#crossdressing
480 stories tagged with this.
A submissive crossdresser meets an out-of-town Dom at a truck stop and submits to brutal, humiliating public use.
A crossdressing college student is caught in schoolgirl attire by his uncle and his Water Board coworkers, leading to a coerced group encounter.
A crossdressing man gets caught in a men's restroom by a fellow panty-wearing stranger, leading to an intense encounter.
A submissive crossdressing man answers an older man's call for a late-night bareback encounter driven by verbal degradation and forced oral.
A young man loses his anal virginity with his older male neighbor, who introduces him to toys, oral, and watersports in this autobiographical continuation.
A personal account of a lifelong latex fetish, from childhood discoveries with rubber gloves to a daily obsession with transparent catsuits and crossdressing in feminine attire.
An 18-year-old agrees to a birthday gangbang as his girlfriend's favor, ending up in full women's clothes servicing multiple men including his boyfriend's well-endowed brother.
A long-haul trucker dresses as a woman named Lisa for Halloween and embarks on a day of feminine adventure on the road.
A tomboyish teen reluctantly tries on a sexy black dress and heels at the mall under pressure from her friends, discovering she looks surprisingly attractive.
A person tucking and dressed femininely for a walk encounters a stranger who sees through their disguise, leading to an uncertain encounter.
A futanari college student continues her sexual adventures with sorority sisters who hatch a plan to disguise her as a man for a fraternity rush party.
A dominant wife and her equally forceful friend forcibly feminize and humiliate Don, dressing him as a woman and discussing using him sexually in public.
A trans woman dressed in masculine attire with a strap-on dildo picks up a redheaded woman at a lesbian club and invites her to dance.
A sissy 'panty boy' accompanies his strict mistress on a business trip to New Orleans, secretly wearing crotchless lace panties to please her.
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.
Eric surprises his boyfriend Jack with pink nylon panties after a homemade dinner, leading to intimate foreplay on the couch.
A woman meets a man online who loves trying on her lingerie and admiring himself in her undergarments.
A young man secretly wears women's panties to his older boss's office, leading to a charged encounter between them.
Twin brothers explore a sexual relationship after one suggests they need experience, with the younger dressing in women's clothing for their encounter.