A bisexual man in a schoolgirl uniform and heels visits a notorious English cruising spot to find hung tops for anal encounters.
Trans
137 stories.
A teenage boy pursues his longtime crush Lucy, but when she's unavailable he ends up exploring something unexpected with her effeminate younger brother Jack.
A young man is mistaken for a woman by his elderly aunts and must humor them by presenting as female while staying in their conservative home.
A young crossdresser moves into his own flat and prepares for his first public outing dressed as a woman, recounting his sexual experiences leading up to meeting Joe.
A nervous crossdresser invites an older guy over, dresses in a schoolgirl outfit, and experiences anal sex for the first time.
A crossdressing man ventures out in feminine attire for the first time and ends up having sex in a public toilet.
A crossdresser fantasizes about visiting an adult store while publicly passing as a woman after months away from the thrill of her secret outings.
A young husband spends his wife's business trip dressed in her clothing, exploring the thrill of feminine presentation and self-pleasure at home.
A 15-year-old crossdresser explores his sexuality alone at home while his mother is away.
A crossdressing teen explores her bisexual side at a wild house party with her sister's boyfriend and his friends.
A teenage boy tries on his best friend's sister's panties and outfits for the first time, sparking excitement about what it feels like to dress as a girl.
A man dressed in women's clothing eagerly awaits a delivery man for a repeat encounter involving oral sex, only to find the encounter unexpectedly transactional and disappointing.
A young man's secret crossdressing habit is discovered by a family friend who blackmails him into a drive with unknown intentions.
A 15-year-old boy, mocked at school for his feminine appearance, is left home alone when she visits her aunt, and begins exploring his transvestite side.
Kalynn confides to her mother about losing her virgin anal experience with the older Mr. Walker, and her mother reveals she uses sexual favors to advance her career.
An autobiographical introduction to a male crossdresser's family background and early experiences exploring feminine clothing as a toddler and child.
A 17-year-old boyfriend agrees to dress as a cheerleader for his girlfriend's Halloween dorm party, leading to shaved legs, silicone breasts, and an unforgettable night.
A young soldier home on leave in the late 1960s experiments with his mother's lingerie, ignites a passion for corsets and stockings, and encounters an older man in a public toilet for his first sexual encounter.
A man who secretly wears lingerie under his clothes visits an adult bookstore to explore his fantasies of being seen.
A self-described flat-chested man dons sexy lingerie and heads to an adult bookstore across from his hotel, fantasizing about being seen in his forbidden undergarments.