Shannon; Do You Like My Heels

My girlfriend Heather and I were out shopping at the local mall. I should clarify that, she was shopping and I was carrying her bags for her and paying for her purchases. We have been girlfriend and boyfriend for nine months now, haven’t moved in together yet, but quite often spending the night together in one or other of our apartments. She works for an advertising company, doing promotions and ads for their customers. She seems to be able to second guess the consumer, her ads fitting in with what the consumer is interested in at the moment. Several of her ad campaigns have been so popular the agency has used that same concept for some of their other customers. A couple of those being national ad campaigns.

She does spend a lot of time out where people congregate, like the mall, music festivals, or concerts. She is always looking how they are dressed, the colors of their clothes and what gender is wearing what, since a lot of things have changed fashion wise since the male models have taken over the female fashion runways. So today we are out shopping and observing. So far from the amount of bags I am carrying, I would say the emphasis has been on shopping but with Heather you can never be absolutely sure. From the many purchases she obviously has found lots she likes, but also has made many observations of the people around her.

One particular couple kept her attention for over an hour, as we followed them through the stores as they shopped. The couple would move on, with me left to catch up since I had to stand in line to pay for something Heather found she just had to have while observing them.

We came up to a new shoe store that had just moved into the mall, in one of the wings of the mall. They were still setting up displays, but the door was open and some customers were browsing what they had set up. Heather stopped dead in her tracks, with me running into her, since I was focused on her butt swaying in the little mini-skirt she was wearing. I looked up at what she was looking at, some gorgeous heels in larger than normal sizes. I saw the picture to the side of the display, a male dressed in a business suit, but with heels on. The only thing different was the length of his pants, stopping a few inches above his ankle. I presume that was so the heels could be seen better. The color of the heels coordinated with his suit color both in a muted shade of gray. There was some decoration on the pair of heels, a couple of straps in a darker shade of gray and a small bow right on the vamp of the shoe. That also done in a darker gray, making it look more like a flower than a bow. Looking at the picture more closely the guy was wearing stockings or pantyhose, since there was no sign of socks on his feet.

Heather found a clerk, asking if she could take a picture of the display after handing her one of her business cards. The lady agreed and Heather took several pictures. The lady introduced herself as Sydney the owner of the shop. Heather and her talked business for some time, while I wandered off to look at the rest of the displays. All of the remaining displays featured females in their pictures, the heels more colorful and severe. A few of the heels looked very tall, I would guess in the range of five to six inches. I would definitely like to see Heather in a couple of those heels, a boyfriend’s favorite fantasy coming true.

When I wondered back over to where they were talking Heather took my arm and pulled me close to her introducing me to Sydney. Sydney took my other arm and led me back to her office, Heather making sure I was headed in the right direction. We sat in some chairs around her desk, nothing really set up yet, kind of a semi-organized confusion, Heather’s many bags of shopping gathered around my feet.

Sydney had a piece of paper in her hand, explaining what she would like as she handed it to me. It was an advertisement wanting male models to wear shoes for her company. I briefly wandered if they also sold male shoes, but hadn’t set up those displays yet. She clarified it by telling me they wanted normal males to wear the heels in their daily tasks just like they would normally wear an oxford or a loafer. No sales pitch just answering some questions if asked by work colleagues. In exchange for doing this I would be paid twenty dollars a day, plus all of my clothing and lingerie needs. A different pair of heels furnished for every day, the inventory at the moment allowing for a ninety day period of wearing a different style or color of heel each day.

I looked at her, then at Heather shaking my head in a negative manner. Heather told her to sign me up, when can he start. I turned towards Heather shock on my face or was it panic. Sydney left the office to get something as I told Heather no way. Well that was not an acceptable answer as she got up and walked over to my chair and set down on my lap, her arms around my neck holding my head still. The area round me now crowded, the bags of shopping around my feet and now Heather on my lap. Her lips approached mine and I swallowed hard, knowing that I had to keep my wits about me or I, indeed, will be wearing the heels soon. Sure enough after a lengthy negotiating session her lips and tongue had managed to close the deal.

