Heels by Missy


Heels by Missy


Clarisse and I had been married for almost 20 years and had reached a stage in our marriage where everything was comfortable but not that exciting anymore. We had sex occasionally but it was pretty average and seemed to be just a formality rather than the passion it evoked when we were younger.  Clarisse had worked a few years and then decided to stay at home and be the typical wife. She took care of the house, enjoyed her hobbies, volunteered for charities, and kept herself trim and healthy. Even in her late 40s, Clarisse was still very attractive and her dark complexion showed few wrinkles and highlighted her green eyes. She was tall, nearly 5’8″ and although heavier than when we first married, was still slim in appearance. Her dark brunette hair was always well kept, and she liked to be fashionably, although conservatively dressed. She had maintained her curvy body and her 34B breasts looked fantastic when she was nude. I had worked long enough in my career and had been lucky enough with my investments where it would be possible for me to retire early.  My career had been fun when I was younger but it had begun to be more demanding than rewarding and I found little that I liked about it now.  Since we had saved sufficiently and had no debts I took the plunge.


The first year or so of retirement was just about everything that we expected, with some sightseeing travel and puttering about with house projects. I was also able to focus on improving myself, losing almost 15 lbs. since retiring. That got my weight down to 155 lbs., which was less than I weighed when we first married and made my 5’7″ frame look very trim. In contrast to Clarisse I was very light skinned, with blue eyes and dark blonde hair, just tinged with gray. Only one thing about my retirement bothered me. When I was working I had many business trips during which I could indulge my secret fantasy of cross dressing. Now those opportunities were gone. Rarely was Clarisse away for more than a few hours and I could never really relax if I dressed at home. I had been open with her about my dressing desire, telling her about it even before we married. Despite my efforts to get her to accommodate it however, she never really accepted the fact that I like to dress and so I kept it to myself.  We also struggled with assigning household chores. Clarisse had done the majority of them when I worked, but now felt we should split them.  I couldn’t really argue with that logic, but didn’t enjoy doing my share at all. The majority of tasks still felt like woman’s work, and as I did them I often thought of my cross dressing. The chores seem to fuel a desire to appear feminine while I did this typical woman’s work. Finally I thought of a solution to both my problems and decided to present it to Clarisse while we ate dinner that night.

“Dear, I want to offer you a proposal for our house cleaning needs. I will agree to do them all, one day a week, working the whole day. I’ll do your chores as well as mine. That will provide us a clean house and we will only have to do minor cleanups in between. You can spend the entire day out of the house. You can go shopping, visit friends, or go to museums or art shows. All the stuff you love to do when you have free time.”

“Are you serious? You will really do all the housework? That would be wonderful. You know I hate it, since I feel like I’ve been doing it forever. But why are you volunteering to do it now?  I know for a fact that you dislike it as much as I do, if not more. Are you planning on hiring a service to come in that day?”

“No dear, I’m not hiring someone else to do it, as we decided our retirement budget wouldn’t allow that luxury. However you are right, I generally find the chores to be dull and a waste of my time. But I have also missed expressing my feminine side by dressing up. We always seem to be together and since you don’t like it, I can’t wear my female clothes at home.  This way, I can dress up for an extended period and you will not have to see it. But I’ll also be doing something useful, cleaning our home. You will no longer have the burden of housework, and I’ll find it more interesting since it will give me activities to do while I’m dressed.  I know you don’t like me to do that, but at least you will be getting some value in return. Are you open to trying this?”

“I don’t know Nathan. I mean it is a wonderful offer to do all our chores, but even if I’m not here, I’ll be thinking of you dressed as a woman. It may seem innocent to you, but it does leave a mental image for me. However, I am willing to try it once or twice to see how it might work. Of course, I will have to give you a list of all the chores I expect you to complete and if you fail to do so, then that will be the end of this little experiment. I’m not going to just let you dress up and prance about pretending to be a woman and playing at housework. I’ll have standards you will have to meet. Are you agreeable to that?”

“I think that is fair. I mean I know generally what needs to be done, but you have run our house for 20 years and know what is essential to keep it clean. So work up a list, and give me some notes as to how and what to do for each chore and I’ll do my best. I want you to be satisfied with my work. I know you are allowing me the freedom to express my secret desires, so I want you to feel that you are getting a good return for that.”

With those requirements laid out, I began to plan my household day. We agreed that Wednesday would be a good time and Clarisse made up a chore list. She also arranged to go shopping and to a movie with her best friend Sharon. I had determined what to wear and as soon as she left to pick up Sharon, I began to get dressed. I decided it would be best to keep it simple, and wear something that it would be easier to work in. So I wore a light pink blouse, plain maroon skirt, and a matching pair of maroon pumps with a 2 ½ inch heel. Underneath I wore a set of beige bra, panties, and girdle brief and light tan pantyhose.  I had much fancier lingerie but I wanted to focus more on the chores than getting dressed this first time. I worked easily through the list of chores, taking only a short break at lunch. Unlike previous times, I almost enjoyed the housework this time. The feel of the hose, the tightness of the bra and girdle, how the skirt felt against my legs and the click of my heels as I moved about, all satisfied the inner need I had to express my femininity. It also seemed to be reinforced by the chores. I know they aren’t just woman’s work, but it seemed more appropriate to me to be dressed as I was. I was able to complete the list and get changed almost a full hour before Clarisse returned. She had really enjoyed her day out and was mostly pleased with my efforts.

“Nathan you seem to have done all the chores and in most cases did them well for the first time. I think if I give you a little more training you will be able to meet my specifications. Did it take you the whole day?”

“No I took about an hour break for lunch and was done almost an hour before you returned.”

“Good, I think you can handle a few more chores, like the laundry, and still do a reasonable job. I hope you don’t mind but Sharon and I made plans for next Monday. We are going into the city for some afternoon shopping, then dinner and take in a play. I will be home later but that should give you more time as well.”

“Sounds okay to me, I’m just glad you are finding this arrangement acceptable.”

The next Monday everything went as planned. Clarisse gave me a much more detailed list of chores, including a critique of my first day’s work. She was very specific on how she wanted everything done plus added the laundry. It took me more than a full day, but since she was staying late in the city, I still completed the list.  I had also worn something a little less practical, a black and white dress with a tight skirt, matching black lace lingerie, a garter belt with stockings, and full 4 inch heels. I had to move more deliberately in the heels and tight skirt but again loved the feeling of the feminine clothes and thoroughly enjoyed the day.  Clarisse checked my work early the next day and again found some shortcomings but we agreed to schedule another cleaning day the next week.

However, the following Monday didn’t go as well as I hoped. About half way through the day, Clarisse called and said she was coming back to the house. I protested that I wasn’t nearly done with the chores, but she insisted. I hurriedly changed out of feminine outfit, but continued to finish vacuuming the house since I had started that chore.  When she arrived, I questioned her on why she came back early.

“I know I promised to be gone all day, but I finished shopping earlier than I expected, the art exhibit was not up to par and there was nothing left to do. I appreciate your willingness to be the housekeeper, but I don’t want to feel like a refugee for the day. It defeats the purpose of having you do the chores if I must fritter my time so that I can be out of the house. So how about next time, you dress as you desire and I’ll stay here? I already have a mental image of you in dresses, so seeing it in person won’t be much different. I can also give you more effective training if I can see you do the chores. I mean I’ve tried to tell you how to mop the floors, but every time I return they look sloppy. It is that or we go back to sharing and you forfeit dressing up.”

Although I wasn’t sure about her being there and how she might really feel about my dressing once she saw me, I had enjoyed the release so much I didn’t want to give it up. So we made plans for me to clean house that Friday, since I had not completed all the chores. Friday morning I got up early and took a shower and began to get dressed. I had chosen one of my most conservative outfits as a precaution against offending her. I wore plain white bra, panty and long-leg girdle with tan pantyhose. My skirt was a knee length, gray plaid A-line design and I wore a long sleeve white blouse and gray 3 inch heel sandals. I was really nervous when Clarisse first saw me, but she only smiled and told me the first chores to do. I started with the laundry and changing the bed linens. She then spent 20 minutes or so showing me exactly how to mop the kitchen floors. I saw where I had made my mistakes previously and finished the morning mopping all the bathrooms and wet mopping the hardwood floors, breaking only to handle the laundry. Clarisse had generally just watched me briefly and then gone on about her activities, checking emails, handling bills, and reading a novel. Finally, about noon she came in the laundry room.

“Nathan, I think we need to discuss this experiment. How about you make us lunch? A nice light salad with rolls and a white wine will do and you can serve me in the sunroom. Then we can talk about it.”

I agreed and went to begin making our lunch, but I was full of misgivings. I had feared this. She was obviously displeased with my dressing and despite her optimism going into today, had found it more disturbing to see me dressed than she expected. I tried to think of options as I took our lunch to her. At first we sat and ate silently, with the only conversation being her complimenting me on the salad.  Finally when she had finished, I topped off her wine glass and she indicated that we should talk.

“Dear, I must admit that seeing you in skirts was more shocking than I expected. I guess I had one vision in mind but you appear much different than I expected. For one thing, you have very shapely legs and they look good in heels. Second you move with more grace and feminine mannerisms than I would have ever thought possible. I expected you to clomp around and almost be a caricature of a woman. But even though you are better than I expected, you don’t really look like a woman. You lack the curves most women have. I see that you are not wearing makeup and have done nothing with your hair. Do you not have any cosmetics or a wig?”

I took a minute to answer, taking a slip of wine for courage. I wasn’t sure where she was going, as her comments were more positive than I had expected but I heard her tone of disapproval.

“I do have a wig, but all my cosmetics are old. I generally haven’t worn them or my wig, as I rarely dressed for extended periods before. Also, the wig can be a little tight and hot. Finally, I had always wanted to be able to slip out of my female appearance as quickly as possible in case someone came by.”

She nodded as I spoke. Looking me over again she smiled as she spoke.

“I guess I can understand that. Is that why you haven’t shaved your legs as well? I mean they would look so much better if you removed that nasty hair. Even expensive hose look dreadful with hairy legs. I suspect that your overall appearance would be much nicer if you shave off your body hair. Now that I have seen your attempt at appearing female I think you need to make a decision.  If you are to continue to dress and be the housekeeper, I‘ll expect you to commit to a proper appearance. That means shaving, wearing makeup while dressed, wearing a wig, at least until your hair is long enough to put in a woman’s style, and using crèmes, moisturizers, and lotions to soften your skin. There are padded garments and body shapers available that would give you a woman’s appearance. I think if you work at it, you could be passable as a woman. Then I can accept your cross dressing as it will be more of a true representation of a woman than a crude imitation. I assume you have a collection of clothes? I want to see them, so I can judge what else you might need beyond cosmetics. Get them out for me and put them on the bed. Then you can take a nice bath and remove that body hair. Otherwise, I suggest you go upstairs and put on some of your old slacks and a shirt to finish your chores.”

