Corporate Ambitions By Ashley and Sarah Prologue As I relate this account of my incredible reversal of purpose, I cannot avoid a confused mix of emotions when I realize the clarity of my own recollection. It cannot be that it was so short a time ago that my passions were focused in quite another direction. Indeed, it seems a lifetime ago when my resolve was to be what I am fond of thinking of as "the other". I was a graduating MBA, mature but still somewhat young, and ready to launch what I knew would certainly be a "go-getter" career. I was graduating near the top of my class from a well-known "B" school, as we in the business world call such institutions. I was enthusiastic about my future, and to paraphrase a popular rock song, "My future was so bright, I had to wear shades." The time for interviews with prospective new employers had arrived, and I was quite sure of what would happen. You see, I had put my social life on hold, put my nose to the grindstone, even laid out big dough to get here. All to be in a position to choose instead of being chosen. Now it was payday, and things would be different from now on! I would not take a job with one of those blue chip corporations only to start as "associate something or other." No way! I would pick a company that would start me near the top, and it would be up from there. AND, I would leave a trail of tragic female conquests in my wake as I rose ever surely to the top of the firm lucky enough to have me ultimately as their CEO. Given my current circumstances, such ideas seem completely foolish to me now. My name is Heather Williams. I am the personal assistant to Rebecca Williams, the CEO of Women's World, LTD., a major corporation catering to women's fashion, cosmetics, lingerie, and such other needs as girls do enjoy. Rebecca has instructed me to write this story as part of my duties in my new job. A job that will be, I'm at once afraid and happy to say, is the pinnacle of my success. As I sit here typing this I am dressed in my usual style of work clothes: a short, tight, satin dress in red with dark silk hose reaching up my legs from 4" stiletto heels. My make-up is done to perfection, and the lingerie under my dress is satin and is simply exquisite. You see, there is a dress code here at Women's World, and all we executive assistants are required to abide by it. We are expected to portray the image of absolute femininity at all times. Rebecca and our relationship are unique in that she is my Boss, my Mistress, and yes, I am her Wife. In truth, I am a now a submissive transvestite slave to her. I'm sure you are wondering how I let this happen to me. Let me explain ... Chapter One I Gotta Wear Shades During my initial interviews with several large corporations, I was intrigued most by Women's World. The position being offered was executive assistant to the CEO. Talk about starting right up there! The idea of working directly with a CEO, along with a generous compensation and relocation package was more than I could resist. I shrewdly figured that working directly with the CEO would put me on the fast track to the top. I put a very good effort into this particular interview, and it seemed to pay off. Doris, the interviewer for Women's World was quite charming. I figured her for the Human Resources Dept. Director and not one of those paid recruiters. She seemed to know everything about Women's World, and I asked a lot of questions, priding myself on interviewing my interviewer. But I could not get a read on this one. Nothing I could put my finger on, but at times I swear I caught Doris trying to hide a smirk. Finally, Doris left me with a few encouraging words and a very large packet of material for me to fill out and send back to her. She said she felt fairly confident she could get my application "in front of" R. Williams, the CEO and, in this case, hiring manager. I had nothing keeping me in "B" school town. No wife, no romantic interests, no more promising prospects, so I said, "What the hey." I filled out and sent the information called for in the hefty package Doris had given me. I wasn't really surprised by the voluminous pre-employment miles of paperwork, given the position being offered. But I was a little curious about the requirement to include several photographs, and the specific emphasis on at least one full body shot. I just shrugged and thought, "Probably too many guys wearing jeans and sneakers while looking all business-like from the waist up." I wasn't expecting a response for a certainty, and when I received an e-mail directly from R. Williams/CEO I was somewhat surprised. The e-mail explained that my employment package was "impressive", and asked me to respond with a time that would be good for me to discuss the position available. My mind was reeling, as were my thoughts of even better chances of moving up the ladder fast. I e-mailed my reply immediately and set up a time for the call the next morning, if he could put me on his calendar then. "She" responded within an hour advising me of the time for our "teleconference". I was a little embarrassed to learn only then that R. Williams was a Ms. Rebecca Williams. I can remember thinking, "Hmmm, this is going to be easier than I thought!" The next morning the phone rang at the appointed time, and I nearly jumped out of my skin. I tried desperately not to sound nervous answering, being somewhat unprepared at such an early hour. But it only took seconds for her to put me at complete ease. Her voice was very soothing yet intensely commanding, as she led the conversation precisely where she wanted it to go. It seemed like only a few moments but it had been nearly an hour since we had begun talking and I was accepting her invitation to go to Florida for a second interview. The real kicker was that she had a corporate jet in town for business and offered me a free "hop" if I could go the next day. I was packed and out the door the next morning at the crack of dawn, heading for a private section of the airport. I was certain I was headed for greatness! The plane ride was rather uneventful, but it was the first time I had ever been on a Lear jet. My mind concentrated on the future that lay ahead, and my visions of grandeur were, to me, pragmatic and clear. I would land this job, then work myself into the graces of this Ms. Williams until I would be the new CEO. It seemed like only minutes but it was actually 2 hours till we were landing at a small private airport in Florida. The first of many pleasant surprises awaited me when I stepped off the plane and saw a limousine waiting to drive me to my hotel. Even more pleasant was the chauffeur, who had to be the most beautiful woman I had ever seen. Tall, blonde and gorgeous! The leather riding pants she wore made no effort to hide the most luscious derriere I had ever seen, and her black satin blouse likewise showed off a pair of beautiful breasts to their utmost. I knew I would love to spend time with this woman. Yet, like Rebecca, she was at the same time soft spoken and still somehow very direct. She welcomed me and held the door for me. "Nice touch," I thought as she sped us to my hotel in the powerful car. At the hotel, she opened the door for me once more, and told me she would meet me in the lobby the following morning at 8am sharp. Her face changed a little when she said in a voice that betrayed a hundred times, "Please try and not be late! Ms. Williams is irritated easily by tardiness." With that she was off, leaving me with a vision of her cute, wiggling ass and many female conquests that were yet to come. As I watched the way she moved, my eyes glued to her ass, I joked to myself, "Hmmm, two Volkswagen Beatles vainly trying to pass each other on the Freeway." I entered my room still wearing the self satisfied smile to find a chilled bottle of wine and a welcome note from Women's World that enthused how looking forward to meeting me they all were. "I could get used to this," I quipped out loud, as I stripped to my jockeys. I sat down and started going through the Dunn and Bradstreet report on Women's World, ticker symbol Ww (boy they had been around a long time). I had brought piles of reports with me on this company. I wanted to ensure I was really prepared for this interview. The more I learned about this company, the more intrigued I became. They were an acquisition company, but with a focus, it seemed. I was just piecing it together when the day caught up with me and I fell sound asleep. I was up at the crack of dawn, shaved, showered and in my best, neatly pressed Brook's Brother's suit. While waiting in the lobby for the limo to pick me up, I garnered all the enthusiasm I could muster. The limo arrived at precisely 8 and I was pleasantly surprised to see that my gorgeous blond chauffeur, Janie, had traded in her riding pants for a short, tight, leather mini- skirt. Talk about legs, this woman had some of the most gorgeous legs I had ever seen. I could only imagine where they lead. I figured she might well be my first conquest! Janie was the epitome of sexy and I was disappointed when we'd arrived at the offices of Women's World so quickly! We pulled into the sprawling Women's World headquarters campus at just 8:30, and Janie escorted me to the lobby. The building was rather unassuming for a Fortune 500 company, but that was nothing compared to the inside. It was very obvious from the dˇcor that this business was owned by and catered to women. There were light pastel colors and everything was so very "pretty". I remember thinking how I would change it once it belonged to me. The thing that threw me most, though, was that there didn't appear to be any men working there. Again, I was smirking. "Oh yes, this is going to be easier than I thought." The area opened into a kind of bullpen, with secretaries sitting in the middle, and offices around the perimeter. And, the women were all so beautiful. "My dumb luck," I mused, "to stumble into such riches." As the secretaries milled around, not one of them wore anything but a nicely tight, short mini- skirt, showing off their long, luxurious legs, which of course descended into sexy high heels. Wow! Everyone from