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Trapped Belladonna [Author's Note: Partially inspired by a caption made for me by Deementia.] I smiled as I slowly brought the pantyhose up my smooth legs, delicately unrolling it with my well practiced ease. The smile was partly the result of the feeling of the hosiery, but another part of it came from knowing that everything was falling into place. I had finally reached a point where I was willing to expose my secret to someone I knew. There was nothing holding me back after my wife divorced me. That was a blow emotionally, but, at least, the judge largely sided with me, given my wife's decision to leave me for another man. The adulterous ending to our relationship, together with a solid prenuptial agreement, had helped to limit my financial obligations to her and left me with my business intact. My wife never let on that she knew about my cross-dressing, but I had gone to great lengths to hide it from her. I had never had a single feminine garment in the home and didn't shave my legs, let alone prance around in a dress anywhere she could find me. Instead, I rented a small, second story office over a Chinese restaurant located a few blocks from my business's headquarters. I paid for it with company money that my wife never saw and, probably, would have killed me for not disclosing to her. I'm sure that she would have been upset about all the money I spent on rent and my female finery over the years, since she would have spoiled herself further with it. I had sometimes felt guilty about it, but, given the ending of our relationship, those feelings were relegated to relics of the past. There were other opportunities to indulge in cross-dressing that my job provided me too. The five to seven business trips a year I took always gave me the chance to hang around the hotel room en femme. I never ventured beyond the room though, fearing that my body hair would give me away. Once my divorce was finalized, however, my body hair was as gone from my body as my wife was excised from my life. The first trip after the divorce, I finally worked up the never to venture out of my hotel door in a dress. I found a local gay club that accepted me as an aspiring t-girl that I was not, exactly, aspiring to be. As I made my way around the city to and from that club, I got disparaging looks on the street from some when I passed under a street lamp that night, but I was left alone and free to be myself unmolested. It was the most freeing night of my life. I returned home with a renewed sense of vigor about my cross-dressing. I brought home all my feminine belongings from my secret office and set them up in my guest room, which I made over into my personal den of femininity. I painted the walls in a pastel green, put down a nice area rug over the wood floors and decorated it with pretty paintings of flowers and scenic vistas. Every time I looked in the closet that overflowed with my feminine wardrobe and the dresser drawers that were filled to the brim with my supports and other frilly undergarments, my heart raced as I day dreamed about how I would look in one outfit or another. That bedroom was not the only thing that I took to beautifying. I made a conscious effort to try to make myself as beautiful as possible. While hair removal was part of my normal routine by that point, I took to moisturizing my skin each morning before I left for work, as well as each evening when I returned from work. My toenails were always polished in colors I only wished I could flaunt on my fingertips. My diet and gym habits changed to suit my new objectives as well. I took to an all cardio workout and a low calorie, low protein diet to shed some of my excess weight. All that running and the hours I spent each a day on my stationary bike did wonders for my legs, thinning and toning them. I couldn't resist sliding into a pair of pantyhose or stockings each night after showering just to see how good they looked. It finally got to the point that I felt that the only giveaways to my gender where my hair and face. While I had slight features that made me appear androgynous, my thick eyebrows, combined with my short hair, were clear indicators that I was a man. Although, I was able to conceal the eyebrows with face putty makeup and cosmetics and put on some expensive wigs, I was still miserably unhappy about the way I looked when I took them off. Despite that displeasure, I was thrilled about the effect the cosmetics and wig had when I went on my next business trip. When I walked out of that hotel room, I didn't get a single disgusted look, but I got some other looks. I turned some average looking guys heads as my padded out body looked killer beneath my mid thigh length, black and white, long sleeve dress with an exposed full length zipper and a rounded neckline. I had guys coming onto me before I left the hotel. I started towards a gay club I found online before my confidence grew and I entered a department store along the way. People looked at me as if I was overdressed for shopping, but the looks I received were not disapproving. Some of the women I saw complimented my dress and shoes. I ate it up like you couldn't believe, using my most androgynous tone to thank them. No one seemed to think that there was anything off about me shopping for shoes and lingerie dressed as I was. As I walked out of the store, I could not stop grinning. I knew that I had passed myself off as a woman to strangers under the brightest lights I would ever walk beneath. At that moment, I knew that my alter ego, Kristi, had finally come into her own and could stand independently from the drab Rory Fleming I had been all my life. Being Rory Fleming had grown so tedious. I viewed the man I had always been as an impediment to the girlish vision I had of myself. While I had no desire to go the transsexual route, I wanted to live as a woman. I wanted to be free of the binds and expectations that were forced upon me by my gender. The hours I spent at work as Rory were driving me mad. The longer I spent my time outside of work exclusively en femme, the more trouble that making myself over as a man seemed to be. I looked in the mirror each morning before work and saw the man staring back at me. I couldn't help but think about the vision of femininity that I could be looking at instead as my hands would invariably start to drift towards my makeup bag before my better judgment made me pull myself away from the mirror. I knew that I needed to make a break from Rory Fleming. His life was one that I did not want anymore. Rory Fleming life, however, was directly intertwined with a good number of others. By walking away from my life as Rory Fleming, I would send the lives of my employees into chaos. I didn't know what any successor would do to my company if I sold it. It was a nagging sense of responsibility that kept me from turning my back on them. That was what drove me to make a move on my business trip. I slipped on a black dress with long sheer sleeves, a flared, knee length skirt and a boat neckline and walked into the bathroom going over in my head what I was about to do. I'll admit that I had second thoughts as I put on my makeup and pinned my long, dirty blonde wig to my bald cap. Still, I hadn't gone through all the trouble just to chicken out. While I was getting ready to step out of my hotel that night, I knew that my personal assistant was doing the same at her sister's house a few miles north. I had no real reason to attend the convention as I was not soliciting business from any of the people there. Still, it provided me with a convenient cover to invite Valentina along. Valentina was more than happy to make the trip with me since she rarely got the chance to see her sister, who lived so far away from our office. During the convention, I had overheard her dinner plans with her sister that