Since leaving university my life had come to a stall. Despite graduating with a 1st in Business studies and Marketing I had not been able to find a suitable job anywhere. Due to the economic downturn And the global effects of the virus people were being reluctant to leave decent positions and companies were being reluctant to take on additional staff in anticipation of a future upturn.

I was passing time until something came up by working in the shop owned, managed and operated by my mum, Newmans’s Delicatessen. To call it a deli was actually a bit of hopeful exaggeration, it was more of a sandwich bar with a side offering of a few basic cakes, scones, and whatever sandwich filling ingredients we were using, sliced meats, cheeses, mayonnaises and such like. My mum, Kathy, ran the shop and did most of the baking and making up the salad dressings, assisted by Jennie, Carol and Jean were front of house, making up sandwiches to customers’ orders and generally keeping shop, and I was the gopher/dogsbody. Anything which involved a bit of physical effort fell to me, mixing and kneading the bread dough, making the pastry and cake mix, lifting and fetching and carrying the supplies.

It was not what I had expected to be doing when I had been working through university, but it passed the time, gave me a wage, and it was a pleasant working atmosphere, I got on well with Mum and the girls, and despite being the only male amongst them they involved me in the chat and to an extent looked upon me as another one of them and made no allowances for me even when they were discussing more intimate female subjects. The main drawback to my role was that I had to be the first one into the shop in the mornings to get the bread made and the pastry mixed and rolled out before Mum arrived to carry out the clever stuff turning the basic ingredients into something mouth watering and attractive.

As I was the first to arrive, I was also the first to leave and usually when I got home I prepared the evening meal for when Mum got back later after closing up and doing the daily accounts ledger. I was not a fancy cook, it was mainly good wholesome stuff, cottage pie, fish pie, lasagne, bolognese, or curry and rice, and suchlike, although that was using jars of ready-made sauces, I was not into starting with the basic spice ingredients. I actually found it to be a rewarding and relaxing way to unwind at the end of the working day. As there was only Mum and I at home, my sisters had now left to live their own lives and my father had disappeared when I was very young, I felt it only fair to do my share of the chores around the house.

“Ok Jay, that’s you finished, get yourself off home and I’ll be back in a couple of hours after I’m finished here.” Mum smiled as she almost pushed me out of the door.

“See you later Mum, bye, Carol, bye Jean, bye Jenny, see you all tomorrow.” I called over to the others and gave them a finger wave as I left.

When I got home there was a pile of mail lying on the floor under the letterbox. Most of it was the normal junk, insurance, offers, household and fashion catalogues, flyers for restaurants and local shops, nothing exciting needing attention, so I decided to get changed out of my work clothes into my casual shorts and t-shirt and check out my email.

Just like the post, most of it was advertising junk, but amongst it all, to my surprise was a mail from a marketing company telling me that I had won a prize in an online competition run by one of the commercial tv stations. A lot of the tv daytime shows ran phone-in competitions to win holidays, weekend breaks, cars, money or even holiday homes. As I was out working most days I missed out on most of these, but regularly sent in an entry sponsored by one of the cookery shows showing on Sunday mornings when I had time to watch as the shop was closed.

“Congratulations, we are delighted to tell you that you have won our prize from last week, a residential 2-week course at the famous “ Burg von Gebäck “ hotel, which along with its luxury facilities and gourmet restaurant is renowned for its extensive and delicious selections of Austrian and German cakes and pastries. You will be instructed by, and work alongside, the celebrity pâtissier Hugo Möser, and when not working the full facilities of the hotel will be available for you to enjoy. Please call us to confirm that you will be taking up this prize and arrange details.

Kind regards
Marsha Standing
(Head of Promotions)”

I was so excited, I had never won a competition for anything in my whole life, the thought of a 2-week stay, all-expenses paid, in a luxury hotel was something to enjoy, and the cookery school aspect was something that may be useful to pass on to Mum.

“H..h..hello, can I speak to M..m..Marsha S..s..Standing please.” I stuttered a bit as I often did when I got nervous or excited, along with my voice going up a pitch, it only rarely bothered me, but seemed to be affecting me now.

“ Hi, I’m Marsha, how can I help?”

“Hi, I’m Jay N..n..Newman, I’ve had a m..mail from you saying that I have w..w..won the competition for a cookery course at B..Burg von Gebäck.”

