Donna; Paybacks Can Be A Bitch

I had built my realty business up from a single office to well over three hundred offices, now I needed to sell the business or find some investors badly before I had to declare bankruptcy. The recent downturn in the economy had hit my company hard, causing me to curtail activities severely. It had not reached the point of laying off personnel yet, but another couple of weeks without an infusion of money would make that a necessity. It wasn’t because I wanted to sell it, quite the opposite. To keep it a viable business I had to get some cash infusion, either by selling the whole business or some part of it.

The economic downturn and the resulting loss of so many jobs took away all of the expendable money our prospective customers had, making them stay in their existing homes and not trying to upgrade. Business transfers were non-existent since companies were laying off people by the hundreds. If anybody had some equity in their home, they were stupid to move or sell, the resulting situation far worse than the original. Mobile home sales were up, since that is all most people could afford if they were moving away from renting. Even apartment complexes were having trouble, several of them having to greatly reduce their rents to keep their property at the break even point.

I should have cut back sooner, when I first noticed the change in the market, but I wrongly guessed that it might bounce back. Instead it bounced farther down, but now I had less capital to weather the storm. I had even contacted a lawyer, concerning filing bankruptcy, something I dreaded doing, but the only way to salvage anything from the company. We talked about many different solutions as he filled me in on what was possible and the side effects of going that route.

My accountant and I explored every possible option making sure we had not overlooked a possible solution to my problems. My accountant mentioned an investor that she had done some work for in the past that might be interested in acquiring a share of the company, so I asked her to contact that person and arrange a meeting. A one in a million possibility but worth the gamble at least that was my thinking.

Let’s face it I was becoming desperate. I had mulled over every conceivable solution, finding fault with most of them. If I went to a bank the first time they looked at the books, would be the last time I would be considered. Too much payroll for the amount of cash coming in would be the first statement out of their loan officer’s mouth. If I started laying off people right and left to make it feasible to continue, the rumors would start and soon my few good people would be seeking employment elsewhere before the company closed its doors. I knew of a friend who did that to try and salvage his business, it was liquidated in bankruptcy a few months later.

Imagine my surprise when Rebecca showed up at the arranged meeting a week later. The meeting was to be in my office, at ten A.M. I almost swallowed my tongue when she walked into my office. She sported a huge smile on her face, apparently she knew who she was meeting, while I was left in the dark. Maybe for the better, no telling what I would have done if I knew she was the possible investor.

Rebecca and I dated in college, back when I thought more of myself than I do now. Let’s face it I thought I was hot stuff and deserved any and all attention. The cockiness of my college years got knocked out of me by real life. Unfortunately, when Rebecca decided to date someone else I made quite a stink, both with her and her intended. It even made the college paper, not front page but still predominantly displayed for all to see.

Back then Don was fairly arrogant, his opinion of himself quite different from anybody else. Unfortunately, I was that male named Don, college age, but still a teenager in maturity. Rebecca’s and my relationship wasn’t the only one I fouled up; I managed to poison most of my family too, a sister the only one to come around later in life. By the time I had finished college I had lost all of my friends, either by pissing them off or by them avoiding me, my reputation preceding me.

When I saw her I figured the arranged meeting was a waste as our parting of the ways had been rather hostile, mainly because of my big mouth. She was cordial, which surprised me greatly. We discussed the company, she looked over the P and L statements carefully, then looked at the organizational chart for the company, showing managers and employees at each branch. We discussed her investment and how the ownership would be divided. We agreed on a tentative purchase agreement, dependent on her accountants going over the financial details of the company. Rebecca would have a fifty-one percent share in the company, although I would continue to run the company. Truthfully I was in shock, surely this can’t be the same Rebecca that I had jumped on back in college.

As we got ready to break up the meeting, she asked if I would join her for lunch. That was even a bigger surprise, since I was sure she would want nothing to do with me. I agreed and we drove her car to a restaurant just down the street. I figured the lunch wouldn’t last long and I could walk back to the office afterward. As she drove there, she asked how I have been doing other than the business.

“I’m about the same as before, too busy with the business to date, and recently worried how I’d be able to salvage it” I replied. I thought about stretching the truth some, but decided to just be truthful and let whatever came to be just happen.

As we pulled into the parking lot I asked about her. We went into the restaurant and were seated over in a corner before we could resume the conversation. It turned out that she was doing pretty good, owning six businesses now, none of which had been affected by the downturn so far. When she heard about my company looking for an investor she was definitely interested.

She was looking for new commercial locations for several of her businesses, so a real estate company might be the perfect solution to attain these properties and also manage the locations she currently owned or leased – some five hundred properties across several southern states. It seemed that many of my offices are in the right areas to be of service to her. I was a little shocked to learn that she had a bigger business presence than myself. I knew she was smart, one of the things that attracted me to her in the first place back in college. Her success pointed to something else, being smart and developing a huge business presence do not necessarily go hand in hand.

We took a couple of minutes to order our lunches, then resumed our discussion. So far it had been cordial but strained, at least on my part. I expected fireworks at almost any minute; surely she couldn’t have forgotten our conflict back in college?

The meal was served, we nibbled making small talk in between. She picked up the check, but wanted to talk a little more before we left. I forced myself to swallow what was obviously stuck in my throat, since I feared what was next was the hard pill I might be forced to take.

“I’ve had my accountants already check out your company, so that’s just a formality. The deal is satisfactory for me as it stands, with a couple of minor revisions – both of these will have to be inserted into the contract.”

She continued as I listened, “I want you to continue to run your company with my guidance, since I will now have a 51 % interest. The next condition I’m sure you will not like but it’s non-negotiable. I’m sure you remember our parting during college. Well, I was greatly embarrassed by your actions towards me and my intended boyfriend. He left me soon afterward, the press and the talk on campus convincing him that a relationship with me was not worth it.”

I tried to apologize to her, since my actions were wrong and mean. I was ignored and when I finally shut up she continued.

“I eventually recovered; maybe what you did caused me to work harder to excel. The loss of the boyfriend may not have been such a bad thing if his later activities are anything to go by. Anyway I did manage to make something of myself, but vowed to make you understand how much you hurt me, how you humiliated me in front of my friends and family, so here it is. The second condition of the deal is that you will perform your duties as CEO of your company as a female, that is as a complete female. Maybe then you will better understand how your words hurt me so bad. I want you humiliated just like I was, and not just for the short term.”

I looked at her, my mouth open wide, not a word possible to escape its depths. Up to that moment I never realized what I had done to her, how much I had hurt her. I just sat there running all of this through my mind. If I said no, I would probably lose my company, but worst still it would be my failure as a business manager, making getting a job afterwards very difficult no matter what the reasons for the failure.

I listened as she said, “As a female you will be faced with the hardships most women have to go through to be able to do the same things as a man. I intend to make the transformation known to all, for all to see that you no longer are a male, now just a lowly female doing the work, but not getting the rewards accorded to a male. You will still have enough money to live a comfortable life, but not what you are presently pulling as a salary. After a couple of years we will talk about it again, so there is still a small hope for you to return to the masculine. Now do you want life as a female or do you want to declare bankruptcy and take your chances on a future clouded with past failures?”

She knew she had me over a barrel; if I declared bankruptcy all that I had invested in the company over the years would be lost, a quite sizable sum of money. In the few moments that I had a chance to think about it, I figured me as a female would be ludicrous, the new persona more of an embarrassment to the company than to me. At that point I figured she would end the charade and let me return to my masculinity.

I therefore relented and told her the terms were acceptable. She smiled and held her phone towards me, making me repeat my acceptance of her terms. Next, stating that I wanted to be a woman in the job, I had to plead with her to allow that request. I am sure when she revealed all, that last video would be played in its entirety, putting all the desire for this to happen on my shoulders, leaving her blameless. I almost choked on the words, something I never foresaw saying to anybody, much less Rebecca.

