A Sissymaid Washout
by
Missy

Dear Auntie Helga,

The letter from Sissymaid Tiffany and Linda touched a nerve with me so I would like to recount a similar experience. Fact is, some of us just don't make the grade.

Let me start by saying my wife is the smartest person I know. We love, respect and know each other too well to lie to one another and lying to her, even if I were so inclined, would be futile. I have always been up front with her about cross-dressing. Even before we started dating she was one of only two people I told. She has accepted that part of me with mixed levels of enthusiasm over time recognizing that any negative is more than offset by redeeming qualities.

I would like to say that I, like Tiffany, broached the topic of becoming a sissy maid while my wife was teaching me some aspect of feminine domesticity normally deemed too complex for a primitive masculine brain to comprehend, but that would be a fabrication. The fact is, I'm a better house keeper than my wife. We have always had a good division of labor in household chores, but there are some things that just always fell through the cracks, like making up the bed.

Unlike Tiffany, cooking was one duty I would not be asked to take on. While I wouldn't need training in housework, she has made it abundantly clear that she would never eat my cooking. Isn't it amazing how one little cooking disaster early in a relationship can taint a person's perspective for life! She is a great cook, and I could never approach her skill level in that regard, but that's a matter of talent, not training.

Our view of housework resembled the old joke: "I hate housework. You do all that dusting and mopping and six months later you have to do it all over again." She did all the cooking and dishwashing and I did all the laundry, dusting and floors. The countless other household tasks were divided spontaneously based on who was in the right place at the right time or differences in skills or strength. I should do more of the dishes but that, as she knows, is the chore I hate most, so she does them. For some reason our dish washer sits unused. I did the vacuuming and mopping when it was obviously needed, but never on a regular schedule.

The topic was broached when she commented on dust bunnies moving across the floor and I said the maid should clean them up. She said that we don't have a maid and I replied that I could be the maid. The rest of the evening's conversation was typical, with her suggesting that I could clean the house wearing men's clothing just as well as I could when wearing women's clothing, but I countered that it wouldn't be as much fun for me.

The next day after a late night on the Internet, she asked if I really wanted to wear women's clothing while I cleaned the house. Like Tiffany, I answered something to the effect that I did if she thought it was appropriate. Unlike Tiffany, I was quickly shot down. She immediately replied that it was definitely not appropriate, so that should be the end of it based on the standard I had set - her judgment of what is appropriate. She smiled having effectively exposed the insincerity of my comment but added that it seems harmless enough. If that's what I wanted to do, she would indulge me within reason. She did however, somewhat tongue in cheek; point out that my desire to dress like a woman while doing what I obviously regarded as "women's work" reveals an archaic and somewhat sexist view of my opinion of a woman's place in society. True, but I didn't take the bait to change the subject.

I had used the term "sissymaid" the previous evening which I know caught her attention and had probably prompted her late night research. I had also mentioned your website, so I think her reply was an attempt to mitigate the situation. When I pressed her on the topic, she admitted that she had gone to your website and a few others. She added that having looked at some of the sissymaid websites; she thought most guys in French maid outfits look either pathetic or grotesque. "If you are going to do this as anything more than an occasional lark, and if I will have to look at you, I will insist that you do it right. I don't want you to look like a freak. I am not saying this to be mean, but we have always been honest with each other, so I'm simply expressing my opinion. I must tell you that I have read some things that I find alarming." She expressed concern about some of the ways people are exploited, sexually abused and humiliated by one who is supposed to love them. We both understood that was the way some people wanted to be treated, but I assured her I did not. With that out of the way, she had one final question for me, "Do you want to dress like a woman and do "woman's work" to experience what it is like to be a woman, or is this, an expression of your desire to BE a woman and live AS a woman?"

