It was a cold winters night, the week before Christmas. The sky was dark and mysterious with only the moon peeking through the snow-clouds. All the stores were closed and shuttered, all the streets were empty dark and bare. Nobody in the right mind was out and about on such a bitter unwelcoming night, the only sparks of life were the homeless shivering in shop doorways, wrapped in cardboard, paper, or whatever other items for warmth and protection that they could salvage.

I was more fortunate than most of those living on the streets, my overnight pitch was in the loading bay of a supermarket, next to the warmth coming from the refrigeration system condensers which managed to keep the worst effects of the winter chill from my bones. My pitch was next to the skips where a lot of the unsold food items were thrown away, for the likes of me to rummage through the bins to scavenge food to try and keep body and soul together.

I had only been on the streets for a couple of weeks but had been struggling with depression and self-doubt for several months. Most of the others like me had suffered for a lot longer and drowned their sorrows and misery in alcohol leading them down the path to death from malnutrition, alcohol poisoning or hypothermia. I still had hopes and dreams that this misery would end and I would be able to get back to my former life.

When I couldn’t sleep I thought hard and long about how I had descended from the high life I used to live, penthouse apartment, high-powered and ludicrously paid job in finance, trophy girlfriend, and how I had come to be in the awful situation that I was now in. I had lived life in the fast lane, expensive cars, hand-made suits shoes and shirts, gourmet restaurants, prestige wines, a wide circle of similar colleagues who were only too glad of my company. I had it all, but looking back my life was shallow and meaningless. All the vast amounts of money I earned ended up in the pockets of grasping landlords, overpriced restaurants and clubs and couturier clothes and sparkling trinkets for Charlotte, my fawning clothes-horse of a girlfriend.

I was just about to escape into sleep when I heard someone approach me. In the short time I had been sleeping rough I had come to learn it usually meant either Police who were normally ok as long as you moved on until they had left, Security guards who were a lot more intolerant brusque and even violent, or other rough-sleepers who were looking to steal the few possessions or scraps of food that I had. However this one was different, it was a young woman, well wrapped up in warm winter clothes with her long-blonde hair peeking out from under her woolen hat and wearing a pleasant welcoming smile.

“Hello dear, are you all right. It’s not safe for a young woman like yourself to be out on the streets at any time of year and on a winters night like this is not good for your health. I help at the local homeless shelter two blocks away, and we are trying to help get everyone off the streets into the shelter, at least over the Christmas period, would you like to join us to get cleaned up, some warm and dry clothes and some hot food and drink?”

I was in two minds as to how to reply, do I sharply respond that I am a man and tell her to get lost, do I politely correct her and see if the offer was still on the table, or do I just go along with her and continue to let het think that I am a woman? She didn’t deserve the first as she was trying to be kind and help me, the third would not work for long, so I settled on going with her and on the way to the shelter would politely and gently correct her. I smiled and thanked her, she helped me to get up and collect what few possessions I had before setting off.

“I’m Angie Cooper, I volunteer at the shelter all year round, but this is the busiest time of the year for us. Apart from the weather conditions being awful, Christmas is an especially emotive time and a lot of extra volunteers come in to help out for the season, but there are never enough of us to cope with all the demands on our time and resources. You do not look in too bad a condition, but many of the people we help are too far gone into the depths of alcohol or drugs, and unfortunately after a few days with us getting clean and warm they just leave and go back to their life on the streets.”

“Thank you for this Angie, your name is very appropriate, you are an angel for what you do. My name is Jay Shepherd, and I am relatively new to all of this, I’ve only been homeless for a few weeks and haven’t yet got the point where I have stopped looking for a way out. I hope this’ll not make you feel embarrassed, but I am not the young woman you think I am, I’m actually a man, although at this moment I don’t look on myself as a very good example of what I should be.”

“Sorry for getting that wrong, I hope I haven’t offended you, but it’s an easy mistake to make. You are quite small and slight, not much bigger than I am, your hair is long and curly where it shows under your beanie hat, and unlike most of the men on the streets you are clean-shaven with quite a fresh complexion.”

“When we get in the warmth of the shelter I will tell you all about me, I don’t have much now but one of the things I am trying to retain is my dignity. You found me at my regular pitch behind the supermarket and most days I go in there first thing in the morning to use their washroom, have a wash, when necessary a shave, and try to keep myself looking half-decent just in case an opportunity comes up for a job and somewhere to stay, I live in hope and haven’t yet sunk into despair.”

