Pleasant Working Girl Experience

by Colin

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? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Lawyer
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 2

Pleasant Working Girl Experience

How long ago did this hookup happen? 9 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? S was beautiful. I was living in an Asian country, single and sexually frustrated. I initially never considered paying for sex, always thinking it was immoral. But being around so much of it (every street corner had a massage parlor) I began thinking about before finally giving in. The first two times it didn’t go well. But the third time was the charm. S was beautiful and sweet. She lightly knocked on my door. I let her in and we chatted briefly. I offered her a glass of water which she took. I felt a little awkward, but finally took out the cash and laid it on the table. She smiled and we went into my bedroom.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? In the bedroom, we continued chatting. Her English was decent, and I had learned a smattering of her language. We kept chatting until finally our bodies got closer and closer before making contact. We were sitting on the edge of my bed. She started rubbing my crotch getting me hard, so finally I stood and dropped my pants.

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? S was still seated. With my erect cock at eye level, she opened her mouth and began blowing me. I just closed my eyes. It felt amazing. I’d look down and watch her beautiful face as she blew me, then close my eyes again. This went on for a few minutes. Finally she stopped and stripped. With both of us naked, she put a condom on me. Then she laid back on the bed and said, “fuck me.” First we went in missionary. Then I had her get on ride me. Watching her bob up and down on me was amazing. She was and is the hottest lady I’ve ever had sex with. After that, she went into doggie. At this point I was close to orgasm. I stopped and pulled the condom off. My plan was to have her stroke me to orgasm and cum on her breasts or stomach. Instead, while I was still up on my knees for doggie, she turned around and took me in her mouth again. I was close and I said, “I’m gonna cum” thinking she’d finish me by hand. She kept going like a champ and I came hard in her mouth. I remember vividly the feeling of her wet tongue on my cock as I squirted again and again. So hot. I collapsed. She went to the bathroom and spat it out. We rested and she blew me again, and though it was lighter I came again.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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 paid, she left. I called her several more times over the next year. She was too hot and too good at that not to. To this day I masturbate thinking of her sometimes. She’d always let me cum in her mouth. We actually got to know each other, and finally one day she let me run her clit and finger her to orgasm. She might have faked it, but I think it was real. I’m not saying we had a deep emotional connection. But we had developed a comfort level and familiarity sufficient that she finally decided to get off.

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, I was feeling lonely, 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? 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. This is the first I’ve spoken of it.

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? Somewhat

Why do you regret this hookup? I paid. It would never have happened otherwise. So my economic position and her economic position allowed me to use her body for my gratification. I think it was wrong, although it was sexually gratifying and I still get aroused by the memory.

What was the BEST thing about this hookup? If she was resentful of me she never let on. She shared crazy stories with me of other clients, stuff like banging a client while his wife unknowingly sat in the next room thinking S was a language tutor. Stuff like that. I liked her and hope is on to better things.

What was the WORST thing about this hookup? Paid sex.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Oddly, it made we realize prostitutes are people not objects. Society either objectifies them as cum dumps or ostracizes them. They’re just people with a story. People are complicated beyond their profession, even this one.

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

All things considered, how NEGATIVE was this experience? A little 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? Sometimes people just need to get off. If all parties understand this, I think it can work.

What do you think about the Casual Sex Project? Its fun. I’m glad to have a way to share my stories.

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