The Greatest Gifts

December 2021 Christmas Holidays Story Contest Entry



I had not been looking forward to Christmas at all. It had been a really tough year for me and I needed to just get away from everyone and clear my head.

It had all started when my wife, Mandy, came home early from work as she was not feeling very well, coming down with a heavy cold or flu. Regrettably she came in to find me wearing my daily work look, which unfortunately comprised a skirt and blouse, tights, full makeup and with my hair brushed in a very feminine style. As a webpage designer, I worked freelance from home and I had found that indulging in my fantasy helped the creative juices to flow and assisted my artistic flair.

For as long as I could remember I had secretly dressed in my older sisters’ clothes whenever I could and there was nobody else around. I felt myself to be an outsider when they were playing their games, even though they sometimes roped me in when they needed an extra girl and dressed me up to play with them.

I have often read about boys joining in, or being forced to join in, with their sisters when they were young, but usually they grew out of it as they matured. However with me that did not happen, the older I got the stronger became my compulsion, particularly in the teens when girls clothes seemed to change into softer, fancier, more feminine, styles, and my sisters got into makeup and more sophisticated hairstyles. At the time crossdressing was not as widespread or publicised as it is now and it was not something that was openly done and I tried to hide my feelings by becoming ‘one of the lads’, playing football, talking about and tinkering with cars and motorbikes, generally fitting in with what was expected of me.

At university I started going out with Amanda, or Mandy as she preferred to be called, as all my friends were beginning to pair up and the choices at the time were between becoming a lonely computer nerd, or having a social life as a member of our couples group. Mandy and I got on really well, enjoyed a lot of similar activities, going to the theatres, restaurants, trips out into the countryside and coast, long country walks, and really enjoyed each others company. This eventually, as was the norm at the time, led to setting up home together and getting married.

All through this, we enjoyed a ‘normal’ happy married life, my crossdressing urges were kept under control and were put to the back of my mind. However after a couple of years we were both trying to develop our careers, working long hours, hardly having time to talk to or pay attention to each other, our sex life waning, and a little bit of boredom settled in.

One day, searching for images for a website I was developing, I came across a picture of a beautiful transgender woman who was successfully working as a TV presenter, which brought back memories of my childhood fantasies. Over the next few days my interest nagged away at me and I started visiting websites geared up to the transgender community, clothes, makeup, hairdressing and deportment tutorial videos, story sites, shops selling specialist clothing to ‘enhance and emphasise your womanly figure’ and it became an obsession for me.

When Mandy was away for a few days on a business trip, the inevitable happened and I tried on some of her clothes. I was a bit taller and heavier than her so the choice of things that would fit me were limited, but I found a skirt and blouse that I could squeeze into, raided her underwear drawer for a bra, panties, and tights and I was soon dressed as my teenage fantasy alter-ego, Helen. I had never really got into makeup in my younger years, but I had sat and watched Mandy on many occasions as she was getting ready for work or for going out so had a fair idea of the basics and was soon quite presentable as Helen.

For the next two days I worked and lived as Helen, and was quite comfortable in the role, even going down to the supermarket for some essential shopping, adding a few sets of underwear and a couple of tops from their clothes section. By the time Mandy returned everything was hidden away, back to normal, and no trace of Helen remained.

Mandy worked long hours, she had an hour’s travel each way from our home in rural Alnwick to her office in the city centre of Newcastle and usually worked overtime, so I was free to become Helen from early morning to late evening, and was soon spending much more time in a skirt than in trousers. I was quite comfortable, as soon as Mandy left for the day, I was getting myself ready for work as Helen. I was fortunate in that virtually all my contact with clients was by email and that face-to-face contact was almost non-existent, so that I was able to just continue with my work without any problems. In fact I found that I was more relaxed and free-thinking as Helen and that the quality of my website designs improved, bringing in a lot more contracts.