“I intend for you to be a girly gurl, wearing only the frilliest of clothes, date men, join all the ladies organizations, everything that a female wanting to advance would do. I want you networking with other females, helping them in exchange for their help as you try and run the business. I am sure that I will get enough satisfaction at knowing how humiliating this will be for you, a proper payback for your behavior towards me in the past.”

I saw something in you years ago, and now I want to see if that surfaces again. We can sign the deal tomorrow; I’ll transfer the funds needed to keep your business afloat that same day. It’ll be yours to run as you see fit, though I want to be consulted on any major decisions. Your transformation appointment is this weekend, Saturday at seven AM. They’ll have you looking female before the weekend is over, so you’ll be able to start work Monday morning as your new self. Plan on staying at the salon; this particular one has accommodations for its customers and I’ll be there Sunday at five to pick you up and take you home. There is still some compassion towards you left in me, but I need to see you feel what I felt before anything can be rectified.”

She got up, paid the check and walked out. I noticed she didn’t even look back to see how I was taking the revelation. Badly if my facial expression is any measure of my mental state. My mind had shut down, too much that I didn’t have any idea about, much less what to do about it. Oh shit, I thought, what have I got myself into? Don’t answer that, I couldn’t even fathom all of the ramifications of such a deal.

I walked slowly back to the office thinking of how this was going to work out, and what I would be facing in the next few days. I decided business first – sign the deal and correct the few things that need immediate attention. I needed to go ahead and make some changes, streamlining the offices a little more, keeping the expenses more in line with the income we were receiving. I made notes on what Rebecca might need as we took over managing her properties, also getting several of my agents looking for possible properties for her businesses, especially those that are priced right.

I walked home that night, a distance of a little over two miles. The weather was good, and I needed the time to think things through. I almost walked by my abode the first time, looking up to see that I was already well past my residence. Arriving home, I really didn’t come to any conclusions, but I did consider several possible ways for me to cope with this. Time would tell which one I would choose and if the decision was the right one. It was quite a decision, one that will have far reaching effects, no matter which way I approach it.

I tried to zone out, forgetting what awaits me on the weekend. I cleaned the house some, made myself a snack, and then watched some TV. My mind wasn’t on the TV though. I hadn’t the slightest idea what shows I watched that night. It was just noise in the room filling in the otherwise quiet house. I ended up falling asleep in the chair I am sitting in, then rudely awakened when the TV went off making that buzzing sound it makes when there is no reception. I flipped it off, carried my dishes to the kitchen, and then staggered to the bedroom. It was like I was in a bad dream, one that I couldn’t wake up from. Half of my mind seems to be on vacation and the other half doesn’t have a clue to what is going on.

Before I fell asleep, a notion entered my mind and a smile appeared on my face for an instant, then rational thought took over and I doubted I could pull it off, much less have the nerve to try it. Apparently what little sleep I got was very restless, waking up with my sheets wrapped tightly around my body. It took me several minutes to extricate myself from them. When I reached the bathroom, I had only moments to spare as I quickly settled on the toilet. The notion from last night made another brief appearance, but getting to work took precedent. Since I had walked home I had to walk back, since my car was still at the offices. I needed the time to think last night, the walk this morning proving that it wasn’t that hot of an idea. Considering how little I accomplished last night as to what I was going to do, it was time wasted and only made this morning much worse.

As I entered the realtor’s office, there was not much said; I presume the rumor that I had sold part of the business to keep it viable had made its rounds already. When I got to my office that is the first task. I sent an email to everyone notifying them of the changes, the proposed closing of the deal today and the changes that will affect everyone. On a whim I inserted in the email that there would be some changes in management, that announcement going out in the next day or two.

I had everything set up when Rebecca came in at eleven. The contracts were written up, I had sent her attorney a copy and I had forwarded a copy to mine. All of the specifications she wanted were clearly stated, no legal mumbo jumbo, and ready on my desk for her to sign. She read over them carefully again, but did tell me that her attorney could find no fault with them. My attorney thought I was nuts, especially her two clauses, but I assured him they were fine with me, an explanation to follow later for me accepting them, an explanation he definitely was looking forward to hearing.

After signing them, she showed me a deposit slip from my bank where the money had been deposited. I made copies of everything, every piece of paper, the deposit slip, then shoved one more piece for her to sign. I told her it was just between her and me, a simple statement that my portraying a female was her condition for the deal to be put together. She gave me a look, but signed it anyway, I made a copy for her, and put the original in my wallet.

As she got up ready to leave, I asked her if I could move up the salon appointment some, I need a little practice if I am going to look business professional for work next week. I got another stare, this time a more deeply evolved one, trying to see what my game was. She didn’t find the answer she was looking for, telling me to call Dallas at this number and handing me a salon business card. As she was leaving. I immediately went to the phone to make the call.

I dialed the number and then asked to speak to Dallas. There was a short wait and then she answered. I told her who I was and would like to move up my appointment from this weekend. She suggested that I come in now, we could talk, and while I was on my way to the salon she would look to see what vacancies are available. The drive to the salon is about thirty minutes, arriving shortly after eleven AM. The meeting and signing this morning had taken very little time so I had a little extra time that was not expected.

We greeted each other in front of the salon at their reception desk and I was taken to an office in the back. I told her what the situation was, and what I wanted to do. She told me that they took the appointment, but do not perform their services when revenge is involved. My Saturday appointment was based on my consenting to the procedures willingly and signing an agreement to that effect. I had a lot more respect for the business after she revealed those conditions.

I reiterated what I wanted and why, I did abuse Rebecca greatly, hurt her more than I wished. Maybe if I go overboard on this, her mind will see that justice had been done and we can get back to a civil relationship. I doubted it could ever be close again and having any kind of love in this scenario is probably absurd.

It turned out Rebecca had insisted on some feminizing treatments but not the full feminine experience. I would no doubt look feminine, but maybe not totally passable. If I was going to have to run the business as a female I wanted the full package. That was relayed to Dallas and she made the changes necessary. Dallas quizzed me several times, making sure that I had thought this through. Then she made me sign an agreement stating what I wanted and the reasons for wanting it.

“When do you want to start? I have an appointment right now, you will be female in looks before eight tonight, then some classes to make sure you can handle the day to day about being female tomorrow morning.” I agreed and soon Jessica was leading me away. On the way to the treatment room, I had several second thoughts, but knew in my heart that I needed to put them aside and square things with Rebecca, or at least try to get things back to a normal relationship. Just considering those thoughts I realized how far this had progressed. I was going full female and expecting to pass as one, even though I am a male and been one for quite a few years.

I did manage to call my office, telling my secretary about my appointment and that I wouldn’t be in till tomorrow noon at the earliest. I got some giggling, her demanding a picture tonight so she would be able to recognize me tomorrow when I came in. Since she had written up several of the agreements she knew what was involved and what I was doing at the salon. She was having way too much fun at this but I consented to the picture, better to get over her laughing fit now rather that tomorrow in front of the whole office.

From what Dallas showed me, I would be 100 % female in looks and somewhat female mentally. Adding boobs and a vagina plus long curly hair, and smooth hair free skin did make the former male think and act differently. I swallowed hard, the moment is here as I was led into the room and told to strip off my clothes. Just think tonight my clothes will be something different, maybe I can get an outfit in apple green, a favorite color of mine. It is surprising what inane thoughts the mind thinks up when it is approaching insanity.

Jessica had a different time frame in mind for me, within thirty minutes I was hair free, a cream left on my skin for a short time and then wiped off left me bereft of any follicular development. Another painful twenty minutes and my eyebrows are eliminated, no cream this time a pair of tweezers and soon there was a thin high arched line above each eye, but in the bright light it was not visible, the few hairs that were left in the thin arch barely noticeable. They were left that way so that I would have a template to pencil in my eyebrows to go by. Each change so far affecting my looks quite dramatically. The eyebrows, or lack of, left my face decidedly feminine.

