by Lenny


Gender: Male
Age: 44
Race/ethnicity: Mixed
Current location: Columbus, OH
Highest education received: College degree (eg., BA, BS)
Occupation: Personal Trainer/Own a Gym
Relationship status: Single
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 100+
How many hookup stories have you here posted before? Seven

Workplace Fun

How long ago did this hookup happen? Six Months

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…)? Sex with an Employee/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? Tia was a fit, muscular woman with long brown hair and in her early thirties.  I had hired her to work for me about a year before we hooked up.  I knew her pretty well and liked her and thought she was attractive and even had flirted with her a bit but did not consider Tia a potential partner.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A little background here.  Around the same time as my third divorce I achieved my dream of finally owning my own gym.  I had worked as a personal trainer for years but had never achieved it.
Business took about a year to really get doing but when it did it took off.  I hired several trainers to keep up with business, and Tia was one of several women who applied.  I interviewed her and learned a lot about her, she was from mixed heritage like me with a White mother and Cuban father (Mexican mother and White father in my case).  She had also been a personal trainer for years, and also could teach yoga.  Also very attractive, Tia was exactly what I was looking for and I can’t pretend like her looks weren’t a big part of the reason I hired her.  Attractive female trainers lure in the male clientele.
As I shared in my previous posts following my third divorce I wasn’t looking for any sort of relationship.  I had a few hookups, as I do really enjoy sex, but nothing too serious.  Tia was always around, friendly and even a little flirty at times.  She worked for me for about a year when we hooked up.
We were working out together one day and there had been a lot of touching and brushing up against each other during the workout, there was a lot of sexual energy in the air.  Tia pulled me into a kiss and it went on 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 went to my office for privacy, even though it was early in the morning we could have been disturbed.  Her sports bra came off and we ended up making out on a couch for a bit.  I grabbed her breasts, and then pulled her pants down and penetrated her.  I rode her for a while, it took me a little longer than usual to finish but I did dump a load inside her.  Wasn’t really any talking and it was mostly just a simple, quick hookup.  Afterwards Tia pulled her clothes on and left my office quickly, I think she was a little embarrassed.  I would later learn it had been over a year since she had been with anyone and she was not usually one to just hook up with a guy.

Did you have an orgasm? Did your partner(s)? I did and Tia did not.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None which was a little foolish but I didn’t get an STI and Tia didn’t get pregnant.

What were your REASONS for having this hookup? I would say there was a little lust involved but mostly because I just wanted to.

Were alcohol or drugs involved? If so, how much? No

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? The next three weeks were quite intense as Tia and I had sex almost every night and even quite a bit during the day.  Two or three times a day every day, it was a bit much even for me.  We toned it down a bit after that, and Tia was a regular hookup for a few months after that.  About three months after we hooked up she came to me in my office and said she had started developing feelings for me and would have liked a relationship but didn’t think I was capable of monogamy.  Tia ended it and also gave notice at the gym a few days later.  She no longer works for me, and last I heard she was working at another gym on the far side of town.

To whom did you talk about the hookup? How did they react? Told my business partner who was less than thrilled, and I think also think she was a little jealous, she also liked Tia and found her attractive.

Was this a consensual and/or wanted experience for you? For your partner? Yes and Yes

Do you regret this hookup? If so, why? A little bit, because Tia was one of the best trainers who has ever worked for me and some of her clients moved on with her.

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? Some good sex, worst part has been that I am not sure about her accusation about my being incapable of monogamy.  Not sure this has changed how I think about casual sex and sexuality, but I don’t think I will be going anywhere near my staff again.

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

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

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