by SkoolBoi

Gender: Male
Age: 46
Race/ethnicity: Afr. Am.
Current location: Austin, TX
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Photography
Relationship status: Married
Religious affiliation: Catholic
How religious are you? A little
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Trans Friendly
How many sexual partners have you had in your life (including oral sex)? 22
How many hookup stories have you here posted before? 0

First T-Girl

How long ago did this hookup happen? 1 yr

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? This was an acquaintance I knew from the local bar scene.  We had only danced and flirted before. I thought she was pretty wild (wilder than me). I liked her both before and after.  We remained acquaintances but never hooked up again.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She was flirting with me at the club.  I had a hotel room.  As closing time approached she got more friendly.  I mentioned the hotel and she said lets go. (I had the room to do some secluded writing).

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 got to the room.  I gave her a drink and went to the bathroom.  When I came out she was topless wearing only a thong.  We kissed.  I sucked on her breasts.  Then when I removed her thong I sucked her cock (she was an MTF transsexual).  I put on a condom and she returned the favor.  I tried to perform anal on her but wasn’t firm enough.  After more kissing and mutual stroking she removed the condom and I hard enough to enter her.

Did you have an orgasm? Did your partner(s)? I did, she didn’t.  I pulled out and came on her stomach.  I got up and got two towels (one wet and one dry).  After we cleaned up we held each other and talked a while.  I finally drove her home.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Started with condoms but abandoned them.

What were your REASONS for having this hookup? Just two friends having a a good time.

Were alcohol or drugs involved? If so, how much? A little but neither of us was intoxicated.

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 felt ok.  A little bad about the condom.  I have an open marriage but condoms were a requirement. She is still a friend but we haven’t hooked up again.

To whom did you talk about the hookup? How did they react? I only told one friend.

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

Do you regret this hookup? If so, why? Just the unsafe play (we’ve both been tested since).

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? It was my first penetrative sex with a trans woman.  I was not confused with other relationship issues.  It was just two friends enjoying each other.

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

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

You have a hookup story to share? Submit it here!