Anal With The Italian


What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? England
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Chartered surveyor
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Fetish for women with pubic hair and larger than average clitoris and labia
How many sexual partners have you had in your life (including oral sex)? Over 50
How many hookup stories have you here posted before? None posted

Anal With The Italian

How long ago did this hookup happen? 15 years

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? I have been visiting prostitutes and massage parlors on and off since I was in my mid-twenties. Leila claimed to be an Italian student around 25 years old and I was in my thirties. She was working as an escort to help pay her way through college, apparently. Leila was very pretty, green eyes, a wide mouth, and waist-length dark curly hair. When she was on all fours I saw that her pubic hair grew between her cheeks and around her anus, which I found to be a huge turn on.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Leila had an ad in my local newspaper. I rang the number listed and arranged to meet her. I knew the apartment, as I had seen other women there 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? I paid for a one-hour appointment. Leila massaged me for a while, and I returned the favor while we were both naked. She then went down on me and I went down on her. These paid-for encounters can be very mechanical, but Leila was very engaged. She kept speaking in Italian and broken English which encouraged me further. We had vaginal sex before I suggested anal. She was initially reluctant on account of my size, but I persuaded her and spent some time rimming her beforehand. Her vagina was very wet, and I spread some of the juice from her pussy to her bum, but we had to apply a lot of lube. It took some time for me to enter her fully. Leila said it was uncomfortable but exciting at the same time. I fucked her in this position for several minutes before coming into her arse.

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? I went home and masturbated later that night thinking about it. I never saw Leila again and it remains the one and only time I paid for anal sex.

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, Attraction to partner(s), Learning new things, experimenting, To cheer myself up, Power / Dominance, 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? Nobody

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? Fucking a girl’s hairy arse.

What was the WORST thing about this hookup? I had to pay money for it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It hasn’t

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 it and I think we should be having more of it.

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

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