A young college student meets an older couple and is instructed to wear lingerie and service the wife while her husband watches.
#crossdressing
480 stories tagged with this.
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.
A young boy who secretly wears women's clothing discovers transvestite websites and fantasizes about becoming a girl, leading to exploration with a male friend.
A teenage boy secretly obsessed with transgender porn is discovered by his neighbors and forced into feminization against his will.
An 18-year-old virgin meets an older man he found on Craigslist for his first sexual encounter.
A teenage girl discovers her younger brother posing as 'Samantha' in crossdressing porn photos, recalling a slumber party where her friends pulled him in to join.
A 17-year-old boyfriend agrees to dress as a cheerleader for his girlfriend's Halloween dorm party, leading to shaved legs, silicone breasts, and an unforgettable night.
A closeted bisexual husband uses his family's weekend away to invite a black couple and their male friend for group hotel play while dressed in feminine lingerie.
A young soldier home on leave in the late 1960s experiments with his mother's lingerie, ignites a passion for corsets and stockings, and encounters an older man in a public toilet for his first sexual encounter.
A crossdressing father and his stepdaughter's long-running arrangement takes a darker turn when his teenage son discovers their secret nighttime games.