This post is sponsored by The T Bar.


What’s your gender? Man
How old are you? 44
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? finance
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 0

High School Reunion

How long ago did this hookup happen? long time

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

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 was a year behind her in high school. We weren’t particularly close then, but we hung out with overlapping crowds. She was a little bit of a hippie and had big brown eyes and sandy brown-blond hair. Slim and bronze. I liked her and she liked me, but there wasn’t much more than that when we were in high school. She was really good looking, and I kinda had my pick of the girls then, but was a slow starter.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Fast forward a couple years. She and I are going to different colleges in a midwest city, and she’s working at a bar that I happen to hit with some friends. I see her and it was like long lost friends reunited. My buddies are impressed I know a girl this hot. And since our high school was small, she gives me a big hug and kiss on the cheek. She brings us a few pitchers of beer, we play a little pool, and she and I break off to catch up and chat a bit. It’s a quiet local bar, and after about midnight my crew starts to break off while we’re playing catch up at the bar. Finally all the other patrons go home and it’s just my crew. I suggest to my guys that we go back to one of my buddies pads for after-party. They all bundle up and head out the door. Sarah (not real name…sick of writing “she”) asks, “are you leaving, too” with a look in her face that says more than any words can. It’s on. I shout to my crew, “I’ll meet you there.” Ha!

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? Sarah and I skip the after-party and go back to my place, which is nearby. We plant ourselves on the couch and turn some music on and have a beer. Keep in mind, we weren’t very close in high school and have never fooled around with each other. I had had sex with a couple of her friends, but wasn’t sure if she knew that. There was another girl in her class that I dated for awhile, and it was pretty clear to the whole school that we were hitting it. She wasn’t known as an easy girl in high school. In fact, I wasn’t even sure if I knew anyone who slept with her. So we were both a little nervous.

She says something pretty funny and as part of laughing I leave my had on her leg. She put her hand on top of mine. Then we’re kissing, feeling all over each other, and just digging in. As I start unbuttoning her shirt, she suggests we go up to my room. As soon as we walk in the door she takes off her jeans and is standing in front of my bed with a flannel shirt and underwear. I guide her onto the bed and start kissing her slowly from the knees up, which seems to really work for her. I get to her underwear and kiss her over the panties and rub my fingers just beneath. I move my way up to kiss her, keeping my hand down below. Things are working for her. It’s like we’ve done this a thousand times. I get her bra and shirt off as she grabs my cock slipping her hand under my underwear. Her fingers are long and thin and feel great as she wraps them around me. We rub each other for awhile. I’m thinking about going down on her (haven’t done a ton of that at this point…and kinda wondering if she’ll go first), then she says, “Let’s do it.” Her pussy is feeling great in my fingers at this point. I really want to go down on her, but she asks me again to get it going. I get up and grab a condom and put it on. We start in missionary, slow and steady. I’m trying to figure out how deep, how fast. I’m a tish big for her, so I roll her on top to let her control things. We fuck like that for awhile until she wants a change up, so I go back on top now knowing where her strikezone is. We do it like that for another few minutes and she’s relaxing and enjoying this. We just get into a zone and it seems like she’s getting close. I don’t want to fuck it up, so I just keep going as is. It takes a little while…she keeps pushing her hand in my back as if to say don’t change anything…so I don’t. After a few minutes like that she comes. Relieved I didn’t “win”, I move her on her stomach and start going for the finish line. I fuck her for a little bit like that and toward the end I pull her ass up more toward doggy and come shortly after. Nice satisfying lovely sex. It’s late and we’re tired. We roll over and fall asleep.

The next morning, we wake up naked and in each other’s arms. We’re both a tish hung over, but we pick up thing right where they left off. My hand finds her pussy and starts massaging slowly. She reaches back and grabs me and starts stroking. Things are getting hot fast. There’s staying for breakfast, then there’s breakfast in bed. In no time, I’m am fully hard. There’s only one thing next, so I roll out of bed to grab another condom, and she says, “No, let’s just do it.” She knows I’m not a big player, and I know she’s not either, so we’re both comfortable from that standpoint. She says she’s on the pill, so I don’t get up. We spoon and do it that way for most of the time. Slow, sleepy morning sex. I reach around and use my hands. Things build. I’m getting to a point where I roll her on her stomach. I have my hand on her clit as we both come within seconds of each other. We gasp, laugh, and breath deeply as I roll off. We laid there in bed chatting and joking about why it took so long.

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? It was just, “nice.” There was no awkward goodbye. We didn’t want a relationship, and just went back to our own ways. Different schools, etc. Soon thereafter, I met a new girl and started getting on with her. Life just took us in separate directions, just like it took us together that night. About five years later, I ran into Sarah at a high school reunion and she’s there with her fiancee, a dude I went to college with. It was little awkward. Sarah and I mainly just smiled, flirted a little bit, and remembered a fun night together. I got the sense he knew about us, so I didn’t hang around them too long.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Condoms, Birth control pill / patch / ring / injection / implant

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

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

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? Not at all

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? A couple of high school friends. They were very positive.

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 randomness of it. I hadn’t seen her for a few years, and that seemed to provide the kindling.

What was the WORST thing about this hookup? I just felt a little bad not using a condom in the morning, but she asked me to go.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It was my first casual hookup, and it was great. It did teach me that I’m more comfortable have sex with women I’ve known for awhile. There was more about Sarah than her looks that I liked. She was a good person, funny and nice. I’m not sure I could just fuck some hot girl I met at a bar.

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

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

Anything else you want to add about this hookup? I was kind of surprised we never hooked up again. When I saw her again at the reunion, there was a little sadness in both of us that we never pursued things further.

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 have to like the woman. I’ve had opportunities to fuck hot women that I considered horrible people, and I couldn’t bring myself to do it. That said, I’ve had very nice women ask me to sleep together and if I’m not attracted I just can’t do it.

What do you think about the Casual Sex Project? It’s interesting. I’m not sure why I decided to share this story, and I’m not sure what it will be used for, but oh well. I think people need to be more open and comfortable talking about sex. Being closed off about sex only creates guilt and shame, which should have nothing to do with sex. So there.

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