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What’s your gender? Man
How old are you? 37
What’s your race/ethnicity? Black
What continent do you live on? North America
What country and/or city do you live in? NYC
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Religious affiliation: Christian
How religious are you? A little
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

Minneapolis Match

How long ago did this hookup happen? 1 year

How would you best classify this hookup? One-night stand

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? She is a brunette and is a little chubby but had nice large breasts.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I matched with Jessica while traveling for work. She was younger, in her late 20s, and managed a retail clothing shop. We had little in common, and she was in a different socio-economic place, but she was cute and responded to the sexual overtures enthusiastically. We flirted that evening and sent some pictures, but nothing came of it. I think she may have had a boyfriend and couldn’t hook up that night. The next morning, I woke up horny and did not have any work obligations until the afternoon. I asked Jessica if she wanted to come over and ‘work up an appetite’ and grab breakfast. She agreed and was over within an hour.

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? Jessica arrived bundled up but true to her pics: a little chubby with very large breasts. Her face was very cute (my weakness), and she has a great smile. I’m in shape, well put together, and I’ve been told by many that I’m a very attractive man. Jessica made it obvious she thought so and nervously agreed to go to my room.

Upon entering, she sat on the bed and we chatted after her jacket was removed. She had some coffee and was nervously saying she’d never randomly had sex with anyone. I told her she was cute, and I was very attracted to her. That seemed to relax her, so I sat on the bed and kissed her and held her head gently. She was a good kisser but had coffee breath. I had previously mentioned that I was very dominant in bed to which Jessica said she wanted. I told Jessica she was a good kisser as I stood up and put a finger in her mouth to suck. She did as she squeezed my hard-on through my pants. I pushed her on her back and pulled her pants off to see the black thong I’d mentioned I’d like to see. A finger in her pussy revealed she was very wet and on fire.

I stood up, grabbed a pillow, and moved in front of the full-length mirror. Jessica froze for a second as if she wasn’t sure what do do. I unblocked my belt and hit her, and she was quickly on her knees undoing my pants as she looked up at me. I’m usually a grower but hadn’t cum in a few, so I was already getting hard. As she pulled my briefs down, my erect penis popped out and hit her in the forehead. She giggled and commented on how long my cock is. I grabbed her hair and slapped her face with it, smearing pre-cum around before she began devouring it and trying her best to deepthroat. I put my hands on my hips and admired the view in the mirror. Jessica gave great head, taking direction very well, and finally, appeared to be relaxed and completely over the nervousness of a completely random hook-up. She would routinely pause, grabbing my cock and staring at it and making a flattering comment about how hot she thought I was, how she loved my cock, etc… I would shove my cock into her mouth before she finished her thought. I moved to the bed and stripped naked as she did the same. I intended to give her head, but she quickly returned to my cock. I took off the rest of her clothes as she continued to please me before I told her I might finish if she continued blowing me. She told me she wanted to taste my cum and proceeded to cram my cock into her throat. Her nose hitting my pubic bone as she gagged sent me over the edge, and I pulled out intending to cover her face with my cum, but she took the head back into her mouth and milked me, swallowing everything I gave.

After a few minutes of chatting about sex and me fingering her, Jessica began blowing me again until I was hard. As I put a condom I asked her how she wanted to be fucked to which she replied she didn’t care as long as I was on top of and inside her. I obliged and pounded her roughly for about 20 minutes as she played with her clit. She came twice before offering her ass, saying if I started slow I could eventually have my way there as well. I needed her request and before long was pounding her ass in doggy harder than I had ever fucked any woman’s ass before. As I came, I pulled the condom off positioned my cock at her mouth where she took a partial facial and cleaned up and swallowed everything. Seeing her cleaning off my now semi-erect penis with cum on her face and a used condom on the bed next to her head turned me on more, and I began to get hard. Drenched in sweat, I told her I wanted more and she asked, “What more?” She asked what I wanted and I told her, “Whatever you want.” She said, “You’re fucking hot, and I’ll do whatever you want”. I suggested that we rinse off first.

In the shower, Jessica gave fantastic head as we washed the sweat off. I gave her an orgasm by sucking her clit as I fingered her pussy and ass. Moving back to the bed, I made sure she was open to anything I wanted, to which she re-affirmed. Laying on the bed, I pushed her head to my cock, then to my balls. I then pushed her head a little lower to which she resisted and looked up to ask what I wanted. I bluntly told her to put her tongue in my ass. She said that she doesn’t do that and went back to focusing on my balls. I didn’t push the issue but positioned myself so my balls (and ass) were easy for her to get to. As I expected, her tongue soon made its way to my ass, and she began exploring. I stroked myself and began pushing her head into my ass. When I grabbed a condom and began putting it on, she commented that she was on the pill. I asked her what she meant by that and she said that I could have her however I wanted. I responded that maybe we’d go there if there was a next time and finished putting the rubber on and squirting some lube on it. She seemed to take offense to my not going bare but readily positioned herself for more. I pounded her ass again from doggy for a long time before putting her on top, riding me, still anal. She played with her clit as I slapped and squeezed her tits until she came. I came in the condom soon after.

I thought we were finished, especially after the awkwardness about using protection, but Jessica laid there as if waiting for me get erect again. She started squeezing the base of my cock and commented that she loved my length since it allowed her to get more into fucking without me slipping out. I was bored at this point and asked she ever had a belt around her neck. She said no so I got mine out. She was then on her knees with my belt around her neck. She began to suck me as I asked her if she would do ass to mouth. She said that my cock was just in her ass. I said but with a condom to which she replied sharply, “Your choice.” The attitude sparked something in me. After I got hard, I took her doggy in front of the mirror, very roughly, choking her with the belt, slapping her ass, pulling hair, etc. After almost an hour of me using her body, I came in the condom, balls deep in her ass. I stood up and slapped my condom covered cock on her face and shoved it down her throat until I went soft.

We cleaned up and grabbed breakfast at my hotel. She expressed interest in a fuck buddy situation whenever I was in town. I agreed, and we discussed some kinks like group sex, dom/sub, etc. Four hours after we met she was on her way to work.

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? It felt good. I feel nothing for Jessica emotionally, but she was strictly sexual fun. Jessica has stated she is on Tinder for dating not hookups but felt like I’m out of her league so she made an exception. The sex is really good, so she is down for something casual as she looks for a relationship. She later shared that she had a date the night after work following our morning fuck fest and was making out with the guy in his car when he pushed her skirt up to reveal her black, cum stained thong. She was embarrassed, so she pulled her skirt back down. But soon she got turned on by the thought of him eating her pussy that might have my smell, sweat, and semen on it. She pulled her panties off, and he gave her head. Kinky girl.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Birth control pill / patch / ring / injection / implant

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

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 gave enthusiastic consent

To whom did you talk about the hookup? How did they react? A friend

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Lots of sex

What was the WORST thing about this hookup? the awkwardness about using protection

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? None. I like sex and technology has made it easier for women to discretely enjoy casual sex.

All things considered, how POSITIVE was this experience? Fairly 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 enjoy sex.

What do you think about the Casual Sex Project? Great repository

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