Charlene; Heels On The Runway

Charlene; Heels On The Runway

I had just arrived back from lunch and after getting myself a coke from the break room, I made my way to my desk. Right there, in plain sight, was a flyer for a contest coming up in a few weeks for a local charity. Our company always participated in any charitable event that is for a good cause; the flyer that is lying on my desk, the latest that is deemed worthy by our CEO. I scanned the first paragraph, wondering why I had been selected for this event. Celeste, our chief executive officer, always evaluates these events and selects members of her staff to participate. I was about to call her, asking for her reasons that I should be involved, when she walks into my office. I hold up the flyer, pointed to it, and waited for her response.

She sat in front of my desk making herself comfortable. “If you don’t have the proper heels, you need not worry, the company will purchase them for you.” Sometimes she can be so frustrating, especially with regards to our interaction. We get along alright, she initially hired me for this job, then promoted me twice as I became aware of what I was doing within the company. We seemed to work well together, our thought processes very similar.

The main difference between us is her determination to get her way, no matter how many people she has to step on to achieve it. Nothing ruthless, just friendly persistent persuasion until you do as she wishes. You might say she is a master manipulator.

The flyer is for a contest, but high heels are required to participate. The main part of the competition is to be decided on a runway, the contestants walking the runway, as used in fashion shows, flaunting their looks and their ability to strut their stuff in their heels. The rest of the competition is a leisurely stroll along the main street in town, showing off their ability to walk in the footwear. The runway part of the contest is scheduled for one of the university’s auditoriums. Both locations were sure to draw quite a large crowd of spectators.

The winner to receive numerous gift certificates for fashions and female necessities. The entry fee and the sponsor’s fees is their way to raise money for the charity. Why Celeste has sent it to me is the question of the day?

I leaned back in my chair, waiting for the other shoe to drop, with her; there is always something else involved. Instead, she wanted to frustrate me some more. “Before you go shoe shopping for heels, you must read the rules of the contest. No heel below four inches, platforms are not allowed. The heel must be a stiletto of no more than half inch width and must color coordinate with your choice of leggings or skirts.

“I suggest something comfortable, since the contest requires numerous runway walks, and a lengthy stroll through town. Now since you have not had much experience in heels, you might want to practice some, purchase several pair and break them in, finding the pair that is the most comfortable to wear for the event.”

I just sat there and stared at her, if looks could kill, she would be a smoldering mess in that chair. Unfortunately for me, she is immune to such actions. I have tried in the past, usually just ending up super frustrated and doing what she wants anyway.

Finally she smiled. “Alright, I will go with you and help pick out your heels, I am busy, but can find the time to help out a friend.” That damn smile got even bigger, she was starting to crack up, and her lips were quivering, like they do before you break out in laughter. “I do wish I had a camera with me, your expression is priceless, a look to treasure forever.” Her comment making me squirm even more. She managed to control the outright laughter, but giggles were breaking out right and left.

She leaned forward, then got serious, well as serious as she ever got. “It is a good charity, I am on the board of it and have been with them for at least ten years. When the idea came up, we jumped on it, something different, maybe a way to meet our goals without all the begging and pleading we have had to do in the past. Then a few of the board members decided to volunteer a couple of our male staff members to enter the race, knowing that the publicity of a male in a contest with women’s heels would draw a lot of attention to the event. I immediately thought of you, you always attack everything with such enthusiasm, I am sure you would do the same here. There are significant prizes for the winners, although they are geared for the female participant. I am sure you would enjoy the salon appointments for a year though. Think about it, I won’t push the issue, if it scares you too much, I will find someone else in the company. Why don’t we have lunch tomorrow at Tony’s, my treat and we will discuss it.”

I nodded my head and she is gone, my life and day a total disaster from her visit. My secretary came into the office. “I have penciled in the lunch, on tomorrow’s agenda, and after work for a shopping trip to the mall.” She also is giggling at my expense, but at least with her, she doesn’t rub my face in it as much as Celeste.

I had several calls I needed to make, straightening out problems that some overzealous company employee made, then denied ever doing it in the first place. When that had been completed, I managed a few moments to do some thinking, actually some soul searching, trying to figure out if I would dare undertake this endeavor.

My name is Charles Comstock, but most people call me Charlie. I was hired by Celeste shortly after I graduated from college. The whole hiring process very unusual, from the interview, to the job eventually offered to me. None of the questions asked in the interview were pertinent to the job I was supposedly interviewing for. Then two hours later, the job she offered to me was not at all what we had talked about. I accepted, thinking that I could handle the offered job, but left the offices definitely confused and bewildered.

I had a somewhat normal upbringing, did the usual things a young male engages in, but never dated much. The few dates I had were lackluster, the evening was usually boring for both of us, and so nothing ever happened afterwards. I eventually decided to forgo the dating experience and concentrate on my studies. My grades improved considerably, the females in my classes, decided to steer clear of me for some reason, so the temptation never surfaced again. All of these thoughts ran through my mind as I debated whether to dip my feet into the water, on in this case heels.

After several minutes, I called Betty, my secretary, back in and asked her to sit down and answer a few questions for me. She had anticipated this and had a notepad with several things written down on it. “How hard is it to walk in heels, and would I have to practice to be able to enter the contest?”

“Practice is mandatory, especially for the stroll through town. For one thing, you have to break in the shoes; new shoes are very uncomfortable, causing blisters and sore spots. The heel forces different actions from the foot, making your walk decidedly different.”

“Should I volunteer for this or run for the hills?” Betty is very level headed, always way ahead of the curve before the ones running the show had put something together. She smiled, “I think you could gain significant advantage if you handled this right.”

I stopped her there and replied, “I have always trusted you, for your ideas and hunches, so handle this for me, tell me where to show up, and what to do and I will do it. Uncharted territory here, I am not sure if I can survive this, but there might be some advantages for me. I don’t want to think about it, just lead me where you think I should go.”

She warned me that there will be moments where I will be unsure of things, and learning to walk in heels is going to be hard work. I tried to stop the conversation but she wanted to give me an inkling of what she had in mind.

“I picture you in the contest fully dressed as a female, makeup, hair, and the works. The initial attention, enhanced when you continue to train in heels while dressed in female clothes. The speculation as to why you are doing this, running rampant among the press and others. That does not even consider the opinions from your fellow company employees. No input from you as to why, just a continued escalation of clothes and female mannerisms. Lots of name calling, I am sure, will take place, but your picture is almost guaranteed to be on the front cover of any newspaper or magazine. Even what looks like bad publicity leaving doubt in every bodies mind as to exactly why you are doing this?

“Now we come to Celeste. She likes you to start with, maybe more than anybody thinks, several favors had been extended to you when you first came on board, but you quickly put the naysayers in their place and excelled, making it to where you are now. So she sees you take this on and carry it much further than she ever thought of, her company constantly in the spotlight because of your actions and deeds. Then, you place in the upper tier of winners, and bring even more attention to her company. Since she is a board member of the charity, you will have almost guaranteed her a successful campaign by your actions, a treasured and respected member of her staff that she owes the world to. What better PR for you, maybe even another promotion to thank you for all your hard work and sacrifice for her charity and company.

“Incidentally, your portrayal of a female has to be 24/7 until the race is over with; it is just too hard to change from one gender to another every day or two. It will be different, I can guarantee that, but I think you might enjoy parts of it, maybe even grow accustomed to the female lifestyle. The contest is scheduled for three weeks from today, the entries have to be in before close of work tomorrow. I know this is a lot to take in, my off the wall approach maybe too much for you, but you did ask for my opinion.”

I just sat there lost in my thoughts, most of what Betty said made sense, but talk about sticking my head way out there, so if it gets taken off, it could mean total disaster to my career. I would be alone other than Betty and maybe Celeste, I am sure no other employee, especially a male, is going to take a chance in acknowledging me or helping me. If I crash and burn, it is my fault and they would be there saying he brought it on himself.

In a weak moment, I told her to start making plans for my total commitment to the contest, I would think it through overnight one more time, but most likely I will see her plan through to its conclusion. I have not got where I am now by backing down from an obstacle, instead, attacking said obstruction and defeating it. Maybe luck will see me through one more time, at least I can hope and pray it will.

I did leave early from work that night, lots of things to consider and think about. The biggest challenge, to try and convince myself, I actually wanted to do this. I don’t remember the drive home, when I got to the door to my house that is the first thing I remembered since I walked out of my office door. I unlocked the door and made my way inside, leaving my briefcase by the door and slipping out of my shoes. I padded my way in my socks to my bedroom, hanging up my sport coat, and dropping my pants. My white dress shirt is next, then I slipped on a t-shirt and made my way back downstairs. I didn’t feel like cooking, so I just grabbed some chips and dip and made my way to the den. I put on some music, stuffed my face and gravitated to a peaceful place in my mind.

Betty’s ideas seemed to be a center point; they made the most sense, but could I handle what came with them. I kept coming back to why Celeste had picked me in the first place; I didn’t think I had done something to make her want to get back at me, but I couldn’t think of any other logical reason for her to volunteer me. I knew I could refuse, but in this company turning down a request from the CEO is not done and still remain a part of it. I awoke the next morning, most of the chips gone from the bag and stiff from sleeping in the chair. I cleaned up my mess and made my way upstairs. A hot shower woke me up some, and then made my way to the bedroom to find some clean clothes to wear to the office.

The drive in, a repeat of last night, maybe I should pay more attention when I am on the road, but my mind is definitely on the contest and my most likely total immersion in femininity. I came in at the same time as Celeste, her reminding me again of the luncheon date. Nothing more is said as we headed to our separate offices.

Betty is all smiles today, I guess her anticipation as to the possible events today making her happy. I got caught up in my work and left a little early for lunch. I got us a table in the corner of the restaurant, some drinks and then tried to relax some. I still hadn’t made a hard and fast decision yet, hoping some divine intervention might provide a better answer to my quandary. Celeste arrived early too, although she only made it five minutes before our planned meeting time.

The waitress got our orders, Celeste telling them that we needed our selections held for thirty minutes before they were prepared. She stared at me, waiting for me to speak first. I steadfastly refused to make the first comment, still waiting for that intervention. She finally asked, “Have you made a decision?”

I replied, “After careful consideration, I will participate in the contest. Just wanted one of my questions answered in return, and I preferred the truth, not some crap dreamed up to make the event sound like some noble sacrifice.”

She giggled and asked what my question is. “Simple, why did you pick me to participate? I remind you, it has to be a truthful answer?” I can see lots of thoughts running through her mind, but she keeps quiet until she has her thoughts together.

She smiled, “The answer you will probably not appreciate, I think you are cute as a male and I am dying to see you in heels, much less walking in them as you participate in the event. When I first hired you, I had the same opinion of you, for a male you are just the cutest thing, in fact, truth be known, that is probably why I hired you. You have excelled in your work, making me look good, now every male candidate I interview, I check for cuteness. You do not realize how much I have had to restrain myself, all these months, to keep my fantasies under control. When the idea came up, I just knew it was the right thing for you. If nothing else, I will be able to check one thing off my bucket list, a dream I have often, that I actually might see fulfilled.”

“If that is true, Celeste, you might just be in for some surprises, I just hope you have a strong heart. Betty has her own take on this, and I have submitted to her wishes, she is handling my training and participation in the event.”

Celeste gave me the biggest smile, “That is wonderful news, I just might have to have a few words with her. I do hope that I at least, get to help in the selection of your heels, you have to remember, that it was my idea.”

We ate lunch in peace, and before we headed back to work, I did accept her help in picking my heels. We agreed on meeting at the food court at the mall at seven tonight, then pursing the shops until we found the perfect pair of heels for me. I am sure before this is over, I will have more than one pair of perfect heels in my closet. On the way back to the office I kept thinking of my perfect pair of heels, quite ridiculous considering I am a male.

Betty let out a squeal when I told her to sign me up for the contest, she was faxing my application in before I could turn and enter my office. The afternoon dragged on, the only thing keeping my mind off tonight is the amount of work that was deposited on my desk. I stayed busy, only Betty reminding me of what to look for tonight, brought the task to be undertook this evening back to my mind.

She had made me a list of what to look for; the type of heel, the height, the color and the requirement that I tried on everything and walked in them for several minutes before I purchased any pair of heels. She suggested several pair, a low heel about two inches to get the hang of things, then several four inches tall that might be suitable for the event. Also she wanted me to buy a pair of five inch heels, if I found a pair that felt comfortable. After wearing the taller heels for a while, a heel height of only four inches would be easy to handle.

Instead of heading home, I decided to eat out, the one restaurant at the end of the mall having pretty good food at a reasonable price. I managed a seat at one of the windows facing the mall, so that I could watch the females strutting about in their heels. I am surprised at how few women actually wear heels these days, mainly office workers and professional women. As I nibbled on my meal, I watched the various females make their way in heels. I noticed they all had a sway or movement in their backsides, I presume because of wearing heels. The realization that I would soon have that movement too, if I did any good at learning to walk in heels made itself evident. A grin came to my face, picturing my butt swaying back and forth as I maneuver in my heels, performing my normal tasks for the company.

The cuteness remarks from Celeste kept reappearing in my mind. It seemed that her decision to hire me is on that basis alone, not for my ability to do the job. I wonder what that makes me. Every time I thought about it for any length of time, I realized that there is probably more to her attraction to me than just the cuteness. I can picture a female in that position easily, but not a male.

After finishing dinner, what little I did eat, I made my way to the food court. Celeste was waiting, and soon I am being drug off to the first store. I knew I would be the subject of a lots of stares tonight, so I mentally prepared myself to just focus on getting the task done, forgetting about how other people saw my actions. We looked at several stores before she found a couple of pair that interested her. We walked in and she asked the salesperson for the black stiletto in the window with the bow on the vamp.

She looked at Celeste and asked what size. She turned to me and told her they are for me, and he needs to have his feet measured. The lady didn’t bat an eye, had me seated and measured my foot. I was informed that I wore a ten wide in ladies shoes, not the most stocked size but in that particular shoe she had it in stock. She went to the back and returned with several shoe boxes. She helped me remove my socks and then handed me a pair of nylon footies to make it easier to try on the pair of heels.

I slipped the footies on and slid my foot into the heel. The arch of my foot reminded me of the height of the heel. The salesperson suggested that I slide my feet back more underneath me and then try to stand. I managed that and was able to stand without much difficulty. I took a few tentative steps, practicing what Betty had told me about putting my heel down first. I walked to the end of the aisle, then back taking shorter steps. I did it slowly, carefully placing my foot down and then taking the next step in a straight line with my previous step.

