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? One

A New Low


How long ago did this hookup happen? A Year

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? Dee was a short, petite little blonde in her early twenties.  We crossed paths at a party in my neighborhood.  I did know her before this but didn’t realize it, I hadn’t seen her in years.  I thought she was cute and was attracted to her even if she was a few years younger than I usually go for these days

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I went to a party in my neighborhood, ate dinner, and chatted up a few women.  I was going though a bit of a dry spell at the time and struck out.  I bumped into Dee at the cooler and we started chatting and flirted just a little bit.
Dee came with me back to my place to grab a few things with me.  We brushed up against each other and ended up kissing.

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? Both of us were a little surprised Dee went with it after but I ended up turning her over and bending Dee over a table.  I ended up fucking her from behind doggie style until I came about five minutes later.  I was a little embarrassed that I came so fast but Dee was pretty sweet about it and said she had liked how I took control.
We went back to the party for a bit, and when it broke up Dee came back to my place and we went in my bedroom.  She was pretty eager and stripped naked and I saw she had a bit bigger of a rack than I had thought.  I grabbed her breasts and we made out naked for a bit and she then asked me to lay back.  Dee mounted me and rode me cowgirl style.  She got quite loud and sweaty and really started moaning and had an orgasm and I did shortly after.  Afterwards she fell asleep next to me.  Next morning I woke up and she was gone.

Did you have an orgasm? Did your partner(s)? I did twice and Dee did the once

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I used a condom both times

What were your REASONS for having this hookup? It was pretty simple, I was horny

Were alcohol or drugs involved? If so, how much? I had one beer and I think Dee had a Mike’s Hard Lemonade, not much each

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 hooked up with Dee a bunch more times over the next month or so.  We didn’t talk much, mostly just had sex. I liked her but was unsure about perusing a relationship with a woman, a girl really, the same age as my own daughter.  However Dee was the first person I even considered a relationship with after my last divorce.
Now this is where it gets really bad.  Dee was at my place one morning and took  a phone call, and I heard her last name and it finally clicked.  She was a close friend of mine’s daughter, I hadn’t realized because Dee’s parents had split about six years before when Dee was fourteen and she had moved away with the Mom and Dee had taken her Mom’s maiden name.  She was in town spending the summer with her Dad.  She hadn’t told me and we had a huge argument and she kept saying her Dad had nothing to do with us.  We had angry sex and she then left my place.  Now I have fucked friend’s ex’s, girlfriends, even a few wives but even for me this was a new low.  I made the decision that it was best to not see her anymore.

To whom did you talk about the hookup? How did they react? Told my business partner who despite her own sexual history was quite judgmental.

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? Unlike most of my hookups, quite a bit.   I feel like I really crossed a line, and things have been quite awkward between me and my friend Tony and I haven’t told him why.

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? I really did enjoy the sex with Dee.  Worst part was that she was a friend’s daughter and the aftermath.  I don’t think this has changed how I feel about casual sex or sexuality but I did learn even I have lines when it comes to sex.

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

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

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