Crossdressing Stories

Read Crossdressing stories. Caught crossdressing stories: a husband in his wife's lingerie drawer when the door opens, a roommate who finds the stockings, a girlfriend who decides she likes him better in a skirt.

Stories (346)
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Woods Sissy Used by Many Men

By lordgrifis

RedQuill

RedQuill

The Femboy's Temptation

By bjojo7575

RedQuill

RedQuill

At an all-boys college, a male track athlete, Alex, heads into the team locker room, only to find a buxom coed named Sara, who happens to be a crossdressing enthusiast, applying makeup. Initially stunned by Sara's revealing outfit, Alex can't help but feel a strange stirring in his loins. As Sara catches him staring, she decides to tease him, unashamedly displaying her feminine curves and flirting shamelessly. Despite his initial confusion and embarrassment, Alex finds himself unable to resist S...
Best Friends Turned Lovers: Midnight Seduction
After years of friendship, two best friends surrender to forbidden desire in a rain-soaked penthouse, igniting a passionate night that changes everything.
Princess Trains Plumber in Gown Sex
A princess bets a plumber he can learn to fight in a ball gown, leading to intense training and an even hotter secret affair.
Heart Breaker
A vengeful cabaret star lures his former lover back into his orbit, plotting to seduce and destroy him.

Premature Ejaculation

By charliejustforfun

RedQuill

RedQuill

Overwhelmed by tightness, Carlos always finishes too fast, leaving partners frustrated. Now he seeks solitary relief where no one complains.

Roommate's Quarantine Therapy

By nonorthman

RedQuill

RedQuill

Locked down in a Christian dorm, two roommates' isolation ignites a taboo hunger that isn't for food.
Crossdresser and Two Strangers in Truck
A bold man in a dress trolls a mall parking lot, offering his first blowjob to multiple strangers, but the encounter quickly spirals beyond control.
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Wife's sissy husband serves her lover

By shawnthebull

RedQuill

RedQuill

Husband hesitates to clean his wife's creampie from her black lover. She forces him down. He begs to serve them both as their sissy cumdump and transgender nanny.
Kris and Chastity
Femme femboy Kris magically becomes his goth sister to seduce her neglected boyfriend Dario, planning car sex, oral, and anal during her weekend away.
Impudica Diva
In a private box at the opera Norma, a recently freed Marcel unleashes brutal sadism on Chouchou, his lilac gown pooling as he welcomes his cruelty.

Panther Helps Closet Sissy

By kittylove

RedQuill

RedQuill

A shy sissy alpaca is caught by a dominant panther mommy at a lingerie store, forced to submit to brutal anal training and embrace his inner girl.
Heroes Race in Lingerie
Aroused Sonic, Tails & Knuckles strip off their lingerie and butt plugs, locked in chastity, then bounce on huge dildo hopper balls in the dressing room.
Truck Stop Hookup Turns Threesome
A bold guy in a dress trolls a rest stop for his first blow job, but when multiple strangers accept, his risky fantasy spirals into an out-of-control encounter.
Sushi Wife in Dinner
A husband blindfolds his wife before slowly placing sushi across her bare skin, then worships each piece off her body with his mouth, building toward claiming her completely.
Sick Rose
Reunited with the man who abandoned him, a glamorous male siren seduces his ex-lover into a pas de deux of revenge.
Pink Ranger's Latex Training
A scientist ranger gets the pink latex suit and must learn to fight in heels and a skirt, with his teammate's help turning into a sensual lesson.
Crossdresser's First Night Out
A secret crossdresser finally goes out as Elena, meets Maya, and finds acceptance and desire in a bar.
Hearts Aflame
A vengeful cabaret siren lures his former lover into a pas de deux, intending to break his heart—but the performance reignites a dangerous, forbidden heat.
Glitter and Blood
A pretentious music journalist trades art rock for feather boas, descending into a glam metal band's sleazy underworld of drugs, makeup, and raw gay desire
Husband Transformed into Magicians Assistant
On a stale anniversary trip to Vegas, a struggling couple go to a sleazy magician’s show, unaware of the transformation he’ll go through
Swapped for Love
A new student's friendship turns possessive when Rajesh confesses he needs Jagan to become a girl, locking his chastity cage forever.

New Flat, New Hair, New Rules

By chantalsaproblem

RedQuill

RedQuill

Two punk art students from Manchester move to London, flip-fuck after Liam bleaches Les's hair platinum and Les buzzcuts Liam's.
Dirty
Factory boys turned punk occultists Liam and Les reunite at a Hackney house party, where Liam parades Les in sleazy lingerie, triggering a sadomasochistic ritual of humiliation, chaos magic, and long-buried desire.