To her relief I said it was the former. She knows I am inquisitive and I told her that I have long been curious about what it feels like to actually wear lingerie, heels, and other women's clothing in the course of a full working day rather than simply trying it on for short periods of time. I added that any boy of my generation who did not try on his mother's or his sister's girdle, bra or nylon slip must have been so incredibly incurious as to be almost brain dead.

She replied that if we do this, she would certainly try to satisfy my curiosity within reasonable limits lamenting that I had never experienced menstrual cramps - "That would give you a different view of womanhood." She then pointed out that real women don't wear French maid outfits unless they are a cocktail waitress, a stripper or to get laid on Halloween. Adding that this is nothing but a fetish and remember the old adage "Be careful what you wish for".

"I have known of your French maid fetish for years. How many times have you watched the movie "Clue" just to look at the French maid mincing around? I told you when you brought it up years ago that if anyone in this household was going to wear a French maid outfit, it sure as hell won't be me! I just didn't think it would be you either. So, if you want a French maid outfit while doing housework, nobody would be the wiser. But, the sissymaid thing is a bad idea."

"Quite honestly, I don't think you can do it. I don't think you could stand living that way for weeks at a time. I can't see you in heels all day, which I warn you – I will require you to wear – all day! You enjoy dressing for a few hours at most, to relax, but that's it. The fact is, you are not a very good cross-dresser. You lack commitment! At some point it is too much work for no real return and that is not in your true nature. You are far too practical for this."

She pointed out that the time to wear a wig and put on and remove makeup everyday is that could be put to better use, and while admittedly, the French maid uniforms are pretty, the stockings, high heels, "underpinnings" and other accessories worn by sissy maids could be expensive, easily damaged, uncomfortable and would greatly reduce my productivity – if cleaning the house were the real objective, "Which it clearly is not! We certainly have the money and freedom to do it, and I will go along with your choice regardless."

At that point, the ball was in my court. With fantasy weighted against well thought out well presented cold hard facts and logic, fantasy of course won out. She reiterated that she that she always regarded my dressing simply as a peculiar hobby but, the 24/7 sissymaid thing was clearly a lifestyle commitment that dwarfs a hobby in scale. Also, it would require a significant amount of her time and effort, because the burden of leadership, normally shared by us falls entirely onto the wife in this situation as though management is somehow not work. She would get nothing out of this except a clean house, which I should have been cleaning anyhow. But, her greatest fear was that she would invest her effort into researching this, running down prices and sizes on the Internet and invest more than a little bit of our money just to see me drop the entire project when the going got tough or if it wasn't the fun lark I was expecting it to be, "because I assure you it won't be". "For that reason, if we do this we would have to agree to a specific time period so you can't wimp out after two days and a we must agree to set of rules in advance so my efforts and our money would have some sort of payoff, even if it was just as a learning experience for you." She had already said it was up to me, so she was simply laying the groundwork for one big "I Told You So!".

Still pressing the issue, she pointed out that although we have a large house; it is not large enough to justify a full time maid. "Besides, there are things that you must do outside as part of the regular maintenance of our property such as mowing the lawn. A French maid would look odd on a lawnmower or bent over weeding the garden. Who would do your work, outside while you are indulging your little fantasy? Those were all problems the boss would have to resolve."

In other words I really was dumping them off onto her. I was dragging her into territory about which she had repeatedly expressed discomfort. Yes, I was being selfish, she knew it, I knew it, and at this point we both knew it was going to happen. She was being asked to lose her husband for some period of time. One additional problem would be the social isolation this would necessitate. She couldn't be expected to go to a community event with a sissy maid in tow. Nor, was she going to date other men because she had married the man she wanted and both of us take our marriage vows seriously. Also, she asked, "Do you intend to show up at club meetings dressed in your little French maid dress? If so, aren't you imposing your problems, preferences and your fetish onto innocent people who have no obligations to shoulder your problems because they and their loved ones have problems of their own to deal with? Isn't that unethical? If not, this means disappearing from sight at least for the duration of the test." She reiterated her opinion that this was a really bad idea, but said "What we are faced with here is an obsession rather than a choice that can be resolved by rational judgment, so I am resigned to it."

