Transgender Daddy Kink Stories

Vinnie and Taylor spend a day together, exploring Taylor's femininity and deepening their bond through intimate moments and shopping for more feminine attire.

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

A young Parisian's journey to Amsterdam sparks a transformation into Stéphanie, a softer, more feminine self, seeking love and acceptance.

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.

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.

A 38-year-old trans woman's life is forever changed by a chance encounter with a stranger, leading to a night of unbridled passion and self-discovery.

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

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

A crossdresser meets Bill at an Adult Video Arcade, leading to a dominant encounter and a dinner party invitation.

Tiffany's re-entry into the dating pool unleashes a torrent of kink, humiliation, and unbridled sex with multiple partners.

A young teen's summer of transformation and seduction unfolds with his cousin's guidance and a wealthy businessman's attention.

A cross-dressing man's Texas adventure turns into a wild threesome with two rugged railroad workers in a secluded spot near the tracks.

A widower's role as housekeeper for his stepson deepens into a complex dance of intimacy, identity, and desire.

A possessive daddy navigates a twisted dynamic with his twink boyfriend and his infantilized ex, as tensions simmer and boundaries blur.

A muscular stud's vacation turns into a wild group sex adventure with three hot daddies on the Brazilian beach.

A rebellious crossdresser hosts a 'daddy' for a night of rough role-playing that spirals out of control.

A software company owner's life changes when he meets a charming sissyboi at a party, sparking a intense and all-consuming relationship.

Pauly's life changes forever when their father discovers an explicit photo meant for a stranger, sparking a descent into incestuous submission.

A young FTM individual meets a bear at a gay bar and gets caught up in a intense threesome.

Ryan shares a hotel room with Jeff, his friend's dad, at a wedding, and things get complicated.

A 55-year-old cross-dresser, Mattie, meets Bluto, a bulky, bearded man, at Home Depot, sparking a flirtatious encounter that leads to a date.

A businessman and his new femboy assistant develop a charged connection that escalates into a deeply intimate and erotic relationship.

A young submissive's night with a much older man descends into a dark world of humiliation and degradation, leaving him questioning his limits.

A divorced man's life is turned upside down by his new 19-year-old Russian study abroad boarder's seductive feminine charm and slutty behavior.

Daddy's text gets me in lingerie and on my back, ready for a wild night.

A chance hookup in a remote industrial park leads to a cross-dressing encounter that blurs identity and intensifies pleasure.

College student Robyn becomes nanny and lover to her professor Dr. Taylor in a non-traditional family arrangement.

A young man is drawn into a web of control and exploitation by an older man he meets online, losing his autonomy and identity.

A 40-year-old man seduces a heartbroken crossdresser at a Halloween bar, leading to a rough, consensual night in a hotel room.

A father discovers his son's secret life as a 'Studio Boy' in Hollywood and becomes entangled in a taboo relationship.