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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Morgan catches gardener in panties
A closeted 56-year-old crossdresser mowing lawns is caught by his gorgeous 28-year-old client Morgan when his pink panties peek out as he bends over to clean his mower.
karencorset's avatar
Friend's Lap Dance Leads to Big Fun
A guy in a mini skirt, g-string, and wig gives his friend Bill a lap dance in gray sweatpants, then lets Bill's massive cock slip inside his ass until he takes it all.
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Chaos Magic and Cross Dressing Consequences
A witch's spell backfires, forcing four housemates to physically transform into the clothes they wore, unleashing five nights of erotic chaos.

Blacked Moving Day

By anonydd

RedQuill

RedQuill

@Massive cum Silas is an 18 year old virgin small pale And hairless with a small cock. He lives with his mom who happens to be out of town and they are getting ready to move so his mother tells him that she sent movers and these are corporate movers. They're gonna go in and pack up the entire house put it on a truck and then move everyone and then Silas will fly out to where his mother is now. The movers are three big black man one muscular one a little bit heavy set and then one truly fat he'...
Suite Life
A domme dresses her sub in lingerie, doses him with MDMA and a plug-ring, then alternates between his pounding her g-spot and her pegging him to orgasms.
Wife Dresses Husband as a Sissy
Humbled husband Scott loses a bet, so his wife Kim dresses him in a diaper and lavender dress to shop as proof of her superiority.
Shy "girl" discovers her hidden erection
A shy "girl" experiences mysterious arousal during class, then discovers a hidden erection that forces her to confront her true body.
[MTF]   The Gulf Disguise
A disgraced consultant flees Gulf authorities disguised as a veiled woman, then discovers his transformation unlocks possessive desire and erotic submissio
Dress-Up in Dungeon
A male adventurer descends into a cursed dungeon where mysterious gear transforms his body into a girlish form, each equipping step pushing him deeper toward a goddess's erotic trap.
Sam’s new assignment might just change him
A billionaire makes his assistant wear a maid's uniform for a gala, but the young man's shy obedience and hidden appeal in the short skirt make his stern boss crave more than just service.
How i became a strip club slut
A locked sissy risks everything at an underground strip club audition, where cage checks are mandatory and the manager's expectations go far beyond makeup and heels.
From Brad to Bride
College student Brad's stepsister can't make her wedding, so he must fill in as the bride wearing her fitted gown.

Three Daddies own me

By anonydd

RedQuill

RedQuill

A terrified virgin in secret lingerie is cornered by three predatory men who drug and restrain him, driving him toward a night of twisted submission.
Mysterious Mentor's Secret Seduction
A lonely divorcee rents a quiet annexe, unaware his silver-haired landlord plans to feminize him one silk-clad step at a time.
Tied up in the hen do: Связанный на девичнике
He was invited but didn't know for what... Девушки пригласили на девичник парня. Он думал воспользоваться ситуацией, но воспользовались им. Перевод в конце
ghost waiting for virgin man
4 men & 1 girl trapped in a haunted haveli. A ghost demands virginity. A priest reveals the only escape: lose it to anyone, even each other.
Cheerleader Ruins Her Tutor
A dainty tutor's confession to his cheerleader crush backfires when she confronts him in the locker room, revealing a devastating truth.
Secret Silks and Subtle Transformations
A wife secretly replaces her husband’s briefs with silk panties, then spends a year using quiet coercion to feminize him, until a stranger hits on him at a bar while she watches.
Superbowl bet.
A bet on the Super Bowl becomes a contract. Jake loses and must submit to his wife Krystal’s strap-on, her hidden fantasy now unleashed, as she secretly plots his feminization using experimental drugs.
Desperate fiancés modeling risk
Desperate fiancé Robert risks a mysterious modeling shoot for $20K to save his relationship, but the agency's erotic demands test his limits.

Closet Secrets and Slumber Surrender

By sonnycrockett

RedQuill

RedQuill

Tom is an 18 year old man who is caught peeping on his stepsister's slumber party. She makes him join the party!
Broken in at the club
A closeted trans, guided by an online DaddyDom, risks a swingers club's T-girl afternoon to shed her false marriage and finally become her true self.
storyjade's avatar

Roommates up the stakes in strip poker

By littlemissexulansis

RedQuill

RedQuill

Five college friends turn strip poker into a high-stakes game where losers either strip bare or don the winner’s lewd pick, with sexual acts on the table.
Me and Lady McB
An effeminate convict's prison haircut unleashes his brutal masculinity, attracting the desperate affections of effeminate prisoners
My Bestie, My Maid of Honor
When Kayla's maid of honor tries to seduce her fiancé, she kicks her out—then convinces her old friend Rich to become Rachel and take the bridesmaid's place.
Turning Tricks at the Park
A crossdresser cruises a dangerous park after dark, posing as a woman until a john forcibly takes him, using his mouth and then his ass.
The Bet Turned into a new Wardrobe
A husband bets his wife he can handle her wardrobe for a day, but her shapewear and heels awaken a hidden, desperate pleasure in being bound and dressed.

