Debbie; Asking A Lot

I am a recent addition to a work group, its sole function to court and sell a new customer our products. Our company manufactures different female products, from cosmetics to lingerie, and this retailer had withstood our best efforts to get them on board. So our company put together a select group of people with different skills to approach and try to land the customer. All were female except me, my field of expertise not often inhabited by females. I am the numbers person, supplying all matter of statistics to impress and influence sales of our products, yeah right.

There were three other members of the group, two sales specialists and one experienced in logistics, shipping and custom orders. When we met for the first time, I am welcomed into the group, like what I do would actually influence the courting of the customer. I wondered what I am doing here; these women knew the products backwards and forwards; there experience in handling special customers quite obvious.

Shauna and Beth were the sales specialists, and Katrina the shipping guru. When we had the first meeting of the group, all is explained to me, their detailed explanation making sense to me, somewhat. Jennifer McNeil is the name of our customer, running a multi-million dollar business composed mainly of three hundred retail stores. She has a reputation in the industry and has lived up to it apparently. She is strictly no-nonsense, once she takes a position, she never wavers.

The company wanted her business badly, the reason for this group is to try and sway her to becoming a customer of ours. To even get her to attend an upcoming convention we had to make lots of concessions. The convention is a regional women’s show where lots of companies rent space to show off their wares. We always rented large areas for our products, a good way to show everybody how diversified our company is.

We figured if we could get her to attend, we would have an advantage over the competition since we rented about a sixth of the display space available for our business. Then we could try and sway her with numbers and discounts to get her on board. Essentially we would meet her at her company’s headquarters, then fly her on our corporate jet to the convention, put her up in the convention hotel, then wine and dine her till we could get her signature on the dotted line. At least that is the plan.

In several meetings before we left to get her, we went over every facet that she might visit, Shauna making sure that all of us are prepared to the hilt. One chance to make the sale, then failure if we messed it up. Beth mentioned some facts that they had found out from some of her previous encounters with the competition. She liked to go to the extreme to force compliance, or give her a way to walk away from the proposal. One time she had told a salesman that in order for her to believe what he was saying she wanted him to disrobe right where he is standing, then stay naked during the rest of the sales meeting. He refused, and she walked out, not even accepting calls from that company anymore.

Another time she asked a female sales representative to remove her blouse to prove she is wearing her own product, her refusal ending the conversation immediately. Jennifer told her as she left that if the product you sell is not good enough for you to wear, how do you think I can sell it in my stores. The ladies in our sales group were dressed in the company’s clothes and using the company’s cosmetics; there would be no occurrences like that in our discussions with Jennifer.

We left in the corporate jet, chatting about our target and possible ways to influence her. Since Shauna is the most confident of the group she would be our boss in the negotiations, steering us in the proper way, hopefully, to get a signed contract. I estimated that her signature would generate sales of somewhere around ninety million dollars for our parent company. That figure made the project real important to the future of our company’s business.

When we reached her corporate headquarters, we had to wait as she was already in a meeting with some of her employees. When the meeting broke up, we were introduced to her; she shook each of our hands then handed me her purse, telling us we needed to get going. Immediately I was in shock, carrying her purse as we left her offices. Then I was handed her overnight bag, a cute smirk on her face.

The limo ride back to the airport is fairly short; she wanted to know what is planned for the three days, and when we would meet to discuss the deal. The trip was a non-event, a little business was talked about, but nothing more than that. We took a limo to the hotel and got everybody checked in. I smiled a little, she seemed to take pleasure keeping everybody off balance, never allowing them to get their game together. Shauna reacted well, when we get you settled in your hotel, we will have dinner and discuss what you would like to do for the three days of the show. Jennifer sported a little upturned lip; she saw us sidestep, well now we can see how much they truly want my business.

I stayed in the background, watching the back and forth between Shauna and Jennifer, a real exercise in gaining the upper hand. Every once in a while, I would catch Jennifer looking my way, but when she saw that I am watching her, she would return to her conversation with Shauna. We left to get ready for dinner, each of us had a room in the hotel also, to make sure we were available to meet with Jennifer whenever she desired. Shauna had made reservations at an Italian restaurant, known far and wide as a five-star plus facility. I watched from afar as the four gals made polite conversation during dinner, then almost bit off my tongue when Jennifer asked me a question.

She wanted to know what my part in all of this amounted to. I told her I am the number cruncher, supplying the figures needed to complete the deal. Then she surprised me by asking a flurry of questions about our product and its projected effect on her sales. I answered quickly and to the best of my knowledge, then as fast as it had started she turned to the others and I am ignored. No comment on the figures I supplied, nor where I obtained those figures.

The dinner wrapped up about two hours later, and we adjourned to our rooms. She wanted to meet early for breakfast and get an early start on the show. I dressed casually the next day, we had breakfast and then walked the show. She spent the necessary time in our booths observing the products we manufactured and the variety of our product.

The unusual part in all of this is that she had me carry her purse everywhere we went. No comments were made, when we would meet up she just handed me her purse and we went about our business. It bothered me at first, but since nothing was said about it, it became just another thing I was expected to do. There was never any more mention on my projections on her sales, so my presence in the group was really not necessary.

We went to a small bistro, a block from the convention and ordered salads to eat. Jennifer is unusually quiet during the last of her lunch, and more than once I caught her looking at me, kind of sizing me up. Yesterday she looked away when I caught her looking, today she didn’t causing me to break eye contact. She asked if we could go to a private room to discuss a request of hers. Shauna is smiling, hoping that we now had a deal. We went back to the convention center and used one of the meeting rooms they supplied for businesses. We all set down, and Jennifer cleared her throat, then started the dialogue.

“I have a proposition to make to your company, it is a test of sorts to see if your products are as good as you say; it is also a test of your personal commitment to the company and your products. You have until the convention ends to accomplish this task, hopefully to my standards. It will take all of you to accomplish this, your teamwork and your commitment to your company will be tested. I will sign a five-year contract with your company for all of your lines, and put them in all of my stores; I am sure David can supply the amount of money this is worth to your business. In exchange, I want David turned into a female from the skin out using your products mainly, the more you utilize, the more favorable I will be to signing.”

Shauna and Beth had inhaled sharply, none of us saw this coming, pure shock on everyone’s face. Katrina was trying to keep her composure while her mouth remained wide open. There was a little smirk on her face though. I just sat there numb now, not able to get a single thought out of my brain, panic slowly rising and making itself known.

Jennifer suggested that their first action would be to ensure that I would participate in this. “I am sure him being a male, might make his participation less than enthusiastic. I remind you that I will accept no one other than David. Although he is obviously a male, his appearance could be changed to that of a female with some talented help. If the job is thorough enough, I will sign, but I am looking for 100% female, not any half hazard attempt to fool me. I will be making a detailed inspection of her when she is ready, providing you can get David to participate in the first place.”

“I am sure you have checked me out enough to know that I do some odd things from time to time, but I think I have exceeded myself with this project. If done as I wish it will show me you companies and your individual commitment to your products. Incidentally, the unveiling of your masterpiece will be at my office the exact time that the convention closes two days from now. Now I think I have my fun for the day; I will bid you adieu and hope to see David two days from now. My own company plane has just landed so I will fly back and look forward to David’s and my meeting in a few days. He is to arrive by himself with the contracts, and after my evaluation, I will discuss the contracts with her. If all is in order, I will sign, even making a sizable deposit on the first orders.”

She got up from the conference table and walked out. Shauna is the first one to get over the shock, looked at me then smiled. She got her cell phone out and was calling corporate a few seconds later. She had to wait for quite some time to be able to talk to our CEO, Beverly a longtime friend of both Shauna and Beth. They talked a while, then Shauna is writing some figures down on a tablet. She broke off the call, then asked Beth and Katrina to start planning my transformation if I agreed to the project. She sent them to their rooms and dragged me to hers.

