5. A very bad experience!

OK… I have been putting this chapter off for over six months, but I’ve decided to finally exorcise this demon and share it with you. As mentioned previously, I consider the following to be one of the most stressful and upsetting periods of my life. *Deep breath* Here goes…

By the age of 19 I was dressing a bit more regularly. Thanks to the Rocky Horror Show the year before, I finally owned a few of my own clothes. Still living at my mum’s house, I kept them clumsily hidden at the back of my wardrobe in a plastic bag. By this point, my girlfriend was more aware of my feminine side and had become the first person I had ever opened up to. I’ll leave the full details of that story for another day, even though I really would love to digress right about now.

Leading a very active social life, one evening I found that I actually had some time to myself. Resigning to my bedroom that evening, I decided to get fully dressed up – dress, wig, heels, the lot. I enjoyed simply spending a few hours as me, doing the things I usually did, but with an added sense of inner peace that was usually missing from my daily routine.

I have always been somewhat of a night owl. My brain is forever coming up with new ideas, seeking stimulation or trying to make sense of this wonderfully complex situation that I have been born into. This often keeps me up most, if not all of the night, and I am always the last one in my street with a light on. It got so bad at one point that my sign to finally go to bed was hearing the milkman making his rounds at 6am.

However, tonight was not like those other nights.  I felt relaxed and settled down on my bed to watch some TV. Except I didn’t. I fell asleep. Fully dressed.

My next recollection is of feeling disturbed. I sensed that something in my environment had changed. Perhaps I’d heard a noise or was tapping into an unknown sense. Either way, my brain had become conscious again. As I slowly tried to open my tired eyes, I could see a blurry shape as my eyes tried their best to focus. In a single moment, two thoughts entered my head:

1. That shape is my mum! Why is mum stood at the side of my bed, staring at me?
2. Oh my God, there are strands of a blonde wig at the sides of my vision!

Somehow in the night I’d managed to drape part of my duvet over me. Did she know the extent of what I was wearing? Maybe she could just see the wig? My nylon-encased foot felt colder than my body so I quickly retracted it back into the duvet, with a high heel trailing behind it. I’m really not a morning person and usually operate in auto-pilot mode as I get ready each day. But this was different. My mind was racing but I was completely unprepared for this situation. My mum was still looking at me and I was essentially trapped with nowhere to go. It seemed like time had stopped, and as mum became aware that I was now awake and looking back at her, she immediately said: “Why are you dressed like that?”

Silence.

At this point, I didn’t even have a proper answer to that question. I had kept this part of me so deeply buried since I was young, that I’d never considered what I’d say if somebody accidentally found out, because I could never let that happen. Except, I just had. Still feeling incredibly groggy and with my heart racing out of my chest, I somehow got mum to leave the room.

As she closed the door behind her, I felt like my entire world had come crashing down. I felt very sick, scared and equally angry at myself. My secret was out and my brain had gone into overdrive. I immediately got changed into my standard uniform of t-shirt and jeans and stashed my clothes back into a bag. I knew that I couldn’t hide upstairs forever, so decided to go downstairs to face the music. I quickly walked through the house and made it to the bathroom. I brushed my teeth and then heard my mum enter the nearby kitchen. I waited a few minutes longer to see if she would retreat back to the living room, but she didn’t and I found myself trapped again, albeit with more acceptable clothing on.

As I made my way out of the bathroom, I walked over to the sink where she was standing. “Why were you dressed like that?” she repeated. I was truly still lost for words and didn’t know how to reply. So I didn’t.

She then said that I could tell her the reason and she would understand. Except, based on her reaction to me getting my ear pierced and having longer than average hair for a guy, I didn’t believe this to be true. I felt that she was just trying to lure me into a false sense of security as she fished for additional information.

The questions kept coming. “Are you gay?” she enquired? I responded with a very quick “no”. “Do you want a sex change?” she continued.  At that point, I just wanted the conversation to end and replied with another immediate “no!” I have since learned that these two questions are almost a right of passage that we all get asked at some point. I had pretty much shut down at this point (in panic mostly) and had nothing further to offer. Her line of questioning soon ran out as I didn’t give her anything additional to go on.

