Sissy Maid Training Stories

Sissy Maid Training Stories
This is a continuation of the story of Becoming a Sissy Maid .
I couldn’t believe it, but I was starting to look forward to being Zoe, my maid alter ego. I found myself naturally keeping the house tidy throughout the week even in my normal male state. Cleaning was becoming second nature even though part of me thought that if I left the house messy enough my wife might demand an extra visit from Zoe.
Perhaps it was because my wife had been keeping me locked in my chastity cage for longer and longer and I had a lot of pent up sexual energy. I felt like I was able to release some of this energy into my dressing up as Zoe, even though it did feel like a long teasing session, especially when my wife rewarded Zoe by making out and caressing her body. My wife had also started demanding that I wear panties every day to be more in touch with Zoe so feeling my thongs holding down my caged penis and tickling my butthole made me constantly think about dressing up as a maid.
One day I finally built up the courage to talk to my wife and suggest that Zoe spends an extra day each week cleaning. I gave examples of all the chores that she could perform in that time such as mopping the house, reorganizing the pantries, cleaning all the house windows, etc and promised more Zoe would make her happy.
“Just can’t get enough of being my sissy maid, can you? Wow, Brad. I knew you would like it, but not this much,” she replied to my suggestion. “Alright, Zoe can come more often but only if you agree to a few caveats.”
I blushed a little at her calling out my enjoyment of being Zoe. “Alright, name it,” I tried to say as nonchalantly as I could.
“First, I want to hear you admit it. Say this, ‘I love being your sissy maid and doing everything my Mistress says’.”
Pretty easy first demand. I repeated her line as a smirk grew on her face.
“Good. Next, you have to agree to me expanding the toys I use with Zoe. If Zoe is going to be cleaning more often, then I’m going to hold her to a higher standard and may need new options to motivate her for her new role.” She crossed her arms and lifted an eyebrow as she listed her first requirement. Clearly she has been thinking about this herself.
“Ok, sure.” I wasn’t sure what toys she meant but it couldn’t be too bad – maybe a bigger butt plug or spanking with a bigger paddle? “What else?” I asked.
“Lastly, I like that you mentioned cleaning all the windows because they definitely need to be cleaned. However, once you get started I think you’ll notice that most of the dirt is on the outside of the windows. Zoe will be expected to clean the outside as well.”
My heart skip a beat. Outside? She wants me to clean outside?
She could tell I was panicking. “Or maybe you’re just not cut out for this whole maid thing and we should just stop. If you can’t clean some simple windows then you’re not of much use to me.”
Here I was asking to be her maid more often and she was suddenly threatening to take it away. I had no choice. She knows she has all the power and she’s choosing to humiliate me with it.
“Ok, fine. You know Zoe is a good girl and will do anything you say so of course she will clean the windows inside… and out.” I didn’t feel good about agreeing, but I couldn’t lose being Zoe.
“Exactly what I wanted to hear. Now I expect to see Zoe here in 15 minutes.” She shooed me away with her hands and I excitedly ran off to become Zoe. “And remember,” she shouted after me. “This was your idea, my little sissy.”
The way she said that unnerved me, but I didn’t care. I would get to be Zoe more often.
Becoming a Sissy Maid: Unlocking Hidden Desires is now available on Kindle and Paperback. Read the full story of Brad, Zoe and Melissa in this 13 chapter, 136 page book.
Hello Madame,
Yes I am a sissy crossdresser with a ardent love and desire to dress up in ultra pink nylon lingerie.
My dream came true in New York many years ago were i finally found a smal lingerie shop that were
friendly and helpfull in permitting me to purchase all my dreams directly in the store. Yes it was difficult
to find a place were i would feel free to purchase all my dream garments. It was very difficult to find a
place that was open minded and helpful to a sissy like me. At first I was very nervous and up tight
but desire to own pretty panties,bras, garter belts,corsets and night gowns was so strong that I overcame
my shyness. Hope this is not boring you, would love to continue in detail my true story. Shall i continue????
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Are you ready to go “ Down The Sissification Rabbit Hole?” Then read this…
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B eing a sissy takes a ton of work. It can seem like a never-ending process… and it pretty much is. However, there is a light at the end of the sissification tunnel—and in Part 3 of this sissy training guide, you’ll get a clearer look at that light…