She set me in a chair next to a love seat grouping in the corner of the room. She set on the love seat and stared into my eyes. She asked if I had any idea that Jennifer would pull this stunt. I could only tell her of the numerous times I caught her looking at me, and how today she would not look away when I caught her staring. She asked me my thoughts on what she has proposed. I told her that I am still in shock, but I didn’t want to be turned into a female just to keep my job or land a contract.

She understood that, she didn’t think many males would be interested in the deal with those conditions. She wanted to know what it would take for me to agree to help. I didn’t want to commit myself, then find out they had in mind more, so I turned it around on her. I also wanted to know how far the transformation would go, from her perception of what Jennifer wanted. Shauna thought it would be all the way other than the actual removal of my penis. The more realistic the image, the better the chances of the deal going through. Well that certainly upset my being both physically and mentally. My stomach rumbled a little, too much unsettling info to deal with.

I took in a huge breath, doing everything I could to keep from fainting. I am not sure if it was the words ‘all the way’ or ‘removal of my penis’ that caused my concern, but either group of words had my undivided attention.

Shauna wrote a figure down on the pad she held then slid it over to me. My eyes almost bugged out when I saw the figure; then my mind started to realize all of the possible ways this could go wrong. How long will the changes be with me, can they be removed quickly or will I be stuck with some of them for a while, or worse just stuck with them permanently. I slid the pad back, I am not interested, they are way too many things that could go wrong, and my life is not worth that little. She smiled then jotted another figure down, this time, a percent figure.

I looked at her straight in the eyes and asked what the percent figure is in reference to. “It is the percentage of the sale if you get her to sign, if the deal falls through you get a quarter million just for doing it. If you want your job back, that is assured but at a higher level. We don’t have much time, so take an hour and think it through, then let me know what you decide. I wish I could tell you more, but this has surprised everyone, and we are all scrambling just trying to figure out what can be done and how it can be accomplished. I personally hope you will try it, but I fully understand if you are not interested, there is so much at stake here, no one can really appreciate all of the ramifications of this proposal. Jennifer has exceeded her reputation; this is one shocking proposal that will have far ranging effects for lots of people starting with you.”

I returned to my room, laid on the bed and almost cried. In the past, I have hit things when I have been super frustrated, but this exceeded all of those times by a mile. A few tears leaked from my eyes, but I managed to keep control. Why me is the first thought, I suppose since I am part of the group, I got chosen simply because of my availability. Then the realization of what could be thrust on me in the next few hours, some of it known, the rest being thought of now, as the girl’s tried to figure out a way to meet Jennifer’s request.

The hour is soon up, and I returned to her room. She answered the door quickly looking at me to see if she could detect what I had decided. It told her that I would do it, I am sure what little brain matter I had is draining out of me as I speak. I did ask for lots of help, in what to do if I made it as far as her inspection, my sales ability a negative figure and I am sure my mode of dress at the time will not make things any easier for me.

She called the other two in, and a schedule is quickly put together for the next two days, actually a day and a half since I would have to fly to her corporate headquarters for the inspection and contract discussions and possible signing.

I didn’t have a lot of faith in either the transformation or my ability to close the deal, but I knew I had to try, why I got picked to be the chosen one baffled me. I didn’t think she hated me, but why me? After my schedule is written down, Beth grabs my hand and leads me down to the convention floor. We walk right over to the Turnabout Gurl Salon’s booth, and I am escorted to a chair at the back of the booth. They have been a customer of ours for years, in fact, most of the time we ship more to them than to any other customer. Stephanie, one of their stylists, gets me on a table and quickly removes all but my shorts. There is a privacy screen between the other convention goers and me, but the background noise makes it seem like I am naked in the middle of the crowd. She explains to get me transformed in time they need to do it here on the convention floor.

I am laid back, and she applies a cream to my front side not missing any areas, my beard area, and my eyebrows get included. While they are waiting for the cream to do its job, my ears are pierced, twice with a pair of studs and hoops inserted in the new holes. She then starts working on my hands, filing my nails into ovals and pushing back my cuticles. I didn’t even know I had cuticles until she started removing them. When both hands were completed, she glued on extensions to each fingernail that she had carefully picked out to match the width of my original nails. After each hand is finished, she placed them in a light box glowing with a purple light, to set the adhesive and make the nail appear natural.

The cream on my body is removed and with it all of my body hair. I never had a lot there before, mainly my legs and my arms, but now I had none, at least on the front side. The cream is still on my beard area and my eyebrows, as she started on my feet. The same filing into slight ovals, but thankfully no extensions are used. I have never dressed as a female before, heck I seldom even watched a female dress or do her nails or makeup, so this is all foreign to me. The sensations are pleasant, but not in a sexual way. When she finishes my feet, she then removes the cream on my face leaving my face silky smooth with not even a shadow where my beard had been before. Of course, my eyebrows had vanished too, the impact of them being removed really making a difference in my looks. My distinct forehead less obvious now, with my hairline seemingly lower than before.

I am turned over, my backside receiving the same cream and hair removal. As in when she did my front she had moved my shorts out of the way to ensure that no hair is left unattended to, a few minutes later she removed them completely. Finally, finished with the hair removal, I am on my back when she pulls out some stirrups at the end of the table and places a foot in each. She attached a strap to each foot to keep them secure, then spreads the stirrups so that she has access to my groin area. After I had figured out what she might be doing, I realized the degree that I would be subjected in this feminization effort. An hour later my male member is no longer visible, only a slit surrounded with two puffy lips are visible, my bottom half now female in looks.

I knew my mind had not kept up with the changes, now I am half female especially the part that usually defined the female sex, although my overall appearance is now leaning to the female side there is still a masculine edge there. Sooner or later there will be a defining moment when my mind realizes what has happened, and sheer panic will set in. I could hardly talk to a female without freezing up, and now I am one in looks, things can’t get much worse or can they.

My concentration wandered off again as a large machine is wheeled in next to me. Two cups are lowered to my chest, then positioned above my nipples. The cups are glued to my chest then the hoses attached to the cups. A fatty substance is added to the cups and then the machine is turned on, and slowly the extra tissue on my chest is pulled into the cups by the vacuum pump. From the size of the cups, I will not be short on breast material, if the cups end up being filled. The cups are hooked to the pump by hoses running from the cups to the machine. After the cups are about a fourth full, the pump goes to alternating cycles, pumping then off, then repeat the sequence. The whole apparatus warms up, the liquid that had been injected in the cups seems to be absorbed into the skin. The tissue in the forms stayed where it is at, the vacuum pressure never releasing.

While this is going on, two stylists were adding long strands of hair to my own hair, although the new hair color seems to be slightly lighter in color. I could feel the weight of my new hair pulling on my head, something to get used to. Then I thought about my breasts, and the lack of anything between my thighs, a lot more to get used to I am sure. Four hours later they seemed to be done with my hair and the cups on my chest now almost full with breast tissue. The convention is winding down, fewer people in the hall, the noise level greatly decreasing. The machine is turned off, I found out that the cups will remain dissolving slowly over the next day or two. They already were somewhat more flexible than from their original rigid form.

I sat there contemplating what is happening, a fairly normal male employed by a corporation doing the best that I could do in my job. Then all hell broke loose, Jennifer to be exact, and now I am sitting on the convention floor, with a female vagina, large breasts, manicured nails, hair free body, and on a collision course with extreme femininity, at least, to me it is extreme. When and if my body realizes what has been done to it, I am sure there will be screaming and overall panic, but for some reason, that scenario has not happened yet.

My hair is put in a braid, and I am given a bra and panties to slip on. The bra feels good, especially the support it provides. The panties look good, but the feeling of something missing down there is unnerving. I get a lavender sweat suit to wear, and I am hustled upstairs to my room. Shauna and Beth are waiting for me along with another lady that I do not recognize. She looks familiar, then all of a sudden I recognize Francine, her picture on most of the Turnabout Gurl Salon’s signs and promotional material. I sat next to her on a love seat, and she starts the conversation. Shauna and Beth leaving the room, with only myself and Francine still in attendance.

