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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? Boston
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Management
What’s your current relationship status? Single
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)? Dozens
How many hookup stories have you here posted before? None

Delicious Dallas Date

How long ago did this hookup happen? 5 years

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? We met in a hotel bar in Austin while I was traveling independently. She is about 5’6”, very toned, pretty face, sharp and caustic wit. We got along well and she said to call her if I was ever in Dallas

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was heading to Dallas and texted her. I am sure she was quite surprised to hear from me but we arranged to meet for dinner at a great place we both knew. We hit it off well and then headed to a bar. We ended up having drinks on some weird huge beanbag sofa that had the effect of throwing us together. Amidst the closeness, we started making out. Then we got a bit handsy. At one point she was stroking my cock from outside my pants and she disengaged, looked around a bit embarrassed, and said: “we should probably get out of here.”

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? We caught a cab and she said: “where can I drop you?”; I replied “your bed.” She gave her address and we were off. Once in her place, we were naked pretty quickly. She stated that she did not want to have sex but was happy to fool around and that her period had recently ended. She fellated me for a heck of a long time while I pleasured her. She came from my fingers a few times and I ejaculated in her mouth. Afterward, we made out and when she felt me getting hard again she said: “you are joining me in the shower.”

It was a huge shower with multiple nozzles, a bench shelf and a wooden bench in the middle. She sat on the bench and blew me again before standing up, grabbing my cock, turning her back to me, and bending over. She nudged my cock against her vagina and grabbed her ankles as she leaned back. I sunk right in.

I fucked her like that for a while until she pulled off and pushed me down onto the wooden bench. Then she straddled me and proceeded to fuck me. The stool and I were low enough that she could easily raise and lower herself and slide back and forth. I wasn’t quite supine as my upper back and shoulders were against the wall. It was clear that my role was to be a stationary saddle as she rode into battle atop me. She orgasmed a few times and after a while, she slowed. We had been intermittently kissing and at one point she pulled back and simply said: “finish in me”. I did, then we toweled off and fell asleep

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 a very early morning. I showered and dressed (nice conservative suit) while she slept. Just before she showed me out the door, she kissed me goodbye. Her robe fell open and I leaned down to nibble on her nipple which was now showing and incredibly erect. I nipped it and sucked it in. She gasped and immediately grabbed my cock. We stayed like that – me sucking her and toothing her nipple hard while she fished my cock through my fly. Then she backed us up until we met a footstool which she sat on and proceeded to suck me. Sober, she was much better (or I was). She deepthroated me and I came rather quickly. She swallowed but couldn’t keep up so a good bit was dribbling down from the corner of her mouth to her chin as she ushered me out to my waiting cab.

I had an excellent series of client meetings with a smile on my face that day!

We stayed in touch and were FWB for about two years. She was a pretty senior exec in her firm and we met occasionally in NYC and went skiing twice. It ended when she began a relationship with a future.

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

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

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? No one

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 woman; great sex

What was the WORST thing about this hookup? Absolutely nothing

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 a huge fan of casual sex provided all eyes are open

What do you think about the Casual Sex Project? It’s great

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