Snowed in with a Dinner Date



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? Chicago
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
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)? 15
How many hookup stories have you here posted before? 0

Snowed in with a Dinner Date

How long ago did this hookup happen? 8 years

What was your relationship status at the time? Single

How would you best classify this hookup? Sex with an ex

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? She, we’ll call her Ann, was a college cuddle partner of mine. Ann was athletic, bi-racial, brilliant, and just kind of cool. I always looked up to how smart and ambitious she was. I don’t think we ever had sex in college, but we made out a bunch my first year. She was several years older than me, and we probably only spent a handful of nights together, mostly PG-13 stuff. Back then, we were both pretty inexperienced and innocent. We kept in touch only loosely after she graduated: a few text messages and then, every now and then, a handwritten letter. Before this story, I doubt that I’d heard from her in a full year or more, and I think both of us had changed our phone numbers.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was in graduate school, studying late on a cold January night in Chicago. I got a text message from an unknown number asking if it was my phone number. I said it was and was surprised to learn it was Ann. She said that she was coming back to Chicago to visit friends (turns out she’d moved away from the city just before I moved there). She found out through a friend of a friend that I was there and in graduate school and got my number. Over a quick text conversation, we made plans to meet up when she was in town, later that week. I was trying to save money, and am able to cook a halfway decent meal, so I suggested that I could make us dinner and then we could go to a neighborhood bar. She agreed. It was a school night, so I didn’t want to “go out” for a bacchanal. In any event, I cleaned my little apartment and cooked up a nice meal, probably intentionally drank a couple beers in the process to loosen myself up, socially. She arrived by taxi in a driving snowstorm with a bottle of wine. It was great to see her. I couldn’t wipe my smile off my face as we got caught up on the last few years.

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? The hookup was a play in two acts. First, we had dinner, then we flopped on my cheap futon and split a bottle of wine. It was snowing pretty hard, so we decided to just stay in rather than tromp out to a bar. Reverting back to college habits, we eventually started cuddling and kissing a little bit. I slipped my hand under her shirt. By this time, it was well after midnight, and the snow was piling up outside. We decided she’d just stay over and we went to bed. I loaned her an old t-shirt and some gym shorts and we just sort of rolled around and made out until we fell asleep. It felt good to be in such close contact with someone again. It had been six months since I got out of a long relationship.

In the morning, I woke up and made us coffee. I was still planning on going to my morning class, so I woke her up with a mug of coffee and told her she was welcome to stay as long as she liked, and that if she was still around when I got back from class, we could go to a museum or something. She said that she should probably get going, too, so was just sat on the futon and sipped our coffee, both enjoying what I assumed would be the last few minutes of our time together. Then, we kissed, but with a new kind of energy. It was on: this time in a raw, sexual way that we’d never done before with each other. Soon, I was carrying her back into my bedroom with her legs wrapped around my waist. She’d taken her (my) t-shirt off and I laid her on the bed and pulled down the gym shorts. She was fully shaved, and I ate her out with one of my hands massaging her from inside her pussy and the other stroking her breasts. She came with both of her hands clutching my hair. Then she pushed me onto my back, pulled her hair up with a band, kissed me, and started giving me head, pausing occasionally to laugh and smile. I asked her whether she wanted me to cum in her mouth, and she said that I could if I wanted to, but if I had any condoms around she wanted me to fuck her. Truth be told, I might have rather cum in her mouth because it was amazing, but I did have some condoms, and I’d never fucked her before, so I put one on and we fucked missionary. She liked it a little rougher than I’m used to, but I did my best to respond to her signals. I remember looking at her beautiful, cinnamon-colored skin and her face with her mouth agape as I came inside of her. I tried to pull out before going flaccid, but she wouldn’t let me. Eventually, I think the cum just leaked out of the condom while I was inside her. She said not to worry. She is smarter than me so I didn’t worry.

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 missed my class. We both showered and got dressed, and then I walked her to the L. We were comfortable with one another, but I could tell she was feeling guilty because – as it turned out – she had a boyfriend. That hadn’t really come up before, and if it did, I assumed she was smarter than me so I wasn’t about to second-guess her choices. She eventually reunited with her friends in a different part of the city. We had another drink before she left town, but I didn’t feel guilty about our hookup because she hadn’t really disclosed her relationship status, and I wasn’t about to take on any guilt for hooking up with her after I learned that she was in a tricky spot. I didn’t think any less of her for cheating. Maybe she needed it in some way. I felt good to break the dry spell. Human connection is important! She texted me a year later to say she was coming back to Chicago, but I was out of town and was starting to see someone so it was for the best that we didn’t meet up. The last time I saw her, I was kissing her with the taste of her still on my lips as she boarded an L train on a bright winter morning. Not a bad way to remember someone.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

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

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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? A few close friends. They knew I was in a dry spell, so they were happy 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? It was fun, sexy, unexpected, and snapped a long dry spell for me. I was single so it was guilt-free, fun.

What was the WORST thing about this hookup? I wondered whether she felt guilty, but my sympathy for her was not vast, because I was not properly briefed on her relationship status.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? A little bit.

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? Old Man Winter gets the assist.

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? There are times in my life when I think it really helped me with my self-confidence. I’ve had other experiences that weren’t nearly as fun or enjoyable as this one. Now I’m in a committed relationship and I don’t really miss it.

What do you think about the Casual Sex Project? It’s nice to read. It feels wholesome in a way that I wouldn’t have predicted, given the premise of the site.

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