the receptionist to the secretaries was attired thus. I was totally absorbed in a vision of all the fun and "bennies" I was going to have at this job. Just then, the receptionist snapped me from my reverie telling me in a stern voice, "Ms. Williams will see you now." I snapped out of it, shook my head, and focused once again, walking into her office. It was like any other CEO's office. Plush and very comfortable, with a singular exception... its decor was very feminine. Then the tall, leather armchair behind the desk turned around and I saw Ms. Williams for the first time! She stood to shake my hand firmly, and I had trouble making the words come out of my mouth. She was stunningly beautiful! She was wearing "the" classic, tailored, woman's business suit. While it was a suit, it remained somehow sternly feminine, if there can be such a phrase. It was all business, but still highlighted her charms to the maximum! I made her somewhere between the age of 35 and 40, close to my age, if perhaps a bit more sophisticated. And it was obvious that she took very good care of herself. No single word superlative I can think of to describes her combination of beauty and demeanor adequately. Statuesque, perhaps, comes close. I needed to remind myself to breathe! Taking the lead, she offered me a chair as she began. Just as on the phone, her voice was soothingly disarming. She had me at ease in an instant, with her easy charm. She asked me questions about my education, where I came from, and my career ambitions. She also told me a little bit about her company, most of which, I already knew. About half an hour into our interview she was called from the office on an emergency, and as she left, she told me to make myself at home and to check out "the surroundings." I could not resist. I got up and began looking around the plush office, thinking, "Someday it will be mine, all mine!" Walking to a table with some open boxes sitting on it, I saw what had to be some of the most beautiful lingerie ever conceived. "These must be some samples from one of the manufacturers," I mused, holding the dainty things up to the sunlight. I could just imagine what my chauffeur, or any of the secretaries for that matter, would look like in this lingerie. And even more so, Ms. Williams! I continued my explorations and picked up a pair of pink, satin panties and while admiring them, suddenly felt her standing right beside me! I dropped the panties immediately, blushing a bit. Ms. Williams, or Rebecca, as she had asked me to call her, laughed lightly and said, "Not to worry dear, we are in the lingerie business and know precisely how lovely these things are. You'd be surprised how many men we sell that kind of thing to." I stuttered my disbelief's and went back to my chair, scowling. Rebecca went back around her chair, and while standing behind it, smiled down at me. She took the back of the big, leather chair in her hands and asked in a disturbingly matter of fact voice, if I believed that men would buy such pretty things to wear themselves? I spat involuntarily that I couldn't believe it! She just looked at me quizzically and replied, "You would be surprised with the number of orders we send to P.O. boxes with addresses to only a first initial and last name. We've done some research and found that most of these orders are from men who want to remain anonymous. Now why do you suppose that is? We could care less, of course. Business is business, no matter who buys! As a matter of fact, I bet you would be extremely turned on if you would slide a pair of our silky panties up your thighs and around your waist!" I stammered that I most certainly would not! She looked at me with a wry smile and continued, "I'll tell you what, Mr. Smith." She said it with a touch of cynicism in her voice, "I have reviewed your resume and references quite thoroughly and I am impressed. However, I am still not convinced you are cut out for a business career with this particular company. What say lets make a little wager?" "Wager?" I stammered. "Yes, just a little wager. Since you seem to doubt my word about men buying and wearing panties like those pretty, pink, satin ones you, yourself were admiring, and since I can't afford to have an assistant working for me who doubts my word on anything, lets make a little wager. I want you to take a pair of our panties and go into my bathroom and put them on. If you are not aroused by the soft satin, I will give you a check for $50,000.00 and send you back home on my jet at my expense. But if you become aroused, you will work for me for an entire week, learning my business and doing exactly as I say. And..." she looked thoughtfully at me before finishing, "You will wear panties under your Brooks Brothers suits the whole time! At the end of a week, if you have proven to me that you no longer doubt my word; that you can without hesitation do what I ask, and we both agree on it, I will offer you the job as my executive assistant. The pay is $150,000 a year to start, plus benefits, plus relocation package." "To make the bet even sweeter, if you do win, I will give you two nights with my gorgeous chauffeur, Janie. I know you liked what you saw, you are a normal man right? And every normal man lusts after that beauty. Well? What do you say Mr. Smith? Oh and by the way, I won't watch you change. You can lock the door and after you change you will come back out into my office and sit with me chatting for a half hour before the decision about your arousal is made, if it takes that long," she snickered. Then she came around from behind her chair and settled back into it, looking at me with an evil grin. I just sat there thinking. Why not take this bet? I may not get the job, but $50 K free money and a ride back home, and most of all, two nights with that gorgeous babe chauffeur! I couldn't lose! Look at it as a paid gambling trip where I got $50K and laid to boot. I could do this, it would be easy! I looked at Rebecca and choking back a laugh, said, "You're on! I'd like my $50,000 in cash please." I expected Rebecca to get up and hand me the satin panties I was admiring before. Instead, she pulled open a desk drawer. I will never forget my chagrin as long as I live. She pulled out the prettiest panties I had ever laid eyes on! They were pink, and all satin with big ruffles at the waist and legs openings, and tied on with satin ribbons. This meant that I would actually have to work at putting them on. Not just sliding a garment up my legs, but I would have to tie bows at my hips. As she handed them to me, she firmly restated that I had 3 minutes to get the panties on and be back in her office with nothing around my waist and crotch but the panties. Her eyes were mocking, while I realized I hadn't noticed before how tall she was. She rose from her chair, and pulling herself to her full height, held the mischievous garment daintily between her thumbs and forefingers, tauntingly. The expression on her face said that it was not her practice to hold panties in such a way. I indignantly snatched the panties out of her grasp and headed to the adjoining bathroom thinking, "This is the easiest 50 thou I would ever make! Closing the door, I took my pants and socks off, then came my Jockeys. I held the panties up and then tied bows where I thought they should go. Then I just stepped into them, pulled them up my legs and began settling them into my crotch. Turning around and looking in the mirror, my pride suddenly vanished as I felt and saw my cock begin to rise of its own accord, filling out the front of the panties. I panicked! I grabbed my cock and squeezed it hard, trying to make it subside. All this did was to arouse me more. What was I going to do? I had only three minutes to be out or I would lose, but going out like this was a sure loss also. What would I do? Fussing with the infernal satin straps at my hips, I'm afraid I wasted a lot of the precious three minutes. As Ms. Williams knocked at the door I knew my three minutes were up! "You can either show me you're not turned on, or admit defeat," came Rebecca's voice from the other side of the door. "Well? Was I right or not?" the impatient voice insisted. Her tone made it clear she already knew the answer, and seemed to drip smugness. I had never been so humiliated! I was trapped! I could not show her my now raging hard-on, and I certainly wasn't going to give her the satisfaction of seeing me with the ruffly panty tied across my ass with a big bow at each hip, no less! "OK, you win," I admitted. I wished my voice were not quite so sheepish. "Get out here, Heath! Or is it Heather, now?!" she mocked. "OK, so I lost the bet," I confessed, as I hurriedly pulled my pants on. I was so flustered; I didn't know what to do. I hesitated, took a breath, then finally opened the door and came out. I tried hard to look casual about the whole thing. "The terms of our little wager were for you to show me how you are not turned on by the feminine lingerie this company sells. I hope I have made a point, 'Mr. Smith,'" she chided with a particularly sarcastic emphasis on her use of the masculine title. I knew it could be a long time before I would get a respectful "Mr. Smith" out of her again. Rebecca continued, "We sell these things to make money! As CEO, I care a lot about our bottom line. But I think you are a good sport! Welcome aboard, you're hired!" I was embarrassed and thrilled all at the same time. Red faced to have been maneuvered into making the silly bet, and losing! Thrilled to be offered this kind of money and a position so near the top of a big company. But I was still wearing those teasing panties under my pants. My still stiffening cock strained hopelessly against its satin crotch, making the elasticized leg openings tighten a little more across my ass. Oh, I was more aware of my ass than I had ever been in my life. Finally I offered, "I will accept the job on the condition that you release me from the consequences of our wager." Rebecca's face grew into an exaggerated look of pretended dismay. "A bet's a bet," she smiled knowingly. "You wouldn't welch on a bet, would you? I expect you to be properly pantied for