s actually why I reached out to get to know her on the dating site I was on. I had dated several women who I had been matched with and had no success. I think I was feeling a little rebellious and we weren’t even close to being a match. I remember messaging her saying, “Apparently we’re not supposed to get along. Want to have a conversation?” She responded almost immediately in good humor and we chatted about life from two different perspectives. I wasn’t into her romantically, nor was she into me but we agreed to meet for a drink.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We hooked up countless times over the course of a year, always at her apartment. The idea of having sex was interesting because she was so open about her sexual tastes and since she didn’t see me as a sexual partner, she felt free to just be herself. I respected her confidence and realized I didn’t have the same freedom. I had grown up very religious and held on to correlation of sexuality being shameful, even though I had multiple partners before I met her.
Listening to her talk about sex made me envious of her liberating outlook. I asked a lot of questions and through the conversations, the idea of she and I hooking up developed from something we didn’t consider to something we both really wanted to try.
Ultimately, I instigated what felt like had been building up for weeks. I’m sure if I hadn’t, she was about to.
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? I wouldn’t have the first clue how many times we hooked up, but the first time was a little awkward, albeit very exciting for both of us. She was experienced in BDSM and I knew zero about that lifestyle but was intensely curious. She was a sub and wanted a dom. I had no idea what I was or what I would like so I tried both and discovered an entire personality aspect about myself as a dominant. I enjoyed giving her what she wanted, listening to and learning her boundaries. I can’t even say I was timid to start out. I’m happy I let her dominate me first to get an idea of what being spanned, caned, whipped, denied, choked, spit on, tied up all felt like. It gave me the confidence to give it back to her. I remember getting hard just from watching her writhe in anticipation, scream in satisfied pain/pleasure. She would give me this look with tears in her eyes, laughing through it all, she felt relief from something and I did too. I felt alive and she said the same to me. I stayed hard the entire time, and the instant I felt her mouth on me, it was like nothing I had ever felt before. I wanted to stay wrapped up like that forever. We both came several times over and realized we had just opened a door to something exciting and scary and irresistible.
I couldn’t get her out of my head and she said as much to me. The best sex we ever had is still the best sex I have ever had, without question.
I was house sitting for a friend near her apartment and we hadn’t hooked up since that first time. It had been several weeks and we were dying to see each other again. I told her I was nearby and she told me to come over immediately. When I got to her place, she had left the door open and was waiting for me on her bed, in this black lace corset, fishnet stockings, and a little bow in her hair. We fucked for the entire day, stopping here and there for little breathers where we would learn about each other’s different life philosophies, but we never communicated like we did when we were fucking. Nobody has ever been able to know what buttons to push on my body like she was. Not even close. When she would touch me, I felt so validated. I felt fearless, invincible, powerful, I felt worthy. She knew when to be gentle and when to fuck hard. We memorized every inch of each other.
Every time after that was picking up where we had left off, ultimately realizing we didn’t work in any aspect other than through our sexuality.
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? Our communication grew toxic and the dynamic became contentious. We grew to resent each other unless we were in bed. I fell in love with the woman who would become my wife and she had fallen in love with another man. We knew in order to have the lives we wanted, we had to end and so we cut ties and haven’t spoken in 3 years.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Birth control pill / patch / ring / injection / implant, Discussed STI testing history, Plan B / Emergency contraception
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, I was feeling lonely, Power / Dominance, Submission / Relinquishing power, Making new friends
How intoxicated were you? Not at all (no alcohol or drugs)
How intoxicated was your partner? Not at all (no alcohol or drugs)
Did you consent to this hookup at the time? I gave enthusiastic consent
How wanted was this hookup for your partner at the time? Very
Did your partner(s) consent to this hookup? They gave enthusiastic consent
To whom did you talk about the hookup? How did they react? She would tell her closest friends about me and they would criticize what we had which is fair. Nobody in my life understood it but the second we were in bed together, nothing else on the planet mattered.
How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)
Did you get emotionally hurt as a result of this hookup? Very
Did your partner get emotionally hurt as a result of this hookup? Very
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? Learning how to be with someone in a new way, learning how to let go and embrace my sexuality, but most of all, the experience of learning about someone who was so fundamentally different from myself.
What was the WORST thing about this hookup? We had zero romantic chemistry and it started showing it’s head after our third hookup. It drove us apart and I wish we had the ability to keep mutual respect.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Absolutely in every way.
All things considered, how POSITIVE was this experience? Fairly positive
All things considered, how NEGATIVE was this experience? Fairly negative
Anything else you want to add about this hookup? I still think about it a lot. I think about what I learned while being with her. I don’t miss her and I dare say she doesn’t miss me. I do wonder if she misses our sex. It was more than fucking. It was something transcendent.
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? Casual sex is a valuable form of sexual expression. I believe strongly I wouldn’t be the man I am today, nor would I be able to care for my wife as much as I do without some of those experiences.
I would like to see open conversations about sexuality in our society and to eradicate the shame involved on any level.
What do you think about the Casual Sex Project? Reading other people’s stories made me want to share mine.
You have a hookup story to share? Submit it here!