Changing Roles
By Julie Dawn Cole
Chapter 23

I arrived home almost buzzing as it sank in how well my visit to see mum had been and then as a result of the way I was being treated by Emily and accepted by Pam. I was pretty certain that neither were of the opinion that I had been involved in deception or fraud and if indeed George had been involved in something then I wanted to give him the benefit of the doubt. How could I not notice? If he was responsible then why didn’t I spot it, it was my job to operate the business. Emily was making a far better job of it than I had been doing.

I removed my make-up and took a nice relaxing bath before bed and then set out my outfit for work the following day and a casual outfit for the evening. I opted for black leggings and a brightly coloured top for Manchester that I felt was safer than wearing the sort of clothes I’d worn on previous visits to the Gay Village. I knew that the leggings showed off my best features that were my well rounded and firm buttocks and hopefully Jack would be distracted if our chat was not progressing very well. I had some butt lift spandex underwear to help and to keep my frontage as flat as possible. I preferred to avoid tape since I didn’t think I could last all evening without a visit or two to the bathroom. I was hoping that Jack would be more friendly if he thought I was transgender like him.

I was up early since I was apprehensive about the meeting with Jack Garside and had not decided how to broach the subject of Georges involvement in setting up and funding of Jacks business and I needed a plan. Emily wouldn’t be able to help me much since she’d need to keep a low profile. In some respects, I thought it might be better if I was alone and Emily stayed somewhere close. The difficulty would be that being alone in the Gay Village might not be the wisest thing to do as tough as Emily appears at work.

I sat eating my morning muesli and sipping my coffee with the morning news on in the background. I started making a few notes on my scribble pad that usually was a list of shopping items I needed. First, I needed to explain my change in appearance since the last time I’d met Jack when she was Jackie. It had been a while and before she started her testosterone treatment and started living full time as Jack. George had confided in me and explained how sad he was to lose the chance of grandchildren but how proud he was to have the son he’d always wanted. Jacqueline had struggled in her early years through school and insisted to be called Jackie and she’d stood up to bullies. Most were girls not boys and whilst I never said anything to George I had suffered bullying problems too so I could relate.
George did tell me that Jackie was doing well at college and that she had started her own business and moved to Manchester and invested in a girlfriends bar/restaurant and seemed to be in a relationship. I didn’t realise that it was in the Gay Village that I’d visited a few times with friends. George never told me the name of the bar and I may well have visited it without knowing. As far as I knew Jackie was in a lesbian relationship and then she started living as a man and became Jack.

I felt it would be better if I showed interest in how Jack had dealt with her transition on the basis that I felt that I was born in the wrong body that meant I had been discriminated at work ever since George had left. My boss seemed to like humiliating me and my secretary, Sally had suggested that I resign and take legal action but my financial situation was not adequate to take the risk and I had heavy bills. I needed George but had to keep my distance but I needed to let him know that there was suspicion of fraud and both of us were the subject of scrutiny. I could try to feed back any information I could but not directly.

I hoped that would sound plausible and that Jack would act as an interface if I visited his partners bar regularly and met him. I thought I needed some sort of evidence of an investigation and hoped that Emily could give me ideas and agree to provide something. It had to be to do with possible involvement with an offshore company and not declaring it with the Company. I couldn’t think of a Plan B if this didn’t work. I would consult with Emily during the day.

I felt different today and I cleared my dish and mug and ate an apple whilst I went through what I might do if Jack became suspicious. There wasn’t much I could do if he didn’t believe me so I really had to act like the victim at work because of my gender confusion that had been exacerbated due to the sudden departure of George and my demotion to PA. I could say that I liked this change in role that suited me better but I’d have preferred that it was George who was my boss than this cruel and arrogant woman who had taken his job. I felt tears welling in my eyes so I found a tissue. I felt so emotional now that I’d not experienced to such an extent before, even when being bullied.

I felt that by coming to terms with adopting more of a feminine persona I was more comfortable with make-up and a skirt. I took a quick shower and readied myself for work. I took more time than I should have done because I kept stopping and admiring the image in front of me. This was what I’d dreamed of and I had Emily to thank for recognising it and giving me the push I needed. In a short time she seemed to understand me better than anybody.

I arrived at work a little earlier than usual and had left everything ready in my apartment for a quick change and freshen up before being collected by the car and driver I’d booked. We would collect Emily enroute since her apartment was on the way to the motorway.

Emily was already in her office when I arrived at my desk, and she’d left some fresh flowers to put in vases for her office and my side table. Another new job for me that I’d never experienced before. I knocked and opened her door and said good morning and took two vases from what used to be my cupboard. She said that I looked nice and that I smelled nice as I asked if we could chat later about tonight. I went to put the flowers in the vases before the office became busy and set off the coffee percolator. Hopefully it would still be at least half full by the time I got back from taking the vases to my desk.

