My BOSS hookup

by Rusty

Gender: Male

Age: 24
Race/ethnicity: Whitey
Location: Minnesota
Highest education received: Some college (currently in college)
Occupation: Unemployed like a bitch
Religious affiliation: Agnostic
How religious are you? Not at all
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? 0

My BOSS Hookup

How long ago did this hookup happen? 2 months

How would you best classify this hookup? 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? She was a curvy lady. Bigger than most of the other girls I’ve been with. She was very pretty and cute. I had known her for half a year. She was my boss at work. I had always thought she was cute and had flirted with her while working together.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Our job was seasonal so when it was over, she moved away. A few months later she hit me up saying that she was coming back. From there we began texting and making plans for when she came back. She would text me late at night saying she was drunk and we began testing the waters of sexual acts. We went out for drinks and I went back to her place to spend the night. We both knew what was going to happen.

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 were both semi-drunk. We started making out on her bed. She was extremely rough right off the bat. Pressing very hard when she kissed me. I began to finger her and she started losing her mind. After she came, she climbed on top of me and teased me by sucking my dick for 5 fucking seconds. Then I did the same to her, but giving her oral for a short time. She then directed me to the “condom box” and I put one on. I don’t know if it was because the condom was too small, that I was drunk, or it had been quite awhile since I’d had sex but I COULD NOT keep my erection. It was stressing me out. So I pulled out and had her use her hands for a bit. Once I was hard again, I tried fucking her but I could feel that I was losing it again so I pretended to come. We then went to sleep and I woke up with a hangover.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used a condom and she was on the pill.

What were your REASONS for having this hookup? Recently gotten out of a long term relationship which involved no sex.

Were alcohol or drugs involved? If so, how much? Alcohol. We both were a tad drunk.

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 had no desire to be in a relationship so we just continued to see each other on weekends and fuck. We ended it amicably and are still friends. She’s a great girl and I enjoy hanging out with her, however I have no real desire to pursue her.

To whom did you talk about the hookup? How did they react? Casually mentioned it to my friends. It wasn’t a big deal at all.

Was this a consensual and/or wanted experience for you? For your partner? It was consensual.  We both got what we wanted during our time together.

Do you regret this hookup? If so, why? Not at all.

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 is that I ended my 2 year dry spell. The worst I suppose is that It was the first time I had ever had an issue in that department.

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

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

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