night and knew that my opportunity to expose Kristi to Valentina had come. When we parted that evening so that Valentina could join her sister for dinner at a nice Italian restaurant, she had no way of knowing that our lives would never be the same. I knew it, however, and that realization made me slow down as I paced around my hotel for a few minutes before I worked up the nerve to slide my feet into my black, platform pumps. After I picked up my purse, I slung it around my arm and headed out of my hotel room door. I thought about what would await me at the restaurant when I "accidentally" ran into Valentina. I had a good idea about what Valentina would do. She was an assertive woman. That was a good part of why I hired her in the first place. She helped me manage my employees better than any assistant I ever had, since she made sure to hold peoples' feet to the fire on my behalf. Her assertiveness was another reason why I had chosen to arrange to expose my secret to her first. I was sure that she would use it to maximize her leverage over me. I was banking on that, since I knew exactly how I wanted to play that response to my own advantage. Despite being reasonably sure of what I was going to be walking into, I was still nervous about the situation while I drove towards the restaurant. I parked the car and stared at the building for a good ten minutes before I popped open my door and swung my legs out of the car. As my heels hit the pavement, I felt as if there was no backing out. I needed it. I needed to be Kristi 24/7. I walked towards the door with my purse dangling from my shoulder while a romance novel was pinned towards my chest with my arm. I moved to open the door, but a gentleman grinned as he saw me and pushed it open. I thanked him politely with a smile that kept that smile plastered on his own face before I gave my name to the hostess. She nodded as she told my table for one was ready. I struggled to contain my nerves as I walked behind her to my table. My knees felt weak beneath me as I wondered how much of a scene Valentina was going to make when she saw me. When I entered the dinning room, I saw Valentina immediately, sitting across from her older sister. Despite me clearly seeing her, Valentina did not give me a second look before I sat down at a table with a good view of her table. The waiter came by and asked me if I was waiting for anyone else. I shook my head and showed him my book as I replied, "No, I'm dining alone tonight." The waiter was surprised to hear it and complimented my appearance before faking shock that "such a pretty lady" was dining alone. I greeted his flirts warmly, knowing that he was probably angling for a good tip that I did end up giving him. As I sipped on my wine and eat my salad while I waited for the main course, I occasionally tore my eyes away from the book and stared at Valentina, hoping to meet eyes. It never happened though. I was getting concerned that my transformation was too complete for her even to see through it. I had not accounted for that possibility, but the more I thought about it, the stranger it had to be for her to look at my feminized body and conclude that I was, in fact, her male boss. I knew that I had to force the issue to make sure that it got out there. When Valentina got up to go to the bathroom, I followed her towards the ladies' room. The bathroom was only setup for one person at a time, so I waited my turn as I hoped that no woman would get behind me on the line. I was relieved that I was still the only one on the line when I heard the door knob turning. I took a deep breath as I prepared for the scene I was about to cause. Valentina opened the door and didn't give me a second look until I pretended to gasp and said, "Valentina!" My feigned horror and recognition of her face stunned Valentina for a second while she tried to place my face before she made the connection. "Holy Shit!" Valentina exclaimed as I grabbed at my heart and pushed her back through the bathroom door and closed it behind us. I locked it behind me as Valentina looked over me with a stunned expression. "What the hell is going on?" Valentina finally asked. I stood in silence, trying to pretend that I was coming up with a lie to answer her with. "Why are you dressed like that?" Valentina barked. Again, I stood in silence, trying to make it seem like I was struggling to come up with some pathetic excuse. Valentina glared at me while she looked me over before she realized the little subtle details of my appearance. Her eyes gazed at my arched brows that I formed through the use of face putty makeup, she looked at my skillfully applied makeup, her eyes then drifted to my toned, thin legs and the hourglass shape of my sculpted and padded out body. She took a step back as she realized that my appearance was not the result of some prank or joke. It was clear to her that I had some practice being en femme. There was no denying it. I clearly wanted to look the way I did. "How long have you been doing this?" "Since I was a kid," I replied honestly while blushing. Valentina shook her head as she said, "No wonder your wife left you." "That wasn't the reason," I responded. "It certainly looks like the reason. She wanted a real man." "She didn't know about this. I went to great lengths to hide it." "So that's what drove her into another man's arms," Valentina concluded. I froze and wondered if she was right. I did spend a good amount of time away from her, trying to live out my feminine fantasies on the road and in my second office. Valentina shook her head as she gave me an appalled look and said, "Regardless, she clearly did better. God! What would she think if she ever caught you like this?" I shook my head, knowing the answer, but deciding not to speak it, since I knew that Valentina surely knew it as well. Valentina's disapproving look grew steely as she asked, "Who else knows about this?" "No one," I replied truthfully. "How much are you willing to give to keep it that way?" Valentina asked. I struggled not to grin, knowing that she had played right into my game plan. "What were you thinking?" I answered. "I was thinking a raise and a promotion are in store," Valentina countered. I gave Valentina a nervous look, trying to convey that I was scared, prompting Valentina to press further, "And I think that there should be some changes at work." I smiled at Valentina's confident tone as I breathed a sigh of relief and responded, "There will be some changes at work." "Yes, there will," Valentina replied with decidedly less confidence in her tone. "You're right. I can't hide this anymore." "What?" Valentina rejoined, stunned by the turn of events. "I'm just going to come out with it when we go back." "Rory, you might want to rethink that...," Valentina began to respond, realizing that her leverage was gone. I shook my head as I said, "There's no going back, now. I'm a woman at heart, and it's time I start living as one." Valentina gave me a dumbfounded look, realizing that I was serious. She shook her head before she exclaimed, "You can't be serious!" "I am. I can't remember feeling like this, Valentina. I feel free for the first time ever. There's no going back now. I can't go back to pretending to be something that I'm not." "But you're not a woman," Valentina countered, shaking her head. "Not yet," I retorted. "Not ever," Valentina rejoined. "I can be close enough," I responded to Valentina's stunned silence. I then took a deep breath before I asked, "Can you handle that?" Valentina stared at me blankly before she blinked her eyes and asked in a vacant tone, "Handle what?" "Handle working for me." "I've been working for you for..." "No. I mean working for Kristi Fleming." "Kristi? That's the name you gave yourself?" "It's a perfectly fine name." "For a tramp," Valentina retorted. "I like the name," I responded, projecting some confidence that