Femdom, Sissy, Anal Training Stories

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Sissy Manners Classes Ch. 01

by fridaysissy on Sep 12, 2018
Transsexuals & Crossdressers

It was late night, I am 10 km away from my room waiting for sharing cab or auto service to reach my room at last I joined a sharing auto service with two members including me. The other passengers stop came early, and I remain alone in auto waiting for my stop to come. Driver said he is stopping the service and returning to his home and asked me to get down....

My Stroll outside the Car

by triffle64 on Sep 12, 2017
Transsexuals & Crossdressers

It was a beautiful evening in the spring of 1982. My wife and I were taking a drive up the coast of California for an evening stroll. She was driving. We had been married for about 5 years. She was 27, and I was 30. My wife is feminine, but she grew up as a tom boy. I had no idea that she would take so well to my submissive desires to be her sissy husband. T...

Be Careful What You Wish For

by ChainedToAKeyboard on May 12, 2020
Fetish

Author's note: This short story was inspired by Vitalis' amazing hentai artwork: "Bimbo Catalog: Bianca." * It was date night in the Whitley household and things were just starting to get exciting. Alice and Richard had enjoyed a lovely meal at a five star restaurant, a wonderful performance at the theater and a couple glasses of fine wine upon returning h...

Dinner Date with Mommy Pt. 02

by SissyStoryTime on Nov 20, 2018
Transgender & Crossdressers

Part 2 picks up right where Part 1 left off as Sophie prepares for the arrival of Victor. This story includes the following: Femdom, strap-on, implied forced-bi and cucking, enemas, butt plugs and anal play, feminization/sissification, spanking, CBT, humiliation, chastity, and domestic servitude. Enjoy! _____________________________ Part 2 Sophie was sl...

The Whore Wife, Sissy CD Husband

by MILF4black on Jul 27, 2020
Transgender & Crossdressers

This story is completely fictional. All characters in the story are over eighteen. Prologue: The Whore wife, Sissy CD Husband "That's it, you little sissy whore, suck that cock." Jennifer told her husband as his head bobbed up and down on the strap on dildo Jennifer was wearing. Her husband, Patrick, lifted his head and the seven inch fake penis slid out...

Splint's Humiliation

by justincbenedict on Dec 31, 2018
BDSM

Vince looked doubtfully at Splint, kneeling naked in the corner of his own living room. Then Vince turned his head back at Sparky, who smiled at him. God, watch her toss that ice blonde hair. When Splint began seeing Sparky, the whole crowd had been taken aback. Sparky was overweight in kind of a sexy way--big boobs, big hair all that kind of thing. Most o...

My Glorious Transformation Pt. 01

by switchhitter420 on Sep 18, 2017
Transsexuals & Crossdressers

My first stab at erotic literature, let me know what you think! Part one of a serialized fantasy journey into sissy faggotry. ***** About ten years ago, I ended a pretty serious, 1-year relationship with a woman I had met while working at a bar. She was this classic beauty: elegant, dirty-blonde hair, thin frame, striking facial features, an amazing ass an...

Miss A's New Play Thing Pt. 04

by Pornenthusiest on Mar 2, 2020
BDSM

Recap: Miss A had just finished a luxurious bubble bath and was returning to her slave who was chastised and gagged with her pantie hose and a ball gag, with Miss A's wetted panties draped over his nose. Locked away in her dungeon, after an arduous breath control play session, her slave was spread wide at the ankles with a spreader bar, bent at the waist wi...

Slave History

by timeagain93 on Sep 17, 2017
BDSM

These are my recollections of my slave history. Four Goddesses have dominated me. I'm writing this to let my current Mistress understand my story. Mistress D read "Variations" magazine and spanked me with a wooden spoon. She tied me naked to a chair and blindfolded me. She made me sit there in silence. I was wearing her panties while talking on the phone w...

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...