It all started with an ad in a local advertiser newspaper, the personals. It was cryptic and the point of contact was a law office. Getting involved with a lawyer would be enough to keep most people away. But, I don't think like most people. I'm not smarter, just different. That's usually bad, but on rare occasions, it's been very good for me.

It has often been said that curiosity killed the cat. But, curiosity has accounted for almost all progress in the history of humanity, even the accidental discoveries. I'm inquisitive. Boredom has never plagued me. So, I didn't do it out of boredom, but out of curiosity.

"Man wanted for domestic duties. Must dress for success. Contact..." What would you make of that? Was this a legitimate add for a sissy maid job? My inquisitive nature revealed itself when I was four years old and I wanted to wear the cute dress my little friend wore to church one Sunday. I didn't see why she could wear something pretty while I had to wear the same boring suit every Sunday. I was simply told that boys don't wear dresses and that was that. But my interest in girl's clothes had been perked. I would eventually try on all sorts of pretty clothing as I grew up thanks to my understanding sister. I loved the varied sensations the different types of clothing offered, the pretty pastel colors and the way they made me feel. But all that had a down side that made me glad I was a boy. There was way too much choice.

All those styles, textures and colors offered a dizzying array of choices that could consume one's full attention. How did girls decide what to wear? Then that dictated what to wear under and over it and then there's the hair, makeup, shoes, and God knows what else. Being a girl could be a lot of work and very expensive! I was glad to have the limited choices I had as a boy on a regular basis, but in spite of that realization, I always envied the freedom girls had in that one facet of life. It would be nice to have those options occasionally, just for the fun of it when it wouldn't take away from other matters. Now was the perfect time to indulge my curiosity while I was still young enough to look good in a dress.

I was curious and young, but not stupid. I had made my first million before I was 22 and my second by the time I was 23. At 25 I had sold my company for a wad of money that now resided in brokerage accounts and real estate. Brokerage accounts are only insured up to ten million dollars, so you must have several at different firms to protect your investments adequately.

Long ago I came to the realization that I was an introvert. I just don't like people very much, but I try to force myself to meet and deal with others as a way to overcome this mild phobia. I wanted to get married some day, but I wouldn't settle for just any girl because I'm a romantic. I'm also analytical, so I knew what characteristics make a marriage work and what can kill a one. I would rather have stayed single forever than have a bad marriage.

When dating, I was careful not to reveal too much financial information which could distract from my many character flaws. While money is said to be an aphrodisiac, that's a short term fix. I wanted a girl to love me for who I was, warts and all, because that's the only thing that will last. In addition to money, I had something else of immense value to me - anonymity. I was never the face of my company, so I was never famous in the financial press like my partner. Thus I was anonymous except with brokers or my local personal banker who guarded my privacy as jealously as I did. That's the way I wanted it to be at that time in my life.

I had come to the conclusion that the greatest luxury is not money, it's time. Money might be second because so many people sell their limited amount of time in exchange for it, but with both, I was able to retire and explore the world as I pleased. I had freedom and good health. I had the time to read books, the most efficient method to satisfy curiosity. I had come to regard myself as an observer of the human condition, quite apart from society. I could identify with hermits living in caves, which ironically made most of my money not worth having, with one exception. Money is power, and power gives you confidence.

At the time of the ad, I would say I was living in a mobile home. Yes, a 60 foot yacht is a mobile home, but I rented a one bedroom apartment where I could crash or entertain and could come or go dressed as I liked. My ex-girlfriend had made me a beautiful Ralph Laruen skirt suit as a gift. It was an extravagant gift. It was beautiful and fit me to perfection. It was one of the sweetest things anyone has ever done for me and I missed her. After she dumped me, the loan on her new car was mysteriously paid off.

