All PG 13 The Crossdresser's Journey
This is a fictional account of how a young boy grew up and started crossdressing and what it brought him to in the future
Posted on
Add A New Story
(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.)


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.


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.


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.


I step forward in my life, and a lot had changed. Through secondary school things were a lot more different, and it was really the time in which I was able to shine. I gained an appreciation for theatre and dramatic arts, as well as arts in general and singing.
That all came during secondary school. I excelled in drama, music and dance, earning A grades for my final GCSE exams, and that train of education continued to college, again taking up drama, music and dance. I was told I had an exceptional singing voice, and to me, that was the ultimate boost for my self confidence. Many commented on the ability to sing with a falsetto which, when performing in musicals allowed me to perform as either a male or female character. I never admitted it to anyone, but I actually enjoyed playing the female parts more than a male. It wasn't just because of the chance I got to enjoy being dressed as a woman, but it was also down to the fact that I could fool people into believing I was a woman, and not a man in drag. Yes, at that time I still crossdressed. My idea that it was simply a phase was proved to be dead wrong, and during secondary school and college, my love for dressing up in drag was my dirty little secret. For six years of my life, only my sister knew about it, and that was before I came out to my college LGBT group. There was also the time I did it during school for three projects, all part of my GCSE practical exams.

I guess you are wondering what happened with my sister, and my parents in the past ten years, aren't you? Well, I'm going to tell you. I might have been called annoying and a pain in the ass by many, but I'm not a little **** bag like most of my generation.
Katie, as expected, passed through GCSE with flying colours earning straight A grades across the board. She excelled at everything she put her mind to. College came along, and then, it started to happen. My sister took a make-up course at College, much to my parents annoyance. I still remember it, shortly after she showed her choices, my parents focussed on the make-up course and moaned about it, considering Katie also took medical science, biology, chemistry and psychology like my parents were hoping for.

I should really point out what my parents do for a living; they are both doctors. Highly respected, and some of the top doctors in Southampton. They always had plans for me and Katie to get into the family business. I felt that they were grooming us, getting us ready for a medical profession of some sort. When school and college came along, I think I disappointed my parents in the respect that I wasn't going to get very far in the medical profession with the grades I had. During school I struggled with science, I'll admit it. I was lucky to scrape a passing grade at the end of secondary school. It was my saving grace, seeing as without the high grades in science, my parents accepted the fact that I was not going to be a doctor like they were. I think they accepted the idea of me going into drama.
I have to admit, with the idea that my parents would accept me as an actor in the theatre, then I would have come out about crossdressing sooner, but two things stayed my hand. The first were their comments on the comedian Eddie Izzard, saying he was a disgrace to comedians for prancing around in drag, and speaking openly about his transvestitism. My parents, are unfortunately very traditional (I might have said that earlier) and very vocal about what they believe in (my parents are also die hard Christians, but I won't go into too much detail. Long story short, my parents tried to raise Katie and I as Christian, but they failed. I won't go into my views of Christianity, as it would turn into one long rant). One of the things I can remember is that back in 2004, Katie and I were at home while my parents went to dinner. Apparently, they were sat next to a same sex couple and my mother, the bigot that she is, was incredibly rude towards the couple and asked to leave. When they arrived to pick Katie and I up from our aunt and uncle's house, they explained what happened. They thought I couldn't hear from outside the living room, but I heard it. I didn't fully understand it at the time, and I thought that my mother couldn't be that bad. Sure she had made comments about the LGBT community before. Now that I look back on it, I realise that she was capable of doing such a thing.

Readers, you'll have to forgive me, I went off topic. I'll finish up with talking about what happened to Katie, and then I'll get back on the original intended time line, as it were.

Again, even in her A levels, Katie excelled in whatever she set her mind to. The make up course was one of her favourite reasons for going to college. I had never seen her so excited. When she finished her two years at college, she went on to do another three years at the vocational college in the city centre of Southampton, specialising in hair and beauty. Again she excelled in that. Two years at the vocational college, and she passed with her certificates. I believe it was around that time that things went down hill in my family. Ever the traditionalists, my parents hated that Katie got through college doing what she wanted. My father once described Katie's education as “money being poured into the toilet, covered in animal crap and flushed into the sewer.” They disowned Katie, struck her off. I never forgave my parents. I lost my one link to doing what I enjoyed. Katie moved up with a friend to London, and though she was upset, she got on with her life and was enjoying work.


That's the past of my family for now. Any more of that and I'll probably end up writing the complete opposite of what I set out to achieve.

