Be Careful What You Ask For

by James in Winston

What’s your gender? Man
How old are you? 33
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: Some college (not currently in college)
What’s your occupation? I.T.
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 25
How many hookup stories have you here posted before? 0

Be careful what you ask for

How long ago did this hookup happen? 2 years ago

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’s about 5’5″, 130 pounds. Blonde, blue-eyed. She was my wife’s best-friend’s sister. I met them at a party at my house. I thought she was very attractive and a bit on the horny side.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The hookup began in the driveway of my house. No planning was involved. I instigated it. We had been watching television and it was late and everyone in the house had crashed. It was my intention to wait out everyone else. She caught me starting at her and suggested we go “outside to smoke a cigarette”.

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? After we went outside, she asked me about my relationship with my wife. I was honest and told her it wasn’t very fulfilling. We started feeling each other up. She began to massage my cock and balls through my jeans. I immediately went for her breasts through the fabric of her shirt.

She turned out to be very “dirty” from a sexual point of view. I was extremely turned on. She dropped there on the driveway and started sucking my cock — right there in the neighborhood. It was around midnight. Anyone looking outside could have seen us.

We decided to fuck, but had to find a place nearby. The only place was on this hill that ran down to a creek in my neighborhood. It would shield us from view.

I took a jacket from my car and folded it over. She laid, belly-down with her hips over the jacket. This boosted her butt up slightly, giving her back a sexy arch. I climbed on top of her from behind and penetrated her. The angle of her body made my penis go insanely deep on the in-stroke. We both reacted to the feeling and the “tightness” of the penetration. I grabbed her hair with one hand and pumped the HELL out of her backside, stroking deeply each time. The engorged head of my penis rearranging her womb on each in-stroke. I grew more swollen with each stroke until I finally jammed it into her balls deep and emptied my nut inside her.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? After the hookup, she suggested we “finish” it by fucking.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Intoxication

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, Marijuana, hashish

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? Didn’t speak with 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? 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 incredible sex we had on numerous occasions

What was the WORST thing about this hookup? That it ended

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No change

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? There was a lot that happened. It would take a few pages to describe

What do you think about the Casual Sex Project? It is interesting. I’ll have to learn more to form a more complete opinion

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