Things were going well until the inevitable happened, as Mandy came in unexpectedly to find me. or rather Helen, in the kitchen preparing a casserole for our dinner. I normally had more time to do the cooking than she had, and it was something I enjoyed. especially when dressed as Helen.

“Who are you, where is Alan, and why are you in my kitchen?”

“Just let me explain Helen,” I muttered all flustered trying to think of what to say. I couldn’t think of any reasonable excuse to be looking as I was or explaining why another woman was in the house, so I decided to be honest with her and face the consequences. “ It’s me Mandy, despite what I look like. This must come as a major shock to you, but this is how I dress now through the day, when I am working or going out shopping.”

“Did i hear you right, you actually go out dressed like that, what if someone you know had seen you?”

“You didn’t recognise me when you came in, why should anyone else? Even if I say so myself, I think that I look quite normal and natural a a woman. All the many times I have been out nobody has made any comment or appeared to look at me questionably, and I have even been in the queue at the supermarket till next to our neighbours without being recognised.”

“ I must admit that you do look good, and your makeup and hair is so well done, as if you have been doing it all your life, but why?”

“I don’t know why, but from being very young, I have always felt an urge to dress in girls’ or women’s clothes. I regularly secretly dressed in my early teens, but haven’t done so for many years, until I started again a few weeks ago. Let me go and get changed and then we can talk this through.”

“ No, just stay as you are, get on with preparing the dinner while I go and get showered and changed, and have a think about this.”

I cooked and served the casserole, called up to her and nervously awaited her coming back downstairs, but she seemed quite calm, not angry and aggressive as I expected.

“Before we start, what do you call yourself when you are dressed, I can’t bring myself to call you Alan anymore?”

“When I have been chatting to people at the table over a coffee when I have been out, I’ve always introduce myself as Helen,”

“Ok Helen, while we are eating, you can tell me a lot more about how long this has been going on and try to help me understand.”

Over dinner I tried to tell her about the childhood games and my fantasies as a teen, but I found it very hard myself to understand why I felt this urge to dress as a female, never mind explain it to her.”

“So, do you really want to live as a woman, or even become a woman, or is this just some sort of sexual game or fantasy?”

“I don’t really know how far I want this to go, I just know that for the time being I am comfortable as Helen, and if there is a way to continue, I would like to stay like this for the present.”

“ I need to have a good think about this. I am not going to rant and rave, call you names or insult you, but I am not sure that I am comfortable with living with you as Helen, at the moment I think that it might be best to think about separating.“

That is what happened, she decided that she wanted to live with a ‘real man’, a few weeks later I moved out into a small flat, taking all my personal belongings with me, including all my male clothes as I was still unclear as to what I intended to do and wanted to keep my options open, although I was now living 24/7 as Helen.

Christmas looked like it was going to be a lonely and miserable time this year. Mandy, whilst not being nasty, was keeping her distance, most of ‘our’ friends were really her friends and wouldn’t want to know me, particularly if they found out why we had split up, my sisters lived at the other end of the country and had already made arrangements to visit their husbands’ families anyway. It looked like I was stuck with hiding away in a small pokey flat, by myself, watching everyone on TV being merry and enjoying themselves. I decided that I needed to get away for a break from everything and try to clear my head as to what I wanted to do with my life.

I did a search for holiday rental properties still available and found that most were already fully booked for the season, but managed to find a place still free up on the high North Pennine moors where Cumbria, Northumberland and County Durham all merge into each other. It was a refurbished and modernised old shepherds’ hut which had served as an overnight shelter when they were on the moors rounding up the flocks in bad weather or when bringing them down for shearing. It looked quite remote with no near neighbours, and was about a ¼ mile up a track away from the nearest road, but according to the online details appeared to have all the services and facilities that I would need.

After work on the Friday of the weekend before Christmas I prepared myself for my holiday, waxed everywhere, soaked myself with moisturiser, gave my hair a good wash and condition and packed my cases with a wide choice of clothes and accessories to last me the fortnight to cover Christmas and the New Year.

