A 17-year-old virgin finally acts on his long-suppressed urges and meets an older man from Craigslist for his first gay sexual encounter.
#dressing
634 stories tagged with this.
A man waits on the stairs for a woman stumbling in from a night out, leading to a passionate and frenzied striptease encounter.
A teen boy uses his resemblance to his twin sister to trick his straight best friend into having anal sex with him.
A lonely young man revisits his cross-dressing desires and devises a scheme to seduce the handsome delivery worker who has captured his attention.
A teenage boy explores his sexual curiosity alone at home, discovering and using his mother's hidden dildo while confessing his forbidden fantasies about her.
A young man's secret crossdressing habit is discovered by a family friend who blackmails him into a drive with unknown intentions.
A young boy undergoes feminization and sexual training by a teacher and mother figure in preparation for an evaluative visit from a school principal.
After a Costa Rica getaway with Betty, Mina's dare with John leads to a sultry evening at the opera in a sinful silk dress and stockings.
A young college student meets an older couple and is instructed to wear lingerie and service the wife while her husband watches.
A novice sissyboy endures a harsh first session with two dominant men after being deflowered, as his training continues in a basement setting.
A married man struggles to resist returning to his 'Suzy' persona after a transformative weekend, as his wife eagerly encourages his feminization.
A boy wakes into a girl's body three months into a mysterious transition, struggling with unfamiliar femininity while preparing to meet family.
A teenage crossdresser living as a girl under her mother's encouragement begins home schooling lessons with an older male substitute teacher.
An autobiographical introduction to a male crossdresser's family background and early experiences exploring feminine clothing as a toddler and child.
A transgender executive specialist at a London firm navigates her identity and desires after work hours, retaining her male anatomy while embracing her femininity.
A self-described bisexual crossdresser recounts his earliest sexual experiences as a young boy, beginning with initiation encounters with neighborhood kids.
A teenage boy recounts his second sexual encounter involving anal play with two other boys in a makeshift playhouse.
A young man secretly explores sissy fantasies and hypnosis-inspired crossdressing before seeking work at a neighbor's house where new possibilities emerge.
A bullied sixteen-year-old boy discovers his father's secret interest in transvestites and begins a transformation into his alter ego Casey.
A teenage boy continues experimenting sexually with two older men, agreeing to wear silky women's underwear to please them.