Carey; Well Heeled

Another week successfully completed, in a few hours I can head home and enjoy some peace and quiet in my little corner of the desert. Well hopefully for at least two days. Of course, then the grind starts all over again, five days of my job and the commute that goes along with it. My little corner of the desert is quite a ways from our offices, requiring a daily commute of almost fifty miles. In my opinion the commute is well worth it since the views, are spectacular from my front porch. It is located in the foothills surrounding Phoenix, my view of the Valley of the Sun is breathtaking.

I found my little piece of heaven at an estate auction, very few bidders on the property mainly because the photos of the property were so poorly done. I got it for a song, well under the assessed valuation. I did have to spend a little to repair some things, but after a few months I was quite happy with my new abode.

I work for a ladies shoe manufacturer doing up their ads for different media. The home office is located here in the Arizona desert, but all the shoes come from our three factories in the Far East. Our main warehouse is over eighty thousand square feet, with boxes of shoes stacked four feet high on tiered warehouse shelving. The shoes come to us in trailers, that have been stacked on boats for the trip to the states.

After my ads have secured a sale the orders are shipped from our warehouse to individual customers that order off the internet. We also sell to other retailers. The shoes that are wholesaled are different from what we offer online, although shipped from the same warehouse.

My job is to keep the customers coming to our website. That is done with advertising in magazines, some TV ads and in pop up ads on the internet when someone types in shoes for an internet search. I usually have over five hundred different ads appearing somewhere over a period of a month. We have been quite successful in our endeavors, the sales steadily increasing over the last nine months. That happens to correspond with how long I have been in my current position. I try hard and work diligently at improving as I go along, but have also been very fortunate.

I seldom use sale pricing to sell the product, instead I use suggestive ads showing the shoe with different fashions where the shoe looked perfect for the outfit or occasion. Our shoes are reasonably priced, placing them within reach of most any female, but not sacrificing quality in the meantime. We also offer more expensive heels, but they are made of premium materials like leather, that is real leather not imitation or inferior grades of the material.

I get a call from the CEO asking me to stop by her office on the way out of the building. Sheila Bankcroft is a gem of a boss, easy to work for and makes sure hard work by her employees is properly rewarded. I have received three raises since I started, not huge but still a significant reward for what I have managed to accomplish for the company.

I knocked on her door, it is a little after four PM, our workday usually starting at seven AM and ending at four. She calls me in and I sit in the chair in front of her desk. There are four boxes of high heels on her desk, the style not ones that I am familiar with. She takes out one of the heels and hands it to me asking me what I think of it.

“It looks pretty, the heel is quite attractive but awfully thin and slender. I like the low profile of the top of the shoe letting most of the foot show. In the past shoes with that low profile have sold well. The heel may be a problem, it looks to be at least five inches tall, making it a little harder to promote, most females know how hard it is to wear a shoe with this extreme heel height all day. The shoe seems larger than any shoe we have offered, is this a size ten, or maybe even larger? In our sales experience, a size ten or larger shoe does not sell that well, usually only a couple of hundred sales on a specific style.” I smiled, she did ask me my opinion of the shoe.

I put the shoe down on her desk and waited for her response to my thoughts. I was wondering why she was contemplating trying to sell a shoe obviously outside our normal range of success. In the past we have kept to the features that have sold well, leaving out of the norm features for others to deal with.

“We are trying something totally different for us. This design and the other three are part of a test we are conducting to see if we can market and sell heels to members of the male sex. There are other companies already selling to this group, some of them doing quite well so far. The interest is there, but we have yet to determine if is enough to make it feasible.

The sizes we offer are more along the lines for the normal male foot, leaving out any shoe size larger than a male twelve shoe. I know I am asking a lot of you, but would you take these home with you this weekend and wear them some letting me know on Monday your honest opinion of the shoe and your thoughts on selling them. I have included stockings and something to hold them up, a necessity when wearing heels. Take your time when you first slip into the heel, I don’t want to have to visit you in the hospital with a broken ankle. I would normally offer to be with you when you first try them on, but figured you might be more than a little embarrassed so thought this might be best. Please try them for me, we have already invested quite a bit of time in developing this idea and want to give it a fair chance.”

