“You never know where life is going to take you.” my mother always used to say, and now it had definitely taken me in a new direction.

My name is Jack Rowland and I run and own JR Investigations, a successful niche private detective agency based in Stratford-upon-Avon. Not for us the usual checking up on wayward marriage partners, or petty crime, we were specialists in investigating corporate fraud nationwide in chains of shops, hotels, professional practices and such like. I was not an office-based administrator but was often the lead investigator out in the field, backed up by my capable team of 20 full-time staff plus contract workers. Because a lot of our work involved placing temporary staff undercover in the target organisations, all of the team were female, as sending someone in as a sales assistant, admin assistant, or hotel domestic very rarely raised suspicion and these roles were usually seen as for females. These roles were considered too junior for senior staff, who were usually the ones carrying out dubious practices, to worry about.

For halloween we always had a themed fancy dress day in the office, when any of the staff not out in the field on investigation would all come to the office in costume, and this year the girls had decided on ‘Jolly Hockey Sticks St Trinian’s school uniform’. I didn’t know how to play this. As the boss would it be demeaning and undermining for me to dress as an overgrown schoolgirl and ruin what was a bit of a macho image, or would it be seen to be standoffish if I did not join in?

What the girls did not know is that, having been brought up with three older sisters I was often included in their dress-up games and, as my Mum did not object, this often meant going out with them to play or going shopping with Mum for clothes for my sisters. This left a deep impression on me, and although as I got older I did not dress as a girl anymore, I often thought about the times wearing my sisters’ clothes.

As is often the case, as the “last in the litter” I was a bit of a runt, I had stopped growing at 5’6” and never really bulked out. Even when I was at university and setting up my business and going through fitness phases at the gym, all the exercise did was make me lose weight and get fitter, I never seemed to build up my muscle mass.

Anyway, i decided that I would go along with the girls and join in as a schoolgirl for the day, but did not tell them as I wanted it to be a surprise. I asked my sister Julie, who was just a year older than me, if she would help me out, and when she had finished laughing she agreed, on condition that she could see any photographs of me with the other girls in the office.

Julie had recently separated from her husband who, although only married 4 years, had started playing the field again and she had thrown him out, so we had the house to ourselves the night before halloween to get me ready.

“ Right, we have two options, either we send you in as obviously a bloke in a dress, unshaven, bare hairy legs, with garish makeup, or we do a proper job and make you look convincingly female, which do you want.”

“The girls always make a big effort with their costumes, bearing in mind that they often have to dress down for their undercover roles, and I think it would be a bit of an insult if I turned up as a caricature, I think it would be better if we did the job properly.”

“ Let’s get started then, we have a lot to do, go up and have a shower and shampoo, and use my scented body-scrub, and shave your legs, arms, chest and pits. I will check you out when you are finished and clean up any bits you have missed. Meanwhile I’ll dig out a few things for you to wear.”

I came out of the bathroom in a towelling robe feeling all tender where I had shaved my body parts, they were not used to being attacked by a razor, Julie sympathised and passed me a tub of moisturiser to take away the tingling, and while I was rubbing it in she showed me my costume for tomorrow.

“I have a costume from a fancy dress party i went to a few years ago that should fit you, and you can borrow one of my wigs, your hair is far too short to do anything with. I’ve also dug out some underwear but we’ll have to sort something out to fill your bra and give you breasts, have you any ideas?”

I didn’t want to admit it to Julie but I occasionally visited transgender web sites and had seen that an easy way, but not perfect, was to use nylon stockings filled with birdseed or rice, apparently they were firm enough to stay in shape and heavy enough to have a realistic jiggle when walking, and told Julie that I had read somewhere that it might work. She came back a few minutes later with a bra and two stockings filled with rice, and made me try them on. They did give a realistic shape and felt heavy enough, but she was not too happy.