“ Ok, let me just take your full details and we will send you a full information pack on directions, when to arrive and what you will be expected to bring with you. There will be eight of you on the course, another one of our contestants, Kelly Masters, and six others who will be paying for the course themselves. I hope you enjoy your time there and find the course enjoyable and useful.”

“ T..t..thank you so much M..m..Marsha, I am really looking forward to it. Bye.”

When Mum got back home. I hardly gave her time to get in and take off her coat before blurting out the news.

“I’ve w..w..won a cookery course at B..b..Burg von Gebäck working with a famous p..p..pâtissier, in a month’s time, can you work without me for a couple of weeks? I think that the change will do me good”

“ Calm down Jay, your stutter always gets bad when you get nervous, take some deep breaths let me get changed, and then you can tell me all about it over dinner.”

The next few weeks flew by as I eagerly anticipated my time on the course. I woke up early on Sunday morning to travel down to the hotel for the course starting on Monday, finished packing a few changes of everyday clothes, the working chefs uniforms were to be provided by the hotel, had a shower and gave my hair a good shampoo, dried off, dressed and was soon on my way. I had decided to go down by train as it seemed a waste of time taking Mum’s car and having it sit in the car park for a fortnight, leaving her to get into work by bus.

I arrived at Cheltenham station and took a taxi to get me the few miles out to the hotel. We had got most of the way there when a car came too fast and wide around a bend in the road causing my driver to swerve, go off the road and end up in a ditch.

“ Sorry about that, the idiot hasn’t even stopped to see how we are, it’s a pity I didn’t get his reg number to report it. This is going to take some time for me to get this sorted out, your hotel is only just over a mile down the road, it will be quicker if you just walk there, you can’t miss it. I would normally call another cab for you but my radio has been damaged when we crashed and mobile phones don’t work very well out here. Can I have your name and contact details, just in case we find out who the other driver was and I need you as a witness, of if the police or my insurers need to speak to you.”

After giving him my details I set off down the road, which as it turned out was a huge mistake, I was about halfway there when the heavens opened and i was caught in a torrential rainstorm. I was absolutely soaked, cold and fed up, and getting really miserable when a car pulled up beside me and opened the door.”

“Get in, you will catch your death out there, I am only going just down the road to the hotel but at least we can get you out of this rain.” I was delighted that someone had the decency to help me out and even more pleased to see that it was a pleasant attractive girl, about my own age.

“T..t..hank you so much, that will be ideal, that is where I am going too. I’m Jay N..n..Newman and I am going there to do a c..c..cookery training course.”

“That’s a coincidence me too, Kelly Masters, it looks like we will be seeing a lot of each other over the next few days, pleased to meet you Jayne.”

“It’s Jay, not Jayne, this is always happening, that’s what you get when you are lumbered with an unusual name.

“Sorry about that, it’s just the way you said your name and stuttered it sounded like you said Jayne, and your voice is quite high for a man, I just assumed that you were a girl.”

“Never mind, I’m just grateful for the lift to the hotel. In a way I’m used to it, I’m quite slightly built and with my wavy collar-length hair, I do occasionally get called Miss or Jayne, particularly when my voice pitches up when I get stressed.”

“Ok Jay, we have arrived , let’s get booked in and you can get dried off and changed into something clean.

“Hello, I’m Kelly Masters, this is Jay Newman, we are here for the cookery course.” Kelly
dealt with the receptionist while I just stood there, with water dripping onto the floor from my sodden clothes and my bedraggled hair.

“Good evening, Miss Masters and Miss Newman, I’m Helen, the duty manager. I hope you don’t mind but we are full this weekend and have had to put you both into one of our twin rooms, I hope you are happy sharing.

“I….” I started to reply and correct her before we were interrupted by two guests having a big row across the reception lobby.

“Do you mind waiting a minute, while I sort that out, sorry about this.”

“Jay, it looks like they have made a mistake with your name like I did and they have you down as Jayne. Look, she said they have no more rooms available let’s just get the keys and get you into our room and dried, we can sort this out later. I don’t mind sharing if you don’t, and if you promise to behave yourself.”

“Ok Kelly let’s just get the key and get away from here. I grew up with two older sisters and often when we had visitors I ended up sharing a room with one of them, so seeing girls getting changed or in their nighties is nothing new for me.”

