Sissy Hypno Stories

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Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

Sissy Fantasy to Nightmare

by Anon729 on Sep 16, 2017
Transsexuals & Crossdressers

My first ever story here so I would appreciate any feedback. Hope you enjoy it! ***** Sunlight drifted gently through the hotel room as I woke up and rolled over to feel the warmth of Rosie next to me. "Morning sleepy head," she greeted me with a smile. "No time to waste if you're getting ready for the stag." It was just 3 days until our wedding and the...

Sissy Whore Ch. 01

by DebbieDublin on Mar 7, 2018
Transsexuals & Crossdressers

I suppose it started as a game really. Born out of the frustration and boredom of countless meaningless encounters with nameless men from chatrooms who would call to my house late at night. Although each proclaimed themselves to be dominant, still none seemed to live up to my own expectations, leaving me drenched in their seed but ultimately unsatisfied. It...

Sammi Starts Camming

by Sissy_Sammi_ on Dec 3, 2017
Transsexuals & Crossdressers

Sam had always been rather small and feminine. As a guy puberty seemed to have missed him which left him in the rather uncomfortable position of being very girly. He was only about 5'8" with a womanly rounded face, smaller waist, and slightly larger hips. He had brunette hair, which for a guy was on the longer end. His lightly tanned white skin pieced with...

Sissy Girl Forever Pt. 03

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

Sissygirl forever continued. Sara stood there laughing at me as Mistress explained how things would be for the near future. She told Miss Andrea that if I wished she could fill them in with the red right now if I wanted. But Mistress said no. She was looking forward to my rushing off to work at times forgetting to polish them. Or eating out with friends and...

AliExpress and Sissy Downfall

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

It all started with a visit to a TV Mistress on a work trip, Charlie had been cross dressing in some way or another since he was a teenager. First just his Mums used panties, then a lodgers underwear and finally he'd started to buy the odd thing himself. As time went on, BDSM was added into the mix, Charlie realising he was submissive and when he found Siss...

Sissy's First Boyfriend

by kprice1984 on Jun 5, 2019
Transgender & Crossdressers

For those who have read my previous works Crossdresser's Unexpected First Time, thanks for your ratings! This story has a lot of true components, "based on real events", but is ultimately, fiction. ------------------------------------------------------------------------------------------ Since my first time with a man while I was dressed as a woman, about...

Jasmine - Sissy Slut Transformation Pt. 01

by BillyBaroo4you on Jun 1, 2020
Transgender & Crossdressers

A Sissy Cumslut Transformation Part I - The First Taste (of cum) Nervousness crept into his mind like a snake, slithering its way down toward his stomach. He felt scared, worried about the night ahead, worried about how this one night would change his young life forever. His gentle hands began to tremble as he applied the hot pink nail polish to his finger...

First Time Sissy - The Bike Path

by Phillysissylexi on Jun 15, 2020
Transgender & Crossdressers

My roommates had gone away on a trip for a week, so I had the house to myself for a few days. I had been waiting for a moment like this. As soon as they left I went to my closet to find all my girly clothes, toys, makeup, heels, and lingerie. I couldn't contain myself. I was so excited to turn myself into a sissy. I turned on some sissy hypno to listen to wh...

Introspection

by Sissy_Sammi_ on Jun 19, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. *** *All characters are 18+ years old ***** Jimmy was born into a small family in Colorado. His mother was a beautiful woman named Dianne, and his father was a gruff working man named Thomas. If only kids could have been given a choice to be born, Jimmy would have chosen otherwise. He...