It had taken me 19 years to finally start to accept who I was and a moment’s carelessness to through it all away. I was incredibly worried and felt that my worst possible nightmare had come true. One thing was for sure, I could never let that happen again. I went back to my room and phoned up my girlfriend at the first opportunity. I told her what had happened and she was very supportive and helped calm me down a bit. She came round to visit that evening and helped me try to take my mind off of things. I tried to avoid my mum for the rest of the day, as I was embarrassed and didn’t want to face another round of questioning once she’d had time to think about it.

This, dear readers, is the bit that I like to refer to as the dumbest thing I have ever done. No, not the bit you have just read, but the next bit.

That night I was still pretty stressed and unable to think of anything else, decided to put the clothes back on, perhaps for the very last time. I immediately felt calmer again. Phew, that’s bett…zzzzzzzzz.

Yes, that’s right. I bloody did it again! But it was ok, because mum never came into my room when the door was shut and yesterday was a one-off. Except I’d managed to collect quite a few cups and plates during my self-imposed solitude and mum wanted to do the washing up. Again I wake up with mum looking at me. For how long I don’t know. But something was different this time. Her tone was angry. Again she questioned why I was dressed that way, and then said “I don’t mind you dressing like that once to try it, but two days in a row?”

I’m sorry. You don’t mind? Like, I have your permission to try on something for fun, as I would a cowboy hat at a joke shop, or somebody else’s glasses? But twice is not acceptable, because then I mean it? I again offered her no explanation, and with a tense atmosphere, nothing else was said on the subject.

In the days that followed, things remained awkward between us and she didn’t seem quite as supportive as she’d promised when fishing for details. One evening I came home from work and she seemed annoyed again. “Why have you got a bra? You don’t need one?” Great, she’s found my badly hidden collection of clothes and taken the time to remind me that I don’t have boobs. Thanks!

Again, I had no logical answer to this question. But I wasn’t going to get away with simply diverting the conversation elsewhere or saying no repeatedly this time. She wanted an argument and clearly had a lot of built up anger to vent. She threw everything she could at me, and used my secret as the ultimate weapon against me. Not only was I left defenceless as I couldn’t explain anything, I was heartbroken that the person I cared about the most in the world was using my most personal feelings against me. As the argument turned into a shouting match, she then said something that was the final straw. She threatened to hang all of my clothes out the window for the neighbours to see. That was it. I had to get out of there right away.

My girlfriend was still living with her parents at the time and I got her to ask if it’d be ok to stay there that night in the spare room. I packed some things and then made a quick exit. I was very, very upset. Of course, I was unable to offer her parents any explanation either. A week passed before I had finally calmed down enough to phone mum up. The conversation didn’t last long though and descended into an argument within moments. The phone was slammed down and I was back to square one. By this point I had run out of clothes so ended up borrowing some of my girlfriend’s brothers old clothes as I got mine washed.

I felt like I was outstaying my welcome as another week elapsed. My girlfriend’s mum persuaded me to try to phone mum back up. She was still incredibly irate but I managed to get her to hold fire long enough for me to agree to return home. From that day to this (11+ years later), the events of those two weeks have never been brought up since. She has however passed negative comments whenever she sees a man dressed like a woman on TV, and now doesn’t hold back in letting me know that she hates my long, blonde hair.

Things haven’t really been right between us since that fateful day. They are certainly a lot better but I always feel like the next argument is just around the corner. She made it very clear when I was growing up that she liked men to be men, which I guess stems from her growing up in the 1950’s with her Dad in the Navy. A big part of me has always wanted nothing more than to tell her exactly how I feel and explain what happened on that day. However, I also don’t want to give her any additional ammo to use against me in future arguments. While I am personally at peace with who I am now, the thought of my mum potentially wanting to use that against me is still very upsetting, and a situation that I really don’t want to revisit.

This experience also knocked my confidence massively, and I decided that my girlfriend’s reaction must have been a one-off fluke. If the relative closest to me had reacted so negatively, how the hell would everyone else react? I had no intention of finding out and my true feminine side retreated back to where it was safest.

So there you have it. That was one of the worst experiences of my life and is something that still saddens me whenever I think back on it. The good news however is that things did eventually get better and this certainly isn’t the end of my story.

Stay tuned for the next chapter, coming soon!

Kate x

4. The Time Warp!

Before I get on to what was arguably one of my worst experiences, I would like to share with you one of the best – up until that age at least.