As it was to be at least an hour and a half, 70 miles drive, mainly on narrow country roads, I thought it best in case of an accident or being pulled over by police not to be in full feminine mode, so wearing no makeup and dressed neutrally in a sloppy sweater, skinny jeans, and loafers, I made my way to pick up the keys from the letting agent in Allendale, not far from the cottage. Before going into the agents I pulled into a remote corner of a car park, put on basic makeup, slipped my breast forms into my bra and transformed myself back into my now normal appearance as Helen. That was it now, for the next two weeks Helen was to be on holiday, relaxing and walking the fells and moors, with no worries about meeting anyone who might recognise me.

The cottage was exactly as described on the website. a quaint converted barn, with an open-plan kitchen and living area, two double bedrooms, and a modern bathroom, all more than enough for me to be comfortable. It had a small enclosed flower garden which merged into extensive views over the fells and offered me the peace, tranquility and solitude that I needed.


After unloading the car of my cases and bags of groceries, I lit a roaring fire, changed into a skirt, fixed my breast forms to my chest as Helen was here to stay for the holidays, pulled on a top and chunky warm cardigan and sat down with a glass of wine to settle myself in.

The rest of the week before Christmas I managed to get out most days walking the fells, enjoying the magnificent views in almost every direction, after all I was staying at one of the highest points in England and could see for many miles. Although I welcomed the solitude to give me time to think about what I wanted to do with my life, I also enjoyed time in company and most days, either for lunch or evening dinner, stopped of at one of the local pubs I came across on my travels around. I got a few querying looks from some of the local regulars, but it was just inquisitiveness about a single female stranger rather than anyone reading me, and I usually ended up in conversation with someone and spending a pleasant time in friendly company.

I had decided that although I was happy mixing with people, Christmas Day in company would be too emotional and had brought all the ingredients for a traditional Christmas dinner with me, a small turkey crown, a gammon joint, all the vegetables including the once-a-year portion of Brussel Sprouts, a small Christmas pudding and cake, a bottle of celebration ‘fizz’ and a case of wine to see me through the two weeks.

It was just as well that I had not planned to go out on Christmas Eve as the heavens opened and the torrential rain never stopped all day. This allowed me plenty time to put up a small tree I had brought with me, decorate it and add a few festive trinkets around the place, without feeling that I was missing out on more time on the fells. I was determined to make the most of my first Christmas as Helen and enjoy it as much as possible, even though I was on my own.

To get in the festive mood I changed into a new dress. bright cherry red, half sleeves, just above the knee and brightened up my makeup, and settled down to watch TV, it was if I was having my own private party. However my peace was shattered by heavy banging at the door and when I opened it I saw two absolutely drenched figures all covered up in hooded cagoules.

“Can you help us and let us use your phone please?”whimpered a young female voice.

“Come in out of the rain, you’ll catch your death out there, and I’ll see what I can do to help. Now, what is the problem?”

“We were on our way to a party with friends in Alston and the car skidded on a puddle in the road and we ended up in a ditch just down the way from your cottage, saw the light in your windows, and thought that you might be able to help us.”

“You’re out of luck, there is no phone or broadband here, mobile phone signals are a bit iffy at the best of times and in this storm there is no chance of a signal. Is your car leaving the road clear or are you blocking it, we don’t want another accident?”

“The car is locked and safe, but I don’t know what to do now.”

“Even if the phones were working, you are not going to get anybody to come out on Christmas Eve, especially in this storm. I have a spare room here and you are welcome to stay the night or until the storm dies down, I don’t fancy driving you anywhere in this rain.” I offered without even considering the possibility of being discovered.

“That’s so kind, we’ll go back to the car to get our things, we are soaked anyway, so another few minutes out there won’t make any difference. I’m Julie and this is my friend Chrissie, by the way.”

“I’m Helen, go and get what you need from your car and we’ll talk later.”

