A college-aged femboy named Allison shares his life story and sexual history with a younger male partner during an intimate encounter.
#crossdressing
480 stories tagged with this.
A husband caught wearing his wife's panties is ambushed by her and three female friends, who force him into feminine attire and take control of his sexual habits.
First-person confessional of a self-described exhibitionist detailing his solo hotel-room rituals involving nudity, crossdressing, and fantasy scenarios of being watched.
A Western man in Thailand enlists his two servants into a voyeuristic arrangement that escalates into group sexual play and shared domination.
A true autobiographical account of a man who discovers his submissive and transvestite fantasies after college, seeking female domination and torment through personal ads.
A husband is feminized, spanked, and forced to perform oral on multiple men by his dominant wife and her female friends.
Two pretty, girly boy musicians bond after a show, sharing pills and exploring an unexpected attraction in a hotel room.
A feminine-presenting girl pleasures a pretty blonde boy in a tender, sensual encounter.
A sissy husband living as a woman is tasked by his mistresses to find and dominate a male lover, converting him into a panty-clad sex slave.
A newlywed woman reluctantly attends her company fancy dress party dressed as Miss Whiplash, worrying about how much skin her costume will reveal.
A married man becomes increasingly consumed by his trans-female Dominant Natasha, surrendering to her feminization protocols while hiding his secret life from his wife.
A closeted trans woman in Berlin recounts her sexual awakening, from childhood crossdressing and anal experimentation with candles to adult encounters, framed as a quasi-autobiographical confession.
A young teen explores crossdressing and anal pleasure with his mother's dildos, fantasizing about oral sex with a real man.
A teenage boy discovered in his sister's clothes is seduced and taken by his mother's boyfriend who promises to keep his secret.
A young male swimmer relocates to rural Kentucky for grad school, ends up working at a trucker roadhouse where he begins crossdressing as a waitress.
A closeted bi teen crossdresses in his mother's lingerie and explores his sexuality with his best friend Chris.
An autobiographical account of a male-to-female transgender person preparing for a date after work, documenting the process of becoming Ashley.
An autobiographical gay tale tracing a Midwest farm boy's secret crossdressing and sexual awakening with other boys.
A 14-year-old boy exploring his newly discovered gay sexuality seduces a new kid at school for their first mutual sexual experience.
A closeted crossdresser prepares himself in lingerie and a maid outfit, eagerly anticipating service and punishment from his returning mistress.