Advanced Sissy Training: Part 6

This is a continuation of the story of  Becoming a Sissy Maid.

As my day progressed as Zoe I felt great. The house was shining and I was proud of the days work. Not to mention I looked and felt sexy. The only thing that was left was going outside to clean the windows which I was putting off as long as I could.

“Ok, Zoe. It’s getting late and you need to head home soon. Is everything done?” My wife asked as she entered the living room where I was dusting.

Do I admit that I have to clean outside still or lie and hope she doesn’t remember. Maybe I could clean the windows tomorrow in my normal clothes and she won’t notice.

“Yes, mistress. I’m all done,” I lied in my girly Zoe voice.

“So you went outside and cleaned all the windows like I told you?” She asked.

I felt dread consume my body. I was stupid to think she wouldn’t remember and now she had caught me. “Oh, no! Sorry mistress, I must have forgotten!” I built another layer on top of my lie.

“You forgot?! That was a specific request, Zoe. This is simply unacceptable. Go to the bedroom and assume the position, NOW!” She screamed at me, pointing up the stairs towards the bedroom.

I ran upstairs as quickly as I could in my high heels and in the bedroom I arms and face on the bed, sticking my butt out for her to punish me.

“This is bad, Zoe. You lied to me and failed me as a maid today.” Her words were oozing with disappointment as she entered the bedroom.

“I’m sorry, mistress. Please let me make it up to you. I’ll do anything!” I begged her. She had already threatened to stop having Zoe work for her and I was desperate to not lose that.

“You have a lot to prove to me as a maid, Zoe, and trust me, you will make up for your failure today. You clearly love being my sissy maid and while you may be lacking as a maid today, I think it’s time to escalate my plans and train you to be a better sissy for me. Stay there while I get ready.”

A better sissy? What does that mean? I thought the whole point of this was for me to clean for her. I waited patiently as I heard her riffling through her closet and putting something on. She walked up behind me and lifted up my dress as she normally does to spank me. This time however, I felt something poke me in the butt.

“Remember that you agreed to allow me to use new toys? Sit up and look at the first one.”

I pushed myself up and turned around to sit facing her. She was wearing a large strap-on that must have been at least 8-inches long. I was shocked. What was she going to do with this?

“The first thing I need my sissy to know is how to suck cock. So start sucking, slut.” She wiggled the dildo in my face then with one hand wrapped around it she poked my mouth with it. I knew better than to question her motives so I opened my mouth and slowly put it on the dildo.

“I said suck it, slut!” She thrust the dildo deep into my mouth causing me to gag as it poked the back of my throat. I reached up to grab it by the shaft and pull it out. I could feel the thick veins of the dildo slide along my tongue as I pulled it out. I slowly started to move my head back and forth along the dildo.

“Ugh, Zoe. This is pathetic.” She grabbed the back of my head and forced it deep in my throat again, this time holding it for several seconds. “I’m already sick of watching this. We’ll circle back to your cock sucking ability. Bend back over for me,” said demanded as she pulled the dildo out of my mouth.

I caught my breath as I turned around and put my arms and face back into the bedding, butt up in the air. She went back to the closet to grab something else and I heard a squirt. She walked back to me, rubbed my butthole and said, “Ok slut, now let’s work on stretching out your pussy…”

My pussy?! What does she mean by that? I tried to turn around to look but she put her hand on my back and thrust and I quickly figured out what she meant as something big and cold penetrated my butt.

“Oh… oh my god! What are you doing?” I yelled out at her.

“What do you think I’m doing? I’m fucking my naughty little sissy in her tight little sissy pussy.” She slowly pulled the dildo back then pushed it back in. Back and forth, back and forth, over and over…

I wanted to protest more but couldn’t. I could feel myself relax which allowed for the dildo to dildo slide easier. It felt… good. I had been enjoying the vibrating butt plugs she had me wear on occasion, but this was different. This was dirty and the movement of the dildo felt amazing. I really was her dirty slut.

“That’s right take my cock, bitch. We’re going to loosen up your pussy and make you a real sissy.” She pushed in further, pressing the tip against my prostate.

“Ooooh my god!” I exclaimed as I moaned loudly. This was mind blowing. My penis was pressing hard against my chastity cage.

She grabbed my hair, pulled my head back and shoved her tongue deep my my throat as we began to make out. My penis continued to throb.

“Oh. My. God!” I couldn’t take it anymore. Suddenly, I felt my penis explode as I orgasmed. I let out a loud sigh as I collapsed into the bed.

“Did you just cum, Zoe?!”

“Uhh… Yes, mistress…” I sheepishly admitted.

I felt her pull the dildo out of my ass. “I knew you would like getting fucked, Zoe, but not this much. Well, looks like you’re going to make for a good sissy after all. Now clean up your mess and then clean those windows like I told you before.”

I laid on the bed in a puddle of my own cum, trying to catch my breath. What just happened? I certainly never thought she would take things this far… or that I would like this much. What I did know was that I didn’t want it to stop.

Becoming a Sissy Maid Story Guide

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