What’s your gender? Man
How old are you? 27
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: Some college (not currently in college)
What’s your occupation? contractor
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
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)? 15-20
How many hookup stories have you here posted before? 2

I Won the Bet!

How long ago did this hookup happen? 2 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For 1 to 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? J was a sexy little blondie. She was a mutual friend of ours. At the time I had 2 close friends and we all hung out with J. She was had a tight little ass and a pretty decent rack for a small girl, maybe a 34B, but she was hot and she didn’t leave much to the imagination how she dressed. Short little dresses and skin-tight leggings were her usual wear. Secretly me and my 2 buddies were all trying to get with her, but so far none of us had been successful. We started hanging out alone a lot, but nothing sexual ever happened. I was very shy at first and she would usually talk about her job and her family a lot but that was it.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One night we were texting and she sent me a picture of a bubble bath. She said she was going to hop in because she had a long day. I jokingly texted back saying something to the tune of, “you should take a pic with you in the tub and send it to me.” She blew it off and we went back to small talk. She asked if I wanted to come over and watch some TV. I suggested she come over my place seeing as she lived with her mom and I had my own place. She agreed and I went over to get her. When we got over my place we sat on the couch and watched TV. Pathetically I could not make a move on her, although I knew she wanted to fuck. We literally watched TV for 3 hours before I suggested I take her home before we did something we might regret. I got up from my couch and sat on my bed to put my shoes back on. She pretty much jumped on me saying how bad she wanted a back massage. I started massaging her back and she started moaning quietly. I kept on doing this until I knew there was no turning back, then I picked her head up and kissed her.

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? From that point on it was on!! We made out for a while as we both got naked. She went down and took my cock out of my boxers and started blowing me. She gave a great blowjob. She then climbed up on me and started riding my dick. It was some intense fucking! We were kissing the whole time and she began to grind on me really hard, making her cum. I then flipped her over and we fucked missionary for a little while. I usually cum pretty quick when I hit new pussy, but with J I felt comfortable and was able to pace myself quite nicely. She told me she wanted me to fuck her doggystyle, which I happily agreed to, and flipped her over. Doggystyle is my go to position for cumming so in no time I was asking her where she wanted me to cum. She looked back at me and said she wanted it in her mouth. That was all I needed to hear and immediately pulled out and started cumming on her face. She licked up every drop from around her mouth and swallowed it with pleasure. We laid there for a little while catching our breath and then started to laugh at what just happened. We both got dressed and I took her home.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? We kept fucking and still do to this day. She is my wife.

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

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

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

How would you best summarize people’s reactions about this hookup? Relatively positive

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