What’s your gender? Man
How old are you? 37
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: College degree (eg., BA, BS)
What’s your occupation? copywriter
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
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)? 16
How many hookup stories have you here posted before? 3

Short Fling With a Married Woman

How long ago did this hookup happen? 14 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? Just met that day

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? “Cherish” (not her real name, obviously) was slightly older than me. I was 24 at the time, and I think she was 28 or 29. She was married, but extremely unhappy in her marriage. I never understood why they stayed together because she was cheating on him like crazy. She claimed he knew and that they only lived in the same place for financial reasons, but I’m not so sure. We met online and she sent me a few pictures. Cute with big boobs – pretty much my kryptonite.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? For someone who claimed their marriage was over, she was really paranoid and cautious about meeting. We met in a hotel parking lot over my lunch break one day. We’d been talking for a while, and this was kind of a definite thing that we were going to hook up. I got into her car, we made out some, and instead of booking a room, we went back to her place. There, she had to make sure the coast was clear because of nosy neighbors. Whatever you say. I went inside, and we went straight to the bedroom.

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 were making out on her bed for a little bit and she put her hand on my dick through my pants. She commented on how hard I was and I asked her if she wanted to see it. She eagerly said yes, and I unzipped my pants and pulled it out. She didn’t waste a beat going down on me and holy shit was it good. She then got paranoid again that her husband would use a blacklight on their comforter if I came on it (what?) so we moved to the living room. There I took off the tank top she was wearing and the biggest tits I’ve ever seen popped out. Holy shit they were amazing. I started sucking on them, and undid her cutoffs – no underwear. But she was on her period and didn’t want to fuck, so I just let her keep sucking me off until I came. It didn’t take long looking at those boobs.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? We met up one other time a month or so later. I’d gotten off of work early, so I picked her up near her house and went back to mine so we could fuck. I’d recently hit a life speedbump and moved back in with my parents, but no one was going to be home. I stopped to grab condoms on the way. We got back to my place and just as I got on my street I saw a car in the driveway. Dammit! So we turned around and tried to find a place to park the car, but couldn’t. Finally, she wanted to go down on me while I was driving and gave me some amazing road head, swallowing when I came. We were on a semi-busy highway, and another driver saw us. Cherish just looked at her and winked. Good lord, this girl.

Sadly, I never saw her again after that. We talked a few times here and there, but never got a chance to meet up again. I think I remember her saying that she finally got divorced, thank god. I felt pretty bad for her husband in retrospect and made sure not to get involved with any women who were attached after that.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), I was feeling lonely, It was easy / convenient

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

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? 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? I told a couple friends about it in a “truth or dare” type game. Didn’t go into a lot of detail, just that I’d had an experience with a married woman. They were surprised I would do something like that, but then, they never saw those tits.

How would you best summarize people’s reactions about this hookup? Relatively negative

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? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? As much as I wished I would’ve gotten to have sex with her, infidelity sucks. I never knew the true circumstances surrounding her marriage, but it still wasn’t the highest road I could’ve taken.

What was the BEST thing about this hookup? Those tits. The first and only road head I’ve gotten. The excitement from doing something I shouldn’t.

What was the WORST thing about this hookup? I think I covered this.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? As mentioned, only single ladies from then on.

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? Somewhat negative

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