Sissy Stories

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Sissy

by rogue01 on Sep 19, 2017
Fetish

Sissy It happened at last that he was caught. His wife came home mid-afternoon with her friend Miriam and found him upstairs in the bedroom wearing a pair of her panties. Her reaction shocked him. In the hot instant of his overriding shame he was aghast to discover in her a persona he had not yet known existed. Him, a faintly domineering man, like so many...

Sissy

by TxRad on Sep 14, 2017
Mature

I came in from work about noon on Friday. I had been gone for a little over two weeks. Pulling in the driveway, I noticed that my daughter's car was gone but her best friend's car was parked in front of the boat on the far side of the carport. You talk about a pair to draw to; those two were it. My daughter is tall, dark, and slender, Sissy is even taller, b...

Sissy

by lil_nikki;) on Apr 3, 2015
Transsexual

BEEP BEEP BEEP Your alarm goes off, you quickly reach and hit dismiss on your phone. You look at your phone, its 8:00, and then you grin as you realize it's your birthday. You jump out of bed, naked as can be, and walk to your bathroom for a shower. You stop on the way to look at yourself in the full length tri-mirror that's just outside of the bathroom.What...

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Sissy

by mikedoreilly1973 on Apr 22, 2025

It was late friday night, and Mike had just gotten home from work, he was tired and filthy from work and decided to take a much needed shower, he went to the bathroom and noticed the door was slightly ajar, he peeked inside and saw his 18 year old daughter Samantha taking a shower. Samantha was his daughter from his previous marriage which had ended badly wh...

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Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...

Sissy Chantel, New Reality Ch. 10

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Ten: My First Saturday and Sunday as They are Special Days For Us. "Wake up girls." as sissy Traci calls out to us. We all rise from our sleep and another day in our sissy maids, sissy sluts lives begins. Just like in the previous days starts we spend our time with a morning enema, shower, shave and makeup. We get dressed but not in any maids out...

Becoming a Sissy Maid & Slut Vol. 05

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Prefix: A continuation of my sissy maid and slut journey. I hope you all do enjoy my unfolding story here. I am writing further chapters with hopes to give you all a semblance of some of my sissy ideas and thoughts so that these may excite you as the reader. I will try hard to keep each chapter on an exciting flow of what I feel may be life of a full time si...

Becoming a Sissy Maid & Slut Vol. 14

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twenty Three: Sissies at Work, Sissies as Sluts at the Farm. 4:00am and the alarm clock goes off. We three sissies must wake and begin our day of long, hard labour of degrading sissy maid and sissy slut work. Off comes our sleeping lingerie and soon three naked with only our chastity devices dangling on our sissy dicks we must quickly and together s...

Becoming a Sissy Maid & Slut Vol. 13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twenty Two: Satin, Ruffles and Lace, Sissy Maids contracted out to Work. Monday morning and I arise as typical at 7:30am, enema, shower, shave do my makeup and put on a maids dress for the day. Today it's back into a black satin one. Master told me though to put on black back seem pantyhose for today which I dutifully do and make sure the seems are...