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What's the craziest request you've had from an escort?


Quincy_7
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Many years ago, when I was living in NYC, an escort that I'd hired for what I assumed was going to be a simple evening of fun suddenly suggested we role-play Coach and Student-Athlete. I've never really done role-play in the bedroom (even though I happen to teach acting for a living, but that doesn't necessarily translate), but he was so excited about the idea that I gave it a shot for him. I think I was probably terrible at it (especially considering my knowledge of coaches and sports is somewhat limited), but I do always look back at that night with great fondness, because I know he was being completely honest about what he wanted. He got very into it, which actually made it fun for me.

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A therapeutic masseur asked me to FF him. :eek:

 

 

Another unofficial companion asked me to do a really involved RP. The first sentence of his scenario was: “Please do not eat or drink anything citric - orange or pineapple juice, etc. (this overpowers your natural odor) would request eating lamb and blue cheese if you can today tomorrow. “

It got complicated from there.

Edited by Keith30309
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Back in 1990s, when "Happy Days" was still popular, Kurt from Long Island asked me to call him Chachi. He did look a little like Scott Baio.

 

My response, Sure if you stop wearing t-shirts and jockey shorts when we meet that's what Scott Baio would do.

 

He agreed, and from then on took all his clothes off a few seconds after ringing my door bell. "Hi, Chachi."

Edited by WilliamM
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Whipped Cream and Chocolate sause. The strategically placed cherries was my idea. He supplied the nuts.

 

1473869103912.jpeg

Now that looks delicious even without the nuts!

Whipped Cream and Chocolate sause. The strategically placed cherries was my idea. He supplied the nuts.
Edited by Just966
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I once met an escort for a few hours and we bonded over life shit. He asked for my help in solving quant problems for a fashion business course he was doing. I ended up helping him for a few semesters, including in-person math & business finance lessons. We never got intimate though he made overtures. For me, it was physically over after the first encounter.

 

Another one took meditation lessons from me.

 

A famous Russian masseur from NYC used to reach out for life/relationship advice.

 

All those experiences tought me a lot about the illusion of physical beauty and the inner focus needed to make life beautiful for yourself and others.

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Another unofficial companion asked me to do a really involved RP. The first sentence of his scenario was: “Please do not eat or drink anything citric - orange or pineapple juice, etc. (this overpowers your natural odor) would request eating lamb and blue cheese if you can today tomorrow. “

It got complicated from there.

It sounds hot @Keith30309. Please elaborate on the “complication”. :oops:
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My craziest experience wasnt a behavior, fetish, activity.

 

It was a guy who gave me a runaround for 10 hours, showed up for an hour session, stayed overnight, voluntarily waived his fee, told me he wanted to see me again, asked to borrow money as I drove him home, started to cry, bolted from my car, and ran off.

 

And while it was an insane ride, I must admit that the hours in my hotel room were some of the best ever spent in this pasttime.

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His mom called to check on his wearabouts during our session and he put her on speaker so I could “confirm we were at wendy’s“.

 

Hand to God, she and I just had a lovely lunch on Friday together.

 

Is she aware you're a client of his?

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Usually it's clients making the requests but I recently had an escort ask if he could piss in my mouth. I understand that that's a fetish for some but it isn't for me and so I said no.

 

I would have said "NO" as well. If I want an escort to introduce me to WS, I'll initiate it. I'm curious but I desire a certain man who would know how to prepare for this type of play and who could introduce me to this play in a more timely manner.

 

A hot escort in San Francisco only wants to have his cock serviced; I saw him when he had just begun, and although I don't "partake of one's leche" since HIV/AIDS came to be-- I did suggest to him that in order to have some sweet and tasty "cream"-- eat pineapple or drink pineapple juice. Upon our third or fourth meeting, he stated that he had taken my suggestion and that some of his clients just couldn't wait for him to unload down their throats.

 

I have yet to savor his purported sweet juices: https://rentmen.eu/JuicyAznBoyCock

Edited by Axiom2001
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