First Sexual Encounter

by Barry

Location: East Tennessee
Highest education received: Some college (not currently in college)
Occupation: Unemployed
Religious affiliation: Protestant
How religious are you? A little
Sexual orientation: Mostly heterosexual
How many hookup stories have you here posted before? 0

First Sexual Encounter

How long ago did this hookup happen? About 2 years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, paid sex; something else.)? Something else: Unexpected hook up

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? Jenn was a couple years older than me. In online dating lingo, she would be described as having a few extra lbs I guess. She was a friend of a friend, we had met before during prior get togethers with our mutual friend but had never talked other than saying a cursory “hi” to each other. She also lives in a town about 2 hours away.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was the birthday party of our mutual friend Lizzy which we both were attending. It started at Lizzy’s apartment and progressed to a local club. Jenn spent most of her time on the dance floor with Lizzy and the other girls while the guys & I did not dance and lounged around talking or looking at their phones. As it neared closing Jenn came over and sat down next to me and got quite cozy and semi-cuddly. I was one of the drivers since I didn’t do any drinking and Jenn elected for me to drive her back to Lizzy’s place, as she was somewhat inebriated to the point of stumbling. About a third of the way back to the apartment Jenn unbuckled and started licking around my ear. After a few minutes of that she put my hand under her bra and let me cup her breast. Another minute though and we arrived at Lizzy’s place and went inside. She cuddled up next to me on the couch as we all conversed for the next hour or two and eventually put a blanket over the both of us. Unbeknownst to the others, under the blanket she put her hand in my pants and was discreetly stroking my cock.

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? The stroking continued as the party wound down and people went home. She got up to use the bathroom after awhile and whispered for me to accompany her. Upon entering we started making out. After several minutes of that we went back to the living room, everyone else had retired to their bedrooms and we were left alone. We continued with making out, she took off her top and I sucked her nipples. She eventually took off my pants and performed oral on me to completion. We lied there awhile before I said I had fun and had to get home. She said she enjoyed it as well and we said goodbye.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None

What were your REASONS for having this hookup? She initiated it, and I went along with it. I wasn’t attracted to her, but would have felt awkward rejecting her. Having never had any sexual encounter other than a lap dance at a strip club, I also just wanted to finally have the experience despite the lack of interest in her.

Were alcohol or drugs involved? If so, how much? Enough alcohol that she was inebriated immediately following the club excursion. A couple beers on my part over the course of the entire night.

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? She began texting me fairly regularly afterwards, which I would respond too. We had a couple other hookups over the course of the next several months when she came back in town to visit our friend. They went more or less like the initial one, though with less alcohol. The third and last encounter progressed to me giving her oral as well. While she was game for penetration, I had trouble staying hard enough and ended up cumming on her stomach. The next time she came to town after that she was in a relationship with someone from her town, so that ended any further encounters to my relief.

To whom did you talk about the hookup? How did they react? Didn’t discuss with anyone. I heard later through my brother than Jenn had mentioned it with Lizzy understandably, however Lizzy and I never talked about it.

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

Do you regret this hookup? If so, why? While I wasn’t that into it, in hindsight I wouldn’t say I regretted it. I guess I would say I remain ambivalent about it.

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? I could now truthfully say I had a sexual encounter.
I didn’t get that much enjoyment out of the encounters. Even though I had an encounter now, it didn’t really do much for my confidence as it was not with someone I found desirable. Also, I felt douchey for continuing the encounters despite lack of desire.
In the grand scheme of things though, it’s just a couple people hooking up one of which isn’t invested in it. Then it ended, no harm no foul. Not a very unique situation in the end I guess.

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

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