A man named Peter embraces life as a sissy after connecting with a transsexual woman, navigating gay bars, crossdressing, and an offered bar-tending job.
#sissy
62 stories tagged with this.
A nervous sissy transforms into a feminine slut for her first real meeting with an internet hookup at the door.
A 9-year-old boy named Rory awakens on his birthday and begins a transformation into Rebecca, a sissy persona drawn to laces and femininity.
A young trans girl is sent to rural Oregon to stay with her uncle and cousins in hopes of being "made into a man," but the experience only deepens her sense of female identity.
Teenage sissy Michael continues his feminization training under his mistress, encountering a mysterious new girl at the local shop.
A 15-year-old crossdresser explores his sexuality alone at home while his mother is away.
A young man secretly explores sissy fantasies and hypnosis-inspired crossdressing before seeking work at a neighbor's house where new possibilities emerge.
A sissy white bitch waits alone at his jewelry store, reminiscing about the Black Daddy who broke him in and left him craving more BBC.
A straight-appearing crossdressing man indulges his lingerie and anal fantasies alone in hotel rooms and at home.
A young boy recounts his privileged but turbulent childhood with his mother after his father leaves, the prelude to a life of sissy feminization.
A mother deepens her involvement in her son's feminization transformation, taking him shopping for feminine clothes and getting his ears pierced together.
A newly feminized sissy shows off her European makeover, new breasts, and stylish hair to an unsuspecting Tommy while casually discussing college plans.
A sissy struts into a popular bar in full feminine attire, commanding her sissy husband while catching the eyes of numerous interested gentlemen during happy hour.
A sissy white boi meets a well-endowed older Black dom at a club after a week of online flirtation and shared fetish fantasies.
A young sissy boy's anal initiation continues through encounters with his great-uncle, school prefect Rob, and Rob's divorced father who shares a panty-fetish and takes a keen interest in training the feminized boy.
A 20-year-old gay man recounts his journey into sissy feminization and sexual submission, beginning with early fantasies about taking the female role during sex.
A self-described sissy stays home in lingerie and panties, instructed by his girlfriend to wank while she goes out cheating on him.
A young schoolboy visits a shabby old cinema seeking encounters with older men interested in submissive panty boys.
A crossdressing young man is tricked by an older friend into giving him a forced blowjob at the mall.
A curious sissy bottoms meets a dominant daddy type from Craigslist for the first time, navigating nervous anticipation during their initial in-person encounter.