An autobiographical account of a lifelong crossdresser's early experiences with feminine clothing, makeup, and self-expression.
#dress
669 stories tagged with this.
A cross-dressing man is stalked home and violently assaulted by a mysterious stranger who intends to use him as a sex toy.
Peter, a self-described cock-hungry bottom, is pimped out by his handler Max to a group of men at a private pub function while dressed as a sexy secretary.
A sissy named Peter explores their feminized identity through anal encounters, culminating in a night with a fellow cross-dresser named Tonia featuring mutual oral and preparation for anal sex.
A 14-year-old crossdressing teen recounts his summer of sexual encounters with various men and women.
A high school senior distraught about an upcoming military move finds comfort in a passionate encounter with his girlfriend Jenny at a friend's party.
A crossdressing wanderer in rubber attire encounters a werewolf in the woods in this Little Red Riding Hood reimagining.
A female art student hires a handsome male model who flirts with her, leading to a mutual unveiling.
A transformed Tim is presented to multiple male partners in a schoolgirl outfit for an evening of group play.
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.
A smooth-bodied bisexual man recounts his descent into crossdressing, exhibitionism, and submission as he seeks out men online to use him.
A man accepts his friend's bet to dress as a woman and is surprised by how convincingly feminine he appears.
A young man discovers his fascination with trans women and crossdressers, leading him into a kinky group encounter that pushes his boundaries.
A crossdressing teen captive in a vampire's lair uses seduction to try to escape his monstrous guards.
A stalker flies in early, spies on his target at work, then uses a staged photo to blackmail them into a blindfolded sexual encounter.
A fair-skinned 14-year-old boy, who enjoys secretly wearing his mother's underwear, becomes infatuated with his brother's black friend King and fantasizes about exploring their attraction.
A teenage boy's long-running voyeuristic obsession with his beautiful neighbor Barbara turns unexpectedly when she finally notices him.
After a wonderful fifth date, a woman finally invites her chivalrous suitor inside for an intimate and passionate evening together.
A young man secretly explores his crossdressing fantasy while his sister is away, but the situation spirals into female domination and blackmail.
An 18-year-old recounts a tender evening with his younger muscular boyfriend, with hints of crossdressing play and intimate moments.