by Ian

Gender: Male
Age: 29
Race/ethnicity: White
Current location: Chicago
Highest education received: College degree (eg., BA, BS)
Occupation: Assistant
Relationship status: Attached
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 35
How many hookup stories have you here posted before? 2

She Saw Me on OKCupid

How long ago did this hookup happen? 4 years ago

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…)? One night stand

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? Kathy was a cool girl. I knew her socially from a few places and hung out in the hipster crowd. Very nice. Wasn’t my type, but I was persuaded.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had been on OKCupid looking around for people in town. It was a small one so picking were slim. I saw Kathy on there and our percentage was 99%. I didn’t want to do anything about that because I had met her and while I liked her, she wasn’t my type. We met at a bar that did hipster karaoke on Tuesdays and she began talking to me referencing the OKCupid thing. I didn’t really say much about it, but as the night went on we kept talking and while I could have left at anytime I didn’t. We eventually ended up making out in front of the bar after closing and I told her that I wasn’t a relationship kind of a guy, but was good for hooking up. I followed her back to her house and we went 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? We went to her bedroom and I stripped her down. I kept my clothes on for a longer time for some reason. I played with her pussy and slightly kissed it. I played with her asshole for a little bit, too. She stripped me down and have me a blowjob. While we were rolling around I laid back and lifted my legs ups and asked her if she was into that and she said yes and started licking my ass. She got me very turned on and began to put her finger in my ass which almost made me come. I told her to tongue fuck my ass and she deeply put her tongue in my ass for the next little while. I then flipped her over and spanked her ass hard. She liked it. I rolled her over and out my hand around her neck as I fucked her in missionary. I was in total physical control and she loved it. I turned her over to fuck doggy style and and fucked her hard and deep while I spread her ass cheeks apart and spanked her until her ass became red and slightly bruised. I rolled her over and tit fucked her nice tits as she sucked me off with each thrust. I laid back down as she licked my asshole again and stroked my cock off. I shot a huge load of cum into her mouth and she swallowed. We both cuddled and fell asleep after a vey rough and intense session.

Did you have an orgasm? Did your partner(s)? I had one. She had one as well.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condoms. She also had an IUD.

What were your REASONS for having this hookup? Purely sex and physical attraction.

Were alcohol or drugs involved? If so, how much? Light drinking.

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? She gave me another blowjob after we woke up. I fingered her to an orgasm and I left. She suggested we do it again at some point, but I didn’t want to go there. We were still friendly and even though we don’t talk think we’ll of each other.

To whom did you talk about the hookup? How did they react? I didn’t tell anybody. No need.

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

Do you regret this hookup? If so, why? No regrets.

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? The best part was an incredible rimjob. I have a fetish for it and it’s so hard to find girls that do it and like doing it. This one loved it. She was also a great fuck and had a wonderful sexual presence.

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

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

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