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What’s your gender? Man
How old are you? 52
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 occupation? Executive
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)? ~60
How many hookup stories have you here posted before? None

Sex with a Powerful Woman

How long ago did this hookup happen? 20 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

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? Jane is a high-power woman. She is quite well-known in the finance world because of her work. She is somewhat known in the general public because of TV news appearances once in a while. Not a celeb in any way, but well-known enough in the relevant circles that it feels like she’s famous. We worked together for a few years when I was a young administrator in a government branch she also worked with. She is over 10 years my senior, married, had three kids, but we hit it off and became good friends. We loved talking and laughing. I liked also that she was obviously rising in the finance world and I enjoyed the attention from someone of her class and status. At some point – can’t pinpoint it – we started flirting.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had gone to several conferences out of town over our work together. Usually we happened to be at these conferences together. This time, we actually planned our attendance together. Took the same flights to DC and booked the same hotel. It was a three day event. After dinner the first night, I can’t remember how, but we ended up in her room. Chatting and flirting. I remember mustering up the guts to tell her about my fetish of spanking. We didn’t touch each other that evening. I went back to my room and masterbated myself to sleep. The next night she invited me to her room again and then it started.

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 started kissing and making out. I couldn’t believe it was actually happening. She felt so good. For whatever reason, I prefer women who are older than me. I always did (even had sex with a woman well into her 70s, but that’s another story), and I don’t know why this is but I prefer a mature body. Younger woman rarely turn me on. Her body was relatively fit and I loved the feel of it. While making out – I decided to take the step and told her I would like to spank her. She just complied and got over my knee. I remember feeling like a dream came true. I spanked her and fingered her from behind while spanking. She actually came from it. She told me she was shocked by this experience and loved it. I didn’t cum that night and again went back to my room to masterbate again and dream about the experience.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

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? We had returned to our home city and went back to work. We continued to see each other a few more times over the years. She had since left her position and joined the corporate world. She became rich and powerful. And as I said, she is well known in her circles and appears on TV every now and then. We met a few more times while she was already getting to her position. She became an absolute spanking-addict. She NEEDED to be spanked in order to cum. During our final encounter, I used a belt. She went crazy with passion and came so much harder when his with the belt. One of my best feelings in life is when I happen to read about her or interviews with her. Even better are the times I happen to see her on TV, talking tough about her work and negotiations with employees, unions, government etc. She is so powerful on TV and so full of control and dominance. And I love having this little secret that in the bedroom she NEEDS the opposite and craves domination. It has been a turn-on for me for 20 years and I very frequently think about our adventures while masterbating, or even while I’m with other women.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Birth control pill / patch / ring / injection / implant, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Power / Dominance

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? I don’t know

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 didn’t give a clear ‘yes’, but I didn’t give a ‘no’

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? Years later, told a therapist about it but did not give any names or clues. Other than that – no one.

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? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? For the first time actually spanking a woman and living my life-long fantasy.

What was the WORST thing about this hookup? She was married and I felt like it would be a dead end.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I gained courage to tell subsequent women about my fantasies and it helped my life a lot.

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

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

What do you think about the Casual Sex Project? Since learning about this project, I have managed to stop watching porn completely. Have not gone to a single porn site in several months. So it’s helped me get over porn addiction. But I am scared this site is becoming an addiction of its own… Hope not…

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