With that she took a slip of wine and looked at me smugly over the rim of the glass. I had hardly expected that appraisal. I mean I was ready to argue why I should be allowed to continue dressing, but not prepared to argue against becoming more feminine. I had thought often of shaving myself. Every time I would work stockings up my legs, I would imagine how they might look smooth and silky. I also enjoyed wearing some cosmetics like lipstick. So the idea certainly appealed to me. But it was also frightening. It meant stepping over the line and not being able to look completely masculine anymore.  I decided since she had suggested it, that I would go for it.

“If that is what you think would be a good idea, I’ll be upstairs in a minute. I just need to clean away these dishes. I’ll get my clothes and start the bath water.”

I tried to sound like it was not a big deal, but my heart was pounding. I was more nervous now than earlier today when I first stood before her in my skirt and heels. I quickly cleaned up the lunch and went to the spare room where I kept my clothes. I opened the case and put the items on our bed. It was mostly lingerie; I had only six skirts and dresses. I did have a fair number of heels, a total of 10 pairs; shoes were always a weakness for me. I had just finished organizing them by item and started running the hot water for my bath when Clarisse came upstairs.

“Nathan, if you still have that clipper that you used when you had a beard to trim, I’d suggest you get it. That will allow you to remove much of your body hair and make shaving easier.  Find that and remove your clothes for me.”

I did as she asked and used the clippers to remove most of the long hair on my legs, chest and underarms. Clarisse came in, quickly looked me over and took the clippers.  She reached up and trimmed off my sideburns and hit a few spots where I had missed some hair. I thought she was done, but then she ran the clippers through my pubic hair. She trimmed the hair on my balls and cock and cut through the patch above my cock leaving only a narrow strip.

“Just be sure to shave everywhere you trimmed, you want to look as smooth as possible. When you’re done, I expect to see only your cute little landing strip for body hair. After you get out of the bath, apply lotion everywhere you shaved. You need to get used to applying lotion when you shower or bath. I know you don’t have any cosmetics and my skin tone is a little too dark for you, but I’ll use what I can today. Then, I’ll sort through your clothes and leave something for you to wear.”

I followed her instructions and was soon shaved smooth. Applying the lotion I was struck by how much my body looked different now.  The lack of hair made my skin look much softer and the modest body fat I had made my chest look more like breasts than I had noticed previously. Similarly the shaped pubic hair gave me a more feminine appearance there as well. Slipping on a robe, I went out to see Clarisse. She had gone through my things, and picked out an outfit. It was a red skirt with a matching red and white sleeveless lace top. I was a little surprised as the skirt was the shortest one I had, reaching to just mid-thigh. She was holding a white waist nipper and asked why I didn’t wear it.

“Well it is a bit too small and I found it uncomfortable to wear.”

“Well I would like you to try it for me.  It will give you a more defined waist and help you look more feminine.”

She added it to the pile of lingerie which also included white pantyhose and the bra and girdle I had on earlier.  She had me sit down at her vanity and applied some blush, eye shadow, mascara and lipstick. She told me that I really needed foundation as well, but that she would have to buy a lighter shade for me. She then fitted the wig on me and told me to get dressed and be sure to pad my bra. I followed her instructions including the waist nipper which made it hard for me to breathe. I met her downstairs.

“Nathan that is much better. You look more like a cleaning lady already. I really think we should keep your skirt length as short as possible, as your legs look darling without that hair. Also having your waist pulled in makes a big difference. I’m going to look at other padding options as well. You can work on more of your chores while I go shopping for your needs. I will be back by 6, so plan on making supper at 7.”

I worked the rest of the day, trying to complete my chore list, only taking a break late in the afternoon to put together a chicken and rice casserole. Even though I worked constantly, I still had not finished all of my assignments when Clarisse returned. She had me retrieve the packages from her car, admonishing me not to look in them, and put them in our bedroom. I started the casserole and then brought her a drink.

“Dinner will take about 45 minutes. I’ll just slip upstairs to get out of these clothes and then join you for a drink.”

“Not yet Nathan, I think it would be best if you remain in your working outfit for now. I rather enjoyed having you serve lunch to me today and would like you to make it part of your service. Let me see your chore list. Although you’ve made good progress on your chores, there is still much to do. I think it might be a good idea for you to plan on working the next few days on learning how to take care of the house and how to present the proper image. I was able to get you most of what you’ll need to appear as I want you and it will help to practice applying your cosmetics if you do it more than once a week.”

“But can’t I at least slip out of this waist cincher. It’s cutting me in two, making it hard to breathe. I can’t imagine eating with it on.”

“You silly girl, that’s one of the benefits of waist shapers. If you can’t eat as much, then it will help you get thinner until it feels more comfortable. Also, I bought another one. They will be a staple of your uniform for a while, so you will just have to get used to it.  It will also remind you of what women were expected to do to meet men’s expectations of their appearance. We have to endure all types of adjustments, modifications, and alterations just so they will find us pretty and sexy. I mean isn’t that what you wanted? Or is there some other reason you wanted to dress up?”

“I do like foundations, but this seems so tight. The primary reason I liked to dress is that I have a longing to wear heels, hose and skirts. There is something about them that seem so right to me. I can’t really explain it but get such satisfaction when I wear them.”

“Well Nathan, then you should enjoy the next few days, I expect you to be fully dressed the whole time. By the way, calling you by your given name when you are dressed as a woman seems wrong. Do you have another name you use when dressed?”

“I’ve always thought of myself as Tiffany, so I guess that would be it.”

“Oh my, that is hilarious. You think of yourself as a Tiffany, you must be kidding. That is a name more suited for a girl or young woman. I think you are a bit too old for that. We need a name that is more from our generation. What is it that the British call their pansies?”

“I think they refer to them as Nancy boys.”

“Yes, that is it. I think Nancy would be about right. Put out one place setting on the dining room table. I want you to serve me tonight. You’ll need some pointers on how to properly serve. After I’m done you can eat in the kitchen. How about a refill, Nancy and let me relax until dinner is served.”

I was totally surprised by this turn of events, but dutifully followed her orders. Dinner went well; she liked the casserole and instructed me on how to present the food, clear dishes and refill drinks. It felt a bit odd, eating by myself in the kitchen, but I soon had everything straightened out and went upstairs to see what she had bought for me.  I stripped down to my panties so I could try on the new items. We went through the purchases, one by one. She had bought another waist cincher, this one in nude and had bought other matching shape wear and bras in white and nude. To make me curvier, she had found a padded girdle that gave me a rounder rump and wider hips. The lace bras were all a c-cup. My other bras were only b-cups, as I had been partial to smaller breasted woman, but she felt a larger size was better suited to my frame. For my uniform, she had an assortment of short skirts, one each in black, navy blue, pink and pale yellow. Each skirt was paired with a short-sleeve or sleeveless top that had trim in a matching color. After trying them on to ensure they fit, I put them in my closet or dresser. Along with the clothes, Clarisse had bought a complete line of cosmetics, appropriate for my skin color. She took some time to show me how to apply each one, but said tomorrow I would need to do it all myself so as to learn the techniques. She topped it off with a couple of short diaphanous baby dolls.  I changed into one and after applying my nightly face crème and some skin lotions I went to bed.

The next few days were a whirlwind of activity. I started each day by rising at 7, getting cleaned up, dressed and made up. I then went down to work on minor chores until Clarisse arose at 9. I would get her breakfast and start my daily chores. She seemed to be more demanding each day, either adding more chores or making me work harder on each one to satisfy her. Surprisingly she kept extending my time in skirts and insisted I do this routine for the next month, I learned all the household skills and began to develop some flair for cooking, learning a new recipe Clarisse would suggest each day. My only time in male clothes was to run errands. I did buy matching heels for each of my new skirts, at her insistence, and was becoming quite proficient at my cosmetic applications. I also got my ears pierced at a shop in the mall. She had also ordered a new wig and a pair of breast forms which came in the mail. She delighted in my new bust and complemented me often on how curvy I now looked.  She especially liked me to attach them with the adhesive and wear them under my baby dolls. My skills extended to cosmetics where I could apply them and began to look passable as a woman. I also lost nearly 5 pounds since I rarely ate full meals with my waist cinched in.

Although this was somewhat of a dream come true, wearing heels and skirts so often, I began to get a bit tired of it. I mean heels are sexy, but doing chores all day, every day took a lot of the appeal away.  By the end of the day my calves and feet ached. Also the added effort to shave, moisturize my skin, and apply and then remove cosmetics took much of my free time. It seemed I rarely did anything I wanted on my own.  But I knew that in another week, a break was coming. For almost a year, I had planned a trip with a couple of my college buddies to volunteer at a national park helping them catalog old documents and artifacts. It was originally planned as a way to see old friends and do some nice volunteer activity. Now it would also be a break from my constant female experience.  When it came time to go, Clarisse agreed to let me take only male clothes and I was determined not to shave anywhere for the whole two weeks.  I hadn’t realized how nice it was to let everything go and not have to worry about keeping my hair, skin, and nails so neat and pretty.  On the flight back, as I sat in the plane scratching my scraggly beard I planned what I was going to say to Clarisse. I now knew how to keep the house clean and could do it with no more than 2 days a week. I would tell her that I would keep myself presentable, but would not dress as a woman all the time. Also, I could wear opaque tights, and high collar, long sleeve blouses to avoid shaving. I had it all worked out.  When she picked me up at the airport she gave me a big hug and smiled at me. We got in the car and started the drive home.

“Nathan I missed you so much. I didn’t realize how much I’d come to depend on you around the house. I have to admit the house is a mess. The laundry is overflowing and everything needs to be dusted, mopped or cleaned. I see you took your male fling seriously, although I hope you realize how silly that patchwork beard looks. With your long hair it makes you look like a vagrant. I understand your desire for male bonding with your friends, but it’s time now to resume your household responsibilities.”

When we arrived home, we left the luggage in the trunk. She had a surprise for me. She took me by the hand, told me to close my eyes and led me down the hall, past the kitchen. I could sense we were headed to her old sewing room next to the laundry, but had no idea why. Finally she pulled me into the room and said I could open my eyes. I was shocked at what I saw. The wall separating the sewing and laundry rooms had been partially removed, forming a larger room with only a doorway and a waist high bar separating them. The sewing room had been changed into a small bedroom, with white furniture. It now held a single canopy-bed, a vanity with mirror, and a lingerie chest. A small television was mounted on the bar. A white chair rail ran around both rooms lined with wallpaper of large pastel-colored spring flowers below it and light yellow paint above.  I looked around hoping this was not what it looked like. Finally I turned to look at Clarisse.

“Isn’t it cute?  I had a contractor come in and do everything while I shopped for the furniture and accessories. The room was a mess for a while but it turned out just like I designed it.  I knew you needed someplace like this. Once I began to see how beneficial you were to the household, how I really enjoyed having you take control of the day to day maintenance, and how you were beginning to fully adapt to a female role, I felt guilty about having you confined in my bedroom. I mean I wanted you to be up early, so as to be ready to serve me when I awoke. But that meant you had to sneak around to take your shower, do your hair and makeup, and get dressed, all without making any noise to wake me. Now you can get ready, as you please with no chance that you’ll bother me. Also, by combining it with the laundry, you can iron later at night and still watch TV or relax in your own space. I also had the bath across the hall styled the same way, using the same paint and wallpaper scheme and updating the fixtures to a more feminine style. It’s like you have your own maid quarters. I also have another surprise for you upstairs in my bedroom. But first, I want you to strip out of those inappropriate clothes, take a shower and get cleaned up. That means shaving fully too. Your male adventure is over, and it is time to return to your new feminine identity.”