When I returned Sally was there and she smiled and asked if I’d set off the coffee and ensured I filled our flask. She complemented me on my outfit and in turn I said that I was glad to see how well she looked and said that pregnancy suited her. She felt much better without experiencing the early morning sickness due to a change in her diet and some stomach medicine. I told her about my visit with mum and dad and what the manageress had suggested that worked. Mum had believed that I was my own girlfriend that amazed Sally and I admitted that her acceptance was a big relief since I could visit without worrying about changing clothes. We agreed to have a quick lunch together to chat more.

In my meeting with Emily later in the morning I outlined my ideas for the meeting with Jack that she felt should work. She agreed to provide some evidence of her scrutiny of Georges possible involvement with an offshore company in Virgin Islands which of course was a red herring. She told me that she would dress more appropriately for a visit to the Gay Village and find a friendly bar close to where I’d be meeting Jack and keep in touch by text. I told her that I was worried about her being alone but she assured me that she could handle herself and at the appropriate time she would join us once I was sure that Jack would not recognise who she was.

She shrugged her shoulders and smiled. ‘Jack has a girlfriend so why not you?’

I confirmed the arrangements I’d made for the car and driver before I went to lunch and updated Emily. She went to a meeting in the Board Room and Melanie was involved so Sally and I took advantage to take an early lunch. Sally wanted more detail about mums reaction to her sons surprise girlfriend who appeared out of nowhere. I told her that she’d moved in with me and we were talking of wedding bells. Mum had become more chatty that for a long time and she seemed to be stimulated by the news. It could go wrong but equally she might not remember any of it next time I visited.
At least the discussion about mums reaction to me presenting as my girlfriend kept us off the topic of Emily taking advantage of me and setting me up for a fall.

After lunch Emily called me into her office and provided me with ‘evidence of a Group Board Meeting’ to show Jack if necessary. It was supposed to be a copy of a notice to Board Members issued by her uncle reminding them to declare all outside interests, particulary involvement with offshore companies. There was even an extract from Board Minutes that looked genuine so we agreed that this ought to be enough to alert Jack and be fed back to George.

Both Emily and I left work early and I arranged that we’d pick her up at 6pm since it would take us about an hour before we were dropped off in the Gay Village. The driver would pick us back up around 11pm and would park close by.

I was nervous but excited as I got ready and changed into the outfit I’d set aside. Somehow the leggings worked much better than a skirt and gave me added confidence. I didn’t need any padding since I was blessed with natural curves and with the spandex underwear nothing more than a slight bulge was evident at the front. I’d plenty of experience of tucking myself and I managed to create a thigh gap that was another advantage of wearing tight leggings.

The driver called me to tell me he was parked outside and I thought I recognised the voice. To my horror it was a middle aged ex-employee of the company’s bank who I’d met several times at the bank. He looked at me with a puzzled expression. ‘Julian is that you?’

I was taken aback and stuttered a response. ‘Yes it is Wayne. Please keep this to yourself. We are having a night out in Manchester with a customer who is into this sort of thing and asked us to participate.’

‘Wow you look amazing. Better be careful. Don’t tell me you’re going with George?’

‘No chance. He is not with us anymore he is on leave and probably will retire.’

‘Oh well do give him my regards. Are we collecting your client? Or somebody else from your company?’
‘The latter. She is my girlfriend and she’s joining us to ensure that we don’t get into any trouble. Anyway what are you doing driving a car for our courier service company?’

‘I became obsolete. Banking is not the same with so much business online these days. It’s a young man’s game. Well young woman’s game if the truth be known. My job was taken by a young girl I’d trained a few years ago and she was promoted above me then she made me redundant. I’ve got a pension and a payoff, so this job keeps me occupied. For now, at least.’

I quickly sent a text to Emily asking her not to talk about George or her position since the driver used to work for the bank and knew both George and I. She responded immediately with OK that was a relief. I then said that I’d panicked and told the driver that Emily was my girlfriend from work and that she was accompanying me and we were meeting a customer who enjoyed visiting gay bars and regularly dressed in womens clothes. I said I was sorry but that was the best I could come up with on the spot.

When we arrived Emily was outside waiting. She looked amazing and I couldn’t believe it was her. She was wearing a low-cut figure-hugging bright yellow ress that finished half way up her thigh showing her stunning legs. She had at least 5” heels on so she would tower above me. Wayne let out a long wow and a comment. ‘Lucky you Julian. I think I’m gay if this attracts girls like her.’

Wayne jumped out to open the door and Emily slid alongside me and shocked me by kissing me passionately on the lips.

‘Hi Jules. That was a rush so I hope I haven’t kept you waiting. I hope you like my outfit. I wasn’t sure what to wear since we will be with your best customer. He’s notlikely to be turned on I hope. You said he’ll be in drag and most girls in the clubs like to show their assets.’

