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What’s your gender? Man
How old are you? 57
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Seattle
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Retired
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Divorced and testing the waters
How many sexual partners have you had in your life (including oral sex)? 15

Balls Deep And Cumming In My New Friend

How long ago did this hookup happen? 3 months ago

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

How would you best classify this hookup? Short fling

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? I’m divorced and recently have been using dating apps to find partners for myself. I was seeing a 27-year-old brunette for a few weeks and loved spending time with a younger woman. After that fling was over, I matched with a young 19-year-old ebony teen. Initially, I was hesitant due to her young age, but I figured what the heck and sent her a message.

Heather was a beautiful bbw ebony woman. She had thick legs and was curvy with a giant bubble butt and large breasts. After a few back and forth messages, we agreed to meet. I took her out to dinner, and we hit it off fairly well. I ask her if she had ever been with an older man, and she said that she had not. But she was tired of guys her age and wanted to be with someone more experienced. After dinner, we left and I took her back to my place.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We got to my place, and I made us drinks. Afterward, she began kissing me, and I led her up to the bedroom

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 got busy right away undressing each other. I got her down to nothing but her panties, and when she got on her knees, she took me into her mouth. I sat down on the edge on my bed while she pleasured my cock, running her tongue all around the head and inside the tip. I jolted a bit to the roughness and reached behind her and began fingering her ass and pussy while she continued to suck the soul out of me. I could feel her pussy getting ripe with juice, so I grabbed her thick legs and pulled them over my face as I laid back on the bed. Her pussy tasted sweet as we 69ed each other on the bed, her massive ass covering my whole face. I continued to drink her nectar until she lifted a leg up and got off me and spun around. We kissed and then she asked if I had any condoms. I told her no but that I’d had a vasectomy and was clean. Although having had the procedure, I still had a late pregnancy scare with my ex-wife, but with this young girl, I was not gonna mention any of that.

Without needing any lube, she climbed on me and rode me cowgirl style as her ass bounced on me. I felt every rib and curvature of her pussy’s walls. We do this for only a few minutes before I unloaded in her. My penis pulsated uncontrollably as I shot cum deep inside her. I’m embarrassed at how fast she made me come, but she just starting sucking me again, cleaning off the remaining cum and sucking out any remaining sperm. She did not do this for long until I was ready to go again. This time she turned around and presented her big ass to me for doggy style. I slide into her wet, cum filled pussy and began pumping her. I was fucking her on my bed when I looked over at the dresser mirror and saw the reflection of us fucking in it, which turned me on even more. I pumped her for another 30 minutes before shooting another load inside her. I don’t think she had cum yet at that point, so I laid her on her back and began eating her out and playing with her pussy, pushing any cum that dripped out back in. I placed a couple of pillows under her ass to raise it and then I spread her legs and enter her again, but this time in missionary. The angle that I was in her was finally hitting her g-spot, and I felt her pussy tighten as she finally came. I was balls deep inside her as I felt a wave of juice run out and drip from my balls into her ass and onto my bed. The bed was soaked in the juices of our lovemaking as I laid on top of her, slowly moving back and forth in her as she recovered from her first orgasm. We had sex in this position for another 2 hours, and she came twice until I finally mustered an upload of semen to deposit in her. My balls pulsated as every last drop drained into her cervix. I laid on her with my cock still inside her for a few minutes as it pulsed out the last drops of sperm.

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? We have been sleeping with each other for 3 months now. Some weeks we even spend 5 nights or more together. It is amazing sleeping with someone so much younger; she brings so much energy out of me every time. When I’m inside her, I feel close to heaven.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, Making new friends, Just happened, I don’t know why, just went along with it, It was easy/convenient

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? I told my colleagues and kids. My colleagues were jealous, my son approved, but my daughters didn’t.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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 thought the sex I had in my twenties and thirties would be the highlight of my life, but I never thought that at almost 60 I would be having such amazing sex with someone almost 40 years younger than me. I’ve been on cloud 9 for the past 3 months.

What was the WORST thing about this hookup? About a month ago, Heather informed me that she had missed her period, and after visiting the doctor, she was confirmed pregnant. So, as I feared, my procedure hadn’t sterilized me as I had once thought. We will do a paternity test when the baby is born, but I’m fairly positive I am the father. She wants to keep it and make things official between us, but at 57, I’m not interested in getting remarried, especially to the teenage tinder slut I got pregnant. I would prefer to just pay her child support and keep her as a GF on the side, but we will see how things go.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I need to see my doctor about why my vasectomy failed. I thought that I shouldn’t have to wear condoms until I died, but I’m not Mick Jagger, and can’t keep having kids in my 60s and 70s.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? This will be my first mixed-race child, so a part of me is curious about how our baby will look.

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? Society keeps changing and more and more taboo things are becoming accepted, and soon I hope relationships such as mine will be accepted too.

What do you think about the Casual Sex Project? I enjoy sharing my sexual experiences with others.

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