Dear Auntie Helga,
Today I went with my mom to buy a chastity device against my will but I still went. The person at the shop talked to me and my mom about chastity devices. She felt since I'm in my late teens the HolyTrainer was the best starter device with it being made of a flexible material. Her and my mom talked about the HolyTrainer letting my penis some freedom but it would not allow me to touch my penis anymore. My mom bought me the pink one with a big smile on her face.
At home my mom pulled my panties down then put the HolyTrainer rings on until she found the right one. It felt so strange having my mom handling my penis and the HolyTrainer slide on my penis until it was locked in place. My mom asked me how it felt and I said okay I guess with her telling me it looked very pretty. My mom talked with me while I put on one of my uniforms telling me how much she liked me as her maid and soon to be sissymaid. I noticed my mom's tone changing to more of a Mistress sound but still nice to me. My mom told me how proud she was of me to be her maid and she was looking forward to me learning more about how to make her happy.
I asked my mom how long I had to wear the HolyTrainer and she told me until she decided I was ready for a stainless steel chastity device. When I teared up my mom held my hand letting me know it was going to be alright and I was going to make her a good sissymaid. Mom sent me to get started on my chores while having something attached to my penis which felt weird. I know my mom means well like she is helping me but part of me is terrified with the changes in her mind.
Auntie Helga if you have some advice for me please share it if you can.
Mark (also Mary)
Thank you for your letter Mary. What a wonderful turn of events, a chastity device is an important step in becoming a proper sissymaid, it serves to remind you that you no longer control that little penis of yours but it, like the rest of you. This is a large change for her as well but now that you have given her your permission as it were, to become her sissymaid, she is taking the opportunity to explore her options and become someone else, someone more powerful and dominant. My advice is that you relax, don't worry too much about the changes either in yourself or in her, let it be for now and things will settle into a wonderful new relationship.