My First Paid Encounter

by Eugene

What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Iowa
Highest education received: High school diploma
What’s your occupation? Maintenance management
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? +/-15 and counting
How many hookup stories have you here posted before? 4

My first paid encounter

How long ago did this hookup happen? 5 years ago

What was your relationship status at the time? Engaged/Married (monogamous)

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 met her on a site that is known for a place to get with escorts. I didn’t have much of an opinion before meeting. I had seen her pics in the ad but no way of knowing if they were actually her, how old they were, etc. They also did not show a face. We agreed on some basic terms and met at her house.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I arrived at her house, received some basic instructions and general chitchat. She led me to her room and we both began to undress.

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? The encounter itself was very different because this was my first of this nature. She was very friendly and assured me of her cleanliness/carefulness. However, there was no real warm up time. She had me lay on my back and she placed a condom on me. She made a quick remark on my size (by this time I’ve already heard “you’re kinda big” enough times to realize there’s likely some truth to it. She sucked me for a little bit and then said she didn’t think she needed to do that anymore as I seemed ready (I get very hard). She asked me how I wanted her. I told her I was her guest so it was up to her. She told me doggy was her “fave” and she got on all fours. She had already made it clear that I wasn’t allowed to put my fingers in her so, I worked my cock inside. She felt pretty good so, I continued to push deeper while rocking in her. Once I was in her a little ways, I bent over her to grab her tits. I pushed deeper yet and she made a comment about the depth. I asked if I was hurting her and she said it was okay. She made noises as to enjoyment but I was curious as there authenticity. After a bit, I came. She helped me clean up, told me how I was a little cutie and discussed some other future options. I left with mixed feelings.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, 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? It was a little embarrassing. I had never paid for it before. It wasn’t enjoyable enough to go back.

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, To cheer myself up

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? I don’t know / I’m not sure

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? A little bit

Why do you regret this hookup? It was my first foray into escorts.

What was the BEST thing about this hookup? I had sex with a decent looking girl.

What was the WORST thing about this hookup? It wasn’t gratifying.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I like girls who I know want it.

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? Fairly negative

Anything else you want to add about this hookup? No.

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? Paid sex is nice in that everyone knows there’s no move toward a relationship.

What do you think about the Casual Sex Project? Good place to vent.

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