Becoming a Shemale Escort: Chapter 5

secrets7He didn’t try to kiss me.  He didn’t grab my boobs.  He didn’t rip my clothes off, or even undress himself.  Instead, Jack asked me to sit on the edge of the desk and hike my skirt up and spread my legs. He then rolled the desk’s over-sized matching chair toward me and, like an old frayed teddy bear, plopped down in it. His face betrayed a bashful grin as he rolled the chair closer and closer.

I really had no idea what would happen next. But I was no longer afraid, just really curious. So far, at least, if I had to describe him, it would be, as I already mentioned, as an old teddy bear. Gentle but not necessarily cuddly (he was too ugly for that!). And what he was now doing — rolling the chair every closer so that his face was pressed closer and closer to my panty-less crotch — sparked some involuntary whimsy from my lips:

“I feel like my body is a computer and you’re about to start typing on the keyboard!” I laughed.  And he did, too — a hoarse, breathy laugh that tickled my scrotum (yes, his face was that close!).

He nuzzled his face ever tighter against my male genitals, already pressed tight against the flesh-colored pantyhose that he had instructed me to wear. Why he had been so insistent that I wear no panties, I now understood.

If he was expecting me to get hard…well, he would have been within his rights to want a refund. I glanced down and tried to see if he was getting hard — that was all that counted, right? — and I thought/hoped I detected a growing bulge in his pants. Maybe just wishful thinking?

I wanted and needed for Jack to be happy…so that Marvin would be happy…so that I wouldn’t be fired. Most of all, I wanted this moment to be over with, in a satisfactory manner, so that I could feel like I’d actually earned the money. Yes, I wanted to make sure Jack got his satisfaction. Pride in my new identity was at stake.

Against the nylon of my hose, his rough thumb began to make circular motions around the head of my still flaccid penis.  He did it so much and so hard, I was beginning to feel painfully sore and inflamed at the head of my urethra.  I had to change the subject of his attention.

“Let me suck your cock,” I suddenly said.

“With Marvin’s other girls, I always suck their cocks.”  He seemed puzzled.

“Well, give me a chance,” I begged. “You might be surprised. You might really like it. I give really good head.”

About Joy Saint James

Day job in Big Banking. Elsewhere I'm @ScholarlySlut, whose essays and erotica have appeared in various print anthologies and websites. Email: joy.st.james@hotmail.com.

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