She asks about me, did I enjoy the treatments today, and am I looking forward to tomorrow. I tell her that I am okay, the shock and panic have not settled in yet, but I am sure it will eventually catch up with me. We talk for quite a while, as she finds out how I have ended up in this situation. My job prior to this most recent event, receiving quite a bit of attention. Francine is easy to talk to, and an excellent listener.

“Have you done any plays or drama in school?” Francine smiled as I contemplated an answer. “I participated in a play in grade school, but it was ages ago. The part was only a few lines, but I managed to pull it off.” I don’t think that experience will help me through this, that play had me cast as a woodland creature, somehow portraying a female is a little more complex than that character.

“That is what you are doing tomorrow, a part in a play that requires you to be in costume. You are playing a part of a successful female in a large corporation that is seeking to win a large and lucrative contract. You have a good looking body, great hair, and you are confident in your knowledge and leadership. Once we do your hair and makeup and you are dressed in some beautiful feminine clothes the world is yours simply by you claiming it. You will meet your new client, impress her with your knowledge and salesmanship, and then get her to sign on the dotted line. This you can handle with ease, a female, proud and self-assured.”

As we talk a little more, I express my doubt in doing any of this, my fear of fouling all of this up, I am not a salesman, just a pencil pusher in a large corporation. She smiles, did you not hear what I said, believe in it and I think you will do quite well. In fact, while you are flying back from your meeting give me a call and let’s discuss how you did, okay. She kissed my cheek, hugged me tightly and then left.

I moved to my bed, leaned back and am soon asleep. Let me tell you about going to sleep in a female body. The long hair braid at the back of my head was the first obstacle. The two breasts that were swinging around wildly were the next problem to overcome. I used to lay on my stomach that seemed to be not an option anymore, I tried to lay that way for a minute, but they felt very uncomfortable in that position. I finally settled on laying on my side, once I managed to keep my breast from sliding under me. The braid felt better that way, the fact that I didn’t have to lay on it the main reason.

I wish I had half of the confidence other people have in me; maybe it is possible, but can I pull it off, that is the question. For some reason those words of Francine’s did stay with me that night, I dreamed of being that self-confident female making my way through the business world, my two large breasts leading the way.

The next morning, I slipped out from my sheets, then made my way to the bathroom. I noticed the reflection in the mirror as I entered but only after I set to pee did I notice my clothing and my looks. I wiped, then stood up and took in the image again. No comment on peeing as a female, it was messy though. An attractive female returned the look, dressed in an ivory lace nightie, and matching robe. I don’t remember going to bed this way; I presume one of the girls had something to do with my choice of something to wear to bed. I slipped the nightie off and then took a shower; it felt good, the water pulsating off my body made me feel energetic. It also did other things to my new body, so I bit my lip and tried to end the shower as soon as possible.

For some reason, I instinctively kept my hair dry, then blotted my skin with a towel after emerging from the shower. I wrapped the towel around my breasts, like I have seen many women do in the movies then made my way to the bedroom. I just referred to the objects in my chest as my breasts, what a bizarre thought, maybe after all of this is over I might do well to schedule an appointment with a mental health professional, providing it is not too late.

When I got back to my bed, I noticed another set of sweats, plus a bra and panties there, so I put on the bra, then wiggled into the panties followed by the sweats. The bra did require some contortions, but eventually it was secured around my chest. The hair is still in the braid, although strands of it are attempting to escape. The image in the mirror is female, of that, there is no doubt. Maybe I can do this, I just have to finish convincing myself of the possibility.

I picked up my room key and then made my way downstairs. I stopped at the restaurant and ordered a roll and some Orange Juice. I then made my way to the convention floor, and back to the Salon’s booth. Stephanie is waiting for me, so I plopped my butt down in the chair, finished my roll, and told her let’s get on with it. She smiled, “Francine must have given you a pep talk last night, confident and self-assured I presume.” I nodded my head, “now you have to make me beautiful, then I will be off to do battle in the corporate trenches. A prayer would be appreciated, maybe two if you can spare the time.”

Both of the girls came rushing up to me, short of breath wanting to know where I had been. I pointed to the chair, here. They broke out in laughter, then started asking lots of questions. I told them to leave Stephanie and me alone; we will handle my looks; you get everything ready for my presentation, and I will see you around eleven. Now get. Shauna, in particular, smiled, this is a side of David we haven’t seen. Well duh, the reason that you haven’t seen this side of him is that I am not David, my name is Debbie, and I am on a mission. Now get.

Giggling can be heard as they left, I just hope I can keep the confidence to handle Jennifer in the same way. Speaking of keeping the confidence, I had no idea where that confidence came from. I remembered the talk Francine had with me, I think, but I have never been confident in anything I had ever done or attempted to do in my past life. Hell, I am an employee trained in producing numbers for the corporation, not some super sales woman attempting to close a multi-million dollar deal. There is that word again, woman, I may look like one, but acting like one, we will have to see.

Makeup is applied, and instructions are given for repairing mascara and lipstick. My hair is set in curlers, and I get to experience time under a hot dryer in my quest to be beautiful. The curlers are removed, and a curly hair style now frames my face as she sprays it with hair spray to hold the look. I get a few lessons in recreating the look, and then instructions for a ponytail if all else fails. Of course, just like the girls everything I am wearing comes from our company.

Then I am removed to another room, where a lot of clothes are hanging on racks around the room. My bra is removed and replaced with a corset, with cups that support my breasts. The corset is tightened several times over the next hour as stockings are eased up my legs and heels are slipped on my feet. I almost lost it when the stockings were slid up my leg, they felt so nice, sending all kinds of feelings to every part of my body. Three-inch heels now adorn my feet, making me look imposing.

Finally, the ivory business suit with a pencil skirt is slipped on, the suit jacket having a low cut neckline to accent my cleavage. The tan lacey blouse helped cover my breasts, but seemed to only draw more attention to the low cut suit jacket. I hugged my miracle workers and complimented them on their work. Then I turned this way, and that as I am admiring my image in the mirror before I walk out the door and up to my room.

In my room, I find my briefcase on a table, checking its contents I find most of what I might need. The contracts are there, along with some notepads and some pens, the file on Jennifer is in there also, in case I need to refer to it. Next to it, on the table, is my purse, opening it I see the rest of my things, along with lipstick, mascara, a hair brush, and some face powder. Then in another compartment some tissue and some tampons, I presume those items make me appear authentic right down to the last detail. I leave my room, looking for Shauna. She is coming out of the elevator and walks right past me.

I turn around and follow her for a minute or two then when she is in a line to enter the convention I ring her on my cell. When she answers, I tell her to turn around and say hello to Debbie. She is stunned by my appearance, I turned out much more attractive than she envisioned. We talk for a few minutes then I tell her I have to get going, I want to arrive early for my meeting with Jennifer. A company limo is outside waiting for me courtesy of Katrina. I got a good luck hug from Shauna as the limo headed for the airport.

Talk about being nervous; I am scared to death. It is one thing to be portraying a female, but doing that and attempting to close a business deal at the same time is highly stressful. The plane is waiting and as soon as I am on board and seated it moves down the runway to get airborne. The flight is pleasant although it seems to take forever to get there. I go over in my head all that I need to do to ensure a successful outcome of this meeting. The female part is most convincing, everything realistic including my vagina. I even practice my female voice a little, my male voice never very strong, now I find out that by talking a little softer and more breathlessly I sound somewhat female. Now if I can keep her off balance, maybe I can secure a deal before she gets her game on.

Jennifer’s limo is waiting for me at the airport, and the short drive to her corporate headquarters is done in record time. I made my way into their headquarters, then up to their executive offices. I check in with their receptionist and am shown to her office. I take a deep breath and enter the office. Let the games begin.

