Domestic Servant

A discussion forum on FetLife about crossdressing seemed like a strange place to solicit a domestic worker. I was wasting time one Sunday afternoon surfing the site, mostly looking at BDSM photos in the stream. Pulling on one of the threads had led me down a rabbit hole that included the subjects of sissies. Although I wasn’t really interested in participating in the kink, I always got a chuckle out of seeing men dressed up like “gurls”. It amazed me how far men go to make themselves look feminine.  The thread focused of “sissy maids”, a subset of the genre in which men are invariably dressed in a black uniform with white trim and a white apron. I thought it was a joke at first when I read the add, “Domestic Servant Wanted.” The advertisement caught my attention because of the tone deafness of soliciting a “servant” and not a “worker”, so I opened up the post. The ad seemed legit,

“Male Domestic Servant Wanted: Perform domestic cleaning tasks like sweeping, vacuuming, and scrubbing countertops, help us do the laundry, help to prepare meals, run errands, help with entertaining, and assist us with other home-based tasks as needed. Previous experience in a similar role is preferred; a High school diploma or equivalent is required; must have a valid driver’s license; be willing to work a variety of hours and days, including weekends; and must have the physical ability to remain standing for most of the day. Must be willing to wear a uniform. In-person interview is required by the couple who would be your employers.” Contact information followed.

I had worked my whole life in the service industry, not as a domestic worker, but quite a bit with hotels. I was unemployed, so I replied to the ad, not really expecting anything to come from it. A few hours later I received a notification via e-mail that I had a new message on FetLife,

“Dear Mr. Smith (a pseudonym I use on FL), thank you for your interest in the position we have available in our home. My wife Jaqueline and I intend to begin interviewing applicants next week. Please forward a recent full-body photograph of yourself, your height and weight, and a current resume. Also, I have attached a survey that will help us with the interview process. Please complete and return it with the other items, We. will be in touch when we have selected the interviewees. Sincerely, Malcom Moore.”

While the ad and the correspondence seemed normal, the survey was truly bazaar. It included questions that were probably more appropriate for a Dominant interviewing a submissive on FetLife than a job in real life. The survey asked for the name on my FL account, which they already had as I had messaged them through FL, and a series of questions that probed my limits. The questions read like an intake form for a BDSM session. “Are you comfortable with XYZ (yes/no/maybe). Honestly, I was more than a little curious about the couple and would have liked to interview just for shits and giggles. Even though there was no way in hell I was going to do most of the things on the list, I nonetheless marked “yes” to all the questions and returned the required application materials.

The next evening, I received a phone call. “Hello Mr. Smith [still not my name]. This is Mr. and Mrs. Moore on a conference call. Is this a good time to talk?” I told them it was. There was a bit of chit-chat, sort of get-to-know-you bander, the Mr. Moore asked if I would like to interview on Wednesday at 10:00 AM. I agreed to the interview and was provided an address. When I hung up, I wondered what I was getting myself into.

On Tuesday evening I selected the clothes I was going to wear, a dark grey three-piece suit, a white starched shirt, a solid blue tie, and the appropriate accessories. I had a fresh haircut earlier in the day and had even gotten a facial and a manicure. The next morning it did not take very long to get ready. The Moore’s address was not very far away, perhaps fifteen minutes, which was a selling point for the position. As I got ready and during the drive, I thought about my answers to the usual questions you hear in an interview: Tell us about yourself. What are your strengths? Why do you want this job? I also thought about the questions I might get about being a domestic “servant”: What experience do you have with housekeeping? Describe your approach to managing household tasks. How do you handle situations when expectations are not met.

The house was the largest one on the block. It had a semi-circular driveway, the kind where you never know where to park the car. I chose as far away from the entrance as possible. Stepping out of the car, I examined the exterior of the house. It was going to be a lot of work to take care of. Straightening my tie, I rang the doorbell. A minute later, Mr. Moore answered the door and introduced himself, “You must be Mr. Smith. [Holding his hand out to shake mine.] I am Mr. Moore. Very nice to meet you. Please come in.” Mr. Moore led me to a study. There was a chair in the middle of the study. He asked me to have a seat and he’d get his wife. A few minutes later the Moores returned. Mr. Moore introduced his wife as Mrs. Moore and they both had a seat on the couch.

