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What’s your gender? Man
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: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Engaged/Married (open)
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 2

Another Conference Hookup

How long ago did this hookup happen? 2 months

What was your relationship status at the time? In a relationship (open)

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 nice looking MILF type with very sexy long brown hair and obviously looking for a hookup that night.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was at a conference and knew there was a high-end restaurant close by known for being a cougar bar. The food is very good and the scenery better so I figured I’d go for a few drinks and see what happened.

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?

I sat at the bar and ordered a drink with an appetizer. It was very crowded with females outnumbering males nearly 2:1. I figured if I played my cards right, it could be a fun evening. As I was finishing my food, I ordered another drink, and she sat down next to me and ordered a white wine. I told the bartender to put it on my tab which is usually a good icebreaker.

She was wearing a business skirt and heels with a blazer and blouse. Obviously, she was looking for something that night since she had more than one button undone so that I could see that she wasn’t wearing a bra. We made some small talk which gradually became more flirty and sexual. I found out she was recently out of a long monogamous relationship and was “sewing her oats.” While at the bar she was turned towards me and I got a much better look at her body. She was well put together with great legs which she made sure she playfully crossed and uncrossed many times making sure I saw what she had. She then asked where I was staying and found out it was a nice 5-star hotel not far from there. She asked me if I’d like to spend some private time with her and of course, I said yes. Since we had both been drinking, I suggested we Uber to the hotel and leave her car. She wasn’t up for that, but I had less than her so I suggested we drive her car there but I’d drive since she was pretty tipsy. The hotel was less than 10 minutes away, and we arrived safely.

We went to my suite, and I asked her if she’d like something else to drink from the minibar which she happily accepted. We sat on the couch and talked for a bit while having our drinks. She excused herself to the restroom for a moment and said she’d be right back since she had to call a friend to check in and say she was ok. A few minutes passed, and she came back to the couch and straddled me. She began kissing me, and she was great at it. She took my hand and slipped inside her blouse where I began playfully massaging her enhanced breasts.

At that point, she got off of me and went to her knees, undid my belt and pulled off my slacks. She began one of the sluttiest blowjobs I ever had. She was obviously experienced, and it was straight out of a movie. She moaned forever and had no gag reflex, all the while looking up at me. I complimented her on her skills which she smiled. I think she knew how good she was.

She stood up and without removing her heels or skirt, but rather pulling her skirt up, she straddled me and began rubbing her soaking shaved pussy on my cock. I told her how great that felt and at which point she said she was fixed and not to worry. We had a brief discussion about STD which is a mood killer of course but necessary. All the while we are talking she’s still rubbing her pussy on me until it just slides in and we both let out a soft moan. She rode me for ten minutes or so and said she was going to cum. She didn’t tell me she was a squirter though and both of us were drenched. I found that very sexy and encouraged her just to let go at which point she squirted again only more than the first time. That was all I could handle, and I pulled out just in case and shot all over her pussy.

We just sat there catching our breath for a bit when she got up to use the restroom. I heard the shower going, so I figured I’d join in to clean myself up as well. She toweled off, and we both dressed. I put on a robe, but she had to leave.

We exchanged numbers in case we were ever in the same area again, and she mentioned she was exploring her bisexuality so if my SO would like to join she’d be up for it. We kissed goodbye, and I asked if she’d like me to walk her out which she politely declined.

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? I get great, told my SO about it and coincidentally she went out doing the same thing although she wasn’t successful finding someone that night so I have to make it up to her soon.

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

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

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

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? My SO who loved the story

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? Amazing sex with a beautiful stranger

What was the WORST thing about this hookup? Nothing

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

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