the rest of the week, and I want no lip about it! These terms of our wager you agreed to separately, and my offer of EA stands on its own. Have we a deal, then?" She stood with her hand outstretched. A lifetime seemed to pass before I returned the handshake- her grasp was firm, and the deal was done! "Good," she said as though dismissing me. "Now get down to lingerie manufacturing and pick yourself seven or so pairs of panties. I can't have my EA wearing the same panties all week long, now can I?" I was horrified! "ME?" I eeked. "Me get panties? I have to do it?" "Yes, and by the way, we'll be having dinner tonight, say around 8," she said flatly while writing something into her appointment book. Then, looking up from her desk, "Is there something else?" "No, ma'am," I heard myself say. Where was the lingerie factory? Chapter Two From Shades to Panties I had been hired, and pantied all in a matter of mere minutes. What was going on? Was this Women's World company getting the better of me? Me, the big MBA, who would certainly turn the business world on its ear? I was sure I was ready to take charge in business, but in the course of events I had been given a first assignment to get myself panties from a lingerie manufacturing plant! Where was our lingerie manufacturing plant, anyway? And what about my office? I quickly called Doris in HR, and explained that I was accepting a position with the firm. I threw in, for the benefit of my damaged male ego, "If you have any questions about it, please speak to R. Williams!" I was so macho! "That'll carry some weight," I thought. Doris kept breaking off, seeming to have someone else on another line. There must have been something terribly amusing going on in that other conversation, she kept chuckling every time she came back. "Where is my office, anyway?" I asked, irritated with all the interruptions and giggling. "And where is our lingerie factory, I have an assignment there." Doris let me regain my composure before she hit me with the next bombshell... "We'll take care of your office when you get back. And the lingerie factory is in Paris!" Damn her laughter! "If you get the Concorde, you have just enough time to do your 'assignment' and get back in time for dinner with Ms. Williams." "How did you know about that?!" I demanded. Doris just told me to get down to the street, that the car was waiting for me. I could not believe this was happening but I had to go through with it. When I got to the street, sure enough, there was Janie, waiting in the long, sleek Limo. It was comforting to see her now familiar face. To my surprise, she seemed to know all about things. "That's a good girl," I thought to myself as she rambled on about how I could walk right onto the Concorde, all the arrangements had been made. "First class, of course, Mr. Smith." Again emboldened, I threw my body over the seat to sit next to Janie as she sped us to the airport. God, she looked hot! Janie had legs that went from here to there and back again! I couldn't stop myself from putting my hand on her helpless right leg, which was busy working the pedals of the car. That long leg, encased in black nylon was just begging to be stroked, I thought. When she let her already too short skirt ride up like that, I took it as an invitation. Pretty soon she was moaning softly, and I felt better. My manhood restored, we had arrived at the airport. The Women's World corporate jet landed in New York City and the transfer to the supersonic Concorde, true to its nature, was very quick. It was as though they were waiting for me. I was surprised at how small and cramped the Concorde really is, even in first class. But the trip was fast, and I was still recovering from the events of the day, when we touched down in Paris! Women's World, also true to style, had a waiting Janie counterpart in Paris to whisk me away. "All this, just for panties?" I mused. "Certainly, it's Rebecca's way of showing me the international side of the business. A business that will soon be mine!" Toni was Janie's European counterpart, and she picked up right where Janie left off. Legs to die for, and I put myself in the front seat next to her like I had been doing it all my life. Pretty soon, I had my hand on her leg, too. Toni didn't speak English very well, so I forgave her for constantly referring to me as Ms. Smith whenever she asked me to stop that. It was only when I thought about whipping out the hard proof of my manhood that I remembered about the frilly panties I was wearing. I had stop, but there would be others like her, I thought, many others. I wasn't sure what I was supposed to do, business wise, at the lingerie factory, but I supposed I would just look cool and figure it out from there. Meanwhile, I would pick up a few things to satisfy my bet with Rebecca. I was determined to pay the debt, and definitely to get her back someday. She would be surprised when I pulled a coupe and took over her company! I thanked Toni for the ride and for holding the door for me as I went in. All the while I was thinking, "Once I get out of these panties, baby, look out!" Now I had two, no three female conquests in mind. Two chauffeurs and one CEO. How easy in the case of the former; how appropriate in the case of the latter. Women's World, Paris, LLC, was impressive. I was received by a gaggle of girls all dressed in the cutest French maid's uniforms I had ever seen. Pretty, black, satin edged with the daintiest lace at the bodice, sleeves and hems. Their little poofy skirts were all pushed out by unthinkable volumes of petticoats: all there to show off some very well shaped legs, which were encased in the most elegant, sheer, black nylon stockings. Just out of view, those stockings were being drawn taught by the black satin garters that surely were there. "You have a nice flight, Ms. Smith? Lunch time now, no?" Not another one! But, they began serving me like a king, so I decided to let their insubordination go. But I made a mental note of it. Finishing lunch, I copped a few feels of the servant girl's cute asses. They seemed even to enjoy it and did not discourage me in any way. I was constantly reminded, though, of the cursed feminine panties that I myself wore beneath my male clothes. I would have to make sure to pick up some samples here, to satisfy my bet with Rebecca. How I began to hate that bet! Lunch over, it was time for my tour of the Paris plant. Chapter Three Rude Awakening Women's World might have been run by Rebecca, but the Paris plant sure as hell was run by Magdalene. Magdalene was a very stern looking woman. The minute she showed up, all the other girls pulled the plates and glasses off my table so fast it almost made my nose bleed. Lunch was over, all right. Magdalene introduced herself as the head of the shop, here in Paris. Maggie, as she insisted I call her, was clearly in charge of this place. "We, here at the lingerie manufacturing facility of Women's World," she prided with unmistakable authority, "know exactly what the men want. We cater to those wants, and our margin has improved by orders of magnitude. Your boss and mine, Rebecca Williams, knows how to market and knows what sells. She tells us what to make, and we make it very well with the inexpensive labor available to us. Now put this on so we can tour the shop!" Maggie was handing me a set of shop clothes, very similar to the ones she wore, and all the workers wore, as I could see from the vantage point of the window I now peered through. When she still stood there, I explained that I would be happy to wear the standard clothes of the shop floor, but that I would appreciate a little privacy. With that, Magdalene gave me such a look! She seemed to look right through my clothes-did she know? Impossible! Thankfully, Maggie left me to put on the shop uniform. I pulled the pants on and was surprised to find that the zipper was in the back, and to make matters worse they were made of a lycra type material, almost satin, and the color was a medium shade of pink. It made me even more frustrated, if that were possible, to think how only girl's pants zip in the back! My male ego told me, "Well, at least I was still wearing pants!" Then, I pulled the top over my head, it was also of a very girlish style - puffed, short sleeves, loose at the top and hugging at the waist. "I can't wear this!" I said out loud, as Maggie came into the room. "Come on!" she urged, "You need to be back in New York tonight for dinner with Ms. R. Williams!" Tugging me by the arm, Maggie dragged me out wearing this poofy, girlish uniform. My panty lines were very obvious to anyone who cared to look at my ass! I was mortified! But soon, Maggie was showing me the labor that went into making the sexy lingerie that I had always believed was a silly thing that only girls liked. "Silly girls who I would conquer would wear such things for me!" I reasoned. But now, I would be wearing them for a whole week! "The bet!" I remembered. As we passed by the sewing stations, I picked up a few sample pairs, trying not to look at them too closely. I could not wait for the end of the tour of the shop. Being dressed this way, and following Magdalene like I was her puppy was getting my goat. But the place was loaded with pretty girls, all making fabulous lingerie by hand. They seemed to love their work, each one taking such care to get everything perfect. Fussing with the expensive patterned material to get every seam just right, they were, every one, perfectionists. I could not help but be impressed with this Women's World Company I had joined, but there was no way this was "inexpensive" labor. Any one of these girls could have been a model herself! Maggie explained the operation, while copping an occasional feel of my pantied ass. She seemed to do it whenever she was sure someone was looking, which unnerved me a little. I couldn't blame her for being attracted to me, but did she have to be such an exhibitionist? Still, somehow it was turning me on. At one point during the tour she was behind me and she grabbed my waist and leaned her crotch tightly into my panty and Lycra covered ass, much to the amusement of several girls who were