Next slipped into a funny looking chair similar to a dentist’s chair and leaned back. My head now over a sink, with just my neck and lower hairline supported by something. Then I felt my feet being lifted into some form of support and then spread wide apart. My arms finding their way to the arms of the chair and secured. I started to say something, this is moving faster than I had in mind, but a mouthpiece slid into my mouth, for the purpose of whitening my teeth made speech difficult. Oh well the sooner it is over with, the better. To think that a former male could even think those words. I relaxed my head some, then felt the warn water flowing over my hair.

At the same time someone moved between my legs and started moving my male member around, a cooling spray landing on the area and then nothing. I felt two objects being set on my chest, apparently glued to my chest since I could feel a cool adhesive as it was smoothed on. Then a pump started, causing some of my flesh to be sucked into the object. The shampoo on my hair smelled good, lathered up twice and then rinsed. Then again with a different smelling product. Well, that pretty much fuddled my mind, too many things being done at once, my whole system shut down.

I awoke later, a cool washcloth laid over my eyes, the feeling quite soothing. As I came aware of what is happening, the pump is still doing its thing and there seems to be nobody between my legs as I felt nothing down there. My legs are still anchored to the stirrups, so it is not possible to close my knees, even though my body was wanting to perform that action. My head is wrapped in something, I can’t tell what, and the feeling of something happening is now coming from my hands.

I can’t move them even my fingers seem to be not movable. I concentrate and then feel something being applied to each finger. This continues until each finger is covered. Than a sudden thought became clear in my mind, the chair I am in is like a gynecologist chair used for a female pelvic examination and my feet are in stirrups. How did this happen to me, did I actually agree to all of this? I wonder what they are doing to me, maybe I won’t have to worry about Rebecca getting her revenge, I may have unwittingly done it for her. I took some deep breaths, I did ask for the full experience, and that is apparently what I am getting. My mind quickly scanning the documents that I had signed earlier to see if this is part of the deal. No conclusion there, for one thing I don’t remember what was said on those documents. I was just wanting to get this over with and as soon as possible. From what I can see and feel it is over with, my masculinity is shot.

The treatments continued, my ears are now pierced, twice in each ear. Other than the sharp pinch, I felt nothing until an earring is inserted in the holes. Apparently the bottom hole held a dangly earring, the end of it brushing against my neck. They came back to work on my hair again, now a foul smelling liquid applied to my hair, roots first, then covered with a plastic bag. The treatment lasted for about a half hour, since they are no clocks and the cool cloth over my eyes, it is strictly a guess on my part.

The bag is removed from my hair and then rinsed again. The upper part of the chair is raised some, leaving me almost sitting up. My hair is set in curlers, it seemed to be hundreds of them, but I am sure there were not that many. Then a dryer is wheeled over and placed over my head, the warm air feeling good for once. I could see some now, the cloth had slipped down my face, leaving one eye open. The cups on my chest are about half full, breasts are now a part of my life apparently. I didn’t even think of how or if they could be removed since they are being sucked from my body. I did get a glance when Jessica moved out of the way, to sneak a peek at my groin, now only seeing a female sex there instead. Some few quick breaths, holding that last one till things calm down some.

My eyes now focused on my nails, they now had extensions on each finger sticking out at least a half inch past my fingertips. The bright burgundy red polish making them that much more visible. There was no mirror to see what had been done with my hair, but I had a feeling that it was no longer the light brown it once was. Jessica worked on my eyebrows; I was sure she had jerked them all out earlier, but apparently there were still a few left, too many apparently in her opinion.

I tried to prepare myself for the unveiling, I am sure from the way that I feel, that the change will be drastic. To have all traces of your masculinity removed, it would be a shock to anyone. I sure hope that this is not all in vain, maybe Rebecca can see that I am trying hard, and cut me a little slack. Then if I have done all of this already, there probably is not any slack left to cut.

They did my makeup as the new breast tissue stabilized. The hoses had been removed from the machine, the cups however were still attached to my chest filled with my skin and tissue. There will not be anybody mistaking me for a male after this, the new protrusions from my chest quite significant. After an hour of conversation with Jessica as she did my makeup, she informed me that the cups would dissolve themselves in two to three days, even now I would find them to be more flexible and jiggly.

The mirror that I was able to see my image in gave me quite a surprise. Now a light blond and immaculate makeup, with a thin high arch in my eyebrows, earrings now dangling at my sides. Jessica checked the dryness of my hair, then started removing the curlers. Once they were removed she brushed the style up, pinning the majority of my hair on top of my head. Since I had a larger than normal head, she assured me that this hairstyle would be perfect for me. It would look quite feminine and make my head appear smaller than it was.

I wondered if I would be able to duplicate it, the changes guarantying me more than a few weeks in this new look. She pinned the larger curls in place, then put hairspray on the smaller tendrils of hair peeking out from the head of curls. The hairstyle only added to the female look, no one is going to see a male when looking at me. I did manage to get a picture of me to Ginger, the reply from her just said no way.

I was offered a chance to stay the night, but I felt it better to return to the office and face the music, then return tomorrow to get training in acting the female part. The salon had bettered the eight o’clock estimated finish time as I was in my car a little after four-thirty. I am sure Jessica was motivated since there was absolutely no masculine features left on my body. The outfit I was given to wear home assured the feminine look, an ivory suit with a pencil skirt, very business professional and according to Jessica also very cute. I drove back to the office, walking right in and to my private office. I know there were several onlookers, but I decided it better to get to my office then send out an email explaining my changes and the reasons for it.

My secretary, Ginger, was first to notice and first to invade my office to see the changes. Her face lit up with a big smile giving everything away. She had added the clauses to the contract, so had an idea about what was to come. “Would you prefer Ms. or Miss? I think Donna would be appropriate, but all of this is up to you. When I first got the picture I thought you were trying to pull a fast one, but seeing you in person you are truly beautiful. You look good, maybe even better than you were as a male. I can’t wait until our first conference call!” I was given a hug, a warm and tender greeting that was held longer than usual, as I pulled away I saw a tear in Ginger’s eye, hard to see clearly since my right eye had also teared up.

“I am drafting an email now about the changes, as soon as I have it done you need to send it to all the offices. Also a copy to Rebecca. In fact, with any management decisions or discussions in the future, a copy needs to be forwarded to her. This is to make her aware of all that we are doing.” I worked on the email, the correct wording took a while, but eventually I achieved what I wanted. The email stated.

Effective today Don Rasmussen as CEO ceases to exist. Donna Rasmussen has assumed leadership of the company, and I trust you will support her as you have Don. The decision to present as female is mine, one that has taken years to embrace. The company now has a new influx of money, so worries about our future should ease. Since the economy has shown a lot of instability, I have invoked a lot of cost cutting measures to insure that we keep an edge over our competition. Any discussion regarding the company or my presentation can be addressed to me by phone, email or in person. I will answer all in a timely manner. Thank you in advance for your support.

Sincerely, Donna Rasmussen CEO of D&R Realty.

P.S. Just a reminder, there will be a video conference call three days from now at ten AM. All associates of this company will be required to participate. No excuses allowed.

As I handed the email to Ginger, I asked her to change our stationery to read Donna Rebecca Realty instead of D&R Realty. When the time comes we can have the signs changed to reflect the new name. By then maybe the economic conditions might be a little more favorable. The email went out that afternoon late, I doubted I would hear anything until the morning. I said goodnight to Ginger and went home.

A few minutes after arriving I received a call from Rebecca. She had received my email, wanting to know if we might have dinner together tonight. “You just want to see what I look like, so let’s get it over with. Italiana Ristorante at eight, if that is alright?” She giggled, “That will be fine.”

I didn’t have any other clothes yet, so I went as dressed. I did repair my lipstick, as the salon had provided me with one to do repairs. I emptied my wallet into the makeup bag, and headed to the restaurant. Rebecca was waiting by the door and I walked right past her. I turned around and asked “Was she just going to just stand there and stare, or are we going to eat dinner tonight?”

