A young guy curious about men meets a dominant older stranger from Craigslist to explore submission and anal sex for the first time.
#sissy
62 stories tagged with this.
A husband offers his wife to an alpha neighbor while being forced to dress in women's underwear and submit to humiliating servitude.
A frustrated straight man encounters a sissy prostitute outside an adult video arcade and gives into cruel curiosity.
A sexually confused young sissy recounts his journey into homosexuality and feminization while wandering city streets seeking sex from strangers.
A self-described sissy prostitute solicits anonymous men in adult video store arcades, offering oral, anal, rimming, and other degrading services.
Part 3 chronicles a sissy's brutal fist-fucking conditioning, enduring escalating anal punishment while wearing ballet boots, ball weights, and stretched nipples.
A teenage babysitter discovers a porn tape while snooping through his married neighbor's belongings, setting him on the path toward sissy training under his headmaster.
Jamie's submissive cuckold training continues as his dominating wife Karen invites a friend to play.
A sissy femboy eagerly services his drunk father with oral and watersports while fantasizing about anal.
A muscle-bound jick pushes his meek, feminine-looking best friend into a wild sorority party that escalates into sexual coercion and sissy feminization.
A young engineer at a birthday party finds himself being drawn into a sissy training scenario by a dominant woman.
A man wakes up after his first night of full sissy submission to his mistress, who prepares to deepen his training.
A man's life is transformed when he's held captive and feminized by a couple with a penchant for black cock.
A transvestite's first days of sexual freedom lead to a wild party and unexpected encounters.
A confident woman takes control of a powerful corporation and her new slave's life.
A sissy's first encounter with a dominant man leads to a night of intense pleasure and submission.
A young man explores his sissy side and gets taken by multiple mature men in a gangbang.
A man rediscovers his love for porn through the lens of sissy hypno videos, leading him to explore his sexuality in public.
A mid-40s sissy meets a 24-year-old black man for a raw, intense hookup that leaves her begging for more.
A former football player shares his journey of self-discovery and sexual awakening as he embraces his feminine side and experiences the joys of being a 'sissy'.