As she walked past my desk, Jade gave the cheekiest of winks and flashed one of her knowing grins. It both infuriated and excited me. She was the most beautiful woman I'd met. Perfectly proportioned and always dressed in the sexiest of clothes, her "Power Dressing" look was tailored perfectly to show her exquisite rear, endless legs and full breasts. She always wore the highest heels that made her tower above me despite being my height. I gazed longingly after her as she swivelled her hips around the cluttered office desks.
"Careful partner" teased Dan. "Better close that mouth of yours before you catch something." He threw some crumpled paper, knocking me out of my reverie as it clattered off my forehead.
"I was just thinking about work," I replied, knocking the paper in the bin. Dan chuckled, his round belly wobbling as he shook his head and winked salaciously.
"Yup, sure thing Owen. Thinking about something that's for sure!"
"Haven't you got a meeting now with Jackie?" I asked, knowing full well he was running late. His eyes shot to the clock suspended above the door, and with a loud curse, he grabbed his jacket, and sprinted towards the lift.
With a wry chuckle, I went back to my work. I'd been working in the Law Firm now for several years and found it incredibly boring, but it paid well and the chances were good that I'd be partner by thirty. Besides, working in the same office as Jade made it all worthwhile! For the rest of the afternoon, I filed my hours for all the cases I'd been working on when Dan slumped down beside me with a heavy sigh.
"What's up" I asked, glad to have some distraction from my work. He shook his bald head and sighed again.
"They let me go. Said there'd been a policy change and that the firm was headed in a new direction and one that excluded me." I was stunned. Dan had been part of the furniture here since I'd started and he billed more hours than most people here. The Water cooler gossip had him up for Partner within the next year.
"Christ Dan," I gasped. "What sort of change in direction? They can't just sack you like that!"
"It's a law firm remember, I'm sure they've got all their bases covered. They're getting rid of all males and changing the firm to females only, working with females, for females, or some such crap. New ownership, new policy, bye bye old me." He looked at me with sad eyes as I digested this news. "Sorry pal. Jackie's asked me to send you up. Listen. I've got plenty of contacts. I'll find work no worries and I've got a nice pay-off. If you need a job, just look me up, you hear?
I nodded, still too shocked to take this all in.
"Yeah, thanks Dan. I'll be in touch." I picked up my jacket and fed my arms through the sleeves as I drifted towards the lift as if wading through thick fog. It seemed so unreal. One moment, I was thinking of partnership, the next, what my next job could be. The lift took an age to arrive and as if in a dream, I made my way to the lead partner's office. As I passed her secretary, she waved me in and shut the door behind me. Jackie was leaning against the desk, dressed in a tailored skirt suit and killer heels that made her seem all the more dominating. She had sensual lips and a cleavage that threatened to spill out from her silk blouse. She was old enough to be my mother, but exuded a sexual confidence that made me forget all about that.
"Owen. Please sit down, and shut the door behind you." I did as ordered and sat in a plush chair that was designed to make the person feel safe and comfortable, but made you sink so deep, you always had to look up at Jackie. She sat down behind her desk and held my gaze for a long time. Finally she spoke.
"You've worked her a few years now, haven't you Owen?" she asked. I began to speak, but she cut me off. "I've worked with you on many cases and your work has been excellent. You're a rising star within the firm and one of the best we've ever had." I felt my anger rising. Why was she saying this if she's going to sack me? I thought. "But there's a problem. The firm's been taken over, and has a change of direction." Here we go, I thought. I steeled myself for the cut, but what came out was something entirely unexpected. A sly, almost cruel smile, spread on Jackie's lips.
"It's become a woman only firm. In one month, our new owners will arrive from America and will spend six months shaping this Firm into their image. Then they'll be gone." She leaned back in her chair, her eyes running themselves over my slight frame. I'd always been a little small for a man, and she made me feel acutely aware of it now. She nodded to herself as if confirming something she'd long suspected before continuing. "I'm going to sack you now, and in one week, I'm going to re-hire you on three times your wages, more than anyone your age could possibly hope to get"
"I don't get it," I replied. "Why sack me then re-hire me? I'll still not conform to policy." I barely held my anger in check, but it soon turned to shock.
