Monday morning, feeling very smart and professional but very nervous, wearing my new skirt, jacket and heels, and with a light daytime makeup I reported for work., I met up with Tom for a briefing and he then passed me on to his Head of HR for an induction.

“Jacquie, this George Coulson, the area manager covering all the shops in the West Midlands area, he will introduce you to the store management and will be keeping an eye on your training programme.”

“ Hello Jacquie, pleased to meet you, you will be working for three months in our new flagship store in the Bullring Shopping Centre next to Moor Street Rail Station in Birmingham, it is usually very busy and will keep you occupied. I will go in with you today, and as I believe that you are living in Stratford, I suggest that, rather than drive in, it would be easier for you to commute by train in future.”

As it was on a direct line from my office and home in Stratford-upon-Avon, and as the 50 minute train trip was as fast as driving in heavy city traffic, this was a useful suggestion. We went in by train so George could show me the best route to the store, he walked me around the store so I could get a feel for the size and scope of it, and introduced me to the manager that I would be working for. The set up was a lot bigger than I had imagined it was huge multi-floor store, and I thought that it might take me longer than planned to get to know the right people who could give me some ideas.

As a trainee manager I was treated with a bit of wariness by everyone I met, they were all pleasant enough but I felt that there was some barrier there. As a trainee and therefore potential manager, the general staff saw me as a future boss and didn’t want to get too close, and the managers saw me as a possible future rival and didn’t want to pass on their years of experience, and were also wary of me coming in fresh from management training with all the latest ideas and strategies which would change their settled routines.

I spent the first week moving around the various departments, in the warehouse on stock control, on the shop floor working behind the counters, in the finance office dealing with orders and customer accounts, and with the store detectives learning the limits of their power and authority. None of it was in depth or too detailed, just enough to give me a basic insight into how the shop operated. Nothing seemed particularly out of the ordinary and there was no obvious fraud or mismanagement and I had nothing really to report, via Joanne, to Ted. I had been accepted without question as Jacquie, I tried to be friendly with everyone and draw their confidence and was beginning to get treated as just another member of staff. There seemed to be a strict hierarchy amongst the staff and the different grades did not really mix. Even in the staff restaurant/canteen, the general managers and admin staff all sat in the same area, as did the heads of the various departments or buyers, the senior assistants, and the juniors.

Whilst most people used their time in the canteen for relaxation, the buyers always seemed to be in deep earnest conversations, looking around them to make sure nobody was listening. They had quite a lot of authority and ran their departments with a great deal of freedom within the guidelines of the company rule book. I decided that the junior staff did not have the opportunities to abuse the system to the extent that Tom had suggested, and that the finance and general management staff were too remote from the sales floors and stock control to be able to interfere too much.The ordering process, goods received and stock control operations were fully computerised and constantly monitored by Head Office and did not leave too much scope for fraud, so that meant that my time really need to be behind the counters on the shop floor with my main focus being on the buyers. Although purchasing policy and stocking levels were now all centrally controlled at head office, the heads of departments preferred the title of ‘buyers’, harking back to the days in independent stores when their predecessors did actually determine what to purchase and negotiate with suppliers.

I was assigned to the main women’s wear department and quickly got to know the other girls, joining them for tea-breaks and lunch. Along with a lot of general gossip, discreetly and gently I pumped them for information on their buyer, Jane Simpson.

“How do you all get on with Jane, she seems a bit old-school and keeps a distance between herself and the rest of you, but she seems ok.”

“She likes to think she is a cut above us all, always flaunting new clothes and shoes, going on about her days out at the races, fancy restaurants or exotic holidays, and generally living a very comfortable life. She treats us ok but I wouldn’t trust her as far as I could throw her, or say anything that I wouldn’t want repeated.” replied Sue, one of the senior assistants.

“ She stays in her office most of the time and really only comes out to tell us we are doing something wrong or to collect the returns which she takes back to her office for inspection and sorting. Even if we are very busy she won’t help out at the counter, she thinks she is too important for that.” added Sally, one of the juniors.

Even as a buyer, her salary would not have justified her lifestyle. She definitely needed my attention, so I tried to work as near to her as possible to keep an eye on what she did.

