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? None


Some Cliches Are True


How long ago did this hookup happen? A Month

How would you best classify this hookup? Booty Call

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? Gwen has been one of my clients for years, she has long black hair and is pretty fit and a nice chest and ass.  She is also in her late thirties.  She came into my gym a few years back and hired me to help her get in shape.  Gwen is married, but honestly I had been fucking her for years.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Since this is my first post I will share a bit of my background.  I have been sexually active since I was 14 and have had a lot of partners.  I have been married three times and divorced for a few years, but haven’t really dated anyone since my last marriage ended.  
As a personal trainer I have always done quite well with women.  Many of my clients are like Gwen, bored lonely housewives which are my bread and butter in both business and the bedroom.  Gwen was looking to get in shape after two kids who were now older and was trying to get the attention of a husband who spent most of his time at work and wasn’t noticing how good of shape she was now in.  We didn’t hookup right away but as I said I had been fucking her for years.
Most of the time it was after a workout that Gwen and I would hook up.  This was no exception as she asked me to join her in the shower.

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? In the shower we made out and felt each other up and she played with my cock a bit but there was no intercourse.  We moved to her bed where she gave me oral, not something she normally did and I got quite hard.  I penetrated her and rode her and we both orgasmed in near unison.  We cuddled for a few minutes and Gwen then kissed me and asked me to leave.

Did you have an orgasm? Did your partner(s)? We both did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I did finish inside her and we seldom use condoms but Gwen is on birth control

What were your REASONS for having this hookup? Mostly because I could and Gwen was willing

Were alcohol or drugs involved? If so, how much? Nope

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? Gwen and I have hooked up a few times since as is our regular pattern.  I don’t see it ever turning into a relationship of any kind as for one I am not really interested in that and I don’t think Gwen will ever be willing to leave her husband.  For now, I will just enjoy the sex with her when I can get it.

To whom did you talk about the hookup? How did they react? As Gwen is married I have never really told anyone but my business partner did find out and she has said that my fucking a married woman is not a good idea.

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

Do you regret this hookup? If so, why? Nope

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? Good sex on a regular basis, not sure there was really a bad part.  This hookup is a normal thing for me so it has not changed how I feel about casual sex, sexuality or anything else.

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? My business partner turned me onto this website, thought with my sexual history I would make a good addition.

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