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What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Houston, TX
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Consultant
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 65
How many hookup stories have you here posted before? 0

She Thought She’d Be My Sugar Baby

How long ago did this hookup happen? 1 day

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? For less than a month

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 this girl on a Sugar Daddy site. She was from a small suburban town nearby and I claimed to be looking for something ongoing. I promised to give her $250 a week, every week, in exchange for weekly dates that involved sex. She said she was 19 and I checked her ID for my own safety. She wasn’t exactly model material, but she was a cute teen girl. She identified as white, but was possibly Hispanic. She was 5’3”, about average build, with a tiny little bit of belly and a larger but firm round ass. We’d texted about a bunch of stuff before meeting, including her sexual preferences, experience, and birth control.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I contacted her on a Sugar Daddy hookup site and she eagerly responded. We texted for a few weeks about sex and other stuff. I arranged to meet her at a hotel closer to her home on the guise of having to work out that way. I checked into the hotel before our scheduled meeting and had laid out a variety of toys and lubes next to the bed and some condoms on the bedside table.

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? We’d discussed my kinks and fetishes, as well as hers and her limits. She was very naive and claimed to not have any limits in the run-up to our meeting, which proved to be true. I checked into the hotel and she joined me a few minutes later after I’d texted her the room number. She entered the room dressed casually and we embraced and kissed. She told me how much she’d been looking forward to our get together. I had placed the $250 in a greeting card on the dresser and she checked it before heading to the bathroom. She came out in nothing but a bra and panties. She came back over to me and we made out for a while. She massaged my cock through my pants while I massaged her butt. I pushed her down on the bed and started to kiss her all over her body. I pushed aside her bra to uncover her pierced nipples, which I focused my attention on for a long time. Midway through flicking her right nipple, she raised up to help me remove her bra, at which point I went back to licking and kissing her tits. I worked my way down to her crotch, taking breaks to kiss her mouth. I kissed, licked, and massaged her vulva through her panties before removing them. I went back to licking her pussy, fingering her, and using a dildo and a clitoral vibrator on her, bringing her to a gushing orgasm, where she drenched the bed in fluid. I licked up her fluid and captured some in my mouth before kissing her on the mouth, letting her juices flow from my mouth into hers. At this point, I got up and removed my clothes, before getting on top of her and entering her very wet pussy without a condom. I fucked her tight wet cunt for about 4 minutes before cumming inside her. I pulled her so that she was on top of me as my softening penis slid out of her. We cuddled for a bit before we started to make out again. I was hard again pretty quickly, especially when she took me in her mouth and made eye contact with me. When I was hard again, I pulled her up and entered her with her on top. We fucked this way for a few minutes before I pushed her off and started using toys on her again. I traced her wetness down to her anus and pressed around that before getting a bottle of silicone lube and putting a bit on my fingers. I then slowly slid one, then two, and three, fingers into her ass, fucking it gently. With my fingers in her ass, I used a small vibrator on her clit to bring her to another wet orgasm. I then turned her over on her belly, pushed her legs together, and, straddling her, pulled her ass cheeks apart and entered her anus. She bit into the pillow as I entered, but quickly relaxed and I fucked her for nearly 10 minutes before erupting inside her. We cuddled a bit more before she got up to take a shower. She dressed, we embraced and kissed, and she left. I left shortly after, taking a shower of my own.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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 said I’d text her to plan our next get together. She suggested we should go on a hike and fuck in public. I’m not sure if I’m going to see her again or another of the many women who’ve shown interest from the same site.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Sterilization, Discussed STI testing history, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, Power / Dominance

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? I don’t know

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? This is my first mention 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? A little bit

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? My marriage has become non-physical because of medical issues. I’m not talking to my wife about things like this, but I’m also not a monster and feel as though as justified as I feel, she might feel betrayed.

What was the BEST thing about this hookup? Hot sex with a girl 31 years younger than me.

What was the WORST thing about this hookup? I lied to her and my wife, plus I paid her less than she could have gotten for a similar performance if she would just embrace calling herself an escort.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. If you’re not a troll, it’s incredibly easy to find regular girls willing to fuck for money.

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

All things considered, how NEGATIVE was this experience? A little negative

What do you think about the Casual Sex Project? I’ve enjoyed reading it.

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