watching. At last, the tour was ended, and we were back at its starting point. I asked Maggie where my clothes were, anxious to change back and get going. Maggie gave me a real strange look, then. "Want your clothes, girlie?" she asked with a growing smirk. I just stood there in disbelief. "What did you say?" I shot back! "Do I have to spell it out for you? A real man would never allow himself to be pantied and dressed as you are now," she said in disgust. She put a special emphasis on her unusual use of that word as a verb, "pantied". I nearly swooned, trying desperately to keep my head. I was now separated from all of my male clothes. Maggie was clearly enjoying this as the realization of my situation sunk in- then she pushed hard against my body, shoving me into a wall. I was unable to resist her strength. That was when she pinched my nipple hard! I should have said ouch! I'm afraid I let a soft moan escape my lips and visibly weakened. God, I was so hot! When I was able to breathe again, all that came out of my mouth was "What are you doing?! Where are my clothes!" Maggie withdrew, and with a smile that belied experience, she said, "You little sissy! You like it, you pantywaist! You want to be a sissy? Where are your clothes, girlie?!" she jeered. Then she looked behind her, and I knew something was terribly wrong. As my eyes focused, there on a table were the clothes of the fifi maids who had served me lunch! "Hurry up, sissy! You have about 14 minutes to put that on! Move!" I wish I could tell you I had the will to resist, but somehow, I was rendered submissive by the events of this particular day. I was in a foreign country, and alternately being ravished and yelled at. Discretion is the better part of valor, so I decided to do as I was told if only to get back to America. Then I would be in control again. Maggie made to strip out of the shop uniform right in front of her. Right down to the ultra-feminine panties that I had obviously been wearing when I'd arrived. With Maggie watching, my growing cock was giving me away again, the disloyal thing! Was that a cell phone she was on? She gave me some wolf whistles when I started dressing in the maid's costume, and I deeply resenting her watching. I wondered if I were secretly thrilling to do what I was now being forced to do. There was no mistaking, or hiding for that matter, my state of arousal. "Move, I want to see a big, strong man become a sissy!" Maggie insisted, with an all too sinister sneer on her face. First came the black satin garter belt, the one I knew was under the maid girl's dresses who had served me only minutes before. As I snapped the garter belt's snaps behind me, I wished I could hide my telltale engorged cock! I rolled the heavy, black nylon stockings up one leg, then the other, finally snapping the clever little garter devices into place. These stockings were thankfully heavier than the sheer ones the maid girls had worn, effectively making my hairy legs look smooth. I had the feeling that Maggie would have shaved my legs, otherwise. I put my arms through the black satin bra, but by now my hands were shaking. I was actually grateful when Maggie pulled it taught behind me and hooked it. She then placed some breast forms into the bra, they must have been at least 38 D's, and I could no longer see my feet. She took over pretty much then, and floated a soft, black, camisole over my head. The cool, satin material made me shiver as it floated gently down my torso and settled over my now bra'd bust. "You want this, don't you, sissy?" she smirked. "What's that? I can't hear you," Maggie was now yelling in my ear. I was so tormented, I forgave myself as I answered meekly, "Yes, Ma'am!" "Good girl!" Maggie bubbled with glee. "We have just enough time." She picked up the voluminous white crinoline petticoat and started stroking my raging hard cock with it through the panties. "Why don't you put on your heels, dear? If you agree to be a good girl, I might even give you a special surprise." I was so hot I would do about anything for my imagined surprise- so I put on the high heels and even took the petticoats from her inviting hand and slid the feminizing garment up to my "girl" waist. Oooohh, how I loved the feel of it on. Things began to take on an aura of the unreal. "Good girl!" Maggie was now openly laughing at me, and several other girls from the plant had come in, their shift seemingly ended. I didn't care! I was so hot, I would have done about anything for my "special surprise"! "Tell all these girls how you like our products, then! Tell them, what you are and what you like!" Maggie demanded. "I'm, uh, a sissy," I was saying. I couldn't believe it was me as I continued, "I like to wear pretty, girlie panties. Thank you ever so much for the samples." With that, most of the girls giggled, some just nodded. I thought I saw some high fiving one another. "Are you ready for your surprise, Mr. Smith," I heard Maggie say? My torture, I hoped, was over. "Yes, since you have been such a good little girl, you may wear your new uniform all the way home. Won't Ms. Williams be pleased when she sees how willingly you accept your new status in life! Who knows? Maybe she'll even send you back to us." As the girls looked on, tittering, Maggie held out the dress! I pulled my wobbly arms though the puff of satin sleeves and the all too short dress floated down my body and settled delightfully over the frilly petticoat. Maggie said while zipping the back, "Time for you to go home, pet! But first..." she turned took something from one of the tittering girls. "Now for your surprise," Maggie delighted, pulling a cute short wig onto my head. She fussed with it for way too long and to my horror, I realized she was tying dozens of tiny pink ribbons into bows in my new feminine hair. I was astounded and panicky. I would have to go home like this?! How would I explain? What if someone saw me? I was ever more embarrassed to remember that I had to walk back to Toni's car. I nearly fell on my ass walking in high heels for the first time, and I had no idea of what to do with my hands. Each time I put my hands naturally at my sides, they fell on the soft, cool pile of the satin dress encircling my waist, the dress being held out by the scads of crinoline petticoat. Each time, my male sensibilities made me draw my hands back involuntarily. There was nowhere for them to go! Maggie explained that I must take very short steps and hold my arms out a little from the elbows for balance; that it would certainly be impossible for me to walk with my normal male gait in high heels. I must have been quite a sight when I came mincing out, heels echoing on the pavement, arms bent delicately and fingers held out to avoid touching the offensive satin swirling about my hips. With each tiny step, the petticoat tickled my stockinged thighs and seemed to tease me into a never ending, escalating state of arousal. For the first time, I could feel the coolness of a gentle breeze blowing unencumbered up my dress. I had never felt more exposed! When we got to the car Maggie spun me around and planted her lips to mine and gave me a soul-searching mouth kiss, her tongue forced my lips to part and delved into the depths of my mouth. All the time her hand was under my short skirt stroking my engorged, trapped cock. She released me from the kiss and told me, "We are going to have so much fun when Ms. Williams sends you back to visit us!" I got into the car rather ungracefully, petticoats all a-fly, and undeniably exposing my pantied derri¸re one last time. Maggie tossed the samples I had gathered through the door behind me with a hearty, "Don't forget your daywear!" and shut the door. Toni had a very satisfied smile indeed, as the pretty French maid, that was just minutes before, Mr. Smith, climbed into the back of her car. Toni drove and remained silent, but all the time she had this grin on her face. I was just beginning to think I would be spared more torment when she crooked the rear view mirror, and asked with a mock innocent air, "What's the matter, Mr. Macho? You don't want to jump over the seat to put your hands on me now, no?" With that, she abruptly stopped the car along the road. I had no idea where we were. Now it was she climbing over the seat, and the next thing I knew she had her tongue down my throat and her hand running up and down my stockinged legs. "So aloof now, are you?" she hissed in my ear just before she put her tongue in it while roughly pulling my hard cock through a leg opening of my sexy panties. She had one hand squeezing my cock, and the other was deftly pinching one nipple through my bra. I did try to push her away, but somehow I became weaker and weaker in her stronger and stronger embrace. I wanted to get out of the car and run away when she started asking me embarrassing questions while she toyed and played with my rock hard erection. It was as though she was seeing what effect her questions would have on my cock. "You are a sissy bitch, yes?" she suggested. "You want to learn what it's like to be tamed?" I wished she would stop licking my ear and please make her stop kissing my neck like that! Toni knew what she wanted, and she knew how much time she had left to be at the airport on time. She just pulled her pants down and shoved her musky pussy in my face. "Lick me, mademoiselle sissy bitch!" she commanded. I gave several tentative slurps to her pussy. Toni pulled her pants off the rest of the way, and pushed me down further into the seat of the limo. She kept reminding me as I licked her pussy with growing fervor- "You are the one now, who's wearing a dress, nylons, and high heels. You are such a sexy little thing. How do you like it? The shoe, er, pump is on the other foot now, isn't it, you pussy-licking slut!" Toni was making me give her pleasure without my getting any pleasure of my own. Was this what girls go through? Wait! I am not a girl! But she was not about to allow me to even pleasure myself. When she saw me trying to rub my cock with all those rows of ruffles, she pulled my hands over my head and pressed down hard on my lap with her all of her weight. I couldn't even