Sissy Punishment Stories

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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...

Sissy Gets Punished

by MsMorrigan on Sep 16, 2017
BDSM

Once upon a time there was an overly eager sissy girl. This sissy girl loved her mistress. She loved her so much she tried to anticipate her every whim before she needed to even speak the words. One day the sissy girl was vacuuming, dusting and general cleaning. She was openly lamenting on how her overly large pathetic sissy clit was getting in her way. How...

Sissy's Shopping Trip Pt. 01

by SissyFaye on Jul 13, 2020
Transgender & Crossdressers

"You finally got paid, Sissy!" my mistress says with excitement. "Yes, I did, my love," I say. "Well, I think in celebration of your first paycheck from this new job, we need to go shopping!" she says. "Oh really, shopping for what? I ask. "Clothes for me, and maybe some for you," she says. "Mmm, sounds like fun!" I say with excitement getting hard...

Becoming a Sissy Maid & Slut Vol. 08

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Fourteen: Chantel Learns a Lesson. Another bright and early morning for me. Another busy day ahead as a sissy maid and later on as a slut. What plans Master has for me as a sissy slut tonight, I don't know, but I'm sure it will be exciting, with lots of creamy cum for me to taste and swallow as well as good for hard core butt fucking. I'm already ge...

My Mistress is My Wife Ch. 02

by slavetohiswife on Sep 14, 2017
Fetish

I'd spent what seemed like forever locked away in my cock cage, looking at and downloading porn for Mistress while she slept. I felt like the slightest touch to my cock would cause me to explode. I had tried and tried to touch myself the whole time but the cage more than served it and Mistresses purposes. I was only able to get so hard and my balls ached. I...

Nancy and Her Boss Ch. 03

by MidniteSpanker on Sep 19, 2017
BDSM

Part 3 – The Weekend. The initial stories in this series Nancy Remembers Chap. 1 Nancy Remembers Chap. 2 Nancy Remembers Chap. 3 Other stories continuing in this series Nancy and her Boss Part 1 Nancy and her Boss Part 2 Nancy and her Boss Part 3 - The Weekend Nancy and her Boss Part 4 - More Weekend Then the following are separate but related stories...

The Session

by davemacc65 on Sep 16, 2017
Transsexuals & Crossdressers

I arrive at the door of the hotel room, at the stated time. My feelings were mixed. Nervous, meeting you for the first time and excitement knowing that I would be in control of the situation, well at least for the moment. Just before the door opens I realise I will not recognise you! The only pictures I have seen of you, you are wearing a hood! The door open...

Training of Mistress' New Sub Day 01

by naughtyboy082 on Sep 19, 2017
BDSM

As Mistress Sharon has requested, a written story... THE FIRST MEETING MISTRESS SHARON sends out a late night text that her new submissive has been waiting for anxiously all week long as he sought to prove his obedience and worthiness. "Congratulations, sub! You have successfully completed your probationary period...official training begins in the morning...

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

A Tale of Slavery

by gunnarsub on Sep 17, 2017
BDSM

Once upon a time there was a straight guy who was known by everybody as a well respected fellow. But he had a secret life. Nobody knew that he dreamt to become a feminized slaveslut, seeking an infinite and irrevocable blackmail relationship with a pitiless Mistress who would be prepared to break him with no way out. He wanted the Mistress to torment him n...