Jane did not get too involved with sales, that was the responsibility of her junior staff, but they always had to refer any requests for returns and refunds to her. Like most major retail chains, the shop operated a ‘return in 28 days for a refund if you are not happy for any reason’ policy. Even though there were changing rooms for customers to try items on, most of the returns were because the fit wasn’t right, but many were brought back because the product had defects, marks, or snags. Anything with no problems was returned to the general racks, anything with minor defects went onto the discount sales rack, and anything considered too defective was written off and disposed of.

In the screened-off area that Jane liked to call her office, there were two racks for returns, one for discount sales and one for disposal. Normally the discount rack was quite full and the disposal rack almost empty, but when she was at lunch I inspected the garments on the disposal rack and was surprised to find that that the majority seemed perfect and some of them had quite expensive designer labels, and took a photo on my phone for future reference. At the end of the day I stayed behind on the pretence of catching up with my work and when the others had all gone I inspected the racks again. The bargain rack items were virtually as they had been at lunchtime, but the disposal rack was almost empty, all the good stuff had gone and only the cheaper or badly marked stuff was left. It was the same the next day and the day after and I felt this needed taking to the next level.

“Joanne I need you to do a couple of things for me, please arrange a meeting between the two of us and Tom, and get him to check the staff entrance video cameras to see if Jane Simpson was carrying parcels or large bags when she left at the end of the previous days.”

We arranged to meet on the Saturday evening at a hotel overlooking the river in Stratford. Tom had said that he could not stay for a meal but wanted to talk things through with me. We had arranged that Julie would join Joanne and me for a meal afterwards and make a night of it, so she styled my hair and helped me with a heavier evening makeup, I put on my LBD and heels, and went off in a taxi to collect Joanne, Julie would be joining us later after we had finished our business.

We walked in to the hotel lounge and Tom was sitting in a quiet corner seat where we would not be heard. He already had a bottle of Pouilly-Fumé in an ice bucket and four glasses waiting for us. He rose to greet us and welcomed us both with a hug and a kiss on both cheeks, and then blushed when he remembered who I really was under all this appearance.

“The pair of you are looking gorgeous tonight, you seem to be really getting into the role Jac…quie, you are a natural. I’m sorry that I can’t stay with the pair of you longer. Before you start your report Jacquie, I have checked the videos, Jane Simpson seems to leave most nights with several carrier bags, what is the significance.”

“ I haven’t got the full story yet but I am certain that she has some sort of scam going on where returns are written off, some of them for quite expensive items, and she takes them away with her, Whether she is just taking advantage of the returns for her own benefit, or whether there is a more organised operation I have not yet discovered. Even if it is just her taking stuff for herself, from what I have seen, it could easily add up to many hundreds, if not thousands, of Pounds a week, and the gossip is that she has quite a lavish lifestyle. I also suspect that she is not alone in doing this, if it’s not a bad choice of phrase, she seems ‘as thick as thieves’ with the other buyers. I think you need to check the store accounts for the level of returns and write-offs, you might be surprised. How far do you want me to go with this, do you need evidence to take her to court, or will you want to hush it up and just get enough on her to encourage her to resign?”

“It depends on what we can find in the accounts, but from what you have told me I think it is likely that we will want to prosecute. You’re doing a good job, keep going at it, and give me updates daily via Joanne. Unfortunately I have to go now and I’ll leave you to finish of the wine, enjoy your meal and night out.”

He left us with a quick goodbye hug, but no kiss this time, I gave Julie a call to join us, and while we waited for her taxi to arrive Joanne and I cleared up bits of business in relation to other clients.

“You really are amazing Jac.…quie, I am surprised at how easily you have adapted to life as a woman and fitted in with the girls you are working with, and got them to give you the gossip to point you in the right direction, and you seem to have at least started to unearth what is going on, I can see this leading to a lot more opportunities for us.”

Julie soon joined us and business talk stopped, we were now just three very attractive young ladies enjoying a night out. We had an excellent meal, mainly fish-based rather than heavier meat dishes, which were complemented by another bottle of the very drinkable Pouilly-Fumé. I was beginning to now think automatically as a woman and looking after my figure, although we did finish off with some amazing creme-brûlée, and chocolates with our coffees.