When I was 18, I had already been dating a girl for the best part of two years. We did everything together and had a lot of fun (we still do in fact and are now married!). Anyway, I heard that the ‘Rocky Horror Picture Show’ was coming to our local theatre starring 1980’s music icon Jason Donovan.

For the unfamiliar, this theatrical production is based on the 1975 film of the same name. It is a sci-fi comedy musical where audience participation is highly encouraged. The story centres on a couple who have a breakdown near the residence of Dr. Frank-N-Furter (originally played by Tim Curry) – a flamboyant cross dresser.  I won’t say any more about it, but highly encourage that you seek it out!

My girlfriend and I had been to a lot of shows together so she happily agreed to go and see this. Knowing that many people went dressed up as one of the colourful characters (most of which wearing little more than stockings); I managed to persuade her to go in costume. I got the DVD and studied all of the characters, realising that I had quite an opportunity here.  I suggested that it might be fun if I simply went dressed as a girl, and to my surprise, she agreed.

Wanting to be authentic, I suggested that I should grow and shape my nails.  She also plucked my eyebrows and gently shaped them. I must say that it really hurt the first time, but experience has shown that adding a bit of moisturiser to the equation helps.  I also suggested that I should remove my body hair as it would look bad if representing as a girl. Of course, everyone else at the show would have unsightly hairs poking through their fishnets, but I wanted to make the most of my first (and potentially only) ever opportunity of this kind. She let me use her (quite smelly) Nair removal cream, which is something you apply with a spatula, wait 5 minutes, and then it chemically removes your hair. I stepped out of the shower with completely smooth legs, chest and armpits.

I also decided to get both my left and right ears double-pierced for the occasion. My girlfriend let me try on most of her wardrobe to decide what to wear on the night. After hours of skirt and top combinations, I finally settled on what was actually my favourite item of hers – a black dress with single red rose on the skirt.

One day a friend gave me a lift to college and noticed that I had pierced my right ear. At the time there was a stupid misconception that this meant you were gay. Thankfully nowadays this nonsense has mostly been forgotten. I explained that I was just going to see a show and he accepted this as explanation (see the valid excuse coming back into play!). A lady in the college cafeteria also complimented me on my nails as I paid for lunch, to which I simply smiled and said “thanks!”

Because my feet are much larger than my girlfriend’s, it meant that I had to go shoe shopping. Certainly not wanting to try shoes on in public, we went for the next best thing. In the shoe shop, my girlfriend placed the silver high heels on the floor, and I put my foot beside them as a stealthy measuring attempt. Fortunately they fit pretty well – beginners luck? The final bit of the puzzle was hair. At the time my hair was pretty short so a wig would definitely be needed. We went to the local joke shop which also sold a wide variety of costumes and hair. I selected a long blonde wig that I liked the look of, which wasn’t of the highest quality (I was a student after all).

On the evening of the show, I got ready at my girlfriend’s house.  As it was the middle of December, I wore a pair of nude tights underneath my barely black stockings to keep warm. After putting the rest of my clothes on, she helped apply my makeup. After applying foundation and powder, she applied eye shadow, mascara, eyeliner, lipstick and gloss. I was a relative newcomer to makeup at the time so felt safer in her hands! I then put on my wig, applied two coats of deep red polish to my nails and hung some dangly earrings from each lobe.

As we were at my girlfriend’s parent’s house, I was soon greeted by her mum who was surprisingly complimentary. She also said she loved my nails and asked if they were fake, and I told her they were real. Her dad didn’t really pass much comment when I saw him downstairs (probably for the best!) but did offer to take us to and from the theatre.  Upon arrival, I was relieved to see that a lot of people had got into the spirit of things and also dressed up. The show itself was great fun, with everyone joining in, throwing stuff on stage, and dancing in unison to the Time Warp.

It seemed to go a bit too quickly for my liking, and before I knew it, we were being picked up and returned to my girlfriend’s house, where I stayed over.  I guess I know how Cinderella felt when she had to leave the ball! Instead of changing right away, I quickly settled in front of the downstairs TV so that I could spend the remainder of the evening in the clothes. I remember feeling excited the next morning as I thought back on the evening before, a rare opportunity to go out in public as “me”.  I was also quite sad to begrudgingly remove the remainder of the makeup that I’d slept in, and cut off the finely shaped nails that I’d spent weeks crafting.