That suit is what I wore to the job interview at the law office. It was blue gabardine with maroon ribbon piping along the bottom of the below the knee skirt with a matching waist length form fitting jacket, a frilly high collar white blouse and maroon sissy bow tie were part of the pattern too. Knee high boots with a two inch heel completed the outfit. I even had my longish hair styled for the Interview and was made up to perfection. It would either fill the bill of "dress for success" or quickly get me thrown out of the law office. Nothing ventured, nothing gained.

I showed up for the interview, filled out a form, showed ID and offered references. It's not as though I was applying to be Secretary of State, but they wanted to make sure I was sincere and trustworthy. As I understand it, only five people applied and I was the only one "dressed for success" and the only one offered a second interview after signing a non disclosure form.

My second interview that day was by a young well dressed woman named Alice who took me to lunch. While still in the office, I had to remove my boots, lift my skirt and slip and stand on my toes because she wanted to see my legs. I was glad I had shaved them and put on new hose that day. I think lunch was to see if I was a barbarian who would eat with my hands or if I knew what a salad fork was. She was happy to buy me drinks, but I know not to drink in an interview. I had been on that side of too many interviews in my former life.

She was the housekeeper and would be my boss if I got the job. Her staff ranged from two to six depending on whether Mistress was in residence. She was smart, pretty and clearly had a well rounded education. She liked my choice of attire and my attention to detail and told me the job opening was for a sissy maid, asking if I knew what that was. I said yes but told her that I'm not a sissy, just a cross dresser. She viewed that as a distinction without a difference, and I let it drop. She was pleased to find that I was well spoken and relatively intelligent and she asked if I had any training as a sissy maid and I told her no. Then she asked why I wanted the job and I told her the truth, that it was out of curiosity and that I could not guarantee that I would be successful. It was an area that was new to me, but I would give it my best effort and if either party were dissatisfied, we could part with no hard feelings. The conversation drifted to ethics and morality to house work, perhaps testing my knowledge. Some of the questions were a bit personal and I left no doubt that there are limits to my tolerance and I believe people should treat each other with respect. I said I would not tolerate being humiliated, at least that's what I thought at the time I said it. I was interested in the job only if it was legitimate and that seemed not only acceptable to her, but to put her more at ease.

She showed me a picture of the uniforms which were very pretty and said I would have to buy them with money taken out of my paycheck, but it would all be reimbursed after six months of employment. I would have free room and board, insurance and two weeks of vacation after a year. The wage was not much, but enough not to be insulting. She did say rather apologetically that there are some times due to the nature of the job and the uniform requirements, especially when I first start, that she would have to inspect my uniform in a way that might be regarded as intrusive. She said that we are both adults and I shouldn't take the job if that would be a problem. It was a delicate matter and she tried to be discrete. She said that there are times when we would be the only two people living in the house and the servants' quarters are in close proximity. She added that she does not know me at this time and she said would not feel safe with a male stranger moving into the house with her without some sort of check on his abilities to initiate a sexual encounter. I could see she was embarrassed at this point, but I did not interrupt. She said until we got to know each other better, that she wanted me to wear a device for her protection. I laughed, thinking it was a joke, but she just sat there with an exacerbated look on her face as though I was being intentionally obtuse.

Then, realizing that she was serious, I was dumb founded. I had heard of chastity belts for women in the middle ages, but never something like that for a man. I told her that I was not a rapist and her suggestion was insulting. But, she said that she doesn't know what a rapist looks like and said "trust, but verify", a comment that is irrefutable in its logic. I could see her point, but asked, "Isn't that why I just gave you references? Also, isn't that why locks are put on doors?" I had mere moments ago said I would not tolerate being humiliated.

She said she would not take me into her mistress's home without first stopping but a local nurse practitioner for a fitting and purchase of this device and that neither of us would have the key to it. The key would be turned over to her mistress for safe keeping and eventually given to me. After the fitting, she planned for us to stop by the uniform shop. Then, and only then, would I see my new place of employment.