pump my cock in the air, and she laughed when I tried. A company chauffeur was humiliating me, and there wasn't a thing I could do about it. Toni looked much happier when she dropped me at the airport than she did when she'd picked me up. Her parting words were, "I hear you have a dinner date tonight with Ms. Williams. Have you picked out a gown yet, sissy boy? Huh?" I was really glad I wouldn't have to go through any airline passenger check- in line, and I wished desperately to change out of this degrading costume. I would have to ride the Concorde dressed this way, and how would I explain it to Rebecca were she to hear about this? Oh no! I still had to face the other chauffeur, Janie. I thought it was fun to look up her skirt and said as much. Now I guessed I'd be finding out what it's like. The trip back on the Concorde was rather uneventful, unless you consider the fact that here I was a male dressed in a frilly maid's uniform, my hair coifed with a short blonde wig and my penis held captive in satin panties. I might just as well have been wrapped in chains and locks, I WAS TRAPPED. On the plane the only unexpected thing that happened was that a beautiful woman sitting beside me remarked she thought it was so humorous that I would go to such lengths to please my husband/boyfriend who would undoubtedly be waiting for me with the airplane landed. She actually thought I was a GIRL!!! Which is more embarrassing, I wondered, to be made as a man in women's clothes or to pass as a girl? I breathed a sigh of relief when the plane landed and I could run off to catch the connecting flight back home on Women's World's private jet. Once the company jet had left LaGuardia I was finally able to relax a little and try to figure out what exactly had happened to me and how to get out of it. And I hated to admit, even to myself, but entertained thoughts known to only me: how I really enjoyed the silk and satin prison I was trapped in. My cock had never been so hard! I leaned my head back and closed my eyes, trying to vanquish such thoughts and sleep on it. Suddenly, I was brought back to reality when a woman's voice next to me said, "Something to drink ma'am?" I opened my eyes to see Janie!! There this vision of beauty stood before me. She giggled hilariously as she spoke, "Well, I see our Mr. Macho is really a pretty little sissy at heart," as her hand snaked underneath my skirts and rubbed my imprisoned cock, again bringing it to full mast. She calmed herself a little and explained that Ms. Williams had sent her to New York to meet me. She said she was advised that she would either have a 3 hour "sucking and screwing" session with a real man, should I turn out to be one, or else 3 hours to get me properly prepared for my dinner date. Should it turn out to be the latter, she was expected to "explain" to me how my life would be from now on. She giggled again, noting how glad she was that it was the latter of the two that she found. "Come now, Heather, we only have a short time to get you ready." Chapter Four Complete Makeover Janie stood in front of me for a minute with her hands on her hips and a look of triumph on her face. She seemed to be studying me. When I looked up at her, all I could remember was how soft and hot her thigh had felt under my hand just hours ago. Her face broke into a broad, pretty smile as she spoke, "What? You don't want to run your hand up my leg and under my skirt now Mr. Macho? Or should that be Miss Sissy now? Yes, I think it is now Miss Sissy." She said it with so much sarcasm in her voice it stung all the way to my toes. She explained that Ms. Williams had bet that I would take the course that I had taken. And that now that I had made the choice to follow the path to being a beautiful sissy, it was her job as Ms. Williams' "personal trainer" to ensure that I went down the road with the proper attitude, demeanor and look. Just like she had done with all the others. That last statement sent a chill down my spine. I looked at her in shock as she went on to explain that yes, Ms. Williams had done this same thing to other males, but that was not to be my concern now. She was no longer at liberty to discuss company business with me. I was to be concerned only with the present and to simply listen closely to what she said. I was to follow her every instruction closely, from now on, as if I had any choice. "Oh, yes," she pledged, lowering her voice, "not all go willingly. I'm glad to see you're not one of those." Janie just looked down at me from her superior position and ordered me to rise and turn around. I did as she had instructed, wondering why I didn't just revolt and tear these silly clothes off! I should be showing her I was a man, not some obedient little wimp. Yet, I seemed to just blindly follow her instructions, not even raising any objections. She pulled me closer and unzipped the dress in the back, pulling it off of my shoulders and letting it fall to the cabin floor. Next came the frilly crinoline. Suddenly I was standing there in just my stockings, panties, garter belt, bra with huge breasts jutting forward, and a pretty camisole. Seeing her in her short, tight, leather mini had also left me with a hardon that was unmistakably poking the front of my panties out. "My, don't you look so pretty?" she teased with now familiar sarcasm. Then before my widening eyes, she began to unbutton her satin blouse, exposing her gorgeous breasts caressed, as they were, in their lacey shelf bra. I thought they would spill out at any moment. Reaching behind her she unzipped her little mini and let it fall to the floor, leaving the unmistakable smell of leather in the air. She kicked it onto the pile with my dress and crinoline petticoat. She was wearing only the briefest of black satin panties, which she slid off of her waist and over her thighs. Looking at me she put her hands on my shoulders and pushed me to my knees. "You have made me so excited, 'Heather', I must have some of you before we continue." She pushed her pussy in front of my face tersely, and I could smell the musky pleasure that lay between her thighs. I leaned forward and tentatively licked her pussy. Janie moaned a little, and grabbed my head, draping one leg over my shoulder so that I nearly swallowed her hot, wet pussy whole. "Be a good little sissy bitch and lick my hot pussy, girl!" she cried. I had no choice, other than suffocation, so I obliged her demands. It occurred to me that I had no desire for another choice. I licked her till she had four orgasms, yet she was still ready for more. But she knew time was limited, and Ms. Williams was very unforgiving of tardiness. Satisfied, she pulled away from my juice soaked mouth. My makeup, what little I was wearing, was totally messed, and my cock was throbbing and had left a huge wet spot on the front of my panties. She leaned down and gave me a deep French kiss, her tongue forcing it's way into my mouth and seeming to penetrate me there. Her kiss was more than a mere kiss, it was like a little fuck. I felt so helpless to avoid her demanding tongue, it seemed to compel my very soul to open, widely, willingly. To submit. I was dazed when she pulled me to my feet, and then sat in one of the comfortable chairs in the cabin, studying me again. She pulled my panties down and my maleness sprang forward, nearly hitting her in the face. Pulling them off completely she draped them over my hard cock. "My, look at your pretty little clitty. It's is so hard and excited, did I do that to you, Heather?" I was a bit taken back by her referring to my manhood as a clitty, and my name was not "Heather". As alarmed as I was, my urgent need was screaming from my loins and overtook any anger I may have had. Anger, you see, being mixed into the stew of emotions and physiological takings place as my poor body had endured this day was not an option. Taking the silky panties and draping them over my hard cock, she looked in my eyes and smiled. "Does my pretty little sissy want to cum for me"? "Yes," I mumbled. "Are you a pretty little sissy boy, who likes, no, needs to dress in pretty lingerie and dresses?" Try as I might to not admit to such a foolish thing, what she was doing to my "clitty", I mean cock, was driving me wild. I needed to cum so badly that I just said, "Yes, I am a little sissy boy who needs to dress in silky, frilly lingerie and dresses. I want, no, need to be a girl for you. Please let me cum?!" "Will you do what ever I may ask of you, and I mean anything, without question? And will you wear exactly what I tell you to wear? And will you always obey the women in your life, like a good little sissy girl?" "Yes!" I screamed, "Whatever you say! Please just let me cum, PLEASE?" "Very well then, Heather," she smiled as she draped the silky panties over my jutting pole. She left the sexy garment hanging there over my cock like some obscene flag. "You may put these back on and cum like a girl. Use only your fingertips, like this." I looked up at her mesmerized, as Jeanie pulled her own sexy panties on and began to rub her crotch. "Fingertips only, like this." I pulled the panties back on and knelt before her, watching her example. Touching my hard "clitty" with just the ends of my fingers like she was. "Oooh, Heather, doesn't that feel good? Gently stroke your clit through the sexy fabric. MMmmm." It didn't take long, especially since you consider that I had been horny and excited all day long, for me to begin to orgasm. I felt it start from somewhere deep within me, the mounting pain that longs for release, the itch that cannot be scratched. It all overtook me in a rush, and washed over me in wave after wave of sheer ecstasy. Soon, the panties were discoloring as hard spurts of cum tried with classic male arrogance to shoot through them. Janie came too, smirking at the growing wet spot at my crotch. And then I collapsed onto the floor, breathless. When I finally regained some composure she was standing over me, having replaced her panties and bra, and she was smiling down at me. She reached a hand to me to help me to my feet and once there, she ordered me to strip completely. "We have a lot of work to do on