I smiled when I got back to the chair, I actually did it, not falling on my face, or tripping once. The lady had brought several other styles in my size, all with the same heel height. As I was strutting, Celeste filled her in on my entering the event coming up later this month. True to her word, the company did buy my heels that night, two pair at this store. Both were pumps one with a four inch heel height and one with a five inch heel height. Both pair of shoes had stiletto heels, the five inch heel almost to a needle point, with a flat quarter inch pad for walking on. They were comfortable, and the shoe fit my foot snugly. With my foot that arched, comfortable is a relative term.

Celeste wanted me to wear them out of the store, but I declined, knowing it would be only be a matter of days till I wore them in public anyhow. Two more stores were assaulted that evening, with a total of three more pairs of heels obtained that fit the requirements.

At the last store, I actually made the choice, a stunning gold heel with two straps for support, one across the lower arch of the foot and one around the ankle. Otherwise, my foot is naked in the shoe, with the heel height of over five and a half inches. When I tried them on in the store, they seemed comfortable, and I loved the look of the shoe. “Are you sure this is a heel that you want, they are gorgeous, but I am not sure you are ready for this type of heel?” That statement muttered by Celeste, a puzzled look on her face.

Now a male that is not excited to be in this contest to start with, who just picked out a gorgeous pair of heels to wear, there has to be something wrong here. I made a note to myself to check with a professional, the first few hours of this ordeal and I am already goo-goo over a pair of heels that I just had to have.

Celeste paid for them gladly, making me promise to go to dinner with her wearing said heels. She even told me she would buy my matching evening gown when I am ready. Since the heels were over five hundred dollars, I can imagine what the gown might cost. I noticed when she bought the heels, she used her personal credit card instead of the company card. So now armed with six pair of heels, we headed to our cars. She is parked not far from where I am at, and I got a gigantic hug from her as we parted. I did notice that several times that evening, she called me cutie, a new nickname for me apparently. The drive home is a little better, I did actually remember the trip home, parked in my garage and hauled my loot inside.

Betty had insisted that I call her, wanting to know what I bought. I had to send her a picture of each snapped on my I-phone, and give her a run down on what was said and where I shopped. No comment when I took a picture of the gold heels, but she did find it interesting that Celeste paid for them with her own money.

She instructed me to wear all of them tonight and pick out the most comfortable pair and bring them in tomorrow to work. That turned out to be the black pump with the five inch heel, so I slid the box in a bag and headed to bed. I was a little jittery, wearing heels at work, maybe a little too much for the second day of this scenario.

When I arrived at the office the next morning, Betty handed me a pair of knee highs, told me to slip them on and then put on my heels. When I had that handled, she came into my office and picked up my male shoes. I asked what she is going to do with them, she simply smiled and responded she is going to lock them up. From this day forward, you only wear heels from the time you get up in the morning until you go to bed at night.

I proceeded with my work, most of it can be done from my desk, so the need to walk around is minimal. When it came time for lunch, Betty showed up and pulled me to my feet. I was hustled out the office door, and to the stairs. I pointed out to her that we had an elevator, but she insisted that I need the practice of negotiating stairs in heels. When we hit the lobby, the noise of my heels attracted quite a bit of attention. The receptionist is quite friendly, thanking me for supporting the charity drive. I stared at Betty, but she dragged me on, telling me that she would fill me in later. We walked the short one block distance to where we normally ate at, this time, I am attracting lots more attention than in the past.

We were seated in the little restaurant right out in the middle of the dining area, making the fact that I am wearing heels quite evident to everyone. Lots of whispering going on, but no outright statements being made. The females the most aware of me wearing heels, in fact that is the first thing they seemed to notice about either of us. Betty is not a beauty queen, but she is quite attractive and well built. Her well-endowed breasts seldom missed by any male, whenever we have been together. This time my heels stole the moment though, some of the looks were peeks, but a few just stared at my footwear, then at my body that did not match the selected shoes.

We ordered from our waitress. “If I am not being too forward, may I ask why you are wearing heels?” Thankfully, Betty filled her in, and that seemed to answer what questions she had of me. She complimented me on my mastery of them and hoped that I win the event. After we finished lunch, the walk back to the office seemed insignificant, I liked the heels and nothing felt unnatural or forced.

When we got back to the building, the receptionist handed me a memo that had just been sent from Celeste. It told everybody of my involvement in the contest and made a requirement of everyone to assist me when possible. Any type of harassment would be dealt with quickly and especially any from a male employee. The memo suggested that a new change in the male dress code could be arranged, making it a requirement for all males to wear heels to stay employed.

As I read it I smiled, then Betty from over my shoulder, said that she is glad that Celeste sent out the memo she had written, this would ensure cooperation from my fellow employees. I turned and looked at her, a new found respect for her ability and planning coming to the front.

You knew that Celeste couldn’t stay out of this, a few moments after we got back from lunch, she entered my office and insisted that I model my heels for her. My attempt to forego the modeling, by stating the fact that she helped me buy them did not work. “That was at the mall and this is here at the office, so get out here so I can see you in your heels.”

I could hear Betty giggling at her desk, but she made no attempt to save me from my fate. I walked around the desk and modeled the heels, Celeste admiring me, then hugging me and leaving the office. She made a comment to Betty, but not loud enough for me to hear it. Betty checked to see how I was doing in my assigned tasks, reminding me that I had an appointment at the salon every week night for the next three weeks. I started to say something but remembered my commitment to do as she says, this is her grand plan for me, and I am just a pawn in her overall plan.

The heels didn’t bother me that much, of course, I was not on my feet much during the day mainly doing things at my desk. The few times that I wandered down to the break room, I had more than several pair of eyes follow me, but no comment voiced to me. I did receive several compliments from the ladies, at my ability to handle the higher heels without much apparent difficulty. Other than my first few steps at the mall that evening, the heels really didn’t cause me much difficulty.

My calves hurt after being in the heels for very long, if I was standing for any length of time my toes made their complaints about being cramped in the pointed toes. Of course, walking from my car to my office, then what little walking I did around the office really couldn’t qualify for spending much time in the heels in an upright position. When at my desk, I often slipped them off, for a few moments of bliss.

At a few minutes before four P.M., Betty came into my office giving me the directions to the salon. Tonight’s appointment only requiring an hour, but later appointments would necessitate more time. She would meet me at the salon later, and then follow me home to organize my practice sessions.

With a hug and a cheek kiss, I was sent on my way, wondering what else I would be subjected to in the next few days. The salon was not hard to find, the opulence though surprising me quite a bit. The name Turnabout Gurl maybe not such a good thing. A very feminine décor, the stylists working there just as eye catching as their surroundings. They were apparently expecting me, and I am hurried off to a treatment room at the back of the salon. Diane introduced herself and had me sit at a table with chairs on both sides of it. Each of my hands is placed in a bowl of liquid to soak, while she prepares her tools and polishes.

From the extensions laying on the table my nails are going to get quite a bit longer. I am not sure what to think about this, realizing Betty has this all planned. But being on the receiving end is way different than talking about it. After soaking, my cuticles are handled, pushed back and any excess removed. Then my nails are filed into neat ovals while she matched an extension to each nail. Then a glue is applied to the nail and to my own fingernail while some pressure is kept on the extension until they bonded.

After completing each hand, it is placed in an UV box for twenty minutes to set the glue. “How long is the glue good for?” That seemed like a logical question to me. I figured that it would hold my extensions for a couple of months maybe not that long considering my lifestyle. “It is permanent until the nail grows out? I am left speechless at that response from Diane, definitely not what I expected the answer to be.

Somehow, Betty left out some of the details that might seem relevant now with long talons extending from each nail. I remembered I had agreed to all of this, she did warn me, but now that some of it is actually taking place it seemed a little more real than when she talked about it. A clear polish is next, according to Diane a base coat so that the color does not bleed through to my new nail. Then three coats of polish, a bright pink in color and very significant on the brightness. Each coat of polish followed up with a time in the UV box guarantying me long lasting nails and polish. Then to finish off the treatment a clear gloss, a top coat, is applied and also treated with the UV. My nails almost had a life of their own, any movement of my hands catching light and attention as I tried to maneuver my hands.

Diane talked to me throughout my manicure, asking questions and finding out a little about me. All of the technicians that would work on me in the upcoming days had talked with Betty, so my future had been planned out in detail, everybody knowing their part except me. After completing my manicure she asked me if I liked the nails, I told her they were very pretty, but since I am not used to pretty yet, final judgment would have to wait a few days. Speaking of the devil, in walked Betty, time to gather me up and head to my training grounds. I did find out that all of this is paid for in advance, I wondered about that, but decided not knowing would be the better approach. I did wonder who had forked over the money for it, Celeste a possibility, but then I didn’t think she was aware of everything Betty had planned.

She followed me to my home, removing a bag of food she had picked up from one of my favorite fast food establishments as she got out of her car. We entered the kitchen and she sat the food down on the bar, while I rounded up some beverages. We ate in silence, Betty often looking at my nails, almost as often, as I was looking at them. They amazed me, such a feminine look that seemed to transform my formerly male hands to quite dainty and feminine. They did cause some problems, causing me to reach an object far faster than expected, the resulting stab of pain quite noticeable.

“Do you want to know more details or do you just want to experience them as they happen?” Betty did have a smirk on her face as she asked that question. I did take time to think that through, but after careful consideration, maybe not knowing what is coming up would make the mental part of this a little easier to handle. I couldn’t worry about something I didn’t know is coming.

She asked to see my male shoes and also the heels that Celeste and I had purchased last night. We adjourned to my closet and she gathered all of my male shoes in a bag and placed them by the front door. I gathered that my selection of what to wear to work had just been severally limited. She approved of the heels that had been purchased picking another pair for me to put on; after I had changed into the new heels, she placed a strap around the heel and my ankle securing the shoe to my foot.

She asked me to get some old pillowcases and showed me how to slip it over the shoe so I would not damage my bedding. Thus adorned in two old pillowcases, she gave me a hug and left for the evening. I attempted to ask Betty if this strap was really necessary, didn’t she trust me to do the right thing. The look I received in return answered that question for me.

I just sat there, my new feelings seeming to take over my body. I am scared a little, but then thought to what had happened today, nothing bad had transpired I was still relatively the same except for the long nails and my heels. I day dreamed a little of future day’s activities, but not being a female I lacked much detail to add to the dream. I walked around the apartment quite a bit, even ventured out to the garbage can taking the residue of the meal that we had shared, sans pillowcases. The female neighbor next door did see me, but nothing is said. I am not sure that is good, but never the less it is postponed until a future day.

Sleeping in heels is quite a feat, but the real challenge is getting my pants off over the heels. It turned out to be possible, but at least an hour is spent in accomplishing the task. I had to assume some different positions to make my heeled feet fit to the confines of my bed but once it is accomplished I managed to fall asleep. It was as I was lying there trying to get to sleep, that I thought that all I had to do to get the pants off was to release the straps and take off the heels, remove the pants then replace the heels and straps. I might be cute, but either didn’t have the brains or lacked the ability to utilize them. The jury is still out on that last statement.

Due to the heels a sponge bath is my only option the next morning, of course something new required lots of time to accomplish, then I wasn’t sure I had reached all areas of my body.

I went through all my pants trying to find a pair that would slip over my heels. I ended up having to make a slit in the hem of a pair to get them over the heels.

Betty smiled as I made my way into the office, but she did check to see if the strap is in place. For some reason the work load the last couple of days skyrocketed, my desktop never seeing the light of day recently. I dug in to the pile of work, a welcome distraction to my ongoing efforts to become a female skilled in walking in heels. I might add that the nails were also quite a distraction, the look of the pink polish constantly making me aware of my feminine nails. Of course writing and using the computer keyboard suffered with the long talons attached to my hands.

The day labored along until right before lunch. Celeste turned up with a female reporter and a photographer. I sighed, knowing my time as a nobody is over. Nothing but front pages and hushed conversations from now on. As we made our way to the restaurant, there are many pictures snapped of me, and the entire lunch is spent in finding out the reason for me entering the contest, and why I had gotten the nail extensions. As Betty had prepared me, I told them that my reason for anything, but entering the event, is personal. My actual entry into the contest is that I support the charity and my company’s involvement in it.

It is amazing how many times the same question can be asked although worded differently, each new attempt trying to get a reason they can use to sell more publications. That day’s interview turned out to be the first in a soon to be everyday occurrence, Celeste telling me that at least I didn’t have to buy lunch now. My desire to cooperate also vanished as the same questions were asked, and in much the same way. I finally decided to give a little speech when we were first seated. “My reasons for entering the contest is to support the charity, a company project. Any more information is personal and none of your business.” I bit heavy handed but even then, half of them ignored my statement, and asked the questions anyway.

That night at the salon, my ears are pierced, a stud and a chandelier earring now in each ear. The dangling earring constantly reminding me of having them, swaying against my neck an erotic sensation that I had no prior training in how to deal with it. I am shown how to disinfect them each day, and that they would have to remain in, until after the contest before they are healed.

It was the next day, when I achieved stardom, my picture in the heels with long beautiful nails and pink polish made the front page of our local paper. From one of the employees in another division, Betty heard that the picture was also picked up by one of the national new agencies and appeared in several regional newspapers. I immediately thought of my sister, maybe a phone call tonight might be in order, to explain myself before she takes steps to have me committed.

Work is still the same, although traffic in front of my office is way up, all the gawkers wanting to see what the latest addition to my repertoire is for the day. Betty finally told all of them that I would visit the break room each morning and they could get their curiosity quenched then. That also became a problem when you try and get fifty people in a break room designed for twenty. I decided to walk the long way back to my desk after break, letting everybody get a peek at my preparations for the event. That afternoon, my eyebrows vanished, two highly arched lines above my eyes where before I had a semi bushy eyebrow. I first thought that the thin eyebrows would not be noticed that much, but after getting to reception at the front of the salon, and looking in the mirror, my face had went from cute male to gorgeous female. All of this without a hint of makeup on my face.

Unfortunately, the eyebrows was not the only hair that vanished from my body. The next evening my body hair became the target of their labors. Lathering a cream all over my body from my neck to my toes, the techs were obviously enjoying their tasks as they worked on me.Yes, my heels were removed for the hair removal. Twenty minutes standing there waiting for the cream to do its thing, shifting my weight from one foot to the other. Being naked, except for the cream doesn’t help matters any, then add the necessity to stand on my toes for comfort.

