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What’s your gender? Man
How old are you? 32
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
What’s your sexual orientation? Heterosexual

Mary The MILF

How long ago did this hookup happen? Today

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? One-night stand

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? Mary was in her early 50s, shoulder length straightened blonde hair, nice c cups, bit of a plump round ass and very cute. We were walking into the grocery store at the same time and mutually noticed each other.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I said hi to her and she did the same with a big smile. She was pushing a cart with a very young baby in a carrier in the cart. I walked into the bread aisle and she came up behind me and stopped. As I was grabbing a loaf of bread I looked over and she was smiling at me and said she wanted the same bread. I moved out of the way and she grabbed a loaf too. I introduced myself to her and she did the same. I noticed she was wearing a ring on her finger. We small talked for a bit and then she brought up that she was babysitting for her daughter today as she had to work. We kept talking and ended up shopping together throughout the store. She got into the same line as me and I waited after paying to help her load her groceries. She was parked towards the end of the lot. She was driving a large Denali SUV. I helped her load all the groceries into the back of her SUV as she put the baby inside. When she was done she walked back to me and thanked me for helping her. I asked for her number at that point. She told me she was married and couldn’t give out her number. I was a little shocked with that answer with all the flirting and talking we did in the store. She then said she really did find me attractive and wished I wasn’t so young. I asked why is that? She said because I’d probably screw your brains out in the back seat. I told her I found her very attractive as well and would take that offer. She got a little devil grin on her face and we both hopped into the back seat and closed the door.

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? She pushed the seats forward in the front and she had me sit on the bench seat in the back next to the baby which was kind of weird. She then got down in front of me and unzipped my pants and pulled out my cock. She went right to work on my cock and started to deep throat me like a pro. She was very skilled at giving head and it felt amazing. She then pulled off her pants and panties and crawled on top of me. She said we didn’t need a condom as she was on the ring. She lowered herself onto my cock. I grabbed her plump ass and she started grinding on top of me. We kissed and she pulled off her shirt. She kept her bra on but damn she had some nice tits. She came 2 times riding on top of me before I was close. She kept riding me the whole time as I shot my load up inside of her. She sat on top of me and we kissed until I started to go soft. We both got dressed and then we left.

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? Never got her number but wish I would have. Maybe I’ll run into her again

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), 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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Fucking a hot milf

What was the WORST thing about this hookup? Wanted to fuck her ass

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