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Betting on the Sissy: Short Erotic Story: Gamer Femboy Feminization
A friendly bet. A humiliating punishment. And a hunger he never expected.
Saturday nights are for FIFA, beers, and hanging out with the guys. Or at least, that’s what Casey thought.
When a heated gaming session with his best friend, Brad, turns into a high-stakes bet, Casey is confident he’ll win. But he loses. And the price? Wearing a tiny, humiliating skirt belonging to Brad’s ex-girlfriend.
Casey expects shame. He expects mockery. What he doesn't expect is how good the silk feels against his skin... or the dark, hungry look in his best friend’s eyes.
One night of confusion turns into a week of obsession. Casey can’t stop thinking about that night. He can’t stop touching himself. And when the next Saturday comes around, he doesn't wait to lose a bet. He shows up ready to play a very different game.
Betting on the Sissy is a steamy M/M dark romance short story featuring best-friends-to-lovers, forced feminization, crossdressing, and high-heat submission. Intended for mature audiences.
Saturday nights are for FIFA, beers, and hanging out with the guys. Or at least, that’s what Casey thought.
When a heated gaming session with his best friend, Brad, turns into a high-stakes bet, Casey is confident he’ll win. But he loses. And the price? Wearing a tiny, humiliating skirt belonging to Brad’s ex-girlfriend.
Casey expects shame. He expects mockery. What he doesn't expect is how good the silk feels against his skin... or the dark, hungry look in his best friend’s eyes.
One night of confusion turns into a week of obsession. Casey can’t stop thinking about that night. He can’t stop touching himself. And when the next Saturday comes around, he doesn't wait to lose a bet. He shows up ready to play a very different game.
Betting on the Sissy is a steamy M/M dark romance short story featuring best-friends-to-lovers, forced feminization, crossdressing, and high-heat submission. Intended for mature audiences.
22 pages, Kindle Edition
Published December 5, 2025
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Displaying 1 of 1 review
May 10, 2026
3.5 stars
Fun one! I'm a sucker for a best bros to lovers story, and with the feminization thrown in, this was really delicious. While the writing style was pretty plain, I did enjoy the characters, story, and spice. A nice, quick read if you're into sissyfication/feminization and M/M smut.
Fun one! I'm a sucker for a best bros to lovers story, and with the feminization thrown in, this was really delicious. While the writing style was pretty plain, I did enjoy the characters, story, and spice. A nice, quick read if you're into sissyfication/feminization and M/M smut.
Displaying 1 of 1 review