Anal Cum Sissy Stories

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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...

Caught in Panties & Dominated Ch. 04

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Cast Tracy -- me Tracey -- me, dressed en Femme Rick - head of security at work, had just caught me masturbating at work, dressed as a woman Ken - my roommate My ass was so sore. But he hadn't fucked me. Not yet... Earlier that night Rick made me his bitch. He took my sissy, lipstick-painted mouth, with his cock. He'd commanded my mouth, and he'd fill...

Master and Four Subs

by totk6432 on Apr 17, 2018
Fetish

This is a fantasy written by myself for fun. It contains spanking, humiliation and fetish; if this bothers you please seek other authors. All characters are 25 years old or older. ======= The rule is simple: I ring the doorbell and let myself into Master Daddy's house. Susan, my 25 year old personal assistant, is with me. She is in charge of me at work. Sh...

Mistress Commands Me in the Office Pt. 03

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

First a little clarification, if you've been reading parts one and two (I hadn't kept this quite straight up to this point). Here are the correct character names: Bob, or Robert, or Dick (or whatever my mistress decides to call me): Me Rick: My boss Brad: An office co-worker Rod: Office co-worker in an adjacent cubical, very buff, quite manly Wilson: Of...

Sissy Chantel, New Reality Ch. 02

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Two: If One was Fun, Two will be Better. Late night I get a call and I look to see that it is my new Master. I answer, "Hello Master Camron, how may I help you?" "Bitch ass sissy, I am gonna need you here tomorrow morning, by 10:00am." he excitedly replies. I reply, "Oh, ok I guess I can make it to your home tomorrow morning Master." "You God Dam...

Property of the Master Ch. 02

by BrightTightandWhite on Sep 26, 2017
Transsexuals & Crossdressers

"Wakey wakey sleepy head." The sound of curtains being drawn open was accompanied by a blinding light as my bleary eyes blinked open. "Wha... What? Huh? Hello?" I struggled to come up with coherent words as my brain wasn't fully awake yet. "Good morning Rosie, I hope you slept well," said the same voice as before. "Umm... Yes. Who are you?" I asked. "My...

Jack and Jill Pt. 02: Jean

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

It was two weeks later when Jean returned, it had been arranged that she would get there a couple of hours before Jill came home, to prepare him. He wasn't sure what to expect and he felt a mixture of excitement and anticipation. He followed her into the bathroom where she stripped him naked and shaved his entire body. He loved the smooth feel of his skin, e...

From Her Ex-Boss to her Bitch Pt. 05

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

This story includes extreme themes of sissification, interracial domination, watersports, cock sucking, if any of these themes are not your thing, please don't read it. ***** "I think you should have tattoo on your back above your pussy cheeks and another above your little Sissy clit." "But I couldn't do that Master, my wife would see." Amber was almost b...

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

A Missy Affair Pt. 02

by Stillherer on Jul 15, 2020
Fetish

I tried to carry on like my life was still the normal, everyday existence it had been. Beneath this facade of normality seethed the memories of Mrs Smith's parting words, "When the call comes for you Missy, you had best not displease us." I fluctuated between being terrified that the Smith's would out me and a seemingly incomprehensible desire for more of t...