stunned Valentina. Valentina looked me over and realized that I was not joking. I was at the point of no return, and I was determined to leave Rory Fleming in the past. Valentina seemed to be in almost disbelief before she said, "I could work for you." "I don't know. You hesitated, and, let's not forget, you tried to blackmail me." "I was not...I wasn't...," Valentina stammered as she had become the one who was trying to desperately come up with an explanation as I flipped the tables on her. "You can't deny it, Valentina. That being said, however, you are really good at your job. You like controlling people for me, and I'm going to need that skill, as I'm sure that some of my employees will have some trouble adapting to the changes in the office." Valentina nodded while I gave her an approving look before I said, "Now, if you'll excuse me, I need to freshen up." Valentina gave me a curious look before she said, "Of course. I'll get out of your hair, but If you want to join me and my sister..." "No. No. You two enjoy yourselves," I replied before I showed Valentina out of the bathroom. I felt a sense of relief run through me as I sat down on the toilet seat. The die had been cast and there was no turning back. I had forced myself into a feminized corner, and I could not have been more excited about the prospect. I returned to my table and ate my dinner before I headed out of the restaurant. Valentina had already gone by the time I left and went back to my hotel room. The next day I met Valentina at the airport. She was stunned to see me in male clothing and asked, "What happened to Kristi?" "Kristi doesn't have identification yet," I replied before we went through security. When we finished, we ate breakfast together in the terminal's food court. Valentina seemed uncomfortable at times as I discussed what the next day at work would be like. Valentina sensed that the situation could spiral out of control and practically pleaded with me to reconsider. I laughed it off, remembering when she was trying to extract a ransom for keeping the secret she now wanted me to keep. We made the trip back home without incident before we picked up our cars and returned to our homes. I walked into my house, stripped out of my shirt and pants and headed up the staircase to put on a pair of leggings and a sweater dress to lounge around my home in before I tended to the laundry that had been soiled during my trip. I hand washed my feminine intimates in the sink before I took to washing the rest of my clothing. Once I finished, I ate a quick meal and turned on the television as thoughts about what the next workday would bring filled my head. ----------------------------------------------------------------------- After spending a night rethinking my plan, I awoke the next morning, ready to move forward with it. I got dressed, put on my makeup, styled my hair and headed out of my home. I got into my car and drove to work feeling as if I was finally ready for this moment. I pulled into the parking lot and parked in my reserved spot. No one seemed to notice me as I got out of the car, making me feel even more confident about what I was doing. I walked towards the doors to the building. A smoker saw me and gave me a smile as he opened the door for me. I politely thanked him as I walked inside. My heels clicked on the tiles that lined the lobby floor as I walked towards the elevator. The lobby was sparsely populated as I moved through it with only one person standing before the elevator. The older looking woman I recognized from another business in the building smiled at me before she told me that I had a pretty purse. I thanked the nice woman and made small talk with her as we entered the elevator together and exited on the second floor. While she made her way to her office, I was having second thoughts while I was staring at my office door. The sight of Valentina coming to a stop and staring at me with a slack jaw as she passed by the door helped me regain my nerve. I knew that I had crossed the Rubicon. There was no going back. So, I walked towards the door, trying to project confidence. I pushed open the door and said hello to Valentina. "Hi, Kristi," Valentina said after a pause. I could see that she was shocked that I had been true to my word. I greeted her before others began to congregate around us, confused by what was going on. I greeted each of the gawking faces of my employees before I announced that I was 'transitioning' to a woman. Shock is the most apt word to describe their responses. I could see the disgusted, disapproving looks on most of my male, and a few of my female employees, were giving me. There were over 20 employees in the office. They were the only employees of my company I dealt, leaving my company's subsidiaries to be dealt with by those employees. If I was in their shoes, I would have been just as shocked as they were. I can't blame them for their reactions given that it's just not that common of an occurrence for your male boss to show up in a dress, tights and black pumps and tell them, "You can call me, Kristi." I half expected some of them to quit on the spot, but the job market was not robust enough for them to just walk away from a job, no matter how uncomfortable they were with their boss. Consequently, even the most clearly disgusted of my employees put up fronts of begrudging acceptance with respect to my feminized appearance. Growing tired of being gawked at like an animal in a zoo, I took sanctuary in my office. The office then began to get on with business as usual, as best as it could. My feminized appearance had caused substantial upheaval, and I knew that it would hamper the business in the short run as my employees were consumed with talking about it. I worked in solitude for over an hour before someone from the office worked up the nerve to knock on my door. I was hardly surprised that it was Valentina. I asked what I could do for her. My chipper tone prompted Valentina to waive over her fellow administrative assistants from the small bullpen they worked together in. The five girls looked me over before Valentina complimented my knee length, grey, tweed dress with a beaded fringed trim at the neck and cuffs, solid piped waistband, round neck and short sleeves. I loved that dress and grinned as I replied, "Oh, this old thing. It's nothing. I really like those boots." Valentina looked down at her brown leather boots that covered her sheer pantyhose covered feet and smiled. A few of the other girls then exchanged compliments with me, clearly feeling me out to see how at ease I would be with them. After making small talk with the girls for a little while, they exited the office and got back to work. I worked for another couple of hours before I walked through the doorway to my office to talk to Valentina about ordering lunch. Valentina took my lunch order down and called it in before one of the secretaries looked over to me, noting the pen in my hand and said, "Kristi, you look a little a secretary yourself holding a pen like that?" I looked at my hands and saw the pen gripped with my hand that was decorated with long painted fingernails. I shook my head as my member stirred at the suggestion and said, "I think I look rather like an executive." The secretary, Carol Berton, shook her head as we exchanged a few more comments before Valentina got up from her chair to go to the bathroom. Seeing a chance to get off my heeled feet while I talked with the girls, I sat down on her chair. As I crossed my black, opaque tights covered legs and kept talking, Carol said, "Now, you really look a secretary." "Me? Come on?" I replied as my manhood surged between my cheeks and pressed against the cushion of the low back chair beneath it. "Seriously, turn towards Valentina's monitor," one of the girls said. I complied with the request to the girls' giggles before Carol said, "That's