you and not much time to get it done. Ms. Williams, your new owner expects us shortly." I should have been alarmed, I should have been aghast at her use of the word "owner". But I was too weak to make such objections. I felt owned. After I had stripped completely I felt so completely helpless in front of her. She began by spreading some kind of pink lotion all over my body, which did not smell too good and soon began to burn slightly. When I questioned this Janie told me it was one of Women's World's latest products, intended to take all my hair off, permanently. "Have you ever seen a hairy sissy girl? We've developed our products, let's say, with a certain audience in mind." I was to find out that this jet had all of the amenities, there was even a shower, albeit a little cold. And though I hadn't chosen to, I was standing in the shower watching the cold water wash all the manly hair from my body, forever, according to Janie. Stepping from the shower she stood there with a towel and patted me dry. Standing back, Janie smiled her approval at my now hairless body. I shivered in the cool air of the cabin and felt goose bumps begin to rise. Seeing her I also began to get excited again, she was so sexy again in that black leather mini-skirt. She handed me what appeared to be a heavy satin thong panty. It was a Lycra "cache panty" as she called it. She ordered me to put it on, and I once again just blindly obeyed. As I pulled it up my now hairless legs and over my hips she reached down and pulled my "clitty" between my legs and pulled the panty up tight. "We wouldn't want a silly bulge to ruin the lines of your pretty dress, would we?" I could only shake my head no. Then Janie started in earnest. First, she handed me a pink satin garter belt, which she attached around my waist. "Pink is for girls," she mused while hitching it behind me. Then she handed me a pair of tan silk stockings and watched as I pulled them up my new smooth legs. She watched me struggle briefly with the garter straps then came to my assistance, "I will not help you do this always, I am only helping in the name of saving time. You will learn to do all of what I will do to you by yourself and I expect you to become proficient at it!" I could only stand and watch, I wanted to break down and cry, yet I could feel myself beginning to get excited underneath the restricting cache panty. My erection pushed harmlessly at the entrapping sheath. Janie seemed to expect this reaction and patted my crotch lightly, seeming to brag, "See? You're all nice and flat down there. Just like all the other girls!" Next she gave me a pair of frilly pink satin panties that hugged my bottom and waist and looked so flattering. She ran her hand up the front and smiled, "See? No nasty bulge to have to deal with, only nice and feminine." Next she produced some breast forms and told me to lay on the couch, which I did all too willingly. I watched as she rubbed some sort of lotion into my breasts and then on the inserts themselves. I nearly passed out when she came to me and placed the inserts over my own nipples and pushed them securely in place. "Don't move for 10 minutes while these set up, yes it is nearly permanent glue. Only Ms. Williams and I have the dissolving solution." Then to add to my distress she smirked, and told me "These will give you that feminine shape until your real ones grow, if that is what Ms. Williams decides for you." After the glue had set she helped me to my feet, I felt so off balance with the new weight suspended from my chest, and I could feel them vibrate or wiggle with every move I took. I got a kind of thrill from feeling it, like nothing I had ever felt before. I found myself wondering what she meant by, "until your real ones grow." Surely, they couldn't do that. She had me slip my arms through a matching bustier. The bustier helped hug my waist a little and held my new breasts close, suspended straight out in front of me. Next came a matching satin slip. I was relieved to be putting this on since it offered me some sort of modesty, even though it barely cleared my pantied bottom. But when I felt the silky material floating over my thighs and ass, my cock was again straining against its luscious prison. Next, she produced a pair of 4" heeled stiletto shoes. The shoes were a pink patent leather with an ankle strap securing my foot to the shoe. "I can't wear these!" I pouted. "You not only can, you will and you will always wear a high heel similar to these. How do you expect to become a perfect sissy girl for Ms. Williams if you don't wear these pretty high heels? And besides you will learn to love them. Now sit at my vanity so that we can get your makeup done, time is running short." I meekly stood, nearly falling in the new heels, and stepped to her vanity. Janie draped a towel over my shoulders, to keep my pretty lingerie clean, she said. "You will pay close attention to what I am doing, you will be expected to make yourself pretty by yourself after this." I could not believe what was happening to me! Here I was, sitting at a very sexy woman's vanity wearing all this silky lingerie, my cock was trapped in the cache panty and I was basically sitting on it. And this gorgeous woman, who only hours ago had my hand on her shapely thigh, was putting makeup on my face telling me I would have to do this myself in the future. This could not be happening! Secretly, and deep down inside, I loved it. Did it mean I truly was a sissy? I would get out of this somehow, and rise up to be a Wall Street Wiz yet. Unfortunately, such thoughts running through my head caused me to misappropriate my attention to what Janie was doing to me. She surprised me by suddenly she spinning me around to look in the mirror. I could not believe what I saw! There was a beautiful woman looking back at me! This could not be me, I thought, and then looking at Janie and seeing her smile of approval, I knew it not only could be, it was! I would have come on to this girl in the mirror, and she was me. In fact, I was blushing furiously to think that she was turning me on! Grabbing my hands Janie quickly glued girlish fake fingernails to my own, about 3/4" long, and painted them the same shade of pink that coated my lips. While the nail polish dried I was able to watch her get dressed again, sorry to see her cover any of her body. Regret, I was tasting it in so many ways this day. Then she went to the closet and brought out the prettiest white satin dress, I think I have ever seen. I could tell though that it was short and tight. Standing in front of me with the dress in her hands she smiled and said, "I do think you will be the loveliest sissy girl in this dress, don't you, sweet Heather?" I could feel the blush rise in my cheeks and much to my chagrin I could also feel my trapped cock begin to stir again in its satin prison. Standing me up she slid the dress over my head and past my pseudo breasts to let it float down my body. I registered a nine in the Richter scale. Once it was in place she zipped up the zipper in the back and I could feel the dress wrap itself around me, it was very tight. I thrilled at the new feminine feelings, and began to fall in love with them. Taking my hand Janie led me to the full-length mirror and I could not believe what I saw, I was a beautiful woman! I could also see that if I bent over just the slightest my garters and panties would surely be seen by anyone who may be looking. I looked at my Janie with pleading eyes, "Please don't make me wear this to Ms. Williams dinner, I don't think she would approve." Janie laughed and hugged me tightly and said, "Of course she will approve of you silly, sissy girl. She bought the dress especially for you." Just as the Lear Jet landed, Janie handed me a matching little purse. She said the purse contained all the necessary items a sissy like me would need, such as lipstick, blush, other makeup and of course a sanitary napkin, just in case, and headed toward the door with me in tow. When we got to the limo, she once again held the door, only this time the front door on the passenger's side. I eased into the front seat as gracefully as I could even though I was sure I was giving Janie a beautiful shot of my panties while I did it. "You'll learn," she chuckled. She got into the driver's seat and patted the seat beside her and said, "Come sit beside me, pretty sissy girl!" I moved over next to her and she immediately had her hand on my stocking covered thigh and was moving it under my dress. She teased me this way all the way to Ms. Williams' estate, knowing full well that she was putting my trapped cock through pure hell! Thankfully we arrived at the mansion before I had an accident. I never would have thought that I would be grateful to see the place where my life as I had previously known it, would end. Chapter Five Indoctrination - New Rules When the car stopped in front of the mansion, Janie once again opened the door of the limo for me and took my hand to help me from the car. She again smiled when she caught a glimpse of my pink panties peeking from under my dress. She smiled, saying "You are such a sweet sissy, tease you are," and gave me a little peck on the cheek. She held my arm as we walked to the door, I think she could tell that I was extremely nervous and she tried to reassure me. Walking through the front door and into the foyer I was startled to hear two pairs of high heels clicking on the marble floor, Janie's and MINE! She left me standing in the foyer to summon Ms. Williams. While standing there I though of my options. I could turn and run out the door and escape. But reality took over, where could I co dressed like I was? Police? No, I think not. I would probably get arrested or worse. I could not do much, I didn't even have my clothes or my wallet, and even if I did, I was broke anyhow. I was wrenched from my thoughts by the sound of a hearty woman's voice. It was Rebecca! How could I face her? "My, my, my, how the mighty have fallen! Don't you look like the sexiest sissy girl in the world? Janie has done wonders with you, even better than I had expected. How do you feel now, 'Mr. Smith'?" Ms. Williams had seen