Dear Auntie Helga,
I took to heart what you said to me in your reply. You are right it only mom and me here and there is no harm at all. We spent the day working together until she had a surprise for me before dinner. I sat on a chair in the kitchen and my mom covered my eyes so I didn't peak. She wiped my ears with something cold then wow she pierced one then the other. When she took off the blindfold I had studs in my ears. I never had earrings before so my mom wanted me to have them so she could share hers with me.
During dinner I thought of your email and answers to my questions. Rather than wait and see I asked my mom if she was going to make me her sissymaid. It caught her off guard and me for asking however I just wanted to know. My mom asked me if it was okay if she did or was I dead against it. I thought for a minute then went back to your emails Auntie Helga. My mom not waiting for my answer put her hand on my shoulder and let me know it would mean so much to her if I would say yes mom. I let her know I had no experience and it was hard to agree not knowing all about it. My mom left the room that left me to think I let her down. Within a few minutes she returned with a small bag that she set on the counter. by then I figured I better say yes and not let her down. I let my mom know okay I would let her do it.
My mom gave me a big hug and kiss before she retrieved the bag. She put the blindfold back on while letting me know she had another surprise for me. I stood there for a few minutes then I felt her pull my panties down to around my knees.I said out loud mom what are you doing? My mom told me it was a surprise and just be patient. I felt her handle my penis and testicles then do it all over again. Then I felt something ice cold go into my penis and around my penis at the same time. I knew then my mom was putting some kind of chastity device on my penis. Some how my mom knew I would agree to be her sissymaid. When she was finished I left my panties pulled up again and my dress adjusted.
My mom gave me another hug to thank me for allowing her to do it. She talked to me while I got used to this thing stuck in my pee hole and on my penis. My mom told me she wanted to sissify me years ago however it wasn't the right time with me at school. I asked why did she want to do it so much. My mom told me feminizing men is something she always wanted to do as many mothers have as well. I asked my mom why didn't she turn me into a girl when I was young. She told me is was frowned upon years ago and before the internet it was hard to find the right doctors. I asked and now my mom told me much easier to feminize boys and men. My mom told me female hormones were easy to buy with doctor's approval.
I asked my mom if she wanted me to take female hormones and grow boobs as her sissymaid. she was hesitant to answer me for a minute. My mom asked me if I would consider it which is when I knew she wants to feminize me. So I repeated mom you want me to become a feminine sissymaid with boobs like yours. Auntie Helga my mom has very large breasts and the picture of me with that size of boobs was freaking me out. I asked my mom did she really want me to take female hormones and grow boobs like hers? Her smile said it all, she was very serious.
I already committed to be her sissymaid and was in chastity. I said mom are you sure you want me to be feminine? My mom asked it was selfish of her but I knew she wanted this for a long time and this didn't just happen today. I was puzzled so I asked my mom to tell me what she wanted once more. She told me she wanted me to be her feminized sissymaid, have a small castration surgery to allow the female hormones to work better and faster. I repeated to my mom you want to take my balls? She said yes in order to help the feminization process as others have done. I shook my head then asked who pays for surgery, hormones and big bras.
My mom showed me a bank account she called the girl account. She put money away years ago so when I was ready to be a girl, women or sissymaid the money was there. I asked my mom if I could see one of her boobs out of the bra. She said sure as she took her top off and then her bra. I said to my mom OMG they are beautiful. She took my hand to feel them which is when I said okay mom you win. I will take female hormones as long as they are safe for me to take. I helped my mom put on her top as she didn't want her bra on again. I couldn't help think my mom wanted me to become her feminized sissymaid and for me to have boobs like hers too.
My mom told me she was going to teach me all about becoming a very feminine sissymaid. I just said I looked forward to serving her as I bowed to my mom. I don't know why I agreed Auntie Helga but what is done is done. Now it's time to pick out a nightie for the night.
Bye for now
Thank you for your letter Sean. Many mothers love to dress their sons, at any age and I hope you will come to enjoy sharing this with your loving and amazing mother. This is not more than you can handle, this is an opportunity to show your incredible mother just how much you love and worship her, really, what's the harm, its just the two of you and this is something she really seems to enjoy, I'm sure you will as well.