Best Transgender Sex Stories
The most-read transgender sex stories on the site — ranked by what readers actually pick. Browse all Transgender stories →
Every story we've published, in one quiet list. New ones land at midnight.
Cross-Dressing Sissy Meets Her First Man
A shy office sissy in a pink maid dress finally gets fucked by her online daddy.
Laundromat Forbidden Craving: Her Best Friend's Son
A divorced trans woman fucks her best friend's eager son at a late-night laundromat.
Neighbor's First Lesson
Shy crossdresser Nadia gets her first lesson from neighbor Gideon.
Wife Watches Husband Suck Transsexual Cock
Wife watches her husband eagerly suck two hung trans women's cocks.
Lila's Trainer Takes Her Sissy Cock
Sissy Lila's thick cock in vineyard stockings turns her hot trainer into a eager bottom.
My Wife's Silky Sissy Husband
Wife Tamara turns her eager husband into her silky sissy sex slave.
Best Friend's Father: Forbidden Hot Tub Surrender
Lila's forbidden hot tub hookup with her best friend's hot dad turns into a wild night of passionate sex.
Caught Skinny-Dipping: Her Stocking Cock Changes Everything
Caught skinny-dipping by his sister's hot trans friend, her stocking cock changes everything.
Mid-50s Straight Guy Discovers Trans Bar Pickup's Massive Cock
A straight divorcee gets his throat and ass pounded by a trans woman's massive cock.
Sissy's First Anal with Daddy
Simone nervously asks Darius to be her Daddy and take her anal virginity.
Girlfriend's Sissy Makeover Night Out
Girlfriend gives her boyfriend a full sissy makeover then takes him out to suck his first cock.
Sissy Training by Neighbor
Kiara, a dominant trans woman, catches her eager neighbor and gives him his first intense sissy training session.
Sissy Bitch Fucked Raw and Creampied
Marcus raw-fucks his eager sissy bitch and pumps a thick creampie deep inside.
Friends with Benefits: Crossing the Line on Her Yacht
Friends with benefits turns into rough anal sex when a hot trans woman pounds her guy on her yacht.
House-Sitting Heat: His First Time Taking Her Cock
Recent grad Warrick gets caught by trans woman Petra in her lingerie and takes her cock for the first time.
Hotel Bar Surprise: Straight Man Worships Her 10-Inch Cock
A straight salesman drops to his knees and worships a beautiful trans woman's 10-inch cock.
Business Trip Encounter
A straight businessman hooks up with a hot trans executive in her hotel room.
Sissy Hubby's Shiny Pink Lingerie Threesome
Wife makes her sissy husband wear shiny pink lingerie for their bull’s first threesome.
Double BBC Pound for Crossdresser in Lingerie
Simone the crossdresser in lingerie gets double BBC pounded by two hung Black guys while his trans girlfriend watches.
Rooftop Cinema Invitation
Neighbor catches desmond dressed as a sissy.
Crossdress Sissy Forced Pegging
Vanessa and Aisha turn their eager crossdressing sissy into a willing pegging slut.
Yacht Waves: Her First Time Taking a Sissy
Renata takes her best friend's sissy brother for his first time on a yacht.
Laundromat Glow: Husband Watches Her Claim His Wife
A husband watches a hot trans woman fuck his eager wife.
Wife Dresses Her Stepson as Femboy for Husband
Wife turns her stepson into a flirty femboy to surprise and fuck her husband.
Wife Unveils Hubby's Sissy Lingerie Craving
Wife catches hubby's sissy lingerie stash and pegs her into transgender bliss.
Manager's Private After-Hours Transsexual Orgy
Manager's steamy after-hours transsexual orgy with four eager 20-something performers.
Potion for My Chauvinistic Husband
A wife brews a potion that turns her chauvinistic husband into a woman for one wild night.
Storm Surge: The Widow's First Feminine Surrender
Widow Chloe lets her trans neighbor Yara dress her up and fuck her senseless during the storm.
Wife's Lover Puts Him in Chastity and Nylons
Petra's lover locks her husband Trent in chastity and sheer nylons, then makes him suck and get fucked.
The Emperor's Femboy Eunuch Harem
The emperor ravages his four eager adult femboy eunuchs in a raw harem gangbang.