We soon arrived at the shelter, which was run by community socially-minded volunteers rather than the church groups normally running the places, who, in addition to all the charitable work, usually also used them as a platform for a bit of evangelising trying to get their residents on the path to moral righteousness.

“Ok Jay, most of our visitors head straight for the food counter, but since you seem to take pride in your appearance, why not go for a shower and get cleaned up first, I will try to find you some clean dry clothes and we will put yours in for cleaning.”

As Angie had suggested, I made for the shower cubicles, stripped off and enjoyed the warm and stimulating spray, gave myself a good soaping, shampooed my hair, even using some of the scented conditioner and body wash from the shelf in the cubicle, and after shaving using one of the disposable packaged razors I began to almost feel human and normal again.

After drying myself off I peered out from the cubicle to see a pile of clothes on the bench outside, and had a good look at what she had given me. I was slightly shocked to see that the things she had found for me were obviously women’s clothes, leggings, a flimsy vest-like top, a chunky-knit woolen jumper, and loafers, but at least she had the decency to leave men’s underpants rather than women’s, I felt I had no choice but to put them on, but although they were women’s clothes they were not overly feminine and they were at least clean and dry.

She had also had the forethought to leave a hairbrush which I ran through my drying shoulder-length hair to get rid of all the tangles to make myself presentable, before going out into the main hall to try to find Angie. I found her at the food counter serving soup, rolls, and hot coffee to a dwindling queue, most of the people coming in for the night had already arrived and had been fed.

“Hi Jay, you are looking a lot more presentable. Apologies for the choice of clothes, but they were all I could find quickly in your size, we’ll sort something more appropriate tomorrow.”

“ They are only clothes, they, are clean and comfortable, they will be ok, for the moment.”

“Excuse me darling but are you two girls going to be gossiping all night, I am waiting for my supper, move along.” snapped a scruffy older man mistaking me for a woman, patting me on the bottom, partly to push me along, but from the twinkle that came to his eye I think that there was more to it than that.

“I’ll be finished soon Jay, come on round this side of the counter and help me clear up, we can talk more later.” Angie giggled while defusing the situation and saving me from further embarrassment before I had time to react to the man’s unwelcome touch.

“Before we start, as we are serving the meal, you need to tie your hair back like I have so that it doesn’t get into the food.” Angie told me as she fished into her bag, pulled out a small scrunchie, fixed my hair in a high bunch and I was ready to start. I was introduced to the other volunteers, Liz and Jacquie, and the four of us were soon quite organised, working well together and chatting between chores.

“It’s the first time we have seen you helping here Jay, hopefully you will enjoy it and become a regular, we can always use more volunteers.” Jacquie assumed that I was another willing helper rather than someone who had come in off the streets for shelter and warmth. Accepting that dressed as I was and sweet -smelling from the scented soaps It was assumed that I was a woman, with clean clothes and brushed hair I came across as just another socially minded citizen, and I just played along with it, and the other woman just treated me as such.

“Ok Jay, that’s us done for the night, there’s a bowl of soup and some bread for you, I’ll grab a coffee, we’ll find a spare table and you can tell me all about yourself, you are so different from the people we normally get in here.”

“It all started about six months ago just after Easter. I worked as an investment banker in our regional office in the city centre, gambling with other peoples cash, earning silly amounts of money and living the associated high life, fancy car, flash penthouse apartment, gorgeous trophy girlfriend, you know the type, designer clothes, expensive hairdo, daily beauty-parlour visits, all big boobs and legs up to her armpits It was generally an expensive lifestyle, and as fast as the money came to me, it went away again.

It all seemed too good to be true, and as is often the case it was, and couldn’t last forever. It all came crashing down when my boss told me that they were downsizing, closing the regional office were I worked. and that unfortunately there was not an opening for me in the new set up. I was sacked with immediate effect, given a not particularly generous severance payoff ,and that was the end of that.

I tried get another job, but similar work was not available, and at interviews for lower-paid jobs it was obvious that the interviewers thought that I would be a fly-by-night, only with them for a short time until something better came up. I ended up sitting around the apartment all day, slouching in leisurewear, not taking any interest in my hygiene or grooming, watching mind-numbing daytime tv, most of it aimed at stay-at-home women and I became more and more despondent disillusioned and miserable.

