What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Boston
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Executive
What’s your current relationship status? Single
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)? 100+
How many hookup stories have you here posted before? 2
Mashup At The Montage During Milken
How long ago did this hookup happen? 3 years
What was your relationship status at the time? Single
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? X was a 50 to 55 year old sexual kitten. About 5’5″, toned by a dozen or so dietitians, chefs, and personal trainers. Dressed by a stylist. She was incredibly hot if you don’t mind your women powerful and in control of themselves. She was two seats down from me at the bar in the Montage – separated by a vapid thing in a clingy, too shiny dress.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were both in LAX for the Milken conference – an annual gathering of CEOs, Bankers, Politicians, Celebrities, and Nobel Laureates. It is an amazing event and attendance is almost mandatory in certain fields (mine included). Getting a room at the Beverly Hilton, where the conference occurs, is impossible. We were both down the street at the Montage which, in fairness, is probably a better place to be. It was around 11:30 pm and we had both returned from some tedious dinner to have a drink at the bar.
Between us sat some C-Level starlet in a shimmering clingy sheath. She was about 27, big camera hot as only a few folks can be, hammered, and clearly looking for a rich sponsor. She was also painfully stupid; and, I mean tragically dumb. As she was trying to hold court, I caught the eye of X, smiled, and rolled my eyes. Game on. X proceeded to drag her over the coals for a few minutes until Starlet finally realized how unwanted she was and left.
X and I began to chat across the now empty seat and she asked me why I didn’t take Starlet up for a night of fun. I responded by noting that “stupid is an STD” and that I was afraid the “stupid might infect my dick and ultimately reach my brain – a risk I don’t really want to take”. She looked me in the eyes and said: “I am pretty sure I am not infected with stupid”.
Hey, we were drunk and it seemed way coyer that night…
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 left for my room. We started making out in the elevator and she was unlatching my belt as we entered my room. We had pretty intense but vanilla sex for about two hours. Lots of oral, she rode me for an extended period of time.
We both seemed quite satisfied but something was missing. Eventually, it was late and she left for her room.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, more than 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 saw each other at the conference the next day and there was no awkwardness – neither of us is a child. The day after, I ran into her at breakfast and she asked when my flight was. I said at noon (it was about 7:30 AM) and she noted that gave us about two hours to have some fun. I grabbed a coffee and we went to her room.
Within a minute of closing the door, she was on her hands and knees, heels and stockings still on, skirt over her back, cheek to the mattress, as I ripped a hole in her fishnets and plunged into her cunt. This time we used no condom – I just tore open the seam of her stockings and drove into her. I fucked her hard for about 10 minutes, caring nothing about her pleasure, and then spun her around and shoved my cock down her throat as I came.
She swallowed and continued to milk me while fingering herself vigorously. I came, she came. My state of mild domination inspired me and I proceeded to tie her hands together and then to the bedpost with my tie. She was now laying face down, hands lashed to the bed frame above her head, fully clothed, cum leaking from her cunt. I grabbed the waist sashes from the robes in her closet and tied each foot similarly to the bed. She was clearly turned on.
I looked around the room and found a half-bottle of wine which I proceeded to shove up her cunt to stop the leakage. She was now tied up, full of cum, and plugged with a giant phallus.
I left her to writhe for a few minutes and got cleaned up. I came back and sat down above her head – her arms over one leg with my cock right by her face. As she started sucking me, I asked what her limits were. Her response was “no marks, no anal. Use me.”
I followed directions for about 90 minutes. I am not really into domination but I have to say, that was an extraordinary experience. I really just did not think about her pleasure at all; yet, she got it. I am not sure I ‘get it’ and I would not want to have to do it frequently but it sure was a hell of a good time!
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant, Sterilization
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? First real experience dominating a woman.
What was the WORST thing about this hookup? nada
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? nope
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
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