Finally the smiling techs removed the cream, and all my masculine hair with it. I never was real hairy, but losing what I had sure made my body appear feminine. The swell of breasts and wide hips are all I lacked to appear as a female. My penis seems to have shrunk to almost nothing, his forest of hair protecting him now gone.

The next day, I not only made the front page of the local paper, but there is also a quite lengthy article about me and the contest. Nothing real bad about me, but the event did receive lots of good publicity, even a couple of new companies signing on to support the event and contribute prizes.

Celeste made her trips to my office daily, making me model the latest changes to my appearance. I was constantly grilled as to why I had made the changes to my appearance, she knew it was Betty’s idea, but wanted to know why I was going along with it. She wasn’t upset about it, the charity getting a lot of free publicity and many new sponsors wanting to share in all of the hoopla. Most of the time she left my office shaking her head, I hope it is because of her fascination with me, not that she is disappointed in me somehow.

I never knew how to respond to her, I had bought into Betty’s plan, that is a given. When Celeste wanted to know why I was going along with all of this, what excuse could I tell her that would sound plausible? She apparently liked the feminine side of me, at least her comments earlier implied that, but she apparently had trouble with why I was going along with obviously female beauty treatments, looking more female every day. Maybe that is what she wanted, but she didn’t understand why I was so accepting of these changes.

The next day I did not make the front page, but got relegated to the second section. The picture of me no longer looked like a male, a young female suddenly emerging. When Betty informed me that my sister is on line two, I remembered that I hadn’t called her about what is going on. She said her hi’s and then waited for me to explain why her brother looks better as a female than she does. I am not sure she believed what I had to say, but I know that Betty had talked to her at length before the call was transferred to me.

She said she would come down for the contest, I tried to make it sound like it wasn’t worth coming, but she felt otherwise. “Brother dear, I wouldn’t miss this for anything. Maybe we can double date while I am down there. Surely we can attract some male attention, your looks sure to gather the eyes of some male admirers we might desire.” Believe me, I didn’t touch that statement, or even acknowledge it.

Celeste came into my office late in the day, right before my time to head to the salon. She had some unexpected customers coming in tonight and wanted me to accompany her to dinner. Betty heard that part of the conversation, and pulled Celeste back out of my office. They talked for several minutes, then Celeste left and I am hurried out of the office to the salon. “There will be a change in plans for tonight, just go with it and everything will be alright.” I started to say something, but she just pushed me faster out the door.

When I arrived at the salon, I am quickly led to the back, undressed and examined from the top of my head to my toes. Laid back on the table several boxes are brought in, and two quivering masses are placed on my chest. Another technician is working on my toenails and my hair is being shampooed and conditioned. Jasmine explains because of the guests tonight, I will have a lot of temporary procedures done so that I can attend the dinner with Celeste. Later, these temporary items will be removed and replaced with longer lasting appliances.

“I take it I will be a female tonight, will it be good enough to fool the customers?” Apparently Celeste knows about this, but me portraying a female in a business meeting was a little unnerving for me.

Jasmine just shook her head. “Your own mother will not be able to recognize you when we are done.” There is no part of me that escaped the treatments, a total head to toe transformation. The breasts get glued on, the weight of them not something I was expecting. A corset is fitted to my waist and tightened to the point of me almost blacking out. The laces are secured, then panties, a garter belt, stockings and a brasserie are added to finish the underwear. The bra feels good, my breasts feeling much better when they are supported some. Did I just say my breasts, maybe it is already too late to seek help?

My hair had been set in curlers after the shampoo, a dryer moved in and turned on so that my hair would dry. The warm air quickly making me doze off. I heard the dryer shut off, then the curlers are removed and another tech starts on my makeup. Too many lotions, creams, powders, and other assorted cosmetics are applied to my face. After removing my curlers, the curls are teased out some with a soft brush and treated with hair spray to maintain the style. A gorgeous dress is brought in, as I step into it and pull it up my body, the feelings kick in. I know junior is down there underneath all that lingerie, I feel him pulse a couple of times as the feeling of that dress makes me swoon.

The back zipper is pulled up, the bodice conforming to my new curves. Ready or not, I am ready for my evening with Celeste. Wait, no shoes, that is quickly handled but when I see them I just groan. A pair of heels similar to my gold pair, but even less straps if that is even possible. I teeter a little, suddenly feeling like I am walking on my toes, with two thin straps the only thing holding my feet in the shoe.

Speaking of the devil, she walks in, looks for me, then walks back to the receptionist to ask where I am at. I walk up behind her and tap her on the shoulder. “Are you looking for me, if so I am ready?” Her hand goes to her mouth, several OMG’s later, she calms down some, her surprise fading away as a sinister smile appears on her face.

She gives me her hand and we leave the salon, my heels making their presence known on the sidewalk outside. I am seated in her Volvo, and reach to fasten my seat belt. I take in a big breath, my simple act of sitting in her car totally dressed as a female, making me acutely aware of just how far this charade has progressed. Before I can overthink the situation, we pull up in front of one the nicer restaurants in town. Celeste hands me a purse that matched my outfit. “Betty thought you might need this tonight.

“The customers we are meeting tonight, have been with us for quite some time, in fact, they are ones that you have handled several times in the last few months. If we can, I prefer to keep your male self out of this conversation. You are my vice-president in charge of customer accounts, handling all matters with regards to new and established customers. They have stated that the reason for their visit is to renegotiate their contract with us. They want a larger discount in their purchases and a personal service representative in charge of their account. I see no problem with that, but I have informed them that you have the final say in these matters.”

My mouth fell open, she is dumping all of this on me, with me in all my feminine finery. We reach the valet parking, and our doors are opened and we are helped out. I almost forgot my purse, looking back quickly and grabbing it before I slipped out of the car. We entered the restaurant and stepped up to the Maitre D’s. Celeste told him we had reservations and was expecting guests. He told her that the guests were in the bar, and he would send someone to bring them to our table.

As we were seated, the guests arrived and she made the introductions. I swallowed hard, and told them that I had been informed of their needs. We will discuss this tonight, maybe we can work something out to please them. All of this in my best imitation of a feminine voice. No one seemed to notice anything, so I relaxed a little. We ordered and after our drinks had been delivered, I asked them to state their wishes, I wanted to make sure that I understood the problem. They told me their demands, showed copies of their invoices, wanting me to be aware of how much business they did with our company.

Then their CEO, a female that was quite young to be in that position, wanted to discuss their request for a personal customer representative to handle their business. In the past, they had an occasion or two when discussing an order with one of our representatives, had hit an impasse; our representative not able to help them because she was not familiar with their business. They felt the best way to handle that was to have one single representative to handle their business.

I knew her history, a daughter of the original owner who had passed the business over to her. I pretended to think about their demands, then everything got put off as our food is served. A little while later, our plates are removed, and after refusing dessert the business discussion resumed. “Jennifer, I will concede to your requests, both the discount and your own representative.” I immediately realized my mistake, the new me should not know her first name. She was quiet for a minute or two. I could see the wheels turning in her mind, then a smile lit up her face. “Charlene will you be so kind as to join me in the ladies room for a minute or two?”

I knew then, that I had blown it, what do you expect from a male dressed as a female and trying to conduct business that way. I got up and accompanied her to the ladies lounge. This restaurant had a separate lounge with couches and separate vanities for repairing makeup. I set at one of the vanities and started repairing my lipstick, hoping to deflect her thinking some. She sat next to me, and asked how long I had been living as a female? I told her about the contest and my volunteering to go the extra mile to support the race and bring more attention to the event.

She took it all in, then smiled. I will accept you concessions, but in the future, I want to deal with the female you, not that boring male image that you have. I told her the female me is only for the contest, then the male comes back. She smiled, “Then you will have to make an exception for me, if you still want my business. The female Charlene or no deal.” Sheepishly I agreed, maybe I can talk her out of this at a later date.

Back at the table, Celeste arched an eyebrow at me, wondering about our ladies room discussion. We talked a little more about business, there plans to buy a competitor would make them much more desirable as a customer than they were now. Finally, we broke up the meeting, shaking hands all around. When it came to Jennifer, she reached in and hugged me, telling me she would talk with me soon. Celeste and I left the restaurant, the valet getting her car for her, Celeste’s eyes focused on me. I am surprised she didn’t bore a hole through me with her staring.

“I expect a full disclosure tomorrow morning, but I do thank you for your effort tonight, all of it beyond your normal responsibilities and duties.” She let me off at my house, waiting until I am inside before she drove off. I wonder what she thinks of me, am I just someone she feels is cute or is there something else involved. I make it to my bedroom, strip out of the many layers, then fall into bed. It took me at least thirty minutes to wiggle out of the corset, but when that is accomplished, it felt so good.

I laid there for a minute or two, then got up and looked through my purse to see if Betty had supplied something to get the makeup off. The angel she is, had given me a pack of makeup wipes in the corner of the purse. Of course, there were a couple of other items in the purse, both of them I shook my head at, surely she doesn’t think I would need those female items with this male body.

Sleep couldn’t come fast enough, fortunately for me I was a sleep within a few moments of hitting the bed. I definitely didn’t desire to lay awake and think of what the night really meant to my future. That was a topic I wanted to avoid at all cost. Luckily for me, I also didn’t dream that night, at least nothing that I could remember.

Morning came way too quickly, after dragging my body to the bathroom, I suddenly sat up straight. I have boobs glued on to me, sizable as they are, I doubt if any of my male clothes will fit. I spent several trips back and forth through my bedroom trying to figure out what I could do. Then my doorbell sounded, and I tip toed to the door to see who it might be, through the peephole, I saw the image of Betty and I sighed. I opened the door to let her in, her giggling bringing my current state of undress to the forefront. “My you do look attractive, but to answer doors in the buff is usually frowned upon for a female, at least in your current occupation.” The smile on her face said it all.

She walked in with a garment bag over her shoulders, closing the door behind her. I am led to the bedroom and she unpacked the bag, my clothes for today. “Wouldn’t it be easier to just remove the breast forms?”

She smiled, “Probably would, but then Celeste misses out on seeing you in business attire. We can’t disappoint her after your evening out with her.” She handed me the clothes and I put them on as requested. I did feel better when covered up some, the bra especially felt good supporting my breasts. Betty helped me with my hair, a few twists here, a brush there, and soon my hair resembled last night. She showed me how to apply a few cosmetics so that I looked a little more female. Then grabbing my purse, we left to go to the office. Betty drove, since my driver’s license is in my male name, so using my car seemed to be off limits for a while.

We arrived at work, me following Betty to my office. I am definitely out of it, my mind still going over last night. I sat behind my desk, with my head in my hands, thinking of all that had changed in the last few hours. Number one is the breasts on my chest. I don’t think any male is aware of how much having breasts changes things. As you walk, they bounce a little, even held in a bra doesn’t prevent movement. That fact affects a male’s mind greatly, making it hard to be able to think rational thoughts.

Then you have the weight, constantly pulling down on the skin of your chest. The bra a much needed item of clothing. The fact that they are constantly in the way, any arm movement usually brushing against them, sometimes a nuisance, sometimes a pleasant feeling, as my mind reacts to the sensations that spread from them to the rest of my body. The caress of a skirt as I walk, another erotic feeling that is hard to ignore. Maybe a real female has come to terms with these feelings and can function properly, but a former male not so much.

“Celeste is on her way down here, she has been on pins and needles all morning, waiting for you to get here. After she leaves, we will talk, trying to get things straightened out and a somewhat normal existence for you figured out.” Those words muttered by Betty brought a halt to my daydreaming.

“You might want to read the email from Jennifer first, you made quite an impression on her and her associates, but it does have some long term implications involved with the deal.” All concerns were left as Celeste swooped into the office, coming up to me and hugging me fiercely. She pushed me back to get a look at my outfit for today, carefully taking in my appearance. I received several kisses on my cheek, and some hot breath on my ears. Goose pimples popped up everywhere, and my mind softened. Not quite goo, but very close. She swooped out again, a mini tornado, off to do more destruction to someone else.

I looked up at Betty as she returned, who is giggling her head off. “It is not funny, that woman can do things to me that should be illegal. I do wonder why she didn’t bring up last night, I know she wanted to know what happened in the ladies lounge, but I was too out of it to be able to figure it out myself.” Betty smiled that, ‘I haven’t the slightest idea what you are talking about’ grin, so I then knew she had said something to Celeste. For someone not being there, she has quite a bit of knowledge about what has exactly happened.

She allowed me some time to get over Celeste’s visit, then came in and sat in front of me. “Things have progressed faster than I had thought they would, so we now have to go to plan B. From now until the contest, you will have to act a female role 24/7. Jennifer is the one reason, breasts and the rest of the changes the other reason. Even at home, your hair, breasts, earrings, nails, and your changed face, will require you to portray a female.

“This morning you didn’t object much to the female clothes, even last night, the girls at the salon conveyed to me your fascination with your new image. You handled Jennifer well, for the situation Celeste put you in, a remarkable feat for a male. After she sent you the email this morning, I called her to discuss her intentions and her demands she made on you last night. She giggled quite a bit, she won’t hold you to anything you agreed to last night, but dressing as a female to handle her business would be greatly appreciated. She felt comfortable with you, even more so than in previous dealings.

“She did make a considerable donation to the charity in your name, hoping to sway you to her thinking. Continuing, “You certainly have this certain ability to draw out the female that wants you in skirts, two of the most ardent already in your corner.” I didn’t respond, just sitting there deep in thought. I do wonder if I will ever be able to return to the male role, but more disturbing is, do I want to? The salon appointments are put off for a few days, I am already going to work as a female, not much more can be done to make the charade more realistic. Well I am sure there is, but I am not wanting to go there yet.

Work progresses as usual, seemingly more problems appear on my desk than before. Jennifer does place a sizable order with me, one that I was not expecting so soon after our discussions. They did acquire the other company, now working on consolidating employees and offices. She promised another order the first of next week. She suggested lunch, her treat, on Tuesday, so I turned her over to Betty to settle on a time.

Betty did confide in me that Celeste is having problems keeping control of herself in my presence. “That girl has the hots for you in the worst way. I told her that I wouldn’t leave her with you alone, for fear of you getting pregnant, since I knew you weren’t on the pill.” Of course, Betty is splitting a gut on that remark, but my redder than red face, spurred her on to even more giggles.

I tried to get her to be serious for a moment, asking her what do I do with Celeste. She managed to quit her giggling long enough to ask me what I thought about Celeste. I thought about it for several minutes, wondering what I do think about her. She has always been my boss for the time I have worked here, we have shared in a lot of responsibilities and even in some accomplishments. I often looked up to her, since she has made a success out of her life, undoubtedly.

