tagTranssexuals & CrossdressersNew Year, New Career

New Year, New Career


The new year came round very quickly. Christmas was seemingly over as it begun. Auntie had gone home and the infamous Christmas Day dress my dear Auntie had given me hung in my wardrobe lonely amongst my male clothes like a fish out of water. Mum and my sister hadn't mentioned it again and it was with a tinge of sadness that I looked back at the events of Christmas Day. I loved dressing as Rosemary so much I desperately wanted to relive the experience. Uncle George hadn't pestered me as I thought and mums friends Trish and Dave hadn't been in touch about the job they offered. Perhaps it was the Christmas mulled wine talking? Why should they offer me a job? I'm sure they where just being kind. With no retail experience I surely wasn't qualified to work in their fashionable boutique. Their store had a considerable reputation, not short of eager young staff. Besides did they really expect me to dress as a pretty young lady again.

After the initial shock at Christmas I deeply enjoyed dressing as Rosemary and regretted having to take the dress off. A couple of times when I had the house to myself I got Auntie's present out from the closet and fondly fingered the sumptuous fabric but never had the courage to try it on again terrified I might be caught.

The past events seemed little more than a dream. A gorgeous fairy-tale dream far removed from the harshness of modern life. Then out of the blue...

'Guess who I met for lunch?' Mum said the other day. ' I shrug.

'Trish and Dave from "Debut" the clothes boutique.'

I look up from my magazine, a stab of excitement shoots through me, my stomach to flutters like a butterfly.

'They needed to know if you still wanted to work at their ladies shop after the holiday. Apparently they are short staffed.'

I look at mum nervously knowing what I wanted to say but unsure if I should. Mum sensed my apprehension.

'Don't worry pop-it, I said, yes for you.'

She grinned like a Cheshire cat but sensed my nervousness. 'Don't fret you'll be fine. Its so kind of Trish and Dave to help you out. You haven't had a job for six months and we could all do with the money.'

I nod but my brow creased like a freshly ploughed field with worry. 'Of course they expect you to fully dress the part but why worry you did such a good job of that over Christmas you'll be fine and its not as if they are short of stock.' She giggles slightly and touches my arm comfortingly.

My step-dad, Mike overhears the conversation and walks into the room. 'It's about time you did something for this family. I'm not sure if boys should dress as girls but if it gets you off your arse I won't complain. Just don't expect me to give you a lift to work.'

'Don't be so hard on the lad,' mum says comfortingly. 'He's finding himself and if this is what he needs I give him our support.'

Mike shakes his head to dismiss the thought and leaves the room. 'Don't worry about him, 'Mum said' He will come round once he sees you back in a dress. He's a sucker for a good pair of legs.'

I smile reassured slightly.

'Everybody has their thing. Its all about working within your boundaries. Anyhow... You're to turn up on Tuesday at 8.30 as Rosemary.' I look concerned. 'We thought that would be easiest for you. Turning up as Rosemary to start your day afresh rather than having to change at the shop. The transition might be rather too much to cope with.'

I didn't know what to say. Half of me wanted to refuse but then I seriously had to find a job and start pulling my weight. The other half had fallen in love with the idea of becoming Rosemary and working as a girl. My good old Auntie was right I did want to dress and be like a girl. But who was I kidding? Where they all just pulling my leg and spinning an elaborate and cruel hoax? I hoped not.

Mum seemed to think not and when Trish and Dave dropped a huge case of clothes off at the house on the Friday night it all sounded very genuine. Fortunately I was out.

'Have you looked through your new pretty things,' Mum asked deliberately emphazing the words "pretty" and "your". I had. They where indeed beautiful. A co-ordinated mix of various types of skirts, dresses in pretty prints and an assortment of coloured tops. I loved the jacket in butter-soft leather, the waistcoat and the rock-chick T-shirts, even the denim mini skirt. They where all brand new. I guessed there was at least seven complete outfits so I could wear something different everyday if pushed. Not only had I had a good leaf through them I'd tried most of them on within the hour like an excited teenager. They all fitted perfectly. Just like Auntie, Trish and Dave had guessed my size perfectly even the shoes where perfect. Plus I had folded and hung everything neatly in my cupboard in case any of my unaware friends saw my new femme wardrobe. I had initially made room amongst my male clothes but thought it all looked ridiculous so I cleared out some draws and gave them their own special space.

