#dressing

A young white crossdressing teen in late '90s NYC chats online with an older Black man, exploring mutual attraction and shared lust.

A feminine man fully transforms into Ruby for a first night out, heading to a bar to explore life as a woman and sex worker.

A bi-curious sissy explores his newfound addiction to cock after losing his job, frequenting a GBLT club while reflecting on past encounters.

A close male friend wears a catholic schoolgirl outfit for his married buddy, leading to oral, anal, and exhibitionist humiliation as they venture into town.

A late-night knock brings an older cousin to the narrator's door just as he's dressed in feminine nightwear, opening the door to a long-buried family secret.

A sexually frustrated married man meets a younger man in a public toilet and they move to the narrator's home for intense oral and anal sex.

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 boyfriend agrees to crossdress as his girlfriend's date to a Halloween masquerade party, leading to unexpected encounters with other guests.

A self-described sissy stays home in lingerie and panties, instructed by his girlfriend to wank while she goes out cheating on him.

A continuation of the author's true account of being feminized and sexually initiated by an older boy over a transformative 24 hours.

A married man wakes up after a weekend of coerced sexual submission to his longtime male friend and wrestles with what their changed relationship means going forward.

A young sissy boy in lingerie is caught masturbating by his elderly neighbor who watches with his dog, leading to an unexpected encounter.

A 14-year-old boy dressed in feminine clothing solicits older male clients in a park at night to earn quick money.

A 14-year-old boy crossdresses and sells sexual services to older men on a park bench at night to fund his video game habit.

A crossdressing young man is tricked by an older friend into giving him a forced blowjob at the mall.

A blind groom reflects on his life with Heather as they consummate their marriage on their wedding night.

A young man's curiosity spirals from watching shemale videos into secretly buying lingerie, shaving his body hair, and experimenting with makeup.

In the swinging sixties, two possibly-related teens experimenting with each other in an attic take their physical exploration to a new level.

A black man nervously meets an older white trans woman from Craigslist for his first experience with a trans partner.