The receptionist was soon back, we got our key and went up to our room. I opened my holdall and was shocked to see that the rain had soaked through the canvas and everything was too wet to wear, made even worse by my bottle of mouthwash having broken in the crash and stained everything splashes of blue, I almost burst into tears, what had promised to be an exciting time was turning into a disaster.

Kelly saw me with my head in my hands and came over to see what the matter was.

“What am I going to do Kelly, all this stuff is as wet as the clothes I have on and most of it is stained and ruined anyway or at least needs a good wash.”

“Just a suggestion, but while you go and get cleaned up and dried off, I will see if I have anything you can wear, we are almost the same size and I am sure that we can sort something out.

Ten minutes later after a hot shower I felt a lot better and relaxed, wrapped a towel around my waist and went back out to the bedroom.

“ There are some plain panties, they are just cotton and not too girly and I found some jeans that should fit you along with a couple of fairly neutral tunic tops and a pair of the nearest to flats I have, they only have a small heel. They should do to at least get you decent while we decide what to do.”

“Are you joking, I can’t wear girls clothes, is that what you think of me?”

“Please yourself, you can sit there for the rest of the day in just that towel if you prefer but don’t expect me to run around after you getting food and drink and sorting out your laundry.”

“Sorry Kelly, you have got a point, I have to wear something and what you have picked out isn’t too feminine, I’ll give it a go and hope that I do not look too silly.” She was right the clothes were a reasonable fit although everything fitted a bit more snugly than normal.”

“Are you sure you don’t mind Kelly, someone else, particularly a boy, wearing your clothes?”

“You have sisters Jay, you must know that girls borrow each others clothes all the time, and I am sure that when you were younger and your sisters were playing dress-up games that they talked you into joining in. It wouldn’t be surprise me if they even got you into dresses and skirts, I know that my sister and I did with our brother.”

“You’re right, unfortunately, Sarah and Chloe did use me a bit as their dress-up Barbie doll, but that was a long time ago and I have grown up a lot since then.”

“Let’s go down to reception and see whether they have laundry facilities we can use.”

“You must be joking, I can’t go down like this, I feel silly. I know that the clothes are not too fancy, but they are obviously girls’ styles, what will they think of me.”

“They already think that you are a girl anyway Jay, you are booked in here as Jayne don’t forget, and you don’t look silly, the clothes actually look quite good on you. Let me brush out your hair, apply a bit of lippy and mascara and nobody will be able to tell.Just treat it as a bit of dress up fun.”

“Do I have a choice,? I do need to get my stuff washed and dried, I suppose that I will have to give it a try.”

Ten minutes later, Kelly had restyled my hair, put in some side combs, added a little mascara and lipstick and I was ready to go.

“Hold on a minute Jay, have a look in the mirror and tell me what is wrong with you.”

“It looks ok to me, you have done a good job.”

“Let me stand next to you and look again, what is the really obvious difference between us?”

“I give up!”

“Boobs, you blind idiot, you are totally flat-chested, take off your top, carefully so as not to spoil your hair and makeup, and I’ll find you a bra and something to pad it out a bit with.”

“This has gone far enough Kelly, let’s just call room service and get them to deal with the laundry, if I suddenly develop breasts and get seen by people, that is it, no turning back, I will have to stay female for the whole of my stay here or look absolutely stupid when people see me as a boy again.”

“And what would be wrong with living as a girl for two weeks Jay? As far as I’m aware all the others on the course are women, so rather than sticking out like a sore thumb, dressing and acting as a woman will help you blend in better and be part of the group. the experience might do you good, seeing how the other half lives. Besides, if the hotel were aware that you are not really Jayne, I’m sure that they would not be too happy about us sharing a room together, health&safety and protecting women and all that sort of stuff, then what would happen as they have no spare rooms.”

“I don’t know Kelly I feel stupid, what if anyone realises, what happens then?”

“Let me tell you, once you get boobs and with full makeup, you will have as good a figure and be more attractive than a lot of my girl friends, and your voice is quite convincing too, especially when you get angry and excited and raise the pitch. I am sure that you will have no trouble passing as a girl for the next two weeks.”

