A mother deepens her involvement in her son's feminization transformation, taking him shopping for feminine clothes and getting his ears pierced together.
#crossdressing
479 stories tagged with this.
A sissy struts into a popular bar in full feminine attire, commanding her sissy husband while catching the eyes of numerous interested gentlemen during happy hour.
A man returns to his disciplinarian neighbor for another spanking, submitting to increasingly feminizing household chores as his price.
Two rival schoolboys whose mothers are called in to address their fighting must find an unconventional solution after repeated suspensions threaten their academic futures.
Two teen boys reunite when their mothers are away, finally consummating their longtime sexual tension.
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 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.