As I said, with Katie gone and out of the house, it felt colder for me. I never touched ladies clothing again until I was sixteen, two years after Katie left, and I was studying for my GCSE in Drama. We were tasked with putting on a performance of a fairy tale for our GCSE performance. I was in a group of six, all boys It was dumb luck that the girls had been put into all the other groups. I didn't really care at that point as there were a mixture of plays and performances to act out. It was by rotten (or perfect) luck, that we had to draw Beauty and the Beast (It was the Disney version, much to my dismay, I was hoping for the original). We all knew what was coming, there would be a mad dash to avoid playing Belle. Now, I had never came out with the fact I enjoyed crossdressing. While I enjoyed drama during school, during my last months of school in doing my GCSE practical exam, I was stuck with five of the biggest douche bags you could ever meet. They were... well there are few words that could be uttered and that still wouldn't be enough to describe how much of a douche bag each and every one of them was. I guess the Americans would see them as a mixture between jock and prep.
They carried on bickering in trying to figure out who would play Belle, and down to the fact I secretly enjoyed girl's clothes, and the fact that I wanted to pass GCSE drama, I took one for the team and said I would play Belle. It helped me in two ways; first it got that problem sorted. Secondly, it shut them all up.
Some of you may consider my treatment of the group to be quite harsh. I have to admit, two of the group weren't so bad. Adam and James; they were still a mixture between jock and prep, but not as bad as the others. Unfortunately James, who played Gaston in our group, passed away during our second year of college after being knocked down by a car. While Adam who played the Beast (and who I shared my first kiss with on stage), now resides in Australia. He left after we finished college. I still email him from time to time.
When the first dress rehearsal came along, I remember stepping into the gown I was going to be wearing. It wasn't like the original costume I wore back when I was eleven. This was a proper, full length ball gown without the petticoat to go underneath the skirt. I found it a little strange. The dress didn't fit me like I thought it would have done. I was so used to the skirt being given more length going outwards instead of being close to my legs. Still, I managed to hold my composure, and I went through the performance with a wig given to me (shoulder length brown wig with a plastic tiara) and thankfully, we performed to such high standards that my group passed with flying colours.

My music GCSE practical exam consisted of performing three songs. One was my choice, another was part of a group, and the third was a performance piece that I had to perform in front of an audience at the annual school concert during Christmas. Those days were nerve wrecking, even more so than my drama practical. I knew that I could become someone else with drama, but with music I had to sing, to be myself.
My choice of song came from Fear of the Dark by Iron Maiden. It was a particularly challenging song that pushed me to the limits of what I could accomplish. Seven minutes of pulse pounding, nerve wrecking singing that, if I do say so myself, Bruce Dickinson would have been proud of if he was listening to it himself. I remember the time after that I drank three bottles of water that day, and that evening I was paying the price for it. Still, it was part of my final grade in the end so why am I complaining?
My group piece was a choir song that we recorded during school. I can't remember the song exactly, though truth be told I don't really want to remember the song. My head and heart weren't really in the performance, if that makes sense, and I remember the hours spent rehearsing it with my class, and then the day recording it. I think at the end of the recording the one thought that was going through my mind was 'thank fuck its over' and that was a first for me. I had never said that about a day in music before. It was strange.
Now, I bet by this point, your wondering what my music GCSE has to do with crossdressing, well now it's time for the big reveal. I managed to talk my music teacher into letting me do a duet during the Christmas Concert. A friend of mine, Sarah (red headed girl, slightly overweight but still fun to be around, and smart to boot), she was a real tomboy, and I remember hearing her sing a Fairytale of New York (best Christmas song of all time) through out December, even before the concert was being planned. Sarah and I decided that we would sing the song, as a duet, but with the roles reversed. Sarah would take the role of Shane MacGowan, and I would take the role of Kirsty MacColl. I couldn't believe that we were actually going to go through with it, and then Sarah came up with the wonderful idea of actually dressing up. I was stunned, and I almost jumped at the chance of saying yes. Of course I didn't, just to keep up appearances. I had enough hardship being myself. If it emerged that I was a boy who liked crossdressing then the humiliation would come out at greater levels.
Word spread of the performance idea, and people talked. People laughed. People actually congratulated Sarah and I for doing something so bold and daring. I was half expecting ridicule and scorn, but it was the complete opposite. Both teachers and students welcomed the difference in performances.
The concert was going to be attended by the members of the school board, and the Southampton city council, as well as parents. This would have made me forget the idea, to tell Sarah that I wasn't going to do a crossdressing performance on account that my parents wouldn't like it. They were going to be out of the country. They were leaving me with my grandparents at the time. I confided in them of the plan for the Christmas concert, and they both supported me, but regretted the fact they were unable to attend due to being at the hospital. At that point I was expecting to be going through the performance on my own. That was when a shining star appeared in the form of Katie. I explained to her what was happening, and like the perfect sister she was, Katie promised to help with everything I would need. She stayed with me and our grandparents for a few nights. The parents might have turned their back on Katie, but they were the only two. Everyone else accepted Katie's decision.
My sister arrived three days before the concert, and a day after my parents left for wherever it was they were going. We spent the time at my grandparents house, going through everything that we would need to consider. Hair style, make-up, what I was going to wear. Some of the time we had Sarah with us, in which the three of us bounced ideas off one another and prepared outfits. I couldn't help but think that both Katie and Sarah enjoyed dressing me up. Katie had brought a number of clothes down for me to try on. We were trying to get a look of an English girl in New York city during the eighties. Sarah had already decided on a pair of trousers, a white long sleeve shirt, brown waistcoat with the buttons undone and her school shoes. Katie even suggested a cap.
As for me, after a day spent deciding on what clothes I would wear and what wouldn't look good, we decided on a red dress with a bolero. Knee high stockings and a pair of red pumps. Katie had provided me with a brown wig that reached down to my chest along with fake nails and eye lashes. On the day of the concert, I had talked the organisers to allow my sister into the school and help prepare me, and they did which was a bonus. We had a dressing room set up behind the stage. Katie and Sarah helped me into everything. Sarah had even provided a bra and stuffed it with socks to give me a modest pair of B-cups just to add to the illusion of being a woman. On the build up to the concert that evening, I was so close to crapping my pants I regularly visited the toilet and felt like throwing up. This was the first time I had performed in front of a large audience, and it would be the first time that I was dressed as a girl. I got a bit of a ripping from the other performers of that night, but none of it was too harsh that I had to worry. It was all in good spirits.
I was stunned to find that when we started our performance, I just sang. My nerves instantly melted and I just sang my heart out. Alongside Sarah, we were incredibly relaxed and just did what came naturally to the both of us, singing. The crowd loved it, they didn't even laugh at the two of us walking out on stage. We walked out, dressed as we were, our names were called out and we sang our song. When we finished, we were applauded. (They probably thought Sarah was I, and I was Sarah.)
After the concert, we returned to my grandparent's house. All three of us. My grandparents were still out of the house, and I can remember the chat we had in the evening. There was nothing special about what we talked about in all honesty. Movies, music, computer games. Same old same old really. I was going to get changed out of my dress, but both Katie and Sarah insisted I kept it on. Apparently, I looked cute in it. Those were Sarah's words, as Katie knew I looked cute in dresses. I was expecting her to actually reveal it wouldn't have been my first time in a dress. Though I think Sarah wouldn't have cared. She would have probably wanted to dress me up all over again. We had both just been crossdressing in front of an audience that consisted of council members, board members, students and the parents of those students. At that point I wouldn't have really cared.