Money was quickly running out, although I had been investing for other people, I had thought that the gravy train I was on would never be derailed and hadn’t looked after my own future, I had no significant investments or savings that I could fall back on. It got to the point were I could no longer afford the apartment or the lifestyle and had to review how we could economise. However my girlfriend was having none of it, she had got used to expensive living and was not prepared to change, it didn't take her long to find herself another bank roller who could keep her in the manner to which she had become accustomed. Before she left the spiteful bitch trashed all my belongings and clothes other than the stuff you found me in, almost drained the bank account, maxed on the credit cards and left me with virtually nothing. That’s when I ended up on the streets.

Seeing where the homeless gathered and how they lived made me more depressed and I promised myself that I would never became aimless like them and that’s when I found the pitch behind the supermarket where you came across me. Although I was on my own, , keeping away from other homeless groups, which made me more vulnerable, at least I was not getting dragged into the pitiful misery that your other customers have arrived at.”

“That’s such a sad story Jay, you must feel particularly bad about the way your girlfriend reacted, what she did to you was callous and evil, you are better off without her.”

“Every cloud has a silver lining Angie, at least it introduced me to you and the wonderful work you do, and it gives me hope for the future. What happens now, is there a bed for the night for me?”

“The men’s dormitory is already full, and besides it would not be a good idea for you to be in there, most of them will.see you as a girl, wearing those clothes smelling of the perfumed soap and with your hair tied in a bunch. I could put you in the woman’s dorm, but that could leave us all open to claims of sexual abuse. I believe you to be a good person despite your circumstances and am prepared to take a risk with you. I have a spare room and bed at my small flat which you can use for a few days over the holidays if you want that.”

“That’s ever so kind, but I have next to no money and won’t be able to pay any rent or chip in for food.”

“ Don’t worry about that, I am well provided for by my parents to supplement my earnings as a secretary in a large stockbroker practice, and I will enjoy the company over the holiday period. The only thing I ask in return is that as long as you stay with me you continue to volunteer here and that you try to find a job, is that agreed?”

“That would be wonderful, let's go and get me settled in, but I’m not dressed to go out in this weather, can you find me a coat and hat and preferably some boots, these loafers are not really fit for walking through the snow.”

Angie’s flat was only a ten minute walk from the shelter, but I was glad to arrive and get back into the warmth. She had described it as a small flat but it was anything but that, two large bedrooms each with ensuite, large living room with a picture window giving views across the river to the hills beyond, and a huge spotless kitchen/diner which looked like it was never seriously used.

“Apologies again Jay, but I live alone here, so there are only girls’ clothes. I have dug out a sleep set for you which is basically light short pyjamas which should be ok for tonight. Have a good sleep in the warmth and I’ll see you in the morning.”

She was right , her sleep set was quite flimsy with calf-length shorts and a strappy top, but the apartment and the bed were warm and comfortable and they would serve their purpose. I woke sharply the next morning when Angie came in to tell me that she was heading off to work.

“Just make yourself at home Jay, I’ll be back about 6, and we can go down to the shelter again. If you feel like it, go down early, see Jacquie and she will find you something to do. The clothes I found you yesterday should be alright, but if you fancy a change feel free to have a rummage through my wardrobe and drawers, but don’t pinch the really good stuff. Don’t forget that as far as anyone in concerned, you are a girl, so a little bit of makeup as well could not go amiss.” she chuckled as she left me.

I got up and still in my sleep set went to the kitchen to see what I could find for breakfast, it was mainly light girly stuff, muesli, granola and fruit, but I wanted something more substantial and found some eggs and bread and settled for grapefruit followed by scrambled eggs on toast with fresh roasted coffee. Although it was not exciting or exotic, it was the most enjoyable meal I had had for a while.

I was just planning what I was going to do and whether I could do as she had suggested and pass as a woman, when the door buzzer called. “Parcel for Angie Cooper, it needs to be signed for.” came the voice from the speakerphone. I quickly looked around and grabbed a dressing gown before opening the door.

“Sorry to drag you out of bed Angie, could you sign here please darling?”

That decided me, despite my earlier doubts there had been no bother last hight with everyone accepting me as a girl, and the courier only reinforced that. It was obvious that for the next few days, Jay would have to pretend to be be female and that I had better make the best job of it that I could.