She said the reason for this was obvious. "If you are required to dress this way as a job requirement that we both accepted, then you are absolved of any guilt that you might feel from violating a social taboo. While we both intellectually reject that ancient social norm, deep in your subconscious you still feel an irrational guilt about cross-dressing. If you are a submissive maid doing as told then guilt is shifted to the one who is making you do it. That's why all those stories have blackmail, hypnosis and other things forcing them to dress - to absolve your guilt!"

With a change of stance, an expression of determination covered her face and in a very assertive tone she blurted out, "OK, I'll be the bad guy! Put the guilt on me. But, remember I know how to fix your wagon. I know how you think. I know you better than you know yourself. You might just be putting the whip into the wrong hand Sweet Cheeks. Remember that!"

A chill went down my spine! Suddenly, I wanted as Tiffany termed it "a disclaimer" and just as her Mistress Linda, had calculated the cost of the clothing and accessories, my wife had already determined that as a contingency plan the night before. For us, however, there was no need to compare it to the cost a maid service. There would be no maid service. Having opened this can of worms, I was now on the hook to increase my share of the housework and put it on a regular schedule regardless of what I wore. Clearly this could blow up in my face, and it ran the risk of permanently damaging our relationship. She could lose a husband she wanted for a sissymaid she didn't want. This could be a "lose-lose" for both of us. But, we proceeded. She set a time limit for the test at two months, to begin in two weeks so she had time to prepare.

Confident I'd want to wimp out, but knowing I keep my word, she might just teach me a lesson. Having agreed on the timeline she pulled out a contract she had downloaded and modified the night before. She demanded that we both sign an agreement laying out all the rules so there would be no recriminations or acrimony from faulty memories or false assumptions by either of us. With my decision announced, and the agreement signed she pulled a tape measure from her sewing draw and began measuring me for what she termed "your new life".

It was a standard agreement seen on sissymaid websites, with her having almost total authority, but I didn't mind signing it because I knew she would never do anything unjust. I knew she would not harm or humiliate me so I signed the contract with complete faith. For those two months I had agreeing to obey and serve unconditionally. The contract gave her complete control over uniforms, clothing and other accessories commonly worn by sissy maids, effectively negating the entire clothing question. Under this agreement I would wear whatever she told me to wear – even men's clothes, but she assured me that she would at least ask for my opinion before selecting my sissymaid or other dresses. She left no doubt, however, that she possessed the ultimate authority in these and most other matters for those two months.

The big day started out as described so often on this website with a nice bath and body hair removal, and even a new bra and matching panties that she had gotten for me. As I sat on our bed she presented me with some silicone breast forms that she had determined were appropriate for my height and weight. She said that they were heavy duty enough to sleep in and sweetly assisted inserting them into the bra inquiring about their fit and comfort.

As soon as I said they were perfect, things changed. I was told in a commanding voice to stand up and she quickly ushered me out of the master bedroom wearing just my stuffed bra and panties, down the stairs, through the kitchen and into to the smaller of our two guest rooms just off of the kitchen. "These are the servant's quarters Missy - your quarters". "Welcome to your new life. You will only enter MY bedroom at my instruction. My husband's clothing and possessions have been locked away and they are not to be touched by the maid. Is that clear?" My change in status was now official and she had driven that point home brutally!

During the preceding two weeks, she had quietly placed my new wardrobe in the room. A black satin sissy maid dress, exactly as I had picked out, was hanging on a hook on the closet door and a frilly white petticoat lay on a chair beneath it. I was incredibly happy at the sight, but was told to lie down on the bed for some additional grooming before I could get dressed. Then, with a ballpoint pen she reached under the bra and carefully outlined the breast forms, putting small reference marks on the top and bottom center of each form and outline. With that, the bra was removed and she carefully brushed glue within the outlines and onto the backs of the forms placing each form carefully in place and instructing me to hold it firmly in place.