My art course was next, and I had the idea of doing a project on the human body. It involved looking at all the layers of the body. The bones, the muscle, the skin, everything. I found that Leonardo Da Vinci's works certainly helped as reference points considering the work he did during his time on the human body.
I want to go out on a deviation of my story here, and comment on my fascination with Da Vinci. It moved far beyond the work I did during my art GCSE. The man was an intellectual genius. The world was better off with him. This was a man of many talents, and numerous mysteries surrounded his life.
My first point of call for my research was The Vitruvian Man, and then the Codex Atlanticus. The Vitruvian, by Da Vinci that focused on the human body. Unfortunately the Codex Atlanticus wasn't as helpful but still proved to be quite an interesting bit of reading material. My next piece for the art project was the human body in movies and literature. In movies, I focused on the German film Metropolis, the anime movie Ghost in the Shell (along with the sequel, and the Stand Alone Complex series) as well as both the original 1953 and the 2005 remake of House of Wax. I looked at how the human body was created through robots, the transfer of a human brain into a cyber body, and what was known as “Cyberisation” in the Ghost in the Shell series. For the House of Wax movies, I looked at how the bodies were used as the frames for their work.
(Author's note: I really wished I didn't watch the remake of House of Wax. The only decent part was seeing Paris Hilton have her brains skewered. Admittedly the original one was flawed. Vincent Price was a disfigured man wearing a mask, how was it that his lips were moving? Still, Vincent Price was a master of his art. It's a shame he's dead. Also, not many people know this, but there was a previous movie that the 1953 movie was spawned from called Mystery of the Wax museum. Another movie I need to get my hands on and watch.)
In the literature study of the human body, my only source was in fact Mary Shelley's Frankenstein. Now I realise that Frankenstein's work was to cheat death and create life, but what I found helpful for my art project was how Frankenstein created this life using body parts. How the doctor took parts from dead bodies and forged them into one complete body, and while he marvelled at his creation, he was horrified at what had been created (I still found that bit confusing, even to this day).
The final part to my art project was how people portray the human body in the real world, and this is really where crossdressing came into play. Thanks to the advice I gained from Katie, she suggested that I look at how people look in different forms. For this, I took a trip up to London, and I met Katie and a few of her friends. Since her time in London, she had met a number of different people: transgenders, transsexuals, crossdressers, drag artists, my sister had spread her mind far and wide and I was proud of that. Despite our parents still trying to make Katie see sense in their eyes, she still carried on and worked towards what she wanted. We had a lot of photo shoots set up thanks to Katie's girlfriend (she came out of the closet shortly after Christmas) who worked in a shop for the transgender, transsexual and crossdressing community. They were a huge help for me, and all came up with ideas that went into the final project. (I remember one Sunday when I was visiting, we used the store and there were about sixteen people all coming up with ideas. The best one was a spot the difference; a crossdresser fully made up to look like a randomly chosen girl who also went through the same make up procedure both wore the same outfit. A picture was taken, and the caption beneath both pictures in my project said “One is a male in girl's clothing, the other is female. Which is which?” and no one ever got it right.) I even remember I got to indulge in my habit of crossdressing for a few days.
Thankfully, all the hard work and preparation through art paid off. I received top passing grades and I went on to college happy and ready for the world. Of course I could have hoped my sister was closer to home, but beggars can't be choosers.


