Group Ski Trip



What’s your gender? Man
How old are you? 34
What’s your race/ethnicity? East Asian
What continent do you live on? North America
What country and/or city do you live in? New York
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? In a serious relationship (open)
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Very high sex drive, late bloomer
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? 0

Group Ski trip

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? Friends-with-benefits

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? Up to that point, I had mainly only messed around with girls who had become friends then girlfriends or friends with benefits

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was the end of a long night. V. had driven out that night. I ended up being the last one dropped off as I had parked by her house, which was close to mine. As we bullshitted about nothing in particular, she bemoaned the fact the she hadn’t succeeded in hooking up with someone that night. That would have been the logical time for me to offer my services, but I was trying to get with one of her friends and knew that would destroy my chances.
A few months later, in the winter, a bunch of my friends had rented a ski cabin up north. Folks had brought quite a few bottles of whiskey and vodka. As was our tradition, we commenced getting good and fucked up on night number one. During the course of drinking games, V. and I ended up sitting next to each other. My memory is hazy, but at some point, she casually asked if I had any friends with benefits. We didn’t really have that many chances to continue the conversation, but it must have stuck in my subconscious.

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? Towards the end of the night, as people got drunk, tired, or both, they found places to crash. I’m not sure if V. was in a bedroom and I wandered in next to her or it was the other way around. Details have a tendency to drown and die in copious amounts of whiskey. What I do remember distinctly is feeling her around rubbing my dick through my shorts. I quickly became hard as a rock as she teased me with caresses and strokes. I responded by reaching underneath her shirt and cupping her nice orange-sized breast over her soft silky bra. As my hands wandered down towards her pussy, she whispered to remind me that her friend was sleeping on the floor next to the bed. I responded by stroking her clit through her gym shorts, which made her stop whispering and concentrate on keeping quiet. I could feel the heat of her mound through her shorts. She pushed herself into my hand and grinded. She lifted the waistband of my shorts and started stroking my cock. I slipped my finger into her pussy, but not too deep. I used the moisture on my fingers to start lightly stroking her clit. She gasped into her pillow and squeezed my dick hard.
At this point, she couldn’t focus on giving me a handjob. I alternated between stroking her clit and lightly pressing her g-spot. She kept getting wetter and wetter. Eventually, I went from using one finger to two. I think we were both getting off on trying to keep quiet. Her breathing got deeper and more erratic. I used my right thumb to put pressure on her clit. She moved her hips to make press harder, then let up. I continued using my left fingers to curl up and lightly press her g-spot. My hands were getting pretty wet. Eventually, I felt her shudder and her vagina squeezed my fingers and she came. She laid back for a little while and then whispered into my ear to go to the bathroom. I got up, tip toed to the door, and quietly padded through the now dark and quiet hallway to the bathroom, sat down on the toilet and waited.
She came in about 30 seconds later. It was the first time we had made eye contact in the light since the encounter started. She was flushed and grinning and said something along the lines of “Fuck . I think we were being loud but whatever.”

We made out a bit. She quickly pulled my shorts down. I remember how hot her mouth felt as she took me into it. She was pretty enthusiastic. It felt great when she licked and sucked my balls while stroking me. I told her when I was getting close and expected her to finish me off with her hands. Surprisingly, she sucked harder and faster. It didn’t take too long. I exploded into her mouth. She spit into the toilet and laughed while commenting on how much I had come. She suggested it might be best if we sleep separately after that to avoid people talking shit so I found a spot on the couch downstairs in the living room. She went back to the bedroom.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

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 fine. We remained friends. We didn’t really have a chance to really hook up after that for various reasons. Every once in a while, I’ll think about this incident while rubbing one out. We had fantastic chemistry and I could tell she was a great catch as a girl who was just as horny and into sex as most guys. I fantasize about what we could do with a weekend alone, toys and food.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Intoxication, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol, Marijuana, hashish

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

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? No one. I generally keep all hookups to myself.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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 secretness and randomness.

What was the WORST thing about this hookup? Not being able to fuck like bunnies for a few days.

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? Very positive

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

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? I love it. It’s nowhere near as rewarding as sex with someone you love..for the first few months? years? etc

But i love sex with someone the first few times. It’s exciting and new and generally awesome. I love seeing what turns people on. What their faces look like while you’re hooking up. What they sound like. Whether they’re more playful or dirty than I expected.

What do you think about the Casual Sex Project? Love it. Beats the hell out of purely fictional stories, porn.

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