by JJ

Gender: Male
Age: 31
Race/ethnicity: White
Current location: USA
Highest education received: Some college (not currently in college)
Relationship status: Married
Religious affiliation: Yes
How religious are you? Very
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 0


How long ago did this hookup happen? 10 years

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…)? Friends

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? I met her in college, we had one class together, she was 25, had two kids and was married at the time. I could tell she liked me by the way she acted around me. She was a nice gal, but not someone I would have wanted a long term relationship with. I was 20 at the time we met, we didn’t hookup for another year. She was thick and curvy, a little shorter than me… Great legs and stomach, but pretty small chested.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was at her friends house where she was staying after her divorce. We connected again after college through a work connection.

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 were watching a movie in the living room when she came over to me on the couch and laid on top of me. We started making out, her thighs straddling me (wearing short cloth shorts and a t shirt). I grabbed into her thighs and hips as we kissed. I rolled us over onto the floor where we took off our shirts and kept kissing. She asked me if I wanted to stay there or go to the spare bedroom. I told her the bedroom… We got up and walked to the bedroom and continued kissing until she stopped and went into her bedroom to get a condom. 
She came back a minute later and stripped out of her shorts… I took off my pants and got on top of her on the bed. We made out and kissed each other for a while as I rubbed myself on her stomach. I tried opening the condom wrapper with my fingers and couldn’t get it… I had to tear the edge of the wrapper open with my teeth before I could get the condom out and rolled on. 
This was the first time I had ever been this far with a woman and was still a virgin, something that I didn’t share with her. I remember moving my hips down in an attempt to enter her but I couldn’t get it in without her reaching down and guiding me inside her. I remember the feeling of being inside her, she was tight and the pressure she put around my penis was wonderful. She pushed into me and said I felt good… I thrust into her maybe five times before I felt myself starting to cum, which I did. The sex lasted a very short time and was a pretty big disappointment for her.

Did you have an orgasm? Did your partner(s)? I didn’t really orgasm… I came but it wasn’t intense. She didn’t.

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

What were your REASONS for having this hookup? I thought about as she went to get a condom, debating in my head if I wanted to lose my virginity with her like this. I decided I would take what came and reasoned that I would lose it sometime, being 21 I was a late starter.

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? We never did anything else. Things ended a few weeks later and I never saw her again

To whom did you talk about the hookup? How did they react? I shared it with a gal I was talking to online Jodi Heib. She was a friend who read my blog.

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

Do you regret this hookup? If so, why? Yes. I wasn’t ready… Mentally and sexually, it went fast and wasn’t worth losing my virginity to 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? I loved her strong thick legs… Feeling them straddling me… Feeling my dick pushing inside her pussy was a pretty feeling too.

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

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

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