While the girls got their stuff, and then went to the spare room to get dried off and changed, I put on a pot of broth to warm them up, luckily I had brought all the lentils and herbs to use up any left-over turkey scraps from Christmas dinner., and added potatoes and diced beef to give it a bit more texture and flavour

The girls, having seen the way I was dressed followed suit and came back out of their room wearing the dresses they had been intending to wear at the party, so there we all were, all dressed up with nowhere to go.

“Thanks again, this is really good of you, are you sure you don’t mind?” Chrissie said between mouthfuls of hot warming broth and wheaten bread.

“To be honest I’m glad of the company, it’s no problem. The storm is not getting any better, why not stay the night and tomorrow and then it will be easier to get this sorted out. I have got enough here to see us all through the next few days.”

We soon had the place tidied up and the dishes washed, the girls admitting that they never did that at home, but were glad to help.

We had an enjoyable night, drinking wine with us all telling our stories of where we were from and what we did. The girls were students in their final year at university and were on their way to a party with some of their college friends at the family home about 10 miles away, they had almost completed their journey when Chrissie lost control of the car. I gave them the mostly true story of that my marriage had broken down and that I was spending the holiday up here in the hills to try to sort out what I wanted to do next, obviously with no mention of my true self.

The girls were easy to get on with and I soon relaxed, no longer worried about my real identity being exposed, the girls just chattered away to me as if I was an old friend and it became second nature for me to react and answer as Helen. Other than with my sisters when younger I had never really been comfortable in the company of women and had found it difficult to have anything more than polite chat but, probably because to all intents I was now a woman like them, it was easy to relate to Chrissie and Julie and the evening flew by so fast, before we put the bits and pieces away and went to our rooms to get ready for bed.

I was in such a good relaxed mood that I had the best sleep since leaving Mandy and woke up all fresh and ready for the celebrations of the day ahead. I already had the turkey slow-cooking in the range and had the vegetables cleaned and cut up before the girls appeared from their room, like me still in their nighties and dressing gowns .

“ Right girls, Happy Christmas, it is still stormy out there so we are stuck together for today, so let’s make the most of it. A quick glass of Bucks Fizz to celebrate and then we can all get dressed and whatever, and enjoy the rest of the day. “

I discretely shaved and showered and, probably tuning in to the femininity of the girls, I changed into the one frilly sexy bra and panties set that I had, put on my red dress again and matching heels, took extra care with my makeup adding a bit of sparkle powder, and bounced out looking forward to the celebrations. While waiting for the girls to appear I made up some bacon rolls to start us off and keep us going until dinner and to help soak up all the wine we had drunk the night before.

“ Hey, they look good, just what we need, a nice bit of real comfort food. We were taking some champagne and wine to the party, so let’s put that into the kitty and let us help you with the dinner. You’ll tell us what you need us to do, we are not the best of cooks, at uni we tend to live on takeaways and pizza.”

“If you are really interested, watch and learn and do as I ask, otherwise just keep the place tidy and the dishes washed after I do things, and most importantly keep my wine glass topped up.”

The girls were a big help and we chatted and joked as we did things, it made the day much more enjoyable than if I had just been on my own. After a really tasty and filling dinner we were not in the mood for anything too strenuous and just sat and watched all the tv Christmas specials while we chatted, until the excitement of the day, the heavy meal, and the wine all combined to make us dozy and convince us that it was time for bed. Three of us needing to use the one bathroom to clean off makeup and get ready meant that while one of us was in there the others got changed into our nighties and brushed out our hair, but we were all soon done, and with quick goodnight hugs made our way to bed.

Boxing day was a lot brighter, the rain had stopped and there were clear blue patches in the sky. After a long lie-in to recover from the excesses of the big day, we dressed casually in jeans and jackets and went down to check on Chrissie’s car. It was stuck in a ditch and didn’t seem too badly damaged other than one of the front wheels that had fallen into the ditch looked not quite right. There was no way that we would be able to shift it and went back to the cottage to see whether we could call out a tow truck to get it to a garage. We were able to pick up a mobile mast signal but then our luck ran out. none of the garages listed in the cottage’s customer information file answered and just switched to a message service, which we half-expected really, it would obviously have to wait for the next day when hopefully at least one of them would be back at work.

