by RandomGuy

Gender: Male
Age: 30
Race/ethnicity: Caucasian
Current location: Los Angeles
Highest education received: College degree (eg., BA, BS)
Occupation: Management
Relationship status: Single
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 18+

MILF at the Strip Club

How long ago did this hookup happen? Last Night

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One night stand

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? Kelly in her mid 40’s, 5’10”, fake tits, half-white half-Brazilian with a nice waxed pussy. She was a brunette with a bleach blond streak in her hair. Think a slightly darker Marisa Tomei.

We had met casually and have never met before.

My first impression was “DAMN!”

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had an itch to hookup after work so I hit up a bar and a club. Nothing really was happening so I decided to unwind at a strip club a friend owns. He was out for the night but since the staff knows me they let me get a free drink. I know a few of the girls and one gave me a lap dance for free though I usually pay anyways. While she danced I heard a bunch of women cheering. I asked what was going on. Apparently it was a bachelorette party. One of the girls at the club was friends with them so they organized the party there so the bride-to-be could get a lap dance.

A little later I saw the party outside. Kelly walked over to the bar to get a drink. I struck up a conversation with her and made it obvious I was into her. She said she was divorced with two kids. I asked if she was seeing anyone? She said no. After some more conversation I straight up asked if she wanted to spend the night. I could tell she was thinking hard on it so I pushed a little harder. She eventually said sure and walked over to her group and said she was leaving with me. Her friend walked over with her and basically grilled me to make sure I wasn’t a psycho. When she asked what my motive was. I said “Kelly is very beautiful, I would like to have a good night with her. If she doesn’t want to do anything at any point I’ll bring her home safe and sound.”

A few more questions and she left. Kelly and I took my car to my place. We didn’t even make it to the apartment before we were making out.

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? Getting to the apartment we dropped on my bed and passionately made out. She apologized she wasn’t wearing any sexy underwear having not expected to end up at a guy’s place. I responded by stripping her and eating her out. Her moans were amazing. After getting her thoroughly wet, she went down on me. She was very good at deep throating and I nearly came from that.

I plopped on a condom and entered her. For having two kids, she had the pussy of an 18-year-old virgin! It felt amazing. She actually came pretty quick after we began but she said she was multi-orgasmic and to keep going. I flipped her over doggy style and she came again. I laid down and she rode me reverse cowgirl. I slapped her ass as she rode me. I have a giant mirrored closet next to the bed so both of us were enjoying the show as we fucked. As I was about to cum, she said she was close to her third. We ended up cumming at the same exact time.

She slid off me and we kissed passionately. She slid down and took the condom off and licked my dick clean making it hard again. She deep-throated me until I came deep into her throat. She swallowed and she laid beside me as we both fell asleep.

When we woke up in the morning she got into the shower as I made breakfast. She walked out in just a white work shirt of mine. I sat her on my kitchen table and made out with her. My dick got hard, so she pulled it out and jerked it off a bit. She was feeling it as well so she said she wanted to fuck. I said I would go get a condom. She said it didn’t matter as she had her tubes tied. She asked if I was clean I said yes and she was as well so as she sat on the kitchen table she spread her legs and I shoved my dick into her. We fucked like that for about 20 minutes. She came twice and then I came, filling her MILF pussy with my cum.

Did you have an orgasm? Did your partner(s)? I came twice. She came five times.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We wore a condom the first time but nothing the second time. We trusted each other to be clean.

What were your REASONS for having this hookup? I was looking for a night of passion and so was she. She hadn’t had a good night’s sex in over a year so it was great for both of us.

Were alcohol or drugs involved? If so, how much? We had drinks. Enough to loosen but not enough to get drunk.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We cleaned up, had breakfast and I took her home. She had known she would probably be out all night so her sister stayed to watch the kids. She kissed me and gave me her phone number saying she wanted to do that again whenever I felt like it. I kissed her and agreed.

I would love to hook up with her again. She is hot and has an amazing sex drive. I have no problems helping her fulfill her cravings.

To whom did you talk about the hookup? How did they react? It just happened so no one really. She said she might tell her sister since they don’t keep secrets. Apparently her sister had told her she needed a hookup so yeah.

Was this a consensual and/or wanted experience for you? For your partner? Yes.

Do you regret this hookup? If so, why? Not at all.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Having an amazing night of sex with a woman who despite being in her 40s with kids was like fucking a goddess of sex!

If there was a worst it would be that we can’t just have sex whenever, since she does have kids.

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

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

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