She followed me and the hostess to a table on the patio, the weather nice, the patio was perfect for our dinner. Nothing was said for a while as she checked me out. Believe me there wasn’t much she missed, from my hair to my toes a careful inspection of all things feminine. I could see the smile hidden in her face, she was doing everything she could to suppress it. I asked her what she wanted to drink, then signaled the waitress to come over. Our orders were taken, the drinks came soon after and then we were left in peace as they prepared our food. Nothing here was premade, everything from scratch, so waiting for forty minutes to be served is not unheard of.

“You have surprised me, moving up the appointment, coming clean with your company, showing up as a female the first day” she stated. “I think I might have under estimated you a little.” I smiled, it seems my plan is working some already.

“I still have a long way to go, my wardrobe consists of only what I am wearing so some shopping is a necessity. Maybe tomorrow, after my female training and if all goes well, I can get started on my new wardrobe. On a side note, I am sure I will have a reaction to my email, not everyone will be happy with my decision. That will help in my cost cutting decisions, maybe a little shakeup will be good for everybody.” I told her that she would receive copies of all email with regards to any business decision. Also I asked that she include herself in any video conference call we had.”

She tried to decline all the inclusions, but I insisted. “For you to get satisfaction you have to see the interaction between me and my employees.”

She smiled. “I have definitely under estimated you, this ought to be interesting.” We chit chatted after finishing the dinner, but nothing more was said about my appearance. I hugged her and told her I would see her at the next video conference in three days. We departed and I made my way home.

Life as a female at home is not what I expected. Getting out of all the clothes is one thing, but slipping into the nightie that was furnished is another level of pleasure entirely. It took me forever to get my makeup cleaned off, the nightie sliding over my body as I moved my arms kept me in perpetual turmoil. Trying to sleep with boobs is another feat, finally I lay exasperated flat on my back as any other position pinched or squashed my new attractions. I did finally fall asleep, not a restful sleep, but sleep none the less.

I went back to the salon the next day, where I was put through my paces. Tall heels, up and down stairs, and at least thirty trips around the salon to get used to walking the way a woman does. Shorter steps, one foot in front of the other, and heel first were stressed to me. The gal that was overseeing my learning to do a female walk was serious, constantly on me about doing it the way she showed me and not my interpretation of what she said. It did take me the thirty trips to finally get it right though, well let’s just say better than previous attempts and apparently good enough for my drill sergeant’s approval.

We moved to makeup next, they would show me how to put it on, then have me clean it off and do it myself. This went on for several hours, each time I improved, in fact I thought I was doing quite well at applying the makeup. Next was some lessons in deportment, how to sit, what to do with my legs and feet, where to hold my hands, all the things that a female learns over time, that I had a morning to learn.

She spent some time showing me how to reproduce my hairstyle, suggesting twice a week appointments to keep the foundation there so that I could just brush it and apply a little hairspray to coax it back into the style.

My voice is next, if I kept it a little higher than a whisper it didn’t cause any alarms. That wouldn’t do in the long run, so Jessica sprayed my throat with a spray that tightened my vocal cords causing a little higher voice. That turned out to be the better option, I sounded female, and could talk in normal volume. The spray was good for several months, continued use of it would keep the vocal chords tight and eventually no more applications of the spray would be necessary. Not sure about the future with my voice, I liked the new feminine voice, but kept remembering that I was a male underneath all of this and that voice will not be appropriate for a male.

The last three hours of the day was spent in their clothing boutique, learning what went together, what my colors were and picking a basic wardrobe for me in the coming weeks. I chose to stay with dresses and skirts, thinking that would please Rebecca the most. I also found that the dresses in particular were the most comfortable to me, hence that is what I mainly chose to wear. Heading home that night my back seat of the car was laden with bags. I had my new wardrobe, most of it business professional.

Lingerie was included, after trying on some things I opted for a corset, its firm grip on my body comforting to me. Nothing extreme, the corset I chose taking three inches off my waist. The bras were lacy, and underwired, I liked the look they provided, but knew I would be ready to shed them once I got home from a day at work. For panties I chose a myriad of styles and colors, their hugging my new figure and my obvious flat front a noticeable difference from before.

It is surprising that very little thought of my missing male appendage appeared in my mind. I really didn’t miss it, it was never a favorite before, I never masturbated much, and dating was a joke, my business occupying most of my time and thoughts.

It took me several hours to put everything away, while taking all of my male clothes and packing them up. My closet was almost full, although I knew I still had to get some evening wear, for parties and social functions. Later that night lying in bed, I decided to give them to a charity that decision seemed to support my feeling that my transformation would be around for quite some time. I should be anxious to return to the male self, but I had a feeling deep down inside that would not be happening for quite some time, if ever. I was not sure that Rebecca would ever be convinced that the humiliation was enough, but I presume I could get used to living this way. My hope was that Rebecca and I would not continue to be hostile towards each other, maybe even friends at some point. It was quite a wish, but you never know these days what wishes might get granted.

I never did get the negative reaction I was expecting from my staff and employees, even the first video conference as a female was tame. I had made an announcement in front of all the associates about my reason for changing genders. I also stressed that the company would be run tighter now, things not totally necessary eliminated. I mentioned about the new properties we would be helping manage and the need to find similar properties at reasonable prices for expansion.

After the video conference, I received emails from every branch complimenting me on my appearance and offering me their undivided support in anything I might want to pursue. The next few days were unusual, dressing as a female every day takes a little getting used to. I remembered that I had promised to get active in woman’s organizations, so I asked Ginger to gather meeting times and membership requirements.

Two days later I had my first luncheon of a women’s civic organization. I was greeted warmly by their current president and sat at their table. I didn’t want any trouble later so I was blunt about my current sex, my reason for the change, and my genuine interest in their organization and their goals. They had no idea about me, surprised to say the least. They did listen, asked a few questions of me and then voted me as a member. Joyce their president told me of several more groups that I should join. If I wanted, she would contact them on my behalf. I agreed.

When the meeting was over Joyce approached me wanting to talk some more. “Why did you confess your real sex, you look so convincing no one would question you? I respect you for your actions, but wouldn’t it be less humiliating if no one knew your real sex?”

My heart felt response was “Probably less humiliating, but also not the truth. I want to deceive no one, but treasure my time as a female. I am glad you have seen fit to allow me to participate in your organization, maybe I can help in some special ways.”

“Just be aware that with more people knowing about you, that one of them might decide to share your secret with the rest of the world. I will try and make sure it doesn’t happen with my group, but I can’t guarantee anything.”

I looked her in the eyes and said, “If it happens it won’t be the end of the world, I will face up to it and move on. Make sure any referrals you make with me in mind that they know up front my true sex. I won’t have that being withheld from anyone. I do thank you for your kindness and understanding, it is greatly appreciated. I look forward to our time together, helping to advance feminine issues and ideas.”

Work at the office was just as it was before. I did notice that my appearance was looked at every day, there was some talk among the ladies, but later Ginger told me they were just complimenting me on my style, wondering where I learned about the things that I was doing now every day. The relationship between Ginger and me, however, only got better. She second guessed me on most matters, when I would tell her something I wanted done, I found out she had already started on it or was able to hand me the finished reports or email.

The financial reports of the company improved quite a bit every week. My cutbacks had helped considerably, and the new business that Rebecca brought to us helped our bottom line. We found several properties that she liked, so they were purchased and added to our management portfolio.

I visited three more women’s organizations, attended their meetings, and was warmly welcomed to their groups. All three I joined, after making sure they knew all about me. I was appointed to a couple of committees for these groups, and helped all I could. In all the participation in the women’s organizations, Rebecca was kept abreast of all my meetings and involvement.

Joining the organizations also turned out good for business, more customers and leads for others. Quite often I would get a phone call from one of the ladies wanting some service or referring someone to me wanting to buy or sell some property.

