by Pinakographos

Gender: Male
Age: 33
Race/ethnicity: White
Current location: Wisconsin
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Freelancer
Relationship status: In a Long-Term Relationship
Religious affiliation: Agnostic
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 0

Dreams Do Come True

How long ago did this hookup happen? About 9 months ago

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…)? Friends-with-Benefits

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? We’ll call her S. She had a full figure, fabulous curves, long brown hair, blue eyes, and a lovely smile. She was married to J, who was dating my girlfriend K. I’d originally met her a couple of years before, when she was dating a friend and neighbor of ours. I saw her and J at parties sometimes, and when K & J started dating, the four of us occasionally hung out together.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I’d always thought S was very attractive, but for the first year or so didn’t think much would come of it. Then, at a party one night, she and I flirted a bit, and at a subsequent party, started making out. The next day she asked if I’d like to go on a date sometime, to which I excitedly agreed. We went out a few times, and, sexually, made it as far as mutual masturbation. However, I came down with a serious case of social awkwardness and felt intimidated around her, so I broke things off after a few weeks.

We still saw each other on occasion, on account of K & J’s relationship, and over the course of about few months, I became much less awkward and more comfortable hanging out with her. In retrospect, I still don’t know why I felt that awkwardness, but I’m glad it abated. One evening, as she was set to depart after a dinner visit, we kissed goodbye, and she said we should get together sometime. I readily agreed, and was glad she was still interested. A few other items popped up in life that distracted me and took most of my free time, but once they were clear, I got back in touch with S, and we started back up. At the request of another partner of mine, S and I held off for a little bit on oral or penetrative sex. But we enjoyed ourselves in other ways in the meanwhile, and I fantasized often about her.

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? She and her husband J had both come over for dinner. K and J moved to the bedroom to fool around a bit, while S and I remained in the living room. We soon began making out, groping, undressing, and sucking on nipples. Then she asked if she could go down on me, and my long-held fantasies began to become true. It felt all the better for the anticipation, and I remember she gave me and incredibly sexy look as she did it. After a little bit, we moved on to intercourse, with me laying back on the couch. As she lowered herself onto my cock, I remember saying a terribly cheesy, but true, line: “sometimes dreams do come true.”

After a short ride, I came. We snuggled for a few minutes while I recovered, and then I fingered her until she got off as well. Then we got dressed and chatted while we waited for K and J to finish up in the bedroom, so that S and J could go home.

Did you have an orgasm? Did your partner(s)? We both did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used a condom. We had previously discussed our sexual histories, networks, and testing, and I had also had a vasectomy.

What were your REASONS for having this hookup? I wanted to have a pleasurable experience with an attractive person.

Were alcohol or drugs involved? If so, how much? I had none. I can’t recall if she might have had a glass of wine during dinner.

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? I felt great afterwards. It was a lot of fun, and since then we’ve hooked up every few weeks on a pretty regular basis. We are developing a great sexual chemistry, and I like hanging out with her outside the bedroom. I hope that this keeps up.

To whom did you talk about the hookup? How did they react? My partner K knows about it and was happy for me. A couple of other friends know that we hook up some times. They have been supportive. I don’t think anyone’s reacted negatively, but I also probably haven’t shared it with anyone who I think would.

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

Do you regret this hookup? If so, why? Only that I didn’t do it sooner; I don’t know what caused me to feel awkward around her, but I’m glad it got sorted out.

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? It was a great start to a positive, ongoing sexual relationship. It’s been my first sustained casual sexual relationship, and it’s made me interested in finding more such connections.

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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