by Hot Tomale
What’s your gender? Woman
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Decline to state
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 30ish
How many hookup stories have you here posted before? 0
How long ago did this hookup happen? Decades ago
What was your relationship status at the time? Dating casually
How would you best classify this hookup? Friends-with-benefits
How long did you know the person before this hookup? For 1 to 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? I had multiple partners/boyfriends in college. One weekend S, who’d I’d just begun seeing, invited me to his parents’ vacation condo in SanDiego with the intention of hanging out, seeing the sights, and going to Tijuana. S was one of these nice guy types who was in way over his head with me. He used to pick me up, take me out for dinner or a movie, maybe we’d smoke a little pot, then he’d be content with a kiss good night. I only went out with him cause I was bored and I liked his long curly blonde hair. Other than attending the same college, we had so little in common and zero chemistry. We had sex once in his room while his parents were out and it was so boring–said he didn’t like to perform oral sex. Omg. Really? Ugh. I knew his days would be numbered–as I could never cum from just PIV sex. So we’d been seeing each about two weeks when he suggested this San Diego trip. I mentioned the trip to my friend P (who was a buddy I’d fucked on occasion, and he said he and his cousin were heading to Tijuana for the weekend too, and did I think it would be ok for him and the cousin to crash at Ps place Saturday night? I somehow sprang this plan on S at the last minute that my friend P was in town and would it be ok if “my friend who is a really great guy and close friend of mine” could spend the night. Being the total pushover with no boundaries that he was, S said yes–reluctantly.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After a long day in Tijuana, dinner and plenty of drinks by the condo pool/jacuzzi/BBQ, P and his cousin finally arrived and S and I. They were so grateful to have a place to crash for the night, and graciously got everyone good and stoned back in the condo. By midnight S was wasted and went to bed. There was just one bathroom in this place, so as I was washing up/brushing my teeth, P knocked on the bathroom door. I was wearing something that passed for a college girl’s sexy, sheer nightgown, no panties, and he raised his eyebrows liking what he Saw.
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 pulled P into the bathroom quickly and locked the door. We started giggling and whispering about how great the evening had worked out. “Do you like this guy?” p asked. I shook my head, no and suddenly P and I were kissing and sucking each other’s tongues. He cupped my breasts, started kissing my neck. I grabbed his erection through his jeans, and very quickly it was on, his pants were down, my nightgown was hiked up I hoisted one leg up on the toilet seat and helped him guide his rock hard cock into my vagina. We jack rabbit fucked that way for a minute or two until he spun me around and finished in me doggie style a few seconds later, which I loved. We kissed and laughed some more before I quietly opened the bathroom door and shoved him back out. A couple of minutes later I had to crawl into bed with S. I was already thinking of excuses for why I couldn’t fuck him if he made the move, and to my grateful surprise he was passed out, but groggily asked me why it took so long for me to come to bed. I could not believe I had another guys semen leaking out of my vagina while I was spooning another guy. I went to sleep smiling at how absolutely rotten I was.
How sexually satisfying was this hookup? Somewhat
Did you have an orgasm? No, not even close
Did your partner have an orgasm? Yes, one
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? I felt two things at once. Delightfully naughty and guilty for using S. Broke up with him about a week later. P and I were cool and had no emotional attachments to each other. We were really meant to be just friends–but we’d crossed the line on occasion (more on that I another post). Eventually we lost touch with each other.
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, Intoxication, Power / Dominance, Just happened, I don’t know why, just went along with it
How intoxicated were you? A little tipsy/high
What substances did you consume? Alcohol, Marijuana, hashish
How intoxicated was your partner? A little tipsy/high
What substances did your partner(s) consume? Alcohol, Marijuana, hashish
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? My best friend — we did this stuff all the time. Always shared the details.
How would you best summarize people’s reactions about this hookup? Relatively positive
Did you get emotionally hurt as a result of this hookup? A little bit
Did your partner get emotionally hurt as a result of this hookup? A little bit
Do you regret this hookup? A little bit
Why do you regret this hookup? Showed very poor judgment. Kinda mean, Effed up thing to do.
What was the BEST thing about this hookup? The secrecy, verboten nature of it.
What was the WORST thing about this hookup? Being a selfish pig with no impulse control.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No
All things considered, how POSITIVE was this experience? A little positive
What do you think about the Casual Sex Project? Love it
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