Mr. Moore had a hipster-like beard and was wearing a yellow pollo shirt and a pair of black slacks. Mrs. Moore looked a bit like a trophy wife with long curly blonde hair that was tied back and a simple hunter green pleated dress. Mr. Moore was the first to speak. He thanked me for interviewing. He asked me if I had any questions before they got started and I said no. His first substantive words were about “confidentiality.” He said he knew my name was not Mr. Smith, that my resume made that clear, but that he appreciated the importance of privacy. He asked me if I wanted to continue to be referred to as Mr. Smith, and I said it was fine, and in fact it sounded like the name of a domestic “servant” (to use their word). Mr. Moore then spoke to the importance of confidentiality. He said if hired that I would need to sign a NDA, and perhaps the most important qualification for the job was the ability to insure their privacy. I assured Mr. Moore that I had always been a reliable employee and that I would of course agree to any requirements that were necessary to ensure their confidence in him. 

The conversation then took a somewhat strange direction when Mr. Moore said that the idea of building confidence was essential and there would indeed be several somewhat unusual expectations of me. I assured the Moores again that I would do anything that was required. Mr. Moore handed me a clipboard with a document attached to it. It was a standard NDA … identification of the parties, duration, consequences of a breach, and so on. I had signed thousands of them. I noticed the bottom of the document was my real name, so it would be legally binding. I read it over quickly, signed the form, and handed it back to Mr. Moore. Mr. Moore explained the job was full-time, that I would need to be available whenever I was needed, and consequently, I would live in the “servant quarters”, a term that seemed more appropriate for a 19^th century Mansion in Georgia that a split-level home in suburban Connecticut. Thinking if I could break my lease, I might save some money on accommodations. Mr. Moore picked up the clipboard, flipped past the NDA to the next page, and he started asking the sort of questions I was expecting concerning domestic work. I answered the question well I thought. Then, Mrs. Moore spoke for the first time, “Now that we have that out of the way, let’s talk about some of the more unusual aspects of this job. There is a reason we asked for a male servant. Mr. Moore had an affair last year and we agreed we would only hire men from now on.” I put on a serious face and simply nodded as it didn’t seem like an appropriate time for me to speak. Mr. Moore was next, “Mr. Smith, there is a reason we looked for you where we did.” I asked him to explain, and he said, “When I had the affair, Mrs. Moore took revenge by having an affair of her own. This has left us in a quandary. She is not comfortable hiring female maids, which is what we need, I am not comfortable leaving her home all day with a viral male.” A catch twenty-two indeed, I just didn’t understand how I fit in the picture.

Mr. Moore continued, “Mr. Smith, one reason we used FetLife to solicit applications for this position was so we could review the kinks of the applicants. You see, there were two in particular we were interested in that you list among your fetishes.” I asked which ones, and Mr. Moore said, “First, Mrs. Moore really wanted a female servant because she finds men distracting. We noted that cross-dressing was listed as one of your fetishes. We would ask you to wear a maid’s uniform. Second, I it would make me more comfortable if you wore a chastity device. I noticed you list chastity as one of your kinks.” I explained that I had listed chastity as one of my fetishes, but it was a fantasy and I had never actually worn such a device in real life. Mr. Moore was blunt; would you be willing to wear one in our employment? I didn’t know what to say. I mean, I was between relationships, but I could not imagine wearing a cage for very long. I was ambiguous when I replied, “I would consider wearing one, Mr. Moore.” Looking for clarity, he said, “So we understand each other, I would need to know you are wearing the device at all times.” I asked him how that would be achieved, and he said, “By wearing a uniform that shows you are wearing the device.” “You mean you want me to expose myself?”, I asked. Mrs. Moore said, “No not at all. You’d have a uniform.” Mr. Moore jumped in to move the interview along, “Perhaps it would be simplest for you to try the uniform on to see if you are comfortable with it.”