I went to the bathroom, gave my face a really close shave although it didn’t really need it as I am not particularly hairy, did the same to my arms legs and chest, and liberally applied moisturiser all over my body where I could reach. I brushed out my hair and tied it up with a scrunchie as Angie had done last night, but pulled some forward to cut it into a feminine fringe.

I had watched my mother and girlfriend often enough to have a basic understanding of applying makeup, so I went into Angie's bedroom, found her makeup, sat at her dressing table, and went through the process. It was ghastly, I looked like a clown, I had gone overboard on everything, so it all had to be cleaned off and reapplied. This time it was much more subtle and was almost perfect. The third attempt was even better and I felt that it was now acceptable and that I was fit to be seen in public. I next attacked my nails, which were longer than normal, as keeping them trimmed while out on the streets was not a high priority, and was able to give them a reasonable shape before applying two coats of varnish.

Along with make up and clothes, I thought that, although I had got away with it last night, that I needed breasts, although there are many small breasted girls there are very few that are totally flat-chested. I rummaged through Angie’s things and found what looked like a relatively simple well-worn bra and a couple of pairs of plain white cotton panties that would give me plenty of support and concealment that she would probably not mind me borrowing.

Plastic kitchen bags filled with rice worked as breasts which I enhanced with partly filled balloons to give a smooth outer skin effect, and was ready to pick out some clothes.

Obviously, I was not a girl so I thought that I needed to stress my femininity and wear a skirt rather than trousers and raided Angie’s wardrobe. I found a tan suedette knee-length skirt which fitted me well and a contrasting lemon v-necked half-sleeved top which fitted snugly to emphasise my breasts.

All-in-all I was quite pleased with the overall effect, I was surprised that I made a reasonably attractive young woman, and decided to go down to the shelter early to help them prepare for the evening rush, put on the coat and boots from last night, picked up a small shoulder bag, filled it with what little money I still had, added the bare essentials and set off. On the way I stopped off to get my ears pieced and fitted with small pearl studs, after all very few women my age did not have pierced ears.

The shelter was almost empty when I arrived, but I found Jacquie in the back kitchen starting to prepare the evening meal.

“Hello Jay, we weren’t sure if you would be in today, but I’m glad you made it, we are a bit short staffed at the moment. Put your coat and bag in the staff room, change from your boots into your flats, grab an apron and you can help me prepare the veg.”

A few minutes later we were working away on the veg and chatting to pass the time when I caught Jacquie sneaking a look at me, making me worried that she had seen through my disguise.

“I see you’ve made a bit of an effort today Jay,.I like your outfit, it suits you, and a girl is always helped by a bit of makeup. Although I don’t really use too much myself, you younger girls always look brighter with a bit of warpaint.”

“Thanks Jacquie, it’s good of you to say so. You are not that old that you should give up on your looks, we all need to make the best of ourselves.” I felt that one compliment deserved another, relieved that my initial worries were unfounded. As a man, there were few occasions where it was acceptable to compliment a colleague on the way they were dressed or groomed whereas with women is just part of the normal way they talked to each other and I was glad that I had quickly responded as I had, she just seemed to accept it as normal chat.

I was surprised at how friendly and open Jacquie and the other women were, it was totally different from the dog-eat-dog atmosphere of the finance office, where everything had been about point scoring and competitiveness, it was a much better, pleasant, and enjoyable way to work, and I was enjoying my time with them.

Angie came in later and almost collapsed when she saw me and realised who I was, she couldn’t take her eyes off me.

“Jay, have you got a moment, there is something we need to discuss, let’s go to the staff room.”

I finished what I was doing and joined her a few minutes later.

“My god Jay, you have done an amazing job, let me have a good look at you. I know I joked with you about wearing a bit of makeup, and feeling free to raid my stuff, but you have done fantastically well, and where did the boobs suddenly come from? You have had your ears done as well. You have really decided to play the part, If I didn’t know better I would take you for just another one of the girls, and seeing and hearing you with Jacquie you are even starting to talk and move in a feminine manner. This is going to work, girl, believe me.”

“We’ll talk later. I hope you don’t mind the stuff I have borrowed and the makeup I’ve used, when I get a job I’ll pay you back. Now let’s get back to work, we have a lot of hungry mouths to feed.”

The rest of the evening we were kept busy feeding all the men and women who were suffering the winter freeze on the streets in cardboard boxes or huddled in a blanket in a shop doorway. For many of them it was a long-term lifestyle, but for others like me it was a temporary state until they could get their act together again. I was one of the lucky ones, Angie had given me some hope again.

