A 34-year-old crossdresser meets a 22-year-old man at Starbucks for a date, revealing fuller curves than advertised.
#crossdressing
480 stories tagged with this.
An autobiographical account of a boy discovering crossdressing and sexual pleasure in feminine clothing from age 7 onward.
A teenage boy on hormones from his stepdad embraces dressing as a girl and exploring sex with men, eventually turning tricks at an adult video store.
A husband submits to his wife's commands for a weekend, dressing in a maids outfit and performing household chores while she teases and controls him.
A man returns from vacation with his partner to launch a rescue mission for his former slave Sheila, discovering she has been thoroughly dominated and transformed by her new mistress Rita.
A bi-curious married man is blackmailed into sucking cock by a stunning Italian house guest, fulfilling a lifelong secret fantasy.
A secret crossdressing married man in a car park recounts his lifelong sissy desires, from wearing his sister's underwear as a teen to craving submission to dominant men.
A married man secretly indulges in his longtime fantasy of wearing his wife's lingerie and bondage gear when she unexpectedly comes home early.
A young bicurious man living with his roommate explores his taboo attraction to feminine, crossdressing teenage boys.
A young boy becomes a sex slave to a group of older guys after school, an experience that triggers his gradual physical and mental transformation into a girl.
A young boy is regularly subjected to petticoat discipline and public humiliation by his aunt and her circle of female friends in vintage photographs and paddling sessions.
A young blond twink discovers the pleasures of masturbation while secretly indulging in his mother's feminine clothing and high heels.
A man reflects on his lifelong fascination with the female body and contemplates transitioning into a woman after a pivotal sexual experience.
A secretly crossdressing married man arranges a long-awaited meeting with another crossdresser at a carpark rendezvous, building on their previous encounter.
A autobiographical account of a boy raised as a girl by his aunt, given hormones to feminize his body during puberty.
A drug-addicted young man, already exploring crossdressing, descends deeper into addiction and begins seeking paid encounters with trans women to fund his habit.
A straight man who secretly wears panties reconnects with an old friend and their mutual jerking sessions resurface, leading him toward exploring his trans identity.
A young crossdressing occult enthusiast takes shelter in a sinister cemetery, where his careless incantations summon a terrifying and lethal encounter.
A married middle-aged man secretly meeting a black man in a hotel for their first encounter, confessing his fascination with cocks.
A first-time encounter where a man in panties, bra, and pantyhose submits to a dominant male lover who pleasures and penetrates him.