The Holiday

by Zoez

 

First you need to know something about me, so here goes. My name is Zoë. I was born a female and always been a girlie girl. At school I dated some cute guys but it was never right. Then I met Sarah, she rocked my world, we were both 16 and realising we were gay. She was my first love. We explored a new world together but when we went off to different universities we found different paths.

After Sarah there was Kelly, Daisy and Helen all amazing in bed but the connection I had with Sarah was never there again. Then there was Tara, I fell in love for a second time with Tara, unlike the others she wasn't technically a woman. She was on her way there, that is to say I never met Tom, her past life. Tara had breasts, a sensitive soul but something between the legs that neither of us liked. She was months away from getting rid of our dislike when suddenly one day a car pulled out and hit her. Killed her.

It took me months and months before I was ready to face the world without Tara but love strikes when you least expect it, I met Chris. Not Chrissie or Christine but Mr Christopher Chelmsford, a man who had never worn a skirt or strayed from being a man. I didn't ever think I would feel something for a man but I fell deep for Chris but as much as I loved him and wanted to be with him, we never fully connected as I did with Sarah. Until now.

I'd been with Chris for 3 years, living with him for 1, when an idea hit me. He worked at home writing books so I figured it wouldn't impact his life too much. I wanted Chris but I also wanted a wife not a husband. So I did what I could and set about making Chris the woman I always hoped he could be.

So one day I when he was drunk I asked him what his parents would have called him if he was born a girl.

'I don't know, I think it would have been Christine or Chrissie.'

'Chrissie? I like that name.' I said.

The next morning he was badly hung-over but able to notice straight away when I called him Chrissie.

'Chrissie?' He asked.

'What?'

'You called me Chrissie?' He queried.

'Yeah of course, you said last night you wished I called you Chrissie.'

'What, why?'

'I don't know Chrissie but that's what you asked me to do and you were pretty demanding about it, so now I'm calling you Chrissie as you asked.' I lied.

'Oh, I don't remember that. My head hurts Zoë!'

'You'll be alright Chrissie.' I told him, this time he didn't argue but just accepted it as he searched his aching brain for the memory of our conversation.

A week later I persuaded him to start taking hormones, except I said they were vitamins. Chrissie is only 5 foot 7 same as me and he had a slight frame and fair body hair never ever needing to shave his face, so I knew that he wouldn't look too out of place wearing a dress. The vitamins were easy to get him taking and like clockwork he took them everyday. Next I convinced him to grow his hair long, it had always been down to his eyes but now he too was convinced he should have a ponytail.

As the months ticked by his body began to change and his waist began to change, skin soften and his chest began to swell. He was a little concerned about his chest but didn't notice anything else happening as it was developing slowly. I gave him some cream to rub on his chest as I told it would help prevent the man boobs he seemed to be getting (luckily he had recently watched a documentary about how some men naturally get them, so this is what he assumed he had). Every morning he took a vitamin and every night he rubbed the cream.

At five months, I convinced him to pierce his ears. He didn't take much persuading actually as he'd always wanted to. He came back with cute studs in his ears. That evening we were going out and I put on my new red dress and asked for his opinion.

'Wow, looks amazing.' He said.

'Thanks Chrissie. You know if you ever want to wear it you can.'

'What?'

'I said thanks Chrissie.'

'And what about if I ever want to wear the dress?'

'What? You want to wear this? I didn't know you were a cross dresser.'

'I'm not, look forget it. It's nice.'

'Thanks, help yourself anytime.' I said but he'd walked off.

 

Then about 6 months after he had his first vitamin, I told Chrissie about this fantastic holiday idea I'd heard about where you go to a lodge in the middle of nowhere in New Zealand and spend 3 weeks there in the middle of the forest. A helicopter drops you off and picks you up, at one and a half weeks it drops supplies but aside from that you don't see another human being. There's no TV but it has an indoor swimming pool, electricity and comfy rooms.

Chrissie loved the idea so we booked it for six months time. Enough time for me to bring out more of Chrissie. His hair was now long enough to tie up but I insisted he kept growing it and wear an Alice band sometimes. If only everything was so easy though, it took me days to convince him to wear a pair of culottes I brought him. He said he didn't like the style but I managed to get him to try them for a day and soon he wanted to shop for another pair. I said I couldn't remember where I got them from, so he kept his eyes out for them in his men's stores but couldn't find anything close and so gave up looking.

