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.

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Femboy Prince Begs Jarl's Cock

By futanarisekai

RedQuill

RedQuill

Disguised as a wench, femboy Prince Arnbjorn seduces futa Jarl Brynhild in a mead hall, earning praise as her good boy while taking her thick cock in her lap.
Stranger Takes Me Blindfolded
A closeted male paralegal with a secret passion for cross-dressing sheds his work attire for satin and heels, slipping into a drag club where his hidden identity and nine-inch arousal collide in a monthly masquerade.
Sveta's diary 3: Misha asked to bring notes
A sissy named Sveta brings notes to Misha's dorm, knowing what he expects.
Husband in Stockings
A husband convinces his wife to let him crossdress, leading to a night of erotic discovery and new desires.
Path to Discovery
A guy discovers his roommate's ex left behind lingerie, leading to a challenge that blurs the line between curiosity and desire.

Fox Wife Debuts on Public Glory Hole

By killaa

RedQuill

RedQuill

Cross-dressing Naruto teases futa Hinata until she snaps, forcing him to serve anonymous cocks in a park glory hole, recording and locking fox ears per vot
Twin Sister Dresses Her Brother for Lingerie Party
A dominant twin sister dresses her submissive brother as her female twin for a lingerie party, blurring the lines of identity and desire.
daram's avatar
Trans Girls can love Girls too, my Coming Out
A trans college freshman tries on her first feminine sweater while her supportive ex-girlfriend waits outside, testing if she can become the girl she's always been inside.
whore for all its worth...
Mature crossdresser in need of money on the quest for true dirty whore experience.
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
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.

Boss Discovers Secret Panties in Supply Closet

By thunderhead28

RedQuill

RedQuill

A shy accountant wears a secret lace set under his suit at the office, but his sharp-eyed boss catches him alone in the supply closet.
Trans lover discovers latex kink
In a Shoreditch hotel, a man's secret latex collection is discovered by his Filipino trans girlfriend, who eagerly claims the boots and dominance.
Cruel Hearts
A betrayed acrobat transformed into a platinum-haired cabaret goddess lures his former lover into a seductive pas de deux, his supernatural beauty masking a heart forged for revenge.
Дневник Светы 3: Миша попросил конспект
A sissy named Sveta brings notes to Misha's dorm, Миша попросил Лёшу, чтобы Света принесла ему Лёшин конспект. Оба знают, чем это закончится...
photographer helps me transform
A business traveler confesses his secret crossdressing fantasy to a stranger on a flight—who offers to photograph the entire transformation.
Olivia's Travels
Oliver maintains a double life, using his corporate apartment five hundred kilometers from his girlfriend to secretly indulge his closet full of leather.
The Perfect Girlfriend
A stubborn gym-goer dons a cursed pink mask at a masquerade, slowly transforming into the perfect girlfriend while fighting his attraction to men.
My Girlfriend's Boyfriend Uses My Mouth
A lovesick guy agrees to be his crush's submissive, only to end up on his knees for her muscular boyfriend's daily blowjob.

Sissy Waitress Creampies Diner Slut

By nord140-a-259

RedQuill

RedQuill

A femboy waitress and a prostitute form a scandalous arrangement when a new Aunt Jemima arrives, igniting desires that shake up the diner.
Collared and Used for the Club
A submissive is bound and double-penetrated on a club stage, blindfolded and collared, as the dom and switch fucks her for the crowd's pleasure.
Backstage
Two rival drag queens compete for dominance backstage after a show, their playful power struggle escalating into a bold, passionate encounter when one makes the first confident move on his best friend's partner.

Husband's Sissy Retreat

By blackdagger655

RedQuill

RedQuill

A wife leads her husband to a kink retreat where he becomes her sissy, submitting to her and strangers' desires.
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
Bouncing Balloons & Double Plugs
Crossdressing Mickey in a blonde wig & chastity cage rides a pink balloon with a vibrating plug while sexy Minnie bounces on a red one, both locked in a breathless, bouncy rhythm.
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.
Tick-Tock: Whoopsie you're a peepee girl now
Two brothers mess with an old pocket watch. When the younger one's deepest desires and worst fears are revealed, he finds himself unable to resist a humiliating command that brings back his childhood shame.
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.
Lesbian Loves Her Girl Dick
A nervous trans woman meets a confident lesbian who adores her estrogen-changed body, leading to passionate discovery and acceptance.

Demoness Carries Femboy to Bed

By futanarisekai

RedQuill

RedQuill

A femboy bookstore clerk in a white Lolita dress catches the eye of a 6'6" demoness gamer girl when she enters his shop seeking a Victorian romance.
Command and Desire (completed)
Side Story. A meticulous and compassionate doctor, Adrian Korr, orchestrates a night of intense pleasure and submission with his lover, Agent Jared Blake.
Silver and Blood
A delirious femboy survivor, trapped by zombified friends, is rescued by a powerful woman who cradles his broken body and promises safety.
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.

Punk Best Mates Flip Fuck

By chantalsaproblem

RedQuill

RedQuill

Two punk friends trade new looks in their crumbling London squat; a deathhawk for platinum bleach sparks a rough, flip-fuck battle for dominance that could break their friendship.

Sissy School: Cum-Slut Training Begins

By shawnthebull

RedQuill

RedQuill

Mistress Ms. Creampie trains sissies in cum-slut duties: lipstick curtsy protocol, cock worship homework, and grading by Queen-Mom and Bull-Dad.
First Cruise, Full Femme
A newly graduated software engineer packs only femme clothing and breast forms for a seven-day Caribbean cruise, determined to present as his true self with no way to retreat into drab attire.

Bride's Best Friend Transformed in Her Lingerie

By alterman97005

RedQuill

RedQuill

A groom's best friend discovers the bride's wedding lingerie and is magically transformed into a woman, piece by piece.
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.
Best Friend Dresses Me Then Fucks Me
Drunken confession night turns heated when a 6'8" friend helps his 5'2" femboy roommate model an ex's clothes, leading to pantyhose and a desperate blowjob before a 40-minute ride ends in mutual cum.
Empath Femboy Finds Love Twice.
A psionic empath disguised as a femboy schoolgirl turns his seductive mind games on his hardened handler when a mission requires a deeper, more intimate kind of probing.
Stranger fucks skirt-clad slut in open hotel room
A stranger with a hotel key catches a crossdresser mid-fantasy, then leaves the door open while the man drops to his knees to prove how desperate he is.

Sissy QB Leads Teammate in Lingerie

By jeremy85

RedQuill

RedQuill

Closeted sissy quarterback in a black lace bodysuit leads his hunky teammate in a sheer babydoll into a dark bedroom at an after-party for their first kiss.

Union Man Reunites with Old Flame in Dress

By chantalsaproblem

RedQuill

RedQuill

Two striking young men, a cruel dock worker and a thieving beauty in disguise, collide in a seedy New Orleans bar, their flirtation a dangerous game of pride and arousal.
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.
Crossdressed DuckTales Boys Take Horse Cocks
Three crossdressing duck men in lingerie meet intelligent centaurs at a horse center, leading to a passionate encounter that unveils a hidden magical quest.
from elevator to heaven.
A traveling businessman hooks up with a tall, dark-voiced woman in a hotel elevator, only to discover she has a secret—and he has one too.
Dock worker reconnects with old flame in dive bar
In a rain-lashed New Orleans bar, a striking union dock worker reunites with a beautiful blond hustler who’s transformed into androgynous rocker glamour, igniting a barbed flirtation where both dominant men vie for control.