A Beautiful Encounter in a Seedy Place

This post is sponsored by Trust Massage Oil.


What’s your gender? Genderqueer / Nonbinary
How old are you? 34
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Amsterdam
Highest education received: Some college (not currently in college)
What’s your occupation? Software
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Bigender Bisexual
How many sexual partners have you had in your life (including oral sex)? Hopefully still in the triple digits
How many hookup stories have you here posted before? None

A beautiful encounter in a seedy place

How long ago did this hookup happen? Half a year

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

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

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? She was a beautiful trans woman with some middle-eastern blood in her. She had beautiful hips that were just properly feminine and breasts that were still small but beautifully perky.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had been cruising around the local sex cinema and had sucked some cock already but nothing really special yet and I was looking around for some more satisfaction. Then I walked up to the darkroom area and as I made my first circle she walked past and my eyes immediately locked on to her… and she looked back

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 connected by looking at each other and in a hushed voice, and we  chatted very briefly when I pulled her around the corner onto the bed which was open for everyone to see. We started to touch each other’s cocks while almost hugging with a deep sense of intimacy. After a bit of playing with each other’s cocks, I went down on her and gave her a nice deep throat sucking. Then when I came up she turned around and sucked me for a bit and then I undressed her top and guided her to lie on the bed. I kept sucking her there and climbed in top where we were riding and kissing and sucking while a small crowd had gathered behind us to watch. At some point I tried to figure out it she wanted to fuck or be fucked — but it wasn’t clear, so I ended up putting a condom on her and moved her cock to my ass. She moved a bit, but soon after she came inside of me, she started feeling uncomfortable and said she wanted to stop. So we wrapped up.

I was sad that the connection broke but accepted it and we went our separate ways walking around for a while more.

Then eventually I came down to the straight cinema floor where she was sitting alone on a couch. I immediately looked at her again and to my surprise she looked back and we locked eyes once again. I carefully and cautiously sat next to her and we started touching each other’s cocks again, and quickly started kissing passionately. We kept kissing with a closeness that you rarely feel, and eventually she moved her ass towards my cock and I slowly started fucking her from behind while kissing her in a tight embrace.

She was incredibly tight and while I just managed to get my tip in she was moaning in an obvious mix of pleasure and pain so I fucked her gently and made sure I came fairly quickly inside of her. To my surprise, she was disappointed when I pulled out. So I worked her ass back onto my cock and started fucking her again with just the tip of my cock. I slowly fucked her for what felt like ages until I came inside her a second time, after which I pulled out again and we embraced and kissed more for a bit. To my surprise she still wanted more and once again worked my not fully hard cock up her ass where it quickly became hard again, and we fucked one last time until I came and told her that was really enough for me. We kept cuddling and kissing on the couch for a bit longer until eventually we both got dressed, left and went our separate ways.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? I don’t know

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? Good. I enjoyed it very much and still look back on it fondly now and then.

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, Attraction to partner(s), Emotional intimacy, closeness, connection

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? I didn’t discuss it with anybody in particular.

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? How beautifully trans she was and being able to come again and again as she wanted more.

What was the WORST thing about this hookup? That we didn’t meet again after.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not particularly.

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? I think we should have more of it. I wish it could be a normal activity amongst friends.

What do you think about the Casual Sex Project? Great initiative!

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