Dear Auntie Helga,
I ended up going to my sister's house for dinner tonight but this time it didn't seem so normal to me. When I got there Anne could see I was a bundle of nerves. She took my hand calmly letting me know it was going to be alright and I would feel better once dressed. We went to the spare bedroom where Anne had everything all laid on the bed.
I took my clothes off and Anne went to work fitting the chastity device to my penis. She talked to me through the process letting me know in no time the device wouldn't be any big deal. Anne picked up some pink panties and slipped a pair on me followed by a new bra. She told me she picked up a few things Jen wanted me to wear.
Anne held up a girdle with garters all over it then proceeded to help me put it on. She showed me the proper way to put on stockings and attach them to the girdle. Then came a pair of rubber boobs to go in my bra adding a lot of weight. Anne continued until I was standing there dressed in pink once again.
Anne sat me down while letting me know what was next. I just listened knowing it didn't matter what I said with Jen on her way shortly. Anne put some false eye lashes on me followed by several coats of mascara. She showed me how to apply lipstick then moved on to painting my nails. I felt so humiliated and nervous but Anne was quick to let me know soon I would be doing this by myself every day. At one point I asked Anne if I could move in with her for a while instead of being a sissymaid for Jen. She told me that wasn't a good idea and I should look at my life with Jen as an opportunity to show my love for her that much more.
Anne and I had dinner with me helping cook and cleanup just like last time. I kept looking at the clock while we drank a coffee until I heard the doorbell. It was then the butterflies in my stomach went crazy. Anne took my hand so we both went to meet Jen.
The door opened with Jen seeing me standing there all dressed in pink. She smiled letting me know I looked very pretty and she was pleased how nice the dress looked on me. I on the other hand was bright red sinking into the floor. Jen came in and checked me out while talking with Anne. Jen told me to lift me dress up so she could see my chastity device. I felt so embarrassed to have my penis in chastity in front of my new Mistress. Jen told me to fix my dress and to thank Anne for helping me which I did with a hug. Jen asked me how I liked my new dress and heels. Anne warned me ahead of time to let Jen know I loved my dress and all the trimmings and was thankful for the opportunity. When Jen asked me I said the same thing.
Jen talked to me with Anne there to let me know I was her sissymaid now and both her and Anne were to be called Mistress from then on. Jen also told me Anne was going to help me become a sissymaid when she wasn't available due to work. I thought to myself oh good to have Anne to help me.
We stayed for about an hour then headed home with me riding in the car dressed in pink. When we got home Jen sent me to clean out my drawers and closet to make room for more feminine things she had in the car. I did what she told me remembering what Anne advised. Jen told me all my clothes were going to be at Anne's place until she decided what to do with them down the road.
Jen talked with me about her dream to have me as her sissymaid and how it all started as well as Anne being involved. Jen wanted me to know Anne didn't want to help at first but later agreed to help me. Jen told me I was very lucky to have a sister who is also my Mistress. Next Jen showed me my new nighties and sent me to change into one while she had a bath.
Jen came out later to find me wearing a pink nightie with pink being my new color by the looks of it. Jen went over some guidlines and jobs she expected me to do beginning tomorrow morning. Jen told me there was going to be a spare chastity key kept in the house in case of an emergency but she hadn't decided where it was going to be just yet.
Anne warned me to never talk about the chastity device with Jen. She advised I get used to wearing it since it wasn't likely to be coming off anytime soon. I remember tearing up hearing my penis was going to be in chastity. Anne was good to let me know as a sissymaid it was necessary and I would be fine.
This is all I have time for with Jen calling me to go to bed. Auntie Helga I'm scared and nervous not to mention embarrassed.
Thank you for your letter Casey. What wonderful news and congratulations on becoming a sissymaid, a noble calling and a great opportunity to serve the two women you love most. Now the adventure begins.
Your Mistress Anne is a real treasure and I'm sure is looking forward to being your Mistress with all that implies, she may well have in mind various personal services you would not have performed for her in the past but most certainly will be before too long. Tasks like giving her baths or dressing her to even providing her with oral sex. Of course your primary Mistress is your beautiful wife and love of your life, Mistress Jen and I'm sure she has been looking forward to you becoming her sissymaid for a long time.
I understand your fear, that's normal for a new sissy but it will pass soon as you begin to change into the feminine and submissive sissy you are destined to become. I suggest you start to think of this as an opportunity to devote yourself to your Mistress's pleasure and comfort, a way for you to express your love, to lose yourself in the new role.