She said, "Well, you wanted to experience some of what it feels like to be a woman, so for the next two months you will wear a bra because you must, not because you just want to. I've gotten you a soft cup bra to sleep in to prevent undue stress on your skin and some more substantial bras for daytime use. Those babies are heavy and will tear up your skin if left unsupported, so take care of the girls. The glue is set, so go ahead and put your bra back on. I still have a bit more to do. I know because of the boobs you can't see what is going on "down here", so just spread your legs like a girl and I've got a big surprise for you."

From her sweet smile and composure, I thought, wow, she's even going to give me a blo... Oh crap! Having repeatedly expressed her disapproval of cages and other chastity devices seen on websites in the preceding two weeks, she had convinced that I would be spared that indignity. So, a chastity device of her own design caught me completely off guard sending me into a state of total confusion. Taking advantage of my obviously excitement she grabbed me and unrolled a tight finger cot that would let urine flow out through a small exit tube. Having placed it to her satisfaction, an icepack was quickly and strategically applied and achieved what she called "maximum shrinkage". I let out a loud gasp, but that did not deter her. With that accomplished the remnant of my manhood was placed into a small encasement and folded down between my testicles. I was "tucked", but with a major difference, everything was covered with a tight protective latex covering that was glued in front with a flat fur covered latex sheet resembling pubic hair and tightly stretched behind with two strips, one on each butt cheek leaving the approximate appearance of a vagina. I couldn't believe what she had done. It was effectively a glued on latex version of a woman's chastity belt. She had obviously given lots of thought to this considering it was dreamed up and fabricated secretly in a maximum of two weeks and it must have taken some time to assemble the materials. It all happened so fast and was done with such efficiency and skill that it was over before I could react. She said she'd try to satisfy my curiosity about living like a woman and she certainly was.

She made sure that I got up and moved around to insure there was no discomfort while the setting glue still afforded a chance for adjustment. Being no stranger to tucking, I felt no discomfort - just extreme embarrassment. We talked about hygiene and when I began to collect my wits I told her I would never have agreed to this. She smiled, looked me in the eye and said I had agreed to it in the agreement as an "accessory commonly worn by sissymaids" so "Shut up!"

I felt like an idiot. My new reality was quickly sinking in as her "be careful what you wish for" comment flashed back in my mind. Was this my plan or her plan? Had I been played? Being ensnared in her "accessory" combined with her rebuke, my sudden expulsion from our bedroom and being shuffled down the back steps to the "servant's quarters" drove home her "Welcome to your new life" comment. I felt truly humiliated and foolish in front of the one other person whose opinion mattered to me. It turned out she was willing to humiliate me, just not in public. She was certainly willing to do it in private if she felt I deserved it. And, I did.

Just when I thought it couldn't get any worse, it did - much worse. As she pressed the final piece of latex waiting for glue to set up, she leaned over and whispered into my ear, "Remember King Lear?" A since of fear and foreboding engulfed me. Was she just messing with my mind? Paying me back for my selfishness? I suddenly remembered the contract. While our entire discussion was her saying she did not want a sissymaid, and making sure that we had get it over with, there was an extension clause in the agreement - at her discretion. My assumption, no, my absolute certainty had been that she would want it stopped after two months and if anyone wanted it extended, it would be me, but now I have even lost control of that.

While I could pull out of the agreement unilaterally, by just breaking it, I gave her my word and it would be a violation that we would both remember for the rest of our lives. On the other hand, I could be on the hook to be her sissymaid for two months plus an additional year. After that, who knows what would happen. Good God! I'm an hour and a half into this and she already has me regretting it and thinking of bailing! Three weeks ago I was one half of a prosperous happy couple with a beautiful home, a loving wife and a bright future. Now my future was uncertain. While the contract was completely unenforceable in a court of law, it would be damning evidence in a divorce proceeding. I was truly at her mercy, a mercy I had trusted implicitly until moments ago.

