Trip Chaperone



What’s your gender? Man
How old are you? 33
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Sports Coach
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 8
How many hookup stories have you here posted before? 0

Trip Chaperone

How long ago did this hookup happen? 6 Years

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 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? Short. Dyed Red hair. Very tight body and nice tits. I was a chaperone on a college ski trip and she was there with her boyfriend and friend. She was crazy hot to me. She didn’t flaunt a lot but she was quite the flirt.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After the trip I led she immediately messaged me on Facebook. And soon enough the dirty texts started. She broke up with her boyfriend and met up with me a week later.

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 got about halfway through making dinner for her when she jumped me in the kitchen. I eventually pinned her to the wall and started pinching her nipples as we were making out. It drove her wild. We eventually made it to the bed where she ripped my clothes off and started sucking me off. This was quite a blowjob. To this day she was the best I’ve ever had. She was determined to get the cum from my body and sure enough, she did. Then I decided to return the favor. She took all her clothes off and I went back to her nipples with my mouth. She was thrashing on the bed as nipple play just sent her into another dimension. Eventually, I started working my way down and started eating her out. She took about 8 seconds to cum. Full body convulsing. By this time my body was ready for round two. I was not missing this chance to fuck her. Now I do not have some crazy massive dick or anything I’d consider my self average at best. But I didn’t notice as I was eating her out she had a VERY small vagina. I went to put myself in her and it felt like I was in her ass it was so tight. She screamed in pain immediately. I felt awful as I had never thought my dick could do that. But she gathered herself and said to go slow at first. So I took my time and we started working towards a good pace. It felt incredible. She started getting back into it and I flipped her over to my favorite position on her side. I immediately started to go at maximum pace. She begged me to smack her ass and as I did I felt her just explode with an orgasm. I could feel her throbbing and that was the most I could give as I pumped into her what my body had left.

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 stayed the night and went home in the morning. We briefly dated (and fucked a lot). There was a brief thought of trying to get very serious but I was 8 years older than her and just in a different stage of life. We remained friends for a while until I started dating my now wife. Then I decided that I needed to stop the friendship. But no regrets.

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? 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? 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 immediate group of friends. They cheered it. It was very out of character for me.

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The passion and energy were outstanding.

What was the WORST thing about this hookup? Almost breaking her and knowing that it probably couldn’t go anywhere.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Showed me I could have a more wild side.

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

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

Anything else you want to add about this hookup? Don’t be afraid to put yourself out there. You can be rewarded.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? This was basically it for me. I was always a more committed person and it suits me well. It’s made me a better husband in the end.

What do you think about the Casual Sex Project? Fascinating. Really cool idea.

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