I agreed to go with her to at least see this device, but I told her it was unlikely that I would take the job because of this. She seemed disappointed but was unwilling to make a concession on that point. Alice stayed in a waiting room while I went in to see the woman who fitted and sold these things. The whole process was humiliating although she tied to put me at ease. There was no need for an inspection as the woman's assurance that I was "all locked up" was good enough for Alice, but I couldn't look her in the eye out of embarrassment. Obviously, I agreed to wear it. But before doing so, I told her that there was no way in hell I would pay for the privilege of being insulted this way. Alice agreed I would not pay for it and the nurse agreed that she could and would remove it on my demand should I leave the job. I was not about to go to a locksmith with this problem and removing it myself looked dangerous.

There's no need to dwell on the device except to say I was told I would have to wear it at least a month. Alice admitted that in addition to her stated concern, it was a method to exert power over me because a sissy maid must be submissive to feminine authority and my willingness to wear this was an act of good faith on my part. What the hell is "feminine authority"? I'm not by my nature submissive and that's not why I was there. I just liked the pretty outfits, thought it would be an interesting experience and was willing to do a good job. I would submit to my employer's authority regardless of gender by virtue of a verbal contract. She offered me money and other considerations in exchange for my time and obedience. That's a contract, not "feminine authority" but, I was there to learn, so I'd keep an open mind.

The next stop was the uniform shop where Alice took great care insuring that I was properly corseted and uniformed. She had obviously done this before and knew the ladies at the shop. I liked the uniform and loved the corset. Together they made me look and feel pretty. They did fitting and alterations right there on the spot. Then, perhaps testing my sensitivity to public exposure in the skimpy outfit, she took me to a shoe store. People did stare and smiled and I smiled back. It was exhilarating to know that people thought I was worth looking at. I doubt if they knew I was a guy because I'm short and not broad shouldered and a choker collar hid my Adam's apple. Nobody in town knew me anyhow.

After getting some three and five inch heels, we headed back to the law office to pick up my car and I in my new uniform followed her home. I had been told to bring a suitcase of needed personal items. I did warn Alice that the five inch heels were a waste of money, because I would never be able to walk in them. Two inch heels were more in my comfort zone and flats were more practical for housework. But, I soon learned that my job was not about housework. If it was just about housework, the cute uniform wouldn't be needed. Alice would teach me that it's about showmanship.

Now, perhaps I should point out that this might not be a normal sissy maid experience because it has nothing to do with discipline or punishing bad behavior or BDSM. Well, at least not from my prospective. I had a car and an apartment to return to so I could leave at any time. This is more about states of mind and how the mistress's proclivities seemed to align with my own even though they were quite different and had completely different origins.

Alice showed me to my room and insisted that I change into my new three inch heels. As I put them on I looked at the five inch heels in the other box with trepidation. They looked deadly. Then she showed me around the house telling me what needed to be done in each room and how often. She pointed out that a French maid working in a room, regardless of whether it's a boy or a girl is by the nature of the costume, the center of attention. It is the opposite of a traditional maid's uniform that is intended to blend in to the surroundings. For that reason a French maid is not about doing housework, it's about doing housework in style and entertaining everyone with the good fortune to feast their eyes on your pretty legs, shapely body and lovely panty clad butt peeking out from under your short full petticoat.

She said, "There's nothing subtle about a sissy maid. It's a statement like driving an exotic car or flashing a decadent piece of jewelry. It says "look what I have." The mistress is saying "look what I have" and so is the girl or boy in the outfit." At that point, I asked her why they wanted a boy in this pretty uniform instead of a cute girl. She simply said it was her mistress's preference and I might want to ask her that question sometime. She said that she too would wear an identical uniform when mistress had guests who would prefer looking at a girl or be put off by the knowledge that they were unknowingly lusting after a boy. I surmised that meant I was a treat for Mistress's eyes which I took that as a compliment.

