What’s Wrong Dollface?

It was Wednesday when Bob awoke, and that meant it was his turn to buy beer for the apartment. Upon looking out the window though, he realized that he had no idea where he was. He was either uptown or in some kind of alternate dimension that bore a strange resemblance to uptown. He decided that he was probably just uptown.

After making this affirmation, Bob’s gaze shifted back down to his unfamiliar bed. In it, curled next to him, was a figure of particular heft and altitude. From under the comforter protruded the most heinous set of bunions he had ever seen, and somewhere amidst them was a pair of feet too. He knew he had to get out of there before this sleeping giant awoke, but his pants were nowhere to be seen.

Throwing himself upon a set of scattered dresser drawers, Bob rifled through for dear life. The only thing not covered in blood or semen was a bleach-stained floral print muumuu. He was about to throw it back when he heard a coarse, screeching yawn from the bed and knew it was too late.

Walking out onto the streets, Bob was hollered at by everyone he passed. It annoyed him at first, but then he realized how easily free shit started coming his way. He never had to pay for a train ride or cigarette again. He could even get some lovesick businessman to buy him the 40s he needed.

“Thank God I 86’d that moustache the other day,” Bob thought as a stockbroker bought him a half dozen St. Ides, “or else this scam woulda never worked!”

Clutching the bottles in hand and waiting for another train, Bob thought to himself about women’s rights and equality. He couldn’t help but wonder why anyone would want to relinquish free gifts like these just to be on a level playing field with the opposite sex. As a man, he had to busk his ass off in the streets to make money; learning how to play guitar since no one would support a bum with no talents. But within his first 12 hours dressed as a woman, he’d raked in more freebies than he could ever imagine.

Just then, a group of scantily clad Jezebels approached twirling purses filled with bricks. “Look at the new girl,” one laughed amidst dainty chomps of a White Owl stogy. “Cuttin’ in on our territory and not givin’ us a cut!”

“Poor form,” said the hooker at the head of the pack, and before Bob could get a word in he was on the receiving end of an imitation Prada pummeling. Somewhere in the fray his bottles fell and smashed with a vibration that ricocheted off the linoleum walls.

The fight was called when there were no more press-on nails to reapply. The head hooker rallied her troops, gave Bob one last kick in the ribs, and said “You ain’t getting no more freebies in this town looking like that. Now you godda work for it like the rest of us!”

As they left the terminal, Bob sat on his bench and wept. Even dressed as a woman, he couldn’t find it in him to hit a woman back. What’s more, without the alcohol he knew we wouldn’t allow him in the apartment, and he didn’t even have money for a train ticket. He was at an all time low when a pudgy business type waddled in and took the empty seat next to his.

“What’s wrong dollface?” said the suit as he produced a tissue and wiped Bob’s tears. “So you got a little banged up, it’s a rough neighborhood, that sort of thing’s bound to happen.”

“But,” he said as he whipped out a wad of bills, “at least your lips still look good.”

–Ilan Moskowitz

The Man From Corporate

The Disproportionate Orgy


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