Whoops, It’s Probably Fine



What’s your gender? Man
How old are you? 36
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Gainfully employed and Busy
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation:
How religious are you? A little
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 18
How many hookup stories have you here posted before? 0

Whoops, It’s Probably Fine

How long ago did this hookup happen? 1.5 years ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a month

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? S is about 5’7″, thin, quite fit with wavy brown hair, and a stunning smile made all the more beautiful by how thoughtful and serious she looks when she isn’t smiling. I matched with her on Tinder and we chatted back and forth. I wanted to try Tinder because I was convinced my divorce was imminent and I wanted to see what dating would be like. I was attracted to her because she was not only gorgeous and sexy, but really intelligent and thoughtful, with a great sense of humor. We had been on one date that went pretty well, but I had no idea what I was doing, having been married for quite a while. About a week later I got a random text from her saying she was house sitting and she invited me over to binge watch HBO and celebrate her finishing up classes. I was excited, but pretty nervous. She warned me that she was in full lounge mode and not made up at all, which I prefer anyway.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She answered the door in sweat pants and a sweat shirt, with her hair pulled up. She hugged me at the door and invited me in. We started watching the show and she was really into it and would explain the context to me. It was pretty casual, so I wasn’t sure if she was interested at all. Eventually, I put my arm around her and she snuggled in so I thought things might progress. Once the credits rolled on the first episode or so, I got up the courage to try and kiss her and she reciprocated. My heart was pounding, but it was so natural and sweet, like we had known each other much longer. The autoplay on the next episode kicked in and we went back to watching the show. I didn’t want to assume it would go farther than that, but then she took off her sweatshirt to reveal a little white spaghetti strap undershirt. I remember it almost like it happened in slow motion, and she smelled amazing, but it wasn’t perfume, just her. I took this as a pretty obvious sign that she might be interested.

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 gently touched her face and moved in to kiss her and it was a bit different this time. There was more intensity and urgency. We rolled over on the couch so I was on top of her and I started kissing her neck and moving my hands to her hips. All the while I was kissing while her breathing quickened. I slid my hand down her back and under her sweatpants and then felt around. She was soaking wet as I teased her clit and slid one finger inside her. I kissed her all the way down until I slid my tongue over her clit keeping a finger inside her. Her taste was completely intoxicating.

When she said she wanted me, I put on a condom and we slowly started having sex. Everything was so intense and she is so gorgeous and tight that I could barely hold it together. After a few minutes I came, but I didn’t want to leave her unsatisfied or disappointed, so I went down on her again and then excused myself to the bathroom to put on a new condom. I came back and we picked up again, but this time she got on top on took over, and oh my God, she can move. She leaned back, bracing herself on my knees, and rocked her hips in the most amazing way. I pushed all the way into her as I felt her move back and forth. She came hard and collapsed on to me, sweaty and spent. It was incredible. Then, I noticed that the front window with a full view of the couch had been open the whole time we were going at it for the past two and a half hours and we laughed saying, oh well, at least we put on a good show if anyone saw.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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? She fell asleep in my arms, naked, on the couch, and it was so sweet. I just listened to her breath against my chest and reflected on how lovely she is and how surprisingly sexy she could be. I did have the thought that she may have been on Tinder a fair amount given how talented she was on top, but I didn’t mind because I was flattered she found me attractive. She invited me to stay the night, but I had to go home around 3 am. We dated for about a year after that, but only had sex 1 or 2 more times, so I figured I was not a high priority and we drifted apart. Also, we left an impressive wet spot on her cousin’s couch that night, which is probably a faux pax when house sitting, not to mention the wide open, well lit window.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

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

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? No one. I saw her the next day and she teased me about the couch burns on her feet from her exquisite riding skills

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? Everything about her and especially how turned on she was and how amazing she smelled and tasted when I went down on her. I get vivid flashbacks about it from time to time.

What was the WORST thing about this hookup? That I felt like I couldn’t perform at my best in control because I was so turned on and nervous.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Definitely. It made me realize that you can connect with different people in different ways. Sex and love are additive and should be open as long as you are safe. My wife does not agree, despite discussing this at length, but we will have to agree to disagree.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? Please check your windows and couch when house sitting. Especially if you are going to get down with a new love, or any love.

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? Sex is beautiful when people come together safely and with full consent. It never feels casual, but can be had casually.

What do you think about the Casual Sex Project? It’s wonderful and I appreciate everyone’s contributions.

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