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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? 6

New to Escorting

How long ago did this hookup happen? 4 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? She was a late 20s girl with some financial issues to deal with. She was not the hottest girl ever but, she was alright. I was browsing CL at work, found her ad and we emailed back and forth a little. She sent some pics and we agreed to meet after I got off work.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I went to her house. It was kinda messy. She had a kid or two sleeping downstairs and we quietly slipped up to her room. That was a little awkward for me but, nothing I hadn’t seen before.

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? Once we got to the room, we laid in her bed and talked a little. I could tell she was nervous but that she was also genuinely interested in me. I still wasn’t sure what she was expecting so I asked what I could do. She said anything. So, we began by kissing. It became clear to me as things progressed that she didn’t have much experience with guys who wanted her to enjoy herself as well. Once she realized that I was interested in her pleasure as well as my own, she confided that she was fairly inexperienced but that she wanted to learn.

Over the course of the encounter, we tried many different positions and techniques. She was a little clumsy but very into it. She came several times. I ended up coming earlier than what I would have preferred as she was willing to go as long as I wanted. I was very tired from working all day, however and decided it was time to go. I got the money out to give her and initially she refused to take it saying she felt she owed me. I insisted as I had previously agreed to it plus, I did feel for her situation. She told me to come see her again. I told her I didn’t have any more money and she said she didn’t care, she just wanted more sex like that.

I kept her number and she agreed to meet up again, telling me she would do anything I wanted. I was never able to make it work on my end and lost her number.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

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 enjoyed her. I think I could have enjoyed a long period of booty calls. I wish I could see her again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Boredom

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? 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? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? By this time, hooking up had become easy for me. The idea of paying for sex was becoming less repulsive to me as well.

What was the BEST thing about this hookup? Teaching a lover to become a better lover.

What was the WORST thing about this hookup? Not seeing her again.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No.

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

All things considered, how NEGATIVE was this experience? A little 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? I still wish I didn’t enjoy screwing around like I do.

What do you think about the Casual Sex Project? Good forum.

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