by Ian O’Rourke

Gender: Male
Age: 55
Race/ethnicity: Caucasian
Current location: Mid-Atlantic U.S.
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Education
Relationship status: Married
Religious affiliation: Agnostic
How religious are you? Very
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? Dozens
How many hookup stories have you here posted before? 1

Surprise Ending

How long ago did this hookup happen? 8 months

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Booty call

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? I was reassigned last fall to a different building in my company, and was introduced to all the staff there. One woman struck me as very attractive, for her confidence and wit, as much as for her looks. She’s about 7 years younger than me, built like an athlete, long dark red hair. We saw each other every few days at work, but only spoke and flirted a little in passing. In a conversation, I unintentionally said something that revealed my marriage is not good and I might occasionally stray. Turned out, unbeknownst to me, she was in an unhappy marriage too. I had no idea she was interested in me, but apparently learning that I color outside the lines prompted her to IM me a few days later.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The messages got sexier and sexier over a period of several weeks. I invited her out for a beer after work, but she was worried about us being seen together at any of the local bars. So I suggested one that’s about 30 minutes away, in another county, and she agreed to meet me there. I just expected to take the flirting to a new level and try to figure out if taking it further was a possibility. So we meet, have several beers, lots of heavy flirting and light touching, and figure out it’s getting late and we need to get home.  In the parking lot, before going to our respective cars, I leaned in and kissed her. She pulled me in the direction of her car and said, “I didn’t come all this way to not have sex with you.” During our conversation in the bar, I wasn’t getting any of the usual go-ahead signals, and we hadn’t made any plans to actually hook up, so this was totally unexpected. I think I mentioned earlier that I was attracted to her confidence and assertiveness.

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? She sat in the driver’s seat (no pun intended) and I in the passenger seat. We made out for a few minutes, feeling each other up outside and then inside our clothes. She unzipped my pants and started going down on me. Excellent technique, considering she was hunched down in a car in a dark parking lot behind a bar. I wanted to return the favor, but the confines of the front bucket seats were not conducive to getting my head between her thighs.  She wanted to fuck, so she stopped the bj before my tipping point, struggled out of her tight jeans, swung over on top of me and down on my cock, facing me. Given our limited mobility, about all I could do was sit there squeezing her tits and sucking her nipples while she rode me. Within a couple of minutes she came twice, telling me it was her first sex in six months. Between the beers and some fear of being discovered fucking in a car in the middle of a small town, I didn’t come. It was still amazing sex.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I’ve had a vasectomy. We did not discuss STIs, nor take any precautions.

What were your REASONS for having this hookup? I was very attracted to her. Discovering the attraction was mutual was a big ego boost, and I wanted to see how far that attraction would take us.  Attractive, available partners who are willing to hook up with a married man are rare. I’m not about to let one get away without trying. This one (literally) dropped into my lap.

Were alcohol or drugs involved? If so, how much? We both had several beers over several hours. I’d say we were well-buzzed, enough to lose our inhibitions, but well short of intoxicated.

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? When I concluded that an orgasm was not in the cards for me, we decided not to hang out naked in a car in a parking lot any longer than necessary, so we pulled up our pants and buttoned our shirts and drove to our separate homes. I was a little in shock at the suddenness and unexpectedness of my good fortune. Due to our somewhat rapid departure, we didn’t discuss where we stood or what might happen next. We went out again the following week, and in the conversation I revealed that I was in a FWB relationship (didn’t reveal that it was with a mutual co-worker or her identity). She was pissed. She was interested in an affair, and expected exclusivity from me (aside from my wife, I guess). I wasn’t willing to give up the FWB. So we parted ways just co-workers again. Things are okay between us, but it’s hard to resist the temptation to flirt, and that gets awkward.

To whom did you talk about the hookup? How did they react? Absolutely no one. She is socially mobile in our community and company, and she was mortified that anyone might discover us (ironic given her apparent comfort with having public sex). She made me swear never to tell a soul, not that I have anyone I can confide in about something like this, other than this forum.

Was this a consensual and/or wanted experience for you? For your partner? Yes, for both.

Do you regret this hookup? If so, why? Not it all. It’s the stuff Penthouse fantasy stories are made of. I regret that it was a one-time deal. Then and there, she needed the booty call, but she was interested in more than just casual hooking-up, and I’m not going there.

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? The best thing? The unexpectedness of it and the fact that she instigated it. Made me feel very desirable, a big confidence boost.  
The worst thing was my nervousness about fucking in a car in the middle of town.

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

All things considered, how NEGATIVE was this experience? Not at all negative

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