Refusing Heather anything she wants has always been my weak point. At my strongest show of resistance I was only able to hold out for three days, and that was shortly after we met. Now I usually caved within minutes, but I do so enjoy the negotiating. My sizes were noted and information on my job was obtained so that my clothing could be matched to my job. Since my job was a mid-level administrator for a state agency, I am not sure how the needed approval could even be obtained.

Nothing overtly female in the clothing, for instance the suits were normal female pant suits but in colors more suitable for a male to wear. I would receive shipments from all of the different sources of my apparel over the next few days and would start wearing the heels and clothes a week from now, that allowing me time to practice walking and maneuvering in the heels. The money would be deposited directly in my bank account weekly so there would be no need for regular contact with Sydney. I was to wear the heels at all times except when I was in bed, whether grocery shopping or out on the town or just lounging around the house. I would also find suitable clothing for those other tasks in my new wardrobe being shipped to me.

As we left the mall I was totally bewildered. I had entered as a normal boyfriend to a sexy lady, but now signed up for wearing heels to my job and everywhere else. I tried to reason with Heather, that all of this was too over the top, a male these days does not wear heels for work and shopping. The deadly kiss was administered again for quite some time as I almost forgot my own name.

We left the mall, her destination being my apartment as fast as she could drive us there. Her bags of shopping were left in her car, the box she carried of my training heels tightly in her grasp. My pants were sliding down my legs before we made it across my living room floor, then naked before I was pushed into the bathroom.

The shower was turned on to warm up while she stripped. With a razor and shaving creme in her hand I was rudely pushed into the shower and covered in shaving cream. To keep me still she had her hand around my male appendage in a death grip, pushing forward or pulling back to get me where she wanted me, her other hand wielding the razor. Right before the hot water ran out I was hairless, not something to fear if it was just my legs, but she had removed all of my body hair below my chin. I tried to reason with her, a few jerks on my evident erection and I was quiet, content to be made hairless all over.

She dried me off, then I tried to return the favor. I was swatted hard on my butt, my penis shrinking in fear of him being the next target. She grabbed some body lotion she kept at my apartment for her after shower routine and coated my body in the sweet smelling cream. Junior was included, after she had covered all of the relevant areas she concentrated on my male appendage, quickly bringing him to the point of eruption, but she abruptly stopped, since she had other necessary tasks that needed to be completed first. I was weak in the knees from her ministrations so plopped my butt on the edge of the bed. Still naked she was right there alongside of me easing a pair of stockings up my legs, releasing them as they settled on my thighs. The elastic at the top of the stocking holding them there. The heels came out of the box and soon were on my feet, causing my foot to straighten out almost like I was standing on my toes. The strap around the ankle was fastened with the other heel quickly following. I was pulled to my feet and made to walk around the bed to get used to the heels. Meanwhile she was searching through her purse for something else.

After a few trips around the bedroom I was then sat at a desk I had at the side of the room, where I often finished reports due at the office the next day. She grabbed my hands making me lay them palm down with my fingers splayed. In quick succession she glued long extensions to each nail making my hand almost useless for doing anything. Then it dawned on me, the long extensions will keep me from unbuckling the strap around my ankle making sure the heel stays on my foot. I knew she was devious, but this was just plain mean.

Proud of her accomplishments I was kissed again and she left. So there I am standing naked in my bedroom, wearing heels that had about a four or five inch heel over stockings that came up to my thighs. I looked at the extensions on my fingernails and groaned. I need to learn to say no to her, otherwise no telling what I will end up doing for her. I guess I am doing this for me, the money going into my bank account. I am not poor by any means, but a girlfriend with her tastes, extra money is always appreciated and often required.

I tried to get comfortable, but even sitting down the arch of my foot was distracting and uncomfortable. I decided some clothes to cover up my nakedness might be helpful then yelled in frustration as none of my pants would slide over the heels. So I tried one of my workout shirts, a huge partially shredded shirt that had softened over the years and was comfortable. There again I had it on but could not fasten the buttons, frustration getting the best of me as I almost shed a tear. I was taught males don’t cry, so I tried to suck it up and make do with my situation. I left it on, it was at least covering part of me.

