Sissy Holiday

by Tania Long

Chapter One: The Journey and Arrival

 

"When we arrive I expect you to change immediately into your Maids uniform, as this is a holiday for me - not for you. And by the way you'll be sleeping in the back bedroom, under lock and key," said Mistress.

I shivered with excitement and anticipation!

I packed up the car, including all my maids' clothes.

"Have you put on your chastity device?" My Mistress asked.

I rather sheepishly looked down and admitted I had not.

"Well go and get it and put it on, in front of me, if you don't mind!"

I adjusted the device standing naked in front of Mistress, put the lock in position and push it shut. Handing the key over, Mistress casually put it in the back pocket of her jeans.

"Well what are you standing about for; get the car packed and we can get off."

The journey, took four hours and I drove with a rising tension in my groin and a lack of movement due to the chastity device being firmly locked in place. A hand would stray across to my lap and add to the discomfort.

I was told that this week would be a very important one in my training to become a good sissy maid and Mistress expected very high standards - or else she would be displeased. And from previous occasions that were not something I wished to experience.

Upon arrival I unloaded the car, whilst Mistress seated herself in the lounge.

"Get me a coffee, before you do anything." I was instructed.

I handed her the cup and asked if there was anything else I could get her, I was just about to curtsey, but forgot I still had my male clothes on.

"No," she said. "You can change now into your uniform - the plain pink one, not the frilly French one, I'm saving that for later," my Mistress smiled to herself at this point.

"And put all the clothes away and then you can start preparing dinner."

I hurried off, feeling the excitement at retrieving my various maids' clothes. I carefully put them away in the back bedroom, as I knew that was where I would sleep and I quickly peeled off my jeans and tee shirt.

My maid's clothes consisted of padded bra, panty girdle, suspenders and stockings, which were usually natural in color, frilly panties, a net petticoat and a plain pink maids dress with a knee length skirt and full apron. I always wore sensible low-heeled shoes whilst doing housework and had a mop cap, which finished, off my outfit. I certainly looked like a sissy maid and would not pass as a woman, but the servile husband I had become. Before I had made much headway on dinner Mistress rang the bell. This was my call to attend for instructions. I smoothed my apron and hurried into the lounge.

"Very pretty" Mistress said.

"However, you forgot to curtsey as you entered the room!"

"You must practice curtsying - when you enter and leave the room. Also curtsey when you have been given an instruction. Do you understand?"

"Yes mistress," I replied, doing my best curtsey, stepping my left foot well behind the right and giving slight bow, keeping my head down and pulling up the hem of my skirts.

"That's better, as I will not tolerate any sloppiness in my maid."

"Now pull up your skirts and let me inspect you."

I did as I was told and lifted up my skirt and petticoat up to my waist.

Mistress frowned.

"I've told you before - no knickers, now take them off!"

I quickly removed my frilly knickers and panty-girdle.

"What I want to see is a bare backside, whenever I tell you to pull up your skirts. You may be a sissy maid," she told me, "but it's what I want that matters and you need to get that into your head, my girl."

I curtsied, letting my skirts back down and held my head low with hands together in front of me.

"One more thing, when you've finished your tasks I don't expect to have you coming back to me and asking for more things to do. I hate your whimpering."

"You are to go over, without me telling you and stand facing the corner with your hands on your head," she said, pointing to the corner of the room.

"Better still I don't want to see you standing around, so go and stand by the front door in the hall. I'll call you when I need you."

"So your either going to be working or standing in the hall. Understand?"

"Yes Mistress," I replied and quickly did a curtsey.

"Have you fixed the lock to the back bedroom?"

"Yes" I replied.

"Good then when I've finished with, you'll be kept in there out of harms way. And have you a potty, in the room?"

I nodded.

"Because when I've locked you in I don't want to be disturbed, by your need to pee in the middle of the night!"

I said nothing and hung my head lower.

She was really getting into this role and I felt a degree of unease as I thought about the freedom I had given up and the different path my life was now taking. It was, however, something I had yearned for and I now had to accept it and focus on my Mistresses needs rather than my own.

All household chores were my responsibility, I slept in the spare room more often than not, I was only allowed to come under strict instructions and most days I wore some female clothing and when undertaking my maid's duties the uniform was obligatory. Still I was content and the role reinforced my desire to serve and make my Mistress happy, which I had realized was an innate part of my being a transvestite and sissy maid.

I had served my wife as a Maid for the last few years and she had devised an assessment level to acknowledge my performance. Level one being the lowest, when I had undertaken minimum duties in the preceding week, through to level five when I would be judged as virtually a full time maid, serving both household and personal duties. I had only been given a level five once and currently I was judged at level four.

Dinner complete, I tidied everything away and then stood in the corner of the hall. After what seemed like an age, Mistress came out of the lounge to use the bathroom. I felt her standing behind me and she lifted up the hem of my dress and petticoat and tucked them into my suspender belt, leaving my backside completely exposed. I was left alone again as the lounge door shut with me facing the wall, hands on head.

My predicament came to end when the bell rang.

"Right I don't need you anymore Maid," my Mistress announced.

As an aside, I was called Maid when dressed as one; Mistress said she could not be bothered to come up with a femme name and that as I was just a Maid then that is what I would be called.