“They are ok but I have an idea to make them even better, leave it with me until the morning. we’ll need you up bright and early, we have things to do, get ready for bed and have a good sleep if you can get the thoughts of facing the world tomorrow as a schoolgirl look-alike out of your mind. I have left out one of my pyjama sets on the bed, I assume you did not bring any with you.”

On the bed I found a camisole top and shorts pyjama set, pink with little red hearts all over them, i think Julie was having a laugh at me, but they looked comfortable and they fit me well.

At 7 o’clock, Julie woke me up and I went down for breakfast still wearing the pyjamas.

“Hey, they suit you, you don’t have bad legs now that you have shaved them, you can keep them if you want.”

We only had a light breakfast, muesli followed by a slice of toast and coffee, and Julie started to work on me. She brushed back my hair and pulled on a tight skull cap as a base for the wig, cleaned up my eyebrows and checked that I was still hairless and didn’t need to shave again, and started my makeup.

“Follow what I am doing, you will probably want to touch up bits and pieces throughout the day, and when I am finished I will sort out a make-up bag for you. On top of the basic foundation, she added a little blusher to my cheeks and with an eyebrow pencil added freckles across my nose and cheeks. She emphasised my eyes with two coats of mascara and went quite heavy with the eyeliner, and finished off with a rose-pink lipstick, and matching fingernail polish. She fitted a shoulder-length auburn wig on me, tied at the back in bunches with little butterfly hair bands and I was ready to get dressed

Underwear was a black bra, knickers and suspender belt set, with an extra pair of very tight knickers to keep my pride and joy in place.

“I’ve added to your suggestion for the breasts by soaking the rice in jelly (jell-o) to bind it all together and it has set quite well and wobbles about.” she said as she put them into the bra cups. They fitted quite well and spilled out over the top of the bra, pushing my chest flab into a bit of a shadow cleavage, and as the stockings were flesh coloured they blended in fairly well and would be realistic under a blouse.

The usual St Trinian’s image always included black tights and suspenders rather than tights, and I struggled with the little button clasps, so Julie did them up for me.

The outfit was finished off by a white blouse, unbuttoned to the cleavage, and a short flared black skirt just showing the suspenders and stocking tops. I managed to squeeze into a pair of Julie’s older shoes that had slackened off a bit, with a 2” wedge heel that weren’t too awkward to walk in.

“Ok you need a coat to wear to get to the office and there’s a shoulder bag for you to put your keys, wallet, make up and bits and pieces in and you’re ready to go, I’ll give you a lift in, just in case you get stopped, if you drove yourself I’m sure the police would enjoy making fun of you.”

Thank you so much Julie, I don’t know how i would have managed without you, but please let’s keep this to ourselves, don’t even tell your sisters, you know what gossips they are.

I walked into the office, terrified of the reaction i would get, but once the girls realised who I was and got over the shock, they were amazing. They asked me where I had got my costume, and who had done my makeup and really complimented me on how I looked and blended in with them, and started calling me Jacquie, after all I didn’t look like a Jack today. One of them even gave my breasts a little squeeze see how genuine they felt as well as looked, and I jokingly threatened to report her for sexual harassment. The girls had all joined in the themed dressing-up and all looked very much the same as me, but some of them had tarted themselves up a bit over the top and quite sexily.

Other than the way we were all dressed, the day was fairly routine, as well as field-work investigations there were a lot of background searches carried out in the office and we were kept occupied with those.

At the end of the day, Joanne, my longest serving staff member and number 2, came in to say that she and some of the girls were going down to the local bar for an after-work drink, and, unusually, invited me to join them, normally they didn’t ask as I was seen as the boss and a man and it would spoil their girly chats. However, having worked with them in a skirt and make-up all day, my image had changed and I was seen as one of the girls. We all spent a few minutes, adjusting our costumes, mainly hitching up the skirts a couple of inches, and tidying up our make-up, me included, and headed out.

We caused a stir when we walked into the bar, a dozen or so sexy schoolgirls, and a few jaws dropped at the sight. Word must have got around by jungle telegraph as the bar soon filled up and we were the centre of attention, particularly as sitting in very short skirts, our stocking tops and suspenders were really showing, and the girls were outrageously flirting. That night I realised the effort girls make to look attractive, and how effective it can be, we didn’t have to buy one more drink while we were there.