I headed in the direction of the kitchen, maybe some chips and a bowl of dip would lessen the frustration I was feeling. Chips and dip maybe a two minute task to get ready, with nails an almost impossible task at least for me. To even get into the chip bag was a major task. I ended up finding a pair of scissors to cut the bag open almost getting my fingers stuck in the handle of the scissors. It was five minutes before I got the jar of dip open, spilling more of it than I ate. I was going to get a bottle of pop to drink, but decided water from the tap in a glass might be more accommodating and realistic.

So after a few chips, barely managing to get any dip on them and a half a glass of water I gave up, returned the dip to the refrigerator and stalked off to the living room. The open bag of chips still laying on the counter. I realized I would be sleeping in the heels, unless I cut the straps. But then with the scissors I had, I am not even sure that was feasible. They were on my feet until I had help getting them off. I hoped Heather had intentions of coming tomorrow morning or I would be a no show for work. No way to fasten my buttons on my shirt or unbuckle the heels to get a pair of pants on.

I laid in bed for quite some time, even called Heather to see if she was coming tomorrow morning. Of course, she didn’t answer, so I was left in doubt as I finally slipped into a restless sleep. My alarm woke me, my bedding wrapped around my body tightly, one of the heels apparently caught in my sheet. The need to use the bathroom was worse than usual, so desperation was evident as I tried to get loose. I barely made it, I am sure upon closer inspection you would find a trail of drippings all the way from the bed to the bathroom.

As I returned to the bedroom I saw Heather standing there with a huge smile on her face. “Looking good girl, now we need to get you ready for work.” She approached removing my shirt and rubbing her hands over my nipples getting the reaction she was looking for. I pleaded with her, the start was supposed to be next Monday, not today. She just continued as if I had not said a word. The panties she removed from her purse had me backing up till I hit the edge of the bed and was promptly sitting on the edge again.

She got the panties past my heels and made me stand as she pulled them into place. My legs felt like mush again as the silky panty worked its way up to my groin. She manhandled my apparatus between my legs and pulled up the panties tight so that it remained there tucked between my legs. She laid a pair of pants she had brought with her next to me and unbuckled my heels. The pants were worked up my leg, then she replaced the heel and did the same with the other leg. With the heels on she re-buckled the straps. Then had me stand again as the pants were pulled up higher and the button at the rear of the pants was fastened. With that done she pulled up my zipper in the back leaving me trapped in the pants. A blouse was added from the items she brought and buttoned up the back. As she was doing the buttons I realized my fate today. Nothing so far could be removed by myself, unless she took off the damn nails.

I was panicking as I pleaded with her to not do this to me. She just smiled and continued slipping my arms into the matching blazer. It was a pant suit but obviously for females. As I looked down, the top part was not too bad, although the cut of the blazer made it look like I had small breasts. The pants though was a different matter altogether. They were normal to the knees, then conformed to my calf down to a point about three inches above my ankles. The sight of my heels would not be missed by anyone. I pleaded, stomped my feet, begged but nothing was changed. She found my wallet, and keys to my apartment and slipped them into a matching purse. My car keys were placed in her purse with an evil grin showing on her face.

My normally long hair was brushed back into a ponytail, similar to what I usually wore, this time instead of a rubber band she used one of her colored scrunchies, color matched to the pant suit. A quick look in the mirror revealed she had placed the ponytail higher on my head than I usually wear it.

She took hold of my hand and before I knew what she was doing I was being dragged through the living room and out the apartment door. The click as it closed and locked behind me very ominous. Out to her car and then placed in the passenger seat. I was told to fasten my seat belt, a task that proved impossible with the long nails. She leaned over hooking it together and then stole a kiss. I swear I was sweating when she pulled away from the kiss, short of breath and at a loss for words. I was driven to work, then extracted from the car as she walked me into the office.

Everyone greeted her since she often came by to take me to lunch or take me home. Then my secretary noticed my heels. She squealed and that caused all of the rest of the girls to come and see what was going on. Meanwhile Heather left me there to explain myself to the girls as she knocked then entered my bosses office. Shit what is she telling him about me. Knowing Heather it can’t be good. A few minutes later I was called into his office, he was standing at the door watching me walk into his office. His only comment was you look very nice today, the heels in particular seem to be perfect for you.