Clarisse was beaming. I couldn’t believe what she had done, but found it impossible to protest without hurting her feelings. I could tell she had invested a lot of time and energy in this makeover and to flatly reject it would be hurtful. So I figured I would go along for now and once I dropped back to a 2-day schedule, I would use this area during that time. I took off my clothes, which she asked me to give her, and went to take my shower. The bath was as she described it and was fully stocked with all my personal, female-based, items. I was a little sad to shave off my body hair and beard, but again consoled myself that it could grow out at any time.  Once I was all smooth and clean, I dried my hair and put it in a ponytail as I had when I was with my male friends, but this time it was higher up in a feminine look. I put on some light makeup, slipped on the robe and high-heeled slippers Clarisse had left for me and went up to our bedroom.  She was sitting in the large stuffed chair by the window. A dress bag and a couple of wrapped boxes were placed on our bed.

“Oh Nancy, that looks much better. I bet you feel better too. Nothing feels as nice as smooth skin after you shave. I see you haven’t forgotten anything about your makeup either. What I really like is how long your hair looks; we need to get you to my stylist so you can have your own hair-do and stop using wigs every day. But first I have a special treat for you, a couple of welcome home gifts. Go ahead you can open them.”

I opened the larger box first. Inside was a steely-gray lace corset with a built-in bra and attached garters. There was a tiny lace G-string and some lace-top stockings as well, both in a matching gray shade. The second box contained a pair of gray pumps, coordinated to the lingerie. Finally Clarisse told me to open the dress bag. I took out a gray cotton dress trimmed in white eyelet lace; there was also a white half-apron and hair band pinned to the hanger. The dress had a full skirt, flared out from the hip, but short. The sleeves were just elbow length and it had a V-neck with narrow collars. The hem, cuffs and collar were all trimmed in a white eyelet lace, with a gray satin ribbon woven through the lace. The trim was repeated on the apron and hair band so they all matched.  It was obviously a maid’s uniform.

I would have absolutely loved it before; but now it reflected a change in my life. It would not be just a darling feminine outfit, to be worn for sexy effect. It was a true uniform; one that Clarisse certainly expected me to wear when I served her. But again, I couldn’t bring myself to object, her feelings were still very important to me and the outfit was appealing. I could see her smile and knew she expected me to love it. So I gushed over how pretty it was and did as she suggested and started putting it on. She tightened up the laces on the corset, showing me how to do it, so I could achieve the same look by myself. Even though I was now as skinny as I had ever been, the corset was very tight; it had reduced my waist to about 26 inches, down from my normal 30. I knew if I wore it often I would invariably loose more weight as I couldn’t imagine eating anything while constrained like this; I could hardly breathe with it on. The bra cups had gel pads so I had a bit of cleavage with my smooth chest. The stockings slid up my newly denuded legs and I must admit I loved how they looked. The G-string was another matter. I had never liked this style of panty as my cock, although not big, never stayed restrained by the small triangle of cloth in front and you couldn’t really tuck yourself. It covered me when I put it on, but I knew as I moved around my penis would be dangling outside of it. With the lingerie on, I slipped into the dress. It fit perfectly, as did the shoes. With the apron and hair band, I looked completely like an upscale maid. Clarisse was ecstatic.

“Nancy that looks so pretty; it is even better than I imagined. Don’t you just love it?  I felt like you needed something special, something as a reward for becoming my maid, something that would give you pleasure when you saw yourself. It took me a while to find the right combination but it think this is just about perfect. What do you think?”

“It is beautiful. I’ve never seen a prettier, sexier maid uniform. It is so nice, but you didn’t have to do this for me. I would have been satisfied with my old outfits, but thank you for being so thoughtful. My only concern is the panty. I never really liked G-string styles. I mean they look sexy at first, but when I move they don’t hold me in place down there. I told you that when we were looking at lingerie before.”

“I knew you would say that, but I have a solution that I’ll show you in a minute. I just wanted you to have that sexy, bare butt look under your skirts and knew that a G-string would look so cute. I had faith that you’d love the uniform and lingerie as much as me, so I ordered five more complete sets. All you have to do is go select the colors. Although from the looks of it, I’d suggest you could also have them hem your skirt an inch shorter. The more you can show off those pretty legs the better. Now let’s take care of your issue with the panty.  Come stand in front of me and I’ll take care of your concerns.”

I did as she asked. Clarisse told me to lift up my skirt and then she reached up and pulled down the panty. She opened a box that she had on her lap and took out a small metal device. Grabbing my flaccid penis, she worked the device so that a metal band fit tightly behind my balls and around the base of my penis. The shaft was pushed into a triangular sheath that curved downward. Once my penis was secure in the sheath, she ratcheted the band until everything was held snuggly and then used a small lock to secure the band and sheath.  She tugged on it lightly and it was apparent that it was not coming loose, so she pulled up the panty which now nicely covered the triangle sheath.

“How about that for solving your concerns? You shouldn’t have any problems now with your little manhood flapping about. I thought about your comments and came across this on the internet while looking for something else. I knew when I saw it that it would solve your issue with G-string and thong panties. How does it feel?”

I couldn’t believe what had just happened. I thought I could just get her to buy a hipster or bikini panty that would be snug for me. Her choice of a chastity device was totally unexpected. We had never discussed this and I didn’t fancy having my cock locked up.

“It feels a little strange, but it is lighter than it looks.”

“Good, is it too snug or tight anywhere?”

“I don’t think so; nothing feels like it is pinching.”

“Great, I liked the idea as soon as I saw it. As long as you wear this panty-guard’you should be able to sport any style of tiny panty you desire. It also will keep you from poking out if you get erect and ruining the appearance of your uniform or dresses. Now that we have that settled, I want you to go make me some lunch. A sandwich will be fine for me and I think there is enough lettuce for a small salad for you.  Then you can begin your house chores. I put together a daily schedule for you and it is on the refrigerator. Of course you’ll have to play catch up at first to make up for the time you were off, but if you work a little later each day you should be okay. I’ll help you by not requiring dinner tonight. I have a previous engagement planned and will be out late. Do you have any questions for me?”

‘I understand everything but you didn’t give me a key for my panty-guard. I’d like to keep one in my room.”

“Oh Nancy, you can be so funny sometimes. I don’t think you need a key yet. I want you to wear it for a while to get fully used to it. You should be able to go to the bathroom or bathe with it on, and there isn’t any other reason to remove it, is there. I mean unless you want to masturbate. Do you want to play with your little wienie?”

I blushed furiously as she spoke. We both knew that I occasionally masturbated, especially when I would dress up, but neither of us had spoken about it. It was embarrassing to admit to her that I wanted a key for that, but my wanting a key was more about control than sex. We both understood that with me locked up and without a key, she would have ultimate control of our relationship. Despite her referring to it as a panty-guard, it was a chastity device. I didn’t really want to agree to let her keep the keys, but the way she presented it I had no choice. I shook my head no to indicate that the discussion was over.

“Well that’s more like it Nancy. That reminds me I did speak with a couple of ladies that employ professional maid services about how they address their domestics and how the help addresses them. Based on their experiences I think I will continue to just call you by your first name, but I want you to address me as Miss Clarisse when you are in uniform. I think a bit of formality is justified, but didn’t like being call Madam or Ma’am. Both seem suited for older women and I like to think we are still younger.  So please try to use that bit of formality from now on, okay.”

She smiled and waved me away. Dismissed, I went down to prepare lunch and look at her schedule. Clarisse had escalated my role as servant much more than I ever expected. Her requirement about how I address her and the uniform were statements about how she saw our relative positions in the household. She had me busy from 7 AM through dinner and clean up to 8 PM. Some of the chores seemed excessive, like buffing the silver ware every Thursday and polishing all of her shoes once a week. To some extent it looked like Clarisse was just trying to keep me busy all the time. She had a note that she wanted me to change her bed linens daily, and replace them with freshly ironed ones. I could tell that would take a while and again it seemed excessive. I served her lunch and she complimented me on remembering proper etiquette as I served her. I spent the rest of the afternoon cleaning the kitchen and doing dishes, she had left quite a mess while I was gone.  About 6:30 she came down, dressed sexily in a short black silk dress with high heels. I saw again why I found her as attractive as she looked very sexy.

“Nancy, I want you to enjoy being back at home. So don’t work too late; you will have time this week to get everything back on track. Tomorrow just dress in your usual skirt and top, with appropriate lingerie, but only put on some lipstick. I’ll want you to change and run some errands later in the day.”

I worked until 8 and decide to get undressed before I ate as I still felt constrained by my new corset. After taking off my clothes, I looked for some of my old male t-shirts and pants to change in to but there were no male clothes in my new room. Slipping on one of my baby dolls, a peignoir, and some high heel slippers, I went upstairs to the master bedroom to look for my old clothes, again without success. I ate a light supper and being tired I went to bed, although still bothered by not finding any of my male clothing, including the ones I had just brought back from my trip nor were there any shoes that didn’t have high heels. I woke up early, not even needing my alarm as I had gotten started early each day on my trip. I dressed as Clarisse had indicated and started more chores. She came down as usual at 9 and I served her breakfast. As she ate she explained what errands were to be done that day.

“Nancy I had planned on you just picking up some groceries and selecting your uniform colors today, but I was able to get you an appointment with Sherry, my stylist. She will see you at 11. That will give you an hour or so to go to the stores to finalize your outfits before you see her. I bought the dresses at Uniform Plus on Collier Avenue. They had a standard uniform that could be customized, so I added the lace trim and shortened it. They have a wide array of pastel colors you can pick for your everyday uniform. I have also ordered a more formal style dress in black, so you can have a traditional maid dress too. After you select your colors, the saleslady will give you a swatch of each color that you can take to Bridal Lace Expressions on State Street. They have corsets, panties, and shoes that can be dyed to match your uniform colors. They also have a selection of lace top stockings that can complete the outfit, although I suggest you stick with basic colors, as they don’t have pastels. Sherry’s shop is on West End Road, about 2 miles from the bridal boutique. I told her how I want your hair done and her staff will also do your nails and makeup.  You can then swing by the grocery before coming home.”

Her description of my errands seemed daunting, as I could see being pretty embarrassed, but my main concern was what I would wear. I didn’t want to go anywhere in my female clothes, but did not know where she had put my regular clothes.

“Miss Clarisse, I couldn’t find my regular clothes last night. Where did you put my pants and shirts? I’ll need to change to run my errands.”

“You mean Nathan’s clothes? I didn’t feel you needed them anymore so I gave them to charity. I do have a woman’s pantsuit and some flats you can wear for your errands. I’ll put them out on my bed after I get dressed. I thought it would be a good compromise, as you certainly wouldn’t want to leave Sherry’s shop all made up and wearing a man’s clothes. This way you’ll look appropriate before and after. Just wear your panties, padded girdle and a matching bra without forms; I still want you to be properly dressed, even when running errands.”