Eventually it was time to make tracks, and with lots of hugs and cheek kisses we all said goodnight, and I got into a taxi for home. The taxi driver was unusually chatty, commenting on the way I, and the colleagues he had seen, were dressed and that it must be fun working with such a lively group of girls, and that as he worked alone he never had the chance to socialise. I was beginning to get a bit worried that he was chatting me up, but he soon had me safely delivered to my door, and with a good tip and a last look at my legs and skirt, he drove off to his next call.

When I went in, i noticed a parcel had been put through the letter box, Julie has packaged up and dropped off the pyjama set I had worn last night.

“Hi Julie, I got the parcel you left, why did you do that.”

“I told you this morning that the sleep-set suited you and that you could keep it, I never wear it anyway. If you want you can also keep all the rest of the stuff, it’s all spare and it means you don’t have to worry about getting it straight back to me. I know that you always enjoyed dressing up with us when we kids, and last night and this morning you too easily agreed to let me do anything I wanted. I think you might find a use for them, don’t you?”

“ I don’t know what to say, you are right, I did enjoy our games, but haven’t worn girls’ clothes for years until yesterday, if you are sure it’s ok I will keep it all for the moment. Thanks once again for your help today Sis.”

“That’s ok Sis, goodnight and pleasant dreams.”

I took off the outfit and on impulse put on the pyjama set, cleaned off the makeup, and carefully put the wig on an upturned bowl to keep its shape.. I slept well that night with, as Julie had suggested, pleasant dreams centred around attending St Trinian’s and lots of escapades with the other girls.

I dressed in my normal casual clothes and headed into the office. The “Good morning” welcomes were a lot less formal and polite than usual, in fact they were a lot friendlier and more pleasant.

There was a much more easy-going atmosphere in the office that morning, the team-bonding session down at the bar had obviously rubbed off on them all.

Mid-morning Joanne came in to my office, along with coffees and biscuits, for a chat about a couple of our projects. When we had finished you told me that the girls really appreciated the effort I had made yesterday in joining in with the fun and how they now felt much less wary of me as the boss, and if Jacquie ever wanted to make a reappearance, there would be no objections from anyone.

“Oh by the way, you cleaned off all traces of your makeup ok, but you forgot about your nails, the rose pink clashes with your jacket. Everybody noticed it straight away, so you may as well leave it on, or I can get get you some remover pads, but your sister did them so well it would be a shame not to finish today with them as they are.” i chose to clean them off before I forgot again.

The photos from yesterday that the girls had taken on their phones, appeared on my email later in the afternoon, and I was surprised at how difficult it was to pick me out from the others, it was mainly a process of elimination rather than easy recognition. I sent them on to Julie with a covering note “spot the odd one out.”. I left the photos as a screensaver sequence on my computer screen for the afternoon and every now-and-again had a quick look to remind me what I had done.

Just before we closed, one of our good clients, Tom Chapman, the security manager for a major retail clothing chain clients, called in to the office saying he had a problem he wanted to talk through with me. We were going through the usual pleasantries before getting down to business when he saw one of the images on my screen.

“It looks like someone’s had a good time recently, are those the girls in the office, I wish my staff were as attractive as that lot. I don’t see you anywhere, do not not mix with your staff?”

“ Actually, I am on the photos, see if you can spot me.” I said turning the screen so he could have a better look.”

He went through the images three times before giving up. I picked the best close up and zoomed in and turned the screen back to him.

“ I wouldn’t show this to anyone else but I trust you, we’ve worked together for years. The girls picked the theme and I was talked into joining in, please keep this to yourself.”

“Wow, you are quite a looker, I would never have picked you out in a month of Sundays. Actually this may help me in what I came to discuss. We have a problem in one of our stores, It has unusually high sales figures, but very low profitability, I’m sure that there is some sort of fiddle going on, but can’t put my finger on anything in particular.”