About the third week into my transformation, Ginger notified me that a reporter for the local paper wanted to do a story on me and my company. She told me the reporter’s name, that she seemed fair and caring. The articles she wrote were seldom vicious, just a statement of facts and feelings. I was a little leery of this, now my transformation would be known to all, as soon as the article was published. The dressing and acting as a female was comfortable now, still not used to it, but not something that I feared or shied away from.

I did all my personal shopping as usual, almost all in dresses or skirts. So far I was not singled out or had inappropriate remarks made to me. I shopped twice a week for groceries, ate out once a week, and usually shopped for clothes during the week whenever a sale was announced. As a former male, dressing and living as a female and automatically indulging in the feminine past time of shopping was definitely not the usual fare. It was fun, experiences that I had never indulged in that were enjoyable to me now.

The interview would complete the humiliation of Don, the whole town would now be aware of my dressing and acting as a female. Rebecca should be pleased. Recently, she has been quiet, never responding to my numerous emails. I allowed Ginger to make an appointment for the interview, then told her I needed my appointment at the salon to be moved up a day or two. If I was going to do this I wanted to look my best. Her giggle conveyed amusement that I needed to look good for my interview.

She however suggested that it be held at the office, rather than any other venue, in case there was any problems. A few minutes later I found out that I had an appointment first thing in the morning at the salon, and the interview with the reporter shortly after lunch at one thirty. I had Ginger email Rebecca about the interview, telling her that her attendance is mandatory. I didn’t want her to hear about it from someone else, I wanted her to hear what is said first hand.

I had made an outline of what should be covered in the interview and sent it to the reporter. Doing that I hoped that it would eliminate some surprises in the interview, since she would know what I expected to be covered in the session. I asked Ginger if she could think of anything else that should be done. A big smile coming over her face as she thought for a minute, then mouthed dress shopping then she jumped up and attacked me. It was decided that I had to have just the right outfit, most likely a dress to make an impression and also for the picture that would be taken for the newspaper.

Ginger was caught up, so we made our excuses and went shopping. She suggested the salon’s boutique, since they carried a full line of business clothing for the professional woman. The short drive was made as we discussed the interview and what its effect would be on the company. Ginger was pretty sure that there would be no impact on the company, my image and reputation would be the only things affected. If I came off as a modern professional business woman just doing her job as a company CEO, my history should have very little bearing on my current status. It might be noted in the interview, but my appearance and what decisions I have made would be considered more pertinent. How right she was.

We looked at every dress they had in the boutique, finally settling on three to try on. Our first choice turned out to be the one we bought. I even got a thirty percent discount because I was a regular customer of the salon. It was a classic LBD in design, a scoop neckline, mid-thigh in length and a fitted skirt. The color was not the typical black, but a dark burgundy with some lace accents around the neckline and at the end of the three-quarter length sleeve. We found a pair of burgundy pumps with a five inch heel that looked good with the dress. They even had the black lace trim around the top part of the shoe making them a perfect match to the dress. Classy but still within the parameters of business professional.

I dropped Ginger off at the office, checked my email, and then headed home. There was an email from Rebecca, her only comment was am I sure about the interview? My one word reply, ‘yes’. She did indicate she would be there, so that part of the grand plan was in place. I hoped that any hostility between us would vanish after the interview tomorrow. I would be out to everyone, performing my job as a female, leaving nothing for Rebecca to add to my humiliation. Then I remembered her wish for me to date a male, just like a typical female would do. I set there trying to figure out who I could get to ask me out that wouldn’t cause even more problems.

I didn’t want to go the bar route, I am not interested in finding a mate, just a date to satisfy the contract clauses. I had discussed it with Ginger, she suggested my attorney, a friend for several years and unmarried. We could discuss the business, instead of kissing and groping. That last stated with a giggle. I called Bob, asked how he was doing, everything but what I originally made the call about. I think he figured there was something I wanted, so he told me to just spit it out.

“As I am sure you remember the clauses in the contract, I need a date with you as part of the clauses in the contract. I know this is unusual, but can you make an exception and take me out?” There was silence for several minutes, I figured he was thinking about it, so I let the silence reign. Finally he made a reply.

“I will go out with you on one condition, well actually several conditions. First, it is to be a real date, both dinner and dancing or a movie. Second, you will have to be dressed to the nines, I have an image to protect and I can’t be seen with just anyone. Third, I get a kiss at the end of the evening, no negotiating on this one. If you do all of this I will be glad to take you out, my treat. Tomorrow evening at eight P.M. be ready.” No asking if that time was okay with me, just be ready.

I listened to the dial tone, he actually hung up on me, then I smiled, he treated me just like a female, one of his dates. We had talked about his dating over the years, although it was a male discussing it with a male at the time. He was an eligible bachelor and he knew it. He had yet to find someone to his liking, so they were only one time happenings. He had always been confident in his dealings whether with the law or with a date. The difference was he was confident not arrogant like I was in college.

Waking up to my big day, in more ways than you know. I grabbed a snack of an orange, got dressed in my sweats and with my dress in a garment bag along with my lingerie I headed to the salon. Jessica was ready for me, today nothing new to be done, just check to make sure everything was feminine and I was at my prettiest. Of course, my legs needed a touch up to get rid on the little peach fuzz found thereon. Several hairs of my eyebrows had to be removed, plus the wash and set I received every time I came in.

A professional makeup job, although I was fast approaching that level myself when I get dressed each day. Let’s not forget a manicure, fresh polish to match the dress. Looking in the mirror, I didn’t see any problems so I picked up my purse and drove back to the office. I was early, but the reporter and her photographer were already there. He got the photographs he wanted and went back to their office. Stephanie and I sat and talked in the office about her career, while we were waiting for Rebecca. She had made her way up through the ranks, nothing given to her without her earning it.

Rebecca finally made it and we started the interview. Most of her questions were what I had submitted or re-worded versions of them. I answered truthfully, telling her that I have felt this way for years, now the time had come for me to make the first step. Steph asked if this in any way made me feel humiliated, a normal male for twenty plus years just up and deciding to be a female for the rest of her life.

I looked at Rebecca, then smiled telling Stephanie that fate deals us a hand sometimes; what we have done in the past comes back forcing oneself to try and rectify that past deed or situation. This is one of those times. I am proud to be a member of the female sex now, proud to live my remaining years as a female, and trying hard to rectify some errors of judgment made in the past. I may never be able to repair the damage done, but at least I have made the effort.” Luckily Steph did not pursue that line of questioning, the interview ended shortly thereafter.

We shook hands, hugged and said our goodbyes. Steph said she would email a copy of the article to me as soon as she is finished with it. She assured me I would like it. That said with quite a smile. Ginger had recorded the interview just to be on the safe side, in case what was said was questioned. She went back to her desk, leaving Rebecca and me in the office. Rebecca had set on the couch when she came in, so she patted the cushion next to her wanting me to come sit next to her.

As I set she took my hand, holding it between her hands. “That went well Donna, you handled it very professionally, a credit to your gender. You have proven to me that the Don I used to know no longer exists. I release you from all the provisions of the contract that I had forced on you. I would like to take you to dinner tonight if you will permit it. A thank you for how you have handled everything so far.”

With a giggle and a smile, I told her that, “Tomorrow might be better, for tonight I have a date, one that I had to almost beg for.” She gave me such a look, then broke out in laughter. “You mean you actually are going to date a man, who is this guy?”

“My lawyer, is the lucky male, the only one that I thought I could get to ask me out, but he had conditions and now I have to abide by them. I have to dress up fancy, go dancing with him after dinner and give him a kiss at the end of the evening.” Rebecca just hee-hawed, enough so that Ginger came back into the office to see what the commotion was all about.

Ginger watched for a minute then returned to her desk, after reminding me that I needed a dress for this evenings date. Rebecca asked if she could help, either with the dress or my date. She volunteered to call him, informing him of my preferences, just to make sure the date was enjoyable for me. To her surprise, I told her, “That would be fine, that way Bob will know what he is getting tonight from one that had dated me before.” Rebecca rose from the couch, hugged me and gave me a sensuous kiss. “You just wait till tomorrow night, there will be no question after our date who you will want to spend the rest of your life with.” Another quick peck and she was gone.