I nodded my head as if I understood her logic, but was quite disturbed to hear that she had taken my male clothes. I didn’t want to spend all my time as a woman. I liked doing it, but I still wanted to go out and see my friends, play golf, or visit our Club. I decided that I would talk with Clarisse after I ran my errands today. We would need to set more realistic guidelines for my household duties.  Once I had finished cleaning up from breakfast I went upstairs to change. The suit was on the bed. Thankfully it was a sedate brown color with a beige pinstripe. The pants had a high waistline and zipped up the back, while the jacket was short extending only to the waist, with a single button. She had included a beige sleeveless mock turtleneck top and the shoes were a tasseled loafer, thankfully without heels. Once I had everything on, I looked at myself in the mirror. I presented a rather androgynous look, with a masculine face and slightly feminine clothes. I decided it was better than any alternative I could come up with. Clarisse had also gotten me a small handbag that matched the outfit. When I suggested it might not be necessary, she pointed out that the pants lacked rear pockets and I would need to carry the swatches from one store to another. Again I was not pleased but not sure what else to do, I put my wallet in the purse and left to do my errands.

I was able to find the uniform shop rather easily, once I mentioned Clarisse, the clerk recognized the sale and asked me about the fit and how I liked the uniform. Blushingly I replied to her questions, adding only that the rest of the skirts needed to be hemmed an inch shorter. She smiled and wrote down the change mentioning that she and Clarisse had discussed that when she made her first purchase.  However, to get the same flare to the skirt, I would need a bit of a petticoat with the shorter length, and would only increase the cost slightly. The underskirts wouldn’t be overly noticeable, mostly providing just more volume, They would be attached to the skirt, in a neutral white, but the lace at the hem also sported a satin ribbon that matched the other items in the outfit; thus if the underskirt did show when I bent over or turned too fast, it would be attractive. The uniform color choices included several pastels as well as darker shades such as navy, forest green and brown. The clerk showed me the pastels, indicating that Clarisse had specified that the remaining uniforms were to be light in color.  Given no choice to pick more conservative colors, I selected a pale lemon yellow, baby blue, mint green, peach, and light pink.  The clerk told me the uniforms would take about 2 weeks to be made to our specifications and gave me color swatches to use for the matching items. Although I was a bit embarrassed, the lady was nice and did not act as if it was unusual for a wife to buy maid uniforms for her husband. I left and went straight to the bridal shop.  Unlike the first store, this shop was quite busy and it took a few minutes until a young lady was free to wait on me. I mentioned the order Clarisse had made and when she looked it up, she could hardly contain a giggle. She asked if I had color swatches and then proceeded to record the rest of the order. I told her that we wanted the same style corset and panty, and choose lace top stockings, in white, black, dark brown and tan, getting several of each.  She had a choice of shoe styles and I decided on strappy sandals in yellow and green, pumps in blue and pointed-toe sling backs in peach and pink.  The entire time the clerk sniggered and made little comments about how nice each item would look, what a feminine color that was or how sexy something was.  I was about as embarrassed as I had ever been. Similar to the uniform order, she said it would be about 2 weeks for them to arrive.

I was running a bit late so I hurried to the stylist, almost forgetting that I was going to a public place to become more feminine looking. Entering the salon, I was greeted by the receptionist and soon was talking with Sherry. She looked at my hair, running her fingers through it as she talked about my new style. She said that Clarisse’s preference would be a good style for me, but she wanted to adjust my hair color to cover the gray and add some highlights. Not knowing what else to do, I just agreed with her suggestions. She went right to work wrapping me in a leopard print cape and applying the color crème to my entire head. She then sectioned smaller portions of hair to apply a stronger bleach to add highlights. Each section was wrapped in foil until she felt enough areas had been done. I spent about 20 minutes under a drier. Removing the foil pieces she shampooed and rinsed my hair and then began to cut it. She wasn’t really removing much length, but mostly shaping and layering the hair. Once she was finished she put my hair in rollers added a hair net and sent me to see the nail technician.

She was a bubbly little woman who chatted on as if she had known me for years. She started right in with a pedicure and then smoothly switched to applying short gel nails to my fingers. It was apparent that Clarisse had outlined what she wanted as well and soon I had nice oval shaped nails in a matching shade of coral on my toes and fingers. I could see how much more feminine my hands looked and couldn’t imagine how I would run errands or do anything without appearing as a woman. The lady then showed me where to go to get my makeup done.

I didn’t quite understand why Clarisse had this service scheduled, but it was obvious that the salon staff had their orders and what I felt was needed was not a consideration. The esthetician looked at my face in a scrutinizing manner very similar to what Sherry had done when looking at my hair. She smiled at me but didn’t really engage in conversation. Finally she just bluntly told me that I needed some shaping of my brows and false eyelashes to make my eyes more feminine and noticeable. She efficiently went to work, waxing my brows first and then applying makeup. She did not rush through the work, but took her time as she would step back to look at my overall facial appearance. I could see nothing at this point, but could tell that my lashes were much thicker and longer. She had described how to attach the false lashes and told me some tips about other make-up as she applied the foundation, blush, eye shadow and lipstick.  The colors were slightly richer than I had been using with the lipstick matching my nail polish.  Sherry came by just as she finished and I went to her chair so she could take out the curlers and style my hair.

Once she was done, she spun the chair so I faced the mirror and I could see the results.  My hair style had gone from a side part with my longer hair pulled back to a style with short bangs, and the long hair combed up and back and then curled under at my neck. The length was less than before but the style was totally feminine especially with my new color and highlights.  The makeup supported the feminine appearance, as my brows were now much thinner and arched outward. The false eyelashes gave me a more sultry appearance and the esthetician was certainly skilled at her job. My face looked much more like a woman’s than I would have ever thought possible. I loved how I looked but couldn’t keep but thinking that this was a much further step into appearing female full time than I had ever considered.  Just as I was getting ready to go, Sherry brought me a small tote bag and told me that Clarisse had left this for me.

I opened the bag and read a short note in it. She expected me to change into the clothes in the bag and then call her. I reluctantly went to the bathroom to look at what she had put in the bag.  Taking out the items, I could see that Clarisse had put a skirt that matched the jacket, some dark brown hose, matching brown peep-toe pumps, dangly earrings, and a pair of breast forms. I slid off my pants, attached the hose to the garters on my girdle and then stepped into the skirt. It fell about mid-thigh, just below the top of the stockings.  The pumps had 4 inch heels and showed off my polished toes. Taking off the jacket and lifting up my top, I inserted the forms into my bra cups. The forms had large nipples that projected through the sheer bra. I smoothed out the mock neck and put the jacket back on.  The earrings completed the look, hanging down below my new hairdo. I could see in the sink mirror that I now looked totally like a woman and although I was a little miffed at Clarisse for surprising me like this, I had to admit that it made passing much easier than without the clothes changes. I called her after I thanked Sherry and her staff and headed to my car.

“Hello Nancy, I assume you just finished at Sherry’s salon. I’m sure you look darling; I know she does great work. How do you like it?”

“Your right, they do wonderful work. I think I look much more feminine now than before. I just wish you had told me what they had planned. With my new nails, arched brows, and hair color, it will be hard to appear masculine now without a lot of effort.”

“Well that won’t be something to worry about for a while. I think you need total immersion as a woman so that you can truly appreciate it. I do have another surprise for you before you go to the grocery. You are just up the road from the Department of Motor Vehicles. I want you to go there and ask for Margaret. She is an old friend of mine and I’ve asked her to help you out.  She knows what to do, just follow her instructions. See you in a while.”

“I don’t know about that. The DMV is not a place I want to go while dressed; I mean I’m not even sure it is legal for me to be dressed this way. I would rather not unless it was absolutely necessary.”

“Well you most certainly will go. Margaret is expecting you and I’ve gone to a lot of trouble to arrange this. Just use that low, soft, breathy voice you’ve been practicing at home. If you look as nice as I expect you do, there will be no problems.  I don’t want to be disappointed today Nancy.”

With that she hung up. I was really nervous about this, but didn’t feel like I had a choice; it reminded me of being on a roller coaster. Once you start the ride you can’t change anything until it was over. I found the building and went to the main desk to ask for Margaret. The receptionist showed me her line and I took a number. Luckily it wasn’t too crowded and after about 30 nervous minutes, she called my number. Margaret was a fairly typical looking woman with brown hair, neatly styled, a pretty face, lightly made up and wearing casual business pants and blouse. I went up to her, cleared my throat and tried to think what to say. I decided just to introduce myself, since I wasn’t sure what Clarisse had planned.

“Hello, I’m Clarisse Booth’s husband. She told me she had spoken with you about me coming by today?”

“Oh yes, Clarisse did talk with me. But I would have never guessed you were her spouse. You are so attractive and seem so feminine. I guess I was expecting someone more mannish and rough around the edges. Well just let me see your driver’s license and we can get started.”

I looked in my purse and gave her my card. She took it, typed in some numbers into her computer and after a short wait began to work on the file on the screen. She seemed to mostly know the answers, but at one point did ask me about my weight. My license had my old weight of 170 pounds, but she said I looked much trimmer than that and smiled at me when I told her my weight was now just 145. After about 5 minutes, she looked back up at me.

“I think I have all the changes, just sign with your new name and we can take your photo. I’d suggest you take off your blazer, it will give you a nicer photo without it”

She indicated an electronic signature pad and after a brief hesitation I signed Nancy Booth, using the name I thought she must be referring to. After she looked at my signature she stood up and I reached for my old license that was in her hand. But she did not look at me; rather she calmly dropped the card into a shredder.  Although a bit stunned at that action, I removed my jacket as she had suggested and followed her into a small room where a camera was set up.  She told me to smile and had me adjust my body slightly, with my arms folded across my stomach under my bust.  She took a couple of photos and finally indicated she liked one and punched a couple of buttons. I could hear a printer first and then a laminator whir until it spit out a card which she handed to me.

“I think it turned out really nice. I usually have a head shot for men, but often for women I zoom out a bit so that more of the body is visible. That was definitely the best choice for you. You should be all set and good luck with your transition.”

With that she smiled and turned to go back to her desk and the next customer. I stood there not quite believing what had happened, just looking at my new license. It indicated that I was Nancy Booth, a female, 5 foot 7 inches, 145 lbs., with blonde hair and blue eyes. The photo was taken so that it showed me from just under my breasts upward. It showed a very attractive female with obviously large breasts, in fact you could even see the nipples protruding through my top. My old identity as Nathan Booth, a man was now shredded and all I had was an official document formalizing me as a female. This was totally unexpected and I was not sure why Clarisse had done this or even what I would have to do to get my real license back.  The only thing I knew was that I needed to leave before something else unexpected happened. I hurriedly put on my jacket, in part to cover my nipples. Even though I knew they were just plastic projections, I felt a little embarrassed by them. They reminded me of what I thought when I saw a woman in similar condition. I was lost in my thoughts as I drove to the grocery. I was lucky that I had a list or I wouldn’t have remembered what I was looking for. This errand was like a blur; I went about my shopping thinking totally of the events at the DMV. I finished as soon as I could and left for home.