“I guess I like her in more than an employee-employer relationship, maybe even as a lover in a relationship. I know I have fantasied a lot about her in the time I have worked here. Betty, I am not positive, but I feel there is something else between us, maybe even romantic. I have been scared to death of saying the wrong thing to her, so have kept my feelings totally hidden from her. I presume the best thing now is to put my foot in the water and see if I can keep from drowning.”

I got hugs from Betty, as she told me she will handle the courtship. “The least I can do for two struggling lovers who are lost in the cruel new world. From now on, don’t hold back any emotions, if you feel like kissing her do it. By the same token, if you feel like being held in her arms and surrendering to her, that is also alright. I gave her a look, me being the female in a relationship and submitting to my lover’s advances, now that is way out there. I doubt that would happen, I am dressed as a woman now, but that does not mean I will act like one in a relationship.

It was shortly after lunch, when Celeste came into my office to ask a question about an employee that I had been involved with. The male had made some advances on two females, mostly unwanted, but denied doing it. I had interviewed all of their co-workers and found his actions were as described by the female employees.

I brought him into my office and laid it all out. I had testimony from ten of his fellow employees, both male and female, corroborating the two female’s complaints. I offered him several choices, all of them would result in demotion and loss of some pay. He chose to resign, the action I wanted him to take, a better solution for the company than me firing him.

I told Celeste I had all of the testimony and his statements on tape, plus his written resignation. I told her I would not give him a letter of reference or a good recommendation if contacted on his behalf. The employees who suffered his advances had also been told the same.

We talked about a couple of other business matters, then she asked me out on a date. I am shocked, the last thing I was expecting from her. I just sat there, not knowing what to say exactly. I immediately thought of office romances and their propensity to fail, but for some reason the idea pleased me. I nodded my head, and she came around the corner of my desk and engulfed me in a staggering hug and kissed me firmly on the lips. It took maybe twenty seconds, for the acting like a male in a relationship to go up in flames. I just stood there allowing her to hold me and kiss me passionately, just like a female.

Then just as quickly, she left my office. I could hear Betty laughing in the background and when she came into my office, the giggles only intensified. “I can see that I have my work cut out for me, she asked for a date, but didn’t tell you when. Then, you just let her sweep you off your feet, never thinking to ask whether the male or female you is involved, although I have a feeling it will be you in a gown on her arm. I will correct the oversights, but you will have to leave early, you have to buy a dress and get your hair done before the date. Since it is early, I should easily have you ready for a date tonight. Get busy on your work, and I will get back with you as soon as I iron out the details.”

I could hear her talking on the phone, to several different people. Since one of the calls is to arrange an appointment for me, I presume the date is for tonight. Quickly, she came back into the office and helped me complete my work, why I am involved, I really didn’t know. She handed me each document, explained it and then had me sign in the appropriate place. Paperwork that would have taken me an hour to complete on my own, we handled in about ten minutes.

She told me to grab my things, as she laid the papers on her desk. Then she grabbed my hand and we hastily left the office. My heels clacking on the hall floor, reminded me of how I was dressed and my foot attire. We took her car, and soon pulled up at the salon. This time we went in another door, and I stopped in my tracks as I saw a large store devoted to female apparel. Betty greeted an associate, apparently she had already talked with her and we were led to the back. On a rack, inside one of the dressing rooms were several dresses for me to try on. With Betty’s help, I was soon down to my underwear and trying on the first dress.

I instantly fell in love with the dresses, a male that finds the fancy dresses breathtaking beautiful not an everyday occurrence. As I tried each on, the one that I had on at the moment my favorite. Betty is having a ball, at my enthusiasm over the dresses, but knows we have to decide and get to the salon for my preparation for the date. We eventually decide on a LBD with a scoop neckline, exposing quite a bit of my breasts. It is trimmed in a lacey gold cording, with a panel of gold lace over the decollete of the dress. My gold heels that I adore and had to have, will go perfect with this dress.

Then it is out another door and into the salon. I am immediately taken to a chair and leaned back, so they could wash and condition my hair. After that, my hair is set in curlers and a dryer is brought over and placed above my head. The warm air flowing over my hair in curlers, encouraging me to drift off. As I got sleepier, my thoughts drifted back to a week ago when none of this was going on. I doubted I would feel comfortable in men’s shoes now, after my stint in heels. The heels feel normal to me, the arch of my feet now a comfortable situation. Well, comfortable for a short period of time.

Apparently I did drift off, the tech waking me as she pushed the dryer back to its resting spot. The curlers are removed and she works on my hair placing it in an up do, with dangling curls around my ears. My lipstick is refreshed and Betty appears with a garment bag to get me home. The drive is in silence, my thoughts on my hairdo and the date tonight. Several times my hand touched my hair, to make the fairy tale image seem more real.

“Come on girl, we have to get you ready and time is a wasting.” I didn’t even realize that we were in my parking space at my apartment. I am literally dragged to my door, Betty finally realizing that I was lost to the world, so she had taken my purse and opened the apartment door for me. I am led to my bedroom. “Get out of those clothes and spray a little perfume on your wrists, your neck and your female sex. Who knows, you might get lucky tonight.”

Of course, I turned every shade of red possible, dressing provocatively as a female to attract my female boss. A larger than real line that I am now crossing. Within twenty minutes, I was dressed ready for my date, at least physically. Mentally, I was a total wreck. The image in the mirror is of a female, dressed to the nines to go out on a date. The fact that I was male underneath those clothes, hair, and makeup is irrelevant at the moment. I am nervous, scared to death actually, but Betty has only one goal tonight. That is the date with Celeste, and her every action is aimed at getting me out the door on her arm.

Before I can get my wits about me, a knock on the door, and Celeste enters my apartment after Betty lets her in. She is dressed in a pantsuit, very pretty on her, but it seems that I am to be the attraction tonight, not her. Betty give me a hug and an air kiss, can’t mess up the makeup. I am out the door, swaying in my heels on the way to Celeste’s car. For some reason I feel great, confidant in my appearance and content to be Celeste’s date. Still the scary part looms in the background, I may be confident in my appearance, but scared to death of our budding relationship. Can I allow myself to be loved, to become a wife to Celeste? It seems that is the path before me, scared yes, on a path that I fear the outcome of.

She drives to a quiet restaurant that we had eaten at before some months ago for a lunch. Seated right away, in a cozy table for two in a quiet corner. “What can I get for you tonight, this is a special occasion and nothing is taboo tonight?” I really didn’t know what to get, my butterflies still had my stomach upset.

“Order for me, just not a lot, I have to watch my figure.” It is said in fun, hoping that my attempt to lighten the mood might work. I got a huge smile and she perused her menu. When the waiter returned to the table with our white wines, she gave him our order. It is all in French, so I am not sure exactly what I might end up with. The salads were delicious, the dressing had a light tang to it, with a little sweet touch to balance the tang.

Celeste wasted no time, engaging me in conversation about the contest and my job. Some of the things we had already talked about, but she wanted to cover the topic again. Then as our meals were being served, “Will you stay as a female after the contest?” I am sure the waiter was interested in my response, but he thankfully retired to help his other customers. I postponed the answer to her question, not really sure how I would answer. I did end up with a chicken dish, the sauce on the chicken and the asparagus on the side was utterly fantastic. I barely was able to finish the meal, my clothes now very unyielding, only allowing for a portion of what I used to consume.

The meal finished, I owed her an answer, and so far the events that have happened were fine by me, nothing bad had happened, doing my work dressed as a female no different than before. I decided the safest answer is to feign ignorance. “I am not sure Celeste, so far things have been okay, but I am not sure I want to live as a female for the rest of my life. Let’s wait until after the contest, then we can talk about it again.”

I hoped that we would keep things the same for a while, but am totally wrong. Celeste pulls out a jewelry box, took my hand in hers and opens the box. A gorgeous engagement ring of diamonds and rubies is inside, taking my breath away. “Charlene, I am totally enthralled with you, I have been ever since I hired you. These last few days have been wonderful for me, seeing you as I feel you are inside, knowing that you will be a perfect lover and wife for me. I can’t wait, I am offering the ring to you tonight, and every day from now on until you accept my proposal. I want to marry you, have you with me forever more.

“If you can’t accept tonight, I will be disappointed but will be patient until you finally give in and marry me. There doesn’t have to be a big ceremony, we can fly to Las Vegas, get married and then go on our honeymoon.

“I want you as your female self, the side of you that is the real you. I want to be with you, to share our life and maybe raise a family. The rest is all up to you. If you still want to work, that is fine. If you want to be a stay at home wife that is also fine. But I want us to be able to share our lives with each other.”

I had no idea what to say, this is not what I expected tonight. I knew Celeste had some interest in me, it has been fairly obvious. Marriage and I being the wife never entered the equation though.

The remainder of the evening, I was a little subdued. Too many thoughts trying to make their way through my mind. I think she knew her proposal had shocked me, she made numerous tries to engage me in conversation. I responded to her inquiries, but only short replies. She returned me to my apartment, with a kiss at the door to keep her in my thoughts. Believe me, she was the only one in my thoughts that evening. After undressing and cleaning off my makeup, I made my way to my bed, to lie awake for several hours thinking about the proposal. I liked Celeste; maybe even loved her, but me being the female and wife in the relationship, which threw a monkey wrench in the mix, at least to my male mind.

It is after two in the morning before I succumbed to sleep. I slowly made my appearance as my female work self, heels in hand, getting ready to go to work. I had called Betty, telling her that I would be a little late. There was no pressing matters to be handled that morning, so I dragged my feet going in. The taxi ride to the office spent thinking, the only result of that is a headache.

Since I dressed as a female every day, my appearance is no longer of interest to the masses, I made my way to my office without any interruptions.

“Well look what the cat dragged in this morning!” I smiled but left her statement unanswered. Of course, she knew something was bothering me and followed me into the office. She sat in the chair in front of my desk, staring me in the face. I put my purse in the drawer, adjusted a few things on my desk, but never did look up at her. She got up, went to close my office door, then came back and sat down.

“Alright, I need the whole story from the start, do not leave anything out and be quick about it.” She reached across the desk, grabbing one of my hands and squeezed it, causing me to immediately burst into tears. She released my hand came around the desk, making me back up my chair some and sat on the desk right next to me. She grabbed both of my hands, holding them securely in hers.

“Celeste asked me to marry her last night, to be her wife and lover. She said she will pursue me until I relent and marry her. I am sure she is serious, the size of the ring she showed me is huge, and so gorgeous. What am I going to do?”

I am comforted by her, it seems she suspected that might be a possibility when Celeste arranged the date. In the next hour, she managed to get me to relate the entire story to her. She is quiet for a while obviously thinking of the best advice to give me. It is my problem, not hers, but one that I have no clue as to the best way to handle it.

“Do you have feelings for her, if so, put her off until after the contest, then sit down with her and tell her how you feel. If there is some interest, explore it with some more dates, until you decide if being her wife is for you. I am sure that is what she has in mind for you, I think you would fit well in that scenario, but that is just my opinion.”

She had seem my eyebrows rise when she told me that I would fit in well as her wife. She forgets that I am a male, and males don’t normally become someone’s wife. “How can you say I would be a good wife, I am a male, the breadwinner in a relationship, not a weak, no backbone, type of person.”

Betty smiled, then pointed to my dress and heels. “The fact that you are dressed as a female and have been for the last few days, speaks volumes for your lack of a macho personality. You are handling day to day occurrences as a female does, you seem to enjoy your salon time, and I have seen the primping in the mirror as you get ready to go somewhere. All of this points to the natural female instincts that are a large part of you, deny it all you want, but you would make anyone a very loving and caring wife.”

I didn’t really know how to respond to Betty, maybe she is right about me, and I doubt many other males would have agreed to do what I am doing so easily. I seem to fit in more as a female than I do as a male, I can converse with them, even enjoy it at times. I know Betty and I are closer than most boss/secretary relationships, since I do not feel threatened by her actions, I am open to her ideas and opinions, most of which have been proven as the best approach to the problem.

We reached a joint decision about Celeste. Betty would have another talk with her, telling her that I would consider her proposal seriously after the contest, but for now, she has to cool it, to allow me to get my work done. An hour later Betty returned from her office with Celeste in tow. Celeste agreed to the hiatus, providing I took a small vacation with her after the contest. That way we could discuss her proposal and my answer to it. After a smoldering kiss from Celeste, she headed back to her office and I sat down hard in my chair. I am out of breath and very weak in the knees, Betty meanwhile just giggling away.

Betty decided that I needed to regain my front page appearances, the contest now only a few days away. She headed back to her office to plan a strategy and I sat in my chair and tried to regain my professional mindset. Eventually, I managed to get some work done, but I doubted that it is perfect. Betty has always checked my work before she sends it on to the company, so I am safe in that regard.

A few minutes before quitting time, she reenters my office with a huge smile plastered on her face. I presume she has found something to guarantee my return to the front page of our local newspaper. I handed her the work I managed to complete that afternoon and waited for what I will be doing next.

Betty sits in front of my desk, smiling and giggling, but trying to regain her composure. “To ramp up things a little you need to make some appearances around town, to insert yourself back into the news loop. I have arranged some meetings with several civic groups, the premise of your visit is trying to raise more support for the charity. Then an appearance at the local college during their annual festival, this more a meet and greet, answering questions about the charity and your involvement.

“The first meeting is the ladies Garden Club, tomorrow afternoon at three P.M. I am sure there will be press coverage, and probably pictures taken. A short speech, asking them to help support the charity, then answer questions. In the following days, the Chamber of Commerce, and two male civic clubs are on the agenda. We need to get you some new dresses for each day, a lady cannot be seen in the same dress two days in a row, unwritten rule number one.

Still looking at me, she continued, “I am working on several more meetings the first of the following week, then, we have the contest the end of that week.” I start to mention that this might be taking this too far; I am not sure how others will take to my dressing as the opposite sex, but then remembered this is Betty’s call on what I do. So far she has been right on everything she has asked me to do. I keep my mouth shut, what do I know anyway?

Later that afternoon, we spent a couple of hours shopping for suitable dresses to wear to these meetings. While we were shopping, Betty gave me some information on each group, the kind of questions, I could expect and some possible answers. She did have everything covered, already telling the groups a little about my motivation, my dedication to the company and the charity. “The men’s civic clubs will be the hardest sell, anything where a male willingly gives up his manhood bothers them. I selected both of these groups because the wives of the presidents are involved in the charity. I also alerted the wife’s, maybe a little pressure on their husbands might go a long way to make the meeting a success.

