Long Transgender Sex Stories
The longest transgender sex stories on the site — slow-burn reads of 2,500+ words for when a quickie isn't enough. Browse all Transgender stories →
Every story we've published, in one quiet list. New ones land at midnight.
My Boxing Partner's Stocking Cock
Alex's boxing partner reveals her stocking cock.
Studio Couch Swap
Ravi transforms shy crossdresser friend in lace.
First Time with a CD in Cumberland
A curious 32-year-old guy has passionate first-time sex with a 28-year-old crossdresser in a Cumberland motel.
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.
Last Night In The Studio
Dante catches his feminine assistant dressed.
Stormy Beach House Swap
shy crossdresser and trans neighbor swap beach house during hurricane.
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.
A Gay Man Sails in Lingerie
A gay man in pink lingerie gets bent over and fucked hard by a hot fishing captain.
Moonlit Pool: His Best Friend's First Surrender
Mark's best friend Petra, 29, finally surrenders her sissy body to him in the moonlit pool.
Bet Lost: Her First Claim on His Sissy Ass
Yara, 28, wins the bet and claims her eager 32-year-old roommate Cody's sissy ass all night.
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.
Harvest Moon Swap: Their Wives Eagerly Trade
Under the harvest moon, 42-year-old accountant Barrett eagerly lets his rugged 39-year-old neighbor Derek fuck him senseless as a sissy.
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.
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.
Climbing Wall Confession: His Roommate's First Feminization
Renata, a 26-year-old, gets caught by his 28-year-old roommate Darius dressed in sexy lingerie on their climbing wall and begs to be fucked as his pretty sissy.
Wedding Night Invitation: Their Best Friend’s First Feminization
A 28-year-old groom and his 27-year-old bride dress their 29-year-old best friend as a eager bride for a hot transgender threesome on their wedding night.
Neighbor's First Lesson
Shy crossdresser Nadia gets her first lesson from neighbor Gideon.
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.
Market Tease: Her Best Friend’s Secret Craving
Yara catches her 28-year-old best friend fully dressed in lace and begs to fuck him.
Darkroom Touch: Best Friends Cross the Line
In the darkroom, 28-year-old Dante watches his 26-year-old best friend Gwen finally reveal her transitioning body and they cross the line together.
Yacht Sparks: Best Friends Trade Dates for the Night
Best friends Theo, 28, and Sullivan, 26, trade dates for a hot night of feminization and raw anal sex on their yacht.
Tent Whisper: Best Friends Cross the Line
Best friends Paulina and Wesley cross the line when she dresses like his slutty girl in their tent.
Strangers on the Midnight Rails
A nervous crossdresser meets a hungry stranger on the midnight train and gets fucked senseless.
Reunited Craving: Her Office Party Sissy Surrender
Xavier, a 34-year-old executive, reunites with his 29-year-old trans ex Nadia at the office party and eagerly surrenders as her sissy.
Studio Muse: Her Older Student’s Secret Craving
A photographer transforms and passionately fucks his shy 24-year-old trans student in the studio.
Laundromat Glow: Husband Watches Her Claim His Wife
A 42-year-old husband watches a hot 29-year-old trans woman fuck his eager wife.
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.
Best Friend's Food Truck Confession
Best friends food truck hookup gets complicated.