By the time I arrived, I was quite mad. I was ready to face Clarisse about the whole situation, which had culminated at the DMV. Ever since I returned from my trip, she had run me toward femininity like an express train. Now it was time to slam on the brakes. I entered the house and put the cold items away and was just ready to look for Clarisse, when she entered the kitchen.

“Oh my goodness, don’t you just look lovely! Sherry has really out done herself; your hair is gorgeous, your nails look perfect, and the way they did your makeup gives you such a feminine face. I’m sure you are absolutely thrilled. I assume everything went well with Margaret? I can’t wait to see your new license. Where is it?”

I was aggravated by her overwhelming endorsement of my new look. For her everything that had occurred to me was just as she wanted. Again this was a far cry from how I saw it. I took a second to keep my cool, I wanted to let her know that I didn’t like what had happened but I needed to object in a logical manner.

“I’m sure you think everything does look darling, but what about how I feel? The changes you orchestrated do make me much more convincing as a woman, but they also limit my choices. How can I appear as a man now? I can’t just undo my hair, hide my nails or fill in my eyebrows at a moment’s notice. They are all overtly feminine. Your changes do make me much more passable as a woman but not passable as a man. What about my driver’s license? It even lists me as a woman now, with an overtly feminine photo. What does that say about me as a man?”

I had to stop at this point as my anger was overcoming my restraint. I glared at her, but she seemed unfazed. She stood there, slowly crossed her arms, and finally broke out in a broad grin.

“Well, well, well, you must fancy yourself more of a woman than I imagined. You already feel like it is your prerogative to change your mind on a whim. You were the one who wanted to express your feminine side; to be able to wear heels, hose and skirts as you wanted; to revel in a woman’s role. You had no reluctance to force the changes in our marriage and in how I saw you as a man. I was forthright with you about the choices you were imposing upon us. If you wanted the freedom to be feminine, then you had to accept the responsibilities. You can’t just pretend that you look like a woman without sacrificing something. I told you if you wanted the role as a feminine housekeeper, then you had to deal with your hair, makeup and body appearances. There was no other option. You must have understood that your feeble initial imitation of a woman was insufficient, because you eagerly accepted my conditions to change. Once you accepted that choice and once you decided you just had to wear heels, then the changes you experienced today were inevitable. You complain about not being able to switch between being a woman and a man. Well that switch is very hard to do; generally to function in day–to-day situations then you must be one or the other. You saw how you looked this morning when you went to start your errands. You were neither masculine nor feminine. That is why you need to take that final step. Of course you would never go there on your own; I had to lead you there. What would have happened if you were in an accident dressed as Nancy when your identification listed you as Nathan? I had to make sure that you were completely in one role or the other. You dreamed of wearing heels, well now your dream is a reality and I’ll be sure you wear them all the time. You made that choice so now you will just have to live with it. Now let me see your new identity.”

I was stunned. Her verbal barrage had totally disabled me. I couldn’t argue with her logic or even complain about how it happened. As she put it, I had dreamed of wearing heels, but had not been strong enough to make that dream a reality. But Clarisse had been strong enough and it was plain after that exchange that my protests of the changes were over. I handed her my driver’s license. She was happy with how it turned out, commenting that Margaret had done a nice job highlighting my new feminine appearance, especially my full bust. She handed it back to me and told me I needed to get back to my housewife duties. I spent the rest of the day, and then the next week or so, meekly doing my chores, doing as she told me, and trying to keep my feminine appearance to her high standards. Any thoughts I had of only being a part time domestic or an occasional woman, a return to my dressing as a recreational hobby were over for now. She emphasized this conversion by having me sign some papers to add Nancy to our bank accounts. She argued that these had to match my new identification and even set up a debit card with my new name, so my purchases could be easier. This period cemented my place in our relationship, with her firmly in the role as head of the household and me as merely her supporter.

Although I was becoming adjusted to being feminine full time, I was not adjusting to my forced chastity. However, any attempt I made to obtain a release was denied; Clarisse simply said I had not yet earned one; that she would consider it once I had been fully attired as a maid should. This added pressure to me to please her and made the notifications that my uniforms, lingerie, and accessories were ready more relief than embarrassment. Clarisse had me schedule a second visit to Sherry’s salon for nail work when I went to retrieve my new work attire. Both sales ladies notice my increased feminine appearance, with the younger one smirking again as I retrieved my lingerie and shoes. The completion of my work uniforms filled in my closet.  It also provided more demarcation of my role, because she insisted that when I was through working each day that I change into my relaxing clothes. These of course still require foundations, hose, heels and skirts, basically the clothes I had worn before as my uniform. Only in bed was I allowed to go without heels. Clarisse seemed much happier with my work once I was properly attired. She even made the comment that I was becoming much more efficient. I saw this as perhaps my last chance to make my maid service a part time affair, and told her I honestly thought I could do all the chores for the house in just two days a week. She contemplated this and replied that perhaps she could get by with just two days a week. Although nothing was finalized I had hope again that I could return to a life that was split between being a man and a woman.

So I took little notice when she told me that she wanted me in my peach uniform the next day and what to make for lunch. She often told me what outfit to wear, especially if she was going to be out late the night before, as in this case. She had to go get her hair done and then attend a charity planning event the next morning and I was to have lunch ready at 2, including setting up a nice table for two in the sunroom. Again this was not too unusual, since we would eat together about 1 out of every 3 meals. She used this time to review my work, talk about fashion or gossip about the latest celebrity news. I saw it as her reinforcing my female desires. I had the table ready, the rice pilaf and salad were done. All that was left was to pour her a glass of white wine, while I seared the fish. With her tutelage, I had become very skilled at cooking and could coordinate the timing of meals so that everything was ready for her quickly, but still fresh and hot. I heard her car come up the driveway so I opened the wine to be ready to serve her a glass to start with, while I cooked the fish. I had just put two glasses on a tray with the wine bottle so I could take it to the sunroom when she entered the kitchen. Although she said nothing, I sensed something amiss and turned around. I almost fainted; she was accompanied by her best friend Sharon. Both ladies had broad smiles and seemed to be enjoying the shock on my face.

“Hello Nancy, I trust you have lunch about ready and have followed my instructions? I took the liberty of inviting Sharon for lunch since we were at the charity planner together. She’s heard me rave about what a good cook you’ve become and how you have mastered the skills of keeping a house neat and tidy, and wanted to see for herself. Didn’t you Sharon?”

“I most certainly did. You know I’ve been quite envious of how you have rid yourself of the loathsome household chores to allow yourself more free time. But you never told me how darling your little maid has become. Nancy you look absolutely precious in that lovely uniform. I must say it fits you very nicely and peach is a lovely color for you. Did you pick it out just for me? It is one of my favorite colors.”

I swallowed and hesitated a second, trying to catch my breath. They had breezed in and Sharon seemed to just be completely at ease with my new appearance. But, I realized that she had asked me a question and decided that I should respond in a way that would make Clarisse happy.

“No, Miss Sharon, the color was suggested to me by Miss Clarisse. Thank you for saying it suits me, as I like to appear as nice as possible. Would you ladies care for a drink? It will be just be a few minutes for me to finalize lunch.”

They both agreed and went to the sunroom while I followed. After pouring them each a glass, I retreated to the kitchen and began to cook. The whole time my brain was spinning. I was trying to understand why Clarisse would out my new appearance to her friend and what the ramifications were of this development. The fish was done way too quickly for me to figure out the answers so I just took out the meal to the women. I served them using the techniques that Clarisse had taught me and once they began to eat, I stepped back. I would be there to re-fresh the drinks or meet any other need, but would not be part of the conversation.  While they ate they talked only of their morning meeting, options for the event and then some gossipy news about some of their friends.  I had expected Sharon to be focused on my appearance and to pepper Clarisse with questions, but quite the contrary she seemed to act as if I had always been this way. But as I began to clear the dishes and they got up to go out on the deck, I overhead snippets of conversation, I took to be about me.

“…does all the cleaning with an eye to detail….;

….became very skilled at ironing and laundry…;

…excellent at meals, both cooking and serving….;

…oh yes, a variety of uniforms, all with matching shoes, lingerie and accessories…;

…is respectful and follows orders promptly….”

Although these all sounded so positive, it did embarrass me to know that Clarisse was describing my feminine skills to one of her friends, much as she would have any good maid. Sharon’s comments were even more embarrassing.

“…seems quite at ease in heels, as if he has worn them forever…;

…his figure is almost striking, such a narrow waist and large bust…;

…his hair and makeup appear quite natural, feminine but not too much….;

…so he just allowed you to put it on, lock him up, without a protest….

…not once since you kept the key, that sounds like he is really docile….”

Despite my overwhelming embarrassment, after I finished clearing the table, I knew it would be best to check with Clarisse to see if they need anything else

“Why yes, Nancy, you can do one more thing. Sharon wants to see the rest of your uniforms. Go ahead and show her your cute little maid’s quarters and all of your attire.”

“I definitely want to check out the colors, please show me.”

With that I took her down the hall to my area. She seemed extremely interested in how everything matched and made me show her each corset, panty, and shoes. It seemed strange to be chatting with Clarisse’s best friend about how the corsets felt and what I liked about different shoe styles. Finally we headed back to Clarisse.

“Her outfits are so precious; I mean how everything is color coordinated, even down to the tiny panty. It definitely escalates her appearance as a maid, so much more professional.”

“So, I take it you are interested?  I think if Nancy comes over for two days the first week, she can get everything on track. Then one day a week should keep your place looking good.”

“That sounds great. I’ve not been happy with any of the services I’ve hired. I can tell from how she keeps everything so nice here that it will be a big improvement. Plus none of my other maids looked so sweet.”

With that settled, Clarisse showed Sharon to the door and they chatted a bit about when I might start. After Sharon left, Clarisse returned to me in the kitchen.

“Well Nancy looks like we’ve arrived at a solution to your problem. When you mentioned that you could do all my housework in just two days a week, I checked your daily schedule and had to admit you were right. But what to do with that extra time; I finally hit on an option when I went out the other night. I heard more complaints about poor cleaning services than I would have thought possible. I knew several of my friends used the same groups, so I decided to see if they would be interested in employing you to clean their places. Sharon was my first customer and it looks like it might work. I figure you can do work at three households, one day a week, still have time for two or three days at home, and even have a day off or the ability to handle special events.  Of course, you don’t really need money for daily expenses so I negotiated enough so you can afford your feminine luxuries, like salon treatments, hair styling, extra cosmetics, lingerie, and of course more heels. A girl can never have enough cute shoes. What do you think?”

“I will be working for other friends?  I hadn’t even considered that. I was thinking of just having some free time, perhaps without dressing up.  I mean I guess I can help Sharon out, since she already knows, but I’m not sure I want others to know about this. Can’t we just keep it to us three?”

“Oh Nancy, you silly girl, sometimes you sound like your feminine appearance is just a new found hobby. You’ve been fully feminized for several months now, even running errands about town in dresses and heels. You think no one else is aware? Anyway, I’ve already approached the two other potential customers and I have the impression that they are as excited about the possibility as Sharon was. I don’t really see any chance they won’t at least try you for a few weeks.”