This event turned out to be a massive turning point for me. Not only had I been fully dressed for the first time, I’d done it in front of my partner (albeit with the show as an excuse), and even gone out for an entire evening in public. While I had to underplay the importance of the event to others as a bit of fun, it came to hold personal importance of a lifelong dream come true.  Also for the first time, I had my very own clothes, wig and shoes!

This was it. There was no turning back now…

Kate x

3. Getting pierced and teenage rebellion!

Secondary school wasn’t a particularly happy time for me. I went to an all-boys school (shudders) where you were expected to keep your hair short, not wear jewellery, and get routinely pummelled and covered in mud playing rugby. Testosterone was flying high and it really was a case of survival of the fittest. It was during this time that my desire to dress got buried to my sub-conscious, becoming something that I increasingly thought about but didn’t dare indulge in. Much.

It wasn’t all bad though and I took advantage of any small opportunities to be myself. I continued taking part in all plays at secondary school, which of course meant I could wear makeup (on stage at least). When I was 14, a new hairstyle came into fashion that is now known as the “curtains” haircut. For the uninitiated, this meant that boys would grow their fringe down past eye-level in a centre parting. At the time, this was the closest I could come to having long hair, and certainly the longest hairstyle I could get away with at my strict school.

When I was 15 I began to grow in confidence, thanks in part to the group of friends (consisting of guys and girls) that I had started hanging around with.  I remember always wanting to get my ear pierced as a child, but had it routinely drummed into me (without ever outwardly expressing an interest) that my mum was strongly against it. One Saturday in town, I had managed to persuade a friend to go and get our left ears pierced at a hairdressing salon. The actual piercing didn’t really hurt, but for some reason it did when they placed the back on the gold stud.

Anyway, we then had to face the problem of telling our parents. Having got the bus back to where I lived, we put off the confrontation for as long as possible by walking round the local park. Finally deciding to bite the bullet, I plucked up the courage to go home. Greeted by my mum as I entered the door, I quickly told her what we had just done.  She acted almost as if I was joking to start with, and then felt the need to get up close to examine the offending earlobe, grabbing it on both sides with her fingers to check its authenticity. She clearly wasn’t impressed and later started an unrelated argument, almost as a way of venting her annoyance at my apparent “act of rebellion”. She later explained that she thought I had done it on purpose to in some way ruin my uncle’s wedding that was two weeks away. On reflection, this made little sense to me, but she had at least missed the point that I was doing something that I considered to be feminine, as opposed to an act of teenage angst.

My friend’s parents had overreacted even more than mine, and immediately made him remove it when he got home. While I was begrudgingly allowed to keep mine, I still had to remove it every day for school, but cunningly kept the hole open with a small piece of a paperclip!

Here’s a tip by the way:  if you ever get your ear(s) pierced and then want to take the earring out to see what the hole looks like – DON’T! It’s almost impossible to put back in when nearly pierced and can be quite painful to put back in.

My mum’s reaction to getting my ear pierced when I was 15 would later prove to foreshadow what I consider to be one of the worst experiences of my life.  But I will leave that story for a future chapter in my diary (available exclusively at HappyDressers.com).

Thanks for reading and stay tuned for part 4, coming soon!

Kate x

2. A valid excuse!

My childhood was a confusing and conflicting time. As I grew up, I reluctantly crafted a male identity, which was created to appease a society that expected me to act a certain way.  However, my heart simply wasn’t in it and I glazed over at the mere mention of cars or football.

My personal encounters with feminine clothing were few and far between up to the age of 9; as access was limited to rare opportunities unsupervised with a borrowed item of clothing (usually underwear). I remember taking off a pair of tights and realising that the legs looked stretched and worn, so methodically crushing them back up before returning them to the drawer.

When I was 10, I remember being home alone one day as my parents went shopping. Instead of just trying on a single item of clothing, I thought I’d try getting fully dressed up for the first time. After putting on underwear (and struggling for what seemed like an age with a bra!), I decided to pick out my first dress from the wardrobe.  Being the late 1980’s, this was a peach floral dress with slight shoulder pads. Once on, I zipped it up and headed for the nearest mirror. I loved the feel of the clothes but remember being displeased at the boys face poking out of the top. I also slipped my feet into some oversized high-heeled court shoes. Unable to walk without them clumsily falling off, I simply stood there, enjoying the view at a slightly elevated angle.

