by Edward

Gender: Male
Age: 30
Race/ethnicity: White
Current location: NYC
Highest education received: College degree (eg., BA, BS)
Relationship status: Married
How religious are you? Not at all
Sexual orientation: Mostly hetero
How many sexual partners have you had in your life (including oral sex)? 30
How many hookup stories have you here posted before? None

The Great Fling

How long ago did this hookup happen? 7 years

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Short fling

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 was a little older than me. A bit plain, but had the most incredibly soft skin and straight black hair. We had met a couple of times for drinks. We lived in the same town at the time. Small place and she tried to date me through Facebook. We knew some of the same people and met up a few times. She was nice, wasn’t really my type, but we could feel a sexual tension building.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met at a bar and had a couple of drinks. She had texted me what I was doing for that evening. We talked for a bit and after our drinks I walked her to her car and we made out. She didn’t know if she wanted to hook up that night or not, but we came to the agreement to go back to her place and see what happened.

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 got to her place a little before me and I knocked on the door. She said “hi” in a slightly shy way when I came in. She had just moved into the place and was getting it sorted. We sat down on her couch and talked for a little bit. I was showing off some kind of athleticism to her. She was impressed. We started making out on her couch and eventually made our way to her bedroom. It was very dimly lit and we slowly took each others’ clothes off. She sucked me off for a little bit and I fingered her pussy. She had a nice amount of bush. I asked her why she hadn’t shaved completely and she said, “Hey, I am a woman.” With a laugh. I ended up going down on her and getting her close to cumming. She was a bit too drunk to come at that point. She laid back and I put on a condom and we started fucking in a number of different positions. I slowly put 1 finger in her ass while she was on top. This led to me putting another one in her ass and giving her a pseudo double penetration with my cock and fingers. She eventually got off of me and we started to 69. It felt incredible how she used her tongue on top of me while playing with my balls and asshole with her hands. She wanted me to cum as I was squirming a bit. She laid back down and open her mouth while I shot my load into her gaping mouth. Her moan when I came was fucking hot and she licked up all of my cum off her fingers. After that we cuddled for a while while I played with her pussy and eventually ended up fingering her pussy and ass at the same time. She brought out some lube and told me fuck her ass. I put another condom on and put some lube on her asshole and fucked her ass in missionary while she played with her clit. I was very overly stimulated by this point and was getting near exhaustion. She eventually got on top of me and I continued to fuck her ass. She told me to cum in her ass with the condom. I tried, but eventually had to fake an orgasm in the condom because I was so tired and felt like my dick was going numb. We probably fucked and fooled around for about four hours. It was late after it was over, but I went home and didn’t stay the night. It was great fun.

Did you have an orgasm? Did your partner(s)? I did once. She had one, too. She wanted to have more, but was too drunk to have more she told me.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I wore condoms.

What were your REASONS for having this hookup? We never officially went out on any dates, but as the conversations in those meet ups turned to sex we both realized that we had high sexual appetites and we should do it.

Were alcohol or drugs involved? If so, how much? A few drinks on both sides. I think she felt drunker than me, I could still perform, but at my full capacity.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We both had fun. I received a note from her on Facebook a few days later thanking me and telling me how dirty I was and that it was a thrill. I suggested we do it again sometime. We hooked up again about a week later, sober. Not a last dirty, but a lot of fun. I tried to continue the hook ups, but she put an end to it to keep the word quiet amongst our circle of friends.

To whom did you talk about the hookup? How did they react? No one.

Was this a consensual and/or wanted experience for you? For your partner? It was consensual and we both enjoyed it.

Do you regret this hookup? If so, why? I only regret that I didn’t pursue it further. I felt I was too arrogant afterwards and fucked up what could have been a nice friendship even without the sex.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It was great sexual chemistry. It was hot, dirty, nasty, and very kinky. I hadn’t met a woman who was as kinky as me and was impressed by her abilities sexually.

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

All things considered, how NEGATIVE was this experience? A little negative

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