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Best crossdressing stories

Kittie

Years: 31
Hobby: Horny House Wifes Searching Amateur Sex Single Older Women Search Huge Cock
I prefer: Man
Gender: Fem
I can speak: English, Russian

Feeling pretty and looking alluring is what I have so come to love. Being feline and attractive is my basic and one goal as a transvestite.

About me

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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.

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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 a 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, Best crossdressing stories went into her room and opened up Katie's wardrobe.

I was instantly drawn to the dresses. She had an ankle-length purple dress with straps. Now on Katie, it would have gone down to her ankles, but when I tried it on, it went down to the Best crossdressing stories 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. I'm home," she called out to me.

Crossdressing

I guess you are wondering about my name. Yes, I am called Rain. My full name is Rain Alexander Edmonds. 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,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.

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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.

This was the moment I found my sister really did have 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.

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 Best crossdressing stories 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 the 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.

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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 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.

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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 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.

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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 in 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 the 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.

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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. The first time we had together was the following weekend. Our parents had been invited to 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.