Changing Roles
By Julie Dawn Cole
Chapter 33

As I approached the station entrance, I spotted Jina and as our eyes met she waved to ensure I recognised her. How could I forget her after just a few hours apart and her similarity to my boss. They both had the presence to stand out amongst a crowd with similar stature and striking hair colour. Jina let hers hang loose blowing in the slight breeze and it was hard to think she had been Emilys younger brother since she looked so gorgeous. I was pretty certain that Em could look just as striking if she let her hair fall loose and added a few highlights but she seemed a lot more focused on her job than her appearance.

Despite it being a cloudy, sultry day Jina was wearing cut away shorts and a tight fitting top displaying her perfectly formed breasts. She had fabulous shapely legs that attracted the gazes of passers-by, especially men, and I was sure she was enjoying every moment. There was no doubt that she had made the right choice to live her life as female and it showed in the wide smile across her face. We kissed and hugged each other gently as we met.

She spoke first. ‘Hi Jules you look nice today. I’m so excited that you agreed to meet so that we can have some private time together. I think you’ll enjoy the experience with my friend and my sister is going to love how you look after my friend has finished with you.’

I felt nervous and a little awkward to be dressed in feminine clothes in broad daylight on the High Street and Jina did her best to keep me calm treating me as a friend even after spending such a short time together the night before. I still had the feeling that Jina thought I was an experienced cross dresser and that she thought that Em and I were in a relationship, especially since we were staying in the company apartment together. I’d hardly had much chance to chat at length with her but she seemed to know more about me than I would have expected considering she wasn’t supposed to be in regular communication with Em. Surprisingly things hadn’t been as awkward as I anticipated between the two of them so Em’s story that she needed my support so she could be comfortable at the party seemed more of an excuse to spend a weekend with me than fact. I’d resisted showing my private life to anybody before Emily took over but she seemed to give me little choice ever since she decided to force me to carry out menial tasks and affect my confidence. It had taken a while to regain my composure and smile.

‘Isn’t it wonderful to enjoy being women and to spoil ourselves? I’ve been able to experience it full time for more than two years now and before that I just used to crossdress part-time like you are doing. I’m so looking forward to getting to know you and maybe I can help you build your confidence and consider becoming a woman as I have done. If we can meet up regularly hopefully I’ll find out what you think of my sis and she’ll let her guard down. I can already see how much she’s changed since we left home. But I wonder if she is as bossy with you as she was with me.’

I decided to be as honest as I could about the real reason I’d agreed to accompany Em. ‘Well I want to be truthful to you Jina now I’ve seen that you and Emily have come back together. I haven’t known her that long and she took the job that I’d been doing as well as the responsibilities of my boss that made me very angry at the time. But she treated me fairly and she is certainly unique. I think that she is doing an amazing job, much better than I was doing.’

‘Oh well I didn’t realise. You seem so right for each other.’

‘I admit that I was scared of her at first when she was sent to our company to re-structure it and I had other problems besides work that affected my confidence. She told me that the board felt that I was hardly qualified to do the job she was designated to do but I was older and had more experience in the industry. I had no choice but to do as instructed and she almost humiliated me by giving me a role with no power that was low level with a lot of administration duties.’

‘So you were in charge until she arrived. That must have been embarrassing?’

‘Yes I’d had a secretary to do these things she asked me to do. I realised that for some reason she was trying to help me because she actually respected my knowledge of the business so my opinion soon changed. I can now see why your uncle sent her to take charge of the business and sort out the problems. She soon stamped her authority and she seemed to identify what was wrong in the business from day one. I don’t need to worry about the consequences of my decisions anymore. I actually look forward to going to work now and already I would do anything for her.’

‘So why did you just cave in. Did the job mean you had to dress as a woman? Couldn’t you just take the role as a man.?’

‘Well you know Em far better than I do and I think she likes to be the dominant one at work and socially and she ensured that I knew who was in charge from day one. She soon found out somehow that I was a crossdresser and that I had transvestite and transgender friends and took advantage of me.’

‘It’s hard for anybody to hide that if the truth be known. We all slip up.’

‘I guess she saw that I was quite excited by her treating me like a female employee and maybe that was why she made a rule that employees should wear uniforms and it gave an excuse for them to exploit my feminine body shape because of my hips, thighs and butt. She arranged that one of my former staff to buy the uniforms and since most of our office staff are now women she selected a design to appease them and very few sets were ordered of male size. I was issued with womens trousers that unsurprisingly fitted me very comfortably.’

