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 (256)

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Sissy Birdies Ride on Hopper Balls

Woody and Winnie Woodpecker, crossdressed in 2013 style, enter a pink room at "Sexy Birdy" agency, removing plugs and vibrators to ride and bounce on hopper ball dildos until climax leaves them gaping and spent.

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Ruby is my name, whore is what I am

A middle-aged husband escapes his stale marriage by transforming into Ruby, a submissive whore who hunts strangers for anonymous abuse in the woods and cheap motels.

Domme Fucks Submissive Sissy

By yaws1996

RedQuill

Domme Fucks Submissive Sissy

A caged sissy in a wet nightie is humiliated in the shower by her girlfriend, who forces her to admit she's just a tiny man pretending to be a girl before training her mouth on a 9-inch dildo.

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The sissy bombers' machine rhythm

In the early evening on Planet Bomber, the three boys are getting dressed in girly lingerie, makeup and wigs as they head to a scorting agency.

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Scott Takes a Sissy on the Beach

Scott approaches Veronica on a moonlit Caribbean beach, unaware she's a submissive sissy obeying her watching domme's command to surrender completely.

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*JD and Ethan - An All-Alpha Encounter

By mcamini992

RedQuill

*JD and Ethan - An All-Alpha Encounter

This story is told from JD's perspective. JD is a 19 year old 6’4” tall massively muscled Adonis with a movie star handsome face, tan skin, brown hair, blue eyes, and hard tight muscles. His pecs are especially large followed by incredibly wide shoulders and huge veiny biceps. His thighs are also hugely muscled and he has a high tight ass. He has a big thick veiny 14” cock and he's a bit of an exhibitionist. He is also bisexual and enjoys fucking guys as much as girls but he's a 100% top with gu...

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Tired of Waiting

After discovering her best friend's secret sissy desires, Stacy takes control, transforming him into her submissive girlfriend and buying him a new wardrobe.

Husband Transformed into Magicians Assistant

On a stale anniversary trip to Vegas, a struggling couple go to a sleazy magician’s show, unaware of the transformation he’ll go through

🌙

An Alp's Birth

By kitsundoll

RedQuill

An Alp's Birth

A sissy femboy witch curses himself with a sentient bondage prosthesis that edges his tiny cock forever, trapping him in a blissful, gooning hell of endless denial.

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Sissy Used in Gangbang Token Trial

By chubsissy87

RedQuill

Sissy Used in Gangbang Token Trial

A BBW domme forces a sissy to climb a humiliating leaderboard at her bathhouse, trading tokens for praise or degradation while stripped naked and modeled on a rotating pedestal for the crowd.

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Powerful Alpha Dominates Shy Math Teacher

By mcamini992

RedQuill

Powerful Alpha Dominates Shy Math Teacher

This story is completely legal and consensual. This story is about an 18 year old high school student named JD who has the hots for his math teacher Mr. Jameson aka Carl. JD is extremely good looking, 6'1" tall, weights 210 lbs of pure muscle, has extremely large pecs, biceps, shoulders, and thighs, and has an 11" dick. JD is extremely dominant and a pure alpha top. Mr. Jameson is 35 years, has a 140 lb slim twink body, is 5'7" tall, has a small dick, and has a round bubble butt and is a closete...

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Bear's Big Cock Tames the Sissy Skunk

By kittylove

RedQuill

Bear's Big Cock Tames the Sissy Skunk

A tiny sissy skunk meets a massive shemale bear on a blind date. Her blunt desire and his leaking arousal ignite a night of raw, size-difference passion.

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Sissy Boys Get Filled by Civilians

By thunderhead28

RedQuill

Sissy Boys Get Filled by Civilians

Three crossdressed duck brothers in chastity cages and butt plugs are hired out to anonymous clients, but the night takes a dangerous turn when their handlers reveal a hidden agenda.

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Husband's Sissy Exposed by Cops

By anllover

RedQuill

Husband's Sissy Exposed by Cops

Police search Michael's apartment, discovering his enema plug and chastity cage moments before Zander and two cartel giants arrive to breed his ruined hole

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Secret Sissy Exposed by Friends

By bear_btm_sub

RedQuill

Secret Sissy Exposed by Friends

Four married dads on a whiskey-fueled weekend getaway, until a strip-dare reveals a 40yo's secret chastity cage and panties—now a dominant dad takes control.

Sexy Birdy: Milking Session

By thunderhead28

RedQuill

Sexy Birdy: Milking Session

Crossdressed Woody and sexy Winnie work at Sexy Birdy agency, enduring a five-hour machine milking that pushes them to extreme limits.

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