Sex with My Supervisor

by Author

What’s your gender? Woman
How old are you? 21
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Some college (currently in college)
What’s your current relationship status? Single
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? 0

Sex with My Supervisor

How long ago did this hookup happen? A month ago

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

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? He was my supervisor at work. He had nice muscles and some visible tattoos, I was very attracted to him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I would flirt with him at work and he would flirt back. There was so much sexual tension between us. Eventually, we ran into each other at a bar and I asked him to get food with me afterward. We began flirting more heavily after this and hung out a few times but nothing happened. Eventually, I left for a winter vacation and we started sexting. When I got back from my vacation I invited him over and we had passionate sex until the sun rose the next morning.

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? He ate me out, I blew him, and we did just about every position imaginable. It was rough and wild and there was a lot of dirty talk. He ended up leaving a huge bruise on my neck, which was a little awkward since I had to work with him the next day. It was a lot of fun and felt so good. Afterward, he cuddled with me and we talked all night until I got horny again and blew him.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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? We hooked up a few more times afterward, but eventually, it fell apart because we worked together and he would get in trouble because he was my supervisor. When we were together, it was great and so much fun. It kind of sucks now because we still work together and it’s a little awkward navigating how to treat/talk to each other. I would say it was worth it, and we have no hard feelings. It’s just hard because we both are still interested in each other and kind of get jealous when we see flirtation.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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

Did you consent to this hookup at the time? I gave enthusiastic consent

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 friends. They were supportive. Although they did try to protect me from getting hurt because the situation did not seem like it would end well.

How would you best summarize people’s reactions about this hookup? Relatively positive

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Honestly, it was amazing. I went out of my comfort zone and explored my sexual identity and interests, which was empowering. It was very satisfying because I was attracted to him and could turn him on. It was also kind of hot because it was a ‘forbidden love,’ as he was my boss.

What was the WORST thing about this hookup? The worst thing was ending it and still having to work with him. If you work in a place where you have to see your hookup every day, I wouldn’t recommend doing it because it is not a good feeling. Plus when we go to work functions now, I have to see him flirt with other people.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, I think it has taught me how to be more open with myself and my body. I am more curious about casual sex and the benefits of it now (however, I have learned the hard way that you should not have sex with someone you work with unless you REALLY think it’s worth it).

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

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

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I think it’s beneficial but also scary. I’m in college, so casual sex is fairly common. However, I feel bad for people looking for something more serious. I feel like it is impossible to find someone who is interested in anything other than casual sex on a college campus. For me, it has given me confidence and helped me understand and define who I am and what I like.

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