I walk right up to her desk and offer my hand. Her mouth is open as I shake her hand, then I promptly sit down and open my briefcase. I remove the contracts laying them in front of her and suggest that she review them before she signs. I asked how business is, and tell her I think she will be pleasantly surprised with her sales, once our lines are added in her stores. I sit down on the chair in front of her desk, then stare at her, my legs crossed at the knees. Her mouth is still open, and her speech is severally impaired. I did hear the word David somewhere in that vast silence that permeated the air.

“David couldn’t make it; he is indisposed right now. My name is Debbie, here to accomplish only one thing and that is to get your signature on the contracts in front of you. While we are discussing business, are you aware of how much our cosmetic line could impact your lackluster sales in that area?” I had only made a guess there; I had nothing to back it up. Since she is still quiet, I must have hit on something. I rattled off some figures based on some of my projections, then continued with figures on our lingerie line. Somewhere during that time her mouth finally closed, and a smile appeared on her face. By the time I had finished my spiel, her smile seemed to encompass her entire face, looking more like a smirk than a smile.

We sat in silence for a couple of minutes, then she got out of her chair and approached me. She took my hand and dragged me to her love seat, her next question surprising me. “How do I know that you are truly David and not some impostor trying to get my business?”

“You don’t, and I am not going to tell you. Now are we going to discuss business or do I need to call the airport and get my plane ready to fly back?” We had a stare down, for several minutes, then she is the one to break first. “I am impressed, not only your looks but the total change in you. Confident, self-assured, not anything like the David I met yesterday.”

That made me think, I have changed, and I can only blame it on my transformation. Nothing else has changed since yesterday; I do feel more confident dressed as a female, feeling that I can move mountains. The best example of that is me standing in Jennifer’s office, telling her to either get down to business or I am flying back. I don’t think even Shauna is that confident in herself.

I should have been ready for another Jennifer surprise; I have let her have too much time to gather her thoughts and make plans. “Before we get down to discussing contracts let’s get something to eat. I know a nice quaint Mexican place, excellent food, private booths, and they even have entertainment. We can learn a little more about each other and enjoy some good food.”

I agreed, but asked if what I had on is proper dress for the restaurant; I imagined any place that Jennifer ate at was more than just a quaint little place. She told me not to worry; we could stop along the way and pick me up something to wear. I raised my eyebrow but agreed to her proposal. Big mistake. I took my briefcase, along with my purse and we left her office in her limo. Twenty minutes later we pulled into a boutique that screamed ritzy and made our way inside. Jennifer is greeted by name, and we are led to the back fitting area. Next to where we are seated is a rack of dresses, I presume picked out for her to try on.

Jennifer had me look through them and pick out anything I might like. Then with a twinkle in her eye, she told me she could pick out the one that I would find fascinating without even looking. Another raised eyebrow from me, then she went to the other side of the dress rack and marked the one that I would pick. As I was looking through the dresses, she told me that if she is right, I would have to wear a dress that she picked out for me as her reward. Most of the dresses on the rack looked middle of the road, so I felt safe and agreed. After looking through the rack, I pulled out the one that interested me the most. I have been exposed to women’s clothes for less than twenty-four hours, and here I am picking out a dress, go figure. When I turned the dress around there is a tag on it saying Jennifer’s choice. I quickly go to the other side of the rack to see if all the dresses had the same tag on them. Jennifer smiles, “you don’t trust me do you?”

Since she had predicted the dress I would pick, I had to wear her choice for me. The dress she wants me to wear can be only described in one word, scandalous. She leads me to a changing room and pushes me and the dress inside, then asks if I might need assistance in putting it on. I decline, but it took me twenty minutes to get into the dress alone, even then the zipper is not up, and I had to hold the front of the dress to keep my breasts covered. The dress barely covered the cups of my corset, the tops of my breasts peaking over the neckline of the dress. I felt almost naked, some of my self-assuredness slipping away.

I knew I had to recover my confidence, this dress not doing anything to help with that. I felt like I am on display, the skirt is extremely short, the coverage of my breasts almost non-existent. The color of the dress is a bright red; no one will miss seeing me in this sexy concoction. Of course, I had to have appropriate shoes; the five-inch stilettos made my legs look good but hindered my walking quite a bit.

The only thought that kept running through my mind is look at the mess that you have got us into now, you might seem confident, but this dress certainly levels the playing field. This all taking place in my head, my male self-trying to reason with the Debbie persona. I gingerly stepped out of the dressing room and made my way to the mirror right outside. Jennifer stepped up and zipped up my dress for me, then leaned in and hugged me. The feelings that were inspired by that hug should be labeled lethal, the goose pimples that sprouted next almost caused me to faint. Jennifer helped me to a sofa nearby and eased me down into the soft cushions.

She told me to relax, while she tried on her dress, then we would head to the restaurant. I looked in my purse for my phone, noticing that I had several calls from the girls, probably wanting to know where I was and if I had made any progress. I kept the phone set to mute; I didn’t need anything else compounding my thoughts until this situation is resolved.

By the way, how do you resolve a situation like this, I had a bad feeling that there is now something between us other than business dealings, and I didn’t have any idea how to handle it, I am still having trouble handling the business end of it, much less anything else. If there is some attraction between us, how do I respond to her advances? I am not sure what I feel for Jennifer, she is attractive, very personable when alone and she does fascinate me. I guess there is some attraction on my part, but with my past history, I probably wouldn’t recognize it if it hit me over the head.

There is a reason that I am still unmarried at the age of twenty-six, my last date is while I was enrolled in college, not really a date, just some girl needing someone safe to go to a wedding with. I can hardly talk with a female, without freezing up, the words just don’t make it past my lips. When Jennifer first asked me those questions in that meeting I almost froze solid then, only a slight smile from her allowing me to continue.

Then there is the dress that I am wearing. The fabric so soft, yet sensual, the material hugging my body, especially my breasts. When the salon first created them, it was a shock, but the reality had not set in. Now that some time had passed, my breasts were constantly sending messages to my brain about the situation down there. My nipples pushing against the material of the dress, the thin corset cup barely able to insulate the nipple from the sensuous material. Any movement on my part, just making the situation worse.

Then you have to consider my new vagina, my penis now concealed, leaving a void down there that is far from innocent. The panties I wore seeming to make the situation worse, the slippery nylon material of the panty sliding over my new vagina, sending little jolts of electricity throughout my body. I never asked, but I wonder how a false vagina could be registering and sending touches and movements of my panties against my bare skin. When I overthink my mind shuts down, all of these unanswered questions put aside for a later time.

Jennifer soon appears in a dress that is very similar to mine, only in a pale green color. Her endowments are obvious to anyone’s eyes, the cleavage just as enticing as mine is. I had looked down at mine after seeing her in the dress, comparing the two of us, she seemed to be more fortified than me, a pang of jealousy nagging at my brain. I had to think some pure thoughts, me a male being jealous of a woman’s more spectacular cleavage, what the hell is wrong with me.

Before I could figure a proper response to her looks, I am being led out to the limo. We are helped into the back seat and headed to the restaurant. Upon our arrival, we are shown to a private dining room, composed of only a few tables, the one we are seated at, had a breathtaking view of the river below. The restaurant built on a hill overlooking the river, this particular dining room seemed to be hanging over the river with little or no support.

We never received menus; Jennifer had apparently already ordered for us before we arrived. The meal is excellent, both of us receiving chicken fajitas with numerous accompaniments on the side to adorn them with. The guacamole and spiced tomato sauce are especially good. We are served Sopaipillas for dessert, biting off a corner and filling them with honey made them a delicious special treat.

The conversation at the restaurant very light and steering clear of anything regarding our business deal. She gave me a little of her history and her rise to CEO of her company. She seems extremely driven if any of her exploits are true. She wanted to know a little about me, what I enjoyed and how I ended up crunching numbers for a living.