On Saturday nights there was a regular dinner-dance at the hotel and we were soon up on the floor enjoying ourselves. Towards the end of the night the band started playing slower numbers and we were going back to our seats,

“Would you ladies care to have a dance with us, it seems a shame to leave you sitting at your table.” said one of three very well mannered and very good looking young men who suddenly came over to us.

“We’d love to, thank you for asking.” said Julie, before I had a chance to turn them down, much to my dismay as I wasn’t looking forward to intimate dancing with a man, despite how I was dressed and appeared. We finished off the evening with some very slow romantic dances with them. Although I wasn’t getting the same buzz as the girls, I was beginning to enjoy being held tight and feeling another body close to mine, It had been a long time since my last relationship and I had almost forgotten what it was like. It was soon time to go home, although I think that the fellows would have liked the evening to continue, but they were perfect gentlemen, gave us goodnight kisses, helped us on with our coats and saw us into our taxis.

“Thank you for inviting me to join you tonight Jacquie, I really enjoyed it, it’s been a while since I had a good night out, we should do it more often.” Julie said as we sat unwinding at home with a glass of wine.

“ It was my pleasure, you deserved a treat for all the help you’ve given me and letting me stay here. When I next speak to Joanne I’ll see if she fancies doing it again next week.”

“Are you sure that you are alright with this, Jacquie seems to be taking you over, you were enjoying yourself too much dancing at the end of the night with that young man? I know that I
encouraged you into this for your halloween day, but you seem to be taking it quite seriously now.”

“Have no worries Julie, you are right that I am enjoying dressing and being treated as a woman, but I am just making the most of the short time it will last for, and it seems to have been successful business-wise too. I wasn’t keen to have those slow intimate dances but in a way I did enjoy the close contact, even if it was with a man, but I would rather we didn’t get into that situation again. We’ll get the investigation finished and think about it all again, but at the moment i am comfortable being dressed and appearing as Jacquie.”

We had a relaxing day on Sunday and decided to play the part of tourists. Although we had lived in Stratford all our lives, it was many years since we had visited any of the popular sites and so spent the day among the hundreds of mostly day-trippers thronging the town. Wrapped up warm in tweed trousers and jacket with wooly hats holding our hair in place against the chilly breezy autumn day, we wandered around town arm-in-arm, to the RSC theatre, the home of the Royal Shakespeare Company; to Holy Trinity church with Shakespeare’s grave with the unusual epitaph “Good friend for Jesus sake forbeare,
To dig the dust enclosed here.
Blessed be the man that spares these stones,
And cursed be he that moves my bones.”;
We visited what is reputed to be Shakespeare’s birthplace, although there is some doubt if it is the actual property, and went down by the Avon to watch the boats and the swans drift by. The hustle and bustle of the tourist trail was a world away from the pressures and stresses of work, and set me up nicely for the new week.

On Monday I was again in Birmingham, back to keeping an eye on Jane. I had not had any feedback from Tom, but then I expected that it would take him a few days to make any progress.
One of my first customers had selected and tried on a stunning Adrianna Papell full-length evening dress in a sapphire blue satin at £275, which was a good start to the week for me. However I noticed late afternoon that it had been returned and was sitting on Jane’s discount sales rack, which I photographed, and later it had disappeared altogether. It now became clear that this was more than just casual opportunism by Jane, but was part of a much wider scheme, and wanted to talk it through with Joanne.

“I think that friends or colleagues of Jane are buying the more expensive items, returning them, she is writing them off and stealing them and selling them on. Can you keep an eye on eBay, Amazon and Pre-loved and similar sites for anyone selling an Adrianna Papell full-length evening dress in a sapphire blue satin.

She soon called back “You must be psychic, you are right, I’ve seen it on eBay being sold from a site registered in Birmingham. I’ve already arranged for Margie, one of our better operatives, to go to look at it and find out who was selling it and exactly where.”

She deliberately arranged to send someone who she knew the dress would not fit so that she didn’t actually have to buy it after inspecting it. Later the next morning I received photos of the shop, the dress and, included in the background of the picture, the person making the sale. She was remarkably similar to Jane and my guess was that it was her sister,

“ Hi Jacquie, I’ve managed to trace Jane Simpson’s Facebook account and had a good look through it, there are lots of photos of her and her family, and Margie says that the woman selling the dress is definitely her sister”

“Ok Joanne, keep Tom up to date, but ask that he takes no action for the moment, I think that there might be more to come out of all this.”