I nodded my head in affirmation, but had not really thought out what I was agreeing to do. The shoes were put in one of our designer shopping bags, our logo proudly displayed on the side of the bag. Then another bag was handed to me, containing my stockings and lingerie needed for my exploration this weekend. Sheila asked if she could call Saturday evening, to get some of my initial thoughts on trying the heels. I nodded, then walking in a daze made my way to the parking lot and my car. I wondered why I had been chosen to test drive the heels, surely some of the people developing the idea would have already done so.

On the way home I decided on some tacos, figuring as scatter brained as I was at the moment I might end up burning my house down if I tried to cook something tonight. That turned out to be a good idea since I drove away from the drive thru window without getting my change and tacos, an employee having to bring my food and change out to my car. I did remember where I lived and did manage to eventually get home sometime later.

I consumed the tacos, drank some green tea I had made earlier and put in the refrigerator and got comfortable on my couch. The couch was one of those big comfy things that went out decor wise ten years ago. Over half the time I would end up falling asleep there instead of my bed. I leaned back just trying to get comfortable.

I tried to figure out how I was going to tackle this intrusion on my peaceful weekend, eventually deciding it shouldn’t be that big of a deal. I remembered my sister wearing heels and stockings always complaining about leg hair and the need for it to be removed before wearing stockings. So I guess that will be my first activity with my shower in the morning.

Then a smile appeared thinking of sending a selfie of myself to my sister, asking her if she liked my new heels. Then a second one a little later asking her if these are maybe a better choice for work on Monday. Yep, this crazy scenario might be fun, at least, for a few hours.

Sis and I always enjoyed winding each other up, our pranks and conversations almost legendary among sibling rivalry. This one might be the best yet, I might need to thank Sheila for the opportunity come Monday. With my belly full a few yawns later I succumbed to Mr. Sandman, the last thing I recalled from my dreams was slipping into my heels, right after dressing in my LBD for an evening out.

I awoke with that thought still in my mind, maybe eating tacos right before bed is not that great of an idea. It took me a few moments to realize I was laying on the couch and that the thought was just part of a dream, a very vivid and disturbing dream. I made my way to the bathroom, did my business and then climbed into the shower, with an old shaver and a can of shaving cream. As the first burst of cold water hit my body I remembered I had sat down to pee, a first for me. I shook my head, trying to dislodge that thought. Too late it had already found a spot to reside, but never far from being remembered easily.

I ended up using all of my hot water, shaving my legs was not as easy as it sounded. I was extremely lucky that I had managed to not shed any blood in the process. As I emerged I noticed I had also shaved my chest, not having the slightest idea why that was done. Weird, maybe some feminine spirit had possessed my body during the night. With very little hair elsewhere, my body now actually resembled my sister’s some.

Dried with a towel, I made my way to the bedroom, and laid out all of my goodies from the bags that Sheila provided. Of course, the four pair of heels, then three pair of stockings and a garter belt. I knew what garter belts looked like, several of my dates with females in the past had worn them, although not as fancy as this one. I can picture Sheila giggling as she picked out the frilliest one we offered and slipped it into my bag. The next two items did surprise me though. A mini skirt and a short slip to be worn with it. I imagine the giggling when she added these was soon full blown laughter as she slipped them into my bag.

A few months ago we had partnered with a couple of clothing retailers selling their product along with ours on the internet, then shipping it from our warehouse. A profitable partnership for both of us. It was not a big portion of our sales, but seemed to be a frequent add-on for a lot our customers

Oh well, now for the hard part. I hooked the garter belt around me then slide it around until the label was in the back. This one had eight garters hanging down to be attached to the stockings. It was done automatically, almost as if my female spirit was possessing me now. I remembered sis rolling up the stocking before sliding her toe into the stocking, so I repeated that action. As I unrolled the stocking I was overwhelmed with feelings, like a million goose pimples trying to rise to the surface all at once. Once unrolled on my smooth hair free leg, I attached it to the garters having to contort my body some to get the back garters fastened. Before I could process any more thoughts I did the other stocking the same way. As I stood up the stockings rubbing against each other felt wonderful, now it seemed like two million goose pimples were suddenly attacking my body.

I wondered what to do about underwear, then I noticed a pair of panties that had attached themselves to the slip by static electricity. I couldn’t see wearing boxers or my tighty whities with stockings and a garter belt so I succumbed to the lure of the panties and slid them up my legs. Oh gawd, what wonderful feelings they made as they slid against the stockings. I quickly reached for the heels, thinking that putting them on might distract me from the silky feelings that were assaulting my body, mainly my male apparatus.