a secretary right there if I ever saw one." I blushed, enjoying myself as Valentina walked back over to us. She looked me over as I sat in my seat and said, "Getting comfy?" "She seems pretty comfy being a secretary," another girl noted. "I wouldn't go that far," I replied. "Why not? I think you'd be a wonderful secretary," Valentina interjected. I blushed again as I said, "I don't know about that." "You got the perfect look and you clearly know how to fit in with the girls," Valentina replied with a laugh. I laughed too, feeling oddly proud of the compliment I received. Valentina read my reaction as she said, "If you want to be a secretary, you can be one, Kristi." "Then, who would do my job?" I retorted. "I could do it," Valentina replied, rather predictably. I scoffed, despite knowing how closely she worked with me. I shook my head and responded, "You think you could do it?" "I know I could." I laughed, which only served to make her angry. I baited her, and she took the opportunity to press, "If you're so sure I can't, why don't you prove it?" "What? Like give you a shot?" I replied leading her on. My response planted a thought in her mind I was not sure that she had really considered yet. I saw her eyes widen as she processed the response and said, "Yes, I should get a shot to prove you wrong and if I'm good..." "What you'll get to stay the boss?" I finished her sentence for her. The look on her face told me that I had gone further than she was willing to press. She was not confident enough to suggest the very thing that I wanted. I loved the idea of being stuck as a secretary. I wouldn't really be stuck as I had the money to walk away and retire right then, even without selling my company. The rigors of running the business had drained me though. They had also played a part in the implosion of my marriage, as my wife had chided me for years for ignoring her in favor of work. I had profited handsomely from being an entrepreneur and having all the responsibility of building and running my own business. They were, however, not something that I needed anymore. I wanted to break from it, but I felt a sense of duty to my employees to not just sell the company to someone who might turn around and terminate them all. Valentina was a real company girl. She wanted the company to do well and was as loyal as they came with respect to her coworkers. I knew that she would be the perfect girl to takeover. Valentina responded to my comment after a pause and said, "Yah...If I do well, I think I should stay the boss." "Where will that leave me?" I asked, knowing the answer. "You'll find that I'm very fair with the girls," Valentina replied with a laugh. The other administrative assistants gave us curious looks, almost in disbelief that we were having this conversation. I grinned at their stunned faces and felt a sense of relief come over me as I said, "You've got yourself a deal." Valentina gave me a stunned look. I got to my feet and held out my hand. Valentina shook it with a blank look on her face. I put my arm around her shoulder and guided her speechless body into my office and began to hammer out the terms of the deal with her. We sat down and negotiated the terms of the deal. I put in provisions to allow me to step back in as the boss if the company performed poorly. Valentina insisted on corresponding provisions that expanded her time as the boss if certain benchmarks were met. All told, we agreed to let Valentina run the business for up to ten years, provided that she met each of the benchmarks for growth. As we discussed those terms, Valentina seemed to be confused by my willingness to give away my company. The longer the discussions continued, the more obvious it seemed to become to her that I wanted to be stuck as her secretary for a while. I wanted to sign my life, as I knew it, away. I had no more use for it. The negotiations continued through lunch, which we shared in my office. Valentina became more assertive throughout the negotiations and made one last suggestion about our future working conditions by insisting on provision that required me to earn my role as a secretary, as she saw fit. The terms struck me as amorphous and likely unenforceable in a court of law, so I did not resist them. In truth, I was eager to see what she had up her sleeve. I knew that she would be ready to break it out once she was the one with the boot on my throat. "So when's the start date going to be?" I asked as I finished typing in the provision. "Well, for me, how about tomorrow. You can start a week from today." "What's with the delay?" "It will give us a chance for you to get your personal affairs in order, while I transition the office to the new regime." "You don't need me for that?" I countered. "I practically ran this place while you were going through your divorce," Valentina retorted. I nodded, knowing that she was telling the truth. I then agreed to the terms of the start dates and typed them in. I printed the contract, and we went over it and made a few tweaks before we printed another version of it that we both approved of. As we stared at the contract before us, Valentina said, "We'll need witnesses. Carol's a notary too." I nodded while I amended the documents to include a notary block for the signatures and reprinted it. Valentina exited the office to take it off the printer as she called the secretaries into my office. The girls were all curious about what we had agreed to. Dumbfounded looks came across their faces as they found out just what we had come up with. One of them asked, after a moment of silence, "Do you really think that Miss Constantini can do it?" I nodded as I explained that I had worked closely with Valentina for years. I noted that I had shown her how to do everything I did in the event that I died unexpectedly without a succession plan. I even reminded them that Valentina filled in for me while I was distracted by my divorce proceedings. With that, I silenced any doubts they were willing to air before I said, "Well, let's get this over with." The girls watched as we placed our signatures on the paper before Carol notarized them both. Some of the girls laughed as they shook their heads at us. "I'm sure you'll like being one of the girls, Kristi," Carol said as she rolled her eyes. I nodded silently, knowing that Carol was not quite aware of just how much I wanted to be just that. ----------------------------------------------------------------------- With the deal formalized, I headed home to embrace my week off. I knew what I wanted to spend it doing, and I immediately sprung into making the arrangements. My course of action was clear. I wanted to immerse myself in femininity as quickly and dramatically as I could. I wanted there to be no visible sign that I was a man outside of closed doors. I started by making appointments with salons for hair and nail extensions. I felt that by ridding myself of my prominent brows and adorning myself with long fingernails and strands of hair the last vestiges of my publicly displayed masculinity would be erased. With those changes made, I knew that I could not step out of the home as a man without being the subject of derision. I would be blissfully trapped in the guise of a woman. In addition to making the feminization arrangements, I devised a schedule to put myself through my feminine rigors. Each morning, I awoke dressed in my mauve colored nightgown. I forced myself out of bed before I made myself a low calorie breakfast. Once I finished eating, I cleaned up the kitchen and headed for the shower. After getting the extensions, depending on when I washed my hair last, I sometimes washed my hair, while other times I put it up in a shower cap. Wearing a shower cap felt so strange. Still, given the amount of time it took to wash my newly long locks, I understood the purpose and why my wife had worn one so often. After