I was told to stand in front of his desk as he took in my appearance from head to toe. He asked several questions of Heather, but I was not included in the conversation. I was about to say something when he spoke. “No problem with your unconventional dress, I do insist on a business professional look though. With wearing the heels I think the female dress code should be applied in this case. For the time being use the unisex bathroom on the second floor, till we get through a few days to see how this will work out. I think we need a more ambiguous name then Shane though since you looks are bordering on being feminine. Once that is decided I will send out an email notifying all of the employees about the changes. I will insist that a full four month trial be utilized since we are going to all of this trouble to make allowances for you. Decide on a name and then get to work.”

Heather suggested Shannon, a cute name that fits her personality. James my boss snickered at her use of cute and her but agreed and typed up the email and hit send. Just like that it was all decided and I had been railroaded into a feminine persona not for three months but now for four. Heather dragged me out of his office and to my desk, then I was kissed hard and told not to drink much, she would be back at lunch to help me go to the bathroom. She looked at my face one more time, then reached into her purse and removed her clear lip gloss. My lips were covered twice and then I received another kiss and she was gone.

I just sat there not knowing what had happened to me today. Hurricane Heather apparently. I tried to focus on my work but it took about any hour before I could get anything accomplished. I did notice a steady stream of people coming to see Shannon in her first day at work. An hour before lunch I was called into James’s office, dreading what this was about. His boss was there seated in his desk. I stood there to let her appraise my looks, She was elected to the office, but in all fairness she was probably one of the few elected people that actually knew what her job entailed and was more than qualified to do it.

“You look very nice Shannon, the pants suit is very stylish and the heels are to die for. I think a little more makeup might be called for, and you need to loose the ponytail maybe a curly bob will better suit your features. Now we need to talk for a while, have a seat and we will get this out of the way. From what one of the girls said when I came down this morning this is a result of your fiancee’s efforts. I knew Heather from school, she does have a way of doing things, full steam ahead and pity anyone that stands between her and her goal. I take it you are okay with this, maybe not enthused but able to, live with it.”

I nodded my head, sighed and she giggled. “How about we take this to the next step. If word was to get out about you wearing heels to the office everyday we might get a little too much media coverage. That is not necessarily a good thing. Now if this was other than a state job they would be no interest, but anywhere politics enter into the picture everything is fair game. They tend to sensationalize things to get readers and viewers to watch and buy their papers. Now if we classify you as a transitioning transsexual they have to leave the matter alone. It is just a matter of changing your personnel records and making your name of Shannon your legal name for work. All of the employees have to treat you with respect, no bullying and no rude remarks or name calling will be allowed. You will then be viewed as a valued female employee and treated as such.”

It also opens up your choices of clothes that you can wear to work. I think you will be quite attractive in a nice pencil skirt and matching blazer. Also you are young enough to wear a modest mini skirt, showing off your legs to their best advantage.

I have went over your file, I see your work has been consistently above average, doing way more than your job description requires. James is being promoted soon, how about I allow Shannon to assume his duties now to see if it is something you might like doing for the long term. I am confident of your ability, but think that maybe you need a little time in the job to see if it is what you want to do. Both the role of Shannon and James’s job. Take a longer lunch and talk it over with Heather, telling her what you want her to know and keeping the rest between you and me. Give me a call later today before you go home and let me know your thoughts. I see Heather waiting outside for you, have a nice lunch and we will talk later. Good luck by the way.” A smirk and giggle accompanied her last remark.

I thanked her and swiftly left the office grabbing Heather and heading for the unisex bathroom on the second floor. Heather had an idea what I intended and other than walking slow to increase my frustration she did follow me. Once in the bathroom she undid my pants letting them slide down my leg. I managed it get my fingers in the waistband of the panties and got them down my legs. I sat on the toilet and almost flooded it, the relief of not having to hold it showing on my face. Heather instructed me on what I had to do as a female to wipe then helped me get my panties and pants back up and buttoned, then zipped. The nails making doing the simplest things so difficult.

She refreshed my lip gloss and we headed out to the parking lot and her car. She wanted to know what Cynthia was talking to me about, I just shrugged and asked Cynthia who. When we got to the restaurant I had to pay for my remark about Cynthia as she applied mascara, lipstick and eyeliner to my face, then released my ponytail and brushed it out. In the visor there was very little male in the image before me now. Shannon was the only image to be seen, and that was decidedly feminine.

