On the Boardroom Table with a Cougar

by Randall

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? NYC
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Junior manager
What’s your current relationship status? Dating casually
Religious affiliation: Jewish
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Experienced
How many sexual partners have you had in your life (including oral sex)? A lot
How many hookup stories have you here posted before? None

On the board room table with a cougar

How long ago did this hookup happen? Last Wednesday

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 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? I was posted at the New York office of my company for a six month project. She is the office manager. She’s 40 years old. She has a nice figure. I loved watching her walk about the office in her dresses and heels. She took a liking to me and the idea occured to me that she would be an interesting hook-up. We started flirting as we got to know each other. This went on for all the time I’ve been at the office. As my project was coming to an end and I will be leaving, it was clear something would happen before I left. Maybe lunch or something more…

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was preparing a presentation to summarize my six month project. I was finishing up at the end of this month, and then I was going to head back to the home office. I asked her if she could help me put together my presentation materials. We stayed late at the office on Wednesday night putting the finishing touches on my presentation. We were flirting while we were working together. By the time everyone had left the office, our flirting turned to touching, and then we started making out.

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? It didn’t take long for me to propose sex. I pulled down her skirt and she unzipped my pants. Both of us were naked from the waist down. I sat her on the board room table and started fucking her right there, with her sitting on the edge of the table and me standing. The table was just the right height for this. We were embracing and kissing a bit too. She was getting into it and then laid her back down on the table and raised her legs in the air while I continued to fuck her pussy. While there was no one else in the office, we were still careful not to be too loud. I pulled out and came, shooting my load across the table, trying to avoid hitting her dress. Thankfully, none of it hit my presentation materials. We cleaned up, packed up my things, and then left for the night.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, 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? My last day at work was two days later on Friday. I think we both knew this was a quick NSA fuck. I never talked to her about Wednesday night. As I was about to give my final presentation, I was carrying my presentation materials to the meeting, I winked and smiled at her while going to the meeting room, the very board room where we fucked on the table. She smiled back so I take it she enjoyed our night. I don’t know if I’ll ever have sex with an older woman like that again. While it was something I really wanted to do and try, it didn’t feel the same as sex with girls my age. I don’t know what it is. She smelled a bit different. Some of it was the fragrance that younger women like. I think her body odor was more mature too. On Saturday night after I finished up, some of our younger colleagues saw me off at a local bar. I hooked up with one of the interns, and that hookup felt much more pleasurable: even though it was a hot and humid day, the sweat from the intern smelled and tasted sweater, her body was tighter, and she had a more youthful sense of adventure. The office manager was more sexually confident and that was good, just different.

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, Learning new things, experimenting

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

To whom did you talk about the hookup? How did they react? I told my best friend back home by text. He hears many of my stories, so he did’t say much, except that he expected I would have been screwing more women during my time in NYC.

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

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? I don’t know / I’m not sure

Do you regret this hookup? Somewhat

Why do you regret this hookup? I’s still do it again, because I wanted the experience, and I was intrigued about her. But given that I had more sexual satisfaction with the intern, I should have spent more time with the intern.

What was the BEST thing about this hookup? Sex with an older woman. Doing it at work on the board room table added to the excitement.

What was the WORST thing about this hookup? I should have spent more time hooking up with one of the younger women in the office.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It was a good experience about sex with an older woman. I won’t say that I will never do it again, but I do know better what I like now.

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

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

What do you think about the Casual Sex Project? I’ll be reading some more of these stories

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