'You'll need a few things I'm sure. We can buy them tomorrow if you like. Perhaps you can make a list. Your sister can help. I'm sure if you ask her nicely she will lend you some accessories.

Julie was only too pleased to lend a hand. Sure enough somehow she had heard about the job and the delivery. When she was home from work she was eager to see what I had and mum had to step in to stop her squirrelling away some of my new things.

Like two young sisters we rifled through my new clothes and chatted excitedly about my new job. She wanted to see them on and try them on herself so for the first time in our lives we stripped down to our underwear and dressed each other like Barbie dolls. We had such great fun. Mum came in when she heard all the laughter and together they wrote out a shopping list of considered essentials. It was mainly lingerie as x said she would lend me make-up. The following day mum and Julie took me shopping. We bought everything on the list. We shopped like sisters. We avoided the high street multiples and though I couldn't afford it Julie helped me choose some beautiful lingerie from a tiny independent shop. She choose me three sumptuous padded bras, five pairs of fetching panties, four pairs of sheer tights and two pairs of seamed stockings and one sexy suspender belt. Mission successful I bought them both a coffee but had to stop Julie from getting my purchases out in public and announcing her intention of dressing me up.

'Happy?' mum asked. I was and she knew it. 'Anything else before we head home,' she asks. I grin. I had always wanted to wander the isle at the chemist choosing make-up and often eyed enviously the young girls who did so. I pleaded with them to take me. I wish they hadn't it was so frustrating. I wanted to test the shades of foundation, apply sample eye-shadow and coat my lips with lipstick but dressed as I was I would have caused a considerable commotion - life I thought is so unfair.

'You'll have to come again as Rosemary,' Julie said testing a lipstick. Mum laughed opting to buy a few items herself.

On the Monday night I got out my work outfit just like my sister and hung it on the door ready for the next day. From my new wardrobe I choose my favourite cream dress with three quarter length sleeves and a cream crochet cardigan, some of the lingerie we had bought the day before and some cream high heels. Julie was just as excited. She came in and helped me moisturise, wax and pluck until I was as smooth as the day I was born. She brushed my hair and repeatedly told me how beautiful I was. When my hair was shiny and straight she gave me a sumptuous pink and lace halter-neck teddy with matching panties that were adorned with beautiful bows. 'Call it a good-luck gift,' she said.

I was delighted.

'Ladies love lingerie. Why don't you sleep in it?' she suggested toy-fully playing with her own hair, 'so you can acquaint yourself with the role.'

I immediately stripped and slipped the panties on. They felt gorgeous, light and sensual. Next the teddy transformed my body making me feel sexy and cosy not trussed up like a Christmas Cracker as I feared. She was right I felt soft, erotic and incredibly feminine as if born a girl. She then did something she hadn't done for years. She kissed me lightly on the cheek. 'Goodnight Rosemary,' she said with a wink. 'Sweet dreams.'

Sleep that was a joke. I hardly slept a wink. I was as excited as a child on Christmas Eve. I slept fitfully all night my mind restless and my cock so swollen I thought I might burst.

I eventually rose at seven with a massive erection. I caught my reflection in my mirror and saw a dishevelled girlish figure in a pretty teddy with a cock poking out of her panties. I shut my bedroom door, dropped to my knees, lifted my teddy and quickly relieved myself, blowing almost immediately. I made an incredible mess in Julie's panties but when tucked away my now flaccid cock was barely visible.

I dressed in a dream like state hardly able to comprehend that I was going to work as a young lady. I showered and dressed in fresh panties and a beautifully padded bra. I then slipped the tights up my legs and stepped into the dress. It was lined so I didn't need a slip. I sat on my bed as Julie waltzed in, already dressed, and offered to apply my make-up. I agreed. It was just like Christmas again. She lent me a delicate bracelet and an enchanting necklace with a tiny swallow, heart and star charm. She even lent me a watch with a delicate strap and a few dress rings. Together they made my neck look slender, my wrist tiny and my fingers long and slender. I felt perfect, like a Fairy-tale Princess. We had thought of everything.

