#transvestite
102 stories tagged with this.
A crossdressing college student is caught in schoolgirl attire by his uncle and his Water Board coworkers, leading to a coerced group encounter.
A bored straight college man stumbles onto a provocative pop-up that triggers a sexual awakening and a journey toward transforming himself into the women he desires.
A teen cross-border caught stealing lingerie is confronted by a large male security chief who discovers her secret.
A crossdressing bi man in a hospital gown flirts with a female nurse and male nurse while secretly wearing lingerie under his robe before back surgery.
A college woman embraces her bisexual and submissive desires, exploring group encounters and adventurous sex with a wide circle of friends.
A man in a coffee shop is approached by a strikingly beautiful person whose deep voice hints that 'Allison' may not be exactly what she appears to be.
A sissy husband living as a woman is tasked by his mistresses to find and dominate a male lover, converting him into a panty-clad sex slave.
A young man recounts a memorable Halloween party night in L.A. County with coworker Glenn and his girlfriend Julie, involving costumes and unexpected encounters.
A young military man visits his separated triplet siblings and mother, leading to an erotic reunion involving crossdressing and group sex.
A young man's longstanding fantasy about his favorite aunt involves crossdressing, domination, and forbidden desire.
An autobiographical account of a male-to-female transgender person preparing for a date after work, documenting the process of becoming Ashley.
A closeted crossdresser prepares himself in lingerie and a maid outfit, eagerly anticipating service and punishment from his returning mistress.
A 17-year-old crossdresser shares his secret hobby with his male friend, leading to mutual bisexual exploration and anal sex.
A man stays with his secretary's older friend in the country, leading to a steamy encounter between the three.
A teenage boy experiments with his sister's clothes, shaving, and a sex toy to fulfill his fantasy of becoming a girl.
A cross-dressing husband secretly explores his submissive and lingerie fantasies at home while hoping his dominant wife will one day discover and embrace his true nature.
A 19-year-old discovers his 14-year-old neighbor crossdressing in secret and uses the leverage to coerce sexual favors.
An autobiographical account of a boy discovering crossdressing and sexual pleasure in feminine clothing from age 7 onward.