We said our goodbyes to the rest of the women and the few men who made up the volunteer force and made our way back home, or at least to Angie’s home, where we settled in for a glass of wine and a chat before bedtime.

“You did really well today Jay, you have slipped into the role of a woman really easily. If you don’t mind me asking, have you done this sort of thing before, dressing as a woman? I mean even the makeup was applied so well, and you blended in with the others so well, you just seem so natural as a girl.”

“Not really, although at school and university I was in drama clubs, and because of my size and build I was often drafted in for one of the female roles, at times I fitted in better with them than the male group roles. That’s where I learned to apply make up, that and watching my bimbo girlfriend putting on her slap at least twice each day, she was so self-obsessed with her looks. Other than those times, this is my first time in real life. But I decided that if I was going to do this that I would do it the best I can.”

“But don’t you feel awkward or embarrassed about it, I know there are a lot of cross-dressers who live secret lives, but you are now doing it openly, working with women as a woman, acting and expressing yourself as a woman.”

“To be honest, I did feel a bit funny putting on the makeup and getting dressed this morning, but once I was out there, going to get my ears pierced and then working with Jacquie and the other girls I didn’t really think about it and just got on with things as I normally would. The more I worked and chatted with them the easier it became to follow their mannerisms and ways of expressing themselves, so yes, I am comfortable with it and we agreed that I would continue like this as long as I am living here.”

“Thats good to hear, I don’t want you to think that I am making you do anything against your will. As you seem ok with continuing, I would like to suggest something to you unless you feel I am pushing you too far, too fast. On Christmas Day the volunteers put on a bit of a show, sketches, songs, dance routines, very much amateur standard not pretending to be professional quality. Last year, Liz and I along with Sara who no longer helps out due to having had a baby, did a miming and karaoke routine of all the popular carols and Christmas songs, will you take Liz’s place?”

“Sounds like fun, as I said, I used to be in drama groups and am used to performing in public, but I get the feeling that there is something you are not telling me.”

“You’re right, when we did our number last year we dressed in sexy Santa costumes, you know the type of thing, short red flared dresses with white faux fur trim, sparkly tights, red Santa hats and lots of glitter makeup, do you think that you could cope with all that?”

“Where is the costume I will have to wear, I want to make sure that I don’t look stupid or any way male? For the moment my image is female and I don’t want to risk that.”

“ I’ve got the costumes here, I’ll dig them out and you can try one on for size.”

I had soon stripped down to my bra and panties (MY bra and panties?) when Angie came in with what looked not much bigger than a tight tee-shirt.

“Ok Jay, slip into this and let’s see how it looks.” She said with a giggle.

“OMG this is so tight, and so short, are you sure that I look decent in this?”

“ Liz and I will be wearing the same, you’ll be fine, honestly, but I might have to make a few adjustments. Nice slim set of legs by the way, with the sparkly tights they’ll look even slimmer. Take it off again and get changed for bed. Don’t forget to remove all your makeup there are remover pads and moisturiser in my bathroom ”

After her seeing me in my underwear getting changed into the costume, I had no qualms about her seeing me in my pyjamas, particularly as I had kept on the panties to keep my manhood well hidden, so I went back out to finish my wine and say goodnight.

“Same routine again tomorrow Jay, I am actually enjoying having you as my flatmate. Don’t wear the same outfit again, there’s a tartan kilt skirt and cherry red top which should suit you.”

I had a bit of a disturbed sleep dreaming that I was discovered as a male and forced to have GRS to make my body fit the way I was now appearing and woke in a sweat, Nodding back off to sleep I had a second dream that I was forced to give up my comfortable life as a woman and go back onto the streets where everyone knew about me and subjected me to all sorts of abuse, that was an even worse option.

The next day, after Angie had left for work I had a long shower to get rid of the sweaty smell and replace it with the scent of the body wash, put on my makeup, which I got right first time. I remembered that on one of the daytime chat shows a drag queen had described how they concealed their manhood by tucking it all back between their legs and keeping it in place with really tight underwear. I thought that I would give it a try as it might save any embarrassment when changing into the costume for the show and when walking around the house in my pyjamas. It felt a bit awkward and uncomfortable at first, but I soon adjusted to it and was quite pleased with the result.

