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What’s your gender? Man
How old are you? 48
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Houston
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Software Management
What’s your current relationship status? Engaged/Married (monogamous)
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? I have been cheating for the last 4 years off and on
How many sexual partners have you had in your life (including oral sex)? 24
How many hookup stories have you here posted before? 0

Hot MILF

How long ago did this hookup happen? 7 months

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

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

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? This woman was really hot. She is 43. Met her online and she was cute in the photos but in person she’s a knockout. She has a great body and is totally DTF. We had met twice before. We met at a hotel and had a drink downstairs first. Then we went up to the room. I was excited about the hookup because she was hot and wanted it before so I figured she would be ready for it again.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We texted back and forth and I told my wife I would be out of town. We met on a Friday after work and she met me at the hotel. I took care of the hotel.

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? When we got upstairs, she took off her dress and left her bra and panties on. She has great underwear. Then we laid on the bed and started kissing. I took off my pants and she unbuttoned my shirt. I was already hard and she started massaging my dick through my underwear. I laid back and let her hands do the work and then she pulled my underwear down and leaned over to blow me. She easily gives one of the three best blowjobs I have ever had. She had me about to cum when she moved away and pulled her panties off. I put a condom on and I pushed her down and then I drove right in. She is pretty short, about 5’2″ and her pussy is pretty tight so she moaned pretty hard when I entered. But she loosened up quick and got real wet fast. I fucked her missionary style for about 10 minutes. She came once and I was trying to hold it.
We laid in the bed and talked about work and our spouses and then I suggested we fuck in the shower. We went into the fairly large walk in shower and started kissing. She grabbed my semi and started getting me harder. Then she went down on me again and got me hard fast. I put on another condom and I told her to grab the handicap rail. She is pretty short and I am 6’1″ so I had to really squat to get under her but I did and I fucked her hard from behind until I came hard inside her. She has a perfect round ass and I would spread her cheeks to see her pink asshole. I actually came a second time just looking at that asshole.
We dried off and went to the bed. I went down on her for a while and she came. We started talking about all sorts of things, my childhood, and she was on top just sitting on me. She began to kiss me and then she went down and sucked me hard. She put a rubber on me. She got on top and fucked me pretty hard and came on me. We laid in the bed for a while and she said she was seeing someone else, not her husband, and that it was starting to get serious. That just made me want her more.

She got dressed and I walked her out to her car. I was standing there kissing her and I got a hard on. She stroked me in the parking lot in between the cars. She pulled my dick out and was giving me a hand job right there. She wanted it again and told me to get in the back seat. She had condoms in her purse. I put one on and she straddled me and slid right on and fucked me in the parking lot of the hotel while people were near. I came again and she got off of me and kissed me good bye. That was the last time I saw her.

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? I had to stay at the hotel because I had told my wife I was working out of town. That was kind of sucky. I wanted someone to be with me. So it was a lonely night.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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? No one.

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? That woman loves to fuck and suck. She’s really good at it.

What was the WORST thing about this hookup? Staying overnight in a hotel alone. And I never saw her again.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No.

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

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

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? I am not so proud of cheating on my wife that I want to talk about it but I feel like I need an outlet every month or so.

What do you think about the Casual Sex Project? I think it is great.

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

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