New Transgender Sex Stories
The newest free transgender sex stories — fresh tales added every night. Browse all Transgender stories →
Every story we've published, in one quiet list. New ones land at midnight.
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.
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.
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.
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.
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.
Night Market Whisper: His First Surrender to Her
Shy 28-year-old Cody lets seductive 32-year-old trans woman Priya dress him in lingerie and fuck him senseless at the night market.
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.
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.
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.
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.
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.
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.
Stranded After Dark: Her Food Truck Secret
Stranded trucker Otto hooks up with hot 26-year-old trans woman Marisol in her food truck.
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.
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.
A Gay Man Sails in Lingerie
A gay man in pink lingerie gets bent over and fucked hard by a hot fishing captain.
Studio Muse: Her Older Student’s Secret Craving
A photographer transforms and passionately fucks his shy 24-year-old trans student in the studio.
Yacht Waves: Her First Time Taking a Sissy
Renata takes her best friend's sissy brother for his first time on a yacht.
Neighbor's First Lesson
Shy crossdresser Nadia gets her first lesson from neighbor Gideon.
Hot Tub With His Dance Teacher
Shy Emmett explores femininity with his trans neighbor.
Caught Skinny-Dipping: Her Stocking Cock Changes Everything
Caught skinny-dipping by his sister's hot trans friend, her stocking cock changes everything.
Reunion Flame: Her Silk Stockings Ignite His Sissy Craving
Xavier reunites with trans woman Harriet, whose silk stockings awaken his eager sissy desires.
Stormy Beach House Swap
shy crossdresser and trans neighbor swap beach house during hurricane.
Rooftop Cinema Invitation
neighbor catches desmond dressed as a sissy.
Last Night In The Studio
Dante catches his feminine assistant dressed.
Studio Session Surrender
Reid hires trans neighbor Kiara for provocative studio shoot.
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.
Strangers on the Midnight Rails
A nervous crossdresser meets a hungry stranger on the midnight train and gets fucked senseless.
Studio Couch Swap
Ravi transforms shy crossdresser friend in lace.