Feminized To Save My Job And Life

I sat in the attorney's office as my late father's will was read. My multimillionaire father had left me, John, his ownership in the company that he had founded and built throughout his lifetime, the family house, and one million dollars. The balance went to several of the charities and universities that my father had supported and been a board member of for years.

As the attorney finished reading the will, I asked, "So I own the company now?"

I was shocked when the lawyer replied, "No, John, you own 45% of the company. Alicia Harrington owns 55%. Your father and I set up the company as a WBE, a Woman Business Enterprise, to gain an advantage on several major government contracts. Those contracts make up well over half the income of the company.

"So, Alicia is now the company CEO, and not me? I asked.

"As the major owner, in consultation with you as the minority owner, Alicia Harrington will select the next CEO. She would like to meet with you tomorrow at 10:00 AM in your father's former office to discuss your role in the future management of the company," the attorney explained.

I thanked the attorney and left his office. The will had turned out to be a disaster. After I paid off my gambling debts, and other outstanding debts I would be broke even if I got a good price for my condo after I moved into the family house. That my future was in Alicia's hands was especially bad news. She had a strong dislike for me, and I had given her a strong basis for the opinion.

Technically Alicia had been Dad's executive assistant. In practice she oversaw the financial, HR, and contract administration for the company, while Dad dealt with getting the contracts the company ran on and oversaw me and operations.

My role had been production manager, working with the mechanics and workforce that made and shipped the goods. I understood Alicia knew all about my asking for and accepting sexual favors from the largely female production workers for better job and shift assignments. In her role over HR she had dealt with more than one sexual harassment claim, and quietly settled them without ever telling my father. It didn't help that my dismissive feelings towards women had included my dealing with Alicia. I liked to call her "Honey" "Missy" or "Sugar" just to watch her ears turn red.

It was with great trepidation that I approached the corner office that I knew so well. I was surprised to see Alicia's daughter working away in Alicia's office as I passed it. She was drop dead gorgeous; tall, natural blonde, stacked, and obviously worked out. She hadn't worked for the firm, so I wasn't quite sure why she was working in her mother's office.

The door to my father's office was open, so I stepped in and immediately stopped. Alicia was sitting at my father's desk with several papers laid out on the desk. She motioned for me to sit in the plain unpadded old oak armchair placed in front of the desk.

I sat and Alicia just sat there looking at me. I felt I should say something but had no idea what to say.

Alicia finally started explaining, "John, I know you have paid no attention to the financial side of this company for the twenty five years you have worked here. Historically the company has paid no stockholder dividends. Profits were distributed to employees and management, including your father and myself. My point is that there is no income from the 45% of the company that you know own. The only income you have received and might receive has been as a company employee."

While it was news, all I could do was nod my head that I understood.

Alicia stared at me for well over a minute, never breaking eye contact, then continued, "What I have on my desk are your termination papers for cause. As a WBE someone with your attitude towards women is a problem, your documented history of sexual abuse in intolerable."

I swallowed hard and blurted out, "But this is my father's company, part of it is now mine."

Alicia again stared at me, "The key is that your father was a minority owner of this company, which the majority owner, me, felt that his role as CEO was critical to the continued success of the company. I obviously do not have that opinion of you."

I was stunned, but finally spoke, "So you are telling me that I am now terminated for cause, which means I'm not eligible for unemployment, and I will receive no compensation for my part ownership of this company?

Alicia nodded, "That is correct. You should have been terminated years ago, but your father would not allow it. He paid the harassment settlement money out of his own pocket."

I was shocked, I was speechless to learn that my father had covered my inappropriate behavior and never said a word.