“Do you want me to send in one of my girls, as a new sales assistant or trainee manager, staff tend to gossip if they think anything unusual is going on, and we may be able to pick up some clues. It may be best to send someone in as a trainee manager as you are always rotating them around your shops to get experience before giving them a permanent position.”

“That sounds a good idea but, no disrespect to Joanne or any of your other staff, I think it needs someone a bit sharper and more experienced. I would like you to do it yourself.”

“I can do, but women tend to gossip more to other women that to men, are you sure I can’t use one of my more experienced girls.”

“You haven’t quite followed me, i have seen how you look in those photos and would like you to go in as a woman. do you think you can do it.”

“That’s a strange one, it’s one thing getting away with it at a fancy-dress do, but it will be much harder in a real-life day-to-day role. Let me have a think about it and I give you a call and come to see you in a few days.”
When Tom had left I called Joanne into the office, told her what he proposed and asked for her opinion.

“We’ve never been asked to do anything like that before, but they are good clients and pay well and on time. If you are prepared to do it, after seeing you yesterday, I think you might be able to get away with it. I’m disappointed that he does not think that any of us are capable of doing the job, but if we don’t give him what he wants, he’ll start looking elsewhere. If you feel like giving it a try, get your Julie to sort you out as an everyday woman and come in to the office to see what the girls think and get into the role, before you give him your decision.”

“Julie can I come round tonight there is something I need to talk to you about urgently, are you doing anything/”

“By all means, come round, I’m always glad of the company now that I am on my own again. By the way, I love the photos, it looks like you enjoyed yourself.”

I called round and told Julie everything that had happened today, including the girls seeing my fingernails and all the comments about the photos, and about Tom’s visit and his proposal.

“In a way I see it as a challenge, but I am so worried that it might go disastrously wrong. you know me better than anyone, do you think we could make this work.”

“You and I look a lot alike, when we were younger and you went out dressed as a girl, we were often mistaken for twins, I’m sure that looks-wise we could make it work. How did you get on yesterday in the office and down at the bar, did you fit in or did anyone pick you out from your speech and mannerisms as a bloke?”

“No, it went ok, I soon found that I was talking and expressing myself as just another one of the girls, and in the bar I was getting chatted up as much as any of the others.”

“We’ll give it a go, but you will have to be in the role for a few days to see if you are passable and comfortable. Go home and close everything up, get what you need and come and stay with me for a few days.”

When I got back we went through the same routine as the previous time, close shave, shower, moisturiser, nails painted, including toe nails this time, and sat down wearing my pyjama set, for a glass of wine and a chat.

“I don’t think that the wig is suitable for a few days, or even weeks, so I called my hairdresser, she should be here in a few minutes and she’ll see what she can do with your hair, I think it may be long enough to fit extensions. Don’t worry, I’ve known her for years, she can be very discreet, hairdressers hear all sorts of secrets from their clients, and I gave her a rough idea that you are doing this for an investigation.”

As if on cue, the doorbell rang and Julie introduced me to her friend and hairdresser, Carol, who had a good look around me, lifted sections of my hair, and played about with her brushes and comb, and finally agreed with Julie that extensions would work, and that if I went around first thing in the morning she would be able to deal with me as she had had a cancellation. I sent a quick text message to Joanne to say that I would not be in the office tomorrow and would speak to her later in the day.

At 7:30 the next morning, I was in the chair in Carol’s salon, dressed in one of Julie’s jogging suits covered by a salon smock, she had a lot of work to do and wanted to get it all well under way before other customers started to arrive. Before she started on my hair she wanted to get me reasonably presentable as female. She trimmed and shaped my eyebrows, fitted, shaped and painted acrylic nails on my fingers, and covered me in a facial pack before starting on the hair.

