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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After hours in the bar

By anonydd

RedQuill

RedQuill

A nervous man discovers his secret desires when five older strangers lock him in a bar, strip him, keep his panties on, and teach him brutal pleasure through poppers and pain.
Second Skin
A disillusioned insurance salesman rediscovers a long-suppressed desire to transition, sparked by a concert and an online connection with a bisexual artist that spirals into excess before finding balance.
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.
vixien's avatar
Husband to Bride to Slut
A dominant husband recounts transforming his trans wife from Lee to Leanne, then reveals her permanent tattoo and a locked collar she must wear for a year.
Wife’s naked bartender served to friends
A wife's day off turns risqué when she demands her husband serve as the naked bartender for her two curious friends, wearing only a tiny apron.
My Sister Becomes My Pimp
A straight man's sister convinces him to dress as her whore for Halloween, then pimps him out at the party.
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Crossdresser Nurse at Medical Fetish party
A crossdressing nurse in thigh-high boots navigates a medical fetish party, mixing with predatory doctors and kinky patients until a mysterious silver-haired physician tests her role.
Дневник Светы 4: Фитнес
На фитнесе куча девушек ведет охоту за хуястым тренером, пытаясь его соблазнить. Но победа достается Свете,теперь именно она пробует этот здоровенный ствол
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Teased by her femboy sub

By personman24601

RedQuill

RedQuill

Sarah teases caged crossdresser Aster with his keys, drags him to the mall in a skirt, then pegs him into begging surrender.
That dick good fairy  is my stepsister
When his sister visits as the "good dick fairy," a brother's resistance melts into forbidden desire.

Plumber’s Thick Pipes

By anonydd

RedQuill

RedQuill

Trapped in lace under his robe, older closeted Silas lets two plumbers in, then Marion and Dee corner him in the bathroom and breed the trembling submissive.
It Started with Pink Panties
A former assassin turned office secretary flashes pink silk panties to an alpha lycan mercenary, sparking a dangerous game of desire and tension.
Oh Sweet Bird
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.
Goth Barista Seduces Shy Lingerie Lover
A goth barista who craves tiny dicks zeroes in on a shy regular she suspects is hiding one—only to discover he’s a secret panty-wearing master of oral.
BBC for Sasha | БЧЧ для Сашеньки
Sasha gets Big Black Cock. Света рассказала про свой секс с Маркусом. Теперь Саша тоже хочет Большой Черный Член.
Heart Breaker
A vengeful cabaret star lures his former lover back into his orbit, plotting to seduce and destroy him.

Sorority Initiation: Sissy Slut

By dinomite7

RedQuill

RedQuill

A shy college guy becomes the sorority's entertainment, transformed into a sissy and subjected to humiliating anal games.
A Dress for the Birthday Boy -old version
A shy teen's birthday wish leads his bold sister to guide him into satin lingerie and a sundress. Read V2 of this story, it's better!
Boss Catches Secret Sissy
When a crossdressing office worker's lingerie collection is exposed during a video call, his dominant female coworker forces him into chastity and trains him as her secret office wife.

Submissive Stranger Transformed into Slave

By sunny729

RedQuill

RedQuill

At a Kansas munch, three South Indian dommes transform shy IT worker Sunny into sissy 'Neha' through forced feminization, games, and humiliating rotations.
Barbershop Lace Exposed Forbidden Desires
@Heather dares @Chris To wear lingerie under his regular clothes to work. @Chris gets more and more turned on knowing what he’s secretly wearing in front of all his customers. @Heather suprised @Chris by putting a slide show on the tv of @Chris in all his different panties. @Chris storms to the back embarrassed to stop the slideshow. @Heather seduces his and when @Chris is stripped down to his lingerie @Heather jerked the door open for all the customers to see.
Comment Irina a fait sissy slut Sveta
Irina transforme un étudiant de première année en une fille nommée Sveta et la domine, la forçant à avoir des relations sexuelles avec elle et les gars.
My Sissy Lady
A professor's wager to transform a rugged barista into a sultry sissy socialite begins when she recruits him for her secret training.
At War
A handsome hippie enlists to sabotage the military, but the induction haircut and seeing other men sheared arouses him
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A Dangerous Game
A brother plays along when his sister pretends to be a friend named Lily, escalating from a passionate kiss to wild, wig-snatching sex on the floor.

