Boss

by Lynn

What’s your gender? Woman
How old are you? 32
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Attorney
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your 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? 1

boss

How long ago did this hookup happen? 10 years

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than 6 months

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? Mid-thirties, short, dorky-looking, receding hairline, wore khakis and polos a lot.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He was my boss (or boss’s boss), the owner of a flower shop I used to deliver flowers for. Most of my co-workers, including him, drank a lot and partied outside of work, and I joined once or twice. Once I met him out with a friend of his and had dinner and got drunk. The 3 of us went back to his house and continued to drink. I got the impression his friend was sticking around in the hopes that I would fuck him instead of my boss, or that we would have a threesome, or he could watch or something. But when we didn’t invite him to do any of those, he eventually went home. Then my boss and I went in his bedroom and had sex.

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? The sex was a little rough but kind of fun, we did missionary for a bit, then I was on top; we also 69’ed. I was pretty drunk and it happened a long time ago so I don’t remember a whole lot.

How sexually satisfying was this hookup? A little

Did you have an orgasm? No, not even close

Did your partner have an orgasm? I don’t know

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I was so embarrassed. He’s not even attractive, and he was my boss. I had to see him at work. I was afraid others would find out because everyone there gossiped. He texted and called me later the next day wanting to hang out again, but I told him right then and there that I didn’t want to let this go any further. He was disappointed but accepted it. I quit a month or 2 later I think.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Intoxication, To feel better about myself, To feel more desirable, To feel more confident, I was feeling lonely, Making new friends, Everyone else was/is doing it, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Completely wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Completely wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? my closest friends. they thought it was funny.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? Very much

Why do you regret this hookup? People at work found out and occasionally made jokes; he was not that cute and kind of a douche. Really lame.

What was the BEST thing about this hookup? It was kind of liberating to be having casual sex, and I felt powerful being able to so easily attract older men and make them want to fuck me.

What was the WORST thing about this hookup? It was my boss, and he was kind of a lame dude. And I was really drunk.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It showed me that I’m stupid.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

You have a hookup story to share? Submit it here!