First of all I want to take the time to thank you for allowing me to enter your contest. I literally have zero writing skills but I still felt the need to try. My name is James but I prefer to be called sissy maid Jamie. For as long as I can remember I have felt the need to be a sissy.
I can remember being 12 or 13 and constantly trying on my older sisters panties. It wasn't really a sexual thing at first. They just made me feel right inside, like girls panties were what I was meant to wear. After a few times of just wearing panties I started wearing pantyhose over the panties. The added excitement of wearing pantyhose sent me over the edge. I knew this wasn't normal but I didn't care.
The most embarrassing moment came when my Mother came home while I was trying to wash my sister's panties and pantyhose. She immediately new that I had done something wrong since I had never, ever done laundry in my life. I had decided earlier that day that I wanted to know what it felt like to pee myself while wearing my sister's panties and pantyhose. I remember pretending that a dominant girl made. me drink lots and lots of liquids and denied me bathroom privileges.
I remember telling my Mother that the cat peed on my sister's clothes and that I had decided to wash them before she got home. Without missing a beat, she picked up my sister's panties, held them up to her nose and breathed in deeply. She immediately looked at me and said, this is not cat piss. It didn't take long for her to realize what I had done. She looked me in the eyes and asked how I managed to piss all over my sister's panties and pantyhose.
I honestly can not remember how I explained to my Mother what I had done. I will never forget that feeling of being caught though and for some strange reason I remember wanting that feeling again. I can remember wearing panties under my Jean's and peeing just a little bit so the dark wet spot would show on my jeans and my friend Paul would see it. I can still to this day remember him jokingly saying that I pee my pants because I like the way it feels. The humiliation of my best friend teasing me was truly a sexual rush and I knew I needed more.
As I grew up my love for feminine clothing especially lingerie just grew with me. I would try on my first girlfriend's panties when she was in the shower. That mesmerizing feeling of her panties against my skin was simply a feeling I knew I would never, ever grow out of. My next girlfriend Laura who later became Wife and Mistress would tie me up and tease me with her panties. She was doing Femdom handjobs before it was popular.
When my Wife, Miss Laura first suggested that I wear her panties I almost cried tears of joy. I have since become her sissy maid. She has taken me to see two Dominatrices and participated both times. Mistress Rachel Fine was the first Dominatrix I ever saw in person. It was the first time someone other than Miss Laura saw me in my sissy maids dress. It was truly the most humiliated and excited I have ever been in my life.
Serving two incredibly sexy Women wearing strapons was so perfect. I knew at that moment my only purpose was to wear frilly sissy dresses and to serve and amuse Miss Laura. I also knew that I would without question serve anyone that Miss Laura told me to serve. To me the highlight of my visit with Mistress Rachel was after I had changed back into my male clothing. Miss Laura and Mistress Rachel were talking. I approached with my head bowed and stood in silence. Miss Laura excused herself from the conversation and ordered me to go stand in the corner until her and Mistress Rachel were done speaking.
I was born to be a sissified male. I love my frilly panties and sissy dresses.They allow me to be subservient to others. Last night for instance Miss Laura told me she was tired and she wanted me to prepare her bed. I waited for approximately 10 minutes for her to come into her bedroom. I was wearing my pink babydoll and pink frilly panties. She told me I had 5 minutes to pleasure her and then she needed to sleep. After I pleasured her orally, she told me to go. I immediately and uncontrollably began to beg her over and over for the pleasure of massaging her beautiful feet. I was nearly sobbing the look in her eyes forced me to keep begging until she said yes. I massaged her feet for at least 10 minutes after she fell asleep.
My only dream that has not yet happened is for Miss Laura to date a real man. A man that will give her the sexual relationship that she truly deserves. I am kept in chastity 24/7 and though I have given Miss Laura countless orgasms orally, I know she wants and deserves more. As a sissy it terrifies me that Miss Laura will find a real man and fall in love with him. That she will no longer want or need my services. It frightens me but if that were to happen, I would deep inside feel happy for her and her happiness is all that matters.
sissy maid jamie