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March 26, 2012
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(Author's note: I am writing this at the age of 27, on Monday 26th March, 2018. While it might seem to be a far-fetched account, what you read is true. Everything happened. While I try to write an unbiased entry of my life, some of what I have written might sound biased. I shall leave you, the reader, to make up your own mind.)

-X-

It started when I was eleven years old, my fascination for girl's clothing and crossdressing that is. I remember watching my older sister Katie walk around in skirts, dresses, blouses, all clothing that was infinitely better than anything I wore. It looked nicer, and when I hugged Katie, her clothes felt nicer against my skin, a lot nicer. There were times when I was left on my own in the house; my parents were either at work or out for the afternoon, and my sister was visiting her friends. I had freedom of the house, and since my fascination started, I had only wanted to do one thing: try on my sister's clothing.

Many would have found it weird, an eleven year old boy wanting to try on girls clothing. I didn't really care at the time, I didn't know what kind of effects it would have on my future. At the time, when life seemed simple, I only saw it to be innocent curiosity that drove me to try on my sister's clothes. I didn't have any idea about the culture that followed it, I didn't know that men and women dressed in clothing of the opposite gender as a lifestyle choice, I would find that out much later in my life.
When I entered my sister's room, I had an idea of what it would be like. Pink, filled with girly things ranging from dolls to make up to posters of boy bands and actors. I was definitely mistaken. At the time my sister was sixteen and going through her GCSE's. Her room was painted a cream colour, very few posters decorated the walls, shelves were filled with books and not dolls, and she had a large wardrobe up against the wall. That was my first port of call. I opened it up, and was stunned to see everything hanging up so neatly. My sister was a bit of a neat freak, everything was out of place, and it was rumoured that she could see from first glance whether or not something was out of place. I always believed that Katie had some sort of second sight for these things. It was proved right when I was first caught by her. Coincidently, it was also the same day I started trying on girl's clothing.

When my parents and Katie had gone out, leaving me alone, I went into her room, and opened up Katie's wardrobe. I was instantly drawn to the dresses. She had a ankle length purple dress with straps. Now on Katie, it would have went down to her ankles, but when I tried it on, it went down to the floor, and even bunched up leaving a small tail of fabric. It didn't matter to me at the time; I simply stripped to my underwear and slipped the dress on over me. It didn't even need to unbutton the back of the dress. I looked at myself in the mirror that was placed on the inside of the door. My green eyes staring at the figure in the oversized dress. I felt the satin against my skin, and I liked it. I still looked like a little boy trying on adult clothes though, I had short brown hair back then, my parents choosing my hair cuts and how I looked for my time at school.
I was going to take the dress and hang it back up to try on another item of my sister's clothing when I heard the door open. Someone stepped inside, and I was unaware who it was until I Katie shout up to me.

"Rain! I'm home." she called out to me.

I guess you are wondering about my name. Yes, I am called Rain. My full name is Rain Alexander Edmonds. My sister is Katie Elizabeth Edmonds and my mother and father are called Rebecca and John Edmonds respectively. I don't know why my parents named me Rain, it wasn't to do with the weather, I was born on Saturday October 20th, 1990, and according to my parents and sister it was a sweltering hot day so how Rain came into the conversation is a mystery.

Anyway, back to the story.

When I found that my sister returned; the first thing that went through my mind was a close resemblance of the words "oh crap" ran through my mind. I still hadn't changed out of Katie's dress and my clothes were strewn over the floor. I was going to be found and instantly my mind told me to hide. I immediately jumped into the wardrobe, and closed the door behind me.
I remember that exact feeling when I was hiding from my sister. My heart was pounding, it felt like it was going to burst from my chest in a similar style to the Alien Quadrilogy. It would have solved some problems though, first off I would have been dead, and I wouldn't have to face my sister's wrath when she found I had tried on her clothes. She probably would have tried to resurrect my body and then kill me all over again for it.

"Rain, where are you?" I could hear Katie from outside the room, and I hoped she would think I was somewhere else. This was the moment I found my sister really did have a second sight. I overheard her muttering that she had shut the door to the bedroom before she left, and I foolishly left it open. She knew I would be in her room, and the fact that my clothes were left out for all to see didn't help that. "Come on Rain, I know you are in here. If you don't come out until the count of five then I will be forced to tell mum and dad." she stated with a calm and methodical voice. Katie didn't raise her tone, she didn't have to.