“Next week, I am hoping to get some prominent business women and you together for a luncheon, your treat, to discuss the charity and your involvement. So far I have four very prominent females lined up. I would like to get at least two more, I have several calls out now, waiting for them to call me back.”

“Betty, you know you are going to make me crazy if you keep this up. All the things you have put together are so out there, no normal male would ever touch this scenario, much less participate. I fear the effects on me might be a problem later; you know when I left the house this morning, I stopped at the hall mirror to check my makeup. Then glanced down at the back of my stockings to make sure the seams are straight. How will I ever be able to return to the male gender, these things are being ingrained in me, habits that I am barely aware that I am doing?”

“There is always room for one more female in society, especially one as pretty and smart as you. Besides I think you will find yourself as a wife soon, your lover so enamored with you, I doubt she will settle for anything else.

“Not to change the subject, but you do remember that you have a dinner meeting with Jennifer tonight. The silver dress with the pencil skirt should be fine, the black five inch pumps, perfect to go with the dress. Jennifer will pick you up at your apartment at eight. I have scheduled you a touch up appointment at the salon on the way home, so you should be ready to go after changing dresses. I would prefer you don’t get this one to ask for your hand in marriage, too many marriage offers tends to make the suitors very uncomfortable.” That last statement barely out of her mouth before she breaks up giggling.

Betty drops me off at the salon, then does a few errands before she comes back to get me. Sitting under the dryer, I had pondered about several things, who is paying for all of this the most notable. I decided to ask Betty about it. “Celeste had set up an account so that all of your expenses would be paid by the company shortly after you agreed to enter the contest. The least she could do for all of your efforts for the business.”

Entering my apartment, I had very little time to think about things, I slipped out of the one dress and into the silver one, although I had to shimmy myself into the pencil skirt. As I buttoned up the top portion of the dress, I started to leave one or two buttons undone, but quickly decided that a more prim appearance was a better idea. I needed no more attention than I was already gathering.

Jennifer is on time, takes my hand and we are on our way. She used a limo, so that she could indulge herself with some wine if she wanted. An oriental restaurant is the destination tonight, although a very upscale one. We were seated quickly, Jennifer wanted to know how things were going. I told her of some of the most recent decisions, she giggled and laughed at what I told her. We discussed my involvement with several of the clubs next week, she turned out to be a national member of a couple of them making notes to herself so she could be present at the meetings in our area.

She wanted to be sure that I would accommodate her wishes, to handle her business personally and as a female. I told her I would, but might have to make some time specific arrangements to be able to do so. I told her that I had been asked to be someone’s wife, if that happened, I would make myself available on specific days to handle her business, otherwise, I would be performing wifely duties. She guessed Celeste and I nodded my head. I was told firmly that she better be invited to the wedding, or she would have to complain to the CEO about my unwillingness to share my happiness with my friends.

After we ate our meal, the sweet and sour beef was the best I have ever had, we discussed her business. Their acquisition merged smoothly into the larger company, allowing them to see sales way above their initial projections much sooner than they had figured.

We finished our meals, with much of the dinner talk about Celeste and me. She has been equally impressed with my female presentation, and if Celeste had not already staked her claim, she told me that she might have placed an offer too. We became friends during dinner, confiding some personal things about ourselves with each other. We joked, laughed, and generally had a good time, the restaurant wanting to close the only thing that ended the discussion between us.

Jennifer wishing me luck with my romantic relationship, but insisting on me being her personal representative in the business, as we parted company at my apartment. I got a little friendlier kiss than is exchanged between friends, but thankfully nothing similar to the ones that Celeste has dished out recently.

I took my clothes off, removed my makeup and slipped on a nightie, a first for me. They had been purchased earlier, but I had not worn any before tonight. It felt right somehow now, I had finally accepted that I would be female in the future, still not sure about Celeste, yet positive that I would be living the life of a woman.

The next day another dress, this time a little more simplistic, a ladies garden club meeting not a high fashion affair. I was greeted warmly, they listened to my involvement in the charity drive and then the formal part of the meeting was over and quite a few of us chatted for almost an hour. I was made to feel welcome, they even invited me to join their group. I told Elizabeth, the president of the club, that I would consider once I had something that might resemble a garden. I made a lot of friends, all of them amazed at my ability to handle the tallest of heels with ease.

The next day at the university was the meet and greet. It was part of a quarterly gathering where charities, employers, and other interested parties could connect with the students, to further their interests, or just get some exposure for their company or cause. I was surprised at the interest shown to me, the questions quite soul searching. I was up front, not hiding anything, but did keep some of my personal reasons for doing this still under wraps. I received lots of hugs from the females, they somehow connected with me, the fact that I was basically a female at heart, probably the real reason. The real gain was the number of women who showed interest in working for our company, the fact that I did this willingly, speaking volumes for the company and me.

I did get two comfortable night’s sleep, the male civic clubs turned out to be not a problem. The head of the organizations had been briefed by their wives. I was greeted cordially, treated as a natural born female, even managed to get a donation from each group for the charity.

The luncheon turned out a little different. Six members of the business and professional community, all self-made females that had made their way through the maze that exists today. We did the introductions, talked a little and then had a pleasant lunch at one of the better local restaurants. It was a private room and we had a waitress to handle us alone. We nibbled a little and I explained my participation in the contest and my reasons for doing so. They listened attentively, but I saw more than an eyebrow or two raised after a few statements.

Betty thought that might happen, so I was prepared for the question. Ms. Davies, a prominent attorney in town, asked the question, “I see before me a poised female, quite good looking and very intelligent. The reasons you have given might satisfy the news people, but you are dealing with females that know better. Now how about being truthful and letting us in on the real reason. I can hazard a guess, if you are too shy to fess up.”

“My boss thought that when she hired me, I was cute. The contest came up and she raised my hand. After a few steps into the world of femininity, she expressed her desire to marry me, a probable occurrence once the contest is over. I have found, I enjoy the life of a female, am fairly good at it and want to continue possibly, forever. All of this happened because my secretary saw this inside of me and decided the female me needed to be let loose. Well, since that has happened, I doubt that the female me can be put back inside the male body. I am pleased to be able to socialize with you, a real treat for me. Maybe you can see your way clear to make an additional donation to the charity. For that I will be eternally grateful.”

I sat back down at the table, after adjusting my skirt. I looked around and each lady was searching in their purse. In a short amount of time, I had six checks in my hands, each for far more than I thought possible. I got up and gave each lady a tremendous hug thanking each and every one for being so generous. I had tears in my eyes, I was truly touched by their friendliness and caring. We talked for a lot longer, they suggested some things I might be interested in joining, female organizations that truly make a difference, not just talk.

One lady invited me to go with her next time she visits the children’s ward, I eagerly accepted, something I would feel good about doing. The luncheon broke up five hours later, all the hugging and attention I received very encouraging. I drove back to the office, entered and stopped at Betty’s desk. I told her to call Celeste and get her down here right now. Do not take no or maybe for an answer. I went on in to my desk sat down in my chair and slipped off my heels for a minute or two. Of course, Betty caught me with my heels off and started to gripe about it. I stuck my tongue out at her, she started giggling, and then Celeste walked in.

I pointed to a chair and told her to sit her butt down. Quiet filled the room. I opened my purse, took out the six checks and laid them on the desk facing her. Betty was the first to see the figures and took in several deep breaths. Then Celeste saw the amounts and attacked me right across the desk. Betty grabbed the checks just in time, as Celeste slid across the desk into my lap. I was woman handled in a quick and concise manner. Betty just giggling at Celeste’s efforts. When the dust cleared, I had lipstick marks all over my face and neck, my hair was a mess and my dress was twisted up in spots where Celeste had tried in vain to get it off me. Betty had left for a minute, coming back with an adding machine tape, apparently I had raised sixty-eight thousand dollars for the charity in less than six hours.

Betty suggested that Celeste call the charity to let them have the good news and allow her time to get me back to looking presentable. I went to the bathroom, using makeup wipes to remove the lipstick. After working at it for ten minutes, I decided to remove all the makeup and start over, a much easier task. It was quite a few minutes later when Charlene reappeared. I stood looking at my image in the mirror, almost three weeks ago there was just Charlie, now so much more.

I turned from side to side to get a better look at my overall appearance, the image quite pleasing to my eyes. When I decided I needed to get back to my office, Betty was standing in the door. “You are going to stay as Charlene aren’t you?”

“Yes, I am. At first it was just something crazy, Celeste being her usual mentally unstable self. But the more I got involved, the more Charlie slipped away. When I look in the mirror, there is no Charlie left, only Charlene. I am still unsure about Celeste, I think I love her but there still is a smidgen of doubt. Either way it will be as Charlene, the male me now totally gone.

I do want to continue to work, at least for several years, and I want to keep the relationship the same between you and me. You do my work anyway, I will see that you are paid for it, but I treasure our friendship and that I will not let that slip away. If you want, we can switch jobs every once in a while, I would love to be your secretary, but you would have to put up with my less than brilliant work. We hugged and kissed, not romantic but between two close female friends.

I decided my work was done, with the contest tomorrow I need my beauty sleep. Betty reminded me of my seven A.M. salon appointment, we hugged as I groaned. Being home was surreal, an obvious female in a masculine decorated environment. After the race, I will re-decorate, masculine out feminine in. I just nibbled a little, not really that hungry. I cleaned up some, then retired to my bedroom, got undressed and slipped into a baby-doll nightie. I opened up my laptop, was going to surf the internet, instead I found some of my favorite music. Listening to some of my favorites relaxed me and soon I was sound asleep.

The alarm at five A.M. did get me up. Instead of hitting the snooze button, I got up, did my bathroom thingies and started getting dressed. Minimal makeup since a female has to be presentable before venturing out, then left for the salon, where they would handle my event face, the rest I’d handle myself. I dressed to the nines, if I was strutting my stuff today, I was doing it in style. I chose a pencil skirt, the last three weeks I have had a lot of practice in different ones, and I love the look and the extra sway they add to my rear when I walk. The lace blouse matched perfectly, the two shades of ivory complimenting each other without making it seem like it was a dress. My white bra showed clearly underneath, but the layers of lace made it look proper. My gold stilettos that Celeste bought for me were my shoes of choice.

I drove to the salon, parked and entered the salon. I was immediately escorted to one of the styling booths and three stylists attacked me. Shortly my hair was in curlers, my makeup is being applied and fresh nail polish is on my ten fingers. A burgundy nail polish with extensive flowery nail art in shades of ivory, the centers of the flowers left the dark rich burgundy. An explosion of bright miniature ivory flowers is what my fingers looked like.

The makeup was darker than usual, the lights of the auditorium and the bright sunlight later sure to pale my made up face, hence the darker more bold colors. I received an up do today, with rings of curls cascading from a spot high on my head. Ribbons were added in burgundy and ivory to tie the colors throughout. Off to my runway walk, as I entered the auditorium, Betty met me at the registration desk and showed me where I could sit until the contest started. They had quite a crowd, the auditorium almost full now, thirty minutes before the festivities are to start.

I looked around for Celeste, Betty saw who I was looking for, reminding me that she would not miss this for anything. I saw several news crews, one of us or all of us would be on the evening news that is for sure. They had got the governor of the state to act as Master of Ceremonies this afternoon, he made the round introducing himself to all of the contestants. When he got to me, he took my hand and kissed the back of my palm. Of course, I was blushing now, blood rushing to my head to insure a rich deep red when anybody looked at me.

“It is a pleasure to finally meet you Charlene, such a fine young female who has single handed made this contest such a success. I respect you and value our friendship, if you would be so kind to allow it.” I now understood how he got elected, a smooth talker indeed. Still it made me feel good.

The contest started soon thereafter, each participant made five walks up and down the runway to allow the judges to evaluate our ability in heels and our appearance. The judges were located down at the other end of the runway, where we had to execute a turn and return to the starting point. As we made the runway walks, the MC told some about each of us, our age who we worked for and our reason for entering the contest. When he got to me I wondered what he would say, I never gave any specific reasons for entering the contest other than to help the charity. As it turned out, I was the last entrant to walk the runway.

As I made my way down the runway for the first time, I heard the voice of Celeste over the speaker system. She had replaced the governor, at least, in my case. The applause more than I expected, as I completed the runway walks. The audience invited to accompany us on our stroll through town, then back to the auditorium tonight for the announcement of the winner.

I was stopped quite often, people wanting to give me a hug, shake my hand and hand over another donation. One of the organizers had to give me a pail for the donations, even that had to be replaced before I made it to the end of the walk. Overflowing with more contributions.

There was enough time to grab some dinner before we were due back at the venue, Celeste already having reservations at an upscale restaurant near the venue.

Back to the venue, and my nerves are pure raw energy. I can’t stand still, not knowing who will win, but fearing what will happen if I do manage to pull it off. A feather in my hat with the company and Celeste but maybe too much publicity for my shaky male persona.

Declared the winner, I was lost for words, tears rolling down both my cheeks as I was handed a bouquet of flowers for my efforts. Celeste telling the crowd that Charlene will now head up the company and also be next year’s chairwoman for the charity drive. I shook a lot of hands that night, congratulations given me from way too many people. A lot of the people I had contacted in behalf of the charity, now wanting me to serve on some of their committees and two wanting me to be a member of their Board of Directors.

After all the festivities are over, Celeste gathered me up and took me to her home, given some dainty night clothes to wear, we sat in her living room in each other’s arms, sipping some wine and discussing my new role as wife and significant other to her. When we adjourned to the bedroom, my future had been planned out, one that I was looking forward to living.

Celeste was moving on to a new company that she had bought controlling interest in, looking forward to the new challenge that faced her. I took over for Celeste, Betty my secretary to keep me straight and in control of things. The ramifications of winning the contest and my participation went far and wide. Over the next year I was appointed to six different Board of Directors, joined many civic organizations, even headed up a couple before I had been with them a year. I did chair the charity drive the next year, we met every goal we had set, even getting a few companies to donate some money every year to the charity without having to be asked.

Celeste and I built a new home, I designed it and Celeste saw to it that it was built on time and under budget. We had fun decorating it, shopping far and wide for furniture and accessories for our new home. After we returned from our honeymoon, we made specific plans for our future, plans that included children, Celeste to have them, Charlene to raise them. I stayed on at the company as CEO, but Betty as COO actually ran the company. Jennifer’s business grew by leaps and bounds, now her company is our biggest customer, one that I handle myself personally, exactly like I promised years ago.