My arm was grabbed as we got out of the car and she led me into the restaurant, asking the hostess for a table for two right up front. No chance of me being ignored or not looked at this way. The waiter got our chairs for us, something I was not used to. We ordered our meals and drinks and he left. Heather leaned closer whispering onto my ear, either you tell me what was going on between you and Cynthia or I will leave you her to pay the bill and figure out a way to get back to work or home. You have forgotten something a female never leaves behind, her purse. You left it on you desk, not going to do you any good there. She stared at me, waiting for the information I had been denying her.

Okay you win, I will give you the highlights now, tonight I will fill in all the details. I have been promoted and as of tomorrow will be classified as a transsexual entering transition. I can now dress as a female, skirts and dresses are allowed, but I need a gender neutral haircut and probably need to wear some makeup most of the time now. It is a trial, to see if I like the job and the life as Shannon. I imagine this will end the high heel deal, since I will no longer be dressed as anything resembling the male sex. I want to take it to try it out, but do not want to lose your love or your friendship, so only if you agree to me doing it.

Well her answer was delivered only moments later as he hugged me and kissed me squarely on the lips after leaving her chair for my lap again. We got some clapping from the surrounding tables, I think they were just presuming we were a lesbian couple that didn’t realize we were in a public place. Of course, I was beet red in the face, just not used to being kissed in public on the lips while dressed as feminine as Heather.

We ate in peace, with Heather looking my way often deep in thought. I got a smirk every so often, this can’t be good. She is already planning something, probably something I will not be happy about. I was dropped back at work after she applied more lip gloss to my lips and refreshed my mascara. I got hugged hard, but no kiss this time. As she was getting ready to drive off she told me to let Cynthia know I will accept her job and conditions. Plan on dinner out then some time at the beauty salon. Shannon goes 24/7 tonight for the rest of your life. Now get and don’t forget your purse tonight.

I just stood there as she drove off, did I hear her correctly for the rest of my life. Oh gawd, now what do I do? I made it to my office, then called to see if Cynthia was available. She was so I made the trek to her office, knocked and then entered. She smiled, holding her hand up to keep me from saying anything. I presume since you are standing here it will be Shannon from now on, and not for a trial period. Heather has you wrapped around her finger so tightly, I suggest you read up on being a Mother, I am sure she will have you having the kids and raising them very soon.

But in matters regarding your employment here I have already made the changes to your personnel file, one of the lawyers working for the state will be down in a few minutes to have you sign your name change, which will include a gender change for your file.

My mouth was partially open as another knock on her door and the lawyer entered, showed me the documents and had me sign them. He left me a copy, I will be officially a female named Shannon as soon as the paperwork is filed, approximately three hours from now. I can see that Cynthia and Heather are pretty much alike, but my boss does not rely on devious methods to get her way. I wonder if they are in communication with each other or is it just a case of bad karma on my part, a lot of bad karma if today is any indication.

I returned to my office, just now realizing that wearing the heels was comfortable, just a little ache in the calves of my leg. Of course, I have not been on my feet for most of the day. The traffic in front of my office has diminished considerably, I presume most of the other employees have seen me in my heels now, so I am already yesterday’s news.

I managed to get some work done, once I figured our how to use my keyboard with the long nails. Bt quitting time I had almost caught up with what I had to do today. I did remember my purse as I got ready to leave. I even applied a coat of lip gloss to freshen my lips. As I made my way to the front of the office building I noticed quite a few sets of eyes following me. I wonder if it is because I am a male wearing heels or if they think I am a female. Walking in the heels my ass seems to be in motion most of the time, no matter what I try to do to correct the movement the motion remains.

Of course, Heather was waiting for me getting my car door for me after she checked my lip gloss with a kiss. I passed apparently, but she did a follow up kiss to make sure. I was taken to her apartment, then helped out of the car. As we entered her apartment the whole living room was littered with boxes. I sat down in the first unoccupied chair I could find and lowered my head into my hands. I had a bad feeling that all of these boxes were for me, heels and clothes for work and at home. Gawd, why couldn’t Sydney wait a couple of days before she implemented all of this.