Angie had left the kilt skirt and top on the bed which I quickly slipped into, looked at myself in her full-length mirror and was very pleased with the whole appearance feeling quite proud of myself. I would never have imagined that I would ever be doing this and that it would work out so well. I put on my boots, collected my coat and bag and was just about to leave for the shelter when the door buzzer sounded again and I was faced with the same courier.

“Another parcel for you Angie, Christmas presents are all coming early.”

“I Don’t think there is anything else on order, so Merry Christmas to you.” I replied smiling sweetly at him.

“Thank you, you are the first person to say that, I appreciate it. Merry Christmas to you too.” He said leaning forward to give me a peck on the cheek making me blush deeply with embarrassment.

Back at the shelter the girls were pleased to see me again, complimenting me on my bright seasonal outfit, particularly the shortish kilt which was bringing a smile to most of the men customers. As it was the day before Christmas Eve we were tremendously busy as word had got around the homeless that they were getting treated well here and that the Christmas lunch was going to be exceptional. By the time Angie arrived I was completely shattered and ready to go back to the flat to relax, but she insisted that I go out with her to see if there was still anybody out there who needed a bed, warmth and hot food.

We managed find a few neglected stragglers who we ushered back to the shelter, sitting them down to a bowl of soup and a big chunk of bread. It was a sobering thought that it was only a short time since I was in the same situation as them. My mind was wandering as I worked, thinking about how lucky i had been to meet Angie. Time seemed to fly as we helped the others to tidy up before making our way home.

“Another parcel came for you today Angie, I left it on the kitchen worktop.”

“It’s for you actually, why don’t you open it, it’s not a Christmas present.”

Opening the parcel there were two packages inside. I opened the small light one first to find a piece of white silky material.”

“What on earth is this Angie.”

“It’s called a waist cincher Jay, when you put it on and we tighten it up, it will squeeze your waist to give you a more feminine shape to help your Santa dress fit better.”

“ Oh right, I suppose I had better open the other one and see if yet is equally exotic.”

The second box contained two large jelly-like lumps.

“Are they what I think they are?” I looked at her questioningly.

“Right on girl, those bags of rice have served their purpose as artificial breasts, but you need something more realistic for when you are performing tomorrow. These are called breast forms, they look and feel almost like the real thing, or so the advert said. Whip off your top and bra and lie down and we’ll see how they look.”

I did as I was told and soon felt something cold and clammy being pressed onto my chest.

“Just put your hand on that and hold it in place while I do the other one. Now put your other hand on that one and keep them there until I tell you to stand up.”

“OK Jay take your hands off and stand up,”

As I stood up I felt a tugging my chest and looked down to see the two forms firmly sticking out from my chest.

“Ok girl, you are now the proud possessor of your own breasts, or as near as we can get for now, Put your bra on again and you will realise why we girls have to wear such things. Put your arms through the straps, drop your breasts into the cups and then reach behind to fasten the clasp. There you are, does that feel more comfortable? Let me adjust the straps to get them all in the right place for you.”

“It all feels funny and my balance is out.”

“Don't worry, you’ll get used to them after a few days. Take your bra off again and I’ll use the glue to clean up the edges of the forms to blend in a bit better with your skin.”

“Get used to them after a few days, using glue? What have you done to me?”

“They’ll stay on as long as you want them to. You did say that if you were dressing as a woman that you wanted to do it as best as you could, what can be more committed than having breasts like the rest of us girls, unless of course you want to back out and go back on the streets on Christmas Eve. If that's your choice don’t think I will let you off that easily and let them be removed before I am ready, you are stuck with them, literally. Go and put on the waist cincher, I’ll come and tighten it up and we’ll see how the Santa outfit looks with your new shape.”

I’m sure that she enjoyed it when she was squeezing me into the cincher, hearing me squeal and pant for breath as she did so, but I had to finally agree that the outfit sat a lot better, with a narrower waist and my new breasts.

“I see that the breasts are not the only change in your figure, all your man bits have disappeared too, I questioned your commitment but I think you are really throwing yourself into this. Get changed into your sleepwear and we’ll have a chat . I’ve better idea, rather than the pyjamas you should now be able to look right in a nightie, now that you have bumps where they should be and not where they shouldn’t be, I’ll get one for you.”

She came back wearing a blue flimsy spaghetti-strapped silk effect full length nightie and handed me a matching ivory one.

“Come on don’t be shy we are now girls together, well almost, to all appearances, strip off but keep on the cincher and tight panties and we’ll see how you look. That really suits you Jay and it fits you so well, let’s clean off our makeup, put on some night cream and sit and finish our drinks.

