A Chance Reunion


This post is sponsored by The T Bar.


What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Seattle, Washington
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Writer
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 60+
How many hookup stories have you here posted before? This is my First

A Chance Reunion

How long ago did this hookup happen? Four Months

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Short fling

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? Jess and I went to grade school all through High School together. She is a short, fit brunette with a nice pair of D cups. Like me she is in her thirties. I hadn’t seen her in many years. We may have hooked up before but I am not sure (I will explain below). I chanced meeting her out jogging one morning while I was back home visiting my parents. I thought she was cute and had an instant attraction to her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? As I said above I had gone to school with Jess all through grade school and on and she grew up only a short walk from my parent’s house. She had never been on my radar then, Jess had been an outsider hippy girl in school. However I can remember at a community event in Junior High making an effort to get a peek down her shirt. I got a good look at her boobs then.
A few months back I had gone home to help out with my Dad after he had heart surgery. I was not in a good place for the first few days of the visit. I went jogging and passed Jess, and thought she was very hot in a tight tank top and shorts and she knew I was checking her out. I passed her again down by a store and we started talking and it took us a bit to realize we knew each other as it had been a lot of years since we had seen each other.
Jess was pretty flirty and she admitted she was enjoying the attention and we ended up exchanging numbers. We ended up texting back and forth all day most of it pretty flirty and some if it dirty. She finally asked if she could come over late.

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 was staying in my parent’s trailer so I said yes and ironically enough their old trailer was where I used to take girls in high school. We were both pretty horny but Jess wanted a bit of foreplay so we started making out and her top came off quick. Clothes came off and I admired her body. I started sucking on her breasts and she was moaning as I thrust into her. We both came and then laid next to each other.
We talked for a bit and asked about each other’s ink. It turned out we were both back home for sick parents. We also tried to figure out if we had hooked up in High school or not. We were both at a lot of the same parties and back then both quite promiscuous and there was a lot of alcohol involved so it was very possible we hooked up at a party or something and don’t remember. We talked until we fell asleep.
I woke up during the night to Jess poking at me. She then mounted me and bounced up and down until we both came again. We didn’t use protection for this encounter which was a bit foolish. It ended when she snuck back to her parents early.

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? I was home for theree weeks and Jess and i edned up having sex almost every night and a few times during the day, mostly in the trailer. The whole thing was pretty fun. When i went back home we decided to end it, as we had both tired long distance in the past and were not fans of doing so again. I woudl have liked to persue things with Jess further but unless we are both back home agian at the same time i don;t think that will happen.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, To cheer myself up, I was feeling lonely, Boredom, It was easy / convenient, Really was no reason not to

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? Havn’t told anyone

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? A little bit

Did your partner get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The sex was really good and she was there when i needed it

What was the WORST thing about this hookup? That i didn;t get t persue anyhting with Jess beyond a short fling

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not at all really, other than it made me think i may want a relationship again after being single a while

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

All things considered, how NEGATIVE was this experience? A little 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? Sex is a big part of my life and is something i enjoy very much. I will share a bit more with my next post.

What do you think about the Casual Sex Project? It’s interesting.

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