College Girl in New York

by Hamilton

What’s your gender? Man
How old are you? 51
What’s your race/ethnicity? White / Caucasian
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 occupation? Executive
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)? 20
How many hookup stories have you here posted before? 0

College Girl in New York

How long ago did this hookup happen? 2 years

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

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

How long did you know the person before this hookup? Just met that day

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 was a young Asian woman. I didn’t know her at all. I saw her in the park and thought she was cute.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was riding my bike home from work in Nee York City and since my wife and kids were away I was in no rush. I stopped at Columbus Circle and sat at the fountain and was enjoying the sunset and watching people walk by and some guys juggling a ball.

I became aware of a cute Asian girl who was sitting on the other side of the fountain who was also watching the people and I could feel like she was looking at me. There seemed like a connection. So I got up and moved closer to her. Not too close that it would seem forward, but close enough to make a comment.

I said something innocuous to her and she responded enthusiastically and we started talking. We didn’t share names or any specifics about our lives like where we worked. I didn’t mention I had a family. We talked about the night and life in NYC. She did say she was a law student and was doing a summer internship.

After sitting here a long time we decided to walk north. We walked over to see the fountain at Lincoln Center and I could tell that underneath the conservative law student there was a bit of wild behavior. I told her I loved discovering things in the city. She looked at me in a suggestive way and said: “Surprise me.” It was clearly a challenge.

So I took her on a quick run around – to an amazing park and a fancy bar near Lincoln Center and then a hip bar in Harlem. We ended up near where we both live. I walked her home.

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? Outside her apartment building she hesitated. She said she she wasn’t sure she should let me up because I could be a murderer. She didn’t know me at all. I tried to calm those fears and said – “we don’t have to do anything.” This is where I realized I knew nothing about women because she said “are you kidding, the only reason I would have you come up is to have sex.”

In the end I persuaded her. Her apartment was a small one bedroom. It was awkward. I’d never had an anoymous one night stand so I was a bit stiff. But we went over to the bed and sat down. She asked me if I had s condom. I didn’t. She groaned. “No condom no sex”. But she searched a drawer and found one.

We started kissing and I undid her shirt and started sucking her tits. And they were wonderfully perky and soft. At this point I was very aware that I was about 50 and she was probably 25. I’d never been with such a young woman and I’d forgotten what 25 year old breasts are like. I sucked her and she moaned. I went very slowly and then she got frustrated and reached down and put my hand between her legs.

At first I massaged her over her dress and then slid my fingers inside her. She was so wet and warm. She had public hair which I like and she started to grind against me. And I pressed harder until she came. She had a wonderfully tight and wet pussy.

At that moment she was mostly naked and I was still dressed she suddenly sat up in bed. She looked at me in the semi-darkness and said: “I’m not feeling it.” And before I could say anything she got up and started getting dressed. It was over. So I got up and left.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? No, not even close

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 was sort of relieved. I had gotten myself into an odd situation where I was being unfaithful and I didn’t even know the person at all. It was totally random. But also disappointed to have taken that risk and then not had sex. And I felt like somehow if failed to please her.

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, Learning new things, experimenting, Thought it was an important experience to have

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

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

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

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Being with a young woman. Realizing I could pick up girls. I felt more confident.

What was the WORST thing about this hookup? Nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It’s made me more aware of casual sex and that people do it. I was shocked when she said she wanted me to come up to have sex. It made me more aware of women’s desires.

All things considered, how POSITIVE was this experience? A little 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 think it should be more accepted

What do you think about the Casual Sex Project? Fascinating

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