A month before the trip I hid the nail clippers and his Alice band (which he always wore), his nails were long which he didn't like so he went pretty crazy, searching everywhere for them. When he finally gave up I passed him an emery board and explained how he could keep his nails trim and so wouldn't need to cut them. He had the idea that if he used it enough he could get his nails short until the clippers turned up. The Alice band is another story. That couldn't have been easier. I simply offered one of my hair bands to wear instead, it was like the Alice band but not zig zag, oh and purple but he didn't mind.

Two weeks before the trip I got Chrissie drunk again.

'Chrissie when you pop into town tomorrow can you get me some things?'

'Sure.'

'Great, look, write them down so you don't forget.' I said, passing him a note pad and pencil.

'Okay ready? I need all of these things in size 10.'

'Size 10?'

'Yeah, you don't mind popping into some women clothes stores and getting me a few things for the holiday do you?'

'Well..'

'I mean you are man enough to buy me some clothes?'

'Of course, okay what do you need in size 10?' He said sternly as though defending his manhood.

'I need a white skirt, a pink skirt, some knickers…'

'Hang on, you haven't given me any details. What kind of white skirt?'

'Oh, you decide, you've got a good eye. Just get me what you think you would get if you were me.'

'Get what I would get if I was a woman.' Chrissie said as he wrote down those instructions.

'So I need two bikinis, you pick the colour. Five bras 32bb. Ten tops, two dresses, some tights, some shorts, three pairs of heels and one pair of flip-flops size 8.'

'You're not size 8…'

'Ssshh, listen… a couple of necklaces, bracelets, earrings, make-up lots of it, you'll know. Nail polish two or three colours. Some hair accessories and another dress make it three more dresses and four more skirts.'

'Anything else?'

'No but as you're drunk I'll put it in your wallet now along with five-hundred dollars for the stuff.'

'Great thanks.'

The next morning his head was thumping and as he left, I asked him to make sure he got everything on the list. He patted his pocket and said 'I may be hung-over but I remember that conversation and I'm a man and therefore can get you your stuff.'

Hours later Chrissie walked in under an avalanche of shopping bags.

'Hi Chrissie. What's all this?'

'Your stuff, you really did want a lot of things didn't you.'

'No I only wanted some more sugar. What have you brought?'

'Sugar? I got your dresses and skirts and bras and everything.'

'My what?'

'The list in my wallet, you asked me all these things.'

'When?'

'Last night.'

'No I would remember but anyway lets see what you've got. I looks like you've been to all my favourite stores Chrissie.'

'I have and I got you these dresses.' He said opening a bag and went to pick up another.'

'But these are size 10, I'm a 8.'

'What, well I got you size 8 shoes like you asked. Here.' He said shoving them at me.

'Wow, nice shoes but I'm a size 5 not an 8. You're an 8 are you sure you're not still drunk?'

'No look on this list. Size 8 shoes and size 10 clothes.'

'This is your handwriting Chrissie. And what does 'Get what I would get if I was a woman.' mean?'

'You asked me to get what I thought would be nice.'

'Well these are nice Chrissie but they would fit you not me and I didn't ask you to get them. But if you want to wear them then I don't mind.'

'Thanks but I don't. What shall I do with these then?'

'Take them back.'

'What and go in those shops again with all the women staring at me like I'm a freak. No thanks. Lets leave them in the spare room for now and we'll do something with them after the holiday.'

'Okay, well I'm just going to unpack them and see if anything might fit me then.' I said, taking them away.

A week before the trip, I got him talking about his body hair and bet him twenty dollars he wouldn't shave his legs, armpits and legs to see what I have to go through. Without hesitation he headed for the bathroom and I was right behind with the new lady shaver he'd brought on his shopping trip.

The night before the trip he packed his suitcase while I was at work but then when he went out for a run, I changed a few things around.

The twenty four hour flight to New Zealand was tiring, the helicopter exciting and when it flew away leaving us alone, the fun began.

'Why don't you go take a shower Chrissie? I'll unpack your things.'

'Okay thanks Zoë.' He said stripping his smelly clothes off and heading for the shower.

He returned minutes later, towel around his waist and perfectly formed breasts out in the open.

'That's so much better.' He said wiping a long wet strand of blond hair from his face.

'Great. You clothes are in that cupboard and those drawers I said pointing.'

'Thanks… Wait, which cupboard?' He asked as he opened the door.

'That one, why?'

'It's full of your stuff. Dresses and skirts and things.'

'No my stuff is in my suitcase here, I'm still unpacking and those are my drawers and cupboard.' I said gesturing to the open drawers half full of bras and knickers.

'Well where's my clothes? The stuff you unpacked?'

'That is it Chrissie in there. It looked to me to be all those things from your shopping trip the other week.'

'What? You mean when I got all the wrong sizes for you?'