Knowing that Katie would tell our parents that I had been hiding in her room was really the only contributing factor of actually giving myself up. That and if I had continued to hide in her wardrobe, any chance of denying it would be useless considering I had left my clothes out. She started counting down, and I knew it was now or face the wrath of my parents. They would never have understood it back then, but it was likely that they had taken it down to a phase in growing up. The old 'curiosity killed the cat' saying. They would have forgotten it, and just told me never to do it again. I didn't even know how my sister would have reacted, but it didn't matter. I had to come clean and so, I pushed open the door to the wardrobe, and shuffled out into plain sight of my sister.

For a moment Katie was quiet, she just stared at me. I was expecting her to start shouting and screaming at me, ordering me out of the dress and to get changed.

I was definitely wrong.

Katie hugged me. She stepped forward and wrapped her arms around me, a smile was on her face. I was dumbfounded, awestruck, amazed that I wasn't deaf from the screaming and shouting that I had originally expected. She in fact explained to me that she had really wanted a little sister instead of a brother. I didn't understand it at the time, but if I did fully take into account the words back then I might have been offended, but I knew she still loved me. Katie told me she was happy having a little brother, and when she saw me wear her dress, she actually liked it. Sure she was a bit annoyed that I tried her dress on without asking, but she didn't let it overshadow the clear fact we had just come closer together. I explained to her my reasons, why I was wearing her dress and hiding from her. The fact that I liked the look and feel of girl's clothing, and was curious to try something on. Katie asked me if I liked it, and I said yes. I truly did like wearing Katie's dress, and I told her that I wanted to try more clothes on.

What she did next definitely surprised me. She took the dress off me and hung it up, instructing me to get changed into my previous clothes. When I was finished, Katie told me to follow her down to the basement. Now at the time when I was eleven years old, I had in fact been scared of the basement. My grandfather told me stories of monsters in the basement, and I'm ashamed to say that I believed him to that point.
It turned out that our parents had kept boxes of old clothes going back the years. Every outfit of value and importance was sitting in the cases. My first football kit. Katie's first ballet outfit. Both mine and Katie's school uniforms from school. Our parents had the odd habit of sorting things out into boxes with the ages written on, and it actually helped Katie with what she was doing. My sister brought out a box of clothes from when she was eleven years old. That was a great year, apparently. My aunt and uncle got married, Katie finished primary school, she performed the lead role in a ballet recital of Swan Lake, and there was the first family vacation, a cruise to the Mediterranean.
The outfits were going to be for me. Katie explained to me that she had always wanted a younger sister so that she could have someone to practice giving make-overs, and dressing up. Now that she had found out I wanted to wear girl's clothing more, she explained to me that she was going to dress me up, and give me the make-overs she had wanted to give to a little sister. I was filling the shoes of being Katie's younger sister, even if it was only at random dates and times. It would only happen when the parents were out. We would have started that day, but unfortunately our parents had returned earlier than expected. It didn't matter to me, or to Katie though. It was the start of something new, a fun new experience that would bring us closer together as siblings.

-X-

The first time we had together was the following weekend. Our parents had been invited for a ball in London. Katie had managed to talk them into allowing her to stay and look after me, without the help of our grandparents. During the week, Katie was only at school for half of each day and had a day off on the Thursday. During that time she went shopping, and she purchased a wig, along with a few essential supplies. The Saturday that my parents left, we got started. I found out about the wig, it was a blonde wig in the style of a pixie cut.
At first I was nervous of what was going to happen to me. The first chance to dress up had been going through my mind, it caused me to loose track of my school work at some points during lessons. My parents weren't too pleased about it, but they just told me to pay attention at school. No one asked why I was distracted, something I was pleased to have avoided, but I could have easily used any excuse to get out of that. Luckily, the weekend came by quite quickly though, and soon, the Saturday my parents left for London came around, and Katie and I were left alone.
I thought we were going to start with what Katie called a 'dressing up session' straight away, but my sister had other ideas first. She told me to wait upstairs, and so I did. I sat for an hour playing computer games, at the same time I was getting anxious, I couldn't wait to try on the clothes, and when the time came, Katie called me down to the basement.

Katie had been busy; she moved things around, creating two separate areas. The first area consisted of an old vanity table that had taken Katie a great deal of time to move out, and to fix the vanity mirror back on. It was made of white wood, and it had sat in their parents bedroom before they replaced it with the current vanity mirror.
On top of that was numerous articles of make up ranging from false nails to false lashes, along with lipstick, mascara, eye liner pencils and eye shadow sets. Various blush colours were ready, and the contributing brushes. Numerous foundation tubs were waiting with cotton wall pads. Next to the mirror, was a bust of some persons head made from marble. According to Katie it was a very expensive piece in which they had to be careful. (Little did we realise that three years later, my dad would only go and break it while taking it to be appraised and possibly sold on.)
The second area was for dressing up. A clothing rack of all the outfits I would be trying on had been set up, with a dressing screen and a basket to put the clothing I had been wearing at the time. Nothing was spared, Katie had thought of everything for what they were going to do. She had prepared bottles of water and glasses, a few biscuits and some snacks, she had even brought the phone down into the basement so that if their parents phoned like they said they would, then  we wouldn't raise suspicion by being late to answer. (Our parents once scolded my aunt and uncle for not answering the phone by a certain time when they looked after me and Katie. It was purely because of the fact we had been sat out in the garden enjoying the sun.)