I did not say anything while Mr. and Mrs. Moore took me to the servant’s quarters, which were in a wing that seemed to be almost separate from the rest of the house, a “Mother-In-Law” floorplan, I believe it is called. Opening a dresser drawer, Mr. Moore showed me a collection of chastity devices. There were different sizes and styles. He pointed to them and said, “You can of course choose the one that is most comfortable.” Turning to a walk-in closet, he showed me the uniforms. There were four and they were all the same. They looked like something a woman would wear to an adult Halloween party. Black and shiny, they were trimmed in white lace, had a built-in corset, and the “skirt” would barely cover my belly button, and certainly not my crotch. While I was still studying the uniforms, more like costumes, Mrs. Moore added, “There are a number of accessories as well.” 

I wanted to break out laughing but held my composure. Surely this was a joke. A friend (or enemy) must have set this up. Playing along I asked about the compensation. Stepping out of the closet, Mr. Moore wrote a number on a piece of paper and handed it to me. My jaw dropped. The salary was twice as much as I had earned in any job, and on top of the salary, room and board were included. Mr. Moore clarified, “That figure is for a one-year contract.” Wow, it was hard to walk away from a payday like this one. As I reflected, Mr. Moore said I might want to read the terms of the contract first, and he handed me the document. Much of the contract we had already talked about, but I turned to the details. I paid particular attention to the section that was labeled “Appearance of the Servant”, which went on for nearly four pages. I would effectively be required to be feminized, including having my body hair removed, wearing a wig (if I couldn’t grow my hair to at least shoulder length), having manicures and pedicures, and other beautification procedures. The uniform also required a garter belt with thigh-high stockings, and elbow-length white gloves. I looked again at the figure written on the piece of paper, signed the contract, and shook the hands of Mr. And Mrs. Moore.

I was “welcomed to the family” and asked when I could start. They seemed to be pleased there would be no delay. Mrs. Moore excused herself and said she would make some appointments for me. Once she had left, Mr. Moore said he would feel more comfortable if I was not left alone with Mrs. Moore until I had been fitted with a cage. He also said that couldn’t be done until I had returned from my appointments. Mrs. Moore returned with a piece of paper with a list of appointment times and locations. They were all scheduled for the next day. Mr. Moore said, “You should be finished by 3:00. Let’s plan on you coming here when you are finished.

In the morning, I packed a bag. I put everything I thought I would need for a few weeks, but not very many clothes. I then went to the appointments which were in sequence a chemical peel, brow waxing and tinting, laser facial hair removal, the shaving of my head, a facial, wax hair removal from the rest of my body. After a massage, I had an appointment with a cosmetologist who attached false nails, painted. My finger and toenails a muted red color, and she showed me how to apply makeup, including matching lipstick. I had never had so many people touch my body, and in a way it was exciting. At the end of the appointments, I was left alone staring at myself in a full-length mirror. I was particularly fascinated with my face, which looked feminine. The eyebrows were no longer masculine. Also, my hairless genital looked prepubescent. My penis, an average seven inches when erect, looked out of place. I dressed in my street clothes and checked out of the salon. All the costs had been prepaid.

I went straight to the Moore’s home. I kept seeing my bald head in the mirror and thought someone was in the car with me. Mr. Moore saw me drive up and met me at the door. He suggested we go to my accommodations and “get dressed”, which appeared to be a euphemism for putting on a cock cage. Indeed, the first thing he did was open the drawer and ask me to select a chastity device. He said, “If it does not fit well, you can change it out later.” I had no experience, and pretty much randomly selected one of the steel caged. I was directed to the restroom where I put the cage on in privacy. When I came out, Mr. Moore asked for the key, and I handed him the key. “I need to know this key fits the device you are wearing. Would you please disrobe?” In for a penny and in for a pound, I thought, and I removed my clothes. On one knee in front of me, Mr. Moore inserted the key in the device, removed the lock cylinder, then reinserted it and removed the key before putting it in his pocket. “Great, let’s try on your uniform.” I had never worn woman’s clothing and Mr. Moore watched me as I struggled to figure out how everything went together. The corset was particularly challenging as it had to be adjusted before the outfit was put on. It took me a good twenty minutes before I was wearing the dress, petticoat, garter belt, and stockings. I selected a pair of black leather flats that fit my feet and put them on. Mr. Moore pointed to a drawer and where he said I would find wigs. There were four, all the same, long and wavey brunette. I put one on and studied myself in a full-length mirror. I looked like a girl, except for the give-away cock cage.