'Wrong for me but right for you Chrissie.'

'What? How?' He said, sitting down on the sofa.

'Maybe we should talk.'

'Okay.' He said.

'I understand Chrissie. What you're going through Tara told me about the conflict she encountered.'

'What conflict?'

'About becoming a woman. You don't need to hide it anymore.'

'Becoming a woman. Who? Me? What do you mean?'

'What do I mean? I've seen you change this past year Chris. The hair, nails, your chest. You shaved your body hair. Remember when you asked me if you could wear my dress? I suspected. But then I guess I always knew, I mean it must have been your inner femininity that drew me to you, you know I'm gay right?'

'You were gay. Look I'm not trying to become a woman. My nails are long and shaped because we lost the clippers. I shaved my body hair for a bet. I don't know why I asked you about wearing that dress but I never did wear it.'

'Okay well, you take your time Chrissie. Put some clothes on and just take this trip easy, I know you must have strange thoughts right now, but I'm here to help you.'

'Okay where are the clothes I was wearing earlier?'

'They stink. Look just pick something from your clothes to wear, it won't kill you.'

'Okay but this stays between us ok?

'Ok.'

 

With that he stood up and inspected his clothes. After minute or two of looking back and forth and hesitating he picked out a white skirt and a pink vest top. Then picked up a pair of knickers. He put the knickers on first then the skirt. It fit his hips perfectly. Next he went to put the vest top on.

'Wait aren't you forgetting something?'

'What?'

'A bra.'

'I don't need one Zoë, I don't have breasts.'

'Look down Chrissie, what do you call them?'

'Man boobs. Okay look I'm going this far so I guess I should go all the way huh.' He said picking one out and putting it on. He struggled a bit to clip it, so I showed him an easier way. It fit perfectly.

Next putting the vest top on, he looked like a woman without make-up on. He moved across to look in the mirror and I could see by his expression that he liked what he saw.

'How do you feel? Comfortable?'

'Well in truth it's not that bad and the bra actually takes a weight of my chest and feels almost right.

'I see, well I'm going in the shower myself now.'

'Okay.' He said, walking around and enjoying the way the skirt moved.

The sun set shortly after I got out of the shower and the lodge soon cooled down.

As we stood in the kitchen cooking some dinner, I could tell Chrissie was getting cold in his choice of clothes.

'You look cold honey.'

'I am a bit.'

'Well put some tights and a cardigan on.'

'Tights?'

'Yeah why not. I'm wearing them, they didn't kill me and I'm warmer than you.' I said pointing down.

'Okay, fine.' He said going into the bedroom.

Minutes later he returned with flesh tights on. I was impressed he chose them over the black ones, as flesh went better with the skirt.

'It's pretty slippery on this floor with tights on.' He said.

'So put some shoes on.'

'Oh yeah, good idea.' He said before disappearing into the bedroom.

Returning he wore a pair of strappy heels, perfect with his outfit.

'First time I've ever worn these.' He said, wobbling a bit.

'They're nice and I'm sure they'll feel like your other heels in no time.'

'What?'

'What?' I asked

'I don't know. Look I was thinking maybe I can hike into town and get some more clothes.'

'Hike in, what in those shoes?'

'No in my shoes I wore here. My man shoes.'

'What your flip-flops. Look Chrissie town is miles away, we don't know where. Just get used to it for 3 weeks and then when we get home, it can be our secret.'

'You're right. I guess I better get used to the idea I'm going to be Julie and not Chrissie for the next 3 weeks.'

'Julie?'

'Sure if I had to pick a girls name for myself that's what I would have.'

'Okay Julie. Well if you're Julie then I guess after dinner you should get some make-up on and look like a proper woman.

'Okay. This is truly bizarre, never in a million years would I have thought I'd be spending 3 weeks dressed as a woman with a girlfriend that doesn't mind.'

'Oh Honey, should have said something about this sooner, I would never have minded.'

That night I helped Julie put her make up on. She looked stunning, and instantly I knew I had once again found true happiness, I had the women I wanted once again. We made love that night and it was incredible. The best since Sarah despite certain differences.

The next morning, I woke to find Julie stood in a bikini wanting to go swimming.

'You could just wear the bottoms you know.' I said checking her commitment.

'I know but I find that bras give me much needed support.'

'Tying his hair into a high ponytail she led the way.'

After the swim she saved her legs and put a summer dress on. She looked stunning.