Excitedly I slipped my shoes on and my cock immediately began to throb yet again. Julie noticed instantly and suggested I sort it out before going downstairs. I was horrified. But more was to come when Julie locked my bedroom door and offered to help. I didn't know where to look as Julie, without an invite, lifted my skirt and tugged my tights and panties to my knees. In a trance like state I took my hem from her as she bent and massaged my throbbing cock between her soft hands.

'This should be some handsome hunk' she chuckled yanking my cock as if uplifting a root. 'not me. Imagine that Rosemary - some beefy guy all smitten with pretty you. I'm sure you'd be quick to let him have his wicked way with you. You'd like that wouldn't you?' I was speechless but using my cock in her hand as a crude lie detector she could read my mind like a book. My cock twitches uncontrollably as Julie pulls me faster and tickles my balls like a professional. 'Oh,' she crys, 'I bet we look like a couple of hot lesbians,' And at that point I emit a long gurgling moan. 'Yes,' she says again, 'two pretty girls pleasing each other before work. Sounds good huh?' I nod and Julie looks me in the eye and licks her glossy lips. That was the final straw and as I buck and writhe under her expert hand I explode and for the second time that day spurt my excitement. A broad smile spreads across her face. 'Good girl,' she chimes as if I had just given birth to a child. I grin stupidly aware that I was becoming very indebted to my sister as she milks me dry of any remaining masculinity into a tiny white tissue.

'All done,' she said giving me the sticky tissue with a wrinkle of her nose and without further a do she slid my panties back over my now flaccid cock, popped it between my smooth legs and replaced my tights. I dropped my skirts and Julie brushes them down to ensure I was well hidden. I was now sore as if rubbed by a cheese grater but as limp as a wet paper bag but my groin now had a more pleasing feminine bulge. Julie flashed me a knowing glint and in celebration skipped around me squirting exquisite perfume from a tiny bottle. Its like magic as a canopy of flowers falls like confetti through the air. I spin on my heels inhaling the gorgeously feminine fragrance. I felt like a star ready to perform. A true dream princess.

Downstairs mum was waiting patiently for me to appear.

'Doesn't he look hot?' Julie says as I skip into the kitchen and proceed to parade around the table flicking my skirt this way and that. Mum smells my perfume and nods.

'Your legs are so slender, your waist so narrow and your breasts so curvy. How did you manage to look so amazing?'

'Julie helped,' I say gratefully, carefully folding my skirt under me, sitting down to eat.

Mike, my step-dad entered the room alerted by all the commotion. I shuffle awkwardly on my stool as he stares at me in disbelief.

'Get up, Rosemary,' Mum sings, 'show Mike what Julie's done.'

Nervously I stand and perform a delicate spin on my heels so my dress spirals outwards and he can get an all round view. The room is filled with the sound of my nylons and skirt rustling and my heart thumbing

He's almost lost for words. 'You look amazing he says gazing at my long legs. 'I never thought you'd hear me say it but you look absolutely gorgeous.'

I spin one more time before sitting back down pleased with his reaction. I didn't expect him to approve as we had never really got on. He was a mans man and he never appreciated having an effeminate step son. I grin proudly as he kisses me on the cheek careful not to smudge my make-up before leaving for work.

'Well,' mum says, 'that's a turn out for the books. It looks as if I may have to watch you or you'll be catching the eye of all the men round here.'

I want to tell her to shut up but instead I giggle girlishly and Julie and Mum exchange knowing glances.

After I had eaten a small bowl of cereal, Julie gave me a handbag already filled with what she considered female essentials. 'They will get you through the day,' she said. Mum then gave me a hug as if an astronaut leaving the ship to walk on the moon. 'Do you want me to drive you to work?' She asked before i could look inside the bag.

'Thanks,' I say but I've got to face the public and get used to walking in these heels at some point.'

'That's my girl,' mum says and we both look close to tears.

'You won't disown me, mum,' I say. 'You do approve don't you.'

Mum glows like the sun. 'Of course I approve. Whatever makes you happy. And I told Auntie about today. She's thrilled and sends her best wishes. Oh and she's looking forward to Rosemary visiting her at the home too so be a love and don't forget. You do owe her that.

Stepping out the front door was far harder than I imagined. Mum had to push me over the threshold and then the first tentative steps where agony. Dressing as a girl within the secure walls of our house was a totally different experience to being outside in front of everybody.