The house was magnificent. I immediately recognized it as a Frank Lloyd Wright design, probably pre World War 1. It was remarkably intact with many of the original furnishings in excellent condition. These were museum pieces. This house was no knock off. Wright obviously had the commission on this place when it was built, otherwise the furniture and windows would not have been so characteristically his. I had read several books on his work and even toured a few of his houses, but I never imagined I'd actually have the privilege to live in one.

Wright was an autocrat who inflicted his style on his clients seemingly without regard for their comfort. At "Falling Waters" he used the ripple marks in the naturally flat lying rocks as the dining room floor necessitating his invention of three legged dining room chairs for stability on the rough surface. He obviously didn't give a damn about the women or sissy maids in high heels that would have to walk on that floor.

This house has its own idiosyncrasies. It has what we now call a great room, except this one is huge and two stories high. In the great room are two large rectangular sunken spaces, a living room and dining area, sunken about three feet below the rest of the room leaving ten foot wide walkways around and separating them from each other. The walkway has built in furniture like sofas, settees, chairs, book shelves and work tables denoting areas for different uses. Glass fronted china closets line one wall adjacent to the dining area. There is a giant fireplace centered along one lining up with the separating walkway. The family bed rooms and guest rooms are at the living room end of the house in two stories while the garage, utility areas kitchen and servants' quarters are at the dining room end in two stories. A narrow second floor gallery encircles the room connecting the two wings, with stained glass windows along both second floor longitudinal walls. This job was already turning into an adventure beyond my expectation. I think Alice was impressed by my knowledge of architecture and was proud of her new hire.

There was much to learn, including things specific to this house regarding historic preservation. In a similar vein, I was shown a large sink made of wood and soft rubber with soft cypress wood drip pans in the kitchen that had been specifically constructed for cleaning Mistress's prized china. It was her great grandmother's china and I washed the everyday dishes as practice for her china that was treated as though they were rare art treasures. For some reason, the kitchen help would not be trusted with that task which was my responsibility.

I would not meet our boss for another two weeks. That's when the workload that I consider heavy, greatly increased. I worked forty hours in a five day work week with two days off, but since I was in uniform all day, I was basically on call all day. Working weekends meant overtime pay. If I had the weekend off I'd go to my apartment to change into my male clothes, cover my styled hair in a hat and check on my boat at the marina where I was spending almost no time. My boat was neglected and I'd spend weekends cleaning it.

The mistress, Anne, arrived with an entourage. I'm bemused by this kind of display of wealth, but more curious about the kind of personality that wants to project it. Is it some deep seated insecurity? I was told that I would be introduced in due course, but until then, just stay out of the way. That's hard to do in a French maid uniform.

Alice said she regretted not having more time to train me suggesting that I was being thrown to the wolves too soon. She warned me "Keep your panties on because that device won't protect you from what some of them will want to do to you." When I told her I was straight, she said that wouldn't matter to these guys, so just watch out, adding "at least you can't get pregnant!"

When I expressed shock she said "So, you think you can wag your pretty little ass around in a French Maid outfit without any potential consequences? You cross dressers want the benefits of femininity without any of the downsides. Well, I hope you are smart enough to pull it off, because there are pitfalls to wearing these cute little outfits that we girls must endure our entire lives, but you want the privilege to dress like us without paying the dues. Welcome to my world sweetie where you know from the time you're twelve years old that the boys want to fuck you all the time." Clearly, I'd get no sympathy from her. I confess her comment scared me.

Before she was swept up in the approaching storm of activity, I asked Alice how many sissy maids her mistress has had and she said at least four, but they seldom lasted long. She was not a fan of the idea of sissy maids saying they weren't worth the bother. I wondered if they had quit after being raped, but said nothing. This was the time when AIDS was a full blown epidemic. That took the wind out of my sails as far as the sissy maid thing goes.

