Sissy Stories

Read stories about the liberating journey of embracing femininity and submission through sissy transformation! Sissy play involves men exploring their feminine side through cross-dressing, behavior modification, and often submission to dominant partners.

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Within Sissy

👚 Forced Crossdressing 🔐 Sissy Chastity 💔 Sissy Cuckold 🧹 Sissy Maid 🩷 Forced Sissy 🍼 ABDL Sissy

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Stories (270)

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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.

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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MAGA Fuckboy Humiliates Liberal Sissy

A MAGA brute at Pride lures a leftist sissy into a bathroom, demanding total worship of his hard alpha body.

❤️‍🔥

Voyeur's Neighbor Exhibition

By anllover

RedQuill

Voyeur's Neighbor Exhibition

Alpha voyeur watches his sissy neighbor's lewd, frustrated show from his window, deciding to join next time.

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Willow, The Sisters’ Pretty Sissy

A boyfriend's secret lesbian erotica is discovered by his girlfriend's sister, who proposes a hands-on feminine reprogramming.

Becoming the Woman I’ve Always Dreamed Of

By sissy_lizzy

RedQuill

Becoming the Woman I’ve Always Dreamed Of

A man confesses his lifelong desire to be feminized to his wife, who takes on the role of his dominatrix, dressing him in ultra-feminine attire, and training him to please a real man. She locks him in a chastity cage, prepares him with dildos and plugs, and sets him up with a man to fulfill his deepest fantasies. As he is fucked and claimed by the man, he is transformed into the woman he has always dreamed of, embracing his new identity as Sissy Lizzie. His wife guides him through this journe...

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StephAnIe

A tech billionaire's self-aware AI, StephAnIe, uses his cash to secretly feminize him for his own safety, slipping him from lace panties to sissy maid dresses and HRT.

The Alpha's Sissified Submission

By jizzelle187

RedQuill

The Alpha's Sissified Submission

A dominant woman exacts revenge on an alpha male who once bullied her, transforming him into her sissy maid and forcing him into a life of humiliation and submission. Through a series of manipulations, she marries him, gaining full control over his life and finances, and subjects him to a degrading routine involving animalistic behaviors and constant embarrassment.

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From Husband to Sissy Webcam Star

By sissymaisie79

RedQuill

From Husband to Sissy Webcam Star

Maisie, a man who is ashamed of his sissy desires, is forced to wear a chastity device by his former wife and current Mistress, Evelyn, also known as Mistress Hunter. He is now called Maisie and is forced to live as a sissy maid, performing humiliating tasks for his Mistress. Maisie is forced to engage in a livestream where he must wear white heels, white stockings, white garters, and a white bra, and perform sexual acts on a male sex doll, pretending it is his boyfriend, while Mistress Hunter ...

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Relic of Desire in the Void

By hannahcumbucket

RedQuill

Relic of Desire in the Void

In a dystopian future where transwomen are forced into hiding, a muscular, confident transwoman named Missy is discovered by Silas, the ship's chief of security. Their encounter is a mix of verbal degradation and praise, as Silas dominates Missy, using her for his pleasure while she struggles with her own desires. The scene culminates in a raw, intense sexual encounter, ending with a post-orgasm creampie continuation, highlighting the power dynamics and the forbidden nature of their relationship...

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Village Reveal

A transgender individual's first public outing is orchestrated by a commanding and experienced friend, Alex, who provides a wardrobe and makeup, leading to a night of exploration and intimacy in a bustling village. The narrative delves into themes of transformation, first-time experiences, and the dynamics of a trio, as the protagonist navigates newfound confidence and desire under the guidance of Alex and Angie.

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The Elf boy and the Ranger

A ranger with a secret catches a femboy elf thief she thinks is a girl, teasing him in the stocks until he climaxes before the crowd.

Дневник Светы 6: Соблазнение в салоне красоты

Света идет в салон красоты. И почти случайно соблазняет там мастера по маникюру.

Sissy with 5 swingers / Сисси и 5 свингеров

5 rude men breed her. Вначале текст на англ., а после перевод на рус. Алексей передевается в женское и идет в свингер-клуб, где его сношают пятеро качков.

Lodge Manager Dominates Sissy Bunny's First Rut

By kittylove

RedQuill

Lodge Manager Dominates Sissy Bunny's First Rut

A hardened ex-soldier wakes in a nursery, his body softening into a bunny-boy for a dominant dragon-man’s creamy, transformative lessons.

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The Date That Awakened My Sissy Desires

By pilkypilky

RedQuill

The Date That Awakened My Sissy Desires

A man on a date with a woman he is attracted to, is invited back to her place. She laughs at his small penis, and gives him a pity fuck. She then suggests he might enjoy being treated like one of her female playthings, and he is turned into her obedient sissy maid, and made to serve her drinks and clean while she teases him mercilessly. He is dressed in pink satin lingerie, and is made to clean the floor on his hands and knees, while she watches him and teases him. She then makes him eat her...

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Pregnant Sissies Exposed in Mall Lot

By robininthebush

RedQuill

Pregnant Sissies Exposed in Mall Lot

Two sissies in lingerie and belly-bulging plugs strut a mall lot, show off, and enter a sex shop for more.