Now certain of what was being done and that we had Jane under control, I needed to widen the net. At lunchtime I sat as close as I could get to the buyers table, left my phone on voice record on maximum sensitivity, and tried to listen in to their conversation. Later at afternoon tea-break I found a quiet corner to play back my recording, which was actually better than what I had heard personally

“ That was a good idea of yours Jane, We all now have our own versions of dealing with returns, The shop doesn’t pay us what we are worth, and selling on some of the stuff makes up for it.”

“I don’t know why we didn’t think of it sooner, in my cosmetics department it is easy to write off returns of the expensive perfumes as ‘damaged packaging’ or ‘given it as a present, tried it and it doesn’t suit me.’ ”

It appeared that all the other buyers that Jane had lunch with were carrying out similar operations and that they were all in it together, it must have been costing the company a fortune.

I arranged to meet Tom that evening after work at a bar down by the canal basin in Birmingham, and filled him in on what I had found and emailed him the photos and recording for his records.

“I’ve checked the return and write-off figures for that store and they are the highest in the group running into many tens of thousands of Pounds a year, but had been missed because the accountants are more interested in sales figures and stock turnover. Overnight I have arranged to get covert cameras installed in the ‘office’ of each of the buyers you have identified to get a record of them actually removing items and putting them into their bags. I’m very grateful to you for what you have discovered, can you stay on for the rest of the week in case I need anything else.”

I was pleased and proud that I had made the operation a success, but was disappointed that my time as Jacquie would be coming to an end. As the store management and girls I was working with had been told that I was being moved to another store, several of us had a farewell night on the town together, doing the tour of the bars in Broad Street and ending up at Carluccios restaurant in Brindley Place. As we had gone out directly after work most of us were just in our normal working clothes, but we had all cleaned and refreshed our makeup for a more dramatic evening look and got a lot of admiring looks and attempted chat-ups as we went around the town enjoying ourselves. I had only been at the shop for a short time, but I considered myself lucky to have made such good friends, and promised to keep in touch.

The next week Tom came to see me in our office to update me on the progress of his investigations.

“We now have unarguable evidence of what was going on, and Jane and the other buyers have been asked to leave and have been advised that it is likely they will be prosecuted for theft and fraud and face jail sentences. As a result of your findings, in all our stores the policy has been changed so that all returns, not put back on sale, will have to be returned to head office for inspection and possible return to our suppliers, and the buyers will no longer have the discretion to write goods off. Thank you for your time and for a job well done, send me you account and I’ll make sure it is settled in full, and don’t forget the expenses for your transformation into Jacquie”

Jacquie mostly disappeared, at least from the professional point of view, and Jack was again very much in charge of the business. However Jacquie did make a return to the Birmingham store, where the gossip on the jungle telegraph was all about my role and what I had discovered.

“That was pretty clever of you, we had no idea what she was up to, once items disappeared into her office, we were told that it was none of our business what happened to things. We would never have guessed what you were up to, you just fitted in as another of the girls sent to us to get experience before getting on the managerial ladder. If you are in Birmingham give me a call and we’ll all go for a catch-up drink.” Sue told me.

The place had been in turmoil for a few weeks while new managers were put in place, mainly from the senior assistants in the various departments affected. The girls were all happy with Sue as their new buyer, as she treated them with a lot more respect than Jane had, and we agreed to all meet up occasionally to have a catch-up, Jacquie was never going to go away completely again.

As I was now regularly going out socially, shopping, and on trips, with Julie and Joanne as Jacquie, I moved house to a property that was a bit more secluded and where I was able to come and go discreetly without being easily seen by neighbours and it was getting to the stage that more of my life outside work was being spent as Jacquie not Jack. I had my hair trimmed shorter so that it could be brushed and styled to suit me as either Jack or Jacquie, but missed the feel of it brushing my shoulders as I walked.

Although in my personal life, I was now becoming comfortable as Jacquie, in my professional life I was very much still Jack.

“Joanne, I think that a lot of our clients will not be comfortable suddenly having to deal with the new me, I’m concerned that it might affect our business, what do you think.”