I watched the onslaught of strange faces filling this grand old house and wondered who all these people were? Alice's staff would now swell from two, me and the gardener, to six with addition of a cook and kitchen helper, a driver/ handy man and an upstairs maid. She wouldn't have time for me anymore. I was on my own.

I went about my assigned cleaning duties with the knowledge that I was being constantly watched. I could see my reflection in the glass of the china closet doors as I would mince past and I admired the shape the corset and silicon breast forms gave me. The garters attached from the bottom of the corset to my nylon stockings would stretch as I bent over and served as a reminder not to show too much of the upper stocking and panties. I would instead stoop to pick things up which also stretched the garters, but didn't put on as much of a show. That was the kind of sensation that attracted me to cross dressing as a youngster and I still reveled in it.

The three inch heels were rough on me and made everything more difficult and strenuous. This house, like all of Wright's creations was designed to showcase his talent but showed little concern for peons like this sissy maid who had to inhabit it. Traversing the entire length of the galleries many times a day in heels was arduous, then add to that, the work to be done and loads to be carries and it was exhausting.

Keeping in mind Alice's comments about showmanship, when guests were present, I always made sure to walk along the outer edge of the gallery to give those on the first floor a good view up my skirt, not that there was any vacant space in there to see anything, but they always looked. I guess imaginations filled in what the eye didn't see. The shinny panties and frilly petticoats resembled a white fully pedaled flower in bloom. I found the rubbernecking amusing but I would pretend not to notice. Is this what being a pretty girl is like? If so, it must be wonderful while it lasts, but terrible when it ends. This went on for several days with an occasional slap on the butt, but it was nothing serious and I could rebuff advances in a civil, but flirtations manner. Most of the guests turned out to be nice people. They were children of old money with too much free time and too little imagination to take advantage of such a precious luxury.

About three days after her arrival, I was finally introduced to Mistress. There must have been a lull in the almost constant party and she took that opportunity to meet me. She told me I was pretty and I said "Thank you". Then she admonished me for my failure to curtsy when presented. I apologized and told her that Alice had instructed me to do so, but I had forgotten. I then curtsied as Alice had taught me. When she asked me why I was a sissy maid, I told her, but when she asked why I couldn't get a better paying job than that, I told her she should not assume that everything is about money but that was not her concern anyhow. I could see an expression of surprise, but not anger on her face. She was much younger than I expected and very pretty.

I did take the opportunity to ask why she wanted a boy in this job and she told me she loved the juxtaposition of the roles of women and men and was fascinated with the concept of feminine authority from the first time she read a book about a woman who ran a railroad. I immediately thought of what I regard as the most feminist book of the 1950's in which the heroine, Dagny Taggart, ran her families railroad while her useless brother as company president got credit.

The Russian woman, who wrote that dystopian science fiction masterpiece complete with energy shields and an endless nonpolluting energy source that could replace oil, should have been an environmental and feminist icon except for her one sin, she was anticommunist. I had observed that those movements, feminism especially were always subservient to leftist interests. Nothing makes a woman equal to a man like a loaded gun in her well trained disciplined hand, but rather than embrace that ultimate empowerment of a woman, the movement let women continue to be victimized to placate political allies - how femininely submissive of them.

I told her "I read a great book like that, starting with a woman getting on a train with her railroad employee's pass. It describer the sheen of her stocking, her high heels and her feminine elegance before having her wake up to find the train stopped. She goes to the front of the train to see why and onto the tracks finding the conductor, engineer and other men talking about a stop signal. She, knowing all of the company's routes and schedules down to the last detail, tells them it's an electrical problem, to ignore it and proceed, but the engineer says he lacks that authority and the others act like, "who the hell are you?" The conductor recognizing her as the company's chief of operations orders the engineer to do as the boss says. I loved the juxtaposition of that young woman directing these gruff men and keeping a hundred year old record of never arriving late intact, but that book was about personal responsibility and the dangers of economic central planning, not feminine authority."

