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.
Laundromat Forbidden Craving: Her Best Friend's Son
A divorced trans woman fucks her best friend's eager 22-year-old son at a late-night laundromat.
Lila's Trainer Takes Her Sissy Cock
Sissy Lila's thick cock in vineyard stockings turns her hot trainer into a eager bottom.
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.
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.
Caught Skinny-Dipping: Her Stocking Cock Changes Everything
Caught skinny-dipping by his sister's hot trans friend, her stocking cock changes everything.
Neighbor's First Lesson
Shy crossdresser Nadia gets her first lesson from neighbor Gideon.
Rooftop Cinema Invitation
neighbor catches desmond dressed as a sissy.
Karaoke Afterparty: Best Friend's Silky Stocking Cock
Best friends turn lovers when Alex worships Kara's silky stocking cock.
Strangers on the Midnight Rails
A nervous crossdresser meets a hungry stranger on the midnight train and gets fucked senseless.
Yacht Waves: Her First Time Taking a Sissy
Renata takes her best friend's sissy brother for his first time on a yacht.
Wife Unveils Hubby's Sissy Lingerie Craving
Wife catches hubby's sissy lingerie stash and pegs her into transgender bliss.
Dare at the Lighthouse: His Best Friend's Stocking Cock
Bruno dares his crossdressing best friend Colette to model her sheer black stockings and gets worshipped.
Hot Tub With His Dance Teacher
Shy Emmett explores femininity with his trans neighbor.
Reunion Flame: Her Stocking Cock Awakens My Sissy Desire
At his reunion, a married guy gets seduced by his trans high-school friend into becoming her eager sissy.
Reunion Flame: Her Silk Stockings Ignite His Sissy Craving
Xavier reunites with trans woman Harriet, whose silk stockings awaken his eager sissy desires.
House-Sitting Heat: His First Time Taking Her Cock
Recent grad Warrick gets caught by 38-year-old trans woman Petra in her lingerie and takes her cock for the first time.
Cross-Dressing Sissy Meets Her First Man
A shy 24-year-old office sissy in a pink maid dress finally gets fucked by her 32-year-old online daddy.
Sissy's Neighbor Discovers Her Silky Crossdressing Desire
Neighbor catches shy trans sissy in lingerie and claims her ass dominantly.
Landlady Controls Her Shy Sissy Tenant
Landlady catches her shy college sissy tenant dressed in silky stockings and takes control.
Studio Session Surrender
Reid hires trans neighbor Kiara for provocative studio shoot.
Yacht-Bound Surrender: His First Taste of Her Stocking Cock
A curious straight guy gets seduced and fucked by a stunning trans woman's stocking-clad cock on a luxury yacht.
Tattooed Bartender Seduces Sissy
Sissy gets her silky stocking cock worshiped and fucked by a hot tattooed bartender.
One Last Harvest: Best Friend's Stocking Cock
Jake's best friend Dylan bends over in thigh-high stockings, begging him to taste and fuck his thick trans cock one last time.
Sissy's Handsome Houseguest Worships Her Silky Stocking Cock
Sissy's hot stepbrother's straight friend drops to his knees and worships her silky stocking cock.
Rooftop Afterhours: My Barista's Stocking Cock
Lena the trans barista catches her coworker staring at her stocking cock and fucks him hard on the rooftop.
Road Trip Surrender: Best Friend's Mother Claims Him
Priya, his best friend's 48-year-old trans stepmom, turns 22-year-old Ravi into her eager sissy on their road trip.
Garage Mechanic Claims His Sissy
Rugged mechanic sucks and pounds a flirty trans girl's cock and ass in his garage.
Burly Fireman Kneels for Sissy Stocking Cock
Burly fireman begs on his knees to worship and get fucked by his sissy neighbor's stocking cock.
Midnight Pool: Sharing My Wife's Stocking Cock With Our Best Friend
Mark and Chris take turns sucking and fucking his wife's huge stocking-clad cock.
Lake Cabin Surrender: Her Flirty Neighbor's Stocking Cock
Shy guy Roman drops to his knees for his flirty trans neighbor Yvonne's thick stocking-clad cock.