Dear Auntie Helga,
Thank you for maintaining this wonderful website. It is one of the sites I am a lucky enough to have on my allowed reading list, when I have internet time. My Mistress likes to keep a tight rein on all my reading habits - and everything else. I am lucky to have someone who cares that much about me.
My Mistress has instructed me to write to you, to tell you how my life as a sissy begun. Although, it is more accurate to say this is how it was awoken in me. I know deep down that I have always been sissy.
I had my first job at 17, I needed somewhere to live and I was put in touch by Beatrice - my work colleague - with her auntie, who was looking for a lodger. I had a huge crush on Bea, she was my superior, in her 30's and had taken me under her wing, as I was extremely shy.
My two Dommes - as I was now aware - had been lovers for some time. Although Mistress Bea refers to Aunt Estella as "Auntie", She is in fact Her aunt by-law and has lived with her since She left school. After a short time, She had become Auntie's submissive live-in-maid. Mistress Bea was still Auntie's submissive, but very much my Domme and as such I was now to address her as Miss Bea, or Miss Beatrice on more formal occasions.
I moved in the same day as the viewing, as everything: the house and my room were perfect and Mrs Von Hayden - Bea's Aunt, seemed lovely. She was a very glamorous widow in her mid/late 50's. Tall, still attractive and very well dressed.
One Friday night, about 2 or 3 weeks after I had moved in, Mrs Von Hayden came into my room and sat down next to me on the bed. She asked if everything was okay, was I happy and comfortable in her house? I replied, saying I was very happy. She then bought up a delicate matter. She had noticed that 1 or 2 items of her underwear had gone missing from the wash basket and had anything accidentally made its way in with my laundry? I felt my cheeks begin to burn with embarrassment; I had found a pair of panties, but what was worse, I was actually wearing them. I looked at her sheepishly and confessed to her immediately. I was crestfallen, I had not taken them deliberately, but when I saw them in with my clothes, I could not resist trying them on.
I felt like I was going to burst into tears, as I told her the whole story. She looked at me sympathetically, but I could tell that she did not believe that I had not taken the deliberately. To be honest, the story did not sound convincing, even to me!
I told her how sorry I was, that I loved living here and that I would do anything to make it up to her. She asked, how I liked wearing her knickers? I could not look her in the face, but I told her how I loved the feel of them and that they made me feel sexy. She asked me to stand up and show her how I looked in just her panties. I felt like I wanted the world to swallow me up, there and then. But I knew she had the right to ask and I really wanted to stay in her house.
I stood up and took off my jeans and tee shirt slowly and shyly. I stood there naked apart from a pair of skimpy black knickers. I did not know where to look. And to make things worse, I was starting to get an erection. She smiled and told me she was willing to forgive me this once, but she would have to punish me, and then I had to tell her honestly how I felt about dressing up like a girl.
I nodded in agreement; I was just relieved I did not have to leave her or the house. She asked me to take out all of my clothes from the wardrobe and put them in a pile. As strange a request as this seemed, I did so without question. I did not have many items and she was able to remove all my clothes in one big duffel bag.
When she returned, she had another bag with her, that she put on the floor. She started removing some girl's clothes from the bag and carefully put them out on the bed. She laid out two separate outfits for me. The first was a baby pink satin dress with white frills: like a young girl would wear. She lifted the dress up and gestured for me to put it on; that to my surprise I did without hesitation. She put the other black outfit on a clothes hanger and left it hanging on the wardrobe door. She instructed me to lie on the bed. She removed the black knickers, my erection was full now, but my penis is quite small. Mrs Von Harden gently rubbed my tiny bulge and to my shame I came within 10 seconds.
"Oh, dear!" she said as she cleaned up the mess with the panties, "We will have to do something about that." She placed the panties in my mouth and proceeded to lock my now tiny flaccid cock up in a pink plastic chastity device. She placed the key on a chain, that hung around her neck. She continued to dress me in a pair of big frilly, pink knickers and white hold up stockings. She finished my ensemble with a pair of mittens to match my knickers, that she tied up so I could not get them off.
"This is insurance so you cannot play with yourself tonight." She told me in a very motherly voice. "Now, don't we look like a little princess?"
"For the rest of the weekend you will be my Isabella. Is that okay?" I nodded, but I knew the question was rhetorical. "You can call me Auntie, or Aunt Estella."
Aunt Estella tucked me into bed and kissed me on the forehead. "Night, night Isabella."
She switched my light off and closed the door.
"Night, night Auntie."
I was excited when I tried on Auntie's panties earlier, but not in my wildest dreams did I think anything like this could happen and that I would be so happy about it!
To my horror, I was awoken early the next morning by Beatrice, she was wearing a black silk dressing gown (night robe) and matching pyjama bottoms.
"Sissy Isabella, we knew you wouldn't be able to resist the panties we left out for you." She said to me in a slightly patronising, mumsey voice, "For this weekend, you will address me as Mistress Bea or Ma'am."
She looked at me expectantly, until I uttered, "Yes, Mistress."
"Good, now let's get you out of those mittens and to work."
I was instructed to put on the black dress hanging on the wardrobe, it soon became apparent that it was part of a French maid's outfit. Mistress Bea attached a white apron, with matching gloves and cap. She decided that the stockings from my "princess" outfit matched perfectly. Mistress Bea examined my chastity cage, that my tiny little cock was bursting to escape from. Finally, black stilettoes, they fit perfectly and I realised they had been planning this a while.
"Auntie told me about your naughty sissy clit last night. No more of that for a while, my girl."
I was ordered down to the kitchen, to prepare tea for two in bed for Aunt Estella. When I entered the bedroom, I found Mistress Bea and Auntie sitting up in bed waiting for me. I poured them tea from a pot. I knew how Auntie liked it, Earl Grey with a slice of lemon. For the rest of that morning I was their sissy maid: I drew them a bath; I cleaned the house; I prepared lunch and I did all the laundry. Mistress Bea even gave me a spanking when she was not happy with the bathroom and I had to clean it again. Six smacks on my bare bottom that I had to count out and then thank her for. I had no idea that a punishment could bring so much perverse pleasure - to both of us!
In the afternoon, it was my turn for a bath, Mistress Bea shaved me from head-to-toe, she even removed my cage so she could get my pubic area nice and smooth. My sissy clit sprung to life while out and we had to wait a while before the cage could be reattached. I knew I would be punished for this later, but there was nothing I could do to help myself.
For the rest of the day, I was dressed back up in the "princess" outfit and had to crawl around on all fours, I was given blocks to play with and colouring books. Auntie took a more active role in the baby scenarios, she played with me, read to me, nursed me and spanked me when she thought I was being naughty. That night, I was made to sleep in a small bed at the bottom of Auntie's bed. I could hear Mistress Bea and Auntie making love all night, while I lay there in frustration.
The Sunday followed a similar pattern, I cooked lunch for them in my Maid's uniform. After lunch, I was Auntie's baby again, this time I had to give her oral service before I was sent to my room. Auntie tucked me into bed and told me I had a choice, if I wanted to stay in the house I would be her sissy: following Auntie's instructions at home and Mistress Bea controlling everything I did at work.
Well, the choice was easy. I am still living in Auntie's house many years later and have never regretted my decision.
Sissy Isabella x
How delightful to hear from you Sissy Isabella and thank you for writing and please do pass along my gratitude to your glorious Mistress for instructing you to so. What a wonderful way to become the sissy you were meant to be, even though it may well have been planned from leaving the panties laying about to having the clothes ready for you, this was an opportunity you took advantage of to everybody's satisfaction including your own.