First Of Many

by Connie

Gender: Female
Age: 35
Race/ethnicity: White
Current location: South Korea
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Teacher
Relationship status: Single
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Bisexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 0

First Of Many

How long ago did this hookup happen? 16 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, short fling; paid sex…)? Short fling

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? My partner was a short, thin white guy with bright red hair, blue eyes, and glasses.  I was 19 and he was in his late twenties; he was also married (separated), AND my boss.  We were always friendly toward each other at work and when our conversations became more flirtatious, he invited me over for dinner.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had dinner at his place, then listened to music and played the guitar together.  We talked about his separation and why his marriage was ending; he started rubbing my feet, which led into more sexual touching, and it went 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? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We had missionary-style vaginal sex.  I wasn’t particularly turned on by him and it wasn’t great sex, but I was really enjoying the taboo aspect of it.  I had fun despite not being really aroused; we probably engaged in some playful banter, but I don’t particularly remember what we talked about.  He was a gentle lover, but didn’t seem that concerned with my pleasure (but not greedy, either; just kind of going through the motions of the type of sex you see in movies).  It ended with a little chat and a cuddle, then I put my clothes on and drove home.

Did you have an orgasm? Did your partner(s)? I didn’t climax, but he did.  I faked an orgasm because I thought it would make him happy… this was long before I learned to speak up and take control of my desire / pleasure.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We didn’t discuss STI history; he wore a condom, and I was on birth control pills.

What were your REASONS for having this hookup? My reason was that I found it exciting and edgy to be having a fling with my married boss!  It was my first experience with casual sex, and I enjoyed the idea of being able to have sex with someone without an emotional entanglement.  I had just come out of two serious relationships in a row, and it was nice to not have to worry about hurt feelings.

Were alcohol or drugs involved? If so, how much? I had a glass of wine with 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? Neither of us had expectations; we had sex a couple more times after that, and then I think he started working things out with his wife.  He was considerate of my feelings, but I didn’t really have romantic feelings for him, so I remember being kind of relieved when he got back together with his partner because the sex wasn’t that good.  I have neutral feelings about him now; I haven’t seen or talked to him in over a decade, so I really don’t think about him.

To whom did you talk about the hookup? How did they react? A couple of coworkers; they found it hilarious!

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

Do you regret this hookup? If so, why? Not at all, nor any since.

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 about it was that I discovered at a young age that love and sex are not necessarily intertwined.  That I could have sex JUST BECAUSE sex is fun.  Can’t think of a worst thing, unless he and his wife had made an agreement not to sleep with anyone else during their separation.

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

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

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