“Do you girls fancy going for a walk to blow the cobwebs away, it’s a Boxing Day tradition with me? There are plenty of long challenging walks, I was over Cross Fell the other day and there are brilliant views from the top but it is probably a bit much today, especially as you are not used to long treks, and will be quite boggy after all that rain. There are some nice circular routes around Nenthead, just up the road over the border into Westmorland, or Cumbria as they insist on calling it nowadays. You don’t need proper hiking boots for those, any decent sturdy flat shoes or boots should do, and your cagoules are all dried out now.”

“ Why not, it will do us good and set us up nicely for finishing off the turkey and leftovers from yesterday. we have plenty of warm clothes but have you any decent thick socks to keep our feet warm and blister-free?”

Three hours later, after a brisk invigorating walk we returned tired, but rosy-cheeked, to the comfort of the cottage, and warmed ourselves up with bowls of hot broth to which I had added a lot of the turkey scraps to liven it up a bit.

The next morning Chrissie managed to get a local garage to come out to inspect their car and tow it out of the ditch and we all went down the track to meet the mechanic.

“What do you reckon, now you have it back on the road do you think it is ok, or do you think it needs any repairs.” Chrissie asked.

“ Oh you have a problem luv, that front suspension is gone, and it’s not an easy or quick job, it’ll take a couple of days to get replacement parts and it won’t be cheap. Are you ok to stay around or do you want to leave it with me for a while?” he replied with the sharp intake of breath that tradesmen always do, especially when dealing with women, who were in his opinion totally ignorant of the technicalities. I smiled and nodded to Chrissie to let her know that she could stay as long as necessary, or at least until I had to leave the cottage after New Year, and then turned to the mechanic.

“Obviously ou will know better when you get it up on the ramps, but the mountings and ball-joints look ok to me, surely it is just a matter of replacing the bent strut, which is not a major job.” I jumped in, taking him by surprise, “I have done that myself a couple of times before.”

“As you say it may be easier than I first thought, I’ll know better when I get it back in the workshop.” he replied with a frustrated look.

“ When you have had the chance to inspect it properly, give Chrissie a call with a quote to fix it, because if it looks to be a major job the assessor for her insurance company will probably want to approve the work and the costs beforehand.”

“ Ok” he said grumpily before hitching up the towbar and driving off.

Chrissie came over and gave me a big hug. “You were brilliant Helen, I saw the pound notes in his eyes when he thought he was dealing with a load of ignorant women, but I think he realised that you weren’t going to let him get away with ripping me off.”

“It’s all part of my chequered past, I have helped people working on cars lots of times,” I smiled in return, “and I don’t like to see patronising men take advantage of us girls, trying to baffle us with technicalities.”. I suddenly realised that, even though I had been living as a woman for some time now, this was the first time that I had unthinkingly aligned myself with a female point of view.

The next couple of days the three of us toured the area waiting for the car to be repaired, more walks on the fells, Hexham Abbey and Hadrians Wall, High Force Waterfalls, generally appreciating the wild beauty of the area. On a visit to Killhope Mining museum, not far from the cottage, I discovered the paintings of the museum by Lexie Robson, a local artist who worked in her studio in St John’s Chapel. I was intrigued when told the gossip that she was actually transgender and I decided to visit her at her studio.

Although we had been told that Lexie lived in St John's Chapel, they were unable to give us an exact address, so we pulled in to the local pub, the Maltby Arms, for a drink and to ask, the barmaid, Julie for Lexie's exact whereabouts.

"What is it you want to see her about, she likes to keep herself to herself?" she asked.

"I'm a fellow artist, although I work on graphic design rather that paint and brushes, and from what I understand, we have a lot in common?"

"Lexie is my cousin, let me ring her to see if she wants your all to visit."

"OK, she is happy to see you, it's the third cottage on the left through the village, the one with the red shutters and door."

