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What’s your gender? Man
How old are you? 57
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
Any other term(s) that describe your sexuality or sexual identity? I lean a bit towards women but also enjoy men
How many sexual partners have you had in your life (including oral sex)? 70
How many hookup stories have you here posted before? 7

Threeway with a Cross-Dresser

How long ago did this hookup happen? Last month

What was your relationship status at the time? Same as current status

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? All male threeway. Second guy is married and is my fuck buddy, attractive, very normal middle aged dude. Third guy is a cross-dresser (CD), very feminine (also married).

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? CD and I had played once before, about a year ago. He contacted me about arranging a threeway.

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? Started by me giving my bud oral while he gave the CD oral. Then we did a threeway oral daisy chain. After that, the two of them 69’ed while I fucked my bud (anal). Then they both sucked my cock and balls while the CD fingered my ass. The CD then started kissing me while my bud sucked me and I came really hard. My bud came by being stroked off by the CD. The CD did not cum as he had a difficult time getting hard.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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 bud had to go back to work, the CD stayed and we chatted for a while. A few days later, we all agreed, via emails, that it was a very hot time.

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, Thought it was an important experience to have

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? Hot threeway sex

What was the WORST thing about this hookup? Difficult to arrange the logistics

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Makes me want to do more threeways

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

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

Anything else you want to add about this hookup? Not the first time I’ve played with CDs or done threeways with another guy and a CD. But it had been a while and it was a lot of fun.

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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