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 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.

 

WGS208

 

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 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 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.

 

1

 

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 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.

 

wig

 

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 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. 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.

 

black and white studio photo of elegant naked lady

 

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 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. 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.

 

 A picture of a young woman resting her head on a towel over blue background

 

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. During the week, Katie was only at school for half of each day and had a day off on 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 about what was going to happen to me. The first chance to dress up had been going through my mind, it caused me to lose 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 parent's bedroom before they replaced it with the current vanity mirror. On top of that were numerous articles of makeup ranging from false nails to false lashes, along with lipstick, mascara, eyeliner 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 person 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.)

 

Transgirl

 

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.)

 

Transgirl

 

"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 was a pair of black loathers that she wore. Quite cute, if I do say so myself. Slip-on 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 beforehand. 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 makeovers. 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.

 

Objects of Desire - Stockings and Suspenders

 

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 a 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 hairstyles of Southern Belles of America and not Belle from Disney movie.)

 

The Actress

 

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.

 

Blue floral outfit

 

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 cleanup, 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.



Crossdresser Story

Ever since I can remember, I've been drawn towards femininity, from wearing my mum's silk nightdress when I was just four, tottering around in oversized heels and making a colourful mess of my face at the dressing table. It was good, it was girly, it was me... but it was wrong, or so I thought! I was a boy, and dressing up with makeup was for girls. But it was also so very right for the crossdressing transvestite within me. So my anxieties didn't stop me from my early experimentation, trying different lipsticks, playing with eye shadows and mascara, and looking on enviously as girls got to wear the clothes that I wanted to wear. 1The only girl's clothes in the house belonged to my mum, and they were far too big: not right the crossdressing transvestite clothes for me. Even then I just wanted to feel absolutely right as a girl: truly feminine and stylish. I remember growing up not knowing anything about being a crossdressing transvestite. I just remember liking girl stuff. Then, I saw a film on the television: to this day I don't know the name of the film, but it's had a long-lasting impression on me. It was about a man, who met and befriended some crossdressers. It was set in the 1930s. He was ‘straight’ (whatever that means), and they slowly brought him into their world with a little peer pressure, bit by bit. For him being a crossdressing transvestite started with a loan of a lipstick; he tried it, enjoyed it, and was a little turned on. When they met, they'd ask questions, and lipstick became mascara, blusher, eye shadow ... he tried a dress for the first time, stirring those crossdressing transvestite emotions deep within him: it was exciting, now for heels, lingerie, the hair and nails ... eventually, he was meeting his friends as a woman, he had ‘changed’ and it was natural. This moment was a life-changing not just for the man in the film but for me too. I didn't know other people felt the same; I hadn't heard of a crossdressing transvestite before and certainly didn't connect myself to being one. I needed to know more about this incredible world. 2These were the days before the Internet. The mere thought of being a crossdressing transvestite was taboo. Alone with only the memories of the film and a growing urge to become more feminine myself. But I wasn't gay: I don't fancy men. I was confused and didn’t understand. I always had a strange feeling of being a woman in a previous life, and drawn to a certain style of crossdressing transvestite clothes: long skirts, corsetry, long hair pulled back. Then I saw crossdressing transvestite adverts in papers: telephone numbers to call and speak to someone like me. This was too much to resist and I started calling other crossdressing transvestites just to chat. I'd dress up as a crossdressing transvestite as much as I could when my parents were out of the house, and just enjoy feeling complete. Then as I grew up, and started going out with girls, I'd be dating the girls I wanted to be! My crossdressing transvestite dream girls! I'd be attracted by their hair, clothes and makeup, and at times, and sometimes even tried some of their clothes without them knowing. I got a job and started earning money, but I couldn't buy my own crossdressing transvestite clothes. I had nowhere to put them. All the time, I was still one of the lads, I had many girlfriends and I kept my crossdressing transvestite secret hidden. I suppressed it for a while. 3I got married and have a wonderful wife and a couple of great kids. I love them dearly, but I still have the same inner feelings! I now know so much more of this crossdressing transvestite world. It's helped me understand that I'm not alone and that it's ok!! However, being a crossdressing transvestite is not something I'm willing to share with anyone - there's just too much for me to lose! I've tried the occasional dressing service for a makeover. I've bought makeup and heels the occasional dress, and become my true identity ‘Cassie’ every now and again when I'm in a hotel overnight away with work. But I always get a guilty feeling, a thought of I shouldn't be doing this. And when I look in the mirror, it's not the same crossdressing transvestite girl that's in my head. I want to enjoy my crossdressing transvestite life, and it's not hurting anyone if they don't know! But it's really difficult not being able to share Cassie with anyone! I've often had a fantasy of being kidnapped, and transformed into a woman against my will, and having to live my life out as Cassie: my delicious crossdressing transvestite dream! I'd stumbled across feminization hypnosis by chance, and saw a link to JJ at 'Dress Me Up'. Well, my first thought was, “She's absolutely stunning; she wears clothes that I could only dream about and her makeup is to die for.” I realised at that moment that I would have to meet her. UND957Could she help me become the crossdressing transvestite girl I'd dreamed about my whole life? Could she help get rid of the guilty feelings and give me the feminine outlet for which I craved? I put it off a few times and then plucked up the courage to call. She so understood right away and made me feel so at ease on that first tentative telephone call, that I couldn't wait to meet her and help find Cassie together. I booked a crossdressing transvestite appointment, and couldn't wait to get there. I booked a day off work but planned to travel overnight, allowing myself the luxury of going straight to a hotel after my visit. I pulled up outside her apartment, my heart racing by this point, and called to say I'd arrived. I knocked at the door, and when it opened I met my JJ for the first time. She was gentle, supportive, understanding ... and so completely sexy and appealing to all the senses: true sensuality with wonderful clear-headed intelligence and fun-loving personality to match. We sat and talked about Cassie, who she was, what she liked, what clothes, makeup, look, feel, her deepest desires ... I was in heaven, I haven't been able to talk like this with anyone in my whole life, and I had four fabulous hours ahead of me. This was the start of my crossdressing transvestite dream becoming a reality. lingerie_interstitial_01I stripped from my male clothes and stepped into the crossdressing transvestite unknown. I was guided to the bathroom, a bathroom with candles, feminine scents, perfumes, and cleansing lotions and face masks, I was about to start my journey, the crossdressing transvestite journey to find out who I am, who Cassie is. After cleansing my face, JJ had run me a luxurious bubble bath. I climbed in. I've had bubble baths before, but this was different, my senses were heightened with the depth of my anticipation. JJ brought me a glass of champagne and applied a facemask, to deep cleanse my face for my crossdressing transvestite makeover: delicious! I stepped from the bath, dried myself and pulled on a beautiful and feminine silken robe, stepped into the heeled slipper and I'm sure I glided into the boudoir. This was genuinely intoxicating, and I felt so at ease, chatting with JJ as if we'd been girlfriends for years. As I sat in the boudoir, we chatted about the crossdressing transvestite look I was going for. I'm a girly girl, not a tart or diva, so wanted just to feel as feminine as I could. I'd asked for some false nails, I've always wanted long nails, painted … so feminine. JJ had bought some for me, but didn't have any sticking pads, only glue ... acetone was used to remove them later. Well, I had business meetings the next day and had to drive to London, I couldn't run the risk of them getting stuck!

