KK's Quickies: Feisty Featherweight to Ravishing Ring Girl (1/4)

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.deviantart.com/ds1000, and you can always check out their other work on https://www.patreon.com/ds1000/ as well!

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Benny “Pretty Boy” MacDonald had it all: looks, charm, and a hell of a right hook. At the tender age of nineteen, he was dominating the boxing circuit as an ultra-featherweight, using his blinding speed and quickness to make up for his small stature and lack of heavy hitting. Benny was good, and he knew it--perhaps too much so! After humiliating his former friend and long-time rival Patrick Ross in a taunt-filled three rounds, weaving around his heavier opponent and wearing him down with jab after lightning-fast jab, he told reporters that Ross “fought like a girl” and “wasn’t man enough” to be in the ring with him.

A furious Ross responded by challenging Benny to a rematch in six months’ time, the loser of which would have to show up to the opponent’s gym… wearing a dress! Benny accepted without a second thought, and that was where things started to go wrong. As the months passed, the normally whip-thin Benny began to realize he was gaining weight around his hips and buttocks, and worse, he was losing muscle mass, as well! His gym’s doctor discovered a hormone imbalance in his blood tests, but despite giving him a mountain of hormone pills and creams to treat his increasingly itchy chest, he told the young boxer that the only thing he could really do was wait it out.

Benny was still quick on his feet in the ring, but his punches were growing increasingly weak and on the mental side of things, his puffy nipples and widening hips were a huge blow to his confidence every time he looked in the mirror. When the much-anticipated fight with Ross rolled around, Benny chose to tape up his chest and wear a wrestler’s leotard instead of going bare-chested. To his embarrassment, his rival only needed two rounds for the referees to reach a decision. Benny was simply too weak, and too lacking in concentration, to make a fair fight of it.

Now that he had lost, Benny was faced with the unbearable prospect of following through on the wager. He spent days moping, hoping Ross and the media would somehow forget about it, but every day spent delaying only made the inevitable loom larger. Finally, his girlfriend suggested something that sounded, at first, completely hare-brained: rather than showing up to Ross’s gym looking like a man in a dress, so everyone could snap photos and laugh at him, she suggested a full-on makeover. With his fine facial features and slender, increasingly androgynous frame, she was sure she could make a passable girl out of him--and maybe even a cute one, at that.

“Nobody will bat an eye,” she explained. “All you have to do is show up--there was nothing in the bet about announcing yourself! If nobody recognizes you, you can be in and out in a jiffy…”