Now what did that mean, was she interested in me still? Maybe it is just the clothes, or the body, even if I am naked there would be no doubt about my gender. I thought Rebecca was straight, she always dated males in college, in fact as far as I know she didn’t even have a roommate during college. Ginger came in smiling, now you will need two dresses and another appointment at the salon for tomorrow. I asked her what she thought about Rebecca’s comment, but her only remark is wait until tomorrow and all will be clear.

Ginger had some work to do so she called the boutique and told them what I needed and they would have some things picked out for me to choose from. Besides she wanted to be there when the email came from Stephanie, about the interview. She promised to send me a copy when it arrived. I grabbed my purse, such a feminine thing to do, but I found it ingrained in me already. A lot of things that I have been doing these last few days have stuck with me, now I am doing them without even thinking about it. I regularly checked my lipstick, reapplying it as needed.

I drove over to the boutique, walked in and was immediately led back to the back. Two racks were waiting for me in one of their dressing rooms, loaded with possible choices. I picked one out and took a look at it and immediately put it back on the rack. I am sure there would be very little not visible while I was in that dress. It was lacy with a sheer matching panel, very provocative and way too sexy to wear on a date. Continuing to look through the rack I tried on several, I looked good in them but for some reason they just didn’t seem right.

On the second rack another sexy dress made its appearance. It did have solid material, not see through like the other dress, but its problem was it covered so little of my body. I bulged out the top of the dress, the pencil skirt of the dress barely covering my panties. The associate helping me suggested thong panties and a special bra that would lift and enhance my natural bust line. I almost broke out laughing at that comment, my natural bust line, sucked from my body and definitely not natural for a male. I tried on a couple more dresses, but those two kept coming back to haunt me. I asked the associate to get me the proper undergarments for both dresses and ring me up.

For tonight’s date I decided on the short one, sure to please Bob, maybe I can get some free legal work in the future for my date tonight. Business always comes first. I hope my look is satisfactory for his image, can’t have his image ruined by some normal looking female, even if she is a CEO.

I made my way home, the job the salon had done on me this morning left me very little to do other than redo my lipstick. I changed undergarments the bra lifting and separating my breasts, in the dress they looked like they were going to spill out at any moment. The panties that went with the outfit were very brief, the associate called them bikini panties. After getting the dress on, I tried three times to get it to cover more of my thigh, all three attempts failed miserably. I doubted my sanity when I thought that this dress was the proper choice for tonight. I knew it looked good on me, but the fact that I couldn’t set down in it without my panties showing made it very unpractical. I tried crossing my legs, it did help, but was very uncomfortable. Not that it pinched anything, there was nothing in the way, just a flat front with an inviting slit.

Bob was on time, I grabbed a shawl and my purse and we were on our way. He was very gracious, complimenting me on my looks, getting the car door for me, pulling out my chair at the restaurant and all the other things a proper gentleman does for his date. He had his arm on me the whole time, leading me to the table, to his car, then back to his car after the restaurant. He took me to the fanciest dance club in town, and we danced every dance for three hours. I did get a respite from time to time for a drink, but then back to the dancing. He was an excellent dancer, both in the faster dances and in the slow romantic ones. I gave in after the first slow dance and held him close with my head on his shoulder. His only comment was, “It is about time.”

All in all it was an incredible evening, fun and exciting. The whole time I was a female, both in body and mind, Don never appeared in any way. I think that evening I had decided to stay a female from now on, the feelings just too nice to ignore. I enjoyed my date with Bob, even the kiss was sensual and lasted far longer than I anticipated, but I doubt I will try and convince him to be my boyfriend.

After I had undressed and slipped into a nightie, I made myself a cup of hot chocolate, and went to my bedroom to try and put some things in perspective. I had a love seat over by the patio doors leading out to a balcony, so I set down and stared out at the night sky. There were no clouds tonight, the myriad of twinkling stars the only thing visible in the darker background.

Lots of thoughts ran through my mind that night, most of them should have never entered my mind. They were all about me being a female now, the pleasure I was getting dressed as one, my date with Bob and my utter acceptance of my modified female body as being right for me. I thought of the interview today and reached over to turn my phone back on. I had turned it off to preserve my sanity, it is enough just to be dating a male, much less dealing with any other matters.

I looked at the messages and sure enough a message from Ginger with the interview attached to it. I read it on my phone, too comfortable to get up and access it with my laptop. I read through it twice, it actually was quite complimentary, mentioning my desire to fulfill a lifelong wish, and the professional manner that I handled it with regards to the business and my employees. She covered all the points that I desired to be mentioned, dealing with each one in a concise manner. She even mentioned my partner Rebecca in the article, but not any comment or reaction from her.

I looked further down the list of messages, finding one only a few minutes ago from Rebecca. I read it three times, so surprised at its contents. She was pleased with the interview, hoped that I had a good time with Bob, and wanted to be sure I would be at the office early, she had found a perfect dress for me, hoping that I would wear it tomorrow for her. I replied that I would, and thanked her for her generosity. I wondered what she had in mind, she already knew I had a dress purchased for our date, another dress now was a little unusual.

I sat there for quite some time staring at the stars, even noticing a couple of shooting stars, I made a separate wish on each star. Finally the hot chocolate had done its thing with me yawning and now ready for bed. I slid under the covers, pulled the comforter up over my shoulders and quickly lost my battle to stay awake.

The next thing I remembered was my alarm going off the next morning, I felt too comfortable under the covers so I resisted until it had rang for the third time, an hour after I should have got up. Soon, thereafter, I received a call from Ginger wondering if I was coming in today. I told her I would be there soon, just don’t hold her breath. She giggled, but pointed out that I had missed Rebecca and I should come in fairly quickly to get a look at the dress that she had left for me. I tried to pry more info, but she said the only way to appreciate it was to be standing and looking at it.

I visualized lots of things over the next few minutes as I tried to find appropriate clothing and make myself presentable. From some designer original to some gaudy bright color monstrosity ran though my feeble mind. It took me more than an hour to get to the office, went directly in and noticed the dress hanging on the back of my closet door. I sat down hard in my chair, just mesmerized by what I was looking at. Ginger was right behind me, watching as my eyes were transfixed on the dress.

“Rebecca expects me to wear that dress on our dinner date; I doubt I will fit into it, but even if I did, to wear it in public is probably against the law!” I told Ginger. If none of the other things humiliated me, this dress will definitely finish me off. Ginger suggested that I remove my clothes and attempt to get into the dress, then go from there. When she removed the dress from the garment bag, she discovered a wicked looking corset, one that would support my breasts and end about mid-thigh. As she laid it on my desk she giggled, “I can’t wait to see you in this corset, and if I can get it cinched up, you are going to be so feminine. From the looks of the dress you will have to be in the corset for the dress to fit properly.”

We attempted the corset first, it required both sets of hands to get it around me and the busk fastened. The she started tightening the laces. Just fastened around me the corset took off inches, each subsequent tightening of the laces took another inch off my middle section. I noticed my breasts swelling up a little, not connecting the corset and the swelling of my breasts until a few minutes later. The tissue that was being squeezed was forced to either swell up my breasts or fatten my hips. Ginger stopped several times holding the dress up against me to judge whether she had to take more off. But the smile never came off her face, to her this was fun, something she didn’t get a chance to do often. About the fifth time she went up and down the laces she thought the dress might fit.

She had me step into it, then worked it up over my hips, that alone took twenty minutes to accomplish. Believe me there was not even a quarter inch of space between my skin and the dress. Then came getting the top part of the dress up over my boobs. Another fifteen minutes and she was able to button the back part of the dress closed. Instead of a zipper, they had added a multitude of tiny buttons, each one barely fitting through the button hole.