“Who else knows? I mean who did you talk to?”

“Well I have both of them lined up this week to come over for lunch. I liked the idea of them seeing firsthand how obedient you are when serving and what a good cook you are. Also they can see from our house what high standards you meet for cleaning. On Wednesday, I have Jacqueline Reston scheduled. I remembered from your time at the office how she complained about the chores keeping a house neat after she made vice-president at your firm. I had a feeling she’d love the chance to employ you as her personal maid. The other customer is our dear friends from the Club, Teresa and Jim Ellington.  I always got along so well with her and Jim seemed to relate to you. I mean she and I played doubles tennis for years and you guys loved to golf together. I knew they spent so much time at the Club, that they needed good, efficient domestic help.”

I almost fainted. Jacqueline was a subordinate when I was a VP and as she worked her way up management ladder, I was about the only one in management who didn’t think much of her. Of course she would love the idea of me as her maid, talk about payback. The worse thing of course, would be that she could destroy my reputation around the office if she wanted. I wasn’t sure I could get her to keep my new situation private. As for the Ellington’s, they are one of my favorite couples at the Club. I mean Teresa is very attractive, likes to wear sexy clothes, flirts, and has a penchant to drink a little too much. Jim is friendly, engaging, but very competitive on and off the course and seems to enjoy getting one up on you. I could see them being very hard to work for and again it would be difficult to keep them for telling our other friends at the Club. Overall, Clarisse couldn’t have found two worse case options for my household clients.  I resigned myself to dealing with this and thinking of how to reduce the impacts on my life.

Clarisse had scheduled Jacqueline for the day after tomorrow, so she had me go over the house with a fine tooth comb, making sure everything was dust free and sparkling. I worked up a rich beef stew with homemade bread and had it all ready when she arrived. Clarisse had me answer the door and bring her back to the living room where she was waiting. I felt like I would rather be dead. Clarisse had insisted I wear the bright yellow uniform and I felt like a canary in front of a hungry cat. When we got to the room, Clarisse stood up to welcome our guest.

“Jacqueline, I’m so glad you could make it today, I know it can be difficult to get away from work during the middle of the day. We’ll try to make this quick, but enjoyable.”

“Well I’m happy to be here and seeing what you’ve done with Nathan has already made it very enjoyable.”

Turning to me they both smiled. Clarisse indicated that I should begin serving lunch and I left for the kitchen. They went to the dining room and sat down where they resumed the conversation.

“I’m not sure I would have recognized Nathan if he wasn’t at your house. When you mentioned that he was doing domestic household work and would I be interested I had something else in mind. You’ve done a wonderful job making him look feminine, especially in that uniform. Was this all Nathan’s idea?”

“He proposed being my maid and transitioning to a female persona, but he was so efficient on the job that it was I that thought of having him work for some of our friends. Oh he goes by Nancy now days; it seems to fit his appearance and role in life much better now.”

I returned and began serving the meal. Once again after serving, I stepped back to be ready if they needed anything but did not intrude into the conversation.  Clarisse explained that I would be willing to work 1 day a week for her, that I would be in uniform and that the minimal pay would be used to help maintain my feminine appearance. Jacqueline was impressed that I did all the household chores and complimented me on the meal.  She asked Clarisse a couple of questions about my uniform and in general about how long I remained dressed as a woman. She seemed quite surprised when Clarisse told her that I was dressing fulltime, and Jacqueline also liked how I addressed my wife as Miss Clarisse. After lunch, I took her for a quick tour of the house and my quarters, showing her the rest of the uniforms.  Finally we got back to Clarisse. The women talked while I went to the kitchen to clean up.

“Well Jacqueline, are you interested in having Nancy become a domestic helper for you? I think you’ve seen and heard most of her qualifications.”

“To be truthful Clarisse, I’m not sure he would meet all of my needs. I see that he is skilled at the techniques of maintaining a household, but I have a couple of concerns that you would have to agree to first.”

“Well let’s talk about them; they may not be an issue after all.”

“First, because of the small size of my condo I think he could easily clean it in half a day, even including laundry. I would greatly appreciate that, but I have another area that needs cleaning just as much. When Nathan left the firm I moved into the large corner office that he had occupied. It is a lovely space and I spend almost as much time there as at my home, so I’ve accessorized and worked with an interior designer to make it more appealing. But it is full of built-in wooden shelving with lots of ornate detail work, which I have used to display books, awards, pictures, and a wide variety of decorations.  Our service doesn’t really clean these very well; the items need a regular dusting and the wood is in terrible need of a deep polishing. I think it would be something that would take several days to do properly. If Nancy were to work for me, then I would want her to work a half day at my condo and then a half day at my office.”

“Oh Jacqueline that would not be a problem; how you use Nancy’s time when she works for you is up to you.”

“Well the second issue is a bit harder to solve. When Nathan and I worked together, he never showed me the respect I deserved, even when I became more senior in management. He dismissed my ideas off hand, and even belittled some of my proposals. I know he obeys you seemingly with little protest, but I have my doubts whether he would do so for me when it is just the two of us. I mean I don’t have any control over him, like you can wield, and without being able to apply some form of discipline then I think I would still be facing resistance from him. ”

“Um, I see your concern. You’re right that I have control over him; the fact that he is locked up and I have the key to release his cock does give me more power than you would have. But I expect him to obey you as he would me. Perhaps a little demonstration of what I expect from him and what you in turn are permitted to do, will resolve that.”

Clarisse called me in to see them.

“Yes Miss Clarisse, what do you need?”

“Nancy, Jacqueline has a concern about your service to her. In the past, you have not shown her proper respect. Since you are to work directly under her now, I want to be sure that you know she is your superior in every way. So, I want you to go right now to the library, remove your dress and wait for us. Is that clear?”

“Yes Miss Clarisse.”

I hurried to the library, more than a bit apprehensive. I quickly removed my apron, unzipped the dress and soon was standing just in my corset, panty, stockings, and heels. I was quite puzzled about why seeing me in my lingerie would make me respect Jacqueline more. The women walked in a few minutes later.

“Very good Nancy, now please turn around, face the desk, lean across it, and rest your weight on your forearms.”

I did as instructed, with Clarisse telling me to stretch out a bit further after my first attempt at positioning myself as she had asked. This left me with the upper half of my body parallel to the ground, up a little on my tiptoes, with my bottom right at the edge of the desk. Clarisse then walked behind me and lightly began to rub my ass cheeks. I blushed almost immediately, as Jacqueline was smirking as she watched. Suddenly I felt a quick slap and then another to my bottom. Neither blow was particularly hard, so pain was minor, but they were quite unexpected.

“Nancy, if you fail to meet Jacqueline’s standards or your behavior is disrespectful, then she has my full permission to discipline you in the manner she sees fit. Why don’t you demonstrate your intent, Jacqueline?”

The women then changed places so that Clarisse was in front of me and Jacqueline behind. I felt her put her left hand on my lower back, right above my ass cheeks, but she did not spank me immediately.

“Nathan, I will demand a bit more demonstration of respect when you are working for me. I expect you to address me as Miss Reston at all times. You will curtsey when you speak to me or after I give you an order. I prefer you look downward as you work, unless I am speaking directly to you.  When you have a question or information for me, you are to come to me, stand quietly before me, and wait until I give you permission to speak. You are never to interrupt or talk over me. Now, let’s proceed to your discipline. First, raise your butt a bit more; up on your tippy toes will help.”

As I lifted my heels so that my bottom elevated a little more, Jacqueline pushed down on my lower back. This effectively positioned my butt cheeks at a more upward angle. Apparently pleased, she then began to spank me. She gave my right cheek five good hard blows, quite harder than Clarisse had done, and then switched to the left. After it had received five, she repeated the whole sequence so that I received a total of 20 spankings from her. Even though each blow was not extremely painful, the cumulative result was. My bottom now burned and each cheek glowed bright red contrasting with my light skin. I desperately wanted to rub it and do something to soothe it.  Satisfied, Jacqueline stepped back around so that she was with Clarisse facing me. I held my position, but couldn’t really look at the women, as this was the most humiliating experience I had been through yet. Finally Jacqueline spoke.

“That will be your typical punishment for an offense Nathan, but they can be more severe if your deportment requires it. Now go stand in the corner and think about how you can be a better domestic and how you want to improve your attitude towards me. When you have demonstrated that you are fully accepting of my position as your employer, and your position as my servant, then I will address you with your new name. Until then you will be Nathan with me; I don’t believe you have quite earned the right to a woman’s name yet. And please don’t rub or touch your ass, I don’t really want to see you caressing yourself in that manner.”

I did as she told me to, although it was a hard not to try to rub away some of the pain. Facing the corner, I could feel my face flush again, as I knew I presented a picture of a totally submissive. The ladies left for a few minutes, as Jacqueline went to the dining room to retrieve her purse. Finally they returned, talking about schedules, and timing as they entered the room.

“Nathan, I need to go, so I want you to help me. Take my purse out to my car and use the key to unlock it. You can wait there till I arrive so you can open the door for me.”

“Yes, Miss Reston.”

I bobbed a quick curtsey, took her purse and keys, and then went to put on my dress.

“Nathan, I did not tell you that you could put your uniform back on. Just go as you are and then you can get dressed on your own time, and not waste mine. That is a good example of not listening to my instructions, not respecting me or valuing the importance of my time.”

“Sorry Miss Reston.”

I curtsied again, and then scurried out of the room toward the front door. I could hear Clarisse chuckling in the background and her complimenting Jacqueline for her treatment of me. Clarisse indicated that my service would probably be better for her and all my clients after a while serving Jacqueline.  I was totally petrified as I went outside and did as Jacqueline had requested. I could feel the cool air on my hot butt and I was very aware of how underdressed I was. I stood by the door for what seemed like ages, until the women came out on the porch. They hugged and talked about getting together sometime soon. Finally Jacqueline got in the car. Looking up at me, she smiled.

“I’m really looking forward to this Nathan. I can see that you have a lot of potential as a domestic servant, but you just need more direction. I won’t have the emotional attachment that Clarisse does to you, so I will apply discipline and instruction as much as needed. So be prepared when you come to work for me.”

With that she drove off. I quickly re-entered the house, and got dressed.  Clarisse did not say anything about the lunch, just telling me to get back to my chores. My bottom burned for a good hour, and I did not even try sitting until long after dinner. I was definitely not looking forward to working for Jacqueline, as I knew I would be punished every time, no matter how well I did.

Clarisse had set up my final lunch interview for Saturday, as Jim was committed at work during the week. I again made sure the house was spotless and put together an intriguing meal, a bit more elaborate since it would need to serve three. Lunch had been scheduled a bit later than usual, as Clarisse had a morning appointment but I had everything all prepared and was dressed in my light blue uniform. I was really dreading this event, because I had never been seen dressed as a woman by a man I knew. Admitting to a fellow guy, that I was so feminine inside was a hurdle I wasn’t sure I was ready for. In any case, I prepared everything and was just waiting for Clarisse’s return, as she had not yet arrived back from her meeting. It was only a few minutes from the appointed lunch time, when Clarisse called and explained that she was stuck in traffic and would be late. I was to explain this to our friends and keep them entertained till she arrived.  Just as we finished talking, the doorbell rang and I went to the door and opened it.

