I looked at Steph, my face red with a combination of fear, anger and embarrassment. I was absolutely not going to stay in my sissy maid role when her mother came to visit.
I stomped my black heels on the floor and crossed my arms defiantly. I had to draw a line somewhere. The neighbors all obviously knew what I had become, and even that was far more publicity than I was comfortable with.
Steph just quietly started counting “one… two…”.
My resolve melted, knowing that reaching ten meant an extra month in chastity without relief. It was her trump card, and she knew it.
Don had given my little clit freedom for a glorious ninety seconds before leaving to go home. I had knelt on the floor and wanked, not even caring that they were sitting on the couch and laughing at me.
Every day since then I had done everything in my power to earn another release before the prescribed three months. Having two extra months added was horrifying.
So before Steph even got to six, I was kneeling on the floor in front of her, kissing her toes and begging her to not add any time to my chastity sentence. She said “Good girl” and told me to go get my ballgag.
I did the rest of my chores that day with my lips wrapped around the plastic of my gag, relieved that my punishment wasn’t worse.
Three days later I found myself shivering nervously as I walked to answer the door. Even though I knew Steph had told her mother all about our new arrangement, I couldn’t help but feel an enormous amount of shame as I pulled open the front door.
After months of wearing my maid outfits at the house, I had gotten very accustomed to the feeling of stockings and skirts. But standing in front of my mother in law in my silly little outfit brought fresh waves of humiliation that struck me surprisingly deep. It wasn’t a good feeling. As I timidly courtsied, I felt a girlish angst sink in.
For her part, Steph’s mother was very kind. There was no laughing or undue disparaging. It was almost as if it seemed really natural to her that I would be a submissive feminine maid. I served her and Steph drinks and did my housework as usual, letting the girlish feelings soak in. I could almost feel my testosterone evaporating as I scurried about the house, my heels daintily clacking on the wood floor.
Somewhere in the process I found my sissy space, and started almost enjoying my role. When I slipped up and accidentally dripped a tiny bit of hot tea on Steph’s mom as I poured, I felt genuinely disappointed in myself.
And even though I had been trained to request discipline after making mistakes it felt so natural this time.
After rushing to clean her up and offer effuse apologies, I stood back with arms held politely in front of my skirt.
"Please Miss, would you be so gracious as to offer discipline for this clumsy maid?"
I didn’t even blush much as I asked. It just seemed like the right thing to do. She looked up from the chair and smiled as she nodded softly.
I rushed to the bedroom closet to fetch the cane. I didn’t want her to be inconvenienced, so when I came back I carefully positioned myself off to her side so she wouldn’t have to move.
I almost felt a little sense of pride in my training as I pulled down my white lace panties and bent over.
"How many do you want, sweety?" She asked, and I politely asked for a dozen.
I let out little girlish yelps with each stroke, letting her know she was doing a good job. I focused on the mental image of the tea pot, wanting my discipline to teach me to serve better. By the last stroke I was genuinely distressed, jumping and quivering each time the horrible cane swished through the air and left a hot stinging line on my naked cheeks.
Pulling my panties back up, I thanked her genuinely. And as I went back to work, I embraced the shame, the humiliation, and the sting on my sissy ass. I felt so weak, so exposed, and I wondered if I would ever feel any other way.
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