An autobiographical account of a boy discovering crossdressing and sexual pleasure in feminine clothing from age 7 onward.
#transvestite
103 stories tagged with this.
A young man is tied up and dominated by his older partner Alice, who uses a large dildo to take his anal virginity while stroking him.
A married man secretly indulges in his longtime fantasy of wearing his wife's lingerie and bondage gear when she unexpectedly comes home early.
An older man picks up a younger woman at a bus stop and begins a relationship rooted in domination, submission, and his secret desire to feminize her.
A secretly crossdressing married man arranges a long-awaited meeting with another crossdresser at a carpark rendezvous, building on their previous encounter.
An isolated astronaut finds himself plagued by sinister, worm-like alien parasites that threaten to consume and transform him.
A crossdressing submissive recounts being forcefully and deeply taken by a muscular man while reflecting on his lifelong affinity for satin lingerie and femininity.
A young male continues presenting as female while engaging in a sexual relationship with his stepfather, culminating in a violent punishment scene.
A straight-appearing couple vacationing in Key West gets drawn into a bisexual group encounter at a transvestite club with another male couple.
A young babysitter crosses paths with a married man whose wife recently left him after discovering his affair with another man, leading to an intimate encounter involving oral sex.
A teenage boy is left home alone with his stepfather, who begins grooming him with feminine clothing and sexual preparation.
A woman discovers her roommate masturbates in her stolen panties, an illicit thrill that intensifies her lovemaking with her girlfriend.
A newly hired maintenance superintendent becomes entangled with a mother and her teenage child after agreeing to fix her bathtub drain.
A teenage boy working at a grocery store is drawn into a sexual relationship with an older male coworker who exerts a commanding influence over him.
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 transvestite teen eagerly gets re-fucked by his older boyfriend Sam, who dominates him roughly and makes him taste his own cum.
Tom continues his confessional about being his step-brother Sam's girlfriend Tammy, with Riley's visit bringing new intensity.
An autobiographical account of a lifelong crossdresser's early experiences with feminine clothing, makeup, and self-expression.
Peter, a self-described cock-hungry bottom, is pimped out by his handler Max to a group of men at a private pub function while dressed as a sexy secretary.
A young submissive male returns for his second encounter with an older dominant man who trains him as a slut, with a surprise third party introduced.