What’s the hardest thing you have ever had to do? Learn Latin? Run to win a 5-K race? Play hostess at a Black Tie dinner party? Perform the starring role in your school’s “The Nutcracker?” Execute a French manicure on your very own nails?
For me, the very, very, very hardest thing is putting a rubber on a limp penis. I’ve only had to do it once (thank God!), and that occurred during my very first date as a shemale escort. It was a truly unique skill I developed on the spot.
I could see him go limp as I fumbled in my purse for the condom. (Have you ever been able easily or quickly to find something in your purse when you need it most, when time is of the absolute essence?)
At first I didn’t think it would be a problem. All I had to do was lightly brush his sensitive skin with my finely manicured, sexy fingernails, right? After all, just moments earlier, his cock , though tiny, had been explosively erect. But that was then; this was now.
Then he had been fondling my own cock, which I preferred to think of as just an oversized clitty. To be frank, my clitty didn’t like the too rapt attentions of his monotonous, and rather rough, hand motions. The very tip of my big clitty was actually getting sore; my pantyhose felt like sandpaper.
If I could just make him cum, I would have earned my money, and I could leave.
I pressed the rubber against the head of his penis and clamped the rolled-up sides with my fingers. Then I took my tongue so that it tasted the rubber tip. Flicking my tongue, as I so desperately had hoped, gradually stiffened what I held between my fingers — sufficient to gain purchase to unroll the condom. As it unrolled, my lips parted and slid over the tip and down the ever lengthening, but still short, shaft.
Now my lips and throat and bobbing head could work their gliding magic, and they did. But, from Mr. Jackson, there were no quickening thrusts and volcanic eruptions, as with a younger man. Instead, when he came, I heard a barely perceptible grunt and felt the condom inflate like a tiny balloon. The texture and consistency felt like an over-ripe melon about to melt and get messy in my mouth.
When I left his office, he said a very formal thank-you, and I noticed that all around the walls were hanging pictures of his wife and children and grandchildren (I could only presume, I didn’t dare ask): mute witnesses to the display of his extramarital activities with a shemale. He must not have cared.
I only cared what he would tell Marvin, my pimp. Mr. Jackson – I mean Jack (I wasn’t supposed to know his last name) – was one of Marvin’s regulars. What kind of report card would I be given? I knew it would not be an “A,” because I had dissuaded him from doing what he really wanted – to play with my big clitty. So was I failure? Would Jack ever want to pay for me again? A satisfied, repeat customer?
Or would my very first trick also be my last?