“Ok, you have almost talked me into it, let’s give it a try and see how it goes. It has stopped raining, as a test let’s go and have a look outside where anyone seeing me will not remember me.”

Luckily Kelly was not over-endowed herself and had some padded bras which she was happy to share with me, and suitably filled out I had to agree with her that I was quite passable as a girl.

Making our way through reception to the entrance Helen called us over. “I hope you settled in well girls and that everything is ok. You were absolutely soaked when you arrived Jayne. If there is anything you need to dry off, you can use the room service for your laundry, but if you prefer we have a launderette for guests in the basement that you are welcome to use.”

“ In for a penny, in for a pound.” I thought, deciding that I needed to see how convincing I was,

“Thank you for your help Helen, I think I will probably pop down there later and deal with it myself.”

“By the way, you and the other course members are booked into one of our private dining rooms for dinner tonight so that you can all get to know each other before you start tomorrow. I have to mention it, although I think that it is a bit stuffy, but the hotel prefers female guests to wear a dress or skirt in the restaurants, I hope that you have brought something suitable with you.”

Without giving me a chance to even think of replying, Kelly jumped in. “That’s no problem I was expecting something like that in a place of this quality, and Jayne too, we won’t let the side down.” and she dragged me off outside before I could say anything.

“This is getting worse and worse Kelly, what do we do now, you know that I have nothing to wear.”

“Spoken like a true girl Jayne, but don’t worry, I have a few dresses with me, us girls never travel light clothes-wise and are usually prepared for anything. When we get back upstairs you can try some on and see which suits you best.” I ignored the fact that she was now calling me Jayne, if she wanted to have a bit of fun at my expense, I would just let her.

Walking around the grounds, i realised what Kelly had meant when she had said to Helen about ‘a place of this quality’. There were formal gardens with medieval style box hedges enclosing flower beds, a terrace with lavender lining each of the small retaining walls, landscaped lawns and shrubbery, and even a large walled vegetable garden, which we later found out produced virtually all of the fresh produce used in the restaurants, The hotel building was basically Elizabethan and retained many of the original features, subtly blended with bright and airy modern interior fit-out and well deserved its 5-star rating. When we had arrived we were glad just to get out of the rain and did not have time to take in the quality of the Manor, but now were a bit in awe of our home for the next fortnight.

Back in the room I salvaged what I thought was worthwhile from my suitcase and stuffed it all into a laundry bag, sorted which of my toiletries were still usable, and put everything else into a bin bag, and was about to take it all downstairs to clean it or get rid if it when Kelly called me back.

“I’ve had an idea, it’s not too late Jayne, the shops in Cheltenham will still be open, let’s call for a taxi and to do a bit of shopping for you, we need to get you some stuff of your own. Are you ok for money?”

“As long as we don’t go too mad, my credit card should be able to cope, but don’t forget, this is just for a fortnight so we don’t need lots and lots.”

We called out a taxi and on the way into town I noticed that the one I had arrived in was still in the ditch, it was obviously not going to be a quick job to sort it out.

“What do think you need then Jayne?”

I had got used to being called Jayne by now and didn’t even think about correcting her, I had to get it into my head that for the time being that is who I was and who everybody would see and respond to.

“Well, Helen mentioned wearing a dress or skirt, so I should get one of each, a pair of trousers or jeans, a pair of shoes, and maybe a coat, if I can find one that’s not too expensive.”

“You have to think of yourself as a girl now, you need to at least double of all those things, and add a few tops, your own underwear, tights, get your own makeup and toiletries, you can’t keep using mine, and of course a couple of handbags. How does that sound?”

“It sounds very expensive, is it all really necessary.?”

“It’s not like boys wearing the same trousers and shoes everyday, maybe changing their shirt occasionally, there is a lot more attention to detail required for us girls, even casual dress needs to be coordinated.”

Kelly was in her element, really enjoying herself, dragging me around the shops trying on dresses and skirts, insisting that I came out of the changing rooms to check the fit in the mirrors out in the shop floor areas. At first when she had me rummaging through the underwear racks with her I was so embarrassed, particularly when she was passing over panties and bras for my opinion. I was quick to pass them back with a grunt of approval, but she wasn’t going to let me get away so easily and kept asking what I thought of the material or the style or the cut. I learned more about women’s underwear and which was best for what occasion in a quarter of an hour that I had in twenty years of growing up with my sisters, who had generally kept me well away from such things.

