A white femboy, Kevin, works as a Correctional Treatment Specialist at a federal prison. He provides therapeutic services to inmates, focusing on gang members and helping them prepare for re-entry into society. At home, Kevin explores his feminine side by dressing as a girl and indulging in fantasies of being used by multiple men. He becomes fascinated with the idea of sissy chastity, believing it could help him feel more feminine and submissive. One weekend, he orders a pink chastity cage, and after some hesitation, locks himself in, committing to remain locked for thirty days, even while at work. The constant awareness of the cage makes him feel more delicate and reinforces his desire to embrace his sissy side.

Kevin struggles with his commitment after finding the inmates he works with increasingly attractive. Unable to resist, he unlocks himself and masturbates. Determined to stay locked, he purchases a lockbox and seals the key away for thirty days. He gets a new client, Keeshawn 'Mad Dog' Powers, a black gang member due for release in a month. Kevin recognizes Keeshawn from an amateur video where a girl is used by several men in a parking lot. Kevin's attraction to Keeshawn grows, along with his desire to be used like the girl in the video. During their sessions, Kevin probes Keeshawn about prison life and sex, pretending it's for psychological insight. Keeshawn talks about how he had a sissy that served him before he got busted, and he details how he trains them to be sluts. Kevin listens, increasingly aroused, following Keeshawn's tips on cock sucking and riding practice.

On the day before Keeshawn's release, he describes a club where women and men throw themselves at thugs, getting used in a fenced parking lot. Kevin, overwhelmed with arousal, asks how to get invited. Keeshawn gives him a gold card, implying he knows Kevin's desires. He adds a note, "My kind of lady," and tells Kevin he likes sissies. Kevin takes the card, conflicted but excited. He spends the next week debating whether to go to the club. Concerns about his career and getting caught weigh on him, but his desire to fulfill his fantasy is stronger.

On the night of Keeshawn's release party, Kevin dresses in sexy, revealing clothes and goes to the club. He's nervous about being recognized by men he's counseled, but he's also worried he won't be chosen for the special event in the parking lot. Once inside, he dances and grinds with the thugs, his femininity heightened by a month in chastity. He competes with other women for the chance to be selected for the gangbang, participating in contests like lap dances. Kevin gives Keeshawn a lap dance, and Keeshawn hints that he knows Kevin's true identity. Despite his fears, Kevin is thrilled when he's selected to be the bitch for the night.

In the parking lot, Kevin finds four of Keeshawn's friends waiting, one of them filming. Kevin participates in a blowbang and then a gangbang, getting used sexually and loving every moment. His fantasy fulfilled, Kevin embraces his identity and the thrill of submission.