That day I taught Julie how to sit properly, how to walk and talk. She was always a bit hesitant but I could see she was enjoying it. After 6 days, we did some laundry and washed Chrissie's collets and t-shirt. I have Julie the chance to take a day off and she took it. I was devastated but hid from him. Walking into the kitchen he wore no make up, his dangly ear-rings were replaced by studs, he wore the shorts and t-shirt but I could clearly see he still wore a bra and his hair up in a high ponytail.

'You don't have to wear the bra Chrissie.' I said.

'I know but it's more comfortable that way.'

'Okay.'

 

That night when it became dark, I could tell his legs were cold and he was missing his tights.

'You can wear tights under your shorts Chrissie. I won't mind.'

'I guess so, it's not very manly is it.'

'Nor is freezing to death.' I said watching him get up and head for the bedroom. I could hear the click clack of heels before I saw him return wearing flesh tights and heels and his shorts and t-shirt. I couldn't help laugh as it didn't look right.

'What?'

'Just put a skirt on Chrissie and stop all this macho stuff, it's okay I accept you and love you.' I must have said what he wanted to hear as he disappeared and fifteen minutes later Julie appeared wearing a long sleeve dress.

'Hi Julie. I missed you.'

'I missed you too.' She said.

 

After the next laundry round Julie didn't even think about trying Chrissie's clothes again. Nor the one after that. Before we knew it Julie's three weeks were nearly over. She had come on so well. Her voice was soft and feminine at all times, she walked with grace and sat with posture. She had mastered make-up and even had some favourite outfits. We had connected so well and I couldn't control myself when I asked Julie to marry me and she said yes.

The sad final day arrived. Julie sat on the bed her towel wrapped around her body, staring at two piles of clothes, hers and Chrissie's.

'My passport says male, so I guess I should say goodbye to Julie. I want you to know Zoë, that I have enjoyed being here, although I hadn't asked for it, at least I don't think I did. Maybe we'll meet again.'

'Tuesday when we get home?' I asked, my voice breaking up.

'Well, I had thought that you'd prefer Chrissie back, he does.'

'Okay, love you Julie.' I said as she unwrapped the towel and he picked up his shorts. Although I saw a glimmer of hope when he put a bra on before the t-shirt.

The flight took forever. I sat wondering what life would be like again with Chrissie. Chrissie sat with posture. Just before landing I touched up my make-up. Chrissie watched me with an itch to do something with his appearance, twisting his hair into a bun and letting it drop.

We got home. I unpacked and Chrissie went through his wardrobe looking for some fresh clothes. He picked a pair of jeans and a shirt, still wearing a bra beneath. That evening we sat watching TV, both of us filling our nails.

The next morning, Chrissie was already up looking in the mirror, watching himself putting his hair up into different styles with clips and grips. I watched for a while not wanting to distract him. Then I moved about and groaned making him thinking I had just woken up.

'Morning honey.' I said, seeing clips in his hair.

'Morning Zoë. Look I was wondering.'

'Yeh.'

'Just for this morning would you mind if I wore a skirt?'

'Sure, why?'

'I just really feel the desire to wear a skirt, I think it's a skirt day.'

'Okay.' I said watching him quickly pick out a dark skirt, knickers and patterned tights. On top he wore a bra and shirt, leaving his hair clipped.

'Looks nice. You know you don't need to ask.'

'I know but it still feels strange, you know a man wanting to wear a skirt.'

'Well accept it, it doesn't need to feel strange honey.'

Later that day, I noticed he'd put some mascara and foundation on but I didn't say anything. The next day he was back in jeans but complained that they didn't fit so well, so he put a skirt on.

This went on for the next week, as he would either start in a skirt or start in men's trousers and then revert to a skirt. I hit my breaking point and came back from town with some women's jeans for him, knowing they'd fit better. He didn't even question what gender they were for and happily wore them straight away, commenting on the good fit.

Then after a fortnight of skirts, jeans, women's hairstyles and occasional make up it happened. I woke to find Julie sleeping in my bed. As she opened her eyes, her voice was soft as her skin.

'Thought I'd pay you a visit.' She said.

'Wow, lucky me.'

'Well I missed my clothes, having to live like a man for weeks.' She said.

 

That day she was stunning, her make-up was different and better than Chrissie ever managed, her dress and shoes looked great. She was amazing, my fiancée.

'I was thinking about sticking around for a while again.'

'Really?'

'Well I had so much fun during those three weeks, I was thinking of trying 3 months this time.'

'Three months? Really?'

'Yeah and who knows, if I can keep Chrissie hidden away for a bit longer then maybe I should become a complete woman.' She said gazing in my eyes and pushing some hair from my face.

'Wow! I love you Julie.'

'I look you too Zoë.'

  

  

  

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