"Because I'll hire you as a woman." She replied simply, as if it was the most obvious thing in the world. Shaking with rage, I stood up, told her I quit and strode towards the office door. With lightning speed, she dashed to the door and barred my path.
"Out of my way," I snarled, and made to push her away. She held her ground and spoke rapidly.
"It'll only be for six months," she whispered, so that her secretary wouldn't hear. "You'll be paid more than you can dream of, I promise I'll make you partner when this is done, and when our new owners have gone back home, you can go back to being Owen again. Nobody will know." I gave a snort of derision.
"I think people will notice if I suddenly turn up in a skirt!" I whispered back. I don't know why. I should have shouted it back and publicly humiliated her, but the thought of all that money and an easy path to being partner was hard to resist.
"Face it Owen!" replied Jackie. "You're a small guy. Give me one week, and I can make it so that nobody will be able to tell. We both know you're a loner and that you have no family – you could pull it off no problems. I don't want to lose such a valuable asset as yourself!" I shook my head.
"This is crazy! It'll never work!" Jackie smiled and gave a deep, throaty chuckle.
"It'll work," she whispered, almost huskily into my ear. "If it doesn't, I'll pay you four years worth of salary at your current pay scale and make sure you get another job within a month. Come on? What's to lose?"
"How on Earth do I go about starting this?!" I asked.
And that was it. That was the moment. As soon as I changed tack from "NO way" to "How can it possibly be done?" she knew she had me. She smelt victory, and that was how I cleared my desk, said my farewells, and went home to pack my bags. I was going to stay at Jackie's and she was going to teach me how to be a woman for six months.
"Rise and shine Louise!" cried Jackie as she woke me up by opening the curtains with a regal swish. Even though it was the weekend, she was immaculately dressed in a long, figure hugging dress and knee high boots with killer heels. She looked amazing and I could feel myself becoming aroused, lying in bed. I'd stayed the night before, and after a few drinks had become too sleepy to be of much company. Jackie had shown me to my room where I would stay for the next week as I underwent "Training" as she called it. I'd move back to my own place after my training and already missed it, with its huge TV and collection of Blu-Rays. Jackie chuckled as she saw my arousal lifting the sheets.
"Not so little after all," she said, amusement crinkling her eyes. "We can't have that giving the game away now can we Louise!" She walked out of the room, ordering me to get dressed. "Come on Louise, we have a lot to do!" I wasn't sure about the name, but dragged myself out of bed and went to get some breakfast as Jackie outlined my day.
The first thing she did was take me to her local salon, where she left me for a few hours as the hair on my face was electrolysed, any other hair waxed, my eyebrows shaped, ears pierced and my nails painted. The girls there thoroughly enjoyed working on me and I soon relaxed. There was no point fighting this – I'd already agreed to do it, so I decided to treat it as an adventure. I'd never been particularly masculine, and to be honest, the thought of being a woman for the next six months truly didn't bother me as much as I thought it would. As Jackie had pointed out, I was a loner and would simply be sat at home watching some film of shooting stuff on my XBOX. At least I was out and about! Jackie came to pick me up when I was done, and marvelled at how smooth my face looked.
"You know, we may just pull this off after all!" she said, eliciting some chuckles from the girls who'd worked on me. "Come on!" She cried. "Time to get going!" She made another appointment for me to come back in two weeks before driving me back to her house. My whole body tingled, and the baggy jeans and shirt I wore seemed to scratch at my soft skin. As soon as we returned, Jackie ordered me into the shower, telling me to use the shower gel provided and then use the cream by the sink over my whole body. I did as ordered, marvelling at how different everything felt without hair. The water and feminine soap cascading from my smooth skin felt like nothing I'd experienced before. Stepping from the shower and into my room, I saw that all of my clothes had been removed whilst I'd been washing. Jackie sat on the bed, tutting slowly.