Her day of big surprises continued with the unveiling of a beautiful white satin under bust corset. It was like Christmas and my fears subsided in all the excitement. I think she was enjoying my delight and perhaps her newfound power over me. I had put my bra and panties back on along with a matching camisole she gave me to go under the corset. I was deliriously happy! While I had told her what I would like, she had been completely tight lipped about what I would get, reminding me each time that it was completely up to her – not me.

I laced up the corset myself and it gave me a phenomenal figure. I wrapped the strings around my waist and with an extra tug of the strings I managed to hook them together with an "s" hook – no knots! It would be readjusted latter once it stretched out a bit and I'd have to tie it. I attached some nude stockings to the garters and stepped into some flats but was told the French maid dress would have to wait. A very simple dress was pulled out of the closet and I was told to put it on. As soon as I had the dress on and zipped, the doorbell rang and I was told to answer the door. Was she kidding? No wig, no makeup and a guy in a corset and dress was to answer the door? "Sweet Cheeks, I gave you an order. Now hop to it Missy!" And, that is exactly what I did with a reply of "Yes mam." Her voice had never been so assertive before and I responded instinctively.

The lady at the door was a professional makeup artist there to give me lessons. They clearly knew each other so I wondered if she had provided the training in latex and glue, but I did not ask for fear of exposing a secret far more embarrassing than my current appearance. She had brought a small assortment of wigs based on measurements that had been sent to her and one was picked for me. She set up a makeup mirror in the dining room and both of us got make up tips. By the time she left after several hours, I was prolific with the makeup she had recommended and supplied. With a figure, a face and good looking hair, I looked quite passable.

After all that, I assumed the day's excitement was over. Instead, I was presented with a purse, and told we were going shopping. I would drive of course. It seems, I was the chauffeur too. As we drove, my new boss couldn't resist the temptation to needle me. "You know, a sissymaid shouldn't be driving a powerful expensive car like this. You should sign over the title to me and I should trade it in for something more suitably small and feminine. I think a generic POS would suit you well." I was silent, and thankfully, the idea was never mentioned again.

We headed to a uniform shop she had scouted out that had traditional maid's uniforms. She wanted me to try some on and select two. One was a black straight cotton dress and apron and the other was black slacks and a tunic that would be less showy than a frilly sissy maid outfit if one were outside washing windows or on a riding lawnmower. Afterwards we went shoe shopping. True to her word, high heels were required. We ate at a restaurant that evening and headed home for our first evening as boss (she said NEVER call her mistress) and servant. She went on the Internet while I, still in my corset and stocking with new 3 inch pumps had finally changed into my black French maid uniform and matching cap. I sat at the dining room table polishing silverware like a good little maid and contemplating the future. It was lonely.

Later, she joined me in the dining room and we talked about the day's events. I thanked her for all of the work she had put into doing this for me and she said it was because she loves me and it was turning out to be fun for her too. She said tomorrow would be an equally busy day so I should quit for the night, remove my makeup and get a good night's sleep. She asked if I needed help getting out of the uniform and corset and I said no. I told her that, as the maid, I'm the one who is supposed to help her undress. She smiled and said "That's exactly why you are wearing that accessory, Sweet Cheeks! Didn't you know servants are off limits?"

I should have said yes, when she asked if I needed her help, just to be with her a few minutes longer, but I didn't. She told me to wear the straight maid dress tomorrow because we had more shopping to do and to have breakfast ready for her at nine – she will dine alone. I was to eat in the kitchen. She did not kiss me goodnight for the first time since we were married and as she went up to our her bedroom alone I felt truly sad and alone. No doubt she did too.