I'm afraid I can't really say College was all that eventful. In all honesty it was basically a copy of my GCSEs during school only this time they were replaced with A levels. I didn't do as much crossdressing as I had originally hoped. Seeing as I was at a college in which our drama groups consisted with enough boys and girls to fill the spaces required for each performance. I was a little stumped at that point, but it was bound to happen, to me it was just a dry point of my crossdressing life.
I did manage to visit my sister a lot more though. I started working at the local football stadium in catering during match days and any evening events that they held, and with the money from that, and a young person's rail card, I managed to visit her more and more during my free time. We visited the shop Katie's girlfriend works at, and while I wasn't able to fully dress up all the time, I was given a free make-over and I did wear a wig when I went up. A few days I was treated to half price make-over and dressing up sessions which was always a bonus to me.


I guess my biggest fulfilment of exploring who I am came during secondary school with my GCSE's and the fact I was able to explore the open world. I got to meet a lot of new people, some of which I still keep in touch. Some have gone on to lead amazing lives and push the boundaries for the LGBT community. Admittedly some of the time I wonder if the work done to help those who want to come out without fear of prejudice has been for nothing, but I then ignore that. The road to civil liberties for all and a fair and free country will always have bumps and cracks, but with perseverance we can carry on and achieve what's best for everyone. (Personally I believe the best way to start is through the abolishment of all religions, but that's just me.)

So that is the second part of my life chronicled, and put to paper. Now all that leaves is to chronicle the final part of my story, leading up to the current day.
Last Post
6 posts
These lovely people support all the features in Sissy Kiss to contribute to our community! So it would help so much if you could check them out, and say your from Sissy Kiss. Some even give discounts, or free gifts by mentioning it!
Add your message here..
Baby Butch
I enjoyed reading your story, it sounds like you had a good time being Katie's little sister. She dressed you in an amazing number of outfits, I like them all, especially the schoolgirl outfit. Your story is well written!
Thank you ^^ I'm glad you've enjoyed it.

I wish this was my life, but unfortunately not. It seems everyone believes this to be a recount with my life lol
A sissy of satin, but not frills. A sissy of length, and not thrills. A sissy that is a princess, and not a baby.

I am the first of each. Long satin gowns that turn me into the Sissy Princess I wish to be.
Well that's the second chapter up and on the website. Enjoy all
A sissy of satin, but not frills. A sissy of length, and not thrills. A sissy that is a princess, and not a baby.

I am the first of each. Long satin gowns that turn me into the Sissy Princess I wish to be.
first id like to say i loved your story  and if want your saying is 100% true i would love to hear your singing voice as well as get the adress to that shop in london that catteries to TTCD community  
 Princess are kind, brave, beautiful and determined they can do or be anything 
even change the world.  

 All girls are princess what you see in the Mirrors doesn't define you.
It doesn’t meter if you weren't born a girl. As long as your one at heart you too
are a princess 

I'm glad you enjoyed it, though its not true I'm afraid. If it was I have found a way of looking into the future :P It was just something that I made up a few years ago to get me in the mood for writing.

I do have a third part that could be posted.
A sissy of satin, but not frills. A sissy of length, and not thrills. A sissy that is a princess, and not a baby.

I am the first of each. Long satin gowns that turn me into the Sissy Princess I wish to be.
What kind of post would you like to make?
To post certain kinds of posts, like images, audios, or videos you need to be signed in first.