I finished showering, I dressed in some of the clothing I was planning to wear to work the following week and a pair of pumps. I would then do my makeup before I accessorized myself with jewelry and bags and ran around my home doing various chores. I cleaned every square inch of my home, trying to force myself to stay on my heels from 9 to 5, pausing only for the respite of lunch. After lunch though, I was back to scurrying around. By five o'clock each day, I practically threw my heels off. It quickly surpassed my morning dressing ritual as my favorite moment of the day. I felt a sense of freedom from both, but the moment I took off my pumps was accompanied by a sense of physical relief. I then changed and put on my in home workout clothing, which was little more than a pair of yoga pants and a girls' athletic, black tee shirt. I went through my cardio workout before I made myself dinner and went to take my evening shower. The evening shower was the thing that my little guy seemed to most look forward to as I could see how sweaty and slightly bent out of shape it was when I removed it from its gaff each evening. It almost sprung to life the minute it realized that there was nothing restraining it anymore while I took my evening shower. As I exited the shower each evening, I would go through my typical routine of moisturizing my skin and applying my makeup remover. I hate seeing my face without makeup on it, but I know how much damage sleeping in makeup does to my skin. Consequently, I made sure, then and now, to remove every bit of it before bed. I only ventured outside of my home two times during the six days that passed before I returned to the office that Monday morning. The first was when I went to the salon. My appointment was during the late morning of a workday, so the crowd in the salon was light when I arrived. I went dressed fully en femme from my heels to my dress. The receptionist gave me a strange look as she noted my appointment for my hair. It was only after I pulled off my wig that the girls in there understood my need for the extensions. The stylist who worked on my mess of short hair did not ask many questions. I noted early on that I had cut my hair short at one point to make it more manageable, only to realize that I had made a horrible mistake. That was enough for the stylist as we made small talk throughout the hours she spent painstakingly adding strand after strand of the extensions to my hair. When she finally finished, my hair was cut and layered before it was dyed a dark brunette color with highlights. I could not stop grinning at my long, brown hair. I loved the cut and how it framed my face. I felt more normal at the moment than I could ever remember feeling. After I finished with my hair, my eyebrows, which I had thinned with tweezers to make them a little more presentable, were waxed into two high arching brows that looked wonderful. I was very happy when I walked out of the salon after tipping the stylist generously. From the hair salon, I headed over to the nail salon to get fingernail extensions and to get my nails painted. My feet received a pedicure from the nice Korean pedicurist after the addition of extensions to my fingernails. I struggled to pay the woman as I left the salon, not realizing how difficult the long nails would make picking things up. I realized that I may have gone overboard with the length of the nails, but I figured I could always have them cut back. The next day I made my second trip out of the home to go shopping. I started by shopping at the supermarket for the various items I needed to keep my house stocked throughout the week. During that trip, I was treated as nothing but a genuine lady, not as if that means much in this day and age. I pushed my cart through the market, feeling that I was a normal woman, just like the ones around me. The only perceptible difference between them and me was the fact that I was wearing a dress, while they were, without exception, wearing pants. That fact made me shake my head as I remembered all the times that I would have killed to wear a skirt or a dress, but was restricted to wearing pants. I was glad that I didn't have a single pair of pants that would not look ridiculous on me at that moment. I did find, however, that my androgynous voice threw people a little. I think they expected me to have a higher, perkier voice given my girly girl appearance. Still, they did not raise any suspicions to me. It was that final experience en femme in public that made me realize that there was nothing more that I needed to do to in preparation for the start of my new life en femme. ----------------------------------------------------------------------- When Monday morning finally came, I hopped out of bed and went about my morning routine. After eating and showering, I went back into my bedroom and started getting dressed. I put on my gaff before I slipped on a thong for extra support. Once I finished making sure that I was properly tucked away, I gingerly put on a pair of black, sheer pantyhose. The familiar excitement that I was used to filled me as I curled my toes in my hosiery before I skipped over to the closet. I pondered my options for a moment before I pulled out an above the knee, grey pencil skirt and a black, cowl neckline top with gold studs along its ruched side from my closet and stepped into the skirt. I then headed over toward my dresser and applied the glue to my breasts forms before I cupped them to my chest. After the glue had settled for a bit, I took hold of my bra and wrapped it around my chest. I adjusted the straps of my bra before I took hold of the three-quartered sleeve top and pulled it over my head. I caught my reflection at a distance in the dressing mirror and smiled at it for a second before I headed into the bathroom. I felt the coolness of the tiles through my pantyhose as I brushed my teeth before I began to style my hair. I brushed it out and sprayed it with hair spray until it was the way I wanted it to look. Once I was satisfied with my hair, I took out my makeup bag and began to add some color to my face. As I added the last touch to my face, I could not help but smile at my reflection. I knew that I was finally going to go to work looking exactly how I wanted to look. I headed back into my bedroom with my makeup bag and removed my 4 inch heeled, charcoal, suede pumps from the closet. I stepped into them before I walked out of my bedroom and down the staircase. I then put my makeup bag away in my purse and headed out the door of my home. I stepped into my car and drove towards the office wondering what it would be like to not be the boss anymore. While I still owned the company, I had effectively given up control of it until Valentina decided to give it back or performed too poorly. The only threat I could hold over her head was the threat of selling of the company if she pushed me too much. That put me in a better situation than most secretaries. I'm sure most secretaries would love to have the potential to kill their bosses' jobs at their whim, but I knew that doing so would foreclose my return to the company I had built from the ground up. While I was getting there, I was not willing to pull that trigger yet. After I parked, I swung my legs out of the car and headed for the door to the office building. My heart raced, almost faster than it did when I had entered the office en femme for the first time. I felt confident in my appearance while I walked past the workers from the other offices that largely looked right through me. I walked towards the elevator. I pressed the button and got on with a group of people. I disliked being in such close quarters en femme, but no one said two words to me before I exited on the second floor and walked towards my office's door. The room seemed to get quiet as I entered the office. People seemed unsure of what