I think that as most of our company’s work involves female investigators that should not be an issue after the clients have got over the initial shock. We still have the same team of investigators, the same level of experience and know our clients operational methods and problems.”

I decided that I could trust Tom Chapman enough to discuss it with him, and arranged to meet him at a restaurant near his office, I felt that neutral territory would be better for the discussions we were about to have.

“Hello again Tom, I’m glad to hear that everything has now settled down at the Birmingham store, I have been talking to some of the girls there and they now seem a lot happier and more comfortable at work.”

“You are right, you did a really good job there, appointing you and solving it has been a ‘feather in my cap’. As well as the directors being pleased with the result, I’ve had a lot of compliments about my special undercover investigator, you, and how well you got yourself involved with all the staff. I have been asked if you would be prepared to follow up on another case, not directly working through me but personally for our finance director, I don’t know the details as he is keeping it all quite close to his chest. The only thing is that he has asked for the same investigator as I used in the store, which would mean you becoming Jacquie again, how do you feel about that.”

“In a way that is what I wanted to talk to you about, this may shock you, but please hear me out before you say anything. When I was carrying out the investigation for you, as Jacquie, I became very comfortable in the role, I enjoyed working with the girls and their company when we went out socially, I came to like the feel and style of the clothes and the general femininity of it all. In my personal life I now regularly dress and appear as a woman and I am considering going full-time with it, but I am worried that this may alienate some of my clients. You are the only person I have discussed this with, we’ve known each other for quite some time, and I trust you, please be honest with me even if you want to say something that I may not like, what do you think?”

“You really know how to spring surprises don’t you? Personally I can’t quite understand why you want to do this, I have obviously seen many articles in the newspapers or on TV about transvestites and transsexuals, but have never really grasped why they go down that path, and have never knowingly met anyone like that. However when you were in the shop you were very convincing, you were a natural, and if you decide to go down that path I don’t think you will have any problems being accepted as female. As you know, when you were Jacquie I accepted you and treated you as another woman, it was sometimes hard to remember who you really were. Other than me, nobody in our organisation was aware of your real identity, and nobody questioned me about you, they realise that as Head of Security, I have to keep some of my methods and personnel confidential. As far as our company is concerned there will not be any problems, but I can’t speak for anyone else.”

“ How do you feel personally, will you be comfortable with me working with you and maybe even meeting for the occasional business dinner or drink.”

“ I’ve been there and done that with you already, it might take a bit of getting used to but I am not worried about it.”

“ Ok, thanks for that, I feel a bit happier about it now. If I am going to be involved with another project with you, I may get Joanne to take a higher profile with some other clients, so that they see her as the face of the company, rather than me. Tell me what you do know about this new investigation and where we go from here.”

“I know nothing at all other than there is something serious that needs dealing with. I can arrange for you, as Jacquie, to meet with our CFO, Henry Donaldson, to talk it through, I expect it will be in the next few days, it does seem urgent. I also suggest that you need to become completely natural as Jacquie again, and spend all your time between now and the meeting as a woman, in the office as well as at home, you need to live the part, just as you did before.”

“Thanks for everything Tom, I appreciate it a lot, you could quite easily have walked out in disgust, and threatened never to work with me again. Let me know what the arrangements are with Henry Donaldson.”

That had gone a lot better than I had expected, I had to share my thoughts with someone , so asked Julie and Joanne to come round to the house for dinner that evening. To get in the mood for discussions about a future as Jacquie, I changed into comfortable female clothes to get the house and the meal ready for my visitors. As I would be Jacquie for the immediate future, I fixed on my breast forms as they took me most of the way towards feeling feminine, dressed in a cotton deep-v-neck half-sleeved top, skinny jeans and comfortable shoes, a bit of light makeup, earrings and locket necklace and bracelet, Jacquie was back again.

I took out a side of salmon from the freezer and left it to defrost and acclimatise whilst I tidied up and dusted and cleaned the house, prepared the asparagus, potatoes and tartare sauce to go with the salmon, made some lemon sorbets as a post-meal refresher course, and made a wholemeal bloomer for toast to go with an Ardennes paté starter. With everything for the meal now prepared I was ready to start getting myself ready.

