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What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Chicago
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
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)? 15
How many hookup stories have you here posted before? 1

Sex In The Afternoon

How long ago did this hookup happen? 10 years

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Friends-with-benefits

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? R was a waitress a a local restaurant, still pursuing her college degree part-time. She was petite, not-quite-curvy, with wild blonde hair, big breasts for her size, had a hippie vibe and a crooked smile, a nose piercing and a belly piercing added to her allure. I met her at a bar, began chatting with her because she was pretty and looked interesting, and we’d hung out a few times since meeting in the bar. We’d gone for a hike and out to dinner once together. This was in a small town and I was new there, so I really appreciated the company. She had a boyfriend in St Louis, and I had a girlfriend who was living in Georgia for grad school. I was planning to move down there a few months later. There was some chemistry but we were both taken. Once, we made out after smoking a joint at her place, but that made things awkward later, so I assumed it wouldn’t happen again.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was a Saturday afternoon and I was sitting on the front porch of my apartment. It was springtime, but chilly Midwestern spring, so I was bundled up. I didn’t have many friends and no internet, so I was drinking wine and reading Hemingway’s Death in the Afternoon.

I got a text from R asking if I was home. I hadn’t seen her in a few weeks, and was pleasantly surprised. I said I was home and already halfway in the bag, reading Hemingway. No response came back, so I kept reading and drinking. Maybe forty five minutes later she came walking up the steps to my top floor porch with a case of Stag Beer under her arm. She was wearing tight jeans and a flowery top that showed some cleavage. She was drinking a can of beer from the pack when she arrived, which was funny.

We sat on the porch together, drinking and talking.

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 was already lonely and drunk and full of Hemingway when she showed up, so things were charged when she arrived. After a while, she said she was cold so we stepped indoors. I had three pieces of furniture to sit on: a bad futon, a bed, and a desk chair.

At some point, we kissed. I could tell she was horny by the way she pushed her hips into me. Things happened fast after that. Her top came off and her boobs spilled out. She unbuttoned my jeans and then we were basically making out with only our undies on.

Now it got real. We collapsed onto the bed and I pulled her panties off. Her pussy was totally shaved and I began to eat her out. She came on my tongue, then got up and grabbed a condom from her purse.

Did you come over here just to fuck me, I asked. Shut up, she said. She put the condom on my stiff rod and rolled it down my shaft with her mouth. Then she pulled me onto her and we started to fuck. We were used to different partners, so it was awkward at first, but we figured it out. We went doggie, and then I laid on my back while fucking her from behind and fingering her until she came again.

I hadn’t come yet, so she took me into the shower and soaped me up. Then, she knelt down and poppped my dick in her mouth. She’d recently acquired a tattoo on her arm, which I found very hot. I watched her tattooed arm pumping me with my dick in her mouth. At one point, she looked up at me, her mouth full, and asked if I was going to cum. That’s all it took; I shot my load into her mouth and she pumped my cock faster with her hand. She kept her mouth on my dick, sucking slowly as all the cum dribbled out. It was so hot that I got hard again a few minutes later, but she had to be somewhere later so she dressed and left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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 was weird between us, and we lost contact a few months later. I think we both felt badly for cheating.

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

What were your motives for this hookup? Fun, pleasure, horniness, Intoxication, I was feeling lonely, Boredom

How intoxicated were you? Drunk/high but not wasted

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? A little bit

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Somewhat

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I told a buddy of mine. He was shocked, then jealous.

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

Did you get emotionally hurt as a result of this hookup? Somewhat

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? A little bit

Why do you regret this hookup? I was cheating.

What was the BEST thing about this hookup? Her blowjob

What was the WORST thing about this hookup? Guilt

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

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