For what seemed like the rest of the morning she wove and glued long extensions onto my natural hair, coloured it all a light auburn to be a reasonable match to my natural colouring, and cut, shaped, rolled and set it all to a just-on-the shoulders wave. I was staggered at the big bill for Carol’s work but was very happy with the result. It was all charged to the company anyway, and if everything worked out, the cost would be passed on to Tom Chapman’s account. I got a taxi back to Julie’s and let myself in, as she had an appointment with her divorce lawyer. She had left out a skirt and top for me to put on, with instructions to get dressed, put on some makeup and begin to get used to it all, I already had on the bra, along with my falsies, and panties, under the jogging suit.

When I was dressed I just wandered around the house getting used to the feel of it all, especially the constant movement of my breasts and the sway of the hips resulting from wearing 3” stiletto heels that she had left out for me. I answered a ring of the doorbell to find a courier delivery driver with a parcel for Julie from Amazon, intrigued I signed for it, she hadn’t mentioned expecting a delivery. There’d been no recognition or reaction from the courier, these guys don’t take much notice, they are always in a hurry to meet their tight schedules.

When Julie got back I handed her the parcel but she gave it straight back to me.

“It’s for you actually I ordered something for you last night on next-day-delivery that I think you will need, don’t worry, I charged it to your company credit card. You are looking fantastic, Joanne has done a really good job, and your makeup is pretty good, now we look even more like twins”

I opened the boxing and, after a few seconds wondering, I realised that she had ordered a set of breast forms for me.

“ I got a matching size to mine, you are not much bigger built than I am, so they should be an appropriate fit and they should be a lot more realistic than the home-made ones, they were ok for the fancy dress, but you need something better if you are going to pass scrutiny for a few days or even weeks. Take off your top and bra and lie down and we’ll see how they fit.”

I hadn’t realised exactly what she was doing until I found the breast forms glued to my chest, and she was tidying up around the edges.”Just lie still for a few minutes, until the adhesive fully sets and we can see how they hang.”

When I stood up it was strange sensation, rather than just a weight from the bra onto my shoulders from the home-made falsies, these actually pulled at the skin of my upper chest and felt like an integral part of my body.

“They look fine, and will look and feel even better when they get a bit of support uplift, put your bra back on and you will see what I mean.”

She was right, the bra pushed up the breasts which creased at the edges to help hide the joins. i put my top back on again and was surprised at how it clung to the contours of the breasts looking totally natural

“They should be fine now for as long as you need them. I also got some adhesive solvent to remove them when this is all over, but you have to keep them for now to get used to their feel and movement, and hold your shoulders back or you swinging arms will brush against them. We’ll see how the afternoon goes and if I think you will do, you can give Joanne a ring to get her to come round and give her opinion.”

The rest of the afternoon was a barrage of sit, not like that, keep your knees together and your back straight; stand up again, not like that, rise slowly and balance your body without using your hands as support; walk over here, not like that, put one foot in front of the other; tell me what you are doing, not like that, pitch your voice up a bit and be more expressive, and use your hands and eyes more when you are talking; and lots of other minor faults. I thought that Julie was giving up on me, then she told me it was time to get Joanne to come over.

I answered the door to Joanne and she gave me a welcome kiss on the cheek. “ Hi Julie I haven’t seen you for ages, thank you for helping out to get Jack to come over to our team, where are you hiding him, let me have a look.”

Giggling, Julie came out into the hall. “ I’m not sure if I should be pleased or worried that you mistook Jack for me, but i assume that means that you think Jacquie looks ok”

“I don’t believe it, is that really you Jack, you two look so alike, not identical but definitely like sisters. I think you should come into the office tomorrow and see how you act and behave in with a group of women before we agree anything with Tom, but the signs are definitely looking good.”

“Right, next lesson,.” said Julie, “grab you bag and put on a coat from the hall stand, the three of us are going out for a meal at the inn just down the road.”

“ Good evening Ladies, a table for three is it? There’s a table with a nice view of the river over there by the window, let me take your coats and you can go and sit down, I’ll bring you over the menus and take your drinks order” said the pleasant and polite waitress.