It was another night of disturbed sleep, trying to find a comfortable sleeping position for my breasts and the strange feel of the silky material swirling around my ankles.

Before leaving for work Angie popped in to remind me to take the costumes for the show with me to the shelter as we would be rehearsing our routine after we had finished serving the meals.

Despite not having much money left I felt that I had to at least make a gesture and buy a small present for Angie to thank her for her kindness in taking me in and helping me get a lot of my confidence back to mix with people again. So I got dressed and left early to stop off at the shops.

Walking down then road I was conscious of the bounce of my breasts it was a totally different sensation to the lifeless weight of the bags of rice that I had been using. At first I was certain that it must be so noticeable and that people would not be able to stop themselves staring at them jiggling around, but looking around I realised that every other woman was showing the same effect. As far as anyone could see I was just one of the many women going about their daily lives and was no different to all the others.

When I had gone shopping for Charlotte, like most men I was a bit embarrassed and uncomfortable looking through the racks of clothes, lingerie and feminine fripperies, but it was so much easier now that I was a woman, I had every right to be lifting things off the racks, feeling the material and closely examining things, there were no giggly glances from the sales assistants. I had a fairly good idea of Angie’s taste and sizes and had no problems finding a lingerie set that I knew she would absolutely love. I also bought her a make up palette to replace the one of hers that I had been using and a box of chocolates. It was not much but it was the best I could afford.

I took everything back to the flat, wrapped them and hid them under my bed, picked up our Santa outfits and full of the joys of Christmas and the good feeling of seeing smiles on everyone’s faces I set off to do my shift helping to prepare the meal for tonight’s customers. All the staff were wearing Santa hats, decorated with tinsel, and festive jumpers trying to bring a bit of jollity into the usual dreary lives of our customers.

Most of the volunteers left early to be with their families to welcome in Christmas immediately after serving the food, leaving with lots of hugs and ‘Merry Christmas’ wishes all round, totally different from the ‘let’s go to the bars and get blotto on expensive wine and booze that had been the ritual at the investment bank, it was a much more genuine friendly and pleasant experience.

Angie, Liz, and I stayed behind to tidy everything up and then get changed to practice our routine. Surprisingly There was no embarrassment for me to strip and change into the costume In front of Angie and Liz, I was wearing the same clothes as them and had the appearance of the same bodies as them, it was a case of ‘all girls together’.

We finally got our act together, all of the solo singing spots were Liz and Angie, my voice was not good enough to lead, but I was quite happy going in as a backing singer and miming to some of the commercial records. We had a lot of fun particularly with them trying to loosen up my hip and leg movements to match theirs as much as was physically possible, before getting our routine as good as it was going to get, changing back into our street clothes, and stopping off at a bar for a quick celebration drink before making our ways home.

“You did really well tonight Jay, you fitted in perfectly with Liz and I. Let’s have an early night, get our beauty sleep so that we are bright and full of life tomorrow. There are three shifts, the early one doing the food preparation, the middle one including us, serving the meal and doing the entertainment, and the late shift clearing up, getting those staying off to the dormitories and getting the unfortunate ones back out onto the street.

I was so tired after all the exertions of the day, that I didn’t even consciously realise that I had cleaned off my makeup and changed into my silky nightie before climbing into my warm bed for the deepest sleep that I had managed since leaving my penthouse apartment.

Christmas morning, still in only our nightdresses Angie and I had a celebration bucks fizz and worked our way through bacon rolls and mince pies before settling down to open the presents. She was over the moon with the new lingerie set and makeup palette but told me off for spending what little money I had on presents for her.

“For a change I actually enjoyed shopping in the women’s departments, as a man I was never comfortable, but now as a woman I was able to enjoy browsing, picking things up and examining them, and even tried on a couple of skirts, even though I couldn’t afford to buy them.”

I was surprised and delighted that she had bought me some dressy earrings, a bracelet and a new skirt, the first of my very own without being borrowed from her wardrobe.

“ As you seem to enjoy shopping let’s hit the boxing Day sales tomorrow and I’ll introduce you to the joys of shopping like you never have felt before, don’t worry about the money, my credit card is my flexible friend.”

Angie had lots of other presents from family and friends, but all my contacts had faded away after my fall from grace, it’s not true when people say that money cannot buy you friends.

