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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? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Professor
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? >100
How many hookup stories have you here posted before? 0

Hot little redhead

How long ago did this hookup happen? 1 month

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 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? 27, stunning beauty, thin redhead with super tight abs, small breasts, deep brown eye, gorgeous mischievous smile.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I met her on a “sugar daddy” site that I use occasionally. She lives in DC and I was traveling there for business. I contacted her, we clicked, and corresponded a few weeks beforehand. I mentioned that I was into “dirty underground stuff” and this piqued her interest. She asked me about what that meant and I clarified that this included burlesque shows, watching strangers have sex in clubs, in visiting brothels and RLDs in other countries, and porn. I asked what she liked and her response was “I like porn. I like fucking older men…I like money”. Classic. We corresponded a bit more and she sent some sexy PG-pictures of herself. We agreed to meet for a $400 date during my visit.

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 blew me off the first night of my visit, but felt bad about it and contacted me the next day. I was scheduled to go out for dinner with colleagues, but canceled those plans to meet her. We met up at her favorite sushi restaurant, where we consumed a large prix fixe dinner and several sakis. We talked about ourselves and what we like, but she was more reserved in person than before. Just before we left the restaurant we were discussing musical tastes and I asked her what kind of music she likes….when she is getting fucked hard. She blushed and smiled, we left and walked back to my hotel. She leaned in for a kiss on the elevator, and soon we were naked in my room. I was right, she had an amazing body. She showered while I waited for her and got the room ready. I then showered and came over to her on the bed. We started kissing again and suddenly she tells me that she has her period and wanted to know if that was ok. I wasn’t too bothered by it, it was actually a turn on for me. I Lready knew that we were both STI-free and she had in IUD, but when she asked if we were going to use protection I explained that a) I despise condoms, and 2) it is difficult to get pregnant while you are menstruating. I proceeded to go down on her until she came, then she asked me to fuck her. I moved up into missionary and slowly slid right into her warm pussy. It was so hot and wet. I fucked her like that through two more orgasms, then she needed a break. We held each other until she was ready again, then mounted up onto my cock and slowly slid down. I love a good cowgirl ride, but had never had one so sensual, like she was dancing and my cock was just part of her dance. I cam close to coming, but wanted to hit her from behind before I did, so we moved to doggie. Turns out her legs were too long for this to work, so I rolled her over back into mish, and proceeded to fuck her with her legs on my shoulders. She was begging me to come, so I wound up for a bit, then let a huge load spring deep into her pussy. I was still hard and kept fucking her for a bit, then withdrew so I could admire the nice creampie dripping from her gash. It was swirled red and white. Afterwards I called her an Uber to get her home and we said goodbye.

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 felt great.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, IUD (Intrauterine device), Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness

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

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? Not at all

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? Not at all

What was the BEST thing about this hookup? The memories of watching her gyrating on my cock

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 love casual sex, always wanted it, but have only explored that side of my sexuality in the past 12 years.

What do you think about the Casual Sex Project? Good idea, I will submit more stories. I will keep them real, but I worry that many of them are fake.

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