I managed to get my feet in them, my size nine male shoe size a perfect size eleven in women’s sizes. I did wonder how Sheila knew my shoe size, I don’t remember ever discussing what size shoe I wore. The height of the arch with the five inch heel made itself known very quickly, surprisingly I enjoyed the new found feel of the shoe and the height that it added to my five eight male presence. I was cautious in standing, dressed like this I did not want to fall and break anything, wondering how I would explain how I was dressed to anyone finding me.

I took a few tentative steps, making sure to take shorter steps and walk along an imaginary line on the floor. I am not even sure where I read that about walking in heels, but the information was correct. I made the circuit of the bedroom several times, took my time and was doing quite well after a half hour in the heels. For some reason I decided a picture sent to my sister would be appropriate now, the previous thought of her receiving such a picture tickling my imagination.

I took several selfies with my phone, picked the sexiest one and hit send. The attached text asked if she liked my choice in heels? Do you think it will go with my miniskirt? In less than ten minutes she called, wanting an explanation of why her brother was looking better in heels than she did. I was vague, having way too much fun teasing her making her answer my question. Well that approach may have backfired a little as she told me to stay put she was on the way to my house. The click as she hung up on me left me at a distinct disadvantage.

Since she lived not far from me, actually at the base of the foothills, in less than a half an hour she let herself in and was searching for me. I thought sliding the miniskirt on might add to the illusion so I was doing so as she walked into the bedroom. I heard a squeal, then I was pulled into a tight hug right after she had checked out my attire. She was brazen in her efforts, raising my skirt to see what I was wearing underneath. Sisters can be so pushy. Of course, this was not what I was expecting my face and neck as red as a fire truck.

After the hug and another look at my heels and stockings, I was dragged to the kitchen where all important talks were conducted. Her hand rubbing up and down on the stockings not doing me any good in getting the red out of my upper body. I was made to sit on one of the bar stools, although I have chairs too that were of a more normal height for sitting. I had to be careful, my skirt and slip made staying atop the bar stool quite a bit more difficult. The slipperiness of the plastic covered seat was frustrating since no matter what I did I was constantly trying to keep from sliding off.

So here I was perched on a bar stool, my bottom half as girly as possible and my top naked as the day I was born. Sis would have none of that and went rummaging around in my bedroom. She returned with a top that she must have left here at one time or another, and I was soon encased in its embrace. She also had one of the other boxes of shoes that were laying on my bed in her hand, so I held out my foot figuring she wanted this pair on me instead. Soon I was standing in the other pair of heels as she had me walk around some. The only comment I heard is you walk better in heels than I do.

So that is how I spent the morning, trying on each pair of heels and wearing them for awhile. I could tell sis was up to something, quieter than usual and often taking glances in my direction. Of course, my makeup and hairstyle was played with too, any chance for a devious sister to have fun at my expense could not be passed up. The glances were more like stares, as her eyes penetrated deep into my new feminine image. She did some things with her purse, then suggested we take a short walk down the street. I should have been alerted when she took her purse when we left the house.

I pretty much live at the end of a street, no inhabitants past me so they never finished paving the street. There were several small trails that led off into the surrounding desert, mostly untouched since the cactus and native flora had overgrown the small trails. Once out of the house I turned to see sis locking my front door with my set of keys. A huge smile on her face as she led me directly to her car. Get in we need to do some shopping for you, then maybe lunch out and maybe a movie this afternoon. I started to protest, but she just opened her purse and let the keys drop in. She pointed to the passenger door, and so I opened it and carefully seated my touche on the seat. She has been known to be as hard headed as me, so fighting her on this was probably futile. Besides I was locked out now, my keys to the house in her purse. Then you have to realize I was anything but confident being dressed as feminine as I was and out in the cruel world for the first time.

The rest of the morning and early afternoon was spent shopping for clothes for me. I whined and tried to impress on her that I was just wearing the shoes as a trial to see how comfortable they were and get an opinion on them for Sheila come Monday. If you have a sister as focused as mine, you know I was not going to dissuade her from her goal. Finally back to her car both of our arms loaded with bags from some of the ritziest boutiques in town. I was also fifteen hundred dollars poorer. Somehow as she was planning this, she had snatched my credit card from my wallet, providing it when my purchases were rung up. Sis always shopped at the better boutiques. Of course, her preference in stores translated to her looking quite beautiful at all times, chic and sophisticated to be specific. I was hoping just because we shopped at her boutiques my look would not be as fashionable as hers.