When Ginger had fastened the last one she smiled and scooted the free standing mirror over in front of me. It had been purchased so that the new female in the office could see if her presentation was adequate before venturing out. I tried to move a little to see the side and rear of the dress, but found my movements very restricted. Ginger saw what I was doing, but suggested that fewer movements was better, because if I attempted too much movement, I would likely be exposing myself quite a bit.

My bulging breasts were barely contained in the top, the nipples just barely below the edge of the bodice. The dress looked like it had been sprayed on me, not a wrinkle or fold visible anywhere you look. I tried to move forward, but a two inch forward movement was all that I could manage. My arms still had mobility, but hardly anything else. The image in the mirror was pure erotic, a gorgeous female poured into her dress. Rebecca has to be nuts, I can hardly move how am I going to be able to go on a date with her?

I asked Ginger to get her on the phone for me, I desperately needed to talk to her about this. I tried to sit, that was impossible, then I tried to maneuver around the office some, I made a foot before Ginger told me to pick up line two. I had to lean back towards my desk to pick up the phone and was appalled as one of my breasts fell out of the cup of the corset. When Ginger came back into the office to see why I hadn’t answered the phone she burst into laughter. Meanwhile, I was trying to talk to Rebecca. I could tell Rebecca was smirking, she had to be knowing what I was calling her about. She asked if I was in the dress yet. Sarcastically, I told her “yes I am in it.”

“Donna you must calm down, I am sure you look fantastic in the dress, I will pick you up at the office at six” she said. Then the bitch hung up on me. I was mad until I realized the situation I found myself in. I started to giggle, I could try to laugh but I doubted I could get enough of a breath to do so.

Eleven in the morning, I would be trapped in the dress for hours before she picked me up. I took too long to get into the dress, I was not going to go through it again for the date. Then Ginger walked in with the shoes that went with the dress. I let out a quite audible sigh, they were very tall with only a strap above the toes and a very thin strap around the ankle. My toes and three quarters of my foot will be on display, my ankles arched severally up because of the five inch plus heel height.

It was mid afternoon before I was able to sit in my desk chair. Either the dress was stretching or my body was adapting to the corset. As I sat I felt it would split wide open revealing me in my sexy corset. All I managed that day was a few phone calls, my predicament excluding any other activities. It seemed that the time was dragging along at a snail’s pace. I swear the seven hours until she picked me up was more like fifteen! Right before Ginger left for the day, she had me try walking in the dress. I was able to manage a fast shuffle, gaining about six inches with each step. It was very fortunate that I had not eaten or drank much liquid, as it would be impossible to be able to use the ladies room without spending hours doing so. I took me five minutes to get to the bathroom so I could replenish my lipstick.

Rebecca finally made it at ten after six with her chauffeur alongside her. I was kissed and hugged then she pulled back to appraise the dress. She reached over to the desk to retrieve my purse and then Stefan came over and picked me up slung me over his shoulder to take me to the limo. I protested for a minute but then realized it was by far the better way to get down eight floors and through a hundred feet of lobby. Set back down on my feet outside the limo, I slid in and Rebecca joined me. All the time I was trying to get my boobs back inside the dress. When I was lifted onto his shoulder both breasts slid out of the cups dangling between me and his shoulder. I was bright red, a most embarrassing situation for a female much less a former male.

She was dressed in a very feminine pant suit, in two shades of brown. Her hair was in a braid, and she wore minimal makeup. Apparently I was the female tonight, her pantsuit the only feminine thing she wore. No jewelry either, I had only the studs in my ears so far. I said so far, because there was a jewelry box on the back of the next seat. When we reached the restaurant, Stefan parked around the corner and Rebecca opened the box and removed the contents. She removed my studs, inserting the two chandelier earrings in their place, I presume they were real diamonds by the brilliance and the name on the jewelry box. That name, the premiere jewelry store in the state, most of their pieces sold in the neighborhood of ten thousand dollars. Quite often they advertised that if you had to ask the price this was not where you needed to shop.

I felt them sway against my neck and then the sight of the necklace took my breath away. It had multi strands of smaller diamonds along a gold chain that was exquisite. The detail was precise and miniature, the combined look of the chains made the necklace look fabulous. She attached it around my neck with a click, then added one more thing to my jewelry for the night. A gorgeous engagement ring was slid on my finger, perfectly sized and absolutely brilliant. The one large stone, quite sparkly, the surrounding smaller stones situated to make the larger stone stand out.

I started to protest, but her finger on my lips stopped that. “Wear them tonight, enjoy the evening and when we get back to my place later we will talk.” Suddenly, I realized how deep I was into this, Rebecca still cared for me, from what she has done tonight, that attraction appeared to be quite strong. The jewelry alone an indication of her affection for me. An engagement ring no less, jewelry that is real and quite expensive were those not just given to friends or business partners.

I had misjudged her and thought my treatment of her in college had ruined any chance of a romantic relationship. Instead my recent actions has seemed to make her forget those acts of humiliation that I had made her suffer through. I am sure she is still having fun with me, this dress a prime example. The jewelry though shows something else at work here.

The driver pulled up to the restaurant since I was now bejeweled appropriately. OMG was the only letters that emerged from my mouth. The fanciest restaurant in town, reservations taken months in advance just to sit at the lower levels of the establishment. The driver came around to the door, opened it for me and helped me out. I kept a wary eye on him, fearful that I would be toted off again. He did the same with Rebecca when she took my arm and led me to the front doors.

My steps were slow, the dress just not letting any kind of normal movement to occur. The Maitre’D recognized her and we were led off to an elevator and then up to the third floor balcony. Our chairs were held for us and before we got situated in them wine was being served. I took it that Rebecca had ordered everything in advance since we were never asked our preferences. The food was excellent, cooked to perfection and seasoned perfectly. There was a band on the lower level, playing during our dinner. Rebecca asked me to dance when a slow number was being played, probably the only thing I could dance to in this dress.

I was pulled tightly in an embrace, her arms around me and my head laying on her shoulder. For some unknown reason six straight slow numbers were played in a row; she never allowed me out of her embrace. Actually, I was quite comfortable there not wanting to be any place else. We stayed for three hours, taking about trivial things, the weather, the food, the band, anything but what we were feeling. We danced several more times that evening, a most enjoyable occurrence.

Finally it was time to go, we made it back to the limo and then back to her home. It was a gorgeous house, several years old and quite beautiful. It was not ostentatious, just a typical upper crust family home. The grounds were well manicured, making the house fit in well into the suburban neighborhood.

The driver got our doors after parking in the drive, just outside of the garage. Me first, then Rebecca, I had relaxed my guard some, so when I found myself being put on his shoulder for the trip to the front door it was another surprise. Of course, I was not sure if I was more embarrassed by his action or my red face and shoulders. He carried me all the way into the living room where he set me down on my feet, and tipped his hat to me. I am not sure what the proper protocol is but I thanked him anyway, still red faced and a little wobbly on my feet. First action was needing to get my erstwhile breasts back in the dress again.

Rebecca joined me giggling, her apparent enjoyment at my expense was quite satisfying to her. She made her way to the kitchen, returning a few minutes later with two glasses and a bottle of wine. She told me to sit on the couch and parked her behind right next to me, and I do mean right next to me. She poured me a glass of wine, then her one and we toasted. “To things that are important in life” she said to me as we looked into each other’s eyes.

I sipped my wine, wondering where all of this is going. I felt helpless in the dress tonight, but other than a few words I was not teased about it or humiliated because I was wearing it. We had a nice time tonight, I enjoy her company immensely, just wished that I hadn’t ruined things in the years past. She put her arm around my shoulder and pulled me closer till my head was on her shoulder. She tilted her head down and I received my first kiss of the evening. It was not overly passionate, but it did convey her feelings for me.

