This post is sponsored by The T-Bar.


What’s your gender? Man
How old are you? 47
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Virginia
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Sr. VP
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)? 141
How many hookup stories have you here posted before? 9

Awards Night Trophy

How long ago did this hookup happen? This week

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? For less than a week

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? I was at a beautiful hotel with some work colleagues. Our team just won a number of awards at a dinner and we went to the hotel bar to celebrate. It was a classy, high-end place with quality people. We put the awards on the bar and naturally people started asking us about them. It didn’t take long before my team filtered out. I was about to leave when this pretty, tall, blonde slid in next to me to ask about the awards. I told them what they’re for, what I do, etc. We really hit it off and talked for more than an hour. “Nadine” is strikingly beautiful, 27 — 20 years younger than me — and a business professional attending a conference. She was wearing a pants suit and blouse covering what looked to be impressive cleavage. I had to get going but we agreed to exchange phone numbers and maybe get together the next day before she had to leave for home.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She texted me and we agreed to meet after work in the same bar. We continued where we left off — talking about everything and anything. She was worldly and really smart. A real turn on. Then she tells me she’s attracted to intellect as much as looks. I know what that meant! Later she leaned over and tells me “I just got my boobs done. Wanna be the first to see them?” But of course! We paid our tab and headed to the elevator. It was crowded but I managed to stroke her back and firm ass on the way up. As we were going up so was my cock.

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 got to the room and she pinned me against the wall. (She’s a good 6 feet tall, just about what I am). We made out like long-lost lovers. She then took me to the couch where she straddled me and began rubbing against my hard cock. After many minutes of touching and kissing she grabbed my hand and playfully pushed me onto the bed. She mounted me and began to undress me, first shirt, then pants. She was giving me oral when I realized she was fully clothed. That didn’t take long. She stripped, revealing nicely done D cup boobs, a flat stomach, sexy and long firm legs and a great ass. Wow. Just wow. She joined me back in the bed and rubbed her clit against my cock shaft. This went on for many minutes. I started to think about getting a condom but she instead slid me inside her wet pussy. We had sex for quite a while in many different positions and paused once in a while for oral. I was able to lift her up as well, something she said no one does easily given her tall build. Eventually I pulled out and came on her ass after doggy style.

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 laid on the bed and talked for quite a while. She had to leave the next morning and so we both knew this was a one-time thing.

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? 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? 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? No one.

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? Fucking a beautiful woman, the passion, and doing so bareback. Wow.

What was the WORST thing about this hookup? I’m married.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve got to stop doing this!

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’ve slept with many women lately and I need to stop. This one taught me to maybe get some help.

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

What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!