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What’s your gender? Man
How old are you? 34
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? North Carolina
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Retail manager
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
How many sexual partners have you had in your life (including oral sex)? 17
How many hookup stories have you here posted before? 2

First Time Bareback

How long ago did this hookup happen? 15 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than 6 months

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? At the time, I was 19. She was 38, white, average height/weight, blonde hair, 36D tits, and shaved pussy.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Met her in an online chat room. She was married but unsatisfied and lived out of state. We met online every night around the same time and engaged in some raunchy cybersex chatting, occasionally exchanging nude pics and me occasionally sending her videos of me jerking my cock and cumming on her printed pictures.

After about a month, we started planning for her to visit. She told her husband that she had a work seminar and booked herself a hotel suite in a nearby city to help sell the story.

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? When she came to town, I picked her up at the airport and she gave me a long and slow blowjob all the way to the hotel. Once she checked in, we went to the room where we immediately stripped and I started eating her pussy. After she came, I was ready to fuck her, so I grabbed the box of condoms from my bag but she stopped me. She explained that she had only had sex with her husband over the last 15 years and had her tubes tied, so unless I particularly wanted to wear one, I didn’t have to. I tossed the box and shoved my cock in her. 15 minutes later I was pumping cum into her pussy. She was so tight and told me that it had been close to a month since her husband had fucked her.

We spent the entire weekend fucking all over that hotel room…bed, couch, shower, floor, etc. The entire weekend, she only swallowed one load. The rest was shot deep inside her.

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? She went home with a sore pussy full of young cum. We continued cybersex conversations for a few months until I started dating someone.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Emotional intimacy, closeness, connection

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? 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 college roommate. He was pissed because I didn’t invite him.

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? Experienced my first time not having to use a condom without having to worry about STD’s or pregnancy

What was the WORST thing about this hookup? It was only a weekend fling

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

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

What do you think about the Casual Sex Project? It’s an awesome project!

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