I must have tried on at least a dozen pairs of shoes before we found three pairs that Kelly thought suitable and I thought comfortable. although she kept telling me that women’s shoes and comfortable did not belong in the same sentence.

“Now for the fun bit. As well as the normal moisturiser and foundation you need some concealer. You have got a very light beard and your skin is quite soft but it is definitely not girl quality, you need a bit of help there. We need to top it all off with a shadow and blusher pallet, some mascara, eyeliner and pencil, a selection of lipsticks and that should do for now.”

“Are we done yet, I’m tired out and my credit card is looking a bit sick too ?

“Just a couple of handbags and a few bits and pieces and that is it all done. You are supposed to be enjoying this, your first girly shopping experience. Let’s just pop in this little shop for a couple of finishing touches.”

The finishing touches turned out to be getting my ears pierced and fitted with little pearl sleepers, along with a couple of more dressy sets and a heart locket and chain.

I was glad to get a taxi back to the hotel and to the safety and calm of our room, laden down with more bags than I had ever carried in my life, and just flopped on the bed for a rest.

“ What do you think you are doing Jayne, we have to get ready for dinner and meeting the other women.”

“ That’s not for another two hours yet, we have loads of time.”

“ That’s what you think, as well as giving me time to sort myself out, we have to get you ready, do your hair, nails and makeup, and before we start all that you need to have a close shave, including your legs, arms ,chest, and armpits, you really have to look the part, even more so than those of us who are lucky enough to be natural girls. Have you never noticed how long it took your sisters to get ready to go out for the night, well now you are going to begin to realise why, get in the bathroom and come out when you are clean and hairless.”

“Let’s have a look at you then. H’mm, you’ll do, but you can’t just sit there like that in next to nothing, To get you in the mood, put on a clean set of your new panties and bra, and give me mine back, and put on one of your skirts just for now so you can get used to wearing one. Have you ever put on nail polish?”

“ My sisters have put some on me before when we have been dressing up for Halloween and things like that.”

“ Good you have got some idea then. Trim your toe nails and give them a coat of polish while I have my shower and then I will have a go at your fingernails. I don’t trust you to make a decent job of them, but your toes should be ok.”

“ Why bother with the toes, my shoes will cover them, nobody will see them?”

“ Men!!, why am I bothering with you? It is all part of the package of getting ready, your toenails are as much part of how you are dressed as your fingers, makeup and clothes, just do as you are told Jayne.”

Suitably told off I did as she asked and was changed ready and waiting when she came out of the shower wearing just a towel wrapped around her with another as a turban on her head?”

“Kelly, despite all this I am still a man, can we both be a little more discreet please.”

“Oh, grow up Jayne, while we are here we are two girls sharing a room, just get used to the idea, did your sisters never walk around like this or in just their underwear? Think of me as just another one of your sisters that you have no sexual fantasies about.”

When she had dried off and put on her underwear and dressing gown, she shaped and painted my fingernails in the deep indigo shade to match my toes, and started on my hair.

“You have quite good thick hair with natural waves, a lot of girls would kill for something so easily manageable, Let me just style it a bit so that it sits behind your ears to show off your new earrings, give it a spray to hold it, then there is just your makeup to do before getting dressed.”

She was an expert with the makeup and after trimming and shaping my eyebrows a little just to get rid of some of the bushiness soon had me finished and left me to get dressed while she sorted herself out.

“Put on the shimmer tights first, your blue sheath dress and the matching heels, then walk around a bit to get used to the shoes.”

We were soon both ready to go to meet the others over dinner and I made my way to the door to the room.

“ Don’t you think that you have forgotten something Jayne? A girl never goes anywhere without her bag. Put your lipstick, mascara, a few tissues and your purse in your clutch bag, and you can borrow a couple of my sanitary pads and tampons to put in there too in case anyone asks you for help in the Ladies, then we can go.”

I stopped to have last look at myself in the full-length mirror next to the door and didn’t believe how I looked and how everything had changed in the short time since I met Kelly.

“ Come on girl, stop staring at yourself in the mirror, you look just fine, in fact you are almost as attractive as me, just remember who you are now and you will have no problems.

To be continued