My Second Paid Encounter



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? 5

My Second 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? She was early 30s but very hot. She had just recently turned from stripping to escorting. I found her ad for massage and contacted her to see what all she would do. We talked a little and reached an agreement. I didn’t have nearly as much as she wanted and she said we’d work something out.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met at a motel. She needed my money first to get the room so, that was a little awkward. We went to the room and she changed clothes while I watched. She was a MILF. She had me undress and lay face down on the bed while she rubbed me down and we talked. It was kind of nice, open/honest conversation. I think we were both very comfortable with one another. She had me so excited that I came on the bed while laying down. I didn’t tell her then. After a few minutes, she told me to lay on my back. I told her then that I had cum as I didn’t want to surprise her when she was rubbing my front. She said that was okay so I rolled on over.

I wasn’t sure where things were going to go and I didn’t know what all she was okay with. After a bit, she started rubbing my cock and I was thinking that was all I was getting. Just then she slipped it in her mouth. It was beautiful to watch. She was very pretty and it looked so good filling her mouth. I was totally turned on. I told her she didn’t have to rush and she told me my time was almost up.

Wanting to make sure I came, I asked her if I could play with her breasts while she sucked me off. She seemed both surprised and glad to let me. I could tell as I began to squeeze and work them hard that she really enjoyed it.

I could feel the orgasm building so I told her I was close to cumming as I didn’t know if she wanted it in her mouth. She kept sucking. I blew what I knew was a large load in her mouth and she took it all and sucked/licked me clean. When I was completely done, she got up, went to the bathroom and spit it out. She came back in and we talked a little as we got dressed.

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? See above, I got a little ahead of myself. After we were done and I was getting ready to leave, she gave me a hug, thanked me and told me that I seemed like a really sweet guy.

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 lost contact with her. I would love to see her again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), 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? 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? Not at all

What was the BEST thing about this hookup? She was hot and fun to be with. It gave me a new hope for escorts.

What was the WORST thing about this hookup? I didn’t get to fuck her. I suspect that had I begun touching her early on that she would have wanted to.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It gave me renewed hope for escorts.

All things considered, how POSITIVE was this experience? Very 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? There’s less emotional expectations with escorts.

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

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