By now it was nearly 5:00. Mr. Moore said it would take some time for me to learn their routine, but he always enjoyed a cocktail with Mrs. Moore at 5:00 each day in the sunroom. He showed me where the bar was and explained that he almost always had a dry Beefeaters martini with two plain green olives and Mrs. Moore would have a gin spritz with Tanqueray, prosecco, and apple juice. I knew my way around a bar and said I would bring the drinks if he’d point out where the sunroom was, which he did. It took about ten minutes to find my way around the bar, make the drinks, and find my way to the sunroom. Mr. and Mrs. Moore were in chairs across from each other. I apologized for the interruption, brought Mrs. Moore her drink first, then gave Mr. Moore his drink. “Thank you, Miss Smith, that will be all for not,” Mrs. Moore said. Was it a mistake that she had called me “Miss.” I excused myself and went to the bar to clean up the mess I had made. When I finished cleaning up, I went to the sunroom to ask if the Moores needed anything, which they did not. Mr. Moore told me they would be going out for dinner. Mrs. Moore suggested I explore the kitchen. They would be back about 9:00 PM and they might want a nightcap. 

Before the Moores left for dinner, Mr. Moore explained there was a buzzer and a map for the floorplan for the house in my room. If they needed anything, they would ring me and I light on the floorplan would indicate if the buzzer was rung in the living room, entertainment room, sunroom, study, kitchen, or the backyard by the pool. Mr. Moore said he also had my phone number and would text me when they were coming home if they would need anything when they got here. Before leaving, the Moores suggested I explore the house and make myself feel at home. I had been kept busy while the Moores were in the house, but when left alone, I became self-aware. I was embarrassed by the situation I found myself in. I was walking around like a sissy with a cock cage in plane view. I was comforted by the fact there was only two people who knew what I was doing, the Moores, and they were paying me a shitload of money.

I received a text at 9:18 PM from Mr. Moore. He said they would be home in about 15 minutes with a friends, a couple, that they had run into at the restaurant. Mr. Moore said they would like to share a bottle of wine and I should open a bottle of 2010 Louis Latour Corton Grancey to breathe. “The wine is in the cabinet against the wall where the bar is.” Still dressed in my sissy outfit with my cock cage in plain sight, I asked what I should wear. The response gave me chills, “What you have on is perfect.” I knew the contract stated I would help entertain, but I never imagined I’d have to be dressed the way was. As I uncorked the wine and took out four glasses, I I thought about how I should cope with the situation. I reached behind, poured myself a glass of some single-barrel Kentucky bourbon I did not recognize, and fortified myself. I laughed to myself I needed to pull up my “big boy pants” (I wasn’t wearing pants) and suck it up. I saw headlights flash across the living room window and went to the front door to welcome my employers and their guests.

The Moores guest came through the door first, a busty woman with long straight blonde hair who glanced at my outfit and smiled when she saw the cage and an older man in a suit and jacket who made eye contact before passing me his overcoat. The woman then handed me a fur stole. The Moores entered next. They smiled as they handed me their coats. Mr. Moore introduced their guests as the Kays and said I could serve the wine in the living room after I put the coats in the hall closet. I quickly stowed the coats and served the wine. I had placed the glasses on a tray which I skillfully carried with one hand while I carried the bottle of wine in the other. Placing the items on a credenza in the living room, I poured a tasting amount of the wine and brought it to Mr. Moore. He swirled in in the glass, got a whiff, then tasted the wine. “Delightful.” “May I serve the wine, Sir?” I was trying to be as professional as possible. “Yes, please Miss Smith.” He was calling me “Miss” too. I divided the bottle evenly between the four glasses and served the wine. I stood by the credenza until Mr. Moore said there would be nothing more at this time. I went to my room.

About 10:10 the buzzer went off. The light for the living room was illuminated on the floorplan map. I went there and the four were still seated. Mr. Moore addressed me, “Miss Smith, would you please serve us a nightcap? Mr. Anderson would like to have the Macallan 15, his wife would like to have a Manhatten, and Mrs. Moore and I would like to have an Old Fashioned, made with Bulleit, please.” “Of course, Mr. Moore.” It was clear Mr. Moore took note of my experience bartending and was exploiting that to impress his guests. I prepared the four drinks as quickly as I could, but it still took more than fifteen minutes. When I returned, Mr. Moore seemed to be agitated. I had taken too long to prepare the drinks. I preemptively apologized for taking too long and while making no excuses I said I would make sure I was more efficient in the future. I heard Mr. Moore apologize to his guest and explain this was my first day. 

