A seasoned crossdresser takes the plunge into paid escort work, meeting two clients at a hotel for her first booking.
Trans
137 stories.
A slender, girlish nineteen-year-old slips into satin panties and a camisole before catching the train to surprise his older, kinky girlfriend.
A thirteen-year-old crossdressing boy shares his story of losing his virginity to an older male neighbor in the mid-90s.
A male crossdresser enjoys a solo week at his parents' Palm Springs condo, indulging in shaving and feminine grooming before an encounter changes his life.
A 19-year-old discovers his 14-year-old neighbor crossdressing in secret and uses the leverage to coerce sexual favors.
A recently separated man recounts his love of shopping for sexy women's clothing at a charity thrift shop and his journey of self-discovery through crossdressing.
A 34-year-old crossdresser meets a 22-year-old man at Starbucks for a date, revealing fuller curves than advertised.
An autobiographical account of a boy discovering crossdressing and sexual pleasure in feminine clothing from age 7 onward.
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 secretly crossdressing married man arranges a long-awaited meeting with another crossdresser at a carpark rendezvous, building on their previous encounter.
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 first-time encounter where a man in panties, bra, and pantyhose submits to a dominant male lover who pleasures and penetrates him.
Two male roommates discover each other's crossdressing hobby and share an intimate moment of mutual revelation.
A crossdressing young man explores his latex and leather fetish with his two bisexual roommates while living together.
A confessional memoir-style account of the author's lifelong sexual awakening, from childhood voyeurism and panty fetishism through crossdressing and queer exploration.
A 30-year-old bisexual man visits a 51-year-old man's apartment wearing women's clothes for an intimate encounter.
A young male continues presenting as female while engaging in a sexual relationship with his stepfather, culminating in a violent punishment scene.
A male roommate secretly indulges his lingerie fetish by wearing his female roommate's clothes while masturbating, only to be caught when she returns home unexpectedly.
A man explores cross-dressing and gay sex with Jim after their first encounter, embracing feminine identity during their second meeting despite lingering fear and shame.
A divorced man embraces his lifelong fetish for women's lingerie and feminine presentation, indulging in solo anal play and public exhibitionism while passing as a woman.