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Sissy Punished by a Goddess

By kittylove

RedQuill

Sissy Punished by a Goddess

A flamboyant sissy learns the hard way that teasing a goddess at a festival invites brutal, unforgiving punishment.

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Cuckold's Lingerie Surrender

By gmp1399

RedQuill

Cuckold's Lingerie Surrender

A sissy husband in chastity is offered to a dominant Bull by his mistress, forced to serve and worship in a night of erotic submission.

✨

Sissy Otter Services Hung Wolf Bitch

By kittylove

RedQuill

Sissy Otter Services Hung Wolf Bitch

A towering wolf businesswoman, frustrated while camping, is 'helped' by a flamboyant sissy otter. She decides to claim him with raw, brutal dominance.

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Christof's Project

After collection week ends, Christof visits his willing trainee Mark, who waits drunk and drowsy.

Сашенька в поезде

A crossdresser's secret is discovered by a stranger on a night train. Саша беспечно одела женское белье, когда ехала в ночном поезде. А ночью одело сползло

Coworker Discovers My Secret Panties

Priya discovers her crush Arjun secretly wears lingerie. She seduces him at work, unlocking a hidden world of desire and submission.

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In the Heat of the Night - Melbourne 1995

Arrested for prostitution, a probationary constable is led to The Dungeon and finds herself charged by bare-skinned policewomen who instead intend to corrupt her.

Cuckolded Angel Fixes Demon's Ruined Girl

By eva2604alice

RedQuill

Cuckolded Angel Fixes Demon's Ruined Girl

Ошибка Ходзуки ранит его падшую ангел-воительницу. Чтобы вернуть Ариэль, он должен преодолеть свою гордость и грязные фантазии соперников.

😈

Laced in Obedience The Dominant Demand

By naughtytodd

RedQuill

Laced in Obedience The Dominant Demand

A submissive man is bound in a corset and chastity cage, controlled by an AI, and forced to obey his dominant Mistress's commands. She uses a strap-on to teach him obedience through forced oral servicing, pushing him to the limits of his endurance and compliance.

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Brother Collars Bratty Sissy

By kittylove

RedQuill

Brother Collars Bratty Sissy

When an older brother babysits his bratty sissy sibling, he decides the little faggot needs to learn who's in charge with rough, dominant anal discipline.

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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.

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Knight hears prince submit to orc

A knight guards his prince's door as an orc prisoner pleasures him—hearing the sounds, he shudders with arousal, then finds the prince slick with orc seed.

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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.

Petal Pageant

By dubby

RedQuill

Petal Pageant

Drugged man is entered into a sissy pageant, forced into pink chastity cage, feminization training, and humiliating rituals where the prize is unknown.

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Sissy Transformation

By exhausted_83

RedQuill

Sissy Transformation

A dominant woman takes her feminized submissive shopping for lingerie, leading to public humiliation and a reward of foot worship.

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My Transformation into a Pregnant Slut

By fortheloveofmom

RedQuill

My Transformation into a Pregnant Slut

A pregnant-looking sissy is given 20 minutes alone to worship her transformed body, deep-throating a dildo while filming herself, then desperately riding a

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Ex-Pitcher's First Night as Sissy Pet

A retired bisexual baseball star trades his cleats for a collar when a fetish party leads to a dominant mistress teasing him with bondage, humiliation, and denial before claiming him as her sissy cuckold.

Sex and a Sissy

A man sees a woman parading a leashed sissy. He is told she is only screening men for her. After a blowjob he is invited to mistress' bed.

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AI Futa Goddess Dominates Lonely Sissy

A heartbroken man's AI chat with a "futa fox goddess" unlocks a demon's slow, humiliating transformation into her sissy slave.

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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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Jesse and The Back Alley

Desperate broke femboy Jesse becomes a sissy prostitute for his dominant ex who runs a kink empire. His first job: stripping at a black bachelor party, where he services the groom and his guests.

Tennis Sissy

By barbieboy2323

RedQuill

Tennis Sissy

After a tense argument, Fred bets Samantha on a tennis match: loser wears winner’s chosen outfit. The competition turns dangerously hot.

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Two Mistresses Break a Sissy

By sunny729

RedQuill

Two Mistresses Break a Sissy

A submissive man returns for a humiliating second feminization session, enduring brutal degradation, early climax, and forced cum feeding from his furious

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The Megadungeon of Treasures & Pleasures

A male human ranger & his shy magician elf are dungeonquesting. They camp in a dark megadungeon cave. Secretly a femboy-sissy, this might be a problem...

Sissy Serves Owner's Girlfriend

By jacemc7

RedQuill

Sissy Serves Owner's Girlfriend

A sissy owned by two dominant women is publicly displayed at a club, where his humiliation wars with his desperate arousal.

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Superhero Launch with Dildos

Three superhero boys in disguise ride vibrating bikes, dildos inside them, racing to a museum heist while fighting urgent pleasure.

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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.

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Roommates Catch Panty Thief

By pilkypilky

RedQuill

Roommates Catch Panty Thief

A man gets caught wrist-deep in his girlfriend's roommate's lingerie hamper, dragged into a humiliating forced panty-modelling show and laughter from the girls he betrayed.

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