We stopped for a late lunch, a measly little salad all I received for three hours of traipsing through boutique after boutique and trying on over thirty possible purchases. We had chosen to eat at one of the mall restaurants and were headed to the movie theater when we ran into the only person I really did not want to run into dressed as I was. Sheila almost did not recognize me, but karma is cruel. Of course, she had to see some of my purchases so rather than a movie we headed back to my place for an impromptu fashion show for Sheila. Believe me it was sis’s idea not mine, to try on all the clothes again so that I could show my boss how good I looked wearing them just seemed idiotic. I did try them all on for her, even pretended to walk the runway as I was doing it. It is amazing what a dumb male will do when his sister is goading him on and his brain has stepped out for a lengthy break. Well, it may have left its confines for an extended time, instead of just stepping out, judging by what happened.

After looking at my purchases she offered to pay for all of them, they would be perfect for the ad campaign for the heels. She thanked me for stepping up to be featured in the campaign, promising to make it worthwhile for me later after the ads started running. I gave my sister a death stare, now because of her actions I will be dressed as a female often and no telling for how long. Maybe on Monday away from my interfering sister I can talk Sheila into using someone else for the ads. From Sheila’s reaction at the mall, I realized that notion had very little possibility of success.

Sure enough on Monday by the time I had made it to work everything had changed for me and not for the better. I did not make it by seven like I usually do, the clothes I was told to wear today not cooperating at all. I had to put on stockings, a blouse that buttoned up the back and somehow get myself stuffed in an impossibly tight skirt. I realized as I walked to my car, that even my walk was feminine now. Considering I was wearing five inch heels and the skirt was tight around my thighs I am amazed I could even walk much less swing my butt wildly from side to side. At least that was how it felt, my butt undulating from side to side as I meandered along. I assumed it will never be anything but meandering along now, the clothes and heels preventing anything resembling a normal male stride.

As I entered my office, everything was changed. Two new bookshelves loaded with shoes presumably for the new line of heels for males, my inspiration for me to glance at when needed. There were fresh flowers everywhere, my sports posters were gone, now pictures of gorgeous females in heels were in their place instead. The office walls now a pale pink color with burgundy trim at the doors. After I entered I had to stop and look twice to make sure I was in the right office. Somehow Sheila had accomplished all of this on Sunday, no telling what she had to spend and who she had to bribe to accomplish this feat.

Then before I could get comfortable behind my desk she told me the photographer was waiting, wanting to take a bunch of pictures of me in the heels to help spur some creativity for me on possible ads. This was done regularly, just not with me as the model. As I was planning my ads I would look at the pictures taken, picking selected ones or parts there of to use in an ad. Now the pictures of these new styles and sizes will all feature me as the model.

Five long hours later, I finally made it back to my office, my calves in severe pain from the constant wearing of the tall heels. Shelia had managed to find plenty of new outfits for me to change into as I modeled each new style of heel, all from the clothing companies we partnered with. I was mentally drained as I made my way back to my office, only to be apprehended by Sheila for a late lunch. I tried to dissuade her, telling her I was not hungry. Didn’t work as we were soon pulling up to a restaurant a few miles from our offices. They had valet parking so my door was opened for me and I was helped out of the car. I shook my head as we were escorted into the lobby and then seated in one of the nicer tables in a side room. I let out a sigh, as I was seated in my chair that the Maitre D was holding for me. My calves so needed to be able to rest for awhile. Sheila ordered for me, not wanting me to get my usual fare, since I now will have to watch my figure closer.

I was still in the last outfit I had tried on for the photo shoot, a classic dress that hugged my body very closely. Even though I had no breasts, the dress suggested there was something there. Of course, the skirt was keeping my thighs tightly together. An okay position, I guess, but one that I was not used to yet.

Sheila started off the conversation with the news that out clothing partners were thrilled with the pictures and wanted me to be the sole model for their clothing line. In fact, if we could pair their fashions with our heel ads they would increase our percentage of the sale of their clothing. I raised my eyebrow at the new percentage, a significant change for the better. As soon as we got back she wanted me to put together an ad and get it out among the places we advertised with. I groaned, this is mushrooming out of control leaving me with very few ways out of this scenario.

The salad was good, but being off my feet for the time it took to eat it was much better. Back to the office and I was led to my desk and told to get the ad ready as soon as possible. I worked on it for an hour, Sheila checking on me twice to see if I was done yet. I finally found one of the pictures that looked good, the clothes and the heels perfectly matched. Then I had to come up with some wordage to tie the picture in to a male wanting to wear heels. I decided to be just blunt, just a few words and as direct to the point as possible.

