Only Time I Paid



What’s your gender? Man
How old are you? 49
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? Retired (teacher)
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 64
How many hookup stories have you here posted before? 0

Only Time I Paid

How long ago did this hookup happen? About 15 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Paid sex

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?

I only met her once. I think she gave her name as Candy, but this was probably just her street name. She was the one and only person I had ever paid for any kind of sex. I was driving in the late evening along Lake Street in Minneapolis, in a generally poor and black neighborhood. I had been through there many times before, but on this occasion, I passed an apartment at the corner of Lake and 3rd with some low stone walls in front, perfect for sitting on, and a group of 4-5 woman, mostly or all black, were gathered there talking. As the temperature was very pleasant, I had my window down, and while stopping or turning several of them called to me, and one in particular greeted me in a friendly and earnest way. I then immediately concluded what I would otherwise not have–that they were prostitutes soliciting men who passed the corner. I had never done this before, but I was honestly curious and somewhat horny that night, so I took the next turn into a small parking lot for a closed store on the other side of the block. I didn’t remember what words were used but felt I didn’t have any precise expectation of what to do next. Possibly I would turn around and pass them again; I could hardly imagine I would dare to get out and walk to them. I was partially just curious what talking to a prostitute would be like, knowing I could buy some kind of sex even if I didn’t go through with it. But I wasn’t there long before Candy came down the sidewalk and walked up to me, she must have seen me pull in and assumed that I was waiting for her, and took whatever I said or gestured from the car as a sufficient signal that I was interested. Honestly, whatever signal I gave was at best highly ambiguous, but she probably intuited some kind of curiosity from whatever I did, and it paid off. She was perhaps 5’4, fairly thin, late 20s or 30ish (I was mid-30s), not stunning but certainly decent looking. Nor was she or any of the other women dressed particularly like a street walking; Candy would not have looked at all out of place working at a retail store or even a bank.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it?

Candy was friendly, not too aggressive (which would have turned me off), but just enough to make me feel comfortable. She asked me honestly, but very non-judgmentally, what I might be interested in. I wanted to be very safe, so I said I was interested in the most intimate thing that was completely risk-free for me: ejaculating on her face. $20 was suggested and accepted, and I told her the best place to do it was the garage at my house, just a couple miles away. She got in and we drove there. At some point, she asked if it could be $25 since it was taking a little extra time, but this was after we already agreed on $20 for doing it at my place, so I asked if she had changed her mind and wanted me to take her back instead. She said no, and agreed to the original deal.

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 exactly as planned; back at the garage we got out of the car and I turned the inside lights on. I gave her the $20, then asked her to sit on the floor with her back against the bumper while I took out my penis and stroked it in front of her, making it clear that I didn’t want her to touch me. To be honest, there wasn’t much excitement there; it took a little while for me to cum, and it wasn’t much better than just doing it alone. I did ejaculate onto her face, something I had rarely done to a woman as dark as her, so the white cum showed quite a contrast to her skin. She sat stoically through this, and agreed not to wipe it right away so I could take a few pictures. Then she got back in the car, and after letting me look at her cum-stained face a few more seconds wiped it off, and I dropped her back at the same place so she could return to her corner. I never looked for her or saw her again.

How sexually satisfying was this hookup? Not at all

Did you have an orgasm? Yes, one

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? I felt strangely neutral about it all. Taking the pictures and looking at them later didn’t really feel erotic and I didn’t keep them very long afterward. It felt somewhat like wasted money, although maybe it was worth it just to learn that this sort of experience didn’t do anything for me. I don’t feel bad about what I did to Candy. She was looking for money in this way and I’m sure that I offered her one of the safer encounters she was likely to have in that kind of business (I was STI free, but in any case, no semen was on her orifices). Obviously, there was a power dynamic involved, both economic and in some way racial, but I wasn’t trying to humiliate her as a black woman, prostitute, or even simply as a woman; I was simply seeking a sexual thrill. And I didn’t really get it. It seemed just sort of blah, which surprised me. There was nothing wrong with her looks or attitude; indeed, if she had been more enthusiastic or begging for my cum in some porny-fake way that would have turned me off. She just did exactly what I asked: sat and waited patiently for me to cum. And it just wasn’t that fun. I had done this with women I had dated, whom I actually knew better, and it was much more exciting. So I learned that complete stranger sex just wasn’t my thing. If I met Candy again, I’d thank her for this lesson and hope that better life options had come her way.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Learning new things, experimenting, Thought it was an important experience to have, To cheer myself up, I was feeling lonely, Power / Dominance, Boredom, It was easy/convenient

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? Somewhat

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

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

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? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? Because it hardly even felt exciting at the time, let alone in retrospect. Though again, maybe that was important to learn once. The real regret would have been to repeat it in some form, but I knew not to do that.

What was the BEST thing about this hookup? That Candy made it so easy for me; she anticipated my interest and picked up on the right cues or clues, and mildly coached/developed it, and accepted my request, without being aggressive or judgmental.

What was the WORST thing about this hookup? Just that it seemed pointless. I love looking at pictures of women with facials, both strangers and a few women I have done this to. In general, I consider this very sexy and not a demeaning act, but an image of the aftermath of a sexual encounter. Even when a woman takes the cum with an indifferent expression, this can be exciting. But the pictures I had of Candy just left me cold, as if she had had milk or snot on her face. It was so unsexual I saw no point in keeping them.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? That should be pretty clear from what I’d said. I’m not opposed to casual sex and have had it since then, particularly oral sex, including some encounters which also just consisted of ejaculating on a woman’s face. But it must have been the paying for it or the work-like attitude she had for being paid for it, which emptied the excitement out of it; this I’ve never done again.

All things considered, how POSITIVE was this experience? Not at all positive

All things considered, how NEGATIVE was this experience? Somewhat 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? Casual sex has its place; one can learn from it. And not just “not to do it,” but other things about desire, excitement, technique, etc. And it can be enjoyable. The problem is when it occurs repeatedly and the lessons are not learned, and especially when it isn’t truly enjoyable but one seeks it as a kind of obsession, habit, or substitute which is not fulfilling.

What do you think about the Casual Sex Project? Just heard of it and I think it’s a good idea.

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