A teen cross-border caught stealing lingerie is confronted by a large male security chief who discovers her secret.
#gender-exploration
43 stories tagged with this.
A sissy sub eagerly returns to his transsexual Mistress Natasha for an evening of ball torture, forced cock-sucking, and feminized humiliation.
A young teen explores crossdressing and anal pleasure with his mother's dildos, fantasizing about oral sex with a real man.
A teenage boy experiments with his sister's clothes, shaving, and a sex toy to fulfill his fantasy of becoming a girl.
After wishing upon a shooting star to experience life as a woman, a young camper awakens transformed and begins exploring the unfamiliar reality.
A 15-year-old boy and his 12-year-old neighbor explore sexuality together through his father's porn magazines, revealing the narrator's crossdressing fantasies.
Two teenage boys explore crossdressing, feminization, and sexual intimacy together before one leaves for summer camp, with the narrator recounting memories and longing for September's reunion.
A slender, girlish nineteen-year-old slips into satin panties and a camisole before catching the train to surprise his older, kinky girlfriend.
A Japanese woman in a tomboy outfit at a bar helps her socially awkward guy friend practice talking to ladies, dropping hints for a hookup.
A straight man pretends to be a woman on a sex fantasy chat site and becomes fascinated with girl-girl encounters, eventually bringing his secret hobby into his workplace.
An autobiographical account of a boy discovering crossdressing and sexual pleasure in feminine clothing from age 7 onward.
A first-time encounter where a man in panties, bra, and pantyhose submits to a dominant male lover who pleasures and penetrates him.
A teen boy is humiliated by his step-brother, who forces him to dance in women's clothing and call himself degrading names while secretly becoming intensely aroused.
An autobiographical account of a lifelong crossdresser's early experiences with feminine clothing, makeup, and self-expression.
A 13-year-old trans girl on estrogen wanders a small town seeking a sexual encounter and meets an older black man interested in her.
Lois Lane is mysteriously swapped into Superman's body by Lex Luthor and must reconcile her new superpowered male form with her lifelong feelings of gender discomfort.
A cross-dressed man enters an adult cinema hoping to hook up with the horny guys inside for some group fun.
A crossdressing man invites a black man over on Thanksgiving night to fulfill his fantasy of being dominated and used orally.
A man finally indulges his lifelong fantasy of feminization by inviting a stranger to dominate and orally use him.
A crossdressing man ventures out in feminine attire for the first time and ends up having sex in a public toilet.