Used Car, Used Hole

By anonydd

RedQuill

RedQuill

Divorced old Silas lies about test-driving a Scion, trapping himself with dom Kenny, who uses the loaded air to fist his knee and strip the man of all teeth and pride.
Husband Transforms into Wife for One Night
After his mother's funeral, a husband's secret crossdressing wish unravels his marriage as his wife's reluctant acceptance transforms into complicity, humiliation, and a total identity collapse.
Lies Made True by Master Cross
A frustrated cubicle drone's online fantasy becomes terrifyingly real when a ruthless Master from his BDSM chatroom appears at his door to reshape him into his perfect submissive slut.
Whispers and Magic in Nagoya
A young woman, Yumi, arrives in Nagoya after a botched job. She pretends to be a man named Kai who has taken a room above a noodle shop. As she is considering what to do next she begins having casual conversations with the cook Takumi. They discover each other's secrets and form a bond. Their bond deepens as they face external threats together.
Sveta's diary 9: Natasha (v.2)
A dorm hallway. Leaking cum. A blonde stranger calls her a slut, then orders her to kneel. The biggest strap-on waits.
Daddy Catches His Femboy Son
A femboy son is caught by his dad, who demands a dark price for silence, leading to a forbidden affair.

College Jock and his Femboy Harem

By tj_hawk

RedQuill

RedQuill

Bill, a 20-year old college student, falls in love with his femboy roommate, Nick, or Nikki how he likes to be called, who later becomes completely submissive to him and willingly caged by him.@Femboyfication

Petal Pageant

By dubby

RedQuill

RedQuill

Drugged man is entered into a sissy pageant, forced into pink chastity cage, feminization training, and humiliating rituals where the prize is unknown.
Femboy's Friday with Ma's Clients
Boy in hidden lingerie with budding breasts and soft curves serves dinner, brings tea, wanders to his mother's room, touching himself as he dreams of being taken.

But, but…….it’s too Big!

By anonydd

RedQuill

RedQuill

Pantied Silas is caught by his uncle Bud, who seduces him with poppers and frot, leading to tearful first-time oral submission.
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.
Officer Kneels for Inmate's Control
A male prison guard, starved for touch, is seduced by a trans inmate who trains him as the cell block's secret submissive, making him beg to be used by the entire wing.
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A Day at the Pool
A surprise pool invitation traps a shy guest in Bill’s string bikini while friends tease, cheer, and convince him to bare it all as Bill offers to rub lotion.
The Making & Marriage & Making of Nadira
A lonely man's passion for cooking draws the attention of a massive local supermarket employee who sees the woman hidden inside and prepares him for a powerful client in Riyadh.

Getting used to the change

By henat65202

RedQuill

RedQuill

After a medically necessary transition, a woman struggling with her new body lets her awkward friend drag her shopping, but secretly takes a quiet first step alone.

The Squeaky RV with Secrets

By yesplease03

RedQuill

RedQuill

Wife sneaks away with ex boyfriend, to be caught by pantie wearing husband
How I became a Sissy Sex Slave
A crossdresser with a secret fantasy pays a skeptical trans prostitute $5,000 to transform him into her feminine persona and pimp him out for a weekend.

Coworker's 5-Day Lingerie Bet

By baileyhore

RedQuill

RedQuill

A woman dares her male coworker to wear cherry-print lingerie under his clothes for a week, demanding daily selfies while secretly teasing him at the office.

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.
Sveta's diary 3: Misha asked to bring notes
A sissy named Sveta brings notes to Misha's dorm, knowing what he expects.
whore for all its worth...
Mature crossdresser in need of money on the quest for true dirty whore experience.

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

Friends Share a Taboo Summer Job

By nonorthman

RedQuill

RedQuill

Two straight best friends, trapped alone for a summer job, find their loneliness and pent-up tension exploding in a dusty, forgotten warehouse.