Weekend Fling

by CD24

What’s your gender? Man
How old are you? 40
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? Television
What’s your current relationship status? Single
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)? 4
How many hookup stories have you here posted before? 0

Weekend Fling

How long ago did this hookup happen? 1 month

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 less than 6 months

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 19, black, about 5’4, 150, long dark hair, nice dark eyes, really big breasts. We met on an erotic chat site and just kept up our conversation over a 3-month stretch. She lived a 2 1/2-hour plane ride away so I made the trip to meet up with her knowing full well exactly why we were meeting.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Plenty of planning involved because we both had difficult schedules to work around. I’d say the instigation was mutual. I booked a hotel in her town, picked her up, and took her there for the weekend. The lead-up to it was many nights of steamy sex chat as well as normal real-world chat.

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? We had sex numerous times throughout the weekend. Every hole of hers got filled at one point or another. She had a strong daddy fetish so we played that a lot during our time together. She was pretty inexperienced, having only ever been with one other guy so we could really only do one position but she took it very well and she got into it a lot. For someone inexperienced, she did very well. Our talks were much the same as they were online – the real-time experience matched the online experience, which is a rarity. It ended at the end of the weekend with me flying back home. We continue to talk and hope that we can meet up again sooner rather than later.

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? Both of us are totally comfortable about what we did. Definitely no regrets. We both needed the release. Future-wise, if it happens again, great. If not, I’m fine with that too. Given the distance and the age difference, multiple meetings are very unlikely. I certainly feel like I gained a person whom I can have sex with whenever we’re around each other. But as far as anything more than that in the future, I just don’t see it.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, I was feeling lonely

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? Have only told other ‘online’ friends and they were ecstatic about it as I’ve constantly heard about their experiences and I haven’t had many to share with them.

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? How she reacted to what I was doing to her body both with my cock and with my tongue and fingers.

What was the WORST thing about this hookup? Couldn’t try more than one position because of how tight she was. It’s a very minor complaint, though.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not at all

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 don’t think anything should change. If you can get it, get it…just be careful about it. You can have a lot of fun with it provided you play it responsibly.

What do you think about the Casual Sex Project? Had never heard of it until seeing something about it on a sports website of all places. Interesting concept and I think it’s good to have open discussions about it.

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