I get to have my beauty salon time at least twice a week, more often if something special comes up. My wardrobe is now encompassing three closets in our house, maybe more in the near future. The one thing that has remained constant is my love of high heels. Not a single pair of shoes with less than a three inch heel, more than half over five inches. The last time our housekeeper had to move them to clean them there were more than two hundred pair, not a single pair I could do without. At the cost of each pair a considerable investment, but so worth the money. It all started with my heels on the runway, a time I often think of and treasure.

© 2016 thru 2024 by Francesca

Millicent; Living The Dress Code

 Millicent; Living The Dress Code

I was getting dressed after a relaxing hot shower. I was savoring a recent encounter with Cassie. We had met at a company office party for the holidays. I had reluctantly went to the party, my supervisor insisting that I attend; so I made my appearance, planning to leave early. When I saw her, I was immediately fascinated by her, a blonde, fairly tall with a well-proportioned figure.

Translation: gorgeous and stacked! I made a point to introduce myself, she was cordial, but no bells ringing or fireworks going off for her apparently. The introduction was one sided, I introduced myself and she shook my hand, that was it as she walked off talking to someone else.

She worked in advertising, preparing the weekly ads for our store. According to others, she was good at it, already impressing the higher ups. The reason I had not seen her around much was she had only been working for the company for four months. A little detective work on my part and I found out her name was Cassie, single and living alone. This information was obtained from some of her work colleagues, carefully and surreptitiously.

However, I was devastated when she showed no interest in me at the party, since I was already hopelessly in love with her. It’s true about love at first sight, but also true about how painful it can be if not returned. In many ways, I have always been a romantic, unfortunately very few women have responded to my efforts, or shared in my romantic thoughts and actions.

For a couple of months nothing much happened, I watched from afar, hoping and wishing for another meeting or confrontation. I worked in personnel, writing company rules and behavior for employees. We were a large company, having over three thousand employees. There were constantly issues popping up that needed to be addressed to insure that proper decorum was maintained. Sometimes a simple few words, other times a few pages to address the issue.

My next meeting with her turned out to be at a gathering to discuss the new company dress code. The one we had was archaic, probably written during World War Two. I had several of these meetings scheduled to find out what the employees thought of the dress code we had tentatively drafted. My boss and I were representing the company, but I had written the proposed dress code. Jennifer was my boss, but she usually let me do my own thing knowing I would do my research thoroughly, and not just arbitrarily decide on something.

A few minutes into the meeting, Cassie seemed to take over the employee’s side, confronting me on several provisions of the new dress code. I discussed it with her, could see her point on a few matters, but also stressed the need for some concessions to insure we offered a professional appearance to the customer.

We are a chain of retail stores selling mainly female fashions and accesories. I know a female these days feels more comfortable in slacks, but it is hard to sell dresses and skirts when you are not wearing one. The same with makeup and jewelry. The discussions stayed pleasant, we continued to exchange ideas and opinions, but we’re still miles apart on a compromise.

The present employee group at the meeting asked Cassie to represent the employees in any further discussions. My boss approved, since Cassie had been courteous, even though she represented the employees, she was respectful of the company’s viewpoint too.

Over the next few weeks, we met often, hammering out some changes to the dress code. Cassie was pleasant to work with; we talked, sharing our opinions and disagreements. It was coming down to the time to make a final draft of the dress code, when Cassie asked to have a meeting with my boss and the CEO of the company.

I agreed immediately, maybe they would settle on something between the three of them, making my job so much easier. The meeting was set-up for a few minutes after quitting time, since Cassie had a newspaper ad to get ready, and my boss had meetings with employees all day right up to quitting time.

The meeting was in the CEO’s office with all of us arriving by five after. I let everyone read the latest draft of the dress code, my boss smiling, but not saying anything. The CEO asked some questions, she was very intelligent and had worked her way up from sales clerk to where she is now. Cassie stated her concerns, while conceding some for the company. Then she dropped the bomb that would turn my life upside down.

She wanted me, the creator of the dress code, to live as a female, obeying the new rules to the letter for a month. She would even concede to the implementation of the new dress code now, as long as I obeyed the rules for a female. She also wanted me down on the sales floor in that role, working in an office was not representative of most of the female employees. I stared at her, where did all of this come from? I swallowed hard as the CEO asked Cassie and me to step out of the office for a minute while her and my boss had a little conference. Apparently Cassie had blindsided them too. My only thoughts, ‘Oh shit’!

Cassie and I walked out to the outer office, she smiled at me, then told me it was nothing personal, but most of the females resented a male writing the dress code. She understood that a female writing the dress code for guys would have the same problem. When she suggested this to her fellow females, they all agreed that if I could handle the new dress code as an everyday occurrence, they would concede to its value.

I had a new respect for her even if it meant me being shoved in front of the bus. We were out there for almost thirty minutes, a lot longer than I anticipated. I had an idea the talk was all about this plan of hers and how it would impact me.

Cassie was summoned first, that did not sound good for me. Thirty minutes later, I was called back in.

The CEO started by saying, “We have come to a decision that all here have agreed to. It will have the most impact on you that is why we have taken quite a bit of time to try and address these issues. First, if we can come to an agreement that will allow you to do this without affecting you negatively, would you consider doing it?”

I nodded my head in the affirmative, my mouth suddenly unable to form words, much less speak them. During my exile in the outer office, I tried to figure out if I would agree to the idea, or if I should just refuse and walk away. I felt it would probably negatively affect my job if I refused, since I did write the dress code. If I had so little faith in what I wrote down that I would not back it up, that could transfer to my ability to do my job. The big problem is that I am a male and the contentions with the dress code are dealing with the female presentation in the workplace.

Looking at me, she continued, “Wait till we cover all of the things we have come up with so far, and we can discuss them later. Now, since most of the females in the company have signed a petition formally advising us of this plan, we feel it deserves a chance. Cassie has followed procedures, making sure it is not just the opinion of a few. She has presented us with the petitions with no formal demand behind them, just the wish that this be tried so that management might see their viewpoint.

If you agree to participate, you will be transferred down to the sales floor, spending a week each in jewelry, cosmetics, lingerie and women’s fashions. The one reason they had picked on you is that you could probably pass as a female, therefore, not jeopardizing the reputation of the store as this is tried.”

“As far as the company is concerned, we want this not treated as a joke or prank. We will provide you with adequate support so that your impersonation will be fairly realistic. That would include any beauty treatments necessary to give you a female appearance, a wardrobe befitting a sales associate complying with the new dress codes, and any support necessary to help ease you into this role.

Cassie has suggested that you move in with her for the month, she has a two bedroom apartment and plenty of space. That way she can advise you in appearance and behavior. She has assured us that you will be treated as a female roommate and nothing more. That help might be critical since you have not lived as a female or dressed as one for any prolonged period of time. The fact that you do not have a girlfriend or wife suggests that the added help might be quite necessary.” Those last sentences delivered with a little smirk.

“To keep from subjecting you to possible ridicule from within the company, I suggest we treat you as a new hire, changing your personnel file as to your gender and name. That way, only the four of us will know your true identity and what is being done. Your paychecks will reflect your new position, later, we will compensate you for the difference.

During Cassie’s discussions with her fellow employees, your name was never brought up, just that a male member of management would be asked to spend the month as a female sales associate. To cover your absence in personnel, you male self will be transferred to one of our distribution centers. There is actually some problems in the distribution center, having to do with maximum loads lifted so that should provide adequate cover.

There is very little contact between the center and any of our sales associates, a likely believable excuse for your absence.”

My head was spinning as she continued, “The dress code will be implemented, but our supervisors will be told to go easy in enforcing it except for you. You will be expected to adhere to the proposed code explicitly. That way we can get a truer read on its benefits or disadvantages. I know this is far out, but we think a lot of good can come from trying this.

Of course, the end decision is strictly up to you. Why don’t you take the evening to think about this, a hasty decision often is a wrong one, and we can reconvene here in the morning? Since you two will be interacting a lot, maybe a dinner paid for by the company might make both of you feel a little more comfortable with each other.” Jennifer did ask if I had any questions on what has been presented so far, since my mind was in a molten state I could not come up with coherent thoughts, much less a question.

I nodded my head, still at a loss for any verbal output. Cassie came over as we were getting ready to leave, suggesting a restaurant and a time. I agreed, finally managing to get out a ‘yes’. I drove home in a daze, my whole world upended. I took a shower, letting the hot water run over my body until I had used every drop of it. It did help, my mind was actually functioning by the time I had put on some clothes. I drove over to the restaurant, meeting Cassie in the lobby. I received a hug, surprising me, her excuse is, “That females hug all the time.”

We were shown to our table, in a more private room separated from the main dining room. She informed me that she eats here a lot, her cooking skills nil. I thought if we do cohabitate my cooking skills might be enjoyed by both of us. We ordered, then talked about work. She apologized for cornering me in this scheme, but honestly thought management did not understand some of the female’s concerns. Even if nothing of the new dress code gets changed, the females feel that at least the present management listened to them for a change.

I could see right there where I had initially messed up. If I had scheduled the meetings before any new dress code was put on paper, it might have gained some support instead of the way I presented it. Live and learn, I imagine I will be doing quite a bit of that in the next few weeks.

It was an enjoyable meal, both of us having chicken salads, the chicken seared over a grill. We split a decadent chocolate mousse, so good and quickly disposed of. She invited me to her apartment so that I could see where I would be living. Away from others, she is very personable, extremely cooperative and quite funny.

I followed her to the apartment, a nice two bedroom townhouse type located near a park. I was shown the bedroom I would be staying in, then we returned to the living room. She made some tea for us, we sat on her couch sipping the tasty brew as she asked me what I thought of the situation.

“It surprised me, something that would have never crossed my mind. Maybe it will make me aware of some things. I first have to get over the gender change that I have to submit to. For a male to suddenly live as a female for a month is pretty radical stuff.” She nodded an acknowledgment. It is an unusual way to approach the problem, but up to now management has listened but ignored any complaints or suggestions that might make the dress code more palatable to the employees. Thinking back on the recent meetings what she is saying is completely factual.

She also suggested a salon in town that could help me prepare for the month long life of a female. She had already contacted them on the company’s behalf, now they were just awaiting for a call from me for an appointment time. She told me the salon will furnish everything, including the clothes, or I could do my own shopping elsewhere. That said with a devious little smile and giggle.

I had been formulating a reason for all of this, seemingly random things have been somehow pulled together into an elaborate plan. It appeared way too coincidental. I think everyone was severally underestimating Ms. Cassie.

“I sense there is something more to this than just a concern over a dress code? Would you care to elaborate on the real reason for all of this?” I asked with a straight face.

I got a snort, a giggle, then a huge smile came across her face. She placed her cup on the coffee table and moved right next to me, I mean right next to me. She leaned over and kissed me on the lips, her tongue invading my private space. I opened my lips a little allowing her greater access, her tongue probing the depths of my throat. I could taste her lipstick, and thought to myself, ‘maybe this won’t be so bad’.

It did throw a wrench in my thought process, now everything that might have been considered conventional thought suddenly tossed out the window. I was going to say more, several questions now begging to be answered. Instead, I withheld, time will take care of the questions, a few of the answers I may not want to hear just yet.

After the first kiss, she withheld any further rewards, the giggle and smirk telling me that any further rewards would have to wait until I was feminized. “I have standards and can’t be seen with just any male.” I presume that would allow me, dressed as a female, to be seen with her.

We resumed normal male female interaction, her being somewhat aloof, tantalizing close, but no touching. We discussed the splitting of household chores, dressing as a female also coming with chores and duties. I would buy the groceries and cook. She will do the vacuuming, dishes and trash duties. We will both do the bathrooms, since there is two, one for each of us. We will do our own laundry, with me doing the towels and incidentals for the kitchen and bathrooms.

She suggested a week to make the transition, getting used to new feminine attachments, clothes and acting like a female requiring more than just a few days to be convincing. The idea was not to disrupt the store’s business or reputation in any way. I got a hug as I left, many things on my mind as I made my way home.

The next morning, at the office, we met again and I told them I would do it. I was awake most of the night, trying to figure out if I was going to do this or just run for the hills. Cassie was smart, the way she presented this it made it almost impossible to refuse participating. The company agreed on a week’s vacation so I could get into the role, then start at work the following Monday in the cosmetic department. In each department, I would be shown what to do the first day, then the remainder of the week, test out my skills while dressed as specified by the new dress code.

I made the call to set up an appointment for my transformation, and was given one later in the day. I was surprised at the quick response, but figured it was better to get it over with. I cleaned up any projects I was working on, assigning them to others to be worked on. My boss changed my personnel file making me a new hire as a sales associate. A female name was assigned, Millicent Ann Templeton, and I got my first shock.

My new pay rate was only half of what I was getting now, I suddenly realized how difficult it would be to live like I had been on that meager salary. I also found out that I would be working fifty hours a week, the minimum for salaried employees. I left her office in a daze, I still have on male clothes, but the female life has already intruded on me hard! I bid everybody goodbye, keeping up the story of my transfer to a distribution center.

Next stop, the salon. My first impression of the salon was comical. My mouth was open as I walked in, the place was huge. I am sure I looked comical with my mouth agape taking in the scene before me. Customers and stylist everywhere, probably a hundred people all together. I was expecting some small shop with a couple of ladies, not this feminine mega world.

I was taken to a treatment room and stripped of my clothing. I had already been informed of all the changes specified by the company when I called for an appointment, so that part was already handled. I signed some papers showing that I was fully informed of my treatments. Apparently Cassie and my bosses had contacted the salon initially with what treatments I would need setting this all up.

With that completed, I was laid back on a table and cream spread all over my front side. No area was missed, even my privates were slathered in the cream. Usually something creamy applied would have caused a stirring down below, but not today. Shock and humiliation having its effects on my equipment. Thirty minutes later, the technician used a towel removing all of my body hair. The backside was handled the same way; now, I was totally hairless from the neck down.

Although most of their customers were supposedly male, from what I can see there are few if any males here now. Surely they can’t be so skilled in turning males into females. I asked my technician about their customers, she confided in me that most here now are males, just in varying stages of their transformation.

Another look around and I knew I would blend in easily when I left the salon, probably too easily. Very unnerving to an insecure male, that thought his masculinity was strong enough to go through the change and still appear male. Maybe this wasn’t such a good idea.

The next few hours were very stressful for me. They knew what they were doing, it was me that couldn’t keep up with the changes to my body. My ears were pierced, two holes in each ear. Then my eyebrows were removed, well almost completely done away with. Now two highly arched thin lines above my eyes, way too feminine in my opinion. My hair shampooed and conditioned, then partially dried.

