Professor Craigslist

by Tearoom Trade

What’s your gender? Trans man
How old are you? 36
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? North America
What country and/or city do you live in? New York, NY
Highest education received: High school diploma
What’s your occupation? Rather not say
What’s your current relationship status? In a serious relationship (open)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Gay/lesbian
Any other term(s) that describe your sexuality or sexual identity? Queer
How many sexual partners have you had in your life (including oral sex)? So fucking many
How many hookup stories have you here posted before? None

Professor Craigslist

How long ago did this hookup happen? 2 days ago

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

How would you best classify this hookup? Craigslist

How long did you know the person before this hookup? For more than 3 years

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? He looked like a typical 56-yo (I think he’s actually in his 60s). I had actually hooked up with him as a sex worker 5 or 6 years earlier. I was housesitting for friends and posted an ad on Craigslist-was feeling super slutty. He was vaguely familiar, and when he opened the door, I immediately knew it was him on account of his TERRIBLE stereotypical British teeth. His response to ad was straightforward and informed (he’s fond of FTM trans men).

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I posted the ad, I knew he was going to be a good lay, I knew he was hung. He walked in, made easy small talk and I told him that we had fucked before years ago. He started to undress and had a nice big bulge. I went for it straight away.

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 blew him, he went down on me and jerked me off. I came once and begged him to fuck me. He was handsy and very verbal, very into it. We got into some daddy/boy roleplay, dude is very kinky.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? Totally hooked on his dick even though he’s a dirty old man who’s also kinda creepy-looking. He’s gonna be my go-to kinky hookup now for sure, planning on seeing him tomorrow.

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, Intoxication, To feel more desirable, To feel more confident, Submission / Relinquishing power

How intoxicated were you? A little tipsy/high

What substances did you consume? Marijuana, hashish, Poppers (Amyl Nitrate)

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Marijuana, hashish

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

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

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

To whom did you talk about the hookup? How did they react? I would not share this with anyone.

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I have really been wanting a hot hookup with a hung stranger off CL/Grindr etc, and I just hadn’t found the right kind of top. Finally I found a top that could really dick me down the way I’d been jonesing for. Dirty bird.

What was the WORST thing about this hookup? His teeth.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Don’t think so.

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

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

Anything else you want to add about this hookup? Afterward, he said, “this kind of pleasure can be found for free, meanwhile people are watching television.”

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? I live by it. Sexual liberation, people.
I feel like casual sex is a big part of my queer identity.

What do you think about the Casual Sex Project? Kinda gives me a boner.
I think that it’s great to document how people of ALL backgrounds fuck around.

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