Alicia stared at me for almost five minutes as I sat there before finally speaking. "I do have another option, a last chance agreement. If you agree, you will retain your present position and salary, in return you will undergo "female orientation and appreciation" up to and including feminization. If at any time you refuse or fail to show proper respect to any company employee you will be immediately terminated for cause, and at least three employees will file a civil suit against you. Our attorney has drafted the agreement, you may take it with you and give me an answer by 5:00 today or I will sign the termination for cause paperwork, and the last chance offer is no longer valid. Changes to the last chance agreement are not possible or negotiable, it is a take it or leave it document. If you have any questions about what the "female orientation and appreciation will be like, you may talk to my daughter in my old office. She will oversee your last chance agreement and training, her word on compliance or failure is final. Do you want to consider the last chance agreement, or should I sign the termination papers now?"

I desperately needed time to think, maybe to talk to Dad's attorney. I finally stammered, "I will review the agreement and talk to your daughter and let you know by 5:00."

Alicia replied, "That is fine, Miss Harrington will see you at 1:30 to answer any questions you may have. Remember the offer expires at 5:00 as stated in the document. You are also to leave the premises now and go nowhere other than these offices when you return."

I caught the clue on the proper way to address her daughter when I met her. I stood to leave and extended my hand to shake, and Alicia ignored the courtesy. I turned and left, waiving at Miss Harrington as I passed that office.

I didn't know where to go or what to do. I called the attorney and was told he was not reachable today. He had served our family for forty years and wouldn't take my call. I googled feminization:

Feminization: 1) To give a feminine appearance or character to. 2) To cause (a male) to assume feminine characteristics.

I wasn't sure what that really meant, but it did not sound promising. Of course, neither did unemployment nor owing big money to some shady characters. The threat was that if I accepted the offer and then couldn't comply not only was I unemployed but facing harassment lawsuits.

I had a cheeseburger and only one small beer. I was certain that I needed to think clearly when I met Miss Harrington. Since when did a man call a younger woman "Miss". I took it as a warning sign.

I tried reading the legal agreement. From what I understood I was now required to treat every employee with respect and dignity. Misogyny in any form was grounds for immediate termination for cause. I had to look up "misogyny"

dislike of, contempt for, or ingrained prejudice against women

. It also stipulated that I would agree to education, subjugation and obedience training by women. I didn't like the sound of that last part, especially when it went on to say that I would immediately obey any command or wish of Mrs. or Miss Harrington or their designee under threat of immediate termination for cause.

I headed back to the office to make sure I would not be late. As I got into my car, I got a phone call from an enforcer called Bermuda, because if you go into his triangle you aren't seen again. I tried to explain that I would have most of the money when the transfer from Dad's account cleared. He didn't sound convinced, and his final words were both terrifying and horribly realistic.

I got to Miss Harrington's office five minutes early. I knocked and she did not look up or otherwise acknowledge me. I wasn't sure what to do so I waited at the door. A clock in her office chimed the hour and without looking up she said, "Sit down and be quiet."

She finally looked up at me and asked, "Did you read the agreement, and if so, do you have any questions?"

"Yes Miss Harrington, what is expected of me and what will be done to me?" I asked quietly.

Miss Harrington looked me dead in the eyes and replied, "You are expected to treat everyone with courtesy and respect, and to interact with them in an appropriate manner. To do that with this largely female group that you seem to feel beneath you, first you will be made to feel the way that they do. I will use clothing, humiliation, objectification, and sex, to help you see what they see and feel so that you can work with them appropriately. You will learn what it is like to be forced to use sex for what you think should be yours. You will learn that top down management is no longer the way that business is done in this day and age."

I thought a moment and said, "That doesn't seem too bad Miss Harrington."

She smirked and replied, "I frankly do not understand why you are being given this chance, but if you succeed you will be fundamentally changed, in attitude, demeanor, speech, and modesty. I will tear you down and hopefully transform. Do not underestimate the pain, humiliation, and abuse you will receive to reach that goal, if you are able to reach it, of which I have my doubts. Understand that if you accept the agreement, you are betting your entire future on being able to change who you are and have been for most of your adult life. Do not underestimate that challenge. For the first time in your life, since your mother, females are going to tell you what to do and your only choice is to reply "Yes, Ma'am" and comply fully to the best of your ability."