me, it was all out now. The way she looked at me made me feel like a mouse about to be devoured by a cat. I wanted to melt into liquid and run through some imagined crack in the floors of the opulent apartment. Rebecca just strode gracefully toward me, and held my shoulders to kiss me firmly on the lips, her tongue sliding into my mouth like she had always greeted me this way. I parted my lips and took her tongue into my mouth as though it was the most natural thing in the world. My knees became rubber, and before I knew it I was leaning full against her strong, statuesque body, my hands sliding up her back. Her breasts were pushing into my breasts and she reached behind me, she grabbed my ass and pulled me into her crotch. I was sure that I would rip the cache panty with my excitement, or worse yet, fill my panties with my cream. Finally, released from our passionate kiss, I got a chance to see her. I knew she was beautiful, yet I had never seen her dressed like she was now: pure feminine power. She wore a royal blue see-through, long gown and underneath, the prettiest lingerie I had ever seen. She had a royal blue, satin shelf bra, which held her hard nipples up invitingly. The matching panties and garter belt were barely visible, and her dark hose ran down her long legs like a river to pools which were perfectly matched 3" high heels. Gazing at her panties I could see the outline of her pussy, and it appeared to me that there was a damp spot at the "v" of her legs. She was absolutely gorgeous and I wanted her. Then I remembered the way that I was dressed and how my cock was trapped between my legs! Why me? Rebecca dismissed Janie, each exchanging shrewd smiles. Then we were alone. "Well, 'Heather', I'm glad to see you have taken such an interest in our products," Rebecca mused. I was speechless. All I could think about was how I was a man and that I was now standing before the CEO of a major corporation in a dress! Oh, how would I ever live it down? "I can explain..." I started. But Rebecca dismissed the notion with a wave of her hand. "No, let me explain," she declared with a fiery tone I hadn't expected. "You were hand picked, Heath. Chosen carefully, by me, if you will. You are one of the brightest, and I must say looking at you now, prettiest male sissies I have ever set eyes on. But where are my manners? Please join me for dinner." She looked so beautiful and yet somehow Rebecca was stronger than anyone I had ever yet known. Captivated by the starkness of the contradictions that she alone embodied, I could only follow where she led. And she led me to a dining room that I can only describe as vast. There, she pulled out my chair for me and seated me like I was the lady. But Rebecca was certainly the lady here. Soon, there appeared a lone servant girl with the first course of our meal. As the poor girl hovered about us, Rebecca started to tease her as Janie had been teasing me. "My," Rebecca remarked, "your little titties are growing so nicely!" The servant girl blushed deeply but continued serving us. "Now where was I?" Rebecca reflected. "Oh, yes. We at Women's World believe that male dominance of our planet was, at a time, a necessity. However, it's clear that since we no longer have any saber tooth tigers running around, there is no longer any need for male protection. With the end of that need, meaning the arrival of civilization, came the advent of the male's compulsion to invent ways to make themselves remain important. More quiche dear?" I found myself hanging on her every word. She was making sense. Lord knows everything I had learned in my MBA program made little sense to me. She went on... "We at Women's World, arrived at the conclusion some time ago that it is merely a process of evolution, that males eventually become subservient to females. We're simply speeding up the process. It's inevitable, dear, don't you agree?" I wanted to run! I started looking around and wondering which window I would crash through and where I would run after that. Then she reached over and put her fingers at the nape of my neck and started playing with my hair there. "Come now, my little sissy. I've had reports on you all day long," Rebecca whispered letting the nails of her other hand ride easily under my dress. She slid one hand up my stockinged leg, the other hypnotizing me at the back of my neck, and soon I found myself saying, "Yes, ma'am." "You love being treated this way, don't you, Heather?" "Ooooh, yes, ma'am." Rebecca just grinned and cooed, "Then it's time we put you in your place, don't you think?" "Ooooh, yes, ma'am. Rebecca took me by the hand and led me to her "master suite" and shut the doors. I was enchanted by this awesome beauty, and let her take my pretty dress off with no hesitation. She looked down at the cache panty and shook her head. "Darn, we have to get rid of that. I have something quite different in mind for you, Heather." I stood submissively as she got on her knees and pulled the tormenting panty down my legs and flung them into a corner. My cock pointed straight out, sticking practically in her face. She detached my stockings from the garter straps and slowly filtered each one down my now hairless legs. I lifted my feet, one by one, and she had my stockings in one hand while the other was stroking just behind my knees. I could feel her breath on my cock as she said, "I wish I had a real man! I would love to suck a powerful man's dick!" She pushed my hands behind my back and tied them together with one of my stockings. My hard cock was practically slapping the cheek of her face. "But you are not a real man, Heather. You're just a feminine, little sissy girl!" While she said it, she was wrapping one end of the other stocking around the base of my cock and balls, tying it tightly. Then she spread the remaining silky material of the stocking out over my stiff cock, enveloping it, and pulled it down abruptly between my legs, up the crack of my ass, and secured it to the space between my tied wrists. "There," she said in triumph, "now every time you move your hands, your sissy clit will be stroked by pretty, feminine stockings. That should keep you!" "How does is feel to be put in your place by a woman!" I moved my hands about and sure enough, the friction of the stocking torture device on my cock and against my ass was doing its work. Soon, very soon, I fell to my knees, begging for release. "Please, ma'am, I'll do whatever you say." "Yes, you will, Heather. Oh yes, you will..." As Rebecca rose from her kneeling position I thought she would never stop rising upward. She was like an angel, floating ever upward, borne on wings of sheer pleasure. She looked down into my hungry eyes, and romance threatened to wash the moment away, eclipsing my lust- our lust, all lust. And I felt myself falling deeply in love with her. She took me into her arms, her fiery eyes devouring my body. I was a conquest, yet my willing passion reached a foreboding place. The look in her eyes, the way she held me. How I thought that it should be I who did these things. Still, in that moment, I gave my love over to her and surrendered totally. "I love you..." I breathed from somewhere deep within me. It was true, I loved her from that moment, wishing that all the moments that make up time could somehow be this moment. I knew that I wanted to be hers, to belong to her. I knew that I did belong to her now, and that somehow, she belonged to me. All other realities simply disappeared and all other things ceased to exist. I felt myself swoon. I was were I belonged and would stay forever, a sissy owned by a beautiful, dominant woman. Suddenly I felt Rebecca's lips on my own lips, our lipstick mingling together. She pressed her mouth hard against mine and let her tongue force it's way deep into my mouth. She grabbed the back of my head and pressed me deeper into her lips, her other hand found its way to my ass and she pulled me into her crotch. I truly knew at that moment what it must feel like for a woman to be ravaged by her lover. The movements also caused me to move my hands and in the process stimulate my already aching cock trapped in the silk stocking. I suddenly feared that I would cum too soon and loose this moment forever. Rebecca backed away from me and looked lovingly at me. "Do you want to be my sissy girl Heather?" I could barely mumble the word "Yes". "If this is so, you will always be the feminine sissy that I require. You will always address me as Ms. Rebecca, unless the situation does not warrant it, which will be very seldom. You will always do what I ask without reservation or hesitation. Such actions will be dealt with by prompt discipline. Do you agree to these terms Heather?" I could only look into her eyes and nod, my voice failing me just as my cock was failing my masculinity. "A nod is not sufficient Heather," she spoke in a firm tone. "Yes Ms. Rebecca, I agree to your terms, I want, no, need to be your feminine sissy forever." I could not believe what my mouth was saying, it was betraying me completely. "Very well then Heather, as you wish. On your knees before me!" she commanded. I merely sank to my knees in front of her, my cock bobbing in the silk cage she had placed it in. She turned and went to her vanity, her back to me for a short time. I saw her remove her transparent gown and let it fall. I stared at the beautiful sight of her lean shoulders and tight back leading to her tight sexy ass and long lean legs. She was apparently putting something on. I didn't have to wait for long to see what she was doing. She turned and walked to me and there it was. A long lifelike rubber dildo stretching from her loins! While the rubber cock looked out of place on her feminine body, it also looked as if it belonged on such a beautiful, powerful woman, my owner. Ms. Rebecca walked slowly to me, her lifelike dildo swaying back and forth in front of her, much like I remembered my own doing when it was hard and I was walking towards my latest conquest. She stood before me, looking down at my feminine figure, my own cock jutting from my loins. She grabbed her cock and began to stroke it and looked at me. "If you are to be