"What do you think?" Katie asked as she watched me walk on towards the vanity table, and then walk onto the rack of clothing that she had laid out. Katie had brought her bridesmaid dress out, the white gown with the green sash wrapped around the waist, tied in a bow behind, and the puffed sleeves. A pair of green flats had been brought to wear with them.
A pink gown with a darker pink sash, a dark pink rose attached to the front of the bodice and two strips of satin to wrap around the arms was hanging behind it. That had been Katie's gown when they went on the cruise.
Her school uniform: A red pleated skirt, white long sleeve blouse, knee high socks and a bow tie. (my sister went to an all girl's school that gave her more ideas than just being a make-up artist, but we'll get to that later.) Sitting at the bottom of the rack of clothes were a pair of black loathers that she wore. Quite cute, if I do say so myself. Slip ons with a bow at the front of both shoes.
The next outfit was a costume that Katie had purchased during the week of Belle from Beauty and the Beast. There wasn't another outfit hanging on the rack after the Belle costume, but according to Katie she was going to try and dig some more out for me, just to give an experience of wearing clothes other than those of a formal nature.
I was both happy and nervous by that fact. I would have been happy with just trying on the outfits Katie had prepared before hand. I knew what was coming, but hearing the prospect of something new being prepared gave me a small feeling of dread in the pit of my stomach. I didn't know what to expect. Still, whatever was going to happen was happening because I wanted it to. My sister didn't have to force me, she didn't have to use blackmail or threaten to tell the parents.

The first part of the dressing up session was Katie sitting me down on the chair and getting to work. Katie worked on the foundation, covering my face and correcting the tone of my skin. Katie certainly was an expert at giving make overs. While she worked, Katie explained to me that she had volunteered to help out at her school during the past year with the drama department, helping out with the make-overs for every actress that was performing. Of course it was kept under wraps because of our parents, but I'm thankful that Katie actually kept up her make-up practice.

After about forty-five minutes of working on my make-up, I found myself looking like a little girl which I was stunned to see. I looked in the mirror and from that point on I was known as Rin (again, it's a strange name, I know. My sister liked to read fantasy novels, she still does.) and I was Katie's younger sister.
The next task for us both was to get me dressed. My sister took me behind the dressing screen where she... well I won't go into detail. You probably get the idea of what happened. I emerged moments later in white girl's underwear and a pink dressing gown. While I sat down and had a biscuit, Katie went on and prepared the first outfit. I was dressed up as Belle. Now that was a weird outfit.
Petticoats on first, all three of them. I could never understand how women could wear those things. The gown afterwards was made of satin, and actually quite comfortable against my own body. I was surprised it fitted me. While I was being dressed, my sister explained that she purchased the outfit for a twelve year old. It would be a better fit on me than that of an outfit for an eleven year old. I didn't understand it back then, but as time went on I came to understand that every outfit was different in terms of the body shape. The body structure between men and women are different, and so that while costumes will be the same age, the shape of the female outfit will not always fit the male body. (God I hope that made sense.)
The outfit had everything; the gloves, the shoes, even a wig, though we kept that off as it looked completely ridiculous. I wouldn't have looked like Belle. This wig was short, curled with ribbons in the hair and unfortunately very irritating. (Looking back on it, I think the wig was styled after the hair styles of Southern Belles of America and not Belle from Disney movie.)

That afternoon, I relaxed and took the weight of keeping my crossdressing secret off of my shoulders. I was happy, thankful that Katie was there with me, talking me through the stages of getting dressed up, the fabrics used to create every outfit and what they meant to me. Katie explained everything.
Amazingly, I was expecting something a little stranger and longer, but Katie dressed me in every outfit, explained what it included, and why they were being used and what for. A lot of it I had a vague idea, I remembered the cruise and what my sister had worn was for the formal evening dinners. That was just one of the gowns she wore, and as much as she looked, Katie couldn't find the other two evening dresses she wore, which, in all honesty wasn't much of a problem. I had tried on numerous clothes at that point and there were other times in the future that Katie and I did similar activities.
That weekend, I was stunned to be offered £50 to be dressed in whatever my sister dressed me in, and while I was expecting something very feminine and scary, it wasn't too bad. During the rest of the afternoon and the evening, I was dressed in something similar to my sister's old school uniform. A pink knee length skirt, white socks, pink trainers, a white long sleeve blouse and a denim waistcoat. That was before dinner, in which I was dressed in the bridesmaid dress that I had tried on a few hours before, and I slept in a set of baby blue footsie pyjamas. Amazing, one evening, a night and a morning of being dressed up by my sister and I earned £50 from it. I didn't tell anyone about it until I was seventeen years old and part of a college LGBT group. It was discussed between myself and my friends.