Why should your wife or girlfriend get all the enjoyment from wearing beautiful clothes and gorgeous heels. Feminine, you bet, but the sensations and feelings that come with wearing them so out of this world wonderful. You will never know what you are missing until you try it. I did and will never go back, my life so much richer because of it. Don’t let the female of the species get all of the enjoyment, equal rights now apply.

I decided on an internet ad, easiest to set up and quickest to run. I sent a copy of the ad to Sheila, hoping that she would approve and allow me more time to rest my weary feet. I straightened up my desk some, since it was piled with all manner of pictures and memos since I was out being photographed. It was a little over two hours later when a beaming Sheila entered my office. She had an email from the clothing partner praising the ad and stating that that item was now sold out until they could get more shipped in from overseas. Then she showed my the sales sheet from the heel that I wore in the picture, showing the same results. She has already ordered more of that style, to be air freighted to us over night.

Then the fantastic part, there were four requests from talk shows where they wanted me to be their guest. I pushed my chair back from my desk shaking my head violently, no this can’t be happening to me. Sheila came around and pulled me to my feet, hugging me tightly. The hug lasted for quite some time, such a good feeling. There were a few tears that got shed in the process giving me panda eyes . Sheila used a tissue to wipe off the mascara that had streaked down my cheeks, suggesting that I repair my makeup, being a spoke person for the company my appearance needed to be pristine at all times.

I told her I had no makeup with me, she made a call and soon I was being dropped off at a salon that she used frequently. She spoke to the receptionist and I was hustled away to one of their treatment rooms. The place was huge and so feminine. I felt more feminine just being in the salon. I was shown a bunch of papers authorizing treatments to be performed on me today. Although she told me about each one, my mind was elsewhere, so I just signed and soon I was naked and being worked on.

My eyes were open the entire time, but nothing that my eyes saw was being registered in my fuzzy mind. It was three hours later when I was helped back into my dress, with me noticing how much better it fit me. Of course, Sheila picked that moment to show up. With her grabbing my arm we walked by a huge mirror, I looked at the image of Sheila and I, almost fainting. My legs suddenly having difficulty holding my body up. Sheila put her arms around me and helped me the rest of the way to her car.

I now had breasts, significant ones and matching hips, with a narrow waist between the two. My face now much different, the thin eyebrows the first thing I noticed, followed by the pierced earrings in each ear. The makeup eliminated any remaining features that might be considered masculine, a gorgeous female all that was to be seen.

Once back at the office, Sheila dragged me to her office. I was handed a new schedule for me, each day planned in infinite detail. Monday and Thursday salon appointments at seven A.M. Then photo shoots for the rest of those days. The rest of the days work on ads, doing them so that only the wordage would have to be changed so that they could be used for either female or male customers. I started to point out that the male sizes were only in a few styles but her smile told me that she had already handled that problem. Now our entire line would be available up to a male size ten. The model for all the ads would be me, no discussion on that matter would be allowed. You are now making twice what you had been previously making, plus a five percent bonus of all sales.

She looked at me to see if I was going to protest and when no words escaped my mouth, she gave me a passionate kiss and suggested that I get my cute butt back to work. “You are having dinner with me tonight so pick something from the photo shoot and be ready at four. Oh, your sister is coming for lunch, so you might want to freshen your lipstick before then.”

I walked back to my office, still in a daze, probably a permanent one that I will have to endure for quite some time. As I entered my office my sister attacked me, hugging me and trying to see all of the changes since she saw me last. After a close inspection she hit me hard on the arm, while I looked at her wanting to know what that was for. “You are prettier than me now, and I am jealous. I will probably have to hit you several more times before lunch is over. This is so unfair, my brother looking better as a female than me.”

I did get hit several more times although not as hard. The lunch was alright but I had no idea what I consumed. All of my limited mind capacity still trying to figure out how I got roped into this and why I was not upset about it. By the time I got back to the office I had pretty much accepted what had happened to me, still not knowing why but probably way past the point of doing something about it. One thing for sure, the female me known as Carey would be always be well heeled, which I guess is not all bad.

Story Complete For Now

© 2016 thru 2021 Fran Cesca Walker

Leave a Reply

Your email address will not be published. Required fields are marked *