The Best I’ve Ever Had



What’s your gender? Trans man
How old are you? 28
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Long Island
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Insurance
What’s your current relationship status? Dating casually
Religious affiliation: Spiritual
How religious are you? Somewhat
What’s your sexual orientation? Mostly 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)? 10
How many hookup stories have you here posted before? 0

The Best I’ve Ever Had

How long ago did this hookup happen? 7 months ago

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For less than 6 months

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 is a short guy, about 5’5″, with a mop of black hair and a well kept beard. He’s very slim, but not a twink. At the point of this story, we had become quite good friends, benefits included. We had met about 3 months prior and had been hooking up. We met on the app Scruff.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was New Year’s Day and he came over to my house to watch the hockey game with me. I’m a huge fan of the sport and he was just coming to keep me company. During the first intermission, he kissed me and we started making out. He slipped his hands beneath my shirt and it was on.

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? It was honestly the best sex I’d had to that point in my life. He started out by rubbing the head of his dick on my dick while we made out (I’m a trans guy, so when I say my dick, I mean the clitoris.) It drives me crazy. He reached down to guide his dick into me and started out really slow (no condom). He’s about 8in, so he is really gentle at first so that it doesn’t hurt which I truly appreciate! Once we got into a rhythm, he started going harder. We did it in every position we could think of. He made me feel so sexy and wanted. He is a fantastic lover. He made sure I got off multiple times before he was ready to blow his orgasm. I sucked his dick while he laid back on the bed and he got close. We took videos of me sucking his balls while he shot his load.

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? Afterwards, we cuddled and watched the rest of the hockey game then went and grabbed something to eat because we were both starving. At the time, I had hoped that we would end up together and was hurt when, later on, he told me he didn’t feel that way about me. I’ve since moved on emotionally and met someone, but I’m still best friends with this person and we still do hook up occasionally (both of our partners know that we do it).

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more

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 told a few close friends with whom regularly chat about sex and stuff. They were happy for me.

How would you best summarize people’s reactions about this hookup? Relatively positive

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 felt amazing and is very memorable.

What was the WORST thing about this hookup? It had to end sometime! Lol

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? My entire friendship with him has changed my perspective on casual sex and about how it’s okay and nothing to be ashamed of.

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 always thought multiple partners and casual sex or open relationships were a bad thing but over the last year or so I’ve learned so much about what it actually means and that I should be so judgemental. There’s nothing wrong with having a sex friend or with loving someone but still wanting to hook up.

What do you think about the Casual Sex Project? I think it’s awesome.

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