Sissy Transformation Stories

Read Sissy Transformation stories from the RedQuill community.

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Being Dominated

A shy wife in a white sundress and her submissive husband attend a party where dominant Black men seduce them into exploring forbidden roles and long-buried desires.

My Girlfriend's Sissy Gangbang

A powerful CEO forges a lesbian relationship with a man, reshaping him through brutal feminization with her circle of female friends.

Mom Breeds Her Carrier Bimbo

Transforming into a bimbo, Doug desperately hides his infection from his mother before she discovers he’s meant to be a collared slave.

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Cuckolding Roommate Roulette

By yuanbl

RedQuill

Cuckolding Roommate Roulette

After his girlfriend becomes student council president, a college guy's drunken roommate party leads to secret balcony sex with his buddy's dance-major girlfriend.

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A bet gone right~

By nightskiye

RedQuill

A bet gone right~

A crossdressing university student wakes with chemically enlarged breasts and a flat chastity cage as two female classmates train him into their live-in sissy slave.

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A Modern Scheherazade

A husband gets caught with a stash of female underwear he wears in secret from time to time. This causes his wife, @Anna to investigate what else he is hiding. Finding his other secrets hidden in his electronics. His infatuation with erotica and porn of female domination, pegging, pussy worship and the act of shaving pussies. She comes up with a plan and with a few online orders puts her plan in motion. She will satisfy his hidden fantasies with stories and actions she can preform without che...

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Sissy Roommate's Surprise Welcome

By noobking

RedQuill

Sissy Roommate's Surprise Welcome

A college bottom transforms into a sissy to surprise his roommate, sparking a night of jealous passion and desperate submission.

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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.

Secretary and Widow Double-Penetrate Spy

A 1920s scholar infiltrates a secret suffrage society disguised as a woman, risking everything as its leader's dangerous grip tightens.

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Girlfriend Catches Sissy Panty-Sniffer

By pilkypilky

RedQuill

Girlfriend Catches Sissy Panty-Sniffer

My girlfriend discovers my lingerie secret and forces me into servitude for her and her bratty friends in the ultimate sissy humiliation makeover.

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Jock to Sissy

By missygurl1

RedQuill

Jock to Sissy

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

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Ванесса, новая солистка рок-группы

Рок-группе позарез нужна солистка. А кто ищет, тот всегда найдет. Шоу начинается...

Dominated by Her Cock

A crossdressing college student gets rescued from aggressive suitors by a dominant woman who reveals her secret and her own surprising anatomy.

Trucker Bertha Trains Sissy Boy

Young hitchhiker Tom accepts a ride from 48-year-old trucker Bertha, who gently teases his curves and trains him in sissy submission through oral worship and feminization.

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The Accidental Sissy Husband

A wife introduces her husband to pegging and hypnosis, unlocking his hidden submissive desires.

Byron Wears Kristi

By metrix4344

RedQuill

Byron Wears Kristi

Byron Noem secretly pretending and wearing a hyper realistic, rubber and silicone skinsuit of his wife, Kristi Noem. While she was off at the White House, being the head of the DHS, Byron would wear the lifelike bodysuit, looking, feeling, acting and being Kristi. He'd talk like her, walk like her, wear her clothes and use her makeup and hygiene products. He'd spend days at a time in the suit, with Kristi gone, and live life just like her, but inside their house. He'd cook meals, watch TV, work ...

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Boss Transforms Intern into Sissy Top

By adez

RedQuill

Boss Transforms Intern into Sissy Top

A boss transforms his intern into a sissy top, sending him to a sex-positive stylist who renames him Chloe, dresses him in lace, and reveals Marcus prefers flat chests.

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Sveta's diary 2: Дневник Светы 2: Маркус

Sissy Svetlana, craving her first black cock, dresses as a slut to seduce Cuban Marcus. Сисси-шлюха Света соблазняет кубинца Маркуса, чтобы попробовать BBC

Stepsissy

New stepdad and his dominant son move in, targeting feminine Cameron for sissification and submission.

Sorority Initiation: Sissy Slut

By dinomite7

RedQuill

Sorority Initiation: Sissy Slut

A shy college guy becomes the sorority's entertainment, transformed into a sissy and subjected to humiliating anal games.

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My Sister's Secret Substitute

Caught in her lingerie, a brother becomes his sister's dark substitute for her boyfriend's anal cravings.

Subservience Redux - sissy edition

A secret sissy buys a Megan Fox AI sex robot online. Weeks later, drunk and gooning, he opens the crate—only for Mistress Fox to lock a biometric shock collar on his neck.

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the fight of the small dicked futa

A futa faces losing her balls to the annual culling. With a tiny 6 cm dick and 7 classmates to beat in 9 months, she vents to a friend packin’ a monster 40 cm who never even worried.

