by Vallin

Gender: Male-ish
Age: 53
Race/ethnicity: Carthaginian/Cherokee
Current location: Atlanta, GA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Singer-Bass Guitarist
Relationship status: Single
Religious affiliation: Luciferian-Narcissist
How religious are you? Very
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Polysexual-Transamorous
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? None


How long ago did this hookup happen? 10 years ago

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-morning 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? Met a tall CD/TG, cute but non-passable on AdultFriendFinder. She was a doctor from West Hollywood (how proud my Mom would be!) visiting NYC where I lived then. She was very “Fredericks” in a classy-slutty way: corset under a sheer nightie, bulging peach-colored panties, BIG hair (looked more like a femmy Brian May…which is cool as I adore and resemble Freddie Mercury, darling).

She contacted me online (I was doing net-cafes then), and we talked on the phone. Her fake-girl sissy voice was actually very sexy to me. We discussed what we might do with each other, then she told me her location. We agreed to meet up the next morning. I was hot as hell for this as I’d just gotten into transgender(s) in the previous year.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met on AdultFriendFinder. What was interesting is that I only had head-shoulder ID shots online then (no home cam). I had described myself physically, including my 10″ penis.

We made some typical date planning; very short notice. I had to call her from a pay phone a few times as I ran a bit late.

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? She met me at the door and led me in. I LOVED her long legs and skinny, swishy ass in her tight peach panties. I came around and sat on the bed. I immediately got her panties off and gave my first head–I loved it. With my other cis-GG partner (ex-wife) I dived on her first, too. Samantha (the trans here) had just showered and smelled so clean. I DO appreciate that!

She was obviously experienced, a Queen of Spades who loves big black dick. I ass-fucked her deep and she popped my tender ass cherry, too. THAT was some GOOD to ME! She never came inside me 🙁 (I would have wel-cummed it). Eventually I jerked myself to orgasm beside the bed as she lay there.

I kissed her on the way out.

Did you have an orgasm? Did your partner(s)? I did.
I wished she’d had. Especially inside me!

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We both brought fresh condoms (that’s why I was late) That was especially good as I like to grind deep–and I’m 10″–so I got covered in poo. “Occupational” hazard.

What were your REASONS for having this hookup? Curiosity…and steep membership fee on AFF! I love transwomen even more from the experience.

Were alcohol or drugs involved? If so, how much? No. The experience sober was more than exciting enough.

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 weird looking at the giggly HS girls on the bus ride home. They weren’t so appealing anymore, just puerile. I had “graduated” to a new level of sexuality.

To whom did you talk about the hookup? How did they react? No-one. I wrote to Samantha a few times just to say how much I enjoyed it. I’ve written this on a few surveys. Eventually I told my ex-wife after I’d moved to Atlanta. She’s never spoken to me again.

Was this a consensual and/or wanted experience for you? For your partner? YES-S-S-S…Oh GOD, YES!

Do you regret this hookup? If so, why? I only regret I haven’t had more of them. Despite spending hundreds of dollars at the Southern Comfort Conference.

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? Sex with a “tranny” (gotta’ say it). And great casual sex. I never had any in the 70’s–nor a girlfriend for that matter [‘snif’].

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

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

Anything else you want to add about this hookup or anything else? When can I hook up again, dammit?!!

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