We were greeted by a tallish but very feminine woman and it was hard to believe that she had once been a man. The girls went off to look at the paintings of the local landscapes and I chatted to Lexie about her work and I told her about my website and graphic design projects..

“I hope you aren’t offended but I guess you are like me and that is why you came here.” she said softly so that the girls would not hear.

“Is it that obvious, I am nowhere near as convincing as you, but then I have only been serious about living as woman for a few weeks and still have a long way to go and decisions to make.”

“When Julie rang she suspected that you were TG when you told her we had a lot in common, but we wasn't sure and was too embarrassed to suggest it to you. If you are serious, keep at it, you are doing really well, I take it that your friends know about you?”

“No, they don’t, I’ve only know them since we were thrown together by the storm on Christmas Eve, and am getting on really well with them, I didn’t want to spoil things by telling them.”

“A word of advice, if they are good friends they will accept you, if they turn away from you it will be best to forget them and find better friends. I have been lucky, this is a small village community and I have fitted in with them and been accepted. If you are going to live as, or fully become, a woman you have to work at it and convince people that you have a contribution to make.”

“Thanks Lexie, you’re right, they deserve to be told, I’ll pick the right moment and see how it goes, and I’ll let you know what happens.” I told her as I gave her a sisterly hug.

The next morning Chrissie had a call to say her car was ready and, to the surprise of none of us, that the damage and the cost was nowhere near as bad as the mechanic had originally suggested.

“That’s great news Chrissie, but I suppose that means that you will be on your way now.”

“We’ve been talking about that. You have been so good to us and it’s New Year in a couple of days. If it’s ok with you we would like to stay with you over the holiday, we can’t let you see the New Year in all by yourself, can we?”

“Of course, I would love that, it’s so thoughtful. Come here for a group hug, and then we will go and get a few more supplies in for a bit of a party.”

Even though it was only the three of us, we got all glammed up to see in the New Year in dresses and full makeup, tidied up each others hair and had a super time, I was going to miss the girls when we left the next day to go home, I had got used to being in company again.

We were all packed, the cars loaded up, the cottage cleaned and tidied, and were ready to go when I told the girls to sit down again as there was something I needed to tell them.

“I’ve had a brilliant time with you, I couldn’t have had a better Christmas and New Year, and you have helped me make a decision. It may come as a big shock but I am not who you think I am, I am not really Helen. My true name is Alan, and I am a man, although I am now intending to fully transition as soon as I can get it sorted out.”

I Told them all about my childhood the problems after being discovered by Mandy, and how after realising that I had relaxed and fitted in with them that I was now intending to continue to live as a woman

“I thought that you deserved to know after the time we have spent together, I hope that does not change what you think of me, and that you will remember the good times we have had rather than the fact that I deceived you.”

“ Oh, don’t worry about that, we had our suspicions that things were not quite as they appeared, early on when you had a few drinks you let your image slip a bit, but you were being so kind to us that we didn’t want to embarrass you by saying anything. When we saw you having a whispered conversation with Lexie Robson that confirmed it, you looked like you were sharing secrets.” Julie quickly replied.

“ Over the last few days, you have relaxed with us and are becoming totally natural as a woman in our company, you make a lovely, kind, attractive, woman and despite what your body might be, or might have been, you are female inside, and we love you for it. If Mandy does not want to know you anymore that is her loss, you are better off without her. Let’s keep in touch, we must meet up occasionally, but only if you stay as Helen, I don’t want my memories spoilt by meeting Alan.” added Chrissie.”

I started to cry at their kindness and they came over and hugged me tight and cried with me.

“You have been so kind letting us stay with you, and putting that mechanic in his place, I’m sorry that we did not have a Christmas gift for you to repay you.”

“Don’t worry about that girls, we’ll get together again soon, but we now need to get on our way. You have given me the greatest gifts you could have, friendship, understanding, and acceptance, they are worth a lot more to me than a few trinkets.”

The End

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