When she started sectioning my hair and applying a paste to the separated sections then wrapping them in foil. I knew my looks would be drastically different when she finished. My natural blonde hair would now have brunette highlights blended throughout, making for a rather feminine look. Management felt that was necessary to assure nobody would be able to recognize me as my former male self.

As that was being accomplished, my nails were being worked on, the long extensions that had been glued on to my nails were sure to make my work at the store harder than I envisioned. The new code did require long polished nails, just not the length that was being applied to my fingers. I am sure though the overall look will be quite feminine. I got bright pink polish, way too many coats of it, guarantying some female looking hands for weeks.

I tried to touch my ears to feel the earrings that were swaying against my neck and almost poked a hole in my ear at the same time. Until I could get used to them, they were a dangerous weapon, at least to me. The nails, jewelry and makeup are part of the new dress code so having these things done was just preparing me for next week.

My body was not to be ignored, breast forms were glued on and my male apparatus was glued away behind a lovely fake vagina. Both the breasts and the vagina were very realistic, almost undetectable. My eyes were drawn to the vagina in particular, then I would blush and look away embarrassed at my unnecessary interest.

I soon found my breasts to be just as much of a problem, every movement of my arms touching or rubbing against one or both. Not a comfortable feeling for a male. I guess that should be former male, my image in the mirror, showing no signs of a male, only a desirable female. As my arm brushed one of my breasts I felt the touch. How can that be, a blob of silicone and I can feel as if it is touched? My tech seeing my questioning look told me that the breast form uses sensors in the form to transmit touch to my nipples primarily, then that is spread to the rest of my natural breast.

My hair was finished, the highlights had taken, now my hair was almost a work of art. Instead of curlers a spray was applied to the hair then a curling iron was used to set the curl. The spray a new development of their company, the curl now would last for months, just brush it into place and you are ready to go. All I heard was ‘months’, since my highlights were dyed in they too would be around for quite some time. Somehow my one month as a female on the sales floor had morphed to something more.

Cassie again? Who knows, something I need to follow up on though. I hope her plans for me don’t include me getting pregnant with her child. A wild thought? Maybe not so much at the rate and degree of my feminization up to now.

Once my hair was coiffed in the latest style, I was shown how to brush it back in place. I came to the conclusion that my coiffure would be with me for quite some time, after I saw how easy it fell back into place. Makeup was applied, some stains and tints lasting for much longer than regular cosmetics. Let’s face it, Millicent is going to be around for far longer than a month.

I was taken next door to their clothes store, and seven outfits were picked out for me, business professional all meeting the new dress codes. This was for my one week of training and acclimation. When my feet were slipped into the heels. I knew I had shafted myself right away. At the time four inch heels were popular and almost a standard with professional women. But a former male in four inch heels, that is another story. It wasn’t fifteen minutes and my feet were aching, but since I had written it into the dress code that was the shoe of choice. As all of my outfits were being bagged for me, guess who shows up. Yep, Cassie with the biggest shit eating grin plastered all over her face.

I was hugged and a cheek kiss, then she literally dragged me from the store. We had to return to get the rest of the bags, but Cassie was on a mission and apparently it was a time sensitive mission. I managed to slide into her front seat, the new skirt I was wearing keeping my legs tightly together. I no sooner got my door closed and she shot out of the parking lot. At every light I was appraised and then with tires squealing we headed further down the road after the light changed.

I was watching how she was driving and not where we were. Soon we pulled right into her garage, the door closing right behind us. She got my door for me, and with a death grip on my wrist, I was wrestled into her bedroom.

Clothes were coming off rapidly, mine seem to be disappearing faster than hers. I was pushed back on the bed and her mouth found mine, her tongue wasting no time in probing my throat. I was giggling at her antics, then she grabbed hold of one of my nipples. I felt it, not something I thought possible with breast forms, but these seem to be quite special.

She pulled on the nipple elongating it as her mouth continued its probing of my mouth. The feeling of the nipple being manipulated was attacking my mind, wave after wave of pleasure hitting me, but making me feel so good. I could taste her lipstick, maybe it was mine, whatever, it tasted so delicious. I was somewhat aware, but also lost in the sensations that had consumed my body.

When she removed a dildo from her nightstand drawer, I swallowed hard. Before I could protest it was inserted in my new vagina, my body reacted in an explosion of feelings. I had experienced a male orgasm before, several times in fact, but unfortunately not with a female. This was so much more than that, bells ringing, lights going off, muscles contracting, and then a tumultuous release of fluids.

I was embarrassed, just the insertion of the dildo had done this to me, no pumping, no squeezing, just one swift long stroke and I exploded in bliss. Cassie’s mouth had found one of my nipples, sucking on it as I came. The good feelings lasted after the dildo was removed, small quakes still vibrating through my body. I was spent, totally spent.

She cuddled me for quite some time, my need for doing something about the liquid leaking from my vagina putting a stop to the cuddling. I was a sight as I waddled to the bathroom, one hand over my vagina trying to keep some of the liquid inside. Talk about humiliated, this had to be the worst case of it known to mankind.

If Cassie had not been giggling up a storm, I might have suffered through it a little better. I set on the toilet, my first time as a female, cleaned myself as much as possible, then took the time to pee while I was there. Then I had to wipe myself again, the moisture all over my nether regions. I was still dripping from my vagina, Cassie watching from the door, giggling away. She handed me a pad, something a female would use during her period. I shook my head no, a blush already spreading over my face. Then she opened her other hand offering me a tampon instead. I took the pad, placing it in my panties as instructed. Of the two choices, the pad is definitely the lesser of two evils.

I pulled my panties back up and returned to the bed. I set on my side not knowing exactly what to do. I didn’t want to lay back down, possibly inviting another situation. I was still not used to her apartment, do I go to my room, just what is appropriate after being ravaged?

She brought me a nightie, slipped it over my head, then laid me back on the bed. She climbed over me, spooning me from behind, her arms pulling me tightly against her. A few minutes later I heard her relaxed breathing, she was sound asleep. I turned partially, being able to kiss her cheek, but barely. Then back to where I was as I contemplated what had happened today. Eventually, the day’s happenings caught up with me, and I slipped into dreamland too. It was late the next morning when I woke, Cassie had already left for work, leaving me a note and a spare key to her apartment.

She suggested a shower, washing my nether regions to remove the last vestiges of my sexual escapade. Even reading that as written causing a blush to spread over my face. The shower did feel good, I washed down there thoroughly, not wanting to smell any odors from my encounter. The note also suggested me dressing as complete as possible in my female persona and getting out for a bit, maybe the mall.

I did just that, very aware that I needed to be out and about as a female if I was going to pull this off. The more practice I had, the better my chances were of going undetected. I took a taxi to the salon to get my car then drove to the mall. Driving in heels is a new experience, I vowed to get some flats for driving, then change into the heels when I got to where I was going. I walked the mall from one end to the other, window shopping, watching other females and trying to imitate their movements.

I spent three hours there, even found a dress that I just had to have. I did not try it on, not near brave enough to do that yet. It was a sweater dress, the length looked long enough to satisfy the dress code, the neckline very code friendly. I know we sell something similar, but that will take quite some time before I am confident enough to shop in our own store. Maybe after working there for a while, but that is a definite maybe.

I was getting hungry, but did not want to risk my voice or mannerisms. Maybe with Cassie at my side. I made it back to Cassie’s, so far so good. I cleaned up a little, if I am going to be living here with her, I am going to do more than my fair share. There was no laundry yet, so I headed to the kitchen to see what she had for dinner. Lots of things for a salad, so I made one for each of us.

Looking through the cabinets I found some canned ham, deciding to broil some of it with a brown sugar coating in the oven set low, for at least an hour. That would allow the sugar to seep into the ham, instead of just coating the surface. I found ingredients for a ranch dressing and made my own, something I normally did for myself anyway.

I set the table, then made some tea, a deep and rich black tea seeped slowly so the full flavor of the tea would come out. I returned upstairs and changed my outfit, playing around with my makeup some. Since most of it was stains, only lip gloss and mascara were required. I did alright this morning, but barely sufficient, especially for a fashionable female. Let’s just say that there was mascara where it didn’t belong, and the lip gloss was on more than just my lips. A male dies not realize how hard it is to stay between the lines when applying makeup. I had to redo my lip gloss twice and even after I had applied the mascara I had blotches instead of even coated lashes. I heard her come in, her giggling, ‘I am home honey’, heard throughout the townhouse.

She was ecstatic about dinner, her salad disappearing long before mine. She asked what brand dressing was served tonight. When I told her I made it, she came over to my side of the table, put her hands on either side of my face and laid a long one on me. I was breathless as she released my head. After the month, you are not going anywhere, we are getting married and you are stuck with me for eternity. She wanted me in bed, but I wanted to clean and straighten the kitchen before we left. She reluctantly agreed, but I could see a small smile hidden in there somewhere. Maybe she was envisioning me as the perfect little housewife. I knew better than to guess what runs through her mind though.

The next few days were a repeat of today. Off to do some shopping and observe who I was to imitate. The second day, I served hamburgers. A full half pound burger on bakery rolls fresh from the bakery this morning. I broiled the hamburgers in the oven, loaded with spices, a little Worchester sauce and chopped up onions and peppers mixed in with the meat. Slow broiled so the flavors could blend, and then turned once to insure an even brown. I had an assortment of toppings ready to be devoured, and added the cheese slice when she walked in the door. The fries had been kept warm in a crock bowl, nicely brown and ready to be dipped in ketchup or mayonnaise.

Cassie said it smelled so good so I would get my kiss now. I was laid back and deep throated, her tongue was wicked and quite capable of amazing things. Again, leaving me breathless and woozy, she sure knows how to ring my bells. She made me sit on her lap as we ate, taking turns feeding each other. It was a thoroughly enjoyable meal. I again cleaned up, she just parked herself on a bar stool watching me. She did assist me as I worked, every time I passed by she would grab me, kiss me and pinch my ass before I was allowed to continue. It took much longer than usual to get the kitchen straightened up, believe me.

The next day again around town, the mall and even back to the salon. I had been reading all of her fashion magazines at home, and convinced myself that I needed a newer trendier hair style for work. When I checked at reception I could get a stylist in an hour that gave me time to browse the hair style books looking for the perfect curly do. I found one that would work with my hair length, the end result would be tussled curls framing my face, with longer tendrils at the neck. The tech saw the picture of what I wanted and then shampooed my hair adding a straightener to offset the setting lotion used last time.

This time I got one of their permanents, another one of their discoveries. Regular permanent rods were used, the paper the hair was wrapped in more of a silk material. Each curl was wrapped tight, then saturated with the permanent solution. Under a dryer for over two hours, the heat turned down low. No neutralizer needed for this type of perm, when the permanent rods were removed soft curls exploded from the rod. The texture of the curl was silky like the material used to wrap the hair with.

For dinner that night I made spaghetti and meatballs. I made the sauce myself, slow cooking it with lots of spices. I used canned tomatoes, but not sauce, cooking it down until I had the desired consistency for the spaghetti. I rolled the meatballs and broiled them with spices, onions, peppers, and garlic mixed in the meat mixture. I had the broiler on low, so the meat would cook slowly allowing the flavors to mix. Turned over several times to insure an even brownness. The spaghetti boiled in water with some oil and spices added to enhance the flavor. I drained the water off and mixed the sauce in with the spaghetti. The meatballs were added on top, so they were not soaked in the sauce. Of course, I did some garlic bread, five grain bread, with butter and garlic added then under the broiler for a few minutes.

I am home honey, was heard as the door closed and then I was ravaged as I was trying to get the garlic bread on a plate. She took her fork grabbed a meatball, moaning and groaning as it was consumed. Then I was dragged to the table for another session of feeding each other. When we finished she pulled me even closer, hugging me very tightly. Her next words surprised me.

“Why don’t we get married this weekend, I love everything about you, you make me so happy and I want you in my bed forever more. If necessary I will get a second job so you don’t have to work, I want to come home to you, to ravage you and to treasure you from now on.” Then I saw her take a box from the end of the table, opening it and taking the ring inside and sliding it on my finger. She looked up into my eyes and gave me her puppy dog look. “Pleaseeeeeeeeeeeee.”

I told her yes, but I need time to get used to the new sex. “I presume you want the Millicent and not the male from before. Let’s work through the four week dress code test and then we will make some plans. I do love you and want to take care of you so much. One thing though you have to have the kid, I will be a mother, but you have to do your part, dear.” Further words were impossible as someone’s tongue was half way down my throat. I never got an answer about her doing her part.

I had one more day to roam as a female, then take care of my hubby. That is why the name hubby/Cassie was given to her. She didn’t care, as long as I was on the other end of the greeting she was happy. I was planning to serve the remainder of the spaghetti and meatballs, but when I looked in the refrigerator they were not to be found. I looked instead in the sink, finding the container I put them in last night there surprisingly empty. Cassie again, if this keeps up I will have to get us both signed up at a gym or neither one of us will fit in our clothes. Cassie will definitely have a head start in that regard though.

So not having much time before she got home I did the wifely thing and ordered some pizza. I did rummage through the refrigerator looking for some additional toppings that could be added to enhance the flavor. I found some cheeses, some peppers, and some sausage that will suffice. From her meager pantry I found some canned olives, slicing them up ready to be applied when the pizza got here. The delivery guy got here a few moments before Cassie, I paid him then added the extra ingredients and slipped it back into the oven.

Honey I am home came from the front door as the timer went off on the oven. I moved the pizza to the table, adding some iced tea to our glasses. I got kissed, something I found I was looking forward too now. She saw the delivery box and looked disappointed then I asked her where the spaghetti and meatballs disappeared to. She smiled, and rubbed her tummy, giggling a little as she did so. I had two slices of the pizza, she finished the rest off herself, splitting it between now and another late evening snack.

We spent the weekend enjoying each other, my nipples were very hard and sore come Monday morning. Of course, I gave as good as I received, I am sure her nipples were also well worked over as she donned her bra. I dressed in one of the outfits I picked out from the salon store, fluffed up my hair and added a coat of lip gloss. We each drove our own car to work, our schedules were similar, but she got off two hours earlier than I did. At least this first week I was working five ten hour days, having Wednesday off and having to work Saturday. I expected that since it was normally the store’s busiest business day.