I asked, "When would this start, and how long will it take, and is this just during business hours?"

Miss Harrington shook her head looking disappointing, "It starts as soon as you sign the agreement. It will take however long it takes to transform you, or you quit. Your transformation is to be evident to everyone 24/7 - 365 for the rest of your life."

One more question, "If I sign, who do I give the agreement to?

She replied, "You will give it to me, and we will begin your education immediately. If you choose not to sign it, I would appreciate receiving your keys and ID badge. One way or another a decision will be made at or before 5:00 today. If no more questions, you may leave, please leave the premises directly and do not go anywhere in the plant except this office."

With that she turned and resumed working on whatever she had been doing when I arrived. I stood and left. My mind was made up when I got to my car and found the note from Bermuda on my windshield asking for payment or again describing the "or else," the cash from Dad's will would keep them off my back for a while, but I needed a good steady paycheck to not disappear into Bermuda's hole. It was now 2:30 and I had only about two hours to delay the start of my training.

I showed up at Miss Harrington's office at 4:30, signed agreement in hand. I stood in her doorway until without looking up she said, "Put the agreement on the desk and strip. When completely naked stand facing the wall, feet shoulder width apart, hands behind your head, fingers interlocked."

Without thinking I replied, "What?"

She immediately replied, "It is way too early in your program to fail. When told to do something by a female the correct answer is "Yes, Ma'am, and immediately comply. Do not ever make me repeat myself."

I started to disrobe: shoes, socks, shirt, pants, undershirt. I hesitated before removing my boxers, and hoped she didn't notice, before removing them and assuming the demanded position. Though that whole stripping, she hadn't looked over at me once.

I stood there naked for what seemed to be a long time. I heard someone come into the room and started to turn my head to see who and immediately heard a stern, "Face the wall, idiot."

I finally heard Alicia's voice say, "I'll take the measurements, you record them."

I sensed Alicia close behind me just before she wrapped a tape measure around my neck, She announced, "seventeen," then my chest, "forty four" my waist "thirty eight, my hips/butt forty-two, inseam thirty. The tape was then wrapped around my cock behind my balls, "ten," around my flaccid cock "four and a half," the length of my flaccid cock four".

Miss Harrington finally spoke, "A package will be delivered to your place tonight. Bring it in but do not open it. At 6:30 be kneeling naked facing away from the door, ass high, chest on the floor, knees as far apart as you can get them, nose touching the floor, eyes looking straight down. You will already have all hair removed on your body except what is on top of your head, and I do mean all, including stubble. Leave your door unlocked. I will be there to start your transformation. Remember that the only acceptable response to a woman telling you to do something is "Yes Ma'am. What did you say, I didn't hear you."

It took me a moment to realize what she wanted., "Yes, Ma'am" I replied.

Miss Harrington almost screamed, "That is all idiot, pick up your clothes and get out of my office."

"Yes, Ma'am"

I hurriedly picked up all my clothes and shoes, trying not to make eye with either woman. I ran down the hall naked, to the sound of laughter behind me. What had I gotten myself into.

I had never shaved below the neck before. I did an hour's research online and decided that the best was a fresh razorblade and old fashioned shaving cream. There were YouTube videos on how to shave your cock and balls. I made a quick trip out to get fast food dinner, new razorblades and some lotion. I then spent a quiet evening sitting in my bathtub shaving my entire body. Studying myself in the mirror I found a few strays on my ass. Not the easiest place to reach. Once satisfied I used the lotion as shown on YouTube to reduce shaving rash.

As I was rubbing the lotion into my skin the absurdity that I was to be "feminized" in order to keep my job and keep Bermuda from removing various body parts as debt payment. How did they expect to get the product made and out the door without me keeping them on task? Production fell 22% the month I was out sick.

I was just about to head for bed when the doorbell rang. It was a delivery person dropping off a medium sized box. As directed, I brought it into the house, but did not open it. I was curious, I was reasonably certain that it was part of my new life.