After the long day, I and the girls slept well even in the small strange bed and room. I was up and dressed by six-thirty and needed the corset to fit into my form fitting maid dress. I finished the silverware, cleaned the dining room table and had a light breakfast for her in the dining room at nine sharp when she came down stairs. She announced that breakfast and lunch would be my responsibility from now on and I would do all dishes. She would cook supper and we would eat supper in the dining room with me serving. We then worked up a menu for the week, something she always had done in her head, and said I would be responsible for the grocery shopping from now on.

She said, "I will go grocery shopping with you today but from now on, you'll be on your own. We will buy you more clothes today as well." She saw no need for the corset with my French maid dress, saying an all in one might do as well but she would reserve judgment until she sees them on me. Either way, I needed more clothes, including civvies' for my days and hours off. So I ended up with two very nice all in ones with garters, more panties, slacks and blouses for off duty times in addition to my small preexisting wardrobe. It was a small, but expensive wardrobe, just enough to keep ahead on the laundry. My French maid uniform was to be worn four or five days a week or even partial days when I would not leave the house except to line dry the laundry or make quick trips to the garden. I could wear the straight maids dress (with corset) if I choose for daily use replacing the French maid dress at my discretion or when it was being washed and the slacks and tunic were for outdoor activities when needed. The straight maids dress for grocery shopping once a week was quickly replaced by civvies'.

This routine went on for two months, which passed uneventfully. Then I asked for it to end. She was right; I had bitten off more than I could chew, but I do finish what I start. After the first few days, it was no longer fun and it is not in my nature to sashay around the house all day in a skimpy little outfit. Well, not all day anyhow. When I tried to slack off on the makeup and wig wearing just the maid cap, I was called on it and sent me to my room to get properly dressed. After the "shut up", that was the only real admonishment during my sissymaid career. It boiled down to too much effort for too little reward. I wanted my life back. I wanted to sleep in my bed with my wife in my room. I wanted to stand up to pee and be able to see while I did it. The girls had to go! I missed my wife and I missed my life.

During the two months, after the initial shock and being told to shut up, I did not complain. I didn't complain about the corsets or girdles or heals, or the garters because I liked them. Even if they hurt, I liked them. I liked the petticoat and the black satin French maid dress. I did not complain about the unexpected accessory. I didn't complain about a sore back, sore legs and sore ankles and feet. I liked the girls, but one can have too much of a good thing. I didn't even complain when she said, whimsically, she had gotten me five inch heels and a Playboy Bunny uniform and volunteered for me to wear it while serving drinks at her makeup artist friend's party. Thankfully she was just yanking my chain, but I said the right thing, "Yes mam". I was mortified, to the pit of my corseted stomach but I said "Yes mam" as a good sissymaid should. Now with the trail period over I awaited her decision.

"I don't know," she said, "You look kind of cute in that little satin dress. I might just want to keep Missy strutting around here in her high heels for another year or so. Husbands are greatly over rated, you know. According to the contract I can continue it for another year. You should have read that more carefully - foolish sissy! I like the obedience. It is truly amazing how obedient you can be. Perhaps we should just renegotiate the contract. Larger maid's quarters perhaps? No wig, makeup or higher heels on weekdays?" She said smiling. "Ok. Seriously, I miss my husband and want him back, even if he is a scatter brained bimbo on occasion. So, it ends! The deal is off, but we might want to reserve every Tuesday for Missy to come by and clean the house if and when she wishes. That way my husband wouldn't have to."

I have no regrets about my short career as a sissy maid. I think I was a good one and the love of my life was a good boss and tolerant wife. We both had some fun, but as a lifestyle, it wasn't for us. I learned things about myself and about my wife and she learned things about me, both good and bad. We both grew from the experience and my trust in her was totally justified. My doubts and fears, which I never voiced to her, were not. She even took back the dish washing duties but I still do most of the work Missy did including the grocery shopping. Some of it still slips through the cracks and we don't worry about it. Life's too short to worry. It was an experience few men will ever have and that's their loss. Do you know what the most amazing thing about this whole episode is? She never, ever said "I told you so".

All my Best,
Missy
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