The Sissy Streetwalker by Annie DuBois
(Trans Erotica)

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After a long week of work and school, Taylor Maguire has big plans for his Friday night: crossing-dressing in the sluttiest outfit he has, walking the streets, and having all kinds of filthy sex with as many complete strangers as possible.

Warning! This 3400 word short story contains graphic depictions of anal sex, blow jobs, throat fucking, spanking, rim jobs, and sissy boy prostitution. Not for the prudish!


Within minutes, cars began driving by Taylor’s corner. For any car that slowed down, the boy would lift up his skirt at them, showing them either his little sissy cock peeking out of his panties, or his round ass, complete with pink butt-plug. After the first few cars passed by, Taylor noticed a car stop and roll down its window. The car was a black Cadillac Escalade with tinted windows. An older black man poked his head out of the window.

“Hey there sexy, you looking for a date,” the stranger asked, the look of lust apparent on his face.

“I’d love one, daddy. Can I get in your car?” Taylor replied, lifting up his skirt, his hand brushing against his half hard boy-cock.

“Sure baby, hop in.”

Taylor strutted towards the passenger side door and hopped in the car. Looking over at his client, the boy was impressed. A lot of the time, the men that pick him up were fat and gross, but this man was actually kind of handsome. Sure, he was a little older, probably late middle aged, but he was very dashing and masculine. Taylor was determined to get things rolling.

“So Daddy,” the boy said rubbing his breasts, “why don’t you pull this car into that alley over there so we can get down to business.”

About Annie DuBois

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Published April 8, 2012 by Annie DuBois. 11 pages
Genres: Erotica, Gay & Lesbian, Literature & Fiction. Fiction

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