I retold the story of how in college, I never did well in any subject other than math, statistics in particular. When I graduated a friend of my math teacher working for this company told him that he was looking for a statistician, the company getting big enough to require someone in such a position. I interviewed and was given the job just three weeks later. I rarely left my office, all of my involvement with the company being handled by email. When I was selected for this job, it was quite a shock, I am obviously in over my head, not just as a female, but also as anything other than a number cruncher.

Jennifer suggested that we go to her home, talk a little more about the contract, and then get some sleep. She promised me a safe and friendly environment, since it is getting so late, a trip back home tonight would be hard on me. I reluctantly agreed, and as the limo arrived, we then made our way to her home. To say she lives the life of some influential corporate CEO, a misconception after looking at her home. It is nice, a sprawling ranch house nestled on several acres of land. Not pretentious, not even a separate garage for the limo. The driver got our doors, and she showed me around the house. I am assigned a bedroom at the end of the hall, beautifully decorated with a spacious walk in closet. She told me there is some nightwear that should fit me in the dresser and a robe in the closet for me to slip over the nightwear.

She suggested that we meet again in her den when ready, and we could sip some wine as we discussed business. After slipping out of the dress, I found a nightie, silky and lacey it did cover all pertinent areas. Getting out of the dress was a chore, I don’t think my arms will ever be able to contort to the positions that a female normally uses in her dressing and undressing. I decided the corset stayed on, another layer between myself and Jennifer. The robe apparently matched, giving me a more modest appearance. I took a minute to send a text to Shauna, letting her know that I am still working on Jennifer, no signature yet, but I have still have hope. No idea on when I will be back in town, not everything going according to plan in this scenario. I turned off my phone; I really didn’t want a response to that text, fearful of answering any more questions that I am sure would be asked.

We did discuss business, she agreed to sign on the dotted line but wanted more time with me before she did the deed. When she saw me trying to stifle a yawn, she knew it was past my bedtime. She escorted me to my bedroom, then pushed me up against the wall and kissed me passionately. As fast as it had happened it ended and she told me we would resume negotiations at breakfast in the morning. There was a slight giggle and a smirk as she left me in the hall. I wandered into the room, removed my robe and fell into bed. Later, I had to get up and do the bathroom thing, but that was a nonevent and I am soon back asleep in the overly comfortable bed.

The next morning is unreal, my hair is tussled, my makeup is smeared, and my nipples are hard and erect. I panicked, not really knowing how to handle any of these problems. There is a knock on the door and a lady dressed in a maid’s outfit asks if she can help. Before I could respond she explained that Jennifer had explained the situation and thought that I might need a little help in making myself presentable. I stood aside and let her in, not comfortable with this, but the situation without her help would be much worse.

She sat me down at a vanity, put up my hair in a bun, then a shower cap to keep it dry. She handed me some makeup wipes and told me how to use them. She suggested a shower after the wipes, then she would pick me something to wear today. A look of distress came over me, I had not brought any clothes to wear today, figuring that the one day would be enough to handle any business. She scooted me off to the shower, telling me not to worry, everything is all right.

The shower is excellent, the pulsating jets almost making me wilt. I did manage to escape before I turned into goo, but barely. As I left the bathroom, Marie, her maid, had laid some clothes on my bed to put on. My other clothes had vanished so I had no other choice. I managed, although it took me quite some time to get covered up. It seemed at whatever I tried to put on turned me on, my nipples rock hard the whole time. Marie entered later, smiling at my appearance and telling me to sit at the vanity. She styled my hair, then helped me with my makeup, the items not in my purse she somehow had access to.

I wandered towards the kitchen, Jennifer intercepting me at the dining room. There were a few covered dishes present holding our breakfast. The food is excellent, and I was quickly too full since Marie had helped to refasten my corset making breathing and eating two subjects to be done only in moderation. I knew I had lost the self-assured part of my impersonation, so I asked Jennifer where we go from here.

She had again gained control of the situation, her shock from yesterday now a thing of the past. She suggested that we tour her company, letting me know a little more about her as a customer. I agreed and soon we were headed to one of her stores in her limo. At least with us visiting some of her stores, the possible relationship with Jennifer wouldn’t get any more exposure.

We did more than just walk through, I am introduced to some of her people and invited to ask questions. After the first two, I loosened up a little, asking some pertinent questions about their job and what they did. This continued for several hours as we visited three stores and one of their distribution warehouses. Here in this environment, Jennifer acted different, no longer the pushy CEO she treated her people like friends, real good friends. Quite often her conversation is about their families, their kids and if someone that was sick had recovered. We ate at a little diner, very unpretentious, but excellent food and a delightful atmosphere.

I had noticed that during the day, my attitude had changed, a little of the self-assuredness returning, but a sense of caring going along with it. I never once thought about the contract, about getting her signature, just enjoying my time with a friend and learning about her business. After lunch I remembered my job and told her that I needed to call my company and report my inability to get the contract signed. She told me we were heading back to her corporate headquarters and I could make the call there.

After arriving we went up to her office and she got on the phone. I soon discovered she had called Shauna, Jennifer telling her that she needed to talk with her boss about some aspects of the deal that still needed to be worked out. She had put it on speaker phone so that both sides of the conversation could be heard. I sighed, my inability to get her signature now a sure thing. I would travel back tonight, face the music tomorrow and then resign from the company. After a five minute wait our CEO got on the phone and asked what she could do for her. I kind of tuned the conversation out, I was aware of my failure, I didn’t need to be reminded of all the ways that I failed. Finally Jennifer handed the phone to me and I said hi, yeah a great way to start the conversation.

It turned out to be Shauna, asking how I am doing. I am alright, as soon as this is over I am going to head back. Thanks for having some faith in me, I am sorry for failing you. She giggled at me. “When you hang up you need to ask Jennifer to explain to you what just happened, listen carefully to every word she says. Then later tonight you need to call me so that I can talk to you intelligently, not this one sided conversation we have going on now. Thanks for all you have done, I don’t know how you pulled it off, but a lot of people owe you quite a bit.” The line went dead, I didn’t have a clue what she meant.

I looked over at Jennifer, the look that she saw on my face made her chuckle. “Let me guess. You would like to know what is going on, you have conveniently zoned out on me, your body is here but that is all. I have talked with your CEO and I have agreed to a ten year contract with your company for your products. I have made a few demands though before the deal can be put to bed. Your company has agreed to their part, now everything else depends on your agreeing to the deal. Since you have obviously not been listening, I am going to make you wait a little longer. We will head to my home and after getting dressed properly you will go out with me tonight for dinner and dancing. During the evening I will explain all to you and when we return to my house tonight I will ask for your decision.”

She leaned over and kissed me on the lips, leaving me breathless and confused, so very confused. I am led to her limo for the short ride to her house. As we enter Marie meets me at the door, and I am led back to my room. As we enter I see two other females waiting for me, with lots of things laid out on the bed and vanity. It turns out the ladies are from the local Turnabout Gurl Salon and they are here to make me pretty again. I am undressed and sat in a chair while they start on me. My nails are worked on, the extensions taken off and longer ones applied. This time a bright coral polish is applied, then my feet are handled in a similar manner less the extensions.

My hair is set in curlers, and a portable dryer is put over them. Forty minutes later the dryer is removed followed by the curlers. Makeup is next, all of my old makeup is removed, and then individual false eyelashes are applied making my eyes look as if they are peeking out of a forest of lashes. My earrings are changed, long dangly chandelier earrings are put in the lower hole, with diamond studs in the upper hole. Then a lot more makeup, with much more dramatic colors are applied to my face. I almost didn’t recognize me, the look very different from the business professional look of the last two days.

As the technicians fuss with my hair, I reflect back on my recent experience with femininity. It still feels strange, but not distasteful. The way people see me is so different, I feel for once that I can contribute to life some, instead of just going along for the ride. Jennifer still worries me a lot, her interest in me is scary, she sees something in me that peeks her interest, and her pursuit of that something seems relentless. Twice she has taken me to a fancy dinner, like she is courting a loving partner. I do have feelings for her, but am afraid to admit to them. All day today, I saw a different side of Jennifer, one that she doesn’t let out often, and one that her employees adore. I think I am in love too, with that same loving, caring person.