my sissy girl, one of the duties you will have is to service my hard cock on demand. Since you are no longer a man, you must begin to experience true femininity at my hands." She took the cock and rubbed it on my cheek, then to my lips. "Kiss my cock Heather, do it now!" I tentatively kissed the tip of the hard cock in front of me. She put her hand on my head and began to push the cock towards my face. "Suck my cock, sissy girl." I know not why, but my lips parted and I began to slowly engulf the hard, lifelike dildo in front of me. Suddenly, I felt that this was the only place for me to be and the only thing I should be doing. My masculine pride failed me completely as I took even more of Ms. Rebecca's hard cock into my mouth, and my own cock was rock hard and leaking into the stocking tied around it. "That's right, sissy Heather, suck your Mistress' hard cock. You are getting me so excited, sissy. You like to suck my cock, don't you sissy girl?" All I could do is nod my agreement and keep sucking. She pushed the dildo deep into my mouth till I felt the pseudo balls hitting my chin. Then she began to push this mammoth cock in and out of my mouth picking up her speed as she went. Suddenly, with her cock buried deeply into my throat, she stopped and looked at me. "You are my sissy girl, aren't you Heather?" I nodded in response, once again. "You will make a very good girl for me I am sure. But to show your obedience to me and to fulfill your femininity, I want you to get on your feet and lean over the edge of the bed, when I remove my cock from your pretty mouth. Do you understand?" Once again, I nodded my agreement as she began to pull the hard cock from my mouth. Once it was out, I reached over and kissed the tip before getting up with her assistance. Gaining my feet, she helped me to lean over the edge of the bed on top of a big pillow that had no doubt been strategically placed there for my benefit. Bent over like I was, the stocking that bound my hands to my cock tightened cruelly. I could feel the stocking slide deep into the crack of my ass and pull mercilessly at my engorged cock. Ms. Rebecca just stood back, admiring the view for a moment. Moving behind me she rested the dildo on my exposed ass. Stroking the cheek of my ass she spoke seductively, "As a sissy girl, I think you know what comes next. All girls cherish the moment they surrender their virginity to their stronger lover. This is that moment for you, my sweet sissy. I will take your virginity if you so request, but keep in mind that once I do, you belong to me completely. I will mold you into the perfect sissy girl of my desires. Your only desire henceforth, will be to please me totally. Would you like that, Heather?" "Yes!" I moaned into the bed. "I didn't hear you, Heather. If this is what you want, you must beg me to fuck your sissy pussy and make you mine." This was an extreme moment of truth, and I pondered my answer as best I could. To be taken in this way would be one thing, to surrender to it, even beg for it quite another. The considered words found their way to my lips. "Yes, Ms. Rebecca. I want to be your sissy forever. Please take my virginity, fuck my sissy pussy and make me yours." I moaned. I couldn't believe my ears, what was I saying? Then it struck me, I did want to belong to this powerful woman, and I did want to be hers completely. She reached down and untied the stocking, pulling it from the crack of my ass and causing me to moan loudly. She then stepped behind me and said, "I hope your mouth got my cock lubricated enough Heather, but remember, every girl suffers a little bit of pain to achieve her womanhood." This said, she began to push the monster cock into my tight, virgin asshole. I winced in pain as she pushed harder and harder, till suddenly the head popped into my ass. I screamed at the invasion and the pain, but she soothed me saying "go ahead, girl, scream if you must, no one will hear you but me, and the possible exception of Janie and the maid. However I would wager that Janie has the maid in a similar situation right now anyway, and I doubt they would care what was going on here. So scream if you must, sissy, but this is imperative to your becoming my sissy completely. You will come to enjoy my cock soon, even long for it." She pushed the invader slowly but ever deeper into my ass, and soon, much to my amazement, I began to enjoy it. The pain subsided and pleasure began to take over. Could this be true? Me, Mr. Macho just yesterday, and now enjoying being fucked in the ass by a woman while wearing frilly lingerie and makeup like a girl? Could it actually be true that I was indeed a sissy, and that this strong, beautiful woman had seen it, known it, before I even did. I didn't know and really didn't care, I was enjoying the feeling and knew that I would be enjoying it again and again. I could feel an orgasm building in my stomach like I had never known before. Ms. Rebecca hastened the pace a little and soon I felt the hard cock sliding fully into my ass, the pseudo balls hitting my own on the inward stroke. I could also hear her moan as she picked up the pace. Could it be, that we would both cum at the same moment? Unexpected, she grabbed my hips tight and thrust with all her might deep into my ass and screamed a passionate scream. And I knew she was cumming! The thought that I could bring this beautiful woman to an orgasm by simply dressing in feminine clothes and letting her humiliate me in this way, took me over the edge. I began to cum like I had never cum before, almost from a place in my body I had never known existed. The silk stocking trapping my hard cock did nothing to contain my excitement, I could feel it spreading through the stocking and on the bedspread beneath me. I could also feel Ms. Rebecca spasming in her orgasm. Trying to push even more of her cock into me, even though there was no more to push. She fell over me and held me as both hers and my orgasms subsided. I reveled in the feel her hot breath on the back of my neck and her small kisses nibbling on my neck. It was over, and I could feel her beginning to pull her cock from deep within me. Some part of me never wanted her to remove her cock from me. Sensing this she hugged me and laughed, "Not to worry my precious sissy girl, there is more of that to come." Then I felt the cock pop from my ass to be replaced by only emptiness. She pulled me to my feet and untied the stocking from my wrists and removed the one from my now shriveling cock. Throwing them aside, she stood me up and led me toward her bathroom. "Undress me, Heather." was all she said. With trembling fingers I reached behind her and unhooked her bra marveling at how her breasts stayed taut and firm without the bra. Kneeling before her, I removed her heels and slid her stockings down her long lean legs. Laying them aside, I looked up right into those blue panties, only now I could easily see the outlines of her pussy as the whole front of her panties were soaked from her orgasm. I smiled to myself, knowing that I had done this to her. Placing my fingers in the waistband, I began to lower them. Slowly her wet pussy came into view, and I fought with everything the instinct to just bury my face in that pleasure spot. After taking off her panties I brought them to my face and inhaled the fragrance and then ran my tongue over them and tasted her essence. I could have died in peace right there with her panties in my hands and my tongue licking her essence. She stopped my revelry and brought me to my feet. Removing the rest of my clothing, she led me to the shower and pulled me into it with her. The warm water was wonderful and she proceeded to wash my body completely, not missing a spot. She handed me the sponge and I began to wash her body lovingly. Mine was a more thorough wash as I savored every inch of this goddess's body, her perfect breasts, her stomach, her legs and feet, then her awesome ass and then her perfect pussy. We showered in complete silence and she didn't say a word, just spread her legs when I kneeled and began to wash her pussy with my tongue. She pulled my head into her hot pussy while I licked her, and I thought I may suffocate as she ground her sex into my face- then, she came again! Our shower over, I dried her off and powdered her, and she left me to do the same for myself. Smiling over her shoulder all she said was "Plenty of powder sissy, a girls best friend." When I emerged from the bathroom she was laying in bed in the nude waiting for me. Beside her, was a pink satin baby doll nightie with matching panties, all covered in rows of delicate white lace. I did not need to ask because she pointed to the sexy clothes and said, "Your night clothes Heather. I hope you don't mind, but I prefer to sleep in the buff, but insist on my girls being dressed appropriately for bed." I was helplessly caught and I knew it as I let the nightie drop over my head and my now hairless torso and hips. Then came the matching panties which, with monotonous predictability, began to confer new arousal. "Horny again are we sissy girl? My, you're a regular little sex kitten aren't, you girl?" she said with a charming laugh. I crawled into bed next to her and she wrapped her arms around me and pulled me close. She reached up and clicked off the light, kissed me deeply again, then said, "Good night, my sweet little sissy Heather There is much for you to learn, but if you pay attention and strive for perfection, you will have a wonderful life and I know I will. You will be forever mine, sissy, and I am sure the pleasures we will share are too numerous to count." She fell asleep with me in her arms, tweaking my hard nipples underneath the ultra feminine nightie. Sleep came hard for me that night, as I had no idea of what I had gotten myself into or what would become of me. Nor did I understand why I enjoyed it so. I realized that if I had chosen to, I could have slipped out of the house and made my escape, but there was something deep within me that forbade such a course. What would life bring me now? Finally I fell asleep, dreaming of such funny things as frilly satin and silk and all things feminine.