About a half hour later, now about 11:20, the buzzer went off again. Glancing at the floorplan, I headed towards the living room. On the way I overheard conversation, and it seemed like the guests were getting ready to leave, so I picked up the coverings from the hallway closet on the way. The four were standing in the entryway. I helped Mrs. Anderson on with her stole, helped Mr. Anderson with his coat, and I opened the door. The guests hardly glanced at me as they walked by and the Moores bid goodnight. I closed the door. Mr. Moore turned to me and said I had done a very good job for my first day. I apologized again for taking too long to make the mixed drinks and I promised to study the bar and be better prepared in the future. He said he knew I would be. As an afterthought, I confessed, “Mr. Moore, I would like to tell you that I poured myself a glass of whiskey just before they came home to fortify myself because of my appearance.” He responded, “Most of our close friends are very aware of the arrangements we have with our servants. Don’t make a habit of drinking my liquor.” “Yes, Sir. Will you be needing anything else tonight?” “No Miss Smith, see you in the morning.”

I went to my room, took my costume off, washed the makeup off my face, and took a shower. I sat on the edge of my bed thinking about my new job. What if I were called in the middle of the night and wasn’t dressed in my uniform? When should I get up? I felt I had little idea what my chores were. I set my alarm for 5:00 AM and laid out a clean uniform before falling asleep.

In the morning, I showered, put on my makeup, dressed, and put on a wig. I went to the kitchen about 6:30 and started investigating the equipment and provisions. The refrigerator was well-stocked. I wondered if it was my responsibility to keep the cupboards filled. Just then Mr. Moore entered the kitchen. He was still dressed in his pajamas. “We need to meet this morning to discuss your responsibilities, Miss Smith. How about 10:00 in the study?” “Yes, Sir.” He followed up, “In the meantime, Mrs. Moore and I both take our coffee black. We’d each like a mushroom omelet, wheat toast with butter and jam, and some orange juice. We’ll take our breakfast in the sunroom.” “Yes Sir”. It took me about twenty-five minutes to make the meal and serve it. Mr. Moore was still in his pajamas. Mrs. Moore was dressed in a low-cut lace negligee that did a poor job covering her large breasts.  She thanked me as I served her.

I met Mr. Moore in the study at 10 as he had asked. He was sitting behind his desk flipping through a. three-ring notebook. “Miss Smith, this notebook describes the schedules and protocols for the house. It explains in some detail what your responsibilities are. Please read it cover-to-cover and let me know if you have any questions. I will give you the rest of the day off to study. Please plan on cocktails at 5 and dinner at 7. You can join us at 5 and I will answer any questions you might have. We’d like a pasta dish and green salad.” I returned to my room and studied the document. My attention was drawn to two sections. The first concerned “entertainment” and the other “errands”.

I was drawn to the subject of “entertainment” because it meant expansion of the sphere of people who would know about my feminization and chastity. My experience with the Kays had not been particularly traumatic, I suppose because they were of similar age and the Kays seemed to be in on the joke and didn’t overtly embarrass me when I greeted them. But my mind took me to places where I might be deeply humiliated. I also noticed the section labeled “errands” because I was terrified by the idea I might be recognized in public. The section simply said, “Responsibilities can include running errands like grocery shopping or picking up needed supplies, among other things.” Surely, I wouldn’t be expected to go out in public in my uniform.

I prepared a martini and a gin spritz and located the Moores in the sunroom at 5:00. After serving the drinks, Mr. Moore invited me to join them, and I used the opportunity to get clarification regarding my responsibilities. I asked about “entertainment” and Mr. Moore explained that in addition to serving small groups of close friends, like the Kays, I would be called upon to help with larger parties, including their annual costume party in May and their Christmas in December. I asked about “running errands” and was told that mostly involved grocery shopping. I asked what I should wear for the parties and the errands and Mr. Moore said without hesitation, “Your uniform, of course, Miss Smith.”