by

What’s your gender? Woman
How old are you? 51
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Austin TX
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? SVP Sales
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? About 15
How many hookup stories have you here posted before? None

Girthy Guy In Gotham

How long ago did this hookup happen? Two or so years ago

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For more than 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? R is a consultant in my sector. He is incredibly well known and hyper connected. I have known him casually / professionally for several years. He advised the last company I worked with through a transaction and worked with the acquirers of the company I am currently with.

He is not a “good looking guy” but he is reasonably handsome, incredibly smart, funny, and very successful at what he does.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was considering a change of jobs and was going to be in Boston (where he is based) and asked to have dinner.

We met at a great place and the dinner was incredibly professional. I did not really know him all that well before – we had met many times professionally but never spent any real time together. I have to say, no man has ever been that focused on what I was trying to accomplish with my career. Nor had anyone been that blunt about what was realistic and not realistic. As dinner was winding down I realized that the last 90 minutes had been 100% focused on me and my success. I did not want that to end.

As we were leaving I mentioned that there was a great bar nearby and asked if he would like another drink. He complied.

The place was packed but he found us space at a table with another couple. He looked at me, smiled, and said “I don’t think we are going to see a server soon, what would you like?” Then he did the same to the couple we did not know and went to the bar.

He returned shortly with drinks and the woman next to me simply grabbed my arm, looked into my eyes, and said, “That’s a real man”. It was then I knew I had to have him.

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 felt a lot of sexual tension building and at one point turned to him, grabbed his cheeks, and kissed him. It was long and passionate. We broke off and I was a bit terrified. He cracked a wry smile and said, rather nonchalantly, “I settled the bill earlier”. He grabbed my hand, stood me up, patted my ass as if he owned it, nodded to our new friends and said, “Let me take you home now.”

We got back to my hotel and got busy. I wasn’t expecting a hookup so was not shaved. Seriously, it had been ten days. He didn’t seem to mind at all. His cock was rather average length but incredibly thick. He had a way of fucking you for 45 to 50 seconds and then going all the way in where his girth really mattered.

In 30 plus years I don’t think I have ever been that sexually pleased. I have had more than one orgasm before but never four or five back to back.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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? He left around 3 AM. I was pretty messed up after that. I had “cheated” on my significant other, slept with the most powerful person in my professional network, and acted like a total slut. At one point I was pretty sure I was screaming “Give me that fat cock!”, which is definitely not in character.

A few weeks later we saw each other at an industry event and he was, as usual, incredibly professional, complimentary of my accomplishments in front of my CEO and key board members and genuinely nice.

I texted him later that night and he took me to new heights 🙂

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) I’m 53!

What were your motives for this hookup? 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? Not at all

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Not at all

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 sister. She was impressed and appalled. She was happy I was “having fun” but she also asked where it was going. The answer was obviously “no where”. She told me to end it

I saw R a few weeks after that and when he asked if I would like to go play I said no. And that I was in a relationship and owed it to him to make it work.

He was magnanimous and wished me the best of luck.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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? I am a 50 plus corporate executive. In my 30 plus years of professional life no man has ever treated me with the professional respect this man has. None. He also finds me intellectually and sexually attractive. Right now, when I see him, he asks about how I am doing, how my career is going, and how my personal life is evolving. In that order. He never hits on me. But, I also know he would happily take me home. That is super sexy.

What was the WORST thing about this hookup? There is no way we end up together. I really like my husband – he is a great guy. But, he simply cannot play in the league R does. He’s better looking but he’s not that smart, not that sophisticated, not that smooth. Whenever I see R now, I realize that the man I am married to cannot be the man he is. He cannot work a cocktail party of executives and PE investors, he has not read five books this month, and he cannot rock my world sexually in the same way.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Done with them. If I need another, I’ll call R

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

All things considered, how NEGATIVE was this experience? A little negative

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