A young man blackmailed into crossdressing and meeting a dominant older man at midnight, sneaking out of his family home in his sister's clothes.
#dress
661 stories tagged with this.
A young man explores crossdressing and anal sex before meeting a trans woman online who may help him begin transitioning into Jane.
A college-aged man is feminized and dressed as a schoolgirl by his dominant partner Audrey in preparation for an encounter with a special guest.
A teenage crossdresser is collared and enslaved by a group of painters, and must now explain his new life to his unsuspecting mother.
A college freshman dons a convincing female disguise for a fraternity initiation ritual, only to get in over his head when the disguise attracts unexpected attention.
A married man is coerced by his friend into wearing a schoolgirl outfit as part of an escalating fantasy arrangement.
A sheltered teenage boy is left with a friend's older brother and discovers new experiences with clothing and intimacy.
A young boy raised by his conservative grandmother discovers feminization and anal sex while being cared for by his friend's family.
A teenage boy dresses in his sister's lingerie and makeup to sneak out to a Halloween-themed party where he hopes to explore his secret desires.
A soon-to-be stepfather bonds with his fiancée's transitioning college-aged stepson over a snowed-in weekend, exploring themes of identity and forbidden attraction.
A bi-curious man abandons his local gay club for draggier venues and ultimately explores the back rooms of an adult bookshop with glory holes.
A mother deepens her involvement in her son's feminization transformation, taking him shopping for feminine clothes and getting his ears pierced together.
A tender, sensual encounter where one woman slowly undresses and orally pleasures another in a romantic, fantasy-tinged setting.
A sissy struts into a popular bar in full feminine attire, commanding her sissy husband while catching the eyes of numerous interested gentlemen during happy hour.
A man returns to his disciplinarian neighbor for another spanking, submitting to increasingly feminizing household chores as his price.
Two rival schoolboys whose mothers are called in to address their fighting must find an unconventional solution after repeated suspensions threaten their academic futures.
Two teen boys reunite when their mothers are away, finally consummating their longtime sexual tension.
A young white crossdressing teen in late '90s NYC chats online with an older Black man, exploring mutual attraction and shared lust.
A feminine man fully transforms into Ruby for a first night out, heading to a bar to explore life as a woman and sex worker.
A bi-curious sissy explores his newfound addiction to cock after losing his job, frequenting a GBLT club while reflecting on past encounters.