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What’s your gender? Man
How old are you? 44
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Colorado
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 30+
How many hookup stories have you here posted before? A couple

Wine Makes Her Horny

How long ago did this hookup happen? 6 years ago

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? For less than a month

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? Kristy was in her 40s, a professional, and a single mom. We had met online and had chatted several times. Although I had met someone else recently and started what appeared to be a serious monogamous relationship, I liked my conversations with Kristy and thought there was no harm in meeting over drinks and a meal.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met on a Friday night for drinks and a meal at a local restaurant. I really had no plans for anything physical, but as the night went on, we drank more wine and had some great conversation. Time got away from us and it came to be closing time. We left the restaurant but kept chatting. It was cold out so I walked her to her car.

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? Kristy owned a large SUV, so we went inside to warm up and kept up the conversation. I told her I needed to leave as I had some early morning commitments. Instead, she leaned in and kissed me. I enjoyed and returned the kiss as she crawled over the console and stratled me in the passenger seat. As we kissed, she rubbed my crotch and could tell I was very hard. It was the end of summer and she had a dress on. With her lips still on mine, she pulled up her dress and pulled her panties down in one motion. She then unbuckled my belt and let my cock out. She mounted me and began to enthusiastically ride my cock. I found a way to get her nipples to peak out of her dress and sucked on them with delight. She seemed very wet as she rode me and as she neared climax, I had my first experience with a woman squirting as she gushed all over the place while still riding me. I had no idea what happened initially or what to do, but I hadn’t got off yet, so I rolled her over in the front seat, put her feet up on the dash and pulled her hips forward so I could kneel on the floor and enter her again. It didn’t take long for my knees to get sore and then she suggested we move to the back seat so I could do her doggie. The dress made for easy access, but my pants were soaked, so I pulled them down around my ankles and pounded away. Her ass was bigger than I had noticed in her dress so I enjoyed grabbing her hips and pulling her toward me with each thrust. To my surprise she squirted again and with that my nuts exploded inside her. We tried to put ourselves together at that point and made plans to meet for coffee the next day. I made a call for a cab and found my way back home.

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? I met her for coffee the next morning and she clearly thought this was way more than I did. She didn’t seem near as attractive in sweats and morning hair. I already felt bad that I fucked someone when I was beginning a relationship. I made it through the meetup, but that was the last time we talked.

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

What were your motives for this hookup? Intoxication, It was easy / convenient

How intoxicated were you? Completely wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Completely wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Nobody

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? Cheating on someone who became a serious relationship.

What was the BEST thing about this hookup? Had never experienced a woman squirting before!

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

All things considered, how NEGATIVE was this experience? A little 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 wish people were more open to casual sex. Unfortunately I think I hurt some feelings with this one.

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