by VeryClarkKent

Gender: Male

Age: 30s
Race/ethnicity: South Asian
Location: Pacific Northwest
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Engineer
Religious affiliation: Agnostic
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
How many hookup stories have you here posted before? 0

Scratching an Itch

How long ago did this hookup happen? 10+ years ago, I was in my 20s and a few years out of school

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…)? A friendly favor

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? When I first moved to this area after university, I worked for a web startup that didn’t last long but gave me a very good, core set of friends. She (M.) was the girlfriend of one of my old ex-coworkers (T.), so was always a bit Out of Bounds; but there was definitely a fondness that we shared for each other. At the same time, I was in an on-again/off-again long distance thing with a girl from school who I just couldn’t let go, and M. was always a good sounding board and dispenser of advice for any woes or angst that I was experiencing. Both M. and T. were a bit older than me, and I think that they enjoyed the teacher/student thing going on between us.

M. also looked almost exactly like one of my exes (actually the person who was My First) and I am sure that was a massive factor in my attraction to her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were out at our usual neighborhood bar night, where M. and T. had just announced that they were getting engaged. He was off playing pool with a bunch of the other guys, and I was sitting at a stool next to M., asking about plans. She leaned over and said, “you know, T. and I were talking and… before we get married, before the bachelor party and all of that… we want to give each other a chance for one night with someone else.”

My on-again/off-again was in its distinct (and now permanent) off-phase, so, finally, this boundary between us was kind of erased and we both knew it. So while her fiance was all of ten feet away at a pool table, I just looked right into her eyes and I said, “ok.”

It was more of an agreement to the idea of hooking up rather than an invitation to plan anything. We agreed that it would be a one time thing, to just scratch this itch that we both built up for each other, and I could talk about it with her fiance, but we’d otherwise stay discreet about it. We didn’t talk about it for a while afterwards, but eventually, a few months later, she told me that her fiance was going out of town to meet up with an old flame of his with whom he had some ‘unfinished business’ and she was wondering what I was up to for that weekend.

We made plans to meet up for dinner on Friday, and it was nice… and also possibly the first time that the two of us were ever alone in the same room. At some point in the conversation M. let drop that she and T. had gone ahead and already gotten hitched at city hall. They were still going to have the formal wedding and everything in a few months; but they were also in the middle of buying a condo and stuff, and it just made financial sense for them to be married at this point.

My brain could listen and understand that this was just a finance and paperwork thing, but for some reason, I couldn’t get over the fact of, “oh, you’re -married- now. I don’t know if this is what I signed up for.”

All the same, we finished our dinner and agreed to go back to her and T.’s apartment. We pretty much started making out as soon as we got in the door, and then proceeded to the bedroom straight from there.

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? We started with mutual oral, which led to her straddling me and initiating vaginal sex. Unfortunately, I kept overthinking about the “we’re married now” bombshell and this also led to questioning exactly what we wanted from each other. I felt like she should have told me about this earlier and that I had needed time to figure out if I was ok with it, even if it was mostly just symbolic.

Needless to say, that distraction and ambivalence was a bit of a drag on the rest of the night, and I had trouble maintaining an erection. It was my first encounter with a failure to perform, and sort of led into a death spiral of anxiety and doubt. In the end, I got her off orally that night and did not climax myself. We agreed that was ok, and we just cuddled with each other to sleep.

In the morning, she initiated sex again, and I left my hangups behind and it was nice. She orgasmed first, and I followed shortly afterward. We cuddled for a bit through a lazy Saturday, but I didn’t stay long after lunch.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We wore condoms for both bouts of vaginal sex, but we did not use any precautions during oral. We discussed STI history when she initially propositioned me.

What were your REASONS for having this hookup? Interest, lingering attraction, some loneliness, and — to be honest — a certain pining for an old flame, who she wasn’t but I wanted her to be. I am not proud of that.

Were alcohol or drugs involved? If so, how much? We split a bottle of wine, but that was it.

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? After that weekend, I realized that I was in a kind of a terrible headspace with some baggage that I needed to sort through from my last relationship. I took a couple of years off from dating and just focused on being happy with myself. The two of them got married, and I visited their condo quite a few times over the next few years, but the tension between us was resolved and we didn’t hook up after that. Our overall intimacy with each other had diminished. I think we were both uncomfortable with how things ended, but we didn’t really talk about it afterwards and just left it in the past.

They moved to a bigger home out in the suburbs after they had their first kid and, like many couples with children, they disappeared into their own world. I still see photos of them pop up on Facebook, but that’s about the extent of it.

To whom did you talk about the hookup? How did they react? Brief chat with T. beforehand just to make sure he was on board with all of this. Nobody else needed to know. I never really discussed the night with T. afterwards either.

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

Do you regret this hookup? If so, why? I don’t know. I think that this was a catalyst for a lot of growth, but I sort of regret how things happened. If I had to do it again, I would, but perhaps would’ve let go about hangups earlier so that we would’ve had a more fun evening.

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? To be selfish, the best thing about this was that it was the first time that a woman had clearly expressed an attraction to me, and had made me feel wanted and confident about myself. All of my past relationships at that age did eventually have mutual attraction, but they were always initiated by me, and I always felt like I had to work to get the other person to notice me. It’s nice being pursued for a change, rather than being the pursuer. I also wound up getting involved in other open relationships in my friends circle, and this was a good introduction to that sort of unconventional dynamic. At the very least I got a rough intro to the importance of communication, communication and more communication — even for something that’s just a ‘one time thing’.

The best long-term thing was also having this be an occasion to confront my baggage about being in a relationship simply to avoid loneliness. The two years of romantic solitude that followed this incident were some of the best personal development years of my life.

The worst thing was this sort of feeling like a friendship between two formerly important people in my life went into a decline afterwards. I think she felt like she was responsible for how things went, but we never really talked about it afterward and just drifted apart. I had to learn to be more open about talking about uncomfortable things, and I’m sorry that a friendship had to suffer to learn that lesson.

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

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

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