My boss in cosmetics checked my appearance, even finding where I had not worn the appropriate earrings as per the dress code. I had to go to the jewelry department and purchase a pair that complied with the new dress code. I became painfully aware that I would not be shown any favoritism in this one month trial. I was not allowed to sign in to the computer until I had complied with the dress code, so I would be working an extra twenty minutes tonight before I could leave the store.

By lunch my feet were killing me, the heels just too much. I did get to eat lunch in the store restaurant, one of the other sales associates seeing me rubbing my feet suggested that I get another different pair of heels, sometimes just wearing a different shoe would ease the pain of higher heels. So I went to the shoe department and purchased another pair of four inch heels, this time a block type of heel with an open toe.

When I got back to the cosmetic department I was late, now another thirty minutes tonight to make up the time. I was also written up for not having polish on my toes, since the new shoe was open toed. That would require another hour later in the week to work off the faux paux. I did sell quite a bit of cosmetics, even received a couple of compliments from customers.

So a little after seven I managed to make my way out of the store. I headed to Cassie’s place, parked in her garage and walked into her kitchen, my heels in my hands. I caught my stockings on the door frame, sending a large run right up the stocking. That was it, I set down on the floor and started crying, everything today just adding to make my life miserable. That is where Cassie found me. I was helped up and taken to my room. She helped me out of my clothes and laid me back on the bed, then crawled in next to me and held me tight.

That is where I found myself later, my need for the bathroom forcing me to leave her loving arms. When I got back she was sitting there, some fruit in a bowl in one hand and a large glass of iced tea in the other. I was hand fed, then when all the fruit was gone she helped me into a nightie, one that I do not remember buying. The covers were pulled over me and a passionate kiss on the lips was delivered. She then resumed her cuddle, holding me tighter this time.

The alarm the next morning meant I had to leave her arms again, I had to try and get to the salon before work to get my toenails polished so I would not get another write-up. Breakfast was a long lingering kiss from Cassie, then I had to get going. The salon could work me in, thirty minutes later I was heading to the store. I was checked closer this morning, by the department head, every inch of my appearance was gone over carefully.

I became aware that I would get by with nothing during this month, two days into this week and I was already written up twice. Yes, another write up today, my skirt was not the proper length, it being at my knees and the dress code requiring at least four inches above the knees. It was one of the new outfits, but I had not tried it on, the skirt longer than I anticipated. No extra time for this deficiency, but a copy of the write up placed in my employee file. I am sure when Jennifer sees the reprimand she will have a good laugh.

Unfortunately for me, it was much more than a laugh at my expense. I was called into her office before I started work the next day. She had me close the door behind me, not a good sign that the meeting might be favorable to me. She asked about the write-ups, and what I was planning to do make sure there were no more. One more reprimand and I would be formally warned by personnel of rules violations. Three more and I would be let go. Since I had written the dress code she did not expect me to violate some of the guidelines. I tried to defend myself, saying that the department manager was being extra critical.

She reminded me that it was clearly stated in prior meetings that all my managers would do so, so that should not be a surprise. We thought we could start a higher level with you since you were aware of all the rules and policies. You do remember writing the new dress code don’t you? That assumption apparently is a mistake.

So starting tomorrow you will attend the new employee classes one hour every work day before you go to your previously assigned department. That will extend your time as a female, now you can count on spending three months before the trial period is over. Maybe the extra time learning what you should have already been aware of will stop the write ups that you are accumulating. I will notify all the parties involved of my decision, now go to cosmetics and do your job. Tomorrow you will attend the first new employee class, and then every work day thereafter for the required thirty classes. I want perfect attendance and I want you to behave, if I hear otherwise I will make the necessary corrections to your behavior. Now get to work.

I made my way down to cosmetics, this was not starting like I hoped. To be sent to the new employee classes, a definite slap on the wrist for my behavior. I don’t blame Jennifer, she is just reacting to what I have done. The problem is I have no idea why I have made the mistakes, I do know the dress code backwards and forwards, but the hem length of my dress totally escaped my mind that day. When I looked in the mirror that morning, I didn’t even look at the hem of my skirt.

I did manage to make it through the day, without out any more write-ups. As I drove home after work I was seriously depressed. None of this was going like it should, it was like I was sabotaging myself. After the first meeting with Jennifer and the CEO it seems I have managed to do a pretty good job of it, I am definitely my worst enemy. When I got to Cassie’s I went right to my bedroom, got undressed and pulled on a nightie. I crawled under the covers and closed my eyes, hoping that somehow all of this will end. That is where Cassie found me, since she was also in pajamas she just scooted me over and cuddled me. I don’t remember a thing after that.

I had to get up earlier, attending that new employee class was going to be sheer torture. I dressed carefully, checking myself often to make sure all of my clothes were dress code friendly. I drove to the store, then made my way to the classroom on the third floor of the store. That is where the executive offices are housed, with the store on the first two floors of the building. Believe it or not my appearance was checked carefully, then the instructor wrote me out another violation. My lipstick was not applied properly, plus a color that was prohibited in the store. I was told that a coat of gloss was necessary after the lipstick application as per the dress code, section 1 paragraph 5. I had to sign the write-up and then sit through the one hour class. After the class, instead of heading down to cosmetics I was sent to personnel. When I knocked on Jennifer’s door, she called me in asking me to close the door behind me.

Oh gawd, another black mark, I doubt I will be out of female clothes in this century, if I am even still with the company after today. She looked at the write-up, than at me. I had to look away, I was so embarrassed at what had happened. I had wrongfully presumed that I could change my lipstick before I went to the sales floor, it was just a class away from any of our customers. Then I remembered that the dress code is in effect when any employee is within the store or offices. Some help that was, maybe remembering before I get caught might have been a better idea.

Jennifer did not say anything, I am sure she is pissed at my behavior, her faith in me as her assistant quickly vanishing. I finally received a few words from her, given a card for the salon with a day and time written on it. “Since you have shown us nothing of your past behavior and knowledge I am having the company pay for some more permanent changes so that you can still remain employed here. Since we all agreed to try this I feel partly responsible for your transformation hence the appointment to make the changes more lasting.”

“You no longer work in personnel, your time there was obviously a big mistake, since you have seemed to learn nothing from your time spent there. I doubt you can handle a job much more complicated than a sales associate. There is an opening in ladies wear where you will be assigned. You still need to attend the new employee classes, maybe something will sink in. If you refuse this last attempt at keeping you employed, you will walk away with nothing, your services will no longer be needed.”

I tried to say something to her, but she pointed to the door and I walked out. It was like my whole world came crashing down around me, nothing seemed to work, everything I did was wrong and picked upon. I doubt any employee of the company has received four write-ups in less than a week. I made it down to cosmetics, after checking my appearance in the rest room. I made sure I was dress code complaint, even checking twice on a couple of things. The really hard part was trying to keep from crying, I knew if I allowed myself to start I would be sobbing within minutes.

When I got there, the department head told me I had already been transferred to ladies wear, so I needed to report there. I was few minutes late since I had to walk from cosmetics to ladies wear. Luckily that was not noted by my new boss. She showed me around and instructed me on my job for the first few days. That was to hang up all the clothes that had been tried on and left, then hang up the new arrivals. It was a tedious job, very hard on the feet, my heels making my feet ache all the way up my leg. I worked through lunch, trying to make up the time I was not in the department earlier.

I did manage to get everything hung before it was my time to leave a major feat in itself. Although the job was boring and repetitive, it wasn’t but a couple of hours later that I was holding things I liked against me to see what I looked like. I knew it would be awhile before I could afford any of the items on my new pay rate. If Cassie doesn’t let me stay with her, there is no way I can afford my apartment on my new pay rate. I need to check on that, and somehow end my lease on my old apartment before I end up owing more than I can possibly pay back.

When I entered Cassie’s apartment she was standing there with hands on her hips. Oh shit, more trouble. I decided to start crying right away and beat everybody to it. Believe me it was only a minute with her staring at me and I was sobbing. I was taken by the hand and led to the living room and seated on the couch. She left to get us something to drink, then returned and sat right next to me. I was handed my drink, then through waves of tears sliding down my cheeks I told her everything. I was comforted some, but even she was withholding her affections some. Of course my mind started working overtime, she was going to kick me out leaving me in a low paying job, an apartment I can’t afford and without anyone to comfort me and love me. I was surprised at the last part of that, love me, a phrase never used in connection with my name ever. Well, my new name.

She pulled back some away from me, my heart almost stopping. Oh gawd not now, please not now. She made me face her, even holding my head some so I had to look at her. “Now you know what a female goes through every day. Will she do okay at her job, will her appearance be satisfactory, her appearance so much more important than a male’s look. Will she meet someone to help her get through life or will she be single and lonely forever. Will her new boss be supportive or will they just find more things wrong with what she does. Now add in a young male’s changes to the dress code, making life even more difficult for her. I think you are beginning to see what it is like to be on the other side.”

“You need to forget the past, you are just a female trying to make a living in this cold hard world. Do the best that you can at what you are assigned, forget the dress code and live the female life enthusiastically. You are a lowly sales associate in women’s wear, a starting point for you. Learn from the new employee classes, something new during each class. Apply it to your job and maybe just maybe you can come out of this on top.

I will wait patiently for what is buried deep inside of you for a few weeks, then if you continue on your self-destruction we will have to part. I still have feelings for you, but can’t see you throwing everything away for something that you think you want. Now we are going to fix dinner together, eat it and clean the kitchen then we are going to cuddle on the couch until you get sleepy. Tomorrow is a big day for you, you need your beauty sleep then I will tuck you in and give you a kiss on the cheek. No more delicious kisses until you face reality and your future.

It was after I ended up in bed before all she had told me finally sunk in. I guess I was living a dream, a male’s dream, thinking that I was better than everybody, put on some female clothes spend a month doing that and then return to my job as if nothing happened.

Well it all got knocked out of me, now I am a sales associate, with no immediate future. Not enough pay to sustain my former life, and on probation with someone that cares for me. I made several decisions that night, the first canceling my lease on my old apartment. I debated about picking up my male clothes, but really didn’t have the time or resources to get them to Cassie’s apartment. I figured I could clean the apartment on Sunday, my day off, throwing out my male things, only a few kitchen things making the trip to Cassie’s apartment.

To my utter delight Cassie came with me, making the job go twice as fast. A neighbor at the apartment complex, took my male clothes, thus after we finished cleaning two boxes of kitchen items is all we brought back to the apartment. As I thought about it later, I could have dressed again as a male and got another job in town as one, maybe escaping some of this. It never occurred to me, I knew if I could make it through the next few months I would have a job here, even though it was as a female. The pay also never really entered my mind, I think sub-consciously being with Cassie was what was steering my decisions.

I prepared for work every day with considerable effort. I checked my hem, the amount of cleavage showing, my jewelry, nails and my shoes before I ever left the bedroom. On Saturday night I was thrilled, a whole week with no infractions against my name. All during the week I applied myself enthusiastically to every job I was assigned. Later in the week I was handling customers for the first time showing them where they could find what they were asking for plus other possible combinations that they could coordinate with their selections.

I did see Jennifer around some, she was cordial to me but not overly friendly. One of her secretaries got promoted to my old position, they did make some changes in the dress code I had written making all concerned happy. Over the next few weeks I worked my way up in ladies wear, now the assistant department manager. My sales figures were always top notched, even surpassing the department manager during most weeks. Then three months after my assignment to the ladies wear department I was called to the executive offices, specifically the CEO’s office.

As I entered the office, I noticed who was waiting for me. Jennifer sitting to the side of the desk, the CEO behind the desk and Cassie to the other side of the desk. This can’t be good for me. I was told to sit in the chair in front of the desk and a huge file on the CEO’s desk was opened. I presume it is my file. Every item in it was gone over by the three ladies, even Cassie getting involved in some of the discussions. I wasn’t really ridiculed just reminded of every instance and what had happened. Then Sharon the CEO asked what should be done with me.

All she received from me in response was Huh. Jennifer suggested that I might be used to fill the ladies wear department manager position that is soon to be vacant. The other two vetoed that proposal. Then Cassie suggested that maybe I could be utilized back in personnel, Millie has learned a lot since she was assigned there last time. Jennifer and Sharon said no, rather emphatically. I was almost in tears, nothing showing yet, but right on the verge. Sharon cleared her throat, looked over at Cassie, saying it is all up to you. Whatever you decide that will be fine with us. I looked over at Cassie, a look of hope on my face.

Wait a minute, what has Cassie got to do with my future here at work? I stared at her, trying to figure out what is going on here. I started to get up from my chair, maybe I need to get some fresh air.

“Millicent you need to sit back down and listen. Do you know my last name?” I shook my head no as I sat back down. “It is Henley, does that have any significance with you? Again another head shake no. Then it dawned on me the company name is Henley’s, that can’t be. Is she the daughter of the founder, known throughout the company as C. Henley? I stayed with her, I kissed her, cuddled with her, oh gawd how dumb can I be? Don’t answer that.

Cassie smiled at my realization, then spoke of where I will be working now. “I think I will have Millicent working in purchasing for a while. Hopefully she has learned what sells and what items we need more of. Then when she has placed her orders she can be my executive assistant, handling all matters that pertain to company operations. When Sharon retires later in the year she can be the new CEO. I will personally see that she complies with the company dress code. We have had trouble with her in the past on that same topic.” Does anybody here have any objections to that line of thinking? Jennifer and Sharon were quiet, but I raised my hand. Cassie looked at me, put down that hand Millicent, your opinion does not count.

Everybody got up and left, Cassie taking my hand and dragging me after her. Through a door, and into an even more lush office. I was pushed up on her desk, laid back and kissed like never before. I put my arms up around her neck and pulled tight, not ever wanting to let Cassie get away.

It turned out the whole mess was staged to get me experience in areas I had no knowledge of. The write-ups even to make me feel like one of the lowly sales associates to experience some of the things they go through and are subjected to every day. Cassie was the mastermind behind most of it, but I understand Jennifer had quite a bit of influence in things. I did progress, eventually taking over for Sharon when she retired. A year later Cassie and I married, it is a family owned business you know.

I never forgot that dress code, often going back and re-living some of the things I experienced. Yep, living the dress code was a very fortunate occurrence in my life. It did change me in other ways too. I remained committed to the dress code, still do adhere to it explicitly. How can you require your employees to dress accordingly when the boss doesn’t, besides I feel so uncomfortable in male clothes anymore.

The final reason for dressing as a female is that Cassie would have me committed if I appeared dressed as anything else. I have easily adjusted to that line of thinking, gorgeous clothes, beautiful lingerie and the love of my soulmate, what more could a gurl like me want?

© 2016 thru 2024 by Francesca