Her face lit up. I got the impression her friends were too busy drinking to read any books at all and I had hit upon her favorite book, one that had actually formed some of the basis for her lifestyle - even if by mistake. She invited me to sit down with her and we spent the rest of the evening talking about the book and a hundred other things. I asked her about the house and its history. And there were things I could tell her about it that she didn't know. We talked all night.

She liked me and I liked her, but as I left she noticed my shoes and perhaps to remind me of my status as her sissy maid, she told me that Alice was to have me in five inch heels. I said Alice had me buy them but walking in three inch heels was about the best I could do. She said, "Five inch heel tomorrow. No excuses." And I said "Yes Mistress", curtsied and left.

The next day, after only four hours sleep, I was in five inch heels walking slowly and not very gracefully. I fell twice and ran my stockings once. One of the men grabbed my ass and said that I couldn't run away from him now. An elbow in the gut proved that I could. Some of the women found my suffering quite amusing, but I paid a high price for their entertainment. My legs and feet were in agony and after ten hours in them I couldn't sleep that night due to the pain. The two additional inches made no since and I implored Alice convince Mistress to relent, but Anne wouldn't. She wanted to show off her new sissymaid to all her friends and for some reason the shoes were important to her.

The final day of the party didn't go well. Anne and her friends had an elegant final dinner in the dining area with Alice and me in identical uniforms serving wine and food. I was tired and sore, and the occasional grab ass didn't help but I carried on and even smiled. Then they all retired to the living room for tea and coffee. Alice carried a large silver tray with the good china cups and saucers and I followed with an equally large tray with the prized porcelain tea service. Going down the steps, my five inch heel hooked on one of the steps and I fell forward, tray in hand but the antique tea and coffee service went flying. From the first sensation of the hooked heel, I knew what was going to happen and was powerless to stop it. It's as though it all happened in slow motion. It was humpty Dumpty time for Mistress's prized family heirlooms.

I instinctively dropped the tray and desperately batted the tea pot, now at eye level, with my finger tips like a volleyball toward Alice who was returning with an empty tray. I could see her eyes get big and her mouth open as she saw the catastrophe unfold and by some miracle, although I didn't see it, she had the presence of mind to drop her tray and reach up to catch the teapot, top still attached. In the meantime I had randomly batted one of the smaller pieces with my other flailing hand high into the air and it was eventually caught by a quick thinking guest. I managed as I fell to lunge at the big coffee pot and grab it both hands before it struck the floor. I fell flat on my face and elbows just barely managing to save the big pot. The creamer broke into tiny shards as it hit the floor. Cream, coffee, tea and sugar covered many guests but things could have been much worse. After the initial shock, screams and gasps, there was a moment of complete calm, and then everyone broke into cheers and clapped for the three heroes. The next day as the guests were leaving, I was back in three inch heels with a certain key in my position.

After that, Anne and I talked a lot. I remained her maid for about three more months and by then the experience had run its course. But after a haircut and in more conventional clothes I did keep seeing her. I also convinced her to re-read the book so she would see it wasn't about having men submitting to feminine authority after all, although all the best men in the book did fall head over heels in love with the heroine Dagny. It didn't take long for me to fall in love Anne either.

We were so different; me introverted, serious and philosophical and her extroverted, fun and spontaneous that we actually complimented each other. We had similar basic values and identical views on marriage. She wrestled with the idea of falling in love her former sissymaid, but finally professed her love for me. From then on she held real feminine authority over me. I was and occasionally am the last sissy maid she'll ever have. I had told her many times that I had a secret, and she would always laugh assuming that cross dresser was my big secret. To celebrate the fact that we both wanted to spend the rest of our lives together and to alleviate any potential concern on her part that her wealth played any part in my affection for her, I took her out for a weekend on my boat and told her told her my other secret. She laughed. The fact that I had more money than God, didn't seem to bother her and we lived happily ever after.

The End

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