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What’s your gender? Man
How old are you? 58
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Attorney
What’s your current relationship status? In a serious relationship (open)
Religious affiliation: Jewish
How religious are you? Not at all
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 63
How many hookup stories have you here posted before? 4

Tranny Orgy

How long ago did this hookup happen? 2011

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Group sex

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 all of them that day. There were three trannies, me and another guy for a total of five people in this orgy. Everyone was middle-age and white, reaonably attractive.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had sex with two cds before this orgy and was really wanting to attend a tranny orgy. Something about a chick with a dick turns me on. The cd I was fucking at the time told me about a friend (S) who wanted to do a threeway with us. I started emailing with S, who invited me to a tranny orgy in an upscale hotel. Turns out S could not go sue to work so I went alone as I was very curious and horny.

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? I was greeted by the three trannies, who offered me a cocktail. Then another guy (B) arrived. Pretty soon we were all naked. I got sucked by all three trannies and fucked one of them while everyone else watched us fuck. There were mirrors all over their suite and I could watch us fuck. B fucked the other two trannies and I watched. It was very erotic.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

Did your partner have an orgasm? No

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? My girlfriend and I went out to dinner that night and I saw B and his wife at the same restaurant. What a coincidence considering we live in a city of over 6 million people. I laughed inside at the absurdity of the whole thing.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? No one.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? It fulfilled a fantasy I had of attending a tranny orgy.

What was the WORST thing about this hookup? The three trannies were not as hot or young as I had hoped. I did not cum although I was close. There is something about the group sex dynamic makes it more difficult for me to cum.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Makes me want to attend more tranny orgies.

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

All things considered, how NEGATIVE was this experience? Not at all negative

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Love casual sex.

What do you think about the Casual Sex Project? Love it!

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

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