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.
#crossdressing
480 stories tagged with this.
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.
A closeted bisexual coworker is caught crossdressing at his co-worker's place by her dominant partner, leading to an evening of enforced submission.
A 21-year-old meets up with an older man at a work-paid hotel for a night of shower play and sex.
A young man in his early years arranges his first face-to-face meeting with an older man he met online, eagerly anticipating being dominated.
A teenage boy who secretly likes to dress as a girl meets an older family friend who embraces his true identity and initiates him into his first sexual experience.
A husband secretly tries on pantyhose only to be caught by his coercive wife, who reveals a dominant fantasy of her own.
A 22-year-old crossdressing gay man posts on Craigslist seeking a dominant 'daddy,' gets stood up in a Walmart parking lot, and ends up being assisted by a tow truck driver instead.
A young college student discovers Tumblr's feminization community, posts an ad, and nervously meets his neighbor who turns out to share his sissy fantasies.
A young crossdresser enjoying a weekend alone in his mother's clothes has his fantasy interrupted by an unexpected alien encounter.
On her second day as a sex worker, Suzy accepts Kathy's wardrobe choices and heads to the workplace, still navigating the humiliation and excitement of her new identity.