The table was in a great location, we could see lots of activity in the marina and on the river and all the adjacent tables were free so we could chat in private, which was just as well, as the lessons continued.throughout the meal.

“Don’t put your elbows on the table, just rest your forearms; don’t order your normal steak and chips, the Dover sole with boiled potatoes and green beans is better for you; eat smaller portions and chew your food more slowly; the desert portions are too big let’s order one between us; sip your wine more slowly don’t gulp it down like that.” I can honestly say that I could not remember enjoying a meal less.

Before saying goodnight back at Julie’s, Joanne said to give her an hour in the morning for her to tell the girls what was happening, before I turned up at the office. Julie and I cleaned off our makeup and got ready for bed, but instead of my pyjama set she had left out a full length strappy night-dress for me ’to stay in character’. “You might find it more comfortable to sleep on your back until you get used to the breasts” was her final lesson of the day.

With my whole body quivering with anticipation, I went through the door into the office wearing a smart business outfit of a navy knee-length pencil skirt and matching waterfall jacket with a pale turquoise blouse and black 3” stilettos. Apart from the normal “good morning”. there were no comments as I walked through to my office until there was a sudden cheer and shouts of “go get them girl.” and I was surrounded and pelted with questions about how I felt about the proposed project and about joining the ‘fair sex’, but soon routine kicked in and we all just got on with our work.

Late morning Joanne came in to review the comments she had received from the girls, she had told them that rather than saying anything individually, any comments about the way I was behaving should be channelled through her.

“Generally you are doing very well, the girls were astonished when you first walked in and didn’t recognise you at all, if I hadn’t forewarned them they would have stopped you and asked who you had come to see. They have noticed a few minor things but a lot of it is nit-picking. Be more careful with your voice and how you express yourself; look directly at people when you are talking to them, maintain eye contact; don’t slouch at your desk, sit up straight; and the one they have all commented on, get your ears pierced, no woman nowadays would not have had them done. At first there was a lot of chatter about your choice of clothes, hair and make-up and how totally believable you are, but it didn’t take long before they just accepted you as part of the office scene and went about their work. Put on your coat and grab your bag, we’ll go to get your ears pierced and buy some studs and other accessories, then go for lunch, everyone agreed that you are perfectly acceptable to go out in public.”

I insisted on sticking to only one piercing in each lobe, selected some sapphire studs to match my outfit, small gold hoops and some sleeper studs. I added a couple of chain pendant necklaces, we finished our shopping and went into the local bistro for a light salmon salad lunch and a glass of wine.

“Just relax Jacquie and act normal, do not be so tense, no one is looking at you except with admiring glances, get used to being an attractive woman.”

“It’s ok for you to say that, you have had your whole life to learn how to conduct yourself, for me this is like learning to drive, I have to concentrate all the time and worry about what to do next, and question whether I am doing things right, nothing is done just automatically.”

“Honestly you are doing fine. Can you try to soften your voice a little, you don’t have to go high-pitched or falsetto, and try a softer accent, maybe Irish or Highland Scots, not only will it sound pleasanter but it will help with your disguise.”

The rest of the afternoon was very much more of the same, although I now was speaking in my grandmother’s soft Argyll accent, and Joanne was right, it did sound better without being false.

“Ok Jacquie, I think you are almost there, I’ll make an appointment for me to see Tom in two days time, telling him that Jack has been called out to court as a witness on one of our other cases, and you can come with me as a notetaker and second opinion during discussions, do you think that you are ready for this.”

Two days later, after much more coaching and familiarisation, Joanne and Jacquie turned up for their appointment with Tom at his office in Warwick. I explained who we were and the receptionist told us to take a seat and he would be down in a few minutes. Tom greeted Joanne with a quick peck on the cheek, and gave just a token handshake to me as he had never met me as Jacquie, and led us up to his office, offered us a choice of drinks and asked his secretary to bring in some coffee and biscuits for us

“I’m not too pleased that Jack isn’t here, I thought I was going to be dealing with him on this.”