We set there for at least an hour, sipping wine and nibbling on each other. “What are your plans for the future,” she asked? I was not sure how to answer, I had made some changes recently in my personal plans, but not sure how Rebecca might respond to them. From her actions tonight she has apparently forgave me some, but still what I had decided to do was maybe further than she might be comfortable with. I decided to tell her exactly what I intended to do, it either would be alright with her or any chance of a relationship would be lost.

My reply was, “I have decided to stay as a female if my business partner will allow it. The changes I have experienced have so enhanced my life that I no longer wish to live as a male. I enjoy the camaraderie between females, the clothes, even the makeup. If I still have a job, I would like to live out the rest of my life as a female.” She had set her wine glass down on the coffee table, then used both of her hands to move my face directly in front of her. She kissed me passionately, trying to meld her lips to mine leaving me breathless.

I never did hear a response to my question the kiss went on and on, with only a break to take on additional air. I was pulled closer to her our upper bodies pushed together squashing our breasts against each other, the heat from our bodies warming the air all around us. Her response to my question was in the form of another question. “Can I go with you to your home and help throw out all of your male clothes. Pretty please?” How can one turn down such a polite request?

We set there for quite some, her arms around me, with my head on her shoulder, there were no words spoken, just two people renewing a relationship. I presume that it was a relationship now, still I considered myself very lucky for her taking me back after all the horrid things I had done to her back in college. A couple of hours later, she dragged me to her bedroom, helped me out of the dress, let me use the bathroom then patted the edge of the bed where she is lying.

As I approached the bed she pointed to a negligee lying there, asking me to slip it on. It was floor length, long sleeve, and absolutely gorgeous. I slipped it over my head, my hands sliding down the sleeves, and the gown’s hem on the floor of the bedroom. It seemed way too big, but the smile on Rebecca’s face said she liked it. She pulled me down next to her, then cuddled up next to me, her arms around my body playing with my breasts.

I was still trying to find the end of the sleeve, to put my hands through it, but her lips on mine, curtailed that action for a moment. She then slid down my body to my ankles, playing with the hem of the negligee. I heard a zipping sound and raised my head to see what she was doing. She returned to my face kissed me again, then reached for my hands. She hooked the two sleeves together and slid her body between my arms so that I was holding her in my arms. She wiggled a little, then laid her head on my chest. I then discovered that my hands were trapped in the sleeves and my feet were trapped within the negligee.

Rebecca had the biggest smile on her face, little giggles threatening to breakout at any minute. “Now you have to love me, you are trapped in my negligee prison, never to be released until I am pleasured and pleasured well. I do love you, I always have? You tried to ruin things back in college, but I knew that you would come back to me. The events of the last few weeks have been fun, but all I was trying to do is get you to realize what is inside of you, the true Donna, so to speak.”

“I am proud of you, you have finally realized your place in life and owned up to it. I doubt I will let you go back to your home, unless there is something that you just have to bring back here. We can send someone to get rid of your male life, you belong next to me, as my lover, my BFF, my everything. Let’s find someone to take your place at work, you can still go in every once in a while, but I can think of a lot of things to keep you occupied right here at home.”

Except for going to the bathroom I was kept in the negligee for hours, usually in her embrace, a place that I never wanted to leave. It was comfortable, especially when her body was trapped between my arms. I did all I could to please her, but with me restrained there was not a lot I could do for her. I made sure she was kissed at every opportunity possible. When she slid out from between my trapped arms, I tried to maneuver my face where I could show appropriate attention to her breasts, the low moans I received in return made me feel good that I was making her feel loved.

She, however, was unhindered in her actions, making me twist and turn, to escape her tongue and mouth. Several times I just lay there, pooped from all the exertion, but so happy. Rebecca eventually wore herself down about four hours after we started. Soon both of us were sleeping a deep and restful sleep. Neither of us had set an alarm, so it was mid-morning before my phone woke us up. Rebecca answered, then held the phone against my ear so I could hear what the caller wanted. Ginger was giggling, knowing that the two of us were together answering some of her questions.

She wanted to know if I was coming in, or if I was preoccupied with an important business meeting. Then the laughing started, Rebecca taking the phone back from my ear. “Yes, it is an important business meeting, requiring both of us to be in attendance. You are quite capable, do what you think is right and after you get off work come by my house. Donna and I have something to discuss with you.”

Ginger started giggling again, then told Rebecca, “If you are offering what I think you are, then I will take it, but allow Donna to come in quite often. Otherwise, I will miss her too much.” Rebecca smiled, then reached over and squeezed my right nipple, causing me to squeal and then started giggling. “Since the negotiations seem to have begun again,” Ginger said, “have fun, and I will see you all later.”

I never did escape the negligee that day, when Ginger showed up later, I was still in it, and at the mercy of Rebecca. Ginger did check it over thoroughly, squeezing a nipple or two to see if the fabric was restricting movement. We explained to Ginger what we had in mind. For her take control attitude, she was perfect for the job. She had already made some plans, which she ran by us before she left. I did get a kiss before she left, but also asking Rebecca to send me to the office this way, then she could have some fun in the afternoon.

I pouted some, but was enjoying the love of Rebecca, especially when she fed me dinner one bite at a time. When it was time to head off to bed I was finally released from the negligee, I made a point to spend the rest of the evening and most of the night giving Rebecca as good as I had received. She tried times to get me to quit, but I feigned a lack of hearing and continued my assault. I gave out at one AM, to a big sigh from Rebecca, but she was awake only minutes thereafter before I heard her breathing slip into a sleepy pattern. I joined her shortly, loving and kissing is such hard work.

Ginger did take over, the business never suffered, her actions prevented any problems from occurring. I did go in every once in a while talking with the associates and Ginger. We got into the habit of a once a week lunch, but business was seldom discussed. Instead we talked about fashions, about men and about Rebecca. Ginger did capture a heart, Bob the attorney fell for her, and their upcoming wedding was an excuse for me to dress up and have some extra fun. I am to be a bridesmaid, along with Rebecca. Something I am so looking forward to.

We did get married, a quickie trip to Vegas, a wedding chapel marriage and then a honeymoon in Australia. Yes, the negligee was brought along, other than pottie breaks I spent three days locked in its embrace. My nipples were so sore after that, but Rebecca rubbed soothing lotion on then quite often. I also lost five pounds from the physical exertion and squirming. I was hand fed for those three days, a little wine and not much water. She liked me helpless and dependent on her.

I never did see much of the country, after the three days only an hour or two a day was spent on sightseeing. The rest was spent with me flat on my back. As we were flying back she wanted to know if I felt humiliated enough to make up for what I had done to her in college. I smiled, if she didn’t remember the other incident I was not going to remind her.

To keep busy I went into work, Ginger thrilled to see me. Of course, I had to tell her about the trip, her giggling since I spent the majority of it on my back being ravaged.

I got to see some of my friends at the office, all of them complimenting me on my rosy cheeks and huge smile. The gals all smirking knowing what was really going on, but they were happy for me and even a little envious. That night Rebecca took me out again to eat, at least this time she allowed me to walk into the restaurant, the dress she picked out for me having a generous skirt.

The meal was exquisite, something French, I have no idea what was in it, but it tasted so good. We stayed longer than we should have, talking about everything. The partnership between us was working well, Rebecca’s companies all exceeding their goals, especially the new branches that we had found for her. Our company was also doing well, record profits and several new branches in areas we had never explored before.

It was late when we returned home, nearly two AM. I was undressed, eased into bed and played with until the sun started to show itself over the eastern horizon. I was really out of it, we had finished off two bottles of wine after we got home, so I doubted I was aware of much of anything that morning.

It was mid-morning before I returned to the land of the living, laying in bed going over the past few weeks in my mind. I was more than paid back by Rebecca for my transgressions, as the saying goes, Paybacks can be a bitch. How true, but since Rebecca and I are back together both romantically and business wise, the payback was well worth it.

Story Complete For Now

© 2016 thru 2021 Fran Cesca Walker

Leave a Reply

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