We planned on having our main Christmas turkey and trimmings after doing our shift at the shelter so just prepared everything beforehand and put the turkey in the oven on a low heat to slow roast while we were out. We dressed very festively all red and white and applied over-the-top sparkly face and eye makeup, teased our hair a lot fuller than normal and set off to help serve the main Christmas meal.

Most of the residents and day-visitors were already seated and enjoying themselves when we arrived to a chorus of wolf-whistles and cheers. Normally because a lot of the customers were alcohol-dependent we were very strict about it being brought into the shelter, but as a Christmas treat we had large bowls of cider punch for them all to have as a Christmas toast.

The food was already cooked and we merely had to carve slices off the bird and serve the vegetables, followed by plum pudding and custard, but it was us that got all the thanks rather than those on the early shift who has been slaving away in the kitchen. When everything had been cleared away we went to put on our costumes while the other volunteer groups were going through their routines, and it was soon time for our turn.

The three of us burst onto the stage all happy smiles, short skirts and long legs and when the shouts of delight and mild innuendo died down we entertained the crowd for almost a half-hour leading the singing of all the well-known carols and songs with the audience mostly joining in, their faces beaming with happy smile and memories of better times in the past. Several of the regulars came up to join us, encouraging the others to join in too.

Obviously Santa Claus would not be appropriate so it was down to his little helpers, Liz, Angie and me to go around the hall distributing small gifts mainly scarves, gloves or socks to help them keep warm. The looks of appreciation on the happy faces made it all worthwhile, although I could have done without al the hugs, kisses and pats on my bottom, but it was all taken in good spirit as harmless fun. Angie, Liz and I kept on our outfits until we left, waving goodbye to a crowd of warm well fed and happy souls who at least for one day were able to enjoy themselves and remember happier times, quickly putting on our winter coats at the doorway, to make our way home.

We kept on our Santa outfits for the rest of the day, all through our dinner and then lounging on the sofa watching TV Christmas specials. It seemed to keep the festive mood going longer.

I’ve had some good news Jay, I’ve had a promotion at work, I am being upgraded to PA for one of the Partners in the law firm.”

“Good for you, I suppose that I had better start looking for a job for myself, the holiday season will soon be over.”

“That’s the other bit of news, my old job is available and is yours if you want it.”

“Thanks for that but surely I need to apply and be interviewed, we are getting a bit ahead of ourselves.”

“It will be ok, I've had a word with Daddy, told him all about you, and he liked the idea of taking on someone needing help, particularly when I told him you had a lot of experience in finance, but had hit hard times recently.”

“What’s your father got to do with it?”

“Didn’t I tell you, he is the senior partner and effectively owns the firm.The only thing is that I forgot to mention that you are really a man, he thinks that my new flatmate is another girl ”

“So the job is only mine if I continue to live as a woman?”

“Yes, I think so, although he is trying to get a bit of social diversity in the firm, he can be a bit old fashioned, but he likes the idea of a woman coming in on the bottom rung of the ladder and, if you prove yourself willing and capable, working your way up to the top again.”

“Wow that’s a fantastic opportunity, although I am not sure that I want to get back right to the top again, it’s too competitive up there. Life is much pleasanter a bit further down the food chain. Although I am comfortable as a woman here with you and with the girls at the shelter I don’t think that I want to live as a woman for the rest of my life. I may be dressed femininely, but inside I am still male and cannot see myself in a relationship with a man.”

“Have you never heard of lesbians Jay? You are very welcome to stay here with me as my partner, however you look, I think that I have found my soulmate in you.”

“Come on then Angie, prove it, let’s get out of these clothes and into bed together and we’ll see if this is going to work”

Most of Boxing Day morning we spent in bed having decided that our relationship could work and we agreed to give it a try. As she had promised, now that I had agreed to stay living as a woman, Angie took me shopping to start to build up a wardrobe of clothes and shoes, she said “ a girl can never have enough to choose from.”

We returned home heavily laden down with bags of more clothes than I thought I would ever need, cleared space in the wardrobe in my room and put everything away.

“Now that we know that we are ok, and what I am doing, how do we go about getting me the job you promised, so I can start earning some money and paying you back.?”

“Didn’t I mention it, you are starting tomorrow, I had better give you a run down on the people you will be working with and what you will be expected to do. I think you need to start preparing yourself for your future life as a woman Jay, darling.”

The end