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 (332)
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Classmate Discovers Chloe's Secret
A jock discovers his classmate Mike is secretly the stunning redhead Chloe—but that doesn't stop him from falling for her.
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.
The Borgias: Lucrezia's Lesbian Lover
A neglected Renaissance wife discovers passion with a female messenger disguised as a man, cuckolding her injured husband.
dilandau's avatar

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.
My Manager's Humiliating Stocking Rule
A mix-up with luggage and rooms leaves a married businessman wearing stockings and submitting to his dominant manager's control.
Genitalia portals , crossdressing
When a shy wife buys portal underwear, her husband's cock emerges from her crotch as her pussy opens on his belly, letting her ride them both.
Puppy Training for Hire
A teen femboy escort in a latex catsuit discovers a wealthy client who craves submission, leashing him like a puppy while controlling his chastity and finances.
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.
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
Who Will I Become
A lone adventurer dons a magical corset found in a dungeon, only to be transformed by its erotic power.
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
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.
Reunion
Two punk icons reunite at a London club, trading dominance for a filthy bathroom brawl of submission and desire.

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.
Sick Rose
Reunited with the man who abandoned him, a glamorous male siren seduces his ex-lover into a pas de deux of revenge.

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's First Night Out
A secret crossdresser finally goes out as Elena, meets Maya, and finds acceptance and desire in a bar.
Cosplay Connections
A mild-mannered reporter answers a cosplay team's ad, only to discover they need a female character. A talent agent sees potential in him—and the woman he's hidden inside.
The Muslim Master and his Hindu Slaves
A humiliated Hindu husband's three-inch failure drives his wife to fantasize about her tall Muslim neighbor while punishing her submissive spouse in their bedroom.
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.

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.

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.
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.

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.
Brother Pretends to be Mom to Save Sister
A young man poses as his mother to save his sister from foster care, but the disguise leads to an unexpected date with his former principal
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
Newcomer confesses his secret fetish
A support group for sex fetish addicts. A former sissy shares how the lifestyle consumed him, then shattered, at a meeting where escape is the only goal.
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.
Grieving Widow's Secret Exposed by Dom Daughter
A widowed father discovers his daughter is a dominatrix, then confesses he secretly wears his late wife's lingerie under his work suit, aching to serve as her French maid.
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.
Refugee Seduced by Drag Queen
A gay asylum seeker working a London KFC, terrified and invisible, finds his voice when he stumbles into a drag bar and meets queens who see past his fear.
Mouse and Minnie Ride in Denial
A crossdressing Mickey Mouse in lace, a chastity cage, and Minnie in matching lingerie share a kinky play session with butt plugs, strap-on dildos, and intimate dress-up.

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.
Daughter Enthralled by Dad's Femme Form
Ciara discovers burgundy lace panties that aren't hers. She secretly follows her mother and catches her father's gorgeous girlfriend wearing an identical pair.

Hypnotized Patient Craves Doctor's Control

By dupdup29

RedQuill

RedQuill

After a breakup, lost Etienne seeks therapy from John, who uses hypnosis to transform him into a sissy latex Catwoman slave, conditioned to obey.

Caught Crossdressing

By lordofpirates

RedQuill

RedQuill

A guy is hired to housesit for a wealthy neighbor women for a couple weeks. He stays at her expensive house and curiously snoops around. He finds her massive walk-in closet, and since he has a thing for crossdress, decides to try on some of her clothes. He puts on pantyhose, panties, a stuffed padded bra, skirt, and soft fuzzy sweater. While enjoying how he looks in the mirror suddenly she comes home early and catches him.