Transgender Age Gap Stories

A married man's secret life as a sissy is exposed by a dominant poker buddy, leading to a journey of erotic humiliation and transformation.

Sal transforms into Salma at a T-Girls sauna night, surrendering to a marathon of tender and depraved encounters with older men.

A trans woman's journey as a sissy slut at a private club, exploring themes of submission, kink, and self-discovery, with a cast of dominant men and a journey of erotic awakening that will leave her begging for more.

A college boy crossdresses to expose sexism, but ends up in a steamy affair.

A 65-year-old executive 'Daddy' deflowers his 18-year-old trans assistant in a luxurious penthouse on her birthday.

A truck driver and his non-binary companion stop at a truck stop off US 36, where their Daddy-sissy dynamic unfolds in a steamy encounter.

A closeted transvestite's life changes when they respond to a contact ad and meet a liberating older queen.

A chance encounter reignites a long-held passion as a sissy falls for her former soccer coach, now a grieving widower, and becomes entangled in his complex family life.

A counselor's sessions with a troubled teen expose a web of illicit desires within an elite private school.

A retired man's secret life as a panty-wearing, cock-jewelry enthusiast unfolds online and in private.

When a ruined life sparks a journey of self-discovery, a 50-year-old man finds an unlikely 'daddy' in a 63-year-old stranger, and their forbidden love becomes a sensual escape.

When Alice runs into her childhood friend's father, John, at a game store, she can't resist the charming older man, and their chance encounter sparks a passionate romance.

A married cross-dressing man discovers his husband's nephew is not only aware of his secret but is also drawn to him, sparking a forbidden and passionate affair that changes their lives forever.

A chance encounter between neighbors ignites a passionate affair, while a young runaway finds love and acceptance in the unlikeliest of places.

A young man is seduced and manipulated into a life of subservience by a dominant man in rural Hawaii, forced to endure humiliating and degrading sexual acts.

A young trans woman's life is forever changed when she is taken in by an older man, leading to a complex web of intimacy, power, and identity.

A 40-year-old man seeking an older Dom meets a rugged 60-year-old retired trucker who promises to transform him into a 'stunning trophy housewife' in a journey of erotic submission and transformation.

Tricked into becoming a girl, Kandi navigates a complex web of erotic encounters and power dynamics.

A masculine bi man's life is forever changed when he meets Steve, an older man who introduces him to the thrill of cross-dressing and deepens their connection through affection and intimacy, leading to a night that shatters his boundaries.

A chance encounter at a gay bar ignites a night of unbridled passion and submission as an 18-year-old boy surrenders to the charms of a dominant black trans woman.

Two fat gay men in their 50s discover a shared passion for lingerie and intimacy at a conference.

A young sissy becomes the submissive wife of a retired colonel, dressing in feminine clothes and serving him with obedience.

A shy crossdresser becomes enthralled with a wealthy, dominant man and is drawn into a world of submission and control, forever changing their life.

A young trans protester's voice is silenced when she's detained by two corrupt cops with a very different kind of justice in mind.

A bullied high school student initiates a sexual relationship with his teacher, exploring power dynamics and desire.

A stressed college student meets a firefighter through a personal ad and gets fucked senseless in his car.

A young runaway's life is forever changed when an older man takes him under his wing, leading to a journey of feminization, exploitation, and complex emotions.

A trans woman and trans man share champagne, dance, and a passionate, hidden encounter on a crowded dance floor.

At his stepdaughter's 16th birthday party, a humiliated father and family maid is publicly disciplined for his transgressions, his degradation a twisted gift to the birthday girl and her friends.

A former law firm's ruthless managing partner is brought to heel by his wife, her lover, and their daughter in a tale of humiliation, degradation, and atonement, culminating in a shocking public display at a garden party.