“Hello, you must be Clarisse’s new maid. We are here for lunch with the Booth’s.”

“Yes, I know. Miss Clarisse is out and has run into some traffic, so she will be a bit late. Please come in and I’ll show you to the sunroom.”

“Oh, I know the traffic can be horrible here. Just tell Nathan that my wife and I are here.”

I blushed as Jim said this, because it was painfully obvious that Clarisse had not told them of my conversion, nor did they seem to recognize me. I just nodded and lead them down the hall to the sunroom. I asked them if they wanted a drink while they waited, took their orders, and then left for the kitchen. I wasn’t sure what else to do or tell them. Upon my return I handed them their drinks, and was going to say something about more work in the kitchen, when Jim spoke up.

“So where’s Nat, it didn’t sound like he was with Clarisse? Is he upstairs getting ready or what?”

I almost immediately felt my face flush hotly as I began to blush profusely. I swallowed nervously and looked down, trying to think of what to say. Looking back up, I glanced at Teresa and saw her face light up.

“Well I’ll be. Is that you Nathan? It is isn’t it? You look so different; I didn’t recognize you at first. Only when you began to get nervous did your eyes remind me of you.  You look darling! Your outfit is so stylish; it’s very feminine, but obviously functional. I’d say that is your own hair too and not a wig. You always had such nice full hair. I see it works well with a woman’s hair style. I’m impressed too with your makeup, just enough to emphasize your feminine qualities without being slutty. When Clarisse told me you were interested in doing some domestic work at our house, I couldn’t quite figure out why. But now it is crystal clear.”

“Nat, is that really you? I can’t believe it! You had me totally fooled. Ha. I was thinking that you had lined up a nice looking little honey to be your maid and all the time it was you. I guess I never noticed how sexy your legs looked, but then again you never showed them to me in heels. I know you haven’t been at the Club in a while, but I just thought you were tired of me beating you at golf. But this, this is too much. You and Clarisse have to be kidding us right? I mean you can’t dress like this all the time. You really want to be our maid? What the hell happened?”

“Don’t be so dense, Jim, of course it’s for real. He always had a penchant for the feminine side before. I mean he’s never been like your other friends. When I’d wear something really sexy and pretty, I’d see him looking more at the clothes or shoes than me. Now it all makes sense. He was never crude and vulgar like Jake or Steve, but more refined. And his delicate features are perfectly suited for a feminine appearance. As far as being a maid, I’m sure Clarisse can explain.”

Just then, Clarisse walked in the house. She was full of emotion, first an outburst about the stupid drivers in this town and then a friendly welcome to Jim and Teresa. She apologized for being late, but sensed that something else was on their minds. Smiling she glanced at me and then back to the couple.

“I see you have met Nancy, my new maid. I hope she was courteous and respectful to you. She’s trying to be better at placing her guests and employers needs above hers.”

“He most certainly was. Got us drinks and settled us out here right away. I must say you’ve done a wonderful job with his or rather her appearance. We didn’t recognize her at first, between that lovely outfit, well done hair and make-up; it hardly looked like the Nathan we knew. But I must say he is very attractive as a woman.”

“You got that right. I still can’t believe that is my old golfing buddy. Every time I look at him, he just looks more and more like a girl. How far did you take his changes? I’d guess with that cleavage he must have had a boob job.”

“Ha, not yet Jim, everything so far has been just cosmetic. But the key element is that she has embraced being a woman full time. Nancy is very committed to being the best domestic servant she can. That’s why we wanted her to work with you two; she’s become so efficient I couldn’t keep her occupied here. Speaking of that, let’s have lunch so you can see her in action. Nancy, why don’t you bring out the food and we’ll move to the dining room.”

“Yes Miss Clarisse, right away.”

I hurriedly started serving lunch. Everything went smoothly, they seemed to really like my meal and I think I impressed them with how I served and cleaned up the meal. They talked about me and my new situation initially, but then I became more of a background, as the three of them talked about the Club, their recent activities and other topics. Finally, Clarisse suggested I show Teresa my uniforms and new quarters. Surprisingly, Jim wanted to go as well. I showed them the various outfits, including the matching lingerie. Teresa was delighted; complimenting me and Clarisse on how swanky the outfits were. Jim was a bit more surprised.

“Nat, you mean you’re wearing all that under your dress? Isn’t that corset uncomfortable? And those panties, they’re so small they can’t hold your cock can they?  I got to see that to believe it.”

Clarisse smiled, and indicated that I was indeed wearing the entire outfit, including the panty. She suggested I show them. Reluctantly, I untied my apron, unzipped my dress, slipped it off, and for the second time stood before one of future clients in just my underwear. Jim couldn’t help but let out a little wolf whistle and Teresa gushed over how sexy it looked and how it really gave me some curves. But they were both stunned when I pulled down my panty, at Clarisse’s insistence, to show them my chastity tube, or panty guard as she called it.

“Nat, do you have to wear that while you are dressed up? I knew from the locker room that you weren’t that big, but that thing makes you look absolutely tiny.”

“Oh he wears it longer than just when he is dressed. I decided that it would be best if he wore it all the time. He has had it on ever since he started as my maid. I’ve kept the key and we agreed that he would earn release by learning his new role and performing to my expectations. Now that she will be working for others, I’ll take input from them as well.”

“Oh my, that is a lot of discipline on her part. I mean she has to control her urges mentally and can only earn release by focusing on her responsibilities. I can see how that would be an excellent training and motivational approach.”

“Gees, Nat how long has it been? ”

“I guess it is just about two months. I try not to think about it.”

“Ha-ha, well that has to be difficult. But from Clarisse’s description, it sounds like you allowed her to clip your wings willingly, so I guess it does fit with your decision to forgo being a man. I must say your cooking and house cleaning skills are very impressive. I don’t have any problems with you being our maid. The fact that you’re all locked up will make it easier to have you swishing around our house too. I mean I won’t have to worry about you trying something with Teresa or seeing how you love lingerie, doing something you shouldn’t when you wash hers. I only have one question, Clarisse. Does Nancy have to do everything I ask and if I she fails to please me what are the consequences?”

“Oh she most certainly does have to follow your every instruction. Not only must she keep you happy to earn any release, but I have no problem with you implementing your own discipline plan for Nancy. One of her other clients has instituted a discipline plan where failure to please will result in a severe spanking. You can take a similar tack or design whatever you feel works for you. Does that answer your concerns?”

“Most definitely, I may not need it but I want the option. So when can she start?”

The three of them left and continued discussing possible work schedules while I got dressed. After they had agreed on the plan, Jim and Teresa left and I cleaned up. Clarisse informed me of how the schedule would work for the next few weeks. She had set up two days of initial cleaning at Sharon’s and the Ellington’s houses first and one day at Jacqueline’s.  Once I had gone over the work with them and whipped everything in shape for a few weeks, we would have a more regular routine; basically one day a week at each location, with the option for additional duties as needed. They could also train me on how to run errands for them, although Clarisse required that I not be in uniform for those duties. She suggested it be done before I arrive or at the end of a work day. I would get ready, wearing all but the uniform and apron before leaving to work. I could then change into the uniform at their house. She was always working on the details of my service.

The first two weeks were really stressful. It was so intimidating to be under the direction of someone else. Although I had at first worried about working for Sharon, she turned out to be the easiest and nicest of my three clients. She kidded me about my new life, but generally just enjoyed having her house cleaned. She also made sure I fixed her both a lunch and dinner each day. I think being single, she liked the idea of a healthy delicious home-cooked meal for a change. She did spend the most time quizzing me on my new life and in a way we chatted like girlfriends more than I would have ever imagined.

Of course, Jacqueline was not pleased with my work at her condo and I was thoroughly spanked at the end of my shift. I had completely expected that. But, I did dodge a bullet with Ms. Reston; my first work at her office occurred when the rest of the staff was absent. I wasn’t sure if this was intentional or not, but in a way seeing my old office, and more specifically cleaning it to her standards only heightened my anxiety of doing it again when everyone was there. Of course being spanked, spread across my old desk was the low point of it all. She was particularly forceful and afterwards my butt burned and stung for hours, long after my reflection period, standing with my panties down around my knees as I stood facing the corner of her office, was over. She wanted me to fully appreciate how considerate she was in “taking her valuable time to correct my failures”. Her choice of phrasing instantly reminded me of a line I had inserted in her first performance review when I had cruelly listed her (mostly exaggerated) shortcomings during her work for me. I knew that was no accident, and I could see that my first day working at her office when everyone was present would be the most humiliating day of my life.

Overall, however, it all reached a climax as I worked for the Ellington’s. Teresa was flirtier at home than when we were together previously; I spent a good portion of the day with my cock semi-hard in the tube, painfully trying to get erect. Jim also took pleasure in making me work near him when he was in the bath or getting dressed; seemingly flaunting his cock, emphasizing how big he was, the fact that he and Teresa had sex frequently, and that I no longer controlled my own penis. They even did it once while I was there. The only positive was he had not seen fit to punish me yet. Despite how awkward everything was, I was making it through the initial phases. I had the work figured out for all my new clients and was ready to shift to a more routine schedule. Just as I was reaching some level of comfort, I faced my most agonizing event at a special event for the Ellington’s.

Teresa loved to entertain and had decided a small dinner party would be a good way to utilize her new domestic. In the past, I had been to several of these dinners and always had a good time. Now the event filled me with nothing but dread. I spent a whole day cleaning and decorating their house, followed by working most of Friday on the appetizers, main dishes and desserts. I had selected a menu that would allow me to prepare most everything ahead of time and then slow cook them or reheat items before serving. Teresa had made it very clear that she definitely wanted me to serve dinner, as well as welcome each guest to her home.

Of course, Clarisse had insisted on a new uniform and had worked with Teresa to purchase one. She also suggested that I scheduled a visit to Sherry’s salon Saturday before I reported to their house for work. Following her suggestion, I went to the salon, had my regular manicure and pedicure with a subtle French manicure style, got my hair lightened and styled, and had my makeup done, with dark red lips and thick false eyelashes. Clarisse had insisted I use the large breast forms which I had attached to my chest prior to going to the hair salon, so I assumed the uniform would feature a tight bust. When I was finished I went on to the Ellington house, where I did a quick check of the house and started the slow cooking meal. Teresa had made a little change room for me in their spare bedroom, and after getting everything ready for the party, I retreated to it in order to change into my party uniform.

My whole outfit reflected the black and white color pattern of a traditional maid’s uniform. The under-bust corset was a matte black with a sheer white lace overlay. Its four garters were black with white lace down the edges and a white bow where they attached to the corset and at the end near the clasp. The tiny thong was similar in design with white bows where the small front panel attached to the waist straps and in the back at the point where the rear strap emerged from between my cheeks.  My stockings were sheer black with a wide black and white lace band at the top.  They were matched by the black pumps with a 5-inch heel and a large white bow across the front.