"You can go to your room and go to bed," I was told.

I curtsied. "Thank you Mistress" I said.

As I felt somewhat left out, I went onto ask what should wear to bed.

"Don't be silly," she said.

"I don't care what you wear, all I need to know is that you're no able to play with yourself and you're locked away. Now go on off you go." She said dismissively, waving her hand.

I dutifully retired to the back bedroom. Having been to the bathroom, I changed out of my uniform and hung it up, leaving all my under clothes in a neat pile. I put on my dark blue nightie, shut the door and went to bed.

The chastity device prohibited any sexual thoughts, because an erection was out of the question, so I lay there and wondered if Mistress would look in on me before she went to bed. But my hopes were not to be, as after an hour or so (I had no clock or watch in my room – it was not allowed), I heard the lock being turned and I was secured for the night. I soon fell asleep, dreaming of what tomorrow would bring.

Chapter Two: Shopping

I awoke early but could not tell the time. Shortly I heard the bathroom being used and the door was unlocked.

"Get yourself dressed and bring me coffee," was the instruction, through the part opened door.

I did as I was told. Hurrying so as not to keep my Mistress waiting, but also wishing to be presentable and look my best.

Upon entry to her bedroom I remembered to curtsey and was told to kneel at the end of the bed and await further instructions.

"Today, we are going shopping," Mistress announced.

I dreaded the sound of this, for I knew shopping would probably mean some form of embarrassment and humiliation for me. Previously I had been required to buy make up and lingerie. I sometimes managed to reduce my discomfort by pretending to purchase the items for my wife, although Mistress increasingly made the task harder by being very explicit in what I was to purchase. This once meant asking for a garter belt with six suspenders at numerous checks out counters and having failed to buy one, I was instructed to go back out again and try more shops and not return until I had purchased one. After several aborted enquires, with my reddening face, I eventually found a belt with six suspenders and thus returned home. So I had a strong feeling of unease, as Mistress went to have her shower and I was left clearing away the breakfast dishes.

"Maid" my Mistress called from the living room. "Right, I want to change out of all you maid's uniform and comeback in here, nude, carrying your jeans and tee shirt, off you go" she instructed.

I returned as instructed. Mistress handed me some underclothes and told me to put them in the living room, whilst she could watch. Gone were my male pants and socks and in their place I was given a black bra, panty girdle, suspender belt and tan stockings. Once I had dressed in the lingerie I was ordered to put my jeans and tee shirt on. Mistress allowed me to wear a pair of trainers, but I was very conscious that any slight hike in my jeans would expose my stockings.

I nervously followed her out of the house and into the main street.

I was only too aware that at any time she could cause me the utmost embarrassment as we walked down the high street. Before long we came across the first charity shop and Mistress led the way in and I followed a few steps behind. Whilst dressed in female lingerie I felt very exposed, although no one could readily see what I was wearing. Needless to say I was somewhat nervous that anyone, particularly an observant woman would see the line of my bra under the tee shirt or catch a glimpse of my stockings.

Mistress told me to stand close to her as she looked through racks of dresses and skirts. I knew what was coming next. It only took a few minutes before she called me over to her and held up a black dress to see how it looked on me. To maximse my discomfort she directed me over to a full-length mirror, which was by the check out and again held the dress against me. By this time the woman and young girl behind the counter were watching with interest and I noticed they had started to whisper to one another glancing in my direction. By now Mistress had gathered three dark dresses and was moving towards the checkout. I'd hoped that she was going to buy them, but no such luck.

"Can my husband try these on?" she asked.

The assistant quickly said yes, with a rye smile and pointed to the changing area.

"Off you go and try each one in turn", my Mistress instructed. I looked at her with a pleading face, as I could feel myself reddening by the second. The glare I received back, made it clear I had no choice, this was not my agenda and I had no say in what was happening.

I took the dresses and walked towards the changing area. Just as I had turned Mistress said. "And take these with you, as I wish to see what you look like wearing heels". She handed me my pair of black stilettos and I knew things could only get worse.

In the changing area I quickly pulled across the curtain and removing my outer clothes, unzipped the dress and stepped into it. I struggled with the zip, as I could feel my hands shaking and without fully being able to do it up I stepped into the shoes.

Next I heard my Mistress say. "Let's have a look at you then".

My heart sank. I slowly pulled the curtain back and Mistress beckoned me into the shop area. I stood there with my head down and hands clasped uncomfortably in front of me. "Do a twirl," she said. I slowly turned around, all the time conscious of the many pairs of eyes looking at me.

This pattern was repeated for each dress.

In the meantime Mistress had retrieved two frilly petticoats and just to add to my distress made me try each dress on again with the two different petticoats. Each time I came out into the shop I had to pull up the hem of my dress so Mistress could decide which petticoat suited which dress. After what seemed like a lifetime I was allowed to change back into my jeans and tee shirt.

At the counter Mistress handed me two of the dresses and one petticoat and told me to pay for them. The girl took my money and having wrapped the cloths passed them across the counter and with a large grin told me that she liked me in the shorter dress best of all. I melted inside.

Outside the shop Mistress informed me that I had behaved well and would be rewarded by a training level five when we returned home. I said I was very grateful for this judgment and hurried behind her, eager to get back to the house and serve at my new level.

  

  

  

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