It Started In NY

by DirtyDr

What’s your gender? Man
How old are you? 33
What’s your race/ethnicity? Black
What continent do you live on? North America
What country and/or city do you live in? Mississippi
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Entrepreneur
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? NA
How many sexual partners have you had in your life (including oral sex)? ~10
How many hookup stories have you here posted before? 2

It Started In NY

How long ago did this hookup happen? Over a year

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

How would you best classify this hookup? Short fling

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? She’s from the Middle East, in Kazakhstan. She is beautiful and looks like a model. I knew her very well because we talked for over 6 months before we met in person. We had never hooked up before and didn’t clearly plan to upon meeting. I met her online initially, but the physical meetup was in New York on business. I was totally into her before the hookup and she liked me too, but we wanted to respect each other’s marriages.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The hookup began in an Airbnb. She had never traveled throughout the US, so I helped her look for a room in NY near me so we could go to the business meeting together. Well, we couldn’t find separate locations that weren’t too expensive and the ones with a good price were with only 1 bed. It was too late to keep looking, so we just booked it and said we would just stay on our own sides .

I ended up arriving hours later than her, so when I got there, she was already in bed. She had to get up to let me in. She gave me a hug then got back in bed as I went to change into shorts and a t-shirt and brush my teeth and such. When I got back in bed, we talked for a bit and soon fell asleep. Within less than an hour, I woke up in a panic. She asked what was wrong and I said I wasn’t sure if now was the smartest call time to tell her. She said STFU and just say it. So I confessed that I dreamt that we “did something”. She got silent and laid back down. It was an awkward silence for a bit then she said, “I had a similar dream.” I then jokingly moved a pillow between us and we giggled then fell back asleep. We both tossed and turned constantly after that. Eventually, I felt her leg fall on mine. Slowly, I moved my hand over and started to caress her leg. It clearly relaxed her, as she slid closer to me and rested her head on my chest. This relaxed me, so I instigated it further from there.

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? I started caressing her back and she was really enjoying it. Slowly, she started to sexually move her body and moan slightly. I kept going down further and further. Eventually, I was at her ass. I stopped at the top of her crack, but then she did that inward arching of the back, pushing her ass up as if she wanted me to keep going down…so I did. Eventually, I had an entire butt cheek in my hand. The plan was to just fall back to sleep with my hand cupping her ass. I wanted to stop but didn’t at the same time, so I kept massaging her ass as she continued to move in pleasure. Eventually, I went further down than I planed; my middle and index fingers slightly plunged into the back of her SOAKING wet pussy. I jumped, pulling my hands out her shorts and apologizing. “I’m sorry I didn’t mean to go that far.” She said, “It’s okay, we both got carried away,” so we stopped. Only minutes later, she reached over and squeezed my dick, saying, “now we’re even. Haha.”

I got soooo hard after that and I pulled her in tightly saying, “mmm girl you’re gonna drive me crazy.” So she said, “do something about it.” That was my green light. I put my had back in her pants and returned to massaging her ass but quickly went on down to her pussy. I told her she was so wet and she said she had been that way since she first saw me walk in the door. At they point, I made her lift her hips and moved my hand from the back to the front. I started playing with her clit and she started to melt. She was so hot though, so I wanted to taste her. I got up, pulled her shorts down and wasted no time burying my tongue in her pussy. I’ve got great stamina for oral, so I took my time studying what she likes and literally went down on her for nearly an hour straight. She mentioned it’s really hard for her to cum from oral, so I shouldn’t feel bad. I was up for the challenge though so I tried a little longer. It didn’t work, but she said she was so close. We laid there for a bit and I would take her pussy juices and use them to jerk off a bit. She asked if I had a condom and I said no because this wasn’t supposed to happen. We were both annoyed. We wanted to fuck so bad at this point.

Eventually, we just started making out, then she climbed on top of me. She straggled my dick but my shirt was still on. After a few seconds, she said, get up and go pee, and make sure there’s no pre-cum. I did just that. When I returned and laid down, she straddled me again and made out with me more. Then she leaned forward and moved my shorts to try and pull my dick out. I lifted my hips and removed my shorts. She took a deep breath, kissed me deeply, then grabbed my dick and sat all the way down on it. It took forces beyond belief to not instantly cum inside her. She rode me better than I had ever been ridden before. I had to stop her a few times to prevent from cumming. We changed into missionary for a while and then doggie, then back into missionary. It was so good and she was loving it also. I was getting close and told her I was about to cum. She moaned in frustration, saying she didn’t want me to pull out, but we had to since we didn’t have a condom. I got all the way to the edge of exploding just before pulling out. My cum literally trailed from her clit to her belly button where I left a nice pool of cum. At this time it was only a few hours before we needed to get up for our meeting. We passed out, then overslept a bit. We “weren’t supposed to know each other very closely” so it was a bit awkward at the training while trying to act like it was our first time meeting lol.

We met a few more times over the next year…more stories to come.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? Coming in another story. There was much more sex just as a hint.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Plan B / Emergency contraception

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Making new friends

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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 didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? Very few people. They thought it was pretty awesome.

How would you best summarize people’s reactions about this hookup? Relatively positive

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? Learning new things to try on my wife.

What was the WORST thing about this hookup? That it couldn’t have carried on longer.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Completely.

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? It was the first girl I had fucked since being married.

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? More open minds to trying non-traditional things around sex, and less judgment around girls who love casual sex.

What do you think about the Casual Sex Project? Its phenomenal. Great idea.

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