Sissy Enema Stories

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Loraine's Self Bondage Re-Creation

by loraineveritas on Mar 12, 2019
BDSM

The following is my re-creation of an event that happened a few years ago. I had been a sissy slave to Mistress Marie for over 2 decades during which I become a totally submissive slave to Her every desire. I think of Her often as She has passed now. While doing Self-Bondage activities shortly following Her passing my wild imagination conjures up the Mistres...

Neighbourhood Terror to Sissy Pt. 17

by Fibaro on Feb 3, 2020
Transgender & Crossdressers

Chapter 19 The drive back home was pretty uneventful, Lisa just sat behind the wheel smiling ear to ear. She had had an awesome day so far, making out with two gorgeous women and now she would spend some quality time with her sissy boyfriend. Marcy was very worried about that quality time. She hoped for sure that it wouldn't involve that dildo going up her...

Neighbourhood Terror to Sissy Pt. 19

by Fibaro on Apr 13, 2020
Transgender & Crossdressers

Chapter 21 John had been looking forward to this very moment that he wasn't about to just get it over with. He was going to savour it as much as he possibly could. These contacts proved to be such a good find. They allowed him to stay anonymous as long as he didn't give away his voice while still not covering the sissy's face. A face even John had to admi...

Humiliated Sissy Husband Ch. 02

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

Max was very busy hand washing all of Tonya's underwear and lingerie in the kitchen sink. He dipped a pair of her panties in the clean rinse water dunking them several times before twisting them and squeezing out the excess water. He then placed them in the clothes basket on the counter. Tonya insisted he wear 6" heels around the house especially when doing...

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...

Cucky Trained by CD DOM Pt. 03

by sndycd on Sep 15, 2017
Transsexuals & Crossdressers

"Gather your things, it's time to go." "Yes mistress." You got yourself together but I told you not to clean the cum off your face so you walked out of the theater and out of the store looking like the cum soaked whore you are. As we walked out I said, to no one in particular, "I hope you all enjoyed my whore. She'll be back." Another two block walk bac...

Dinner Date with Mommy Pt. 01

by SissyStoryTime on Nov 20, 2018
Transgender & Crossdressers

This is Part 1 of an update on the sissy Sophie and her cruel but loving Mommy, Amanda from the story Meeting Mommy (https://www.literotica.com/s/meeting-mommy) It contains numerous perverse and offensive themes that I'm sure you'll all eat right up. This story includes the following: Femdom, strap-on, implied forced-bi and cucking, enemas, butt plugs and...

High School Dilemma Ch. 06

by LaurenWestley on Sep 15, 2017
Fetish

(Authoress's note: of course all disclaimers are still in place regarding characters etc. PLEASE DON'T READ THIS IS YOU HAVE AN AVERSION TO PEE SCENES AND EXTREME HUMILIATION. This is only a fantasy story XXX+. I only wish there is enough here to make each of you happy. To those who have given me constructive criticisms as well as those with praise thanks. I...

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 My Wife's Sissy Slut

by SissyFaye on Jun 8, 2020
Transgender & Crossdressers

All alone, the kids are gone! My wife and I are cuddling naked in the bed. I'm all locked and stiff in my cage. She rolls over and kisses me deeply and forcefully good morning. She pulls away, both of us breathing heavily from the passionate kiss. She says "Good morning, my sissy, I see that made you strain in your cage. Do you wish to be released?" I...