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What’s your gender? Man
How old are you? 45
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: High school diploma
What’s your current relationship status? In a serious relationship (open)
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Queer
How many sexual partners have you had in your life (including oral sex)? ~40
How many hookup stories have you here posted before? 0

Pregnant Hooker

How long ago did this hookup happen? 10 years

What was your relationship status at the time? In a relationship (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 was cruising on craigslist for casual sex and saw an ad from a prostitute who was pregnant. I contacted her and we made arrangements to meet. When I contacted her that day I asked if she was still pregnant and she laughed at me. I was relieved, but also worried that she was not showing yet, which is what I was interested in. I do have a fetish for pregnant women, although I had never had sex with one. When I arrived at her place – a tenement-style apartment a short drive from my place – I was not disappointed.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She answered the door in a sort of sexy onesy and she was all popping out! Her belly was extended and huge, and her tits, showing through the lace top, were also huge. Her face was chubby and cute. She invited me in, we did our transaction, and eyed each other rather suspiciously, each unsure if the other was a cop.

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? Finally I asked if I could touch her tits. She said yes, adding that this meant that I was not a cop (I don’t know about that!). I fondled her heavy tits and sucked on her nipples. Soon enough we were both breathing heavily and I had worked a hand into her slit – she was wet. Although I think she had prepped with lube. Her vagina was firm and like all of the rest of her. I couldn’t (and still can’t) believe my incredible luck. I got a finger into her and she moaned. Soon enough I had a condom on and asked if I could fuck her. She responded – “It’s tight as hell, but just shove it in” and I did exactly what she said. She seemed to be enjoying herself and I was just in heaven, lost in all of her – we kissed and I fucked her until a beautiful release.

How sexually satisfying was this hookup? Very

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? We got dressed and she sort of congratulated me saying, “You did what you were supposed to do.” On the way out there was a young man in the kitchen who gave me the most piercing look – I’m sure he was jealous (or her son? I don’t know) I’ve never seen or heard from her since, nor would I, a prostitute from a working class suburb, but I will always remember the experience with great fondness.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have

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 was one of the most satisfying experiences of my life but I’ve never told anyone about it before

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? I always imagined that fucking a pregnant woman would be amazing – the mix of hormones, physical transformation, breast growth, all turned me on incredibly. I was in no way disappointed. My expectations were met and greatly exceeded.

What was the WORST thing about this hookup? Risk associated with criminalization of prostitution.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It was one of many positive hookup / casual sex experiences I have had before and since. It was enjoyable but didn’t change my (positive) outlook on casual sex.

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

All things considered, how NEGATIVE was this experience? Not at all 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? I love casual sex. I believe strongly in consent and in having sex outside of the boundaries enforced by conservative politics, culture and religion.

What do you think about the Casual Sex Project? I love it.

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