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What’s your gender? Man
How old are you? 49
What’s your race/ethnicity? Black
What continent do you live on? North America
What country and/or city do you live in? Kansas City
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Senior Scientist
What’s your current relationship status? Legally separated
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Once is never enough!
How many sexual partners have you had in your life (including oral sex)? Over 100
How many hookup stories have you here posted before? 0

Hot Jewish MILF

How long ago did this hookup happen? 5 Months

What was your relationship status at the time? Same as current status

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

How long did you know the person before this hookup? For less than a week

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? We exchanged initial greetings on an adult hookup site. After I saw her sexy ass pics I was sold and, knew I had to meet her although I hadn’t seen her face. She was a really cute, curvy MILF, age 51 but looking like she was 35, with curly hair, and beautiful tits. Later, when I had the chance to grab her ass, I found it was damn near perfect. We met at a downtown bar for drinks and I could barely keep my hands off her. We went for a short walk, then a drive, and made out in the car. She sucked my cock and I put my fingers in her pussy and then watched as she rubbed her clit to an orgasm. She is the sexiest woman I have ever met. I was hard the entire time we were together, which was a bit uncomfortable!

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We both instigated it. About a week later, I got us a room with one idea in mind. We’d be fucking soon.

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? Upon arrival at the motel, we had a quick cigarette and I got to watch her undress and admire her ass up close and personal: We kissed and then I ate out her pussy. Then, she gave me the best head I’ve ever had, never had my cock been sucked like that. I knew if she continued I’d cum, so I stopped her and put the condom on. We got in doggie style position and I entered her pussy for the first time. She was just tight enough but it stretched to accommodate my cock. I pounded her while looking at her ass which, in itself, was enough to make me cum. I knew I couldn’t hold out long since I’d been thinking about fucking her ever since our first meeting, so I fucked her hard as I could and released that first load. After a brief rest and encouraged by a little bit more of her amazing cock sucking skills, I was hard again and ready to fuck missionary style, so I could be on top of her and feel those big titties. I entered her again and fucked her deeply, releasing that second load. It was getting late and we both had work the next morning, so we called it a night but knew we’d meet again.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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? After the hook-up, we began planning the next date. We’re still fucking and it’s better than ever!

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), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more

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? A friend

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? I met my Jewish MILF. I crave Jewish women and got my wish; she’s everything I ever hoped for and then some.

What was the WORST thing about this hookup? Nothing except I wish we could fuck every day

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Nope. We all need sex so let’s fuck responsibly and not be judgmental

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 wish we had more time that first night we met

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? If you’re not getting enough sex in your relationship, casual may be just what you need. Be open and honest about it and make sure there are ground rules so that there are no misunderstandings.

What do you think about the Casual Sex Project? It’s a great idea, please keep up the work and post more stories!

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