The image in the mirror brings me back to earth with a thud, a very sexy female, ready to take on the world. My hair is piled on top of my head with tendrils of my hair and ribbons escaping from the up do, and cascading down around my neck and ears. The effect is very feminine, but my hair and those ribbons rubbing my ears and neck are driving me crazy.

Marie helps me into the dress, if you could call that skimpy piece of material a dress. It covered much less than last night, I almost feel that my corset covers more than the dress accomplishes. The tops of my breasts are peeking from the top of the dress, actually only a few pieces of lace at the top of the bodice. The hem only a few inches below the bottom of the corset and relatively snug around my thighs. I gave a funny look at Marie, asking if she had another dress that actually covers some of my body. She smiled, telling me that Jennifer will love the dress and the person that is in it.

That is what I am afraid of, the technicians add another layer of lipstick to their masterpiece and they are off. I wondered what their services cost, I am sure it is not cheap. I am also curious as to who paid their fees, there seemed to be only one suspect, but she is not volunteering any information.

A few minutes later she comes to collect me, kissing me firmly on the lips as a greeting. I walk along, the towering heels making the walk a little difficult. The kiss has sent my mind into lock down, not a rational thought possible at this time. The limo is waiting for us, I am helped in and we head off in a different direction away from town. An hour later, we arrive at our apparent destination. The restaurant is very upscale, the cars I see in the parking lot all foreign luxury cars. The valet gets our doors and then the main door for the restaurant.

Jennifer is apparently known to the Maitre’D, as we are quickly led to a private dining room on the second floor of this establishment. A window overlooks the floor below, a dance floor situated right in the middle of the first floor, with tables situated around the exterior walls. There is strolling musicians working the crowd, and a few patrons dancing with their spouses on the dance floor. Light is by candles on the table and on the wall. All in all a very romantic place.

Jennifer orders for me, in French, so I have no idea what I will be getting. The wine is bought right out, she samples the choice, and then I am poured a glass. It is excellent, and I am even more confused. It seems she is courting me, we just met a couple of days ago, she essentially knows very little about me, I am dressed as a voluptuous female, breasts and a vagina included, but that does not seem to deter her. She reaches over to hold my hand and decides to fill me in a little before I go nuts. That statement delivered after looking at my facial expression.

“I told your CEO that I will sign a ten year contract with your company after they concede a few more things to me. I will give you a check for partial down payment on the first order to show my good faith. The check will be for a hundred thousand dollars, you can give it to your boss when you fly back with the contracts. They have agreed to my concessions, now the only thing remaining is for us to discuss where you fit into this picture. I have asked that they let you go, one of my main concerns that they have agreed to. As soon as you deliver the check and contracts you are fired, essentially unemployed.”

At that point my mouth is open, my jaw hanging down farther than usual. Fired, I do all of this and I get fired. Never mind that I was planning on quitting, surely they can’t do this.

“That is good, because I want to hire you to work with me. I need a COO for my company, a job you will have if you sign on with me. There is one hitch, you have to live and dress as a woman for the job. There are fringe benefits, a pension plan, medical plan, paid vacation, and stock options. Now will you sign on or do I have to use my trump card.”

I stuttered that I need more time, I am still processing the ten year contract and the hundred thousand dollar check. The getting fired bit also trying to derail my thoughts. My mind has not put anything else into the data entry port yet. Then I sucked in a huge breath, “I have to live and dress as a woman, I can’t do that.” Jennifer giggled, you are almost there, keep going and I will let you know when you get to the answer.

I shut up, I need to think for a while, this is so confusing, maybe someone can look at what is happening and explain it to me in a way that I can understand. She is going to sign the contract that is good, exactly what I was sent here to accomplish.

I am going to be fired from my present job, a condition from Jennifer for her agreement to the contract. I get the deal completed, how I have still not figured out, and I am let go. All because Jennifer wants it done. Well the jury is still out on that one. All I can see is disaster for me.

The she offers me a job as her COO, a job that I doubt I even know what it entails. I handle numbers, a blasted number cruncher and she wants me as an executive. Some body in this scenario might need some intensive counseling.

Then to accept the position I know nothing about I have to live and work as a female from now on 24/7 for the rest of my life, or until I get fired again. That a more likely outcome. This all came about as a test to see if we were committed to our company, a test that I think I have passed, but to change genders permanently that is a lot to ask. I learned enough to get by for a day or two, now I am expected to do it full time. Surely the world as I know it has gone mad, stark raving mad.

With a few brain cells connecting I tried to reason with her. Even that thought sounds ridiculous when it is said out loud. “Look Jennifer, I am a poorly adjusted male living alone, have worked my whole life doing statistics, I don’t even have a pet, because it would probably starve to death in my care. Now add all these hoops that you have made me jump through, you have got to be insane to think that I can help run your companies. I will take the check and contracts back, then I am resigning my job, and after sufficient time to let the goo in my brain leak out I will start again in some other field.”

“I have enjoyed being with you, underneath your harshness you are beautiful, caring person who your employees seem to love and cherish. I am just not the person you think I am, and being out of your life is a better option for both of us.”

I looked at her face to try and see if she is mad, angry, or just numb. We ate in silence, her not saying a word to me, although she frequently looked at my face. I put my fork in the chicken salad that was served me, it tasted wonderful, but my appetite had left along with the conversation. I did drink several glasses of wine, to numb my senses a little. She paid the bill and we left, still no words between us. I knew I had fouled everything up, I could picture in my mind her tearing up the contracts and the check that I was supposed to return to my company. The limo ride is in silence, with me looking out the window as we traveled along. The scenery seemed different than on our trip here, maybe the driver is taking another way home.

When we arrived at the airport, I knew that I had blown it big time. She is getting rid of me, sending me home right away with nothing to show for my time. We pulled alongside my company jet, the pilot warming up the engines. She faced me, making me look directly at her eyes.

“I am only going to say this once, are you listening to me Debbie?” I nodded my head, but she wanted me to say the words.

“Yes, Jennifer I am listening to you.” The tears were ready to cascade down my cheek, I have cried more in the last two days than I have in my entire life.

“Here is the contracts, and the check, I keep my word. You will fly back present the contract and check, and work out a means for our two companies to work together. As of this moment you work for me. No backtalk, just nod your head in the affirmative.”

I start to say something but she place her finger on my lips. “I will give you two days to conclude that business and wrap up your affairs, no more. You need to get focused and concentrate on getting things wrapped up. Gather up any personal momentous you desire to keep, leave all your clothes and any furniture behind. You can give it away, you will have no need for it here. This is Wednesday, on Friday night my corporate jet will pick you up and return you to me.”

“We will spend the weekend planning the handling of your job and position, then several days shopping for your new wardrobe. A couple of days at the office for you to get your feet wet, then next Saturday we will fly to some romantic destination for some R and R.”

She got down on her knees and took my hand and slid an absolutely gorgeous engagement ring on my ring finger. “To help ensure that you will return I want your word that you will marry me. I am not in a rush, I know that this is quite a bit to get accustomed to, but I love you and want us to be together the rest of our lives. If you can’t agree tonight, I will wait until you do. Your only choice is with me and I will pursue you to the ends of the world to get my way. Until then wear my ring as a reminder that I love you and your rightful place is with me”

I was speechless, I could smell the smoke coming from my mind, totally overloaded with questions, feelings, and emotions. She is looking at me for some decision, one that I haven’t even figured out the question for. To stall for time that I desperately needed I told her I would fly back Friday and we will talk some more. That seemed to appease her some and I received a kiss that defied description. Another short one and she turned me toward the jet and I walked to the stairs. Maybe my heels were touching the tarmac, I had no idea if they were and couldn’t care less.

I don’t remember a thing on the flight back, I am not sure if my mind is even working. As we were slowing to make the approach to the airport at home, I sort of came to and looked at my appearance. I grabbed my purse and fixed my lipstick, finding the check and the contracts in the purse along with a short note.