to make of me. They knew I owned the company, but they also knew about my deal. I was sure they were trying to figure out how to toe the line of treating me like a secretary without making any mistakes that might get them terminated down the road. I could hear whispering that Valentina was just my puppet and that I was trying to use her to live out my fantasies. Only the latter was true, but I did not let onto that. As I walked towards my office door, Valentina emerged with a smile. She gave me an approving nod before she greeted me. After exchanging pleasantries, Valentina asked, "Are you ready to start your first day, Kristi?" "I sure am, Valentina," I answered. Valentina grinned from ear to ear as she said, "Glad to hear it. Let's introduce you to your new coworkers and get you started." I gave Valentina a queer look before I stated the obvious, "But I already know everyone?" "Everyone doesn't know Kristi," Valentina countered. "They already saw me like this...," I began to reply. Valentina cut me off, "I want my employees to get to know their new secretary." I struggled not to grin as Valentina emphasized "my employees" and the word secretary. She was trying to bring home the new power arrangement to all the staff and me. Feeling as if it was not my place to stop her, I said, "After you then." Valentina nodded before she motioned for me to follow her. Valentina walked me over towards a group of male employees and introduced me as the new secretary. I could see their judgmental looks and disapproval behind their attempts to be polite. A sense of disdain seemed to just ooze through their bland greetings. I did not stand around with them for long before Valentina led me over towards a group of administrative assistants. The girls grinned at me, but none more than Carol. Carol was, easily, Valentina's closet friend in the office. They talked non-stop, ate together and shopped together. They even dated together from time to time. I was slightly jealous of their relationship, as I never had a friendship as close as theirs. As Valentina introduced me to them, I could see each of the girls looking over my outfit. Carol broke the ice by paying my shoes a compliment. I wasted little time in returning it by gushing about her dress. My response seemed to open up the other girls as they each shot me a compliment that I returned. As I exchanged compliments with the girls, I could see some of my former male employees rolling their eyes. I could almost read their minds. I was sure that either believed that I was gay or, maybe, that I was a woman at heart. Regardless, my comments and gushing with the girls had forever broken the link in their minds between me and my masculinity. I was only a male biologically to them. I knew that I would never be able to go back to the man I had been, but that was the plan. Valentina pulled me away from the girls to greet some more of my employees turned coworkers. I could sense that some of the guys were uncomfortable around me, but they had been uncomfortable the first time I showed up in a skirt. The females were far more openly supportive, however, there were two that were more conservative. They were the most visibly disgusted with me. While I'm sure that some of the men were even more disgusted, they hid it better. After I was finished being reintroduced to everyone as Kristi the secretary, I turned to Valentina and asked, "So where's my desk?" "That's pretty presumptuous," Valentina retorted. "What do you mean?" "You think you can just waltz right in here and have a desk, just like that?" Valentina inquired. "Yes, if you want me to get any work done," I responded. "There's plenty of work you can get done around here without a desk." "Like what?" I countered. "There's coffee to be made, there papers to be copied, there's errands to be run. Each time you do one correctly, you'll earn something you need to be a full time secretary." "I'm going to earn what I need?" I replied, almost in disbelief. "Yes, you'll earn the desk. You'll earn a computer, but let's not get a head of ourselves just yet. First, you've got to earn a pencil." "Earn a pencil?" I replied, growing aroused by the turn of events. "Yup, now, to earn that pencil, I'm going to send you out with the company credit card to bring back coffee from Starbucks. "I can't bring back coffee for twenty-four people alone." "Not in one trip. I'd say four at a time will do it." "But it's three blocks away..." "Then, you better start cracking." "Well, what does everybody want?" "You can go and ask each of them," Valentina countered. "And what will I write down their orders with if I don't even have a pencil, let alone a piece of paper," I retorted. Valentina grinned as she replied, "It's just four orders, how hard can it be to keep it straight?" I knew right then that she was trying to get back at me for questioning her short term memory from time to time. If I was in her shoes, I probably would have done the same thing. "Can't I take the 24 orders at once and drive there?" I replied. "I'd rather you get the exercise," Valentina answered with a smile. I rolled my eyes at the comment and asked, "Well, who should I start with?" Valentina pointed me towards Kirk and said, "Start with Kirk and work your way around the office." I nodded before I walked over to Kirk and asked, "Kirk, do you want anything from Starbucks?" "It's really not my cup of tea," Kirk replied, clearly uncomfortable with my feminized appearance, but too intelligent to make a fuss about it. "Well, Valentina is paying with the company's credit card." "She is?" Kirk responded with a laugh. "She only has a set amount of funds for these kinds of things, but this is what she wants to waste the money on," I replied. Kirk shook his head before he gave me his order. After committing Kirk's order to memory, I moved onto the three employees, whose desks were closest to his. They all gave me incredulous looks as detailed my task before they gave me their orders. Once I finished memorizing the first four orders, I headed out of the office suite and into the hallway that lead towards the elevator. After the elevator dropped me in the lobby, I hurried out of the building. I looked down at the pavement as I made my way towards the sidewalk, carefully trying to note where each crack was beneath me feet. While I didn't want to take a tumble on my way there, I was more looking for them out of fear of spilling coffee all over myself on the way back. I was happy that it was barely 65 degrees as I made the walk. The warm sunshine kept me warm enough, but I did not break a sweat as I sauntered down the sidewalk. I walked into the Starbucks and was happy to see a relatively short line before I stood on it. No one around me seemed to take much notice of me, save for the occasional guy checking out my legs. The barista called me forward and I gave him the four orders I was given. He nodded before he told me the price. I reached into my purse and fumbled with the company credit card that Valentina had given me. I struggled to clasp it as my fingernails kept snagging against other things in the pocketbook before I managed to pull it out. After paying, I stood to the side and waited for my name to be called. They somehow butchered Kristi Fleming horribly, calling out "Misty Jennings." I don't think my feminized name is particularly hard to pronounce or take down. I choose not to correct them as I took the drinks and made the walk back to the office. I started by handing the drinks out in the order that I took the orders. Kirk took his first before I gave out the next three drinks. As I finished giving the last cup to one of my employees, I checked the clock on their computer monitor. I frowned as I realized that getting coffee for the four of them had taken me over thirty minutes. I did some simple calculations and concluded that I would be fetching coffee for