Andy our postman walked up the drive and gave me a cheeky wink before handing the days letters to mum. 'Good morning gorgeous,' he says as he slips past completely unaware who I was. I blush and look at mum who's beaming like a proud parent.

'Go,' she says waving a hand, 'before you stop the traffic or if you're not careful you'll be late on your first day.'

I wave back, glance down at my feminised form and rub my knees together. The soft sheer tights gently caressing my knees is delightful reminder as of my heavenly state. I feel beautifully girlie, I feel as ready as I could ever be. My adventure had begun.

I had walked to the high street thousands of times before but today every dainty step seemed like a new leap. Like a stranger in a new town I carefully minced along the pavement swinging my new handbag. I saw so many old things in a new light as if wearing rose tinted spectacles. I tried to blend inconspicuously into the background but my heels clicked loudly, my nylons rasped and my dress swooshed with every graceful movement of my body. I was grateful for Julie's old raincoat as it was cold but finishing just below my hips it did nothing to cover my long slender legs. I hoped not to see anyone I recognise as I attracted quite a few stares from other pedestrians and even passengers in cars, both male and female yet I hadn't the confidence to be flattered or horrified.

The fresh morning air penetrated to the bone and I was thankful to be wearing tights. Even though the morning wind whistled round my legs and up my skirt like a chimney. I was quite thankful for this as it kept my cock cold and placid. I found the whole experience exciting and feared my hidden cock may give the game away.

The short 30 minute walk took nearly an hour mainly because of the high heels. I simply wasn't used to them, swinging my hips or taking such delicate steps. I hadn't realised how restrictive the dress was or how wide my step was normally. But I loved the restriction. In fact I loved every facet of my new pretty attire. You would not get me complaining about wearing tights or stockings, balancing in heels, wrapping a bra round my chest or hanging a dress off my shoulders. I positively loved the feel of soft silk and lace. The restriction a skirt imposed on me just helped remind myself what I had become. I wanted to be a girlie girl, a high maintenance follower of fashion.

By the time I reached the shop, the high street was busy with early morning tradesman and I was relieved to find the door open.

Trish greeted me with open arms as I entered and gave me a welcoming hug. I heaved a sign a relief.

'How are you?' she's asks, 'Did you find us OK? Did you walk or get a lift? And do take your coat off. Dave and I have being dying to see you again.'

I stood before her open mouthed unable to answer a single question as she fired one after another. I felt like a new schoolgirl at her first day at school standing in front of her form tutor. I grinned stupidly and she spun behind me helping me off with my coat. I fumble with my handbag as she slips it off my shoulders and I'm soon parading round up and down the shop like a catwalk model swinging my hips and tossing my hair just as Julie had shown me. Trish was delighted.

'Oh my goodness,' she shrieks, 'you look fabulous, far more beautiful than I can remember.' I blush and attempt to flutter my eyelids.

'We did wonder if you would have second thoughts. You looked so good on Christmas Day in the dress your Auntie bought for you. I knew there and then that you where better suited as a girl... But,' she sighed, 'it's a brave step and I was never sure you'd take it.'

She walks around me staring at her clothes on me as if inspecting a dressed mannequin model. 'but I'm so very glad you did.'

She then proceeded to give me a tour of the shop. She showed me the store room and tiny back office. She showed me wear to put my coat, where the toilet was and how to make a drink in the tiny kitchen. Apparently Dave was out and rarely worked in the shop preferring to handle the ordering and administration from home. All the time she talked to me as if a young girl and it wasn't until a few minutes before opening did she turn serious.

'Look, Rosemary love, I don't want to but it has to be said but while your working for me you are to look and behave like a stunning girl. I will call you Rosemary and expect you too behave accordingly. I'm sure I need not remind you that we are a high class ladies store and my customers may not appreciate you being here if they knew your true masculine identity. And if I find you smirking or laughing at any customers or merchandise I will have no hesitation about sending you home. Is that clear?' I nod with agreement. 'I just hope you won't get embarrassed seeing semi naked women or handing clothes and needless to say you must keep that under control. 'She pokes a manicured finger between my legs as if with disgust and I nod with a tiny grin. 'As far as I'm concerned when you're here as Rosemary you haven't got one of those... things - right?'

'Right,' I say blushing and as if it had ears I feel it twitch so as not to be forgotten.

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byTomsparty© 4 comments/ 80862 views/ 11 favorites

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