Revisiting Cheri the Escort

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Status: In Progress  |  Genre: Poetry  |  House: Booksiesilk Classic Group

Will returns to get the services of his friend, Cheri the escort

There comes a time in the lives of some men when obvious hits us right in the face. I need sex and I don’t like the current choices. I need that something extra that most women don’t pick up on, and if they do, they think it’s silly or childish. The obvious solution, however brief, is a hooker. But I prefer an escort like my friend Cheri. She’s gorgeous and knows me well.

It may seem odd that a man can have a platonic friendship with an escort, especially if he has used her services, but I do. Cheri and I have spent many of her “non-working” days just going places and having fun, each of knowing that sex will not be a part of it. No pressure or expectations, just enjoying each other’s company.

I was her “plus one” a birthday party for one of her girlfriends and she introduced me as a friend of her family. I took her to Florida for a tropical weekend holiday for the two of us, just for the fun of it. No sex was expected nor offered, and we had a great time.

That being said, when I do need her services, even though I still pay for her time, Cheri knows me well enough to deliver the experience that I need when I call her. So, I called her. When we get together, there is little need for much discussion; she knows exactly what I like and she claims that she enjoys playing the game. Another reason that I only call her and nobody else.

However, I decided to change up the procedure just for fun.

“I have an idea on how to make things a little more interesting,” I suggested.

“Are you suggesting something totally different?” she asked.

“No, just how we go about it.”

“Lucky for you that I’m in a playful mood, Will. What do you have in mind?”

“Let’s say that I will pay you one dollar for every minute that you suck my cock but don’t let me come.”

“That could be more expensive and painful than you want,” she warned with a grin.

“Maybe, but once you put your mouth on it, you can’t stop until I come and you can’t use your hands, unless you want to play with my balls.”

“We’ll have to find a comfortable position or my jaw will get tired,” she said thoughtfully. Obviously she thought the idea could be profitable.

“I’m thinking a sixty-nine would be perfect because I want to lick you to orgasm anyway.”

“I do enjoy what you do with your tongue, but what happens when I come?”

“Then you get a bonus and we keep trying for multiples.”

“What I mean, Will, is that when I come I don’t want to bite your dick off; I have to take my mouth off of it.”

“Well, that’s allowed because even if you hum on it, I’d surely come in your mouth. So, you can stroke it while you finish your orgasm, then put your mouth back on it.”

“I know you like me to come on your face, so what kind of bonus are we talking about?”

“Let’s say that whatever I end up paying you when you finally suck me off, I’ll give you the same amount for coming on my face, how’s that?”

“How about for EVERY time I come on your face?” (A fair counteroffer.)

“I can go along with that, but you have to be extra wet and really try to make me believe you’re actually having an orgasm.”

“I already told you that I’m in a pretty playful mood, so I won’t have to pretend, Will.”

I had one more suggestion, although I knew what the answer would be, no matter how I proposed it. But she had such a fabulous ass, so tight and athletic that I could not resist.

“What if, when we are through, I double the amount if you will take it anally?”

“Never gonna happen, Will, but you can eat my ass and dream about it.”

“I would consider it a privilege to bury my face in your sexy behind.”

“Well, usually time is money but now you’ve got me all hot and bothered. You’re gonna drink so much of my come that I’ll empty your checkbook today, Will.”

I came in her mouth in eighty-three minutes. She “came” three times. I added another bonus, and I enjoyed eating her ass. It was the best money I’d spent all year. And she had such a good time, she paid for dinner. I wish I could win the lottery.






Submitted: January 10, 2023

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