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Gangbanged by My Bandmates' Hungry Tongues

By obsidiancat

RedQuill

Gangbanged by My Bandmates' Hungry Tongues

Cursed with a magically sensitive new body, Yoongi is immediately ravaged by his bandmates in a filthy marathon on the kitchen counter.

Gamer Boy's Secret Stream Seduction

A lonely gamer, frustrated by his failed streams, secretly transforms into a cat-eared girl online. His best friend becomes his biggest fan, showering his disguised persona with praise that ignites a thrilling, forbidden attraction neither knows is real.

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Breaking Nun

A nun in a black bikini tempts a rebellious heir by the pool, forcing his stepmother to choose between loyalty and forbidden desire.

Oiled Sissy Slut Begs For Cock

By whatever0208

RedQuill

Oiled Sissy Slut Begs For Cock

I'm kshitij, a 21 year old college student living in Jaipur. One day, i receive a mysterious package which contains a vial of water. I accidentally break the vial and the water spills over me. What i don't know yet is that this is the desi sissy slut virus that I now have. It gives me cravings which will gradually turn me into a complete sissy slut. The first chapter is about how i try to resist the cravings but slowly give in, first wearing bangles, then payals, then makeup, which i somehow d...

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CEO roommate trained as sissy slut

A confident executive signs a roommate agreement without reading it, only to discover the fine print forces him into hypnotic sissy obedience training and panty-wearing submission.

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12345678-11

By navi_oliveira_3

RedQuill

12345678-11

Enemies bound by a contract, a billionaire and a restaurateur engage in a brutal game of hate-sex where words cut deeper than touch.

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Jackies Journey - An X-Change Love Story

A goth guy discovers his mother transforms men into women with pills and finds a surprising ally in his stepsister's boyfriend.

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Submissive Sissy's First Time with Friend

By ashleyxcd

RedQuill

Submissive Sissy's First Time with Friend

A crossdressing husband moves in with his gay best friend, then appears in lingerie and heels, shocking him into a long-awaited first encounter.

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Breaking New Ground

By blackdagger655

RedQuill

Breaking New Ground

A wife transforms her husband into her bimbo, shopping for lingerie in public while preparing to share him with other men.

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Waking Up, Hungover, Wearing Lace Panties

Waking up hungover in a stranger’s bed, a man finds himself in lacy panties with faded makeup, realizing the naked, long-haired figure beside him might not be the woman he assumed.

Boardroom Gangbang

By jullius

RedQuill

Boardroom Gangbang

Leo exposes his cuntboy CEO boyfriend’s secret submissiveness to the entire board, humiliating him before unleashing their collective lust.

Wife's Friend Makes Me Her Lacy Toy

By dinomite7

RedQuill

Wife's Friend Makes Me Her Lacy Toy

When his wife leaves town, her best friend seduces him into wearing lace lingerie, then fists him into submission.

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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.

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Sissy Jay Gets Trained by Sienna

By siennasjay

RedQuill

Sissy Jay Gets Trained by Sienna

Sienna's blonde Australian cruelty cages six-foot Jay, then feminizes him with aphrodisiacs before coaxing her dripping sissy to serve femme Violet's cock.

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Fruit of Temptation

A bikini-clad nun tempts a billionaire playboy at a California pool, testing his stepmother's warning to behave.

But, but…….it’s too Big!

By anonydd

RedQuill

But, but…….it’s too Big!

Pantied Silas is caught by his uncle Bud, who seduces him with poppers and frot, leading to tearful first-time oral submission.

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Alone in a Hotel Room

By needy

RedQuill

Alone in a Hotel Room

A solitary businessman succumbs to chemical temptation in a hotel room, unleashing a mechanical, self-driven pursuit of raw, physical oblivion.

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The Doting Demon Fucks His Valkyrie

By alyona6931srov

RedQuill

The Doting Demon Fucks His Valkyrie

Хладнокровный демон Ходзуки влюбляется в падшего ангела Ариэль, чья темная сторона — легендарная убийца Персефона.

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Hozuki's Tender Domination of the Fallen Angel

By tom069gont

RedQuill

Hozuki's Tender Domination of the Fallen Angel

Hozuki, Hell's stoic administrator, patiently teaches the traumatized fallen angel Ariel to crave his tender touch instead of battle's harshness.

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Suzie's Sissy: My First Time as Her Bottom

A shy marketing guy is seduced by his dominant shemale coworker Suzie, who demands he become her sissy bottom and take her huge cock.

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Daddy's Femboy Training: Locked and Leaking

A shy college student is seduced by an older daddy into becoming his femboy Kitty, locked in chastity and trained to sissygasm on camera.

From Husband to Maid

A lazy husband is enrolled by his wife at a strict academy where he's feminized into a sissy maid, learning submission and service.

Husband in Stockings

A husband convinces his wife to let him crossdress, leading to a night of erotic discovery and new desires.

My Aunt's Sissy Training

A young man answers a dominatrix's ad, only to discover she's his aunt. She takes control, leading him into a world of submission and erotic training.

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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.

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