I finally went to bed. Still wondering what my new life was going to be like. I didn't like the idea of being feminized, whatever Alicia and her daughter had in mind. I decided to rub one out while I still could, imagining Miss Harrington on her knees kissing my balls and sucking my cock.

I was up at 5:00AM for a quick shower and stubble inspection and then breakfast. I was just putting the dishes in the dishwasher when I noticed it was almost 6:30. I quickly unlocked the door and got in the requested position, ass high, chest on the floor, knees spread wide and nose touching the floor, eyes straight ahead. Then I waited. After awhile I realized she had said to be in this position at 6:30, not that she would be here then. About that time, I realized how thankful I was for the fairly soft carpeting, but even with that my knees were starting to hurt.

I heard her heals on the wood porch before I heard the doorknob turn and the hinges squeak. I knew Miss Harrington was behind me inspecting me. I felt the toe of her boot against my ass and then move down till it was pressing against the bottom of my balls. I didn't move or try to look, I just waited.

The boot left my balls, and I could see her go over and open the box on the table and pull several items out though I couldn't see what they were. I heard a package being opened and sensed her back behind me.

She finally spoke, "Part of your training will to be on the receiving end of sex. Your ass will be trained and stretched so that experience does not damage you. A plug will be placed in your ass every morning either by me or by you. That plug will only be removed at the plant to use the restroom and then promptly replaced.

I felt something cold and wet hit my puckered asshole, followed shortly by a finger slowly working its way into my ass. It wasn't too bad until the second finger joined the first, that kind of stung. The fingers were removed and something cold and hard was pressed against my ring and slowly inserted. It started to sting more than the second finger but then seemed to be sucked into my ass. I could feel a ring on the outside of my ass which I assumed was to keep it from disappearing up my ass. I could feel the weight of the plug inside my ass.

She told me, "Crawl over to the table and take a seat on the chair. The first time I will assist you with your new uniform."

As I rose to sit in the chair, I noticed a lot of pink on the table. Hopefully that wasn't my new work uniform. Sitting down on the plug in my ass was a new experience.

The first item she pulled out of the box looked like crotchless pantyhose. She took them, knelt and worked them up to my thighs, then told me to stand and pulled the top up to my waist. They were crotchless and left my ass bare too.

She looked at me and said, "I hope you were paying attention when I helped you put those on, starting tomorrow you will do it yourself every time you get dressed.

She held up a bright pink thong and said, "There are several pairs of these in the box. They are the only undergarment you are allowed to wear. Put them on."

I pulled them up and tried to adjust them. I just wasn't used to having something between my butt cheeks, not to mention up my ass.

The next item appeared to be a satiny undershirt. As she handed it to me, she told me, "This is a chemise, you will wear one daily as well."

The silky fabric felt kind of good on my now hairless chest and back.

The last thing she pulled out of the box was a new pink dress shirt. I put it on. It was a much softer fabric than the standard oxford dress shirt I normally wore and of course the color was new to me, though men's dress shirts have been available in light red for years.

She then pulled a pair of pink high heels out of the box, and I got very scared. She said, "these are for in the house for now. When you get back from work, strip, remove the plug and stay naked except for these heels. When you can't walk in heels you are to leave them on and crawl."

Next out of the box was a pair of icepacks. As she took them over and put them in the freezer she said, "Each evening when you go to bed put one in a small cooler. Day or night at the first sign of an erection place an icepack on your cock and balls until it goes away. If it turns out, you can't do that there is a cock cage in the box per your measurements. "

The last thing Miss Harrington pulled out of the box was an enema set. She told me, "Once you start getting used sexually, you will need to be clean. So, start using this every morning after you use the toilet. To encourage your taking a morning enema, when you use the toilet during the day, you are to hold the plug in your mouth until you relube and reinsert it. Speaking of toilet, you are no longer allowed to stand and pee, you are required to sit every time, everywhere. Failure to do so will result in you wearing the cockcage.