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What’s your gender? Man
How old are you? 27
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Moscow, Russia
Highest education received: High school diploma
What’s your occupation? Lawyer
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation:
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 16
How many hookup stories have you here posted before? 0

First Creampie

How long ago did this hookup happen? 5 years

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For less than 6 months

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 Anastasia while taking history lessons. She is a pretty woman in her mid-30s. Though I found her attractive and enjoyed talking to her, I didn’t originally think about her sexually, as she was married and has a young son. I was dating two girls in parallel at that time and was very satisfied with my sex life. I was quite experienced in sex, though I have never fucked without a condom.

We met from time to time, visiting museums and attending our history lessons. We quickly became very close in communication and discussed sex and relationships as well. She told me she wasn’t very satisfied with her sex life because her husband is a very lazy, poor lover and was increasingly indifferent to her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? That day, we were visiting a museum and then having lunch. I was driving her back home. She was dressed very hotly: short elegant skirt offered a view of her beautiful legs in black stockings and high heels, shirt and jacket allowed me to see her perfectly shaped boobs. So I suspect there was some planning involved on her part. When I stopped the car near her home, we kissed and I thought she was going to leave, but she didn’t. Instead, she started kissing me more deeply and stretched her hands to my breeches.

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 didn’t expect this and was completely stunned, but excited by her deep kissing and touching. She unbuckled my breeches, and my hard cock jumped out. She took it in her hand, smiled and said: “Not bad.” She moved her head from my lips to my cock and started sucking.

The way she sucked my cock was completely different from what I had experienced with girls I have dated before. I don’t know how a person can use one’s lips and tongue so masterly but I realized other girls knew absolutely nothing about how a proper blowjob is done!
She pulled my dick out of her mouth, leaned back on her seat, took her panties off, pulled her skirt up and spread her legs. I could see her beautiful, clean shaven pussy. I looked at it completely embarrassed.

“What are you waiting for?” she asked. “Come on, get in. This pussy is craving for a proper fuck!” “Sorry, I don’t have condoms,” I murmured. “Do you?” “No. You won’t need any,” she answered. “Is it safe?” I asked. “Come on, honey, I haven’t been fucking anyone but my husband for past ten years, and even that happened only on holidays! I’m clean.” “But what if your husband finds out?” “He won’t. Fuck, don’t think about him, it’s you, not him, who is going to enter my pussy now!”

It was impossible to resist. My cock was all hot and horny, leaking precum. She looked so stunning with her unbelievable stockings-clad legs spread across my car… so I dived between them and entered her wet, hot pussy. It was a fantastic pleasure, as I was feeling a woman’s pussy without a condom for the first time. As an experienced lover, Anastasia could squeeze her vagina and grab my cock, driving me insane. Sometimes her pussy contracted unintentionally when she climaxed; she turned out to be a very sensitive woman and said to have reached orgasm at least three times. It was hard to endure and I felt I was going to cum so I pulled out.

“Where are you going?” she asked. “I’m going to cum,” I answered. “Cum inside me,” she said, grabbing my cock with her hand and inserting my cock back inside her. She gripped me with her incredible legs so that I wouldn’t pull out, and I kept pounding her as she moaned louder and louder. Thrusting inside of her, I shot my huge load deep into her, having one of the best orgasms I’ve ever had.

“Oh wow,” she could only say when my cock’s contractions stopped. “I think your husband is waiting for you,” I replied. Yes, perhaps I should be going now,” she said. “If you would please exit me.”

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? We kept on meeting for casual sex, and for a long time, she was the only woman I could fuck without a condom and cum inside. We didn’t want any strings to be attached, as she was married and I was dating girls of my age with a perspective of future marriage. She eventually grew tired of being “just a pussy to fuck” and thought it to be more and more offensive. We finally stopped fucking after I married, although we still remain friends. Without benefits any more 🙂

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, To feel more confident

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? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Just a pair of close friends and they approved that I could learn much from sex with an experienced partner.

How would you best summarize people’s reactions about this hookup? Relatively positive

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? Not at all

What was the BEST thing about this hookup? Fucking without a condom and cuming inside a pussy for the first time. More than that, fucking a married woman and leaving my semen inside her made me feel victorious over another man!

What was the WORST thing about this hookup? After that, I started to get less pleasure from having sex with a condom.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I grew a taste for married women a bit older than me; they are harder to get than single girls, but once got, make awesome lovers!

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? I learned that if my own wife isn’t satisfied she could cheat on me; so I try never to leave her holes idle!

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? Sex is the best thing in human life, so have sex and be happy! I would like society to become more tolerant of casual sex. I would like women who are not satisfied by their husbands and therefore seek sexual experience elsewhere wouldn’t be stigmatized as whores.

What do you think about the Casual Sex Project? You’re awesome, keep going!

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