“ You will be dealing with him for the actual investigation, but I am just here to sort out the business side, agree fees etc. Jacquie would you like to give Tom a run-down of our proposal.”

Speaking in a soft Hebridean lilt, I ran through our proposed contract, and we agreed charges, expenses and timescales, which Tom questioned but finally agreed to.

“That seems to be all Ladies, please get Jack to give me a call to talk through the details of the investigation.”

“ No need for that Tom,” I said reverting to my normal voice, “I’m already here. I think I’ve passed my test on presenting myself as a woman, you seemed convinced.”

“ Never, I don’t believe it, you had me completely taken in, even my secretary and our receptionist did not notice anything out of the ordinary and they normally size up female visitors in a few seconds and give me the lowdown before I meet them. I definitely think that this is going to work. To save the bother of anyone questioning all your expenses I will get you a pre-loaded store shopping credit card, presumably you will need several changes of clothes and it will be easier if you buy from us as all the purchases will be written off to our company account at wholesale prices. Get yourself sorted out for a stay for at least two weeks, come and see me on Monday, I’ll get HR to introduce you to the regional manager who will take you in to the store. He and the store staff will just know you as Jacquie, one of our trainee managers.”

On leaving Tom gave both Joanne and I a warm two-handed handshake and a peck on the cheek as he said goodbye. “Sorry Jack, force of habit with attractive ladies, and you have now got me thinking of you as Jacquie.”

“Come on Jacquie, while are in town let’s hit the shopping centre and introduce you to girl-shopping, you have the credit card, let’s see what we can get with it. If you are planning to stay for a couple of weeks at least, you will need quite a lot of clothes and accessories. It has been good of Julie to let you borrow some of her stuff, but it’s not fair on her, you need all your own stuff.”

The basics were quick and easy, bras, knickers, tights, jewellery, toiletries, and accessories, but outer clothes, dresses, skirts, tops, coats and shoes seemed to take forever, there was so much choice, and for every item we bought I must have tried on three or four. Joanne was really enjoying herself, shopping with someone else’s money was a new experience and she was making the most of it. I ended the day with a coat, two jackets, 3 day dresses, one LBD for evenings, four skirts and 6 blouses/shirts/tops. I was well past my shopping attention threshold, when Joanne suggested to my amazement “That will do for now, we’ll see how it goes and what else you need.”

When we got back to Julie’s she insisted on me putting away all the underwear and accessories and modelling the main clothes for her, she was very impressed with Joanne’s taste and eye for detail and there was nothing she could suggest that wasn’t right or didn’t suit me.

“ It’s so good that you have now got a wardrobe of your own, it will be nice to get my clothes back, but obviously you can just keep the underwear and the couple of tops you have used.”

The rest of the week I was in the office as Jacquie continuing my feminisation training and clearing my desk and inbox of other ongoing projects, which were passed on to Joanne to deal with. On Friday, my last day before going undercover, we went for an after-dinner drink, with a few of the younger staff who were having a night on the town, in the same bar where we had been St Trinian’s girls. We were chatting away talking about work, life in general, relationships, celebrities, and I realised I was drinking a lot more than I normally would, wine is so easy to drink and does not fill you up like beer does, and along with the others i was getting quite excitable and noisy. When we had finished that round of drinks, Joanne decided it was time for me and her to leave and let the others make a night of it. Outside the fresh air hit me and I went quite light-headed, but Joanne bundled me into a taxi and took me back to Julie’s.

“That was your final test, we deliberately got you half-drunk, and although you got quite excited and loud, you behaved like any other woman after a few drinks and didn’t let your male side come out at all. Congratulations, welcome to the sisterhood, enjoy your day in the shop on Monday, and keep in touch. Don’t phone Tom with any findings, call me first and I will pass on any messages, it will be less suspicious if anyone overhears you talking to a friend, rather than to the Head of Security.”

I was now as ready as I ever would be for my role as Jacquie, trainee store manager.

To be continued