It was from Jennifer, take time and decide what you will do, my offers are genuine, and heartfelt. I want you so much that I will continue my pursuit until you agree to be mine. Whether it is now or in ten years’ time I intend to make you mine, treasuring and caring for you the rest of our lives.

As we rolled to a stop I saw our limo and Shauna waiting for me. I checked myself in my mirror again, then got up and made my way to the exit. I climbed down the stairs, and was attacked by Shauna, obviously very glad to see me. She took a good look at me, making the remark that she loved the dress. My instant red color blending well with the red color of the dress. She checked me over very carefully, she noticed the longer nails, and the slightly different hairstyle I had been given, all things a female would notice.

I was dragged back to the limo, getting into it a little more difficult than I imagined. I presume that our limo is maybe not as spacious as Jennifer’s. Shauna was bubbling over with questions so she suggested we find a quiet place to eat where we could talk about all that had transpired.

We went to a restaurant just down from our offices, busy during the lunch hours, but usually uncrowded later in the day. We were shown to a table and I prepared myself for the questions that I was sure I would be asked. Shauna noticed the ring first, grabbing my hand to get a closer look.

She looked at me, “you have some explaining to do missy, I send off a young male dressed as a female to try and get a contract signed with a person used to getting her way. On the return trip I see a female get off the plane, confident, assured and obviously engaged. What the hell happened? Are you going to ask us to be in the wedding, you better if you know what is good for you?”

I stammer an answer, inadequate as it is. “I am not sure, she asked me to marry her, also to be her COO of her company. I am confused, bewildered and in love. She is totally different when she gets away from outsiders. Her employees love her, she knows most of them by name, knows about their families, and cares what happens to them. I know I love her, but she wants me to be a female 24/7 from now on.”

“We get along great, she treats me well, and constantly buys me things, but when we are alone the way she cuddles me, holds me, kisses me, makes love to me, just makes my heart soar. We have not done the deed, just kissing and cuddling more than enough for me at the moment. I realize I am a male, but around her I am her companion, lover and probably soon to be wife. I am so confused, when she is near me I am like putty in her hands, so you tell me what do I do?”

Shauna smiles. “Stupid, you marry her. Now answer my question do we get invited to the wedding or not.” I nod my head, but also start sobbing. What am I going to do, I do love Jennifer, although it has only been a few days. Being a woman from now on does have me concerned, probably unnecessarily since for the last two days I have been dressed and acted like one with very little difficulty. Shauna took a couple of minutes and texted Beth and Katrina to meet us at the office as soon as possible. I was still trying to compose myself.

We took a taxi the rest of the way, walking up to reception dressed as a female not as a male hard to get used to. They had a new name badge for me, so that I could get around the office without hindrance. Beth and Katrina met us at reception, giving me big hugs and admiring my ring. They had lots of questions but Shauna told them that we were expected at Beverly’s office so we had to get going. We went right up to the CEO’s office and was shown right through. I had never even been to her office in all of my time with the company.

I took a seat as offered on a couch with seats all round a coffee table. Shauna set next to me, Beth and Katrina set next to us on wing back chairs. Beverly sat opposite us, smiling at my appearance. I retrieved the check and contracts from my purse and handed them to Beverly. She looked them over and her eyes widened at the size of the check. She looked over the contracts to see that they were signed properly, then set them aside. “I thank you for your diligence in the matter, but I want to know more about Jennifer’s request that you be let go immediately. That is not how we reward our employees who bend over backwards to help us in the marketplace.”

I decided to tell her everything, the truth is better than me trying to figure out some way to get around it. After I had disclosed everything, she looked at me. “What do you want from this, I know what Jennifer wants but how about you.” I pondered that for a while.

“Whether you fire me or whether I resign, if you want to keep the contract we need to part company. Also while I am here I need to work out how the contract is to be monitored and handled. Since I am the new COO of her company and you will need to deal with me on all matters relative to the contract.”

I hear four sharp intakes of breath, then some giggling. I am trying to keep a professional atmosphere her and they are giggling. Shauna sums it all up. “We send Debbie to get the contract signed, she accomplished that easily way above any expectations, then comes back to resign her position since she is now their COO. Then we find out that she is going to be wed to the customer soon, another phenomenal feat. As she is handing over the contracts and check from the deal she starts negotiating with us on the terms and conditions of the contract she just delivered.

“Debbie as a number cruncher was a waste of her talents, I wouldn’t be a bit surprised that she soon takes over Jennifer’s company to run it as she sees fit. I think we need to concede defeat here. Debbie anything you want you can have, any terms, any conditions without reservations. Beverly do you agree?”

“Put your requests on paper and I will sign them. Our company is indebted to you for your efforts on our behalf. For that we thank you. Now that is out of the way where did you get that dress, it is simply gorgeous?” That got a laugh from everyone present. I told her where it was purchased, Beverly writing down the name of the boutique Jennifer bought it from.

“I will have a list of my requests emailed to you in the morning. Of course, I insist on Shauna, Beth, and Katrina as the only people I will deal with. I have nothing against you Beverly, but I know the three well and feel more comfortable dealing with them.” As we were getting up to leave I got a big hug from Beverly and a sincere thanks for all you have done for our company.

With that the four of us left Beverly’s office, and headed to Shauna’s. I had to fill the other two in on all the goings on, but we had a good time discussing how this had morphed into such a monster, all because of Jennifer. Shauna gave the other two a signal somehow, and they made their excuses and left. Before we left the offices I told Shauna to split my percentage for helping with the deal three ways, I doubt I will ever want for money so it should go to my BFF’s who helped me through this. I received such a hug, probably cracked a rib too, as hard as she was hugging me.

I could barely keep up with Shauna as she headed for her car. Some light chatter between us on the way to her home, then promptly inside and with some wine seated on her couch. “Now that we are away from prying ears, I want the lowdown on what is going on. Not what you told me at the airport and restaurant but what is going on inside that cute little head of yours. Now spill.”

Instead of talking I started sobbing, the tears seemed to go on for some time, easing up at times then I would look at myself and they would start all over again. I finally ran out of material for the tears, and just sat there staring at a spot on her floor. She gently raised my chin, making me look her in the eyes. I hugged her tightly. “I don’t know what is happening to me, since I spent some time with Jennifer I have been totally incoherent.

Before this I thought I was a fairly normal male, lonely for sure, but still a male. Now I can’t wait to play dress up, new clothes, a different hairstyle, makeup, jewelry all making me weak in the knees. When Jennifer is around that is all I can think about, her kiss, her holding me, our cuddling in bed. It is driving me mad. Right now I am wondering what nightgown got packed in my suitcase for tonight, then what I am going to do about my hair in the morning. My nipples are getting hard just thinking about it. Talk about being messed up, I am way past being a basket case.

Shauna took it all in stride, “it sounds to me that a female is now occupying your body, what you have described is typical of a woman in love.”

“But I am not a woman, I plead guilty to the in love part, I seem to be hopelessly in love. I admit I look like a woman, but underneath all of this disguise I am a male. How can I just switch sides and work and live a female as though it is just another day at the office.”

Her reply quite simple. “Why can’t you be that female, if you look the part, you can do anything you want? Your inner being is certainly female, when this first started you were not against it, like a normal male would be. You allowed the changes, but quickly took command of the situation. You had a plan, made sure we gave you the necessary support then flew out to Jennifer to do battle. How you accomplished the feat makes no difference, you did make it happen. Then you allowed yourself to be swept off your feet by her, coming back with a ring and a proposal of marriage. Now tell me how many males would even allow that conversation to start, much less be wearing her ring on your return.”

“Now let’s talk about the wedding, I want to be included in the wedding party or I am going to hurt you. It is a big day for a female, her future, her significant other, and her life all culminating in the ceremony. Do you want a big wedding or are you going to slip out to Vegas to tie the knot?”

