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What’s your gender? Man
How old are you? 45
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20

Surprise! I Was Just Passing Through.

How long ago did this hookup happen? 20 years

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Sex with an ex

How long did you know the person before this hookup? For more than 3 years

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? My ex-girlfriend and I got together freshman year of college and stayed (with a few breaks) for 5 years. We had that classic high-sexual-chemistry, low-lifetime-compatibility thing. She was extremely smart and witty, but we disagreed about some fundamental stuff that made the relationship volatile. She was, however, very pretty, maybe 5’4″, shoulder length brown hair, 34D with otherwise curvy body that always got me hot and bothered. We fucked like animals: almost every afternoon in college after classes finished for the day. But the emotional rollercoaster finally became too much for me and our breakup was very acrimonious.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She and I were both from the east coast and we went to college on the east coast, and now I was in grad school on the east coast. After our breakup, she moved to the west coast. I hadn’t heard a word from her in 2 to 3 years (primitive email, but no texting in those days).

Then I get a cryptic email saying she was passing through my area on the way from her mom’s (5 hours away) to visit friends in our old college town. Could she stop by for lunch? Sure, I guess. Before texting, it was very difficult to gauge when somebody coming from a long distance would arrive at a certain place, so we would just meet at my shithole apartment and then walk down the hill to lunch. She arrived, looking like she’d just been in the car for 5 hours, but smiling, wearing a tight, white t-shirt and one of those red bandana kerchiefs on her head. She looked like a sexy farmer’s daughter.

My apartment really was a shithole, almost no wall hangings, no TV, a dusty kitchen table with no chairs and covered in stray unopened mail and paper. She had great decorating taste, so she started giving me shit and laughing at her own comments, which made me a little annoyed but I knew she was just trying to bust my balls. She was a bit sweaty, so I gave her a bottle of water and we sat next to each other on an old couch, doing the “how is [person]?” for 10 minutes. I must not have been getting the hint, because she laid down, the back of her head on my lap, facing up, telling me some story about the beauty of the west coast. Somehow, I still wasn’t getting the hint, and so finally she just pulled my head down until our lips met.

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 kissed, just-lips, passionately, on the couch for a full 5 minutes. I cupped my hands beneath her head and we evidently competed as to how deep in each other’s mouths we could reach our tongues. She grew impatient so she lifted her tight t-shirt a bit, and guided my hand onto her bra. Honestly, it sounded so dippy in retrospect, but I didn’t know I was getting laid until that moment. She knew I worshiped her big tits, and she giggled, saying “You like friends, don’t you?” I said, with exaggerated dryness, “Yes. Yes, I do.” She rolled and put her feet on the floor; she grabbed my hand and led me to my “bed,” which was just a cheap futon.

I whispered sheepishly, “Condoms?” But she just said no because she was still on the pill. She took my pants and boxers off, revealing my rock hard-on, but instead of going down or rubbing it, she just got down to business by pushing me back on to the bed and straddling me. Keeping her t-shirt on, she unhooked her bra behind her back. Then she pulled the move she knew, taking off a t-shirt in a single, cross-armed motion, causing her gorgeous big natural tits to fall out. That was when my hard-on went to 11. Her kerchief fell off, and notwithstanding my suggestion to keep it on (with the unspoken desire to keep my farmer’s daughter fantasy going), she ignored me. This was for the best later, as I knew her like getting her hair pulled. I pulled her down and sucked and kissed her tits while she giggled and her hair fell over my face.

She stood up to drop her bottoms, while I took off my t-shirt, and she got on top of me, guiding my hard dick into her familiar and yet somehow only distantly familiar pussy. She was wet and it slipped right in; she gasped. She rode me furiously, first propping herself up with her arms, then prone tits-to-chest and mouth-to-mouth, until she orgasmed volcanically, practically busting my eardrum. She laughed and pretended to administer first aid by wrapping my shirt around my head like a bandage. I didn’t tell her my back hurt because my futon was so cheap and uncomfortable.

I fucked her doggy and pulled her hair until she came again. She collapsed onto her back and just said, “Your turn.” I got on top and pounded her pussy while making out with her, until she closed her mouth, looked me in the eyes, and said mischievously, “You want to cum in me, naughty boy?” That was it and I felt my balls and lungs empty all at once. I spasmed at each spurt filling her pussy, almost like I was holding a downed power line.

After 10 minutes of lying together on our backs, repeating variations on, “Oh my god,” and “That was awesome,” she mounted me again until she came, and I got on top of her and fucked her furiously until I came inside her again. I joked, “This sucked. I wanted to cum on your tits,” but she just said,”Next time.” (Spoiler alert: There was no next time.)

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? We did go to lunch after all, at a bagel sandwich place. Mostly giggling, with some anticlimactic mundane conversation about what time she had to meet her friends in our college town or whether we should stop for some bottled water for the rest of her trip. Feeling hurried, she jumped in her car, rolling down the window, and we shared a sweet, long, loving kiss.

She drove away. I never heard another word from her for 9 years.

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

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

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? Not at all

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? 2 to 3 of my grad school friends, but not until months later. They laughed riotously and said they were to print rock concert t-shirts saying “Reunion Tour ’98.”

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? The mind-blowing sex, amplified by the surprise.

What was the WORST thing about this hookup? Wondering if we could ever have made a longer relationship work, but knowing it would not.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I got a laugh about having been used for sex. That had never happened to me before.

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

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

Anything else you want to add about this hookup? I jerked off to the memory of this for many, many years. Occasionally now, even.

What do you think about the Casual Sex Project? Half therapeutic confessional, half fap material.

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