‘That sounds like Em. She’ll have soon had a plan to find your weak spot.’

‘Since then things just developed but I can’t complain because Em has treated me very well and I soon adapted to the role as her secretary. I found myself adopting feminine mannerisms and female colleagues treated me as one of them.’

‘That sounds encouraging. She likes to be in total control and to feminise men and if you don’t mind I hope it works out. For both of your sakes. So you aren’t in a relationship then?’

‘Not exactly. It’s no different to most bosses and their secretaries I suppose. Can you keep a secret if I tell you something in complete confidence?’

‘I have no reason to tell anyone anything you tell me whether it’s in confidence or not. So feel free to tell me anything you like.’

‘Well after we had been drinking last night I found myself in a compromising situation with Em. We’d both had more to drink than we expected and I don’t think either of us could stop ourselves and we were in the company apartment with no one else around. Things developed from nothing and in the end we slept together. It was a first for me and as wonderful as it was I doubt that Em considered it to be serious. I never slept with anybody before, male or female. It was amazing for me and I sensed that Em enjoyed herself but she didn’t say anything about it this morning. But even so,she did seem different at breakfast.’

‘Well let’s see what she thinks when my friend has worked her magic. I have a lot to thank her for so hopefully you will have the same opinion. You’ll be surprised by her skills.’

‘It sounds a bit scary. Is it going to be expensive since I’m not as well off as people think because of my commitments looking after family in care homes.’

‘Don’t worry she is a close friend and we used to work together. She owes me a lot of favours and Bennie too so there won’t be any charge’

We headed into the station to purchase underground tickets so I found out we were heading to the West End where most theatres are located and where there are lots of restaurants and bars.

‘Does your friend work in the West End? It will be quiet at this time of day won’t it?’

‘Yes and yes hence it’s a good time for her to help. She has a business there with two other people and they have a thriving business supporting several of the theatres and drag shows. They supply costumes and Fiona specialises in make-up. She is transgender and she used to work in the clubs and we met when I worked behind the bars when I first left home.’

‘But I’m sure that I’m not transgender even though I’m dressed like this and working now in a job that is usually associated with women. Until Emily came into our company I had a normal life as a man, even though I was slightly built and smaller than most of the men who reported to me. I was just a part time crossdresser and I kept a low profile and didn’t harm anybody. It was a secret I kept from even my closet colleagues at work, not that I had many friends. But I guess somebody spotted me when I was out with friends I met on the internet. ‘

‘So we all started out in the closet until we recognise that it is not illegal as long as we don’t visit female bathrooms or expose ourselves. You clearly have no problem passing and your practice crossdressing has clearly paid dividends.’

‘But this was not in my plans and it was forced upon me by your sister. Now I seem to be almost full time with no time to be myself anymore. My life is just a whirl so I haven’t even considered living as a woman it’s just sort of happened and no doubt my promise to come to your party with Emily gave her an excuse to go further. My outfits have become feminine and I’m wearing make-up and have had treatments and re-styling of my hair. I have a job that is more associated with female employees so I look and act more female at work so this look socially is the consequence. I now have to be at Emily’s beck and call and outside work I’m visiting and helping my family so it’s hard to get back control of my life.’

‘Don’t tell me that you don’t like this change because from my observations you look so comfortable and content. You seem happy enough so it doesn’t seem like you put up much of a fight.’

‘What choice did I have? It seems that Emily soon found out all about my past personal life and possibly even before she arrived to take over from George. Then she soon put me in a situation where she challenged me that was embarrassing for me. I couldn’t lie. She seems to be able to be able to read people and then extract the truth whether it’s business or personal. Once I admitted it she encouraged me to take my crossdressing experience to a new level. To start with she insisted that I wore a uniform at work then I was tricked into accepting it was gender neutral. But it wasn’t.’

‘That sounds like my sister. But believe me this look suits you. At home I could never hide my liking to dress in her clothes and I kept it secret from my parents until it became impossible for me to be the boy they wanted. It was Emily who exposed me since she found me dressed one day. It gave her the chance to become the favourite and she started to boss me around. But don’t worry about how you present here in London. It’s not something you need to hide and anyway you seem comfortable dressed as you are and you’ll fit in perfectly at my party. Wait until we get back. It’s my betting that even Em won’t recognise you and that you’ll be amazed by Fiona’s amazing skills. I am sure you’ll trust her advice and you’ll like her.’

