A young boy who secretly wears women's clothing discovers transvestite websites and fantasizes about becoming a girl, leading to exploration with a male friend.
#dressing
634 stories tagged with this.
A teenage boy secretly obsessed with transgender porn is discovered by his neighbors and forced into feminization against his will.
An 18-year-old virgin meets an older man he found on Craigslist for his first sexual encounter.
A man's tender first intimate encounter with a trans woman, slowly undressing and exploring her body with passionate anticipation.
A teenage girl discovers her younger brother posing as 'Samantha' in crossdressing porn photos, recalling a slumber party where her friends pulled him in to join.
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 closeted bisexual husband uses his family's weekend away to invite a black couple and their male friend for group hotel play while dressed in feminine lingerie.
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 crossdressing father and his stepdaughter's long-running arrangement takes a darker turn when his teenage son discovers their secret nighttime games.
A curious married man meets an older man on a dark beach for his first gay encounter, which takes a surprising turn when his wife unexpectedly arrives.
An 18-year-old pantyhose fetishist at a park is approached by an older man who drugs him and seduces him into his first sexual encounter with another man.
A 19-year-old university theater crew member with a secret crossdressing and self-pleasure habit is caught by his imposing older professor in the dressing room.
A man loses a card game and becomes the sex slave to his wife and her female friend for a night of BDSM servitude.
A Daddy-dom and his feminized femboy play with praise, spankings, and anal sex in a lighthearted RP.
A shy crossdresser is discovered by his neighbor and initiated into sissification through tender but dominant lovemaking.
A man who secretly wears lingerie under his clothes visits an adult bookstore to explore his fantasies of being seen.
A closeted sissy slut in his late 20s meets an experienced online daddy who controls his wardrobe, orgasm, and daily obedience, culminating in a terrifying public task.
Max begins experimenting with crossdressing and anal sex with an older man while exploring a feminine identity that will later fully transform into Maxi.
In a dystopian matriarchy, a young man is purchased and forced into servitude by dominant women who rule society.
A crossdresser opens the door to two plumbers while dressed as a woman, leading to an unexpected encounter with the bi side of his life.