I used hair remover on my arms, legs, chest, and shoulders, showered using a scented body scrub, towelled and powdered myself dry and started on creating Jacquie. My hair was too short to take rollers but long enough for me to style it with a heated brush and tongs, I gave it a light spray just to hold it in place while I got ready, shaped and painted my nails in a deep rose pink, made up my face, slipped into a sleeveless cherry red lace cocktail dress and matching heels, and was ready for my guests.

Joanne and Julie arrived within a few minutes of each other, and I settled them down for a pre-dinner Prosecco.

“ You are looking gorgeous tonight Jacquie, you didn’t say that this was to be a dress-up do, I feel a bid dowdy, is this a special occasion.” asked Joanne.

“ I have an announcement to make, well two announcements and a request actually. Firstly, as you know I have been spending a lot of time as Jacquie, and I have decided that this will now become full-time, Jack will fade into the background. Joanne, this means that I will need you to take a more active role in running the company, as a partner. I know you think that I will be accepted by our clients. however I am worried that there will be some of them that will not be comfortable with me becoming Jacquie, and we either have to drop them or offer them an alternative main contact, and that will be you. As long as you are happy to take on the extra responsibilities, we’ll agree terms and conditions later. Secondly, I have met with Tom Chapman, and not only is he happy to continue to work with me, but his company want me to carry out a major investigation for them, as Jacquie. Julie, where you come in is that for the next few days I need an intense period of readjustment to become completely natural again as Jacquie, can you manage to move in with me for a while and help me.”

“My bit is easy,” said Julie, “I will be delighted to help, I’m glad that you have finally made up your mind to commit, having dual-personalities was not doing you a lot of good mentally. we’ll start right away and I’ll stay the night and go home to collect some things tomorrow.”

“Two things I thought it was about time for you to sort out,” chipped in Joanne,”I’ve been hoping for you to recognise my efforts for the company and look forward to partnering you, and I’m delighted that you are finally going to live as a woman, and I’m sure that the girls in the office will be happy too. It’s an unusual situation, but I’m sure we can all cope and get through it.”

After a group hug, I went off to prepare the meal, leaving the girls to talk about me when i was out of the room. Dinner went really well, all talk of me and the business was banned at the table and we chatted away about all sorts of inconsequentialities like any other group of friends. After finishing off with coffee and cheese & biscuits in the living room, Joanne left for home to prepare to sort the office out for tomorrow, and Julie and I sat talking about the big step I was taking in my life before getting ready for bed.

“When are you going to tell the rest of the family, I know they live at the other ends of the country and we never see them, but we do phone each other and they always ask about you.”

“Keep it between us for the moment, just in case things go wrong, and if I decide to drop all this, I would rather that they didn’t know.”

I was up early the following morning clearing up after our meal, and preparing freezer meals with the left-overs, and Julie soon joined me for breakfast.

“You need to do this properly, particularly if you are going undercover in the next few days. As soon as we can get you booked in you need to get your hair restyled, it is long enough to get a short feminine bob cut, and I would suggest some highlights too, it will help a short style to look more feminine. Whilst your nails look good, I think you need to emphasise your femininity and you should get some acrylics stuck on to give them extra length, and the sooner the better because they will take some getting used to, picking things up, fastening buttons, even using your computer keyboard. I’ll see if I can get you booked in somewhere today. Get yourself dressed in some casual things, I’ll have another look in your wardrobe to check what you have now got and what more you will need and we’ll go shopping

Two hours later we got back home laden with bags, more underwear, a business suit, blouses and tops, a couple of skirts, and, of course, more shoes, and I went off for all my beauty treatments.

i called Joanne at the office to catch up on things, and she told me that she had informed the girls that I was going undercover again, and that I would be coming into work as Jacquie for the foreseeable future, but had not mentioned my decision to change lifestyle. All seemed to be under control so we agreed that I would leave it until the next day to call in.

Julie suggested that I needed to be out in public more, so we went for a walk down by the river and canal marina looking at all the boating activity, chatting to people and enjoying an afternoon out. Julie made sure that when we went into any shops or a cafeteria that I did all the talking or ordering, she was forcing me to improve my voice and intonation and made occasional comments about the way I expressed myself.

The next morning I went into the office, wearing a light casual top and plain A-line skirt, and just looked similar to the other girls. Nobody made any particular comments other than those they would make to anyone else, and I was just treated as one of the other girls in the office.

To be continued