over three hours. I remember thinking, 'Will they even want coffee at 1?' Still, I persevered with the task. I went over to the next four employees and took their orders. I hurried back out of the office and the building, made my way down the street and walked right back into Starbucks. My return brought a reaction from the barista. He grinned and said, "Back already." "I've got to come back four more times after this," I replied. He shook his head before I placed my order and stood aside to wait for it to be prepared. Once it was complete, I picked it up and carried it back to the office. As I made my way down the sidewalk, I felt a familiar sensation of pain in my feet and ankles. I knew it was from the constant pounding of my heels into the cement and asphalt beneath my feet. I was dismayed that the pain was setting in so early. While I had expected it, I hadn't expected it to rear its head until at least after lunch. I shook my head and tried to keep my mind off the pain as I made my way back to the office. I hurried inside the building and up to the office and served the drinks to my employees before I took down the next four orders. The third trip to the Starbucks was even worse as the pain in my ankles and feet intensified. I could sense that my body was desperately pleading for a break from all the walking I was doing in my pretty shoes, but Valentina had deliberately setup my task schedule that day to make sure that did not happen. I cringed as I gave my third order to the barista. He shook his head and said, "Your Company must really love this stuff." "Apparently," I replied, not wanting to admit that I was sure that the task was just Valentina's way of getting a measure of revenge for every little slight, real or imagined, that she felt I had given her or Carol over the years. I lugged the four cups of coffee back to the office, huffing a little as I walked down the sidewalk. I put up a tougher exterior as I entered the building, not wanting to show my discomfort. The employees thanked me as they took their cups. Despite my smiles as I told them they were welcome, I was dying inside that I was only halfway home with respect to the task. The only thing that kept me going was my masochist streak that found some sort of arousal in the pain I was feeling. Together with my ever present urge to be feminine, the source of the pain made excited, even though I would have killed for a seat at that moment. I tried to put the pain out of my mind as I went around taking the fourth round of orders. As I began to walk towards the door to the hallway, Valentina called over to me to ask me where something was. I racked my mind for a few moments before I remembered where I had placed the document and told her. She thanked me before she turned and walked back into my old office. Turning to step out the door, I tried to think about the order my employees had given me. I paused as I realized that I was no longer certain about it, as my mind had drifted away from the orders. "Shit," I exclaimed before I went over to my employees and asked them for their orders again. Two of them gave me peeved looks, almost as if they could not believe that I had somehow mixed up four orders and had to ask again. I grinned and tried to stay chipper as I took their miffed responses in stride. Once they gave me their orders, I hurried out of the office again, careful to repeat the same routine I had done three times already. By the time I reached the Starbucks, I felt as if nails were being driven into my feet. I shifted around in my shoes as I waited on line before the barista called me over and asked, "Four more?" I gave him a sullen nod before I told him how each of the employees wanted their drinks. The barista took the order without needing my name before I walked over to the side to wait for them to be prepared. The manager gave me a smile as he said, "I've seen you around here before." "I've been here a couple of times today," I replied with a smile. That must have given the manager the wrong impression as he responded, "Why have you been here so many times?" I explained my task to him without explaining the background to it. The manager shook his head as he said, "Your boss is a dick." "Kind of," I replied with a grin. "You know we're hiring," he then said. I gave him an amused look before I replied, "Thanks, but I make more money at my job." The man shrugged and nodded before he said, "Then, how about I get your number?" "For what?" I answered, unsure of where he was going. In retrospect, it was rather clear, if unexpected. The manager gave me a peculiar look before he smiled and explained, "I was looking for a date." "Oh," was the full extent of my response as I was taken aback by the response. While I had passed as a woman, the idea that a man could talk to me and find me attractive was a shock. I stammered while he gave me some lame pickup line. The barista calling my name saved me for a moment as I scurried away and picked up the order. I politely rebuffed the manager on the way out, explaining that I was already in a relationship. The manager looked a bit defeated by my response, but he perked up as he replied, "Well, if he doesn't give you a ring soon enough, you know where to find me." I nodded with a smile as I exited the store. I almost forgot about the pain in my legs as I thought about the man's advances. His final comment, assuming I had a boyfriend, amused me. I'm sure that Valentina or Carol would have had a field day with it if they had overheard. 'When is he going to make an honest woman out of you', I could almost hear Valentina saying in my ear as I made my way back to the office. I walked into the building, made my way to the elevator and went up to my second floor office. After I handed out the cups, I took a fifth set of orders down and headed out the door again. It was already almost 1 in the afternoon when I entered the Starbucks for the fifth time. All the unanticipated walking that was causing so much pain throughout my lower body was also making me hungry. My stomach was growling as I placed the fifth order. The order was filled quickly before I started back towards the office. As I walked along the sidewalk, I felt the pain emanating from feet, ankles and calves and traveling up my lower back. After bringing the fifth set of drinks back and taking the last set of orders, I hurried out of the office clutching my back. I held it the entire way there, praying that I would have some sort of respite before lunch. Once I finished getting the final set of cups for my employee, true to her word, Valentina gave me a pencil. She handed it to me with this magnanimous look as if she was bestowing some valuable gift on me. I held the pencil up and asked, as sincerely as I could, "What should I do with it?" "Go put it down in your workspace, and then you can pickup my lunch," Valentina replied. I inquired where she had ordered. A frown came upon my face as she informed me of the name of the eatery. It was a pizzeria that made lunches that I was not particularly fond of. What made it worse was the fact that it was ten block walk and there was no parking anywhere near the place. I'm sure that those factors ran through her mind when she came up with the idea to place the order in the first place. She was sending me to the most inconvenient location, simply because she knew that I was in no position to refuse. I sighed before I turned to walk out of my former office door and asked, "Where is my workspace?" Valentina called over to Carol to show me where it was. I walked towards Carol, and she pointed to the vacant space beside her desk. I looked at the empty stretch of carpet and shrugged before Carol said, "You can put your pencil down there. No one's going to steal it." "I'm not particularly worried about that," I groused before I struggled to bend down to place the pencil upon the