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Are you ready to go “ Down The Sissification Rabbit Hole? ” Then you’ll want to read this…
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Shortly after I started my chastity life and relationship with my wife, she implemented what she called my “ chastity chores list “. These were daily and weekly chores that I was required to complete in order to have a chance of getting unlocked from my chastity cage. Little did I know that my wife would soon take this to a whole new level.
At first, my chastity chores started as simple daily tasks like making the bed and doing the dishes every day and vacuuming the house once a week. Occasionally she would have other one time requests like deep clean the kitchen or clean the bathroom which were easy enough to tackle and satisfying knowing that I was making her happy. If I forgot a chore or didn’t complete it to her liking I would get a spanking and an extra day in my cage. This wasn’t too bad and honestly these chores were all things I probably should have been doing anyway. This went on for some time and we were both happier for it.
This all changed one day when my wife called me into the bedroom. She was standing next to the bed when I came in and she said, “Hun, while I appreciate that you are usually so good with your chores, the house is still too messy. With the pandemic we haven’t been able to have our house cleaner clean the house in quite a while so it’s time for you to take on some new responsibilities… and a new role.”
That didn’t sound too bad. I assumed she meant doing some dusting here and there and more general cleaning. She beaconed me over to her and pointed to something on the bed. “I went ahead and bought you a uniform for your new role. I hope you like it.”
I was pretty confused about why I would need a uniform to clean more until what was on the bed. She had laid a maid’s outfit complete with dress, apron, and headband along with lacy lingerie with a garter belt, thong and thigh high stockings. I’ll admit that crossdressing is something that has peaked my interest before, but my wife was never into the idea.
She could tell I was confused. “That’s right, you’re going to be my maid. From now on it’s your job to make sure this house is spotless. You will dress up and act as my maid once a week and clean until I’m satisfied. Do a good job in a timely manner without complaining and you may get a reward. Anything else will earn you a punishment.”
I stared at my wife in disbelief. It kind of sounded fun, but also like a lot of work. “Are you serious?” I asked her.
“That’s not a complaint is it?” she retorted, putting her hands on her hips and a frown on her face.
“No, dear.” I said as I went back to scanning the outfit on the bed.
“Good. Now get dressed. And while you’re my maid, you will refer to me as ‘mistress’. Text me when you’re done.” She quickly walked out of the room and shut the door, leaving me and the frilly maid dress and lingerie.
I could feel my dick trying to get hard in its cage. Never before had my wife been so stern with my chastity; it was very sexy and I felt like she somehow took even more control over me in that moment. I was becoming her slave and I had no choice but to do as she instructed and get dressed so I got dressed.
When I was finished with my maid dress on, thigh highs clipped into the garter, and apron tied behind my back, I texted her to let her know and waited for her to come back. She opened the door with her hands behind her back.
“Well don’t you look cute. I’m glad you obeyed me. Here’s the last piece of your outfit,” she said as she revealed her right hand which was holding a black silky pouch. She walked up and handed it to me as she slowly walked around me, examining my outfit. She lifted my dress in the back and ran her finger along the top of my thong then gave my ass a little slap.
I opened the pouch and pulled out out a butt plug.
“As my sissy maid, I expect you to always be caged and plugged. You are to always have this butt plug in and vibrating. Now get your ass plugged and get to work. I’m going to go get a pedicure. I expect the house to be much cleaner by the time I get back.” She gave my ass another spank and left the room.
With no other choice, I put in the butt plug and got to work…
Becoming a Sissy Maid: Unlocking Hidden Desires is now available on Kindle and Paperback. Read the full story of Brad, Zoe and Melissa in this 13 chapter, 136 page book.
i feel so girly in my nylon panties,please punish me, i must be humiliated. make me sing and dance for you,please
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July 08, 2022

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