Halloween Party Sissy

Halloween Gender Swap Stories

Halloween Party Sissy

Sissified for the Office Party

Coming October 15, 2026 — pre-order on

About this book

When Ryan skips the company Halloween party for the umpteenth time, his stunning boss Natasha has finally had enough. She gives him an ultimatum: attend the party or lose his job. The catch? She has the perfect “spare costume” waiting in her office — a ridiculously short, frilly French maid outfit complete with stockings, heels, and a tiny white apron.

What starts as a humiliating costume quickly becomes something far more permanent. Before Ryan can protest, Natasha locks him in a steel chastity cage, applies his makeup, and sends him downstairs to serve drinks and flirt with his unsuspecting male coworkers. As the night unfolds, Ryan discovers something terrifying: he loves the attention. He loves being stared at. He loves feeling pretty.
But the real night begins after the party ends.

Back in her private office, Natasha bends her new maid over her desk and claims him completely. When it’s over, she dangles the tiny key to his cage in front of his face… and locks it away in her desk drawer.

“Your work is going to improve dramatically from now on,” she purrs. “And so is your new role as my personal office sissy.”

A deliciously humiliating Halloween tale of forced feminization, public teasing, and total boss-controlled surrender.