"Louise, that's no way for a lady to wear a towel. Here." She stood up and whisked the towel from around my waist. I gasped, too shocked to protest as she revealed my cock with business-like efficiency and wrapped the towel around my body, tucking it under my arms. "Like this," she said. "There's a silk kimono behind the bathroom door. That's yours to use." She took my hand and led me to a cupboard that took up a whole wall. "Now, let's introduce you to your wardrobe. I took the liberty of ordering the clothes I think you'll need. I'm going to employ you as a successful woman, so you'll need to dress the part." She swung open the doors to reveal a huge walk-in wardrobe crammed with what looked like hundreds of clothes, of every shape and colour. One wall was covered with shoes and I gulped as I saw that none of the heels were smaller than four inches, most looking like five or six. Jackie led me in. "Last month, you spotted a loophole in our client's contract that saved him half a million pounds. He gave us a generous tip, which I've used here." She began pulling clothes from the racks and holding them up to me, whilst chatting away rapidly, almost to herself. I followed in a daze. "You'll notice theses clothes are very feminine. The more feminine you dress, the more feminine you'll act. I guessed your size, and I think I got it just right! These draws have your underwear, this one your fake breasts and body shapers, this one..."she pointed at a locked cupboard. "...well, we'll get to this one another time!" Finally settling on an outfit, she dragged me out and placed the clothes on the bed, still talking scattershot, before ordering me to take off my towel. I stupidly complied as she picked up a satin full bodied corset with suspenders and stood behind me to put it on.
"This will give you a feminine shape. You probably don't need it with your body shape, but it'll make your hips look bigger and make you walk and sit as a woman would. You should wear one every day until your gait becomes second nature. This has metal boning and will feel uncomfortable at first." She asked me to lean forward as I buckled the front and she tightened the cords at the back. Stars clouded my vision as the corset squeezed my body, pushing the air out of my lungs.
"Too tight!" I yelled, making Jackie burst out laughing. "I can't breathe!" I gasped.
"You'll get used to it," replied Jackie. "Within a week, you'll be wearing one a few inches narrower and you won't even notice. You'll need to breathe differently. Less from your stomach as men do. Now put these on." She handed me some stockings and I sat down as I rolled them up to put over my legs. The corset made it difficult as I could barely bend my body to lean down. I felt a surge of adrenalin as I pulled the stockings over my smooth skin, and felt my cock begin to pulse with lust. They felt so soft and sensuous. Jackie helped me attach them to the suspenders hanging from the corset as I struggled with the ones at the back. I could see her smiling at my erect penis and blushed with embarrassment. I stammered an apology, which she waved away.
"Wear this, you can tuck yourself into that and keep it tucked away." She gave me some lacy knickers with a pouch inside to tuck my cock in. I managed to get flaccid enough to use it whilst Jackie helped me into a bra. "The pouch should keep any excitement hidden and stop you scaring our clients off!" Jackie was clearly enjoying herself as she presented me with a pair of silicone breasts. "Touch them," she ordered. They felt and looked so real, and I happily let her show me how to wear them in the bra and how to use them without a bra, gluing them to my skin with a natural adhesive. I was getting used to the corset now and gazed in the full length mirror at how feminine my body looked. The corset gave me an hour glass figure, the stockings smoothed away the musculature of my legs and the breasts gave me a fantastic bust – not too big so as to be obvious, but Jackie had certainly made me well endowed! My crotch area was completely smooth and it was unnerving to see, but also curiously exciting.
"Now for shoes!" Jackie stalked back into the walk-in cupboard and came back with a pair of court shoes with four inch stiletto heels. "We'll start you off with these, before you wear the taller ones. After all, you'll be walking round the office all day, and then catching a tube home so you'll need to be comfortable in them." I felt a brief moment of panic at the thought of using public transport or actually going to work and trying to fool my ex-colleagues. I made a mental promise that I'd leave after two days if I couldn't get it right. There was no way I'd ridicule myself, possibly ruin my chances of getting a job elsewhere if word got out. I sat on the bed as I put the shoes on, my stockinged feet sliding smoothly in. As I stood, I almost fell over, only for Jackie to grab my arm.
"Woah there Cow Girl," she called. "Take it slow. Walk slow steps, keep your back straight. The corset will make walking in these easier." I started walking around the room, quickly getting used to swivelling my hips and putting my feet directly in front of each other as a woman would. "Excellent! You're a natural!" encouraged Jackie. "Now put these on." She held out a short, black skirt and a purple satin blouse. She told me to put the blouse on first and I shivered with joy as the soft satin stroked my skin. Jackie noticed and smiled again, knowing I was starting to enjoy this. I sat on the bed to put the skirt on. It was pretty tight and forced my legs closer together. Walking anywhere's going to take a while! I thought as I stood up. The skirt was high waisted and started well above my belly button before coming mid way down my calves. The soft material hugged my body and showed off my hour glass figure. I started walking to the mirror, but Jackie held me back.
