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What’s your gender? Man
How old are you? 64
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? New England
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Business Consultant
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Avid
How many sexual partners have you had in your life (including oral sex)? 100+
How many hookup stories have you here posted before? 1

Picked Up

How long ago did this hookup happen? Yesterday

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Paid sex

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? V sat down on the next stool at a midtown Manhattan hotel bar. I noticed an attractive older blond, probably 50s, dressed in black, with a coat so it looked like she came in from outside. She ordered a craft beer on tap.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was sitting at the bar, sipping a glass of wine and reading a history book on my Kindle. I finished a chapter and looked over at a TV to see which Olympic events were on screen. There was an impossibly cute dog on an adjacent screen that was airing a dog show and we started to chat. She commented that I was alone and was I looking for “something special” that night, like a massage. I’ve heard this before and began the negotiations with a non-committal “it depends”. After 20 or 30 minutes of flirting and discussing enough of the specifics (price and activities), we were headed to my room. I had a planned sex encounter with a pro canceled last week so I had an envelope with the negotiated amount ready to go. I’m sure that knowing this affected my decision making beforehand.

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 was good humored and because each of us had done this before there wasn’t any nervousness or awkwardness. We took turns in the bath to get ready when I came out she was in her Victoria’s Secret panties and bra and had turned down one of the beds. I slipped off my clothes, walked over and started with a kiss. She fondled my cock with a free hand and soon we were on the bed, naked, and exploring each other’s bodies. Oral sex, cowgirl, and missionary were all on the agenda. V’s body was sexy to me: just enough curves, a nice soft ass and hips, and smallish breasts, with a little mileage. We fucked with vigor and passion and I enjoyed that our rhythm and parts fit together from the beginning. V’s pussy was not especially tight and it was 20 minutes of hard fucking before I came.

We recovered and she cleaned me up. I rubbed her back softly as we talked and recovered and within 15 minutes we were on to round #2. We started in cowgirl but in one of our position changes she took off the condom and began jacking me off until I finished a second time. It was very sexy and was the right call.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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? We exchanged contact info, kissed a last time and she was on her way. I looked at ad sites and review sites and didn’t find her listed, but her e-mail address connected her to a legit business. I slept soundly after the encounter and thinking about the sex made me smile the next day. I enjoy new partners, especially when we are in sync in bed and V was one of the best fits. I only hobby a few times a year, but I would happily reach out to V on my next trip to New York if it fit into my hobbying schedule and budget.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), To feel more desirable, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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? This is a clandestine activity for me

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Great sex with someone new. I love the feeling of being close to a sexy body

What was the WORST thing about this hookup? The cost (but it is a fair trade for no-strings)

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It was affirming, but didn’t cause any change in the way I think about things

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

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

Anything else you want to add about this hookup? Even though I was reading and keeping to myself in the bar, it is a known hot spot for pickups like this. I must have known that an encounter was a possibility at a subconscious level.

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? Society should be more accepting of casual sex. Jealousy and insecurity are unhelpful, but we are all affected. There are 3 or 4 women in my regular social circle who I would love to have sex with if that was a thing – but it would be too complicated as things are today.

What do you think about the Casual Sex Project? Love the stories, and I like the opportunity to share thoughts that I would otherwise keep private.

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