by Leslie

Gender: Female
Age: 45
Race/ethnicity: White
Location: Dallas
Highest education received: College degree (eg., BA, BS)
Occupation: Sales/marketing
Relationship status: Married
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Bicurious
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 0

Hookup With The Boss

How long ago did this hookup happen? Four weeks

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…)? One night stand

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 started working for our firm about six months ago. I knew him from a business perspective for about five years prior to him coming to our firm. I always thought he was very attractive but I am married and he is as well.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? There was very little planning involved. Several of us went out to watch a basketball game at a local bar and it dwindled down to just me and him. We both had several drinks and it was mutually decided that we would go back to the office down the street.

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? He was a great lover, a fantastic kisser. He shoved me up against the wall then we came into the office and pinned me up against the door and started kissing me. I ended up on his desk with my skirt up to my hips and my legs wrapped around him while he was standing. I was able to come with him inside me and no other stimulation. It lasted at least 30-40 minutes before he finally came and we stood there kissing another ten minutes while he told me how fantastic I was and how great my breasts and ass were over and over again. We didn’t talk much about it that night but he called me on my way home to tell me he left his wallet on the desk.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Nothing, though we did establish I had an IUD and that he’s only had one other partner in 14 years and my history was similar.

What were your REASONS for having this hookup? Mutual attraction…alcohol…lowered inhibitions. I felt like he had been getting closer to me over the course of the few weeks prior to the hookup–lingering touches, in my personal space, etc.

Were alcohol or drugs involved? If so, how much? Yes we both had several drinks prior.

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 feel great. I was a bit worried about feeling awkward because we work one on one quite a bit and have to travel together at times, but it wasn’t that way. He made a joke about it the next day to break the ice and then we talked a little while later and he apologized. Said he hoped he wasn’t taking advantage. I told him I was a grown up and I wanted it as much as he did so not to feel bad. I wouldn’t mind if it happened again. The opportunity is there. But he felt guilty about his wife so it probably won’t.

To whom did you talk about the hookup? How did they react? Only a close friend who has had a similar situation. She’s met him and thinks he’s very hot and wanted to know all about it. None of my coworkers know and you would not be able to tell by our behavior towards each other at work, ever.

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

Do you regret this hookup? If so, why? I don’t regret it at all.  It was fun and sexy and fabulous sex.  I’m sure having sex with your boss isn’t the greatest idea but we still have a mutual respect for each other and we work well together.

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? Best thing was the sex!  Worst was that it probably wasn’t a great idea to have sex in his office.

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

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

Anything else you want to add about this hookup or anything else? I’ve only had sex outside my marriage once in 20 years so this was not the norm for me or for him.

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