Jock to Sissy

By missygurl1

RedQuill

RedQuill

Homophobic jock Jay is blackmailed by girlfriend's sissy best friend Riley.

Husband's Secret Crossdressing Rituals

By ji4490398

RedQuill

RedQuill

A respectable married salesman hides a secret crossdressing life,indulging in forbidden fantasies when home alone.
Seduction in Silk and Shadows Unveiled
A closeted cross-dresser's secret life is discovered by his coworker, leading to a series of intimate conversations and a date that blurs the lines between Michael and his alter ego Karen. Rick's curiosity and acceptance allow Michael to explore his feminine side openly, culminating in a passionate encounter where Karen's true desires are revealed and fulfilled. The narrative delves into themes of identity, acceptance, and the erotic tension between a man and his alter ego, with explicit scene...
Stepmom Change the Will
After his father's will leaves Ivan sole heir, his furious stepmother Mrs. Shen plots with her lawyer to legally break the terms that disinherit her.
Client Fantasy A: College Girlfriend Disguise
A disguise artist transforms into his client's college ex-girlfriend with hyper-realistic prosthetics, to fulfill an impossible fantasy.
Ванесса, новая солистка рок-группы
Рок-группе позарез нужна солистка. А кто ищет, тот всегда найдет. Шоу начинается...
Samantha's Waxing Ritual of Forbidden Desire
A man, Ben, is captured and bound by a seductive, older woman, Samantha, who has a unique and painful fetish. She subjects him to a full leg waxing and a complete pedicure, culminating in the humiliation of wearing high-heeled shoes.
You wanted it, now you need it!
A man confesses his darkest fantasies to a therapist who weaponizes them, turning his secret need for smoking and feminization into an inescapable addiction she controls.
alogrette's avatar
My wife's pantyhose fetish ignites our wild bedroom
Caught by his buddies, the old joke becomes real: "When did you start wearing pantyhose?" "When my wife found them in my car"
The Fall of Jeanne de Valois
A disgraced noblewoman, branded a thief, must survive the brutal hierarchy of a 1786 Paris prison.
dilandau's avatar
Wife Commands, Husband Obeys
After a decade of marriage, Donna’s casual curiosity about having a cock sparks Jim to present her with a realistic strap-on, launching a power play that shifts their relationship into uncharted submission.
Curvy consequences of helping out a witch
A witch's enchanted shapewear transforms Bruce's body in his sleep, plumping his curves into soft feminine fullness.

Tsubaki Host Club

By amia

RedQuill

RedQuill

Tsubasa was always called a 'Boy' since her childhood but after a fight in her old school, she was sent to a private school but got misgender
amia's avatar
Submissive Husband Used as Toilet
A wife live-streams her submissive husband forced into a pink diaper and gag funnel, as he obeys her command to swallow strangers' piss and her own filth for an audience.
Reluctant Customer at Boutique
A rude customer insults a vintage boutique. The owner and her assistants teach him a lesson by forcing him into the frilliest dress, panties, stockings, and makeup—unlocking a secret submissive desire he can’t resist.
Laine's triumphant weekend
A high-powered wife returns from closing a mega deal, drugs her husband's scotch for endless orgasms, and spends the weekend using her sissy.
Sasha: Dressed and used before my date
A college guy's quiet Sunday becomes self-discovery as he secretly tries on panties and makeup, chasing the thrill of being Sasha for his first date.
daram's avatar
Another Night at the Park
Crossdressing by night, he cruises a dangerous park as a fake woman—until a real John takes him by force for mouth and ass.
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Maid for the Weekend
A 28-year-old poker loser spends a weekend as his girlfriend and her best friends' French maid 'Marcie', in lace lingerie, as their teasing praise makes him throb beneath the ruffles.
grimminessa's avatar
Wife Makes Husband Her Perfect Maid
When her unemployed husband turns lazy, a wealthy wife trades marriage for a contract making him her submissive sissy maid.

CEO Wife and Bratty Uke

By zakilla

RedQuill

RedQuill

An omega diplomat's past escapades ignite his alpha CEO wife's possessive jealousy, sparking raw confrontations and erotic reclamation.