As we travelled the underground I was aware of the number of heads that turned to stare and I hoped it was to admire Jina but for sure they seemed to include me. Jina seemed to enjoy the attention so she responded and walked rather like a model on a runway turning occasionally to smile. She could swing her hips as good as any young woman trying to catch attention. I hardly dare look anybody in the eye in case they laughed or made derogatory comments.
Luckily the underground wasn’t overly busy like it is on a weekday during rush hour, so at least we could walk quickly and we weren’t pestered or squashed like sardines. I did have one scare when a group of female passengers approached us to ask if we were on our way to a Pride event like they were. I assumed they had recognised that I was male but it turned out they were part of a group of lesbians from Brighton and they assumed Jina and I were a couple. Jina burst out laughing when I said that they looked normal and I coloured up with embarrassment. She said I’d be meeting several of their friends later who would likely as not confuse me even more so she recommended to keep an open mind and treat everybody the same whatever their appearance.
We arrived at Leicester Square without any further incidents or confrontations apart from some mild touching and the occasional suggestive comment from a group of men who were old enough to be my father and were on a weekend break with their wives who had gone shopping. They were heading to a football game of some sort and were drinking canned beers. I still felt very nervous as we left the platform and found our way up the escalators to the exit to street level. Jina was still very protective and had insisted to hold my hand squeezing it gently from time to time that helped a lot.I know I had feared the sort of touch that happened in the Crocadile Dundee film a few years ago when he was told that a woman who was at the bar was actually a man in drag.
Leicester Square itself was very busy with lots of weekend visitors and sightseer’s so luckily I didn’t have to worry about being noticed or challenged even if my masculine features stood out. Not that I needed to worry since I’d not encountered any problems so far at work, nor in any of my outings since my job had changed. I was getting paranoid I supposed because I was losing my real identity.
Luckily we didn’t have to join the throngs anyway since it was only a short walk from the station before we turned into a side street that is where Jina said that our destination was located. We soon arrived outside the shop front. It wasn’t so much a shop but more like a small theatre foyer much bigger than I expected. It was almost a Victorian style frontage so I couldn’t help feeling that it must be very expensive to lease, especially in this location. On entry we were met by Jina’s friend Fiona who was strongly built and several inches taller than both of us and a few years older.
She was very friendly towards Jina and they hugged for a while before Fiona turned her attention to me. ‘Now then who do we have here Jin, a new friend of yours who we’ve never met before. She is not local or I’d know her because she is very beautiful. Why are you both here and requiring my help. Of course whatever it is you want it will be my pleasure.’
I turned to Jina and stuttered a reply saying that I didn’t understand because I wasn’t expecting anything but that Jina asked me to accompany her to meet a friend. There was only some talk of a makeover for Jinas party later. It turned out that Fiona had arranged some assistance for the evening so would be attending for a few hours. She was in the business of supporting performers from several shows and reviews in the West End with prosthetics.
‘So you aren’t just a make-up artist then’
‘No I help with longer term make-overs that don’t need hours in make-up pre-shows and focus on transformations rather than pure drag. More subtle changes to the body rather than anything extreme. Prosthetics have come a long way in recent years. Sometimes I help transgender friends out so it helps them decide their ideal body shape for their build. For you with a small chest and narrow shoulders I think a 36C bust might be ideal. It keeps the right proportions. Although you are quite wide across the hips for a man and maybe a 38C or D is an option.’
I was almost speechless. I couldn’t wear breasts full time. I needed to retain my masculine identity even though I was being treated as female at work. Mum and Dad would be horrified if they realised what was happening to me. I was their only son with no cousins and they hoped I’d marry one day and they’d have grandchildren despite their aging decline.
‘Come on Jules don’t be scared. It’s not permanent and Em will be happy. She said as much to me last night. You’ve been accepted as female at work and just look at you today as we travelled the tube. We both fitted in with the group of girls heading to a Pride event. I’d love to have been going there and for you and Em to join me. Let Fiona do her magic. You’ll be amazed.’
Fiona reached for a display album and coaxed me to sit whilst she showed a variety of options with some very happy customers. So many variations of shape and size.
‘Come on Julie let me see you stripped to the waist and we can clean your skin and remove any traces of body hair to ensure we get a strong bond.’