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.
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.
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.
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.
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.
Wife Unveils Hubby's Sissy Lingerie Craving
Wife catches hubby's sissy lingerie stash and pegs her into transgender bliss.
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.
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.
Sissy's Neighbor Discovers Her Silky Crossdressing Desire
Neighbor catches shy trans sissy in lingerie and claims her ass dominantly.
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.
Garage Mechanic Claims His Sissy
Rugged mechanic sucks and pounds a flirty trans girl's cock and ass in his garage.
High-Roller’s Hairdresser Kneels for Her Stocking Cock
A luxury hairdresser eagerly kneels to suck and get fucked by her wealthy trans client's stocking-sheathed cock.
Rained-Out Campout: Best Friends Share a Silky Stocking Cock
Best friends get soaked, strip down, and fuck when a rainstorm traps them together.
Best Friends' Brewery Confession: Years of Hidden Stocking Cock Desire
Best friends finally confess their lust when she teases him with her sheer black stockings.
Landlady Controls Her Shy Sissy Tenant
Landlady catches her shy college sissy tenant dressed in silky stockings and takes control.
Pizza Delivery Stud Claims Sissy
Sissy’s lingerie surprise turns her pizza delivery guy into a hungry fuck stud.
Pool Boy Worships Sissy Stocking Cock
Sissy socialite teases her young pool boy into worshipping and getting fucked by her wet stocking cock.
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.
Tattooed Bartender Seduces Sissy
Sissy gets her silky stocking cock worshiped and fucked by a hot tattooed bartender.
Vinyl Tease: Sissy's Tattooed Record Store Siren
Trans sissy gets bent over and fucked by the hot tattooed record store owner.
Real Estate Siren's Stocking Cock at the Masquerade
A curious guy gets seduced and fucked hard by a stocking-wearing trans realtor at a masquerade ball.
Best Friend's Rain-Soaked Stocking Cock
Best friends get soaked in the rain, and Jordan can't stop staring at Alex's hard cock straining against her sheer black stockings.
Rooftop Cinema Invitation
neighbor catches desmond dressed as a sissy.
Girlfriend's Panties Ignite Roommate's Sissy Lust
Roommate's secret panty try-on sparks his sissy submission to hot trans domme Jamie.
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.
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.
Studio Session Surrender
Reid hires trans neighbor Kiara for provocative studio shoot.