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 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 himsef.
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, fed 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 won 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 cost so that the color does not bleed through to my new nail. Then three coats of polish, a bright pink in color and very strong on the bright. 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 what 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 shelved 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.
The shower is fantastic the next morning, but I found myself more than once standing on my tip toes to be able to stand without some discomfort. Apparently my calves had grown accustomed to the heels somewhat and the lack of support made them scream their disfavor. I wonder how long it would be after the contest before I could walk normally without heels on.
I did remember to dress first before slipping into the shoes, last’s night scramble to remove my pants not something I wanted to revisit. The shoes felt good as my feet slipped into them, a surprise to me. I wore the same ones as yesterday, trying to get comfortable wearing them so I could be even more comfortable in shorter 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.
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 with no makeup whatsoever 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. 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 escapes 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 ask for 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 hear 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, and 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 employee 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 occurence. 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.
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 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 them. 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.
Story Complete For Now
© 2016 thru 2021 Fran Cesca Walker