floor. The pain in my legs and back made standing back up even more of a chore. I had to place one hand on Carol's desk and push myself up to help right myself. As I stood up, Carol shook her head at my groaning and said, "That's not very lady like." "I'm not much of a lady," I countered. "I know with a name like Kristi, you're definitely a skank," Carol retorted. My head jerked towards her before a smile came across her face as her words had clearly gotten their desire result. I shook my head with a smile before I headed out of the office again. I was feeling deflated as I walked out of the office. The sound of my heels smacking against the tile floors of the hallway brought a smile to my face, as did the ever present restriction on my stride from the skirt of my dress. It was those feelings and the peculiar enjoyment of being the one on the other side of the boss's desk for once that was getting me through the pain that was slowing me down. I tried to focus on what I enjoyed about my present state as I exited the building and began to make the long walk down the street. As I turned down one street, I saw a construction yard. I did not think much of it as I walked by it. The idea of being ogled crossed my mind for a moment, but I did not think that men really still let out catcalls from the construction yard. My assumptions were not correct. Despite the progress that women had made in the office, it seems that some men still can't help themselves, especially when they're only working around other men. I heard a few comments directed at me. Most were thinly veiled sexual suggestions. Most of the men I saw did not have the guts to say them, but they laughed along with those that were either stupid or incapable of embarrassment. I tried my best to pretend to ignore them, but a smile came across my face. I felt strangely proud to be hit on by these men. I liked the idea of being attractive, even as I thought about really ruining their day and whipping out my manhood. The hecklers would be the ones getting teased for their unwittingly gay advances then, but probably not until after I was heckled, beaten and arrested for exposing myself. So I walked past the yard in silence as I made my way to the pizzeria. I smiled at the cashier as I told them I had an order to pickup under my boss's name. The handed me the salad and sent me on my way back to the office. Carol gave me a grin before I walked into Valentina's office to hand Valentina her lunch. As I gave it to Valentina, she reached down and took hold of a legal pad of paper. We exchanged the items in our hands before I told her that I was taking a lunch break. Valentina gave me a peeved look before I noted that I was entitled to a lunch break under the laws of the state. She begrudgingly accepted the explanation before I walked out of her office. I wondered what I should get for lunch, but I felt limited in where I could go. I did not have the luxury of determining how long my lunch break would be. Given the time restraints on my lunch time, and the weariness of my body, I decided to go to the cafeteria that was located in the basement of the building. I was never impressed by their food, but they were, simply, the easiest place for me to go to grab something quick to eat. With the decision pretty much made for me, I put my legal pad down on the piece of carpet that constituted my workspace. I then exited the office and got on the elevator. I took it down to the basement and headed for the cafeteria. I gave my order to the worker who I was glad was not familiar with me. Once my order was finally up, I paid for my lunch and took a seat at one of the tables. As I ate my lunch, I watched the local news that was playing on the television. I felt exhausted while I continued to eat, trying to preserve my energy. Once I finished eating, I went back upstairs to my office. I shook my head as I walked back into my office and stared down at the pencil and pad on the floor where I had left them. I walked towards my old office and knocked upon the door. Valentina looked up from her desk and asked, "What can I do for you, Kristi?" I responded by inquiring about what my next task would be. Valentina checked the clock and said, "You're just in time." "For what?" Valentina explained that she had a meeting with one of our junior executives, Thomas, and a representative of a client. I recognized the client's name, but I had never met its representative. "When is he coming in?" I asked. Valentina replied that they were already there and waiting up front to meet with her and Thomas. I nodded before Valentina upbraided me, "Don't sit there with your dick up your ass, go get your pencil and pad and meet us up front." I nodded, slightly turned on by her tone as I scurried towards my desk with my pained, constricted steps. It took me a good deal of effort to bend down again and grab the steno pad. Picking up the pencil from the floor was far harder as the tips of my nail extensions made it a struggle to wrap my fingers around it. After some effort, I picked it up. I stood up after some struggle, using Carol's desk for leverage again before I hurried towards the front conference room. I knocked on the conference door and Valentina called for me to enter. I smiled at everyone and greeted the client before Valentina asked him if he wanted anything to drink. The man requested a glass of water, which I happily obliged him by getting. I also got glasses for Valentina and Thomas before I took a seat at the table. It was an instant relief to sit down again, just as it was at lunch. My legs, feet and back were screaming. Sitting down to take down the key points from Valentina and Thomas's meeting with a client for a little over two hours was practically heavenly. I struggled to bite my tongue though, whenever I thought they were making a mistake. Still, I managed to let them conduct the meeting as they saw fit, knowing that it was not my place as a secretary to interject. When the meeting finally came to an end, less than an hour remained on the day. Valentina gave me a pen for the notes I took before she gave me my last assignment for the day. I nodded as I listened to the order. I had to start shredding the papers that I had left in a secondary conference room for Carol to shred a month earlier. The moment she gave the order, I knew that Valentina was doing it as a favor to Carol. Carol had been pushing me to hire a professional shredding company to get rid of the garbage bags full of unnecessary documents. I, however, had resisted it, noting that I had secretaries to take care of that type of recurring office problem. I'm sure that Carol relayed that response to Valentina, and that's why I was walking into the conference room to turn on the shredder. I shredded a fair amount of documents, but barely made a dent on the first bag, let alone the whole job by the end of business. By the time I left that room, I knew that I would be working on that pile for months, whenever Valentina felt that I had a moment to spare. I walked out of the room and saw Valentina. She waved over to me before she handed me a box of paperclips for my work shredding the papers. I thanked her before I placed the paperclips on top of the legal pad on the floor. I headed out of the office shortly thereafter. I went down to the parking lot and made the long walk to my car before I opened the doors. The pain in my body was intense as I got into the car and felt almost instant relief to be off my feet again. I then removed my heels and decided to drive barefoot. Despite all of the pain running through my legs and lower back, I could not help but also feel excited by the day's events. I could not understand why, but I tried in vain to do so. ----------------------------------------------------------------------- As the weeks passed, I kept earning more supplies by doing the tasks that Valentina