I told her what Jennifer had mentioned, but no decision has been made, I am not even sure I am going to marry her. Shauna hauled off and hit my arm hard, “there will be no more talk like that, do you understand?’ Rubbing my sore arm I nodded my head, if I do turn Jennifer down I may need to learn some self-defense quickly. Three against one is not very good odds.

She convinced me that the only sensible course is to follow my heart, that means finish up here and fly back to Jennifer. She insisted I stay with her tonight, furnishing me a quite risqué night gown to wear to bed tonight. I got lots of hugs and then we retired to our bedrooms.

She would take me back to my hotel to get changed and then to the airport in the morning. Jennifer had already figured out that I would accept and had the plane waiting at the private jet hanger waiting for my wish to fly back. I handed the girls my demands as to distribution, then assured all of them a place in my wedding party if they so desired. As we departed at the hanger I told the girls I would be in touch, and then climbed on board her company jet. Lots of hugs, tears and kisses were exchanged, before I walked up the ramp as the engines were started. I spent the whole flight thinking about Jennifer’s and my relationship, I did love her that is for sure, but being a female 24/7 still made me pause.

When the jet landed the limo was there to pick me up. I was taken directly to her home, a maid taking my bags and leading me to a bedroom upstairs. As she unpacked for me, I changed my dress, freshened my makeup then made my way downstairs. I was greeted at the entrance to the dining room, Jennifer smiling from ear to ear. The kiss that I received was indeed toe curling, twice I had to stop and take a breath before I was able to resume the kiss.

Finally the kiss temporarily ended and she asked if I was hungry. I asked that we talk first, then eat later. I was dragged to the library, a big soft comfy sofa to be our discussion spot. I took a few moments to gather my thoughts then started. I told her what we worked out at my old job. That I had indeed resigned and was available starting tomorrow. I asked what my duties were to be, half way through the question she stopped me. I want you to run the companies as you see fit. You are intelligent and I have faith in you. If you want help I will be glad to answer questions for you on what we have done in the past, but I will only allow a question or two to be asked. I am paying you the big bucks for your expertise, so you need to impress me. You name your own salary, just make sure it can be handled within the overall budget.

Now I have the limo for you to use, Steven will be yours for the duration. Marie is your maid she will see to your requirements and the care and maintenance of the house. I will see to the care and maintenance of you, so expect to be pampered and cared for by little old me. You will have to reserve lunches and dinners for me, when I am in town, your job can not interfere in these matters. I am going to be starting a few new business entities, something for you to play with later in the year.

Once she wound down it was my turn to speak up again. “I love you with all my heart and I will marry you but I want to have some time to enjoy the dating, the romance and the loving before we tie the knot.” I slipped off the engagement ring, giving it back to her to hold for later. Well, she wanted nothing to do with that.

“Wear the ring, we will just arrange to have a long engagement, a year maybe, depends on whether you get with child and I have to make an honest woman out of you.” I giggled, but she kept her straight face. I let it drop, surely I can’t get with child, can I?

I asked again about me being her COO. I have no experience, crunching numbers not very good training for an executive that runs a business. Surely you have someone more qualified to do this job. “I have picked you, and that is final. You do have the most important qualifications for the job. You care, are sensible and will do what is necessary to complete the job. End of discussion. Now Steven will take you to each store or warehouse unit, for you to meet the people and see what is going on.”

“Any crisis will be made known to you, so that you can handle it, otherwise keep with getting to know the people and business. With the products from your company, introduce them slowly, allowing our customers to know that we now carry them and for your company to get used to our volume.”

“Remember lunches and dinners are mine, so keep those times for me. I will let the marriage slide for a while, you will live with me and sleep in my bed though, and there is no discussion on that. Your closet is stocked with clothes, and the first stop every morning will be the salon so that they can be sure that you are beautiful and ready for the day. After you accept your status in life I will allow you to do your own hair and makeup if you want.”

“Now what else has to be negotiated tonight or can we eat.”

“First I need a kiss real bad, then a lingering hug, after that food will be fine. I love you, it is just that all of this is so new and different. I am scared one minute and terrified the next. I will try real hard to please you, but still wish you would reconsider the COO position. I feel so inadequate, maybe I can learn to live as a female 24/7, but run a business is so scary.”

I got the kiss, the hug felt so good, lasting for quite some time. I was dragged to the dining room, a single covered dish at each of our place settings. She helped me with my chair, and then kissed me again on the lips. As she backed away she lifted the cover to reveal a hamburger, with curly fries surrounding the burger. I grabbed a fry right away, it was so good, and then a bite of the hamburger, the juices running around my lips as I tried to lick them before they got away.

Then I did something so unexpected, I got up from my chair took my plate and set it down next to hers. I plopped my rear end on her lap and kissed her so hard. Then quickly turned back to get another bite, the rest of the meal was a kiss, a bite, then another kiss. All the time I was twisting my fanny on her lap, I knew it was bad, but oh so much fun. It was almost an hour later when the burgers were finished, my head laid on her shoulders my face nuzzled into her neck.

The evening was wonderful, after dinner we cuddled first in the living room and then we moved our efforts to her bedroom. I was held tight, my head kept on or near her breasts all evening. Lots of kisses were exchanged, about three AM I finally succumbed to sleep, Jennifer still holding me tight to her. I woke to kisses and when I didn’t attempt to get up she attacked my nipples through the nightie, I knew I had some feeling there, but one tongue lick had me moving quickly to escape her mouth. My nipples are rock hard, goose pimples attacking my whole body relentlessly. Her smirk was back, as she crawled across the bed to get to me. I backed away, giggled and ran to the bathroom, closing the door in an effort to evade her pursuit.

We spent the entire morning playing cat and mouse, my feline soulmate prevailing most of the time. That is how I viewed Jennifer, someone who saw what she wanted inside me, and would not settle for anything less. I suggested we do something business like for the afternoon, since we played all morning. She made a few phone calls, while Marie helped me get presentable. Gawd, so much to get used to, but if I admitted to my true feelings, something that has been missing my entire life. To get a break from Jennifer’s antics, I arranged for Stephen to take me to a couple of the store branches.

The ride was quiet, time to reflect on all of the things that had happened, without someone’s kisses distracting me. I came to the conclusion that maybe I could do this, a new life, a new job, but one filled with lots of challenges and excitement. As we came to the first stop, I got my lipstick and my mirror out of my purse, needing to make sure I was presentable, a COO always needs to look good. The manager of the location met me and we walked the store meeting the employees and discussing any relevant problems. I actually saw a few things that would improve sales and mentioned them. I think the manager was a little embarrassed, the things I mentioned were pretty basic and should have been included routinely. The second stop was almost the same, although my suggestions were in a different area.

Jennifer met me for dinner, at one of her favorite eateries. I was hugged real hard as soon as she saw me and taken to her table, my hand firmly in her grasp as she pulled me along. She started in on me right away, mentioning the two store managers I had met and their respect for me after our meeting today. I had pointed out to them some improvements, but not made an issue of it. After they had implemented the changes they realized they should have been doing it all along. Both managers called Jennifer complimenting me on my tact and skill in business matters, an excellent choice for a COO position.

Now that we know you are capable of doing the job, I expect great things from you, both in business matters and in the bedroom. Making more money to invest into other businesses, now that I have a capable manager in house, means the sky is the limit. On the ride back to our house after dinner, I was sexually assaulted in the most wonderful and diverse ways. It continued once we were in the bedroom, but this time I insisted on an early bedtime, since I had lots of stores to inspect and manage.

Maybe it won’t be too bad, something to keep me occupied, wonderful clothes to wear and a lover that seems to be insatiable. To think I thought a career in the numbers game would get me nowhere, instead it got me into dresses, makeup, and lingerie, then the rest was history. Asking a lot of someone, but well worth the time and effort. One look at Jennifer, it was well worth the effort.

Story Complete For Now

© 2016 thru 2021 Fran Cesca Walker

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