Sure enough it was all for me, Heather adding it all to her extra closet in the guest bedroom. While hanging the clothes she found a couple of items she laid out on the bed, I presume what I will be wearing tonight. I hoped she would forget her comment about me going to her salon, no such luck. Once everything was put away, her attention returned to me. I was undressed, made to use the facilities then re-dressed in what she had laid out for me. A new pair of heels went with her choices for me, these even taller than before. Since you will only be on you feet for awhile while out at the restaurant, then at the salon I am sure you can manage quite easily. The outfit she selected still had pants, but no jacket tonight, the blouse had long sleeves but with a scoop neckline. It implied I had a bust since the material was cut to allow for sizable breasts. No gray color tonight, the pants were a light burgundy, the blouse an off white with matching burgundy accents on the sleeve cuff and the scoop neckline.

The restaurant was the local diner, a burger for each of us and lots of interested looks for me. No fries by the way. I have a figure now to watch so just the burger and a diet drink for dinner. I guess that will be the norm now, even if I passed as a female the height of the heels will attract lots of additional attention. I swear the heels were at least five inches high, a bright metallic gold color with burgundy accents. Along with the heel height the heel tip was a stiletto pad of less than a quarter inch across, making standing and walking quite a bit more unstable.

With nourishment handled, the salon was next, the whole time driving from the diner to the salon spent in me trying to get Heather to not indulge in any further procedures for me. Wasn’t it enough that I had to wear the gender neutral clothes and the feminine heels without pushing the envelope any more. Heather’s answer to that was a resounding no, a unisex hairstyle, a brow shaping and pierced ears were a minimal requirement for this appointment tonight. I pleaded with her, but to no avail, her smile and smirk evident as I was led into the salon.

I was not sure why I let her decide my fate. I should have put my foot down and refused any more being done to me. Then I looked down at my heels and sighed. Sure me putting my foot down in protest likely to get a few laughs, but the fact remained I was dressed feminine already and wearing stilettos. Barely able to walk in the higher heels kind of makes any confidence I might have in myself to resist Heather quite pathetic.

It didn’t take them long to make the changes, what little masculinity I might have displayed when dressed as a male was now severally hindered. The so called unisex hairstyle was dripping femininity, curls in a layered look with cute bangs. Walking by the mirror at the front of the salon the image displayed was of a female, not a glamorous type, but definitely a female. The eyebrows were now thin high arches and the two piercings in each ear already sporting diamond studs and large golden hoops.

Heather insisted I stay with her at her apartment, I was figuring the guest bedroom, but she insisted her bedroom right next to her. When we stay over in each other’s apartment we do share a bed for a while, then leave to sleep the remaining part of the night in the spare bedrooms. I liked the new sleeping arrangements, cuddled up next to her is like a slice of heaven on earth.

That is where I found myself the next morning, a warm body lying next to me her breast and nipple almost in my mouth. The breast had escaped her nightie, such a wonderful way to wake up. What is a person to do when faced with that situation? What else but give it a lick. I received a low moan in response so I moved closer and sucked on the nipple while rubbing her other breast through the nightie. It didn’t take but a few minutes to bring her to orgasm, her hands now at the sides of my face keeping my mouth right there on her nipple.

I slipped off to the bathroom with a huge smile on my face, did my morning routine and headed back to her bedroom. Heather had recovered and decided I needed to be punished for my unorthodox behavior this morning. On her bed was my apparent wardrobe for today. I backed up trying to escape her grasp, but I was not fast enough. I was soon wearing everything on the bed and looking very feminine. I moaned and groaned at having to go to work this way, she said she would make it all better and headed to the guest room. Back a few minutes later she had a pair of heels in her hand, I swallowed hard they were nothing but straps with a towering heel of at least six inches. My feet were placed in them and the many straps interlaced and buckled. She expects me to be able to walk in these heels. On a positive note, the hairstyle fell back into place perfectly, my now thin brows accenting the feminine look.

As further protests were coming from my mouth I was dragged to her door and pushed out into the hall. I heard the door click behind me knowing that the current look would be how I presented myself today. The door opened again and my purse was handed to me. I opened it up hoping to find my own apartment keys, figuring I could go there and change a few things, to keep my appearance from being so feminine.