I could hardly speak. Emily had kissed me passionately and I was still trying to take in her body and her legs even though I’d seen them almost naked at the Spa. Adding a dress that showed her full cleavage and strong thighs had a dramatic effect. I suddenly felt the pull on my spandex panties. She smelled wonderful. I knew that there was a danger of Wayne being distracted driving on the motorway and saw his eyes light up in the drivers mirror.

Emily took my hand and leaned into me. She smiled and winked then whispered ‘Play along then’
I nervously responded and leaned across and kissed her on the lips. ‘There you are you minx. Have some of your lippy back.’

‘Oh Jules I’m so looking forward to meeting your friend. If he looks as good as you then I’ll be spoiled for choice. Is he bringing anybody with him?’

‘I’m not sure yet. He has a boyfriend, but he gets a bit jealous if he’s left alone and not centre of attention and this is supposed to be part business.’

‘Well Jules I don’t mind if she drags him away early. We can always hit a few bars on our own. I’m in the mood for a good time and it could be your lucky night.’

Emily more or less behaved herself for the rest of the journey with occasional lapses and each time she did she hitched up her skirt a little and I saw Wayne straining to get a better view. It was hard for me to tell whether Emily was putting on a show or being serious. She kept giggling which was so unusual since she seemed mature beyond her years at work. She was like a student on a night out dressed to kill. Her beauty put my efforts to shame.

Wayne dropped us close to the Gay Village on Princess Street that was close to the bar/club that is owned by Jack and his partner. We agreed he would pick us back up at the same place where Wayne could park and wait if necessary. I called Jack to let him know I’d arrived and he suggested to meet at a bar close to the canal that was quieter than most early evening and he’d arrive in about 15 to 20 minutes. Emily and I quickly walked their and found it and Emily found a suitable vantage point where she could sit at the end of the bar and get a wide view. My knees were trembling as I ventured alone to the bar and ordered a drink that was a weak vodka and tonic. Hopefully I could top up with tonic or even water if necessary to stay as sober as possible.

Since it was still quite early the bar wasn’t crowded and I found a small table with 2 seats by the window. I just hoped that Jack would arrive soon and that I’d recognise him. He had never seen me dressed as a woman so the responsibility was on me to watch out for men who were alone that seemed strange. I was approached a couple of times in the next 5 minutes but neither were old enough to be Jack. Then I recognised a face who was standing at the bar that I guessed was Jack. He was certainly different in his overall frame and stature but his features were still quite feminine. I waved as discreetly as I could hoping it was him and not someone who thought it was his lucky night. Emily was being chatted up by two guys as I glanced across and seemed to be joking with them.
Then I had a tap on my shoulder. ‘Julian is that you?’

It was Jack and he had appeared without me noticing him leaving the bar.

‘Yes. Hi it’s me but it’s Julie Ann now. You look so different, and I’m impressed. I’m so glad to meet you again and thanks for agreeing to meet me. I’m going through a difficult stage since your father went on paid leave and I miss him terribly. He was my mentor and I’m struggling with my identity and have nobody to help me. My only family are in a care home and all three are struggling and won’t return home..’

‘Let me get you a drink to calm you down and if I can help then I will of course.’

He brought me another gin and tonic but this one almost took my breath away. ‘That’s a real one with proper gin not one for casual visitors. I know the owner Cheers.’

I took another sip and this time I caught the flavour. I liked the taste.

Jack took the other seat and I noted the way he was sitting with his legs sprawled whilst I had to sit upright with mine crossed. ‘I must say Julie Ann you look cute and your make-up is impressive. Have you been to a salon?’

‘No this is my handiwork although I’ve had some coaching. ‘

Our small talk continued and I looked across at Emily a few times for reassurance. She seemed to be safe and comfortable and was chatting to the bar staff. Jack asked if I’d travelled alone and if I felt comfortable dressed as I was in a bar. I told him it was my first experience alone although I’d visited this part of Manchester several times with friends. I then said that I’d come with a girlfriend who would be meeting me later when I sent her a message since I wanted to chat with Jack alone.

‘So why the secrecy?’

‘Well as you can see I’m now dressing as a woman and I want to move on and consider taking hormones and maybe have a boob job and even more intrusive surgery when I can afford it. I just thought you might give me the benefit of your experience and also I wanted to try to get a message to George if you don’t mind.’

‘Well I’m not an expert on male to female and as you see I took testosterone and changed the other way. I’ve had a mastectomy and a hysterectomy, and the course of treatment was quite intrusive so I had to put up with a lot of scrutiny and prodding about. No point trying to be fitted with a penis though since I didn’t much care for the final result. I prefer to have some satisfaction and use my strap-on.’