 

But, at that moment, I was becoming Cassie. The crossdressing transvestite atmosphere, the femininity of JJ’s boudoir and everything about the moment said to do it, be as feminine as you can be, enjoy it and live with whatever comes, it was titillating, exciting. The rush of crossdressing transvestite adrenaline I had when I said "do it" was a moment that will live with me forever! JJ asked if I was sure, but there was no turning back I wanted so much to be a woman at that point being a crossdressing transvestite scared and excited me in one go. As each nail was applied and glued in place, I started to feel like a girl. I changed inside, I felt Cassie taking over, I can't describe it, JJ kept winking at me, and I loved every crossdressing transvestite minute! My nails were on, and they felt like they were never coming off, we painted them, and my toenails, and then it was time to apply my makeup. The feeling of having foundation applied, powder, eyebrows pencilled, blusher, eye shadow, eyeliner, mascara and then lipstick was my every crossdressing transvestite fantasy, I now felt like a woman. I had desires I'd never known before. I wanted my dress and heels, I wanted my breasts to grow, and oh, how I wanted to stay like that forever. The Actress And perhaps the strangest sensation of all: I wanted a man: I was a woman and it was utterly delicious. Being with JJ had allowed me to go beyond being a crossdressing transvestite into true femininity. Don’t ask me to explain! My time that crossdressing transvestite afternoon with my JJ was the happiest few hours I've had in a long time, and only JJ and I know about it. This is only the start of my journey to find Cassie, but it's a journey I'm going to share with JJ. I can trust her, and she knows what I want, she'll help me get there. It was good, it was girly, it was me ... and it was so right!