The next morning, we found our parents wouldn't be back until later that evening, so it gave Katie enough time to set everything right. She cleared all of the make-up, and I helped with clearing up the basement, even while wearing my sister's chosen outfit. We got through the clean up, and I was back into my original jogging bottoms and t shirt by 4 that afternoon. Our parents returned an hour later, and they were none the wiser.

-X-

That was my first experience in girl's clothing, and it happened more and more, every time my parents were out, when they went out for an evening, when they went on holiday or to a friend's party out of the city that they chose to stay at a local hotel. Katie always managed to talk my parents into letting us stay to keep an eye on me, and every time we dressed up. Over the months the costumes became different, from various Disney princesses, to more formal dresses that Katie had managed to rent from the costume shop that was a short distance away from where we lived. Katie and I had never been closer with the experience we shared. She got the chance to practice her make-up and I was able to dress up.

I thought it would have been a simple phase that every person went through. They develop a curiosity towards something. I had friends that took up smoking in secondary school, drinking, some had even taken drugs and ended up in prison (Okay so that last example might not be the clearest, but you get the idea, people change, and those that did end up in prison didn't re-offend... as far as I'm aware). Little did I realise that crossdressing was going to be a major part of my life, and it would change everything.
Well, the first part of my three part crossdressing story, and my first attempt at writing in the first person point of view. I'm hoping it has gone well, and I guess only the readers can tell me that. Anyway, this is an account of a fictional character that shares a few similarities.

This is a story, with an idea of how I wished my life could have been. I won't deny, I often wish I had an older sister. In this story, there are some elements that link me with the character of Rain, but for the most part this is an entirely fictitious portrayal of my life.

I hope you enjoy it, and remember, comments are always appreciated.
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:iconpattygirl8848:
pattygirl8848 Featured By Owner Aug 24, 2014  New member
i love crossdressers
Reply
:iconsallyane:
sallyane Featured By Owner Feb 1, 2014
wonderfull story it sound like me but ihave to do in secret but its enjoyable love this story
Reply
:iconterrazero20:
TerraZero20 Featured By Owner Feb 1, 2014  Hobbyist General Artist
I have the same problem myself. Its really difficult to break free and do something like that
Reply
:iconsallyane:
sallyane Featured By Owner Feb 1, 2014
yes i agree still i do when ican it helps me relax& have some time to myself
Reply
:iconterrazero20:
TerraZero20 Featured By Owner Feb 1, 2014  Hobbyist General Artist
I'm hoping once I've moved out of the house I can start dressing more
Reply
:iconold-crow:
Old-Crow Featured By Owner Jan 20, 2014  Student Traditional Artist
Very believable, I thought it was real the first time through. Fantastic little touches like all the attention paid to the sensation of fabric, cuts, shapes, and fashion terminology really sell both the realistic and personal aspects.

Well done. :clap:
Reply
:iconterrazero20:
TerraZero20 Featured By Owner Jan 21, 2014  Hobbyist General Artist
I'm glad you liked the story, and its good to see people are still reading it.
I keep looking back at the story as a whole, and I wish that it could be me, that it was my life I was writing down and living out. But alas, I'm stuck here.
Reply
:iconold-crow:
Old-Crow Featured By Owner Jan 21, 2014  Student Traditional Artist
Your stories are apart of you, it was your life. That's the great thing about writing, in my opinion. :nod:

I'm kinda a hobo and definitely an idealist. If you have a dream of the future but don't know how to get there, maybe I can help. I've been stuck before, almost died from it. I'll take you seriously, if you like.
Reply
:iconterrazero20:
TerraZero20 Featured By Owner Jan 23, 2014  Hobbyist General Artist
Hmm that does make a lot of sense. Everything I have written about does stem from something that has taken place once in my life and so it does come down to being written in my fiction.
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:iconcaitlinbosch:
CaitlinBosch Featured By Owner Jul 18, 2013  Hobbyist Photographer
Lovely story, I really enjoyed reading it
Reply
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