"Make-up first hon." She showed me to the dresser and sat me down in front of a mirror. She spent the next hour teaching me how to put on my make-up. I soon realised that it was an art form, yet Jackie explained it as if she was born to be a teacher. I gazed in wonder as she applied the make-up and transformed me. I'd been a fairly good looking man, but she made me positively sexy, lining my eyes to make them seem bigger and making my lips fuller, before softening my jaw line.
"Now close your eyes." I did as ordered and heard some rustling in the background as she took out a wig and placed it on my head. As she shaped it, she told me how to look after my wig. "I've bought you several, as they'll get a lot of use, but you should really grow your own hair. It'll make life much easier. There. All done." She took my hand and led me to the full length mirror before allowing me to open my eyes. I gasped in astonishment as I beheld the woman in front of me. All my doubts were blown away as I saw how real I looked. I didn't recognise myself. I had long, shapely legs, a fantastic figure and Jackie had done a wonderful job on the make-up. I felt something click within me and knew then that my life would never be the same again. I'd never considered cross dressing before, yet it felt so right now. All the loneliness and sadness I always carried was filled with this moment and I felt tears well up. I felt complete.
The next few days passed in a blur. Jackie had taken a some time off and tutored me all day in how to walk, how to speak, eat, get in and out of the car – the little things that you never think about and tiny mannerisms that separate the genders. She had been right about the corset and I was already wearing one that narrowed my waist even more. It had begun to feel like a comfort blanket that was only slightly uncomfortable! I got used to the shoes and wore five inch stilettos as par for the course. Soon I was acting as if born a woman, and I could feel the last vestiges of my masculinity fading away. I embraced Louise knowing that I'd get Owen back after six months and all would be fine. That's what I told myself anyway. As a result I never mourned his loss. I was too busy spending all my free time in my cupboard, trying on all my clothes and getting used to walking in skirts, dresses and skin tight jeans. The locked section intrigued me, but I was sure that Jackie would reveal it soon enough. I practised my make-up, wiped it off and practised again until I had it as good as Jackie did. She was an excellent mentor and seemed to take delight in my progress. A few times I caught her looking strangely at me, a look I couldn't penetrate, but shrugged it off. She'd let me know if there was a problem. She'd been my boss for so long and was so used to telling people what she thought, I knew she'd let me know if there was an issue.
"You're coming along so well Louise," said Jackie one evening after dinner. We were sharing a bottle of wine and playing cards. I was wearing a roll neck figure hugging jumper and a tight leather skirt complemented with a wickedly heeled pair of knee high boots I'd fallen in love with.
"Thank you Jackie," I replied. My voice had never been particularly high, and with a little coaching, could pass easily as long as I didn't shout! She smiled back.
"I'm going back to work tomorrow, but will be sending Jade round with some files for you to work on. I know you won't be starting for another few days yet, but I thought you could get started on a big case coming up." I gulped nervously, my heart beating heavily in my chest. Jade! Jackie saw my fear and grinned.
"You'll be fine love, she knows what's happening and is excited to meet you." Anger surged through my veins!
"You told her?!" I asked, incredulous. Though nothing had ever happened between us, and nothing probably would, the thought of her knowing shamed me. Jackie laughed harder, making me even angrier and throwing the cards down in disgust.
"Yes I did! If anyone would understand it would be Jade."
"Why?" I asked, disgruntled. Jackie leaned forward, laying a Royal Flush on the table and grinning mischievously.
"She's a pre-op. It was her idea to get you to do this. Her that helped me get all your clothes." I gasped in shock. It was too much to take in. She'd seemed so perfect a woman. Whilst I was digesting this news, Jackie stood up made to leave. "She's looking forward to seeing your progress and working with you tomorrow. Don't worry. Only I know at the office that she's a transsexual. She won't tell anyone about you, the same as you'll say nothing about her." She kissed my forehead maternally and with a soft Goodnight, went to bed, leaving me in a state of shock.