The Sissy Streetwalker

By Annie DuBois

Copyright 2012 by Annie DuBois

Smashwords Edition

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Taylor smiled as he rolled on the first of his fishnet stockings. It was Friday night, and there was money to be made. It was time to get en femme. The actual day had been a bore; Taylor had spent most of his time daydreaming. He had spent his entire Chemistry class thinking about getting dressed up, and his entire work shift fantasizing about getting fucked. When the last table at the restaurant he worked at had been served, the excited young man hopped on the subway and headed home as fast as he possibly could.

As soon as he stepped foot in his modest apartment, the suffocating men’s clothing immediately came off. He wasn’t dressed up yet, but at least he was naked. Some mood music, and a few candles later, Taylor was ready for business. As he began to caress his boy-cock and balls, Taylor noticed a small patch of stubble on his taint. It had been a few days since he had shaved, and there was no way he was going out on the streets without looking perfect.

Taylor walked into the bathroom and began drawing himself a nice, hot bath. While waiting for the tub to fill, Taylor licked his pinky and slid it into his asshole. It was tight. Way too tight for a Friday night. Reaching into his medicine cabinet, Taylor produced a small pink butt-plug and a small, heart shaped bottle of lube. Opening the bottle and applying a generous dab of lube to the butt-plug, Taylor sat the wedge shaped dildo on the floor. Dropping to his knees and straddling the plug, the young twink lowered down his slim, girlish body until the plug was halfway up his asshole. Sticking a finger in his mouth and lowering his body down the rest of the way, Taylor let out a moan as the rest of the slender plug entered his body.

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