KK's Quickies: Feisty Featherweight to Ravishing Ring Girl (2/4)

This little story is a bit special, because it's being released in collaboration with one of the best TG fiction writers out there, DS1000! Using the same initial idea, we each came up with our own illustrated mini-tale. If you want to see their awesome alternate version, go to https://www.patreon.com/ds1000 or https://www.deviantart.com/ds1000

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Though he didn’t much care for her assertion that he would look “pretty” as a girl, Benny had to admit that her logic was sound. So, after a few more hours spent being badgered and persuaded, he gave in and let her make him over. By the time he’d shaved his legs, plucked his eyebrows, had his hair, nails, and makeup done, and been stuffed into a frilly pink padded bra, matching panties, and a simple white summer dress, he had to admit that the young woman staring back at him in the mirror was, despite her short pixie cut, very attractive and feminine-looking. Of course, he denied it to the last.

His girlfriend’s plan worked, however, and for that he was grateful. Benny showed up mid-afternoon, carrying a purse and walking slightly awkwardly in a pair of kitten heels, but everybody assumed he was the wife or girlfriend of one of the boxers, and the only second glance he received was from a fighter checking out his legs! Both embarrassed and relieved, Benny took a picture to prove he’d been at the gym and sent it to Ross on the way home.

Though Benny had managed to avoid being humiliated in person, the picture circulated all over social media for the next month, making his life a living hell. Perhaps unsurprisingly, his girlfriend left him not long after. His hormone problem gave him all sorts of difficulty “standing to attention” in the bedroom, and besides, no girl wanted a boyfriend who looked cuter in a dress and heels than she did.

Not long after, Benny’s boxing career fell apart completely. When he tried to enter his first competition since the humiliating rematch, he was handed a ban for steroid use! He tried desperately to explain he had been using hormone therapy on his doctor’s orders, to rectify his hormone imbalance, but as far as the urine test was concerned, Benny had been using illegal substances while training, and that was that.

With all of his money going into treatments for his condition, Benny was soon penniless. Desperate to make some cash the only way he knew how, he turned to an underground boxing ring run by some very powerful and shady mobsters. Sure, Benny wasn’t what he’d been even half a year ago, but he was still a cut above the low-life hoodlums who did their business in dirty basements and secret warehouses. Betting was the name of the game in the underground ring, and several mobsters were eager to cash in on a former superstar like Benny MacDonald.

With an expensive Cuban cigar in one hand, a drink in the other, and even an attractive blonde cocktail waitress named Lacy batting her eyelashes at him, Benny was feeling like his old up-and-coming celebrity self again as one of the biggest bettors in the city told him how much money they would make together. His first big fight was scheduled in a matter of weeks…