A shy teenage virgin who can cum repeatedly lives with his hot mother and aunt and soon explores crossdressing and sexual encounters with the two sex-starved women in the household.
#dressing
640 stories tagged with this.
A 14-year-old boy wearing his mother's shiny black tights under his jeans ends up alone in detention with an imposing male gym teacher, recalling his friend's warning about the teacher's locker room advances.
A teen boy is humiliated by his step-brother, who forces him to dance in women's clothing and call himself degrading names while secretly becoming intensely aroused.
A straight man stranded at a Spanish resort with only his wife's suitcase must wear her clothes and navigate unexpected feminization.
Tom loses his virginity to dominant Sam while dressed in lingerie and high heels, servicing his partner's dirty feet in a humiliating first-time encounter.
A young woman is drugged and dressed by her dominant partner before being taken to a Manhattan BDSM club called Lower Links.
Tom recalls losing his virginity and beginning a sexual relationship with his stepbrother, Sam.
Tom continues his confessional about being his step-brother Sam's girlfriend Tammy, with Riley's visit bringing new intensity.
A teenage boy recounts his lifelong fascination with women's nylon hosiery, from childhood sensations to being caught by his older cousin while raiding her family's laundry.
A man recounts his first visit to an adult theater wearing women's panties, where encounters in the dark lead to group encounters with other men.
A slim, petite young man with a panty fetish answers a Craigslist ad from a husky older man who wants a twink to dress in his wife's lingerie.
A 14-year-old feminine boy's first sexual experience with an older black man during summer 2001.
An older man seduces and gradually feminizes a younger boy, transforming him into his 'girly plaything' named Allison.
A first-person true-story recounting forced sexual initiation among three siblings left unsupervised by working parents.
A crossdressing advertising executive in NYC embraces life as "Heidi," secretly hooking up with men at gay bars while on business trips.
A young man finally acts on his lifelong fantasy of being dominated and feminized by a group of women after meeting a stripper.
A lover whispers "I love you" during foreplay, triggering an involuntary release that turns into passionate intimacy.
A crossdressing husband discovers his wife's infidelity through her cum-stained panties and becomes obsessed with tasting another man's seed.
A true autobiographical account of a person's lifelong journey into sissification and feminization, culminating in their first anal experience with a man.
A straight-acting guy recounts his evolution from childhood dare-games with his best friend into embracing a bisexual identity and occasionally crossdressing as a slutty 'guyrl' for male partners.