Unsure of how long my parents would be out shopping, I thought I’d better put everything back and concoct a story of what I’d been doing with my time.  As I went to unzip the back of the dress, it wouldn’t budge!  I had stupidly become stuck in a dress and had an indeterminate amount of time to escape. Panic quickly set in and I struggled with increasing anxiety and force. It was then that it happened – I heard a rip! The dress was much looser now and as I took it off to survey the damage, saw that I’d torn one side of the zip from the garment, making a sizable hole in the back. As I returned the rest of the clothes to their homes, I had no choice but to take the dress into my bedroom and stuff it into one of my many hiding places. When my parents returned with numerous bags of shopping, they had no idea of my close call in a dress moments earlier as I helped myself to a packet of crisps. The dress remained hidden and unmentioned for many years later…

When I was 11, I discovered what would become a later valuable tool in my crossdressing arsenal – the valid excuse!  Taking part in a school production of ‘Joseph and the amazing technicolour dreamcoat’, everyone was required to wear white petticoats, a gold cardboard chest decoration, and get full makeup applied by a teacher. Foundation was sponged on, followed by eyeliner, mascara, brown eyeshadow and lipstick. As I stood with my theatrical classmates, they didn’t bat an eyelid as I chatted with them in my girly attire. It was then that I realised that all these rules regarding boys and girls clothing didn’t have to be set in stone – as long as you have a valid excuse!

I hope you have enjoyed reading my second diary instalment. Next time we enter my dreaded teenage years!  If you enjoyed this blog, please leave feedback and share it with your friends.

Kate x

1. Kate’s transgender Diary

I knew that something was different when I was very young. Perhaps younger than most. By the age of three I had become fascinated with all aspects of being a girl.

This is my diary, my story and my life.

I was fully aware of not actually being a girl of course, but felt somehow that I should be.  My earliest encounter with girls clothing comes not from personal memory, but from my mum retelling a story from my childhood. One day when I was three, my mum had some friends round to visit. She heard me call to her anxiously from upstairs, so quickly left her companions to see what was up.  She entered the room to find that I’d not only put on a pair of her sheer tights, but managed to pull them up completely over my head (I was three remember!), and in the process become quite stuck. Having come to my rescue, she thought nothing more of it and returned to her friends. Kids are curious beings after all. For me however, this was the start of what would become a lifelong journey of discovering my feminine side.

I remember later being envious as a neighbour of the same age nonchalantly applied clear nail varnish to her fingers one day. When she left the room, I quickly brushed one of my thumbnails with the clear enamel, hid it in my pocket, and then studied it for the rest of the day back home in my bedroom.  I was acutely aware that others would see this as wrong, but needed to know more about how everything ticked.

I listened intently as it was explained to me that I shouldn’t sit with my legs crossed in the car, as that was something that only girls apparently did. Until that point I was unaware that there was a lot more to being a girl then the obvious physical differences and the clothes they wore. A whole world of society created do’s and don’ts was slowly being revealed to me.

I remember one particular dress-up time at school when I was five. As kids squabbled over who would get to wear the Superman cape or fireman’s helmet, I had resigned myself to a playhouse, where I secretly tried on a green skirt and matching jacket.  During the end of the playtime, the teacher asked me to exit the plastic house and rejoin the other kids. I reluctantly stepped out in my green attire, and recall her saying how good I looked, rather than ridiculing me in-front of my classmates. These moments of exploration went completely unreported at home, as my fascination continued to blossom.

By the age of seven there was no doubt in my mind what I wanted to become. I felt conflicted in having to live up to a traditional macho role set by my father, feigning an interest in football, fighting and the like.  One night still sticks out very clearly in my mind, as a culmination of my feelings at that point in my childhood. I remember lying in bed, praying so desperately to God that I would wake up in the morning a girl. With a thriving imagination at that age, it seemed conceivable that if I really wished hard enough, I could magically transform into a girl. I remember wondering how I would explain my new appearance to my parents the next morning, but wanted it to happen so badly that I didn’t care. Of course, I didn’t magically transform, and I remember waking the next day, disappointed, as I found myself still trapped in the body that prevented me being the girl I felt that I really was.

I hope you have enjoyed my first diary entry.  Everything written above is the truth, and just the first step in what would become a lifelong journey in discovering, denying, rediscovering, and ultimately accepting who I was (more on that later!).

Thank you all for reading, and please bookmark this page and leave feedback. Stay tuned for my next diary entry, coming soon!

Kate x