Once I had slipped into my underwear, Teresa entered the room to tighten my corset. I could normally tighten the laces on my own, but she had insisted on helping. She pulled tightly on the laces until my waist was reduced to a mere 24 inches. The new corset was obviously smaller than my normal ones and even after wearing a corset for several months, this one made me revert to taking small breaths, much as I had done when I wore a corset for the first time. After tying off the laces, she encouraged me to hurry up, so I proceeded to slip on my uniform.

It was a halter design with a broad neck band of white lace interwoven with small pearl-like beads and fastened with a set of pearl buttons at the back. The halter top was a thin black silk that fit tightly across my chest, edged in white lace, and was bare in the back just covering the top of my corset. The short skirt flared out at the waist and only went to mid-thigh. It was black with a black lace overlay and around the hem was trimmed in a wide sheer band of white lace. The opaque skirt stopped at the top of my stockings and their lace tops could be seen through the sheer white lace band. The skirt was held outward by several white organza petticoats with a thin black satin hem. The finishing touches were the sheer white half apron that lay across the front of the skirt, a white and black lace hair band, and white lace cuffs with pearl buttons. The uniform looked more like a bedroom costume than anything a real maid would wear, but I knew it fit the look that Teresa wanted for me tonight. Embarrassed as I was by the short reveling skirt, it was the tight halter top that clung suggestively to my large breast forms and their projecting nipples that made me cringe the most. Once I checked my overall appearance in the mirror, I decided to just avoid looking anymore, and just try to make it through the party. As I emerged from the bedroom, Teresa gushed about how cute I looked and reminded me I was to be on my best behavior tonight. Jim’s only comment was a low wolf whistle. Scurrying to the kitchen, I immersed myself in dinner preparations to help take my mind off my situation. However, it wasn’t long before the doorbell rang and I went to welcome the first guest.

I was a little embarrassed but not surprised to see Mr. and Mrs. Helton at the door. I knew he was Jim’s best friend and I often played golf with him. She also was well known at the Club, being a good tennis player and was usually seen with Teresa in the lounge after dinners.  I showed them back to where the Ellington’s were and brought them a quick drink. The second couple showed themselves in, right after ringing the bell and again I wasn’t surprised to see them. Tom Washington was the president of the Club and a very successful doctor. He was outgoing and knew just about everyone in my social circle. However, it was his wife, Elizabeth that worried me the most. She had a well-deserved reputation as the nosiest woman in the Club and always knew the latest gossip. I was certain that my new appearance and station in life would be her primary topic for weeks to come; or at least until she had informed everyone.

But it was the last couple that sent chills up my spine. After the bell rang, I opened the door to see Dirk Benfield; he was the resident ladies’ man at the Club. Tall at 6’4’, well-proportioned due to a stringent work out regime, ruggedly handsome, with thick sliver hair, Dirk projected both confidence and a viral masculinity. He had a reputation has the most endowed man in the Club and it was well deserved; I had seen him in the change room and his cock was very impressive.  His standing with the ladies was also helped by his role as a financial wizard and a source for many of the investment capital deals that took place at the Club. Money was never an issue with him. On his arm, was not one of the many single ladies at the Club, nor one of his financial clients, but my wife, Clarisse. She was wearing a low cut, brightly patterned dress that clung to her curvy frame. Her hair was swept upward in a tight stylish hair do that emphasized her long elegant neck and made her look very sophisticated.  She was beaming, obviously enjoying being with Dirk.  She greeted me politely, saying how good it was to see me. She emphasized my name, and introduced me to Dirk. I didn’t need to look at him to see the gloating confidence he was projecting. There were no doubts in anyone’s mind about how the evening would end between him and my wife. My appearance and new position as a domestic to her and her friends was just icing on the cake.

After they joined the rest, I began to serve dinner. Everything went smoothly and everyone really seemed to enjoy my cooking. I remained busy, but tried to stay as inconspicuous as possible, following the training that Clarisse had given me. Maids were to serve, not to be seen or heard. The fact that she and Teresa had dressed me to catch everyone’s eye went against that rule, but I still had to act it out.  To get through the evening, I tried to focus on each task, respond to requests promptly, but not get distracted by the party conversation. The only time I noticed anything was just a quick exchange between Clarisse, Teresa, and Tom. I could hear him answer them that it certainly looked like my frame could support large implants based on how the current forms looked, but I would need to come by his office to be sure, but a d-cup was possible he thought. My heart skipped a beat at this; I knew Clarisse had taken a fancy to seeing me with a large bust and now wanted to make it a real part of me. I just tried to put this out of my mind and finish the evening. It went well through dinner, but as I cleared the table, the men got up to retreat to Jim’s den for after dinner drinks, cigars, and male conversation. The women followed me into the kitchen where Mrs. Helton pressed Clarisse to let us see how I was locked up. Clarisse smiled and in a matter-of-fact tone told me to show the ladies my panty guard. As I reached up under my skirt to slide down my thong, I could feel my face flush a bright red. I brought it down to just about my knees, and then held the skirt up to let everyone see how my cock was tightly locked into the chastity tube. The room was filled with giggles, and chatter, until finally Elizabeth asked a pointed question.

“Clarisse, I love how you’ve transformed him into Nancy but why? And where’s it going to end?”

“Liz, it was just the right thing to do. He was unhappy as a man in his day to day life. His desire to be more feminine forced him to ask for a change in our lifestyle. It wasn’t necessarily my preference, but I went with it and now I realize it was definitely the right decision. I mean even Dirk could see how well this new role fit her. Never once did she really resist my suggestions to change him into her, and any protests were obviously halfhearted. I mean, what real man would let a woman lock up his cock with nary a complaint. It’s been well over three months since he has even had an erection. As far as where it will end? I want to have Tom do just a few changes to her appearance to make it easier for her to be feminine at all times. A little tweaking of her facial features such as plumper lips, smaller nose, and more prominent cheekbones would be nice and he’s agreed that a large bust would be possible. Nancy took readily to the big breast forms; with real implants she could have much more choices in lingerie, wear low-cut necklines, and even strapless dresses. You should see her new driver’s license photo; she’s got her boobs jutting out like a stripper. I knew then that Nancy would benefit from having real breasts.  But we won’t go any further. I think it is important that she keep a cock, although it will always be under my control. I mean there should be some consequences to her decision to abandon her masculinity. After those adjustments, I expect her to be quite happy with her new domestic responsibilities and will find her place rewarding.

We have gone slowly with integrating her into our old social circle, but once I was convinced we were on the right path I started her down the road to permanency. She’s working for a colleague at her old firm, so her new position will be known there; I expect my family to visit in a few weeks so she will be introduced to them; and I trust that you can discreetly make known her change to our friends at the Club. I assume there has been some gossip about my being with Dirk at dinner functions and playing mixed doubles with him as my partner, so I want to fully integrate Nancy into social activities there on her off days. I know she misses golf, so I was hoping she could join a ladies league. I mean she really enjoyed the game, but never was competitive with the men. Her game would be much better suited with the lighter women hitters. I also would enjoy tennis with her; again her game was never built on strength and power, so she always played like a girl. Once everyone has seen that Nathan is no longer around and met Nancy then they will understand my new relationship with Dirk. So long-term I expect her to be totally happy as a full time woman; I know she will be happy tonight. She has done so well I’ve given her key to Teresa. After Dirk and I have gone home, she can stay here and get the sexual release that she has earned.”

I was stunned beyond belief and just began to go through motions as I returned to cleaning up the dining room and kitchen. The women had all congratulated Clarisse on her actions and Teresa had knowingly patted me on the back. I was excited about the idea of finally releasing my pent up sexual desire, but the situation was so bizarre it was hard to look on that as positive. As the ladies went into the living room, Teresa told me to take a tray into the den to clear their glasses and see if the men needed anything else. I did as she asked, but opening the doors to a room of men, who until tonight had known me as their buddy Nathan was humbling. Their veiled smiles or in Dirk’s case his smirk, made my face flush again. Although they all turned to watch me enter the room, Dirk resumed telling his story, and their eyes focused on him.

“I had it about half way into her and she was squealing, moaning, and said it’s so big; I never felt so full. As I pushed more of my cock into her, she kept saying oh my god, oh my god. Finally, I slammed the last couple of inches in, so that my balls slapped her ass. At that point she was practically coming from just being stretched out so much. She really began to hump me back and kept mumbling, it’s so much more than what Nathan gave me, I can’t believe a cock could be so big, it’s like being with a man for the first time. At that point she just started thrashing around and coming wildly. She’s been hot for my cock ever since then.  It’s nice to have a big cock, but it makes it really easy when her husband is hung like a baby boy.”

With that all the guys roared. I felt my face flush, and had to look down at my feet. I knew my world was gone. Hearing them talk about sports and make sexually explicit comments made me realize I would no longer be a part of that world. My identity was now a female one, so my world would be feminine in just about all aspects. Just as I finishing picking up the glasses and emptying ash trays, Jim came up behind me.  I almost jumped as I felt his hand slide under my dress and cup the curve of my ass. He lightly squeezed it and whispered in my ear.

“I’m glad to hear you are staying tonight and I look forward to helping with your transition to womanhood. I have admired this ass ever since you started working for us, and Clarisse has assured me I will be the first to have it. Teresa wants to see how you do as well, and I imagine that after you please her orally we will let you cum provided your enthusiasm for meeting our sexual needs is as good as you have shown for cleaning our house. We’ve not decided exactly how you get your release but odds are it will be Teresa stroking you while you see how much of my cock you can swallow. Clarisse made it clear that she wants us to fully initiate you into your new feminine sex role, as she wants you to totally abandon any visions of yourself as a man. Dirk also made it clear that she has fallen for big cocks. She said that your desires to wear heels as much as possible must include the ultimate. You’ll realize that wearing sky high heels in a fuck-me pump style is not just a fashion choice. So when I take you she wants to be sure that your ass is lifted up by your heels. Does that sound appropriate?”

I lowered my eyes as my mind reflected back on the past few months to the moment when I told Clarisse that I just had to wear heels. She had a questioning look in her eyes, but agreed. Later she told me there would be consequences to insisting that I be allowed to wear heels as I wanted. I know as a man that when I saw a woman in really sexy heels, say a pair of red fuck-me pumps, I assumed she was advertising how sexy and available she was. Now Jim had seen that in me and I could totally understand. It dawned on me that my life was now totally flipped forever. So knowing there was no going back, I decided to embrace my new role. I had tried to think of myself as still a man, even when I saw how feminine I was and how everything I did now was as a woman. Swallowing my pride, I decided I would go along with these last steps, so I looked over my shoulder at Jim.

“Of course I’ll wear my heels for you.”

With that I straightened up and walked out of the room, wiggling my ass as much as I could as I left. I knew Jim’s eyes were glued to me. As I walked out I felt my d-cup forms bounce on my chest and knew it wouldn’t be long before I would have my own real breasts, probably displayed frequently under a sheer top. I realized I was headed fully into life as a woman, and the loud click, click, click of my heels on the hardwood floor was like a chorus confirming I had no other option that I was destined to be a slut in heels.