Sick Rose

By vixien

RedQuill

RedQuill

Reunited with the man who abandoned him, a glamorous male siren seduces his ex-lover into a pas de deux of revenge.
Hearts Aflame
A vengeful cabaret siren lures his former lover into a pas de deux, intending to break his heart—but the performance reignites a dangerous, forbidden heat.
Star fall for secret (Actres and Crosdresser)
At an underground party, a butch actress feels unexpected lust for a femme stranger, unaware it's a famous drummer hiding his crossdressing hobby.
Reunion
Two punk icons reunite at a London club, trading dominance for a filthy bathroom brawl of submission and desire.
Mother and Friend Dress Ranma as a Sexy Doll
A mother and her friend turn a reluctant martial artist into their dress-up doll, parading her in revealing outfits and lingerie that awaken her hidden desires.
Ninja Girl's New Identity
An apprentice ninja uses a gender change potion to become Haruna, a curvy blonde bunnygirl, and infiltrates a strip club—only to face an unexpected oral audition.
New Flat, New Hair, New Rules
Two punk art students from Manchester move to London, flip-fuck after Liam bleaches Les's hair long platinum and Les buzzcuts Liam's.

New Flat, New Hair, New Rules

By madinlovewithgenet2

RedQuill

RedQuill

Two punk art students from Manchester move to London, flip-fuck after Liam bleaches Les's hair platinum and Les buzzcuts Liam's.

Sissy Takes Black Cock in Alley

By anllover

RedQuill

RedQuill

Chubby white sissy, locked in a pink chastity cage and dressed like a slut, gets ambushed by three hung Black men who degrade, grope, and brutally stretch his hole behind a bar.
Hearts Aflame
A vengeful cabaret siren lures his former lover into a pas de deux, intending to break his heart—but the performance reignites a dangerous, forbidden heat.

Mistress Transforms Submissive Man Into Neha

By sunny729

RedQuill

RedQuill

A shy Telugu IT guy submits to a strict Tamil Domme who transforms him into Neha, serving three Mistresses through domestic training, humiliation, and intimate surrender.
Sick Rose
Reunited with the man who abandoned him, a glamorous male siren seduces his ex-lover into a pas de deux of revenge.

Couple's Gender-Swap Weekend

By vexad72876

RedQuill

RedQuill

A millionaire wife dresses her husband in a sexy saree and lingerie at a private beach resort, then edges him against a glass window as they swap gender roles for a weekend of sensual exploration.

Wife Turns Husband into Pink Sissy Toilet

By rosybottoms

RedQuill

RedQuill

A wife discovers her husband's secret ABDL and crossdressing fantasies and plans a weekend of forced feminization, diaper use, and being used as a human toilet by her and her friends.

The Silk Boy

By hasoc48690

RedQuill

RedQuill

During Arcandros's war with Melanthia, Nivolad defies tradition to become a male service provider, discovering desire, identity and belonging.

Sexy Birdy: Milking Session

By thunderhead28

RedQuill

RedQuill

Crossdressed Woody and sexy Winnie work at Sexy Birdy agency, enduring a five-hour machine milking that pushes them to extreme limits.

Longshoreman's Temptation

By fraterbabs

RedQuill

RedQuill

A cruel, charismatic dockworker and a tough, androgynous blond petty criminal clash in 1980s New Orleans, where Dom’s sadistic need to pretty up Val ignites a dangerous game of dominance and desire.
Frat Pledge Gets a Girly Punishment
A college freshman's frat hazing leaves him naked and stranded, forcing him to seek help from his sister—only to face her roommates' cameras, borrowed panties, and an unexpected "sexy punishment.

Bleach and Blond: Collared

By chantalsaproblem

RedQuill

RedQuill

Two gay punk friends who've long crushed on each other move into a seedy London flat. Heated attraction and pride clash as two dominant tops flip fuck after a bleach job and buzz cut.

In Dreams

By vixien

RedQuill

RedQuill

Two punk boys from the factory floor reunite in a squalid London party—one dominant, the other craving ruin. Liam cages Les in cheap lingerie, parading him before the pack.
Bound and Transformed: The Stranger's Pet
A lonely husband's secret crossdressing and self-bondage ritual is interrupted by a mysterious stranger who offers to feminize him in exchange for total obedience.

Drag Queen Muscle Stud Seduces Bar Hunk

By dutch206

RedQuill

RedQuill

A musclebound bodybuilder secretly debuts as drag queen Miss Anita Benchpress in a tearaway gown, dancing until a stunned fellow lifter needs to meet her.

Hard Dockworker Flirts with Blond Crossdresser

By chantalsaproblem

RedQuill

RedQuill

A brutally handsome dock worker locks eyes with a androgynous blond in a tight blue dress, recognizing his old friend. The former petty criminal flirts back, both men challenging who will break first in a New Orleans bar.