Well I found myself having to accept my present state of dress, no apartment keys and worse yet her car keys instead of mine. She drives a white VW convertible, not any car ever made more feminine that this one. It had a pink dashboard with leather seats and attached pillows for the head rest that were covered in lace. I doubted anyone would mistake me for a male in that car, no matter how I dressed.

With a face that was red for all to see I made my way to my office, I drove slow and used some back roads since the heels I am wearing are far from conducive to driving a car much less walking. No, I did not drive with the top down. I made my way into the office and went to my cubicle. I was walking a little better, but still wobbling more than usual, the unusual heel height really affecting my stability. A note on the door told me to go to my new office, the job starts today. I made my way there, set in James’s chair and logged on to the computer. Instead of seeing my old name of Shane, the log in showed Shannon now.

My new secretary came in after she had arrived, smiled at me and wanted to know what she could do to help. I asked her to give me thirty minutes to see what was going on. Instead she handed me a sheet of paper with all of the outstanding situations that were in process. As I was looking at the sheet she asked me my preference in drinks. I told her tea if possible, she turned and made her way out of the office. It was only ten minutes later when she appeared again, putting a hot cup of green tea in front of me. We introduced ourselves and she made a couple of suggestions on what to attack first.

Her suggestions turned out to be correct, the day went surprisingly fast as things came together without much fuss. I had to use the restroom, so was out from behind my desk for the first time that morning. On the return trip Monica complimented me on my heels and my ability to maneuver in them. That started a discussion on how I ended up wearing them and her outright jealously at the fact that I had over ninety pair of heels to choose from. Her words as she was giggling away, that is so wrong for a male to have better looking heels than a female, and so many more of them to boot.

We became more than just secretary/boss in the next few weeks, we became friends. On more than one occasion we discussed the deal that I was offered, finally Monica filling me in on why they could pay me money to wear the heels for three months or more. As heels are worn all the time the leg tendons are shortened, thus requiring heels being worn from then on to be able to walk comfortably. What they pay out will be recovered quickly when the male has to buy heels to be able to walk. The fact that the male foot is a little larger than a females will require him to go back to where he first got the heels. He will soon realize that a good quality heel will cost him somewhere between two hundred and five hundred dollars a pair. At that price Sydney will soon recover her outlay. If the male gets used to matching his heels to his outfit, a few pairs of heels will become inadequate, thus a color and style for every outfit.

She confessed that females fall for the same type of hoopla, there legs looking more sexy and desirable in heels thus more attractive to their possible suitors. Most all of the female role models are always shown in heels, usually the higher more stylish stiletto type of heels.

I thought back to Heather and her signing me up for Sydney’s program, wondering if she would get a cut of my earnings for enrolling me. Maybe she just liked me in sexy heels, kind of helpless and dependent on her for things. I debated confronting her on this, but decided I liked the way things were between us, if me wearing heels all the time was to be part of this I think I can manage to abide with her wishes. Besides I liked my salon time now, being pampered at the salon, then home to Heather to be ravaged is something to look forward to.

I did get noticed a lot at work, when I made my daily trip to the deli around the corner to get our salads for lunch I was ogled, stared at and even approached asking about me wearing heels. My standard reply was do you like my heels? I am sure I sent many an individual to Sydney’s shoe store, I just hope they remembered to mention my name.

Heather continued to get her way concerning me, now I have breasts of my own, and quite often wear skirts and dresses to work. I guess it is a logical step forward for me, since I am dressed so feminine now every day. I did get a week of intense negotiating out of the deal. I have learned there are advantages to being female and have learned from Heather how to get what I want out of the deal. I used a half tube of lipstick that week, it was worth it for the sensuous kisses I received as I was being persuaded to get my own set of breasts.

Shannon became accustomed to her new job, doing well and was soon promoted again several months later. I remained in heels, now a necessity to be able to walk. Sydney did make her investment in me back, I now shop there regularly along with quite a few of my male colleagues. When we meet up in the office building our smile and greeting to each other is now standard. Do you like my new heels?

Story Complete For Now

© 2016 thru 2021 Fran Cesca Walker

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