The rest of the weekend, I learned to walk about the house wearing three-inch heels. Saturday night, we went out for dinner and a movie. I wore my regular shoes. My male shoes felt so heavy compared to the heels. The only consolation was that my calves were not as sore.
Monday morning, I called Rodney, leaving him several messages during the day. I noticed that Peggy was looking at me from time to time and I became very conscious of her stares. Tuesday, I was absorbed in working on payrolls that needed to be done. Since it was the end of the quarter, I needed to run the computer program for 941 and 940 forms which took me through Wednesday. I tried calling Rodney again, leaving a message. By Friday I learned that Rodney had gone on vacation and would not be back for another week. Vacation? The bastard had left town knowing that I would be stopping by to get my money?
Where was this all going to lead? It crossed my mind, although I dismissed the thought quickly, that perhaps my “friend” Rodney was in cahoots with my wife. A crazy thought to be sure, but I was in a frightening situation and my mind was working overtime. I mean, it was possible, right? At idle moments, when I paused my work to sip some coffee or take a bite of my bagel, the paranoia resurfaced. Suppose it was true. What then? Whether true or not, clearly Rodney and my wife would deny it, so there was little point in asking either of them.
Several times during my work day, I found myself literally shaking my head, trying to clear this bizarre conspiracy theory from my mind. Still, what if? Rodney was certainly acting as if he felt no pressure to pay his debt to me. Imagining a conspiracy between him and my wife seemed extreme, but it was a possibility, wasn't it? What if it turned out to be true? What would I do then? What could I do?
That evening I came home and changed into the high heels as I had done all week. At dinner, Amy only smiled when I told her I was unsuccessful in getting a check this week. I decided to help her clean up the kitchen before we went to watch television for the evening. Again I pleaded my case, trying desperately to postpone wearing heels to work. As a substitute for wearing heels next week, I agreed to wear nightgowns to bed in place of my pajamas. Not much of an improvement, perhaps, but I was grasping at straws and I knew it.
Saturday morning, we were at the department store where I was embarrassed at having to select two nightgowns and try them on in front of my wife and a salesgirl. The ladies shopping in the sleepwear department all stopped, watching me going in and out of the dressing room, carrying several nighties at a time. Amy chose a long pink nightgown with a square neck which was hemmed in a wide row of lace. The gown had short puffy sleeves trimmed with a narrow band of lace. The hem of the gown had a wide row of matching lace. The second nightgown, a long full-skirted lavender creation, had a wide scoop neck. The four-inch shoulder straps were white lace with lavender ribbons intertwined throughout the sleeves and across the bodice of the gown.
By the time we had completed our purchase, my face was beet red. I could not leave fast enough. Of course, Any was enjoying herself, stopping in all the other departments, particularly the lingerie as she and I window-shopped. She would point out a pair of French-cut panties, holding them up in front of me, saying, “These are simply adorable.
Too bad that you can not wear these because of the loose fit. On second thought, you might wear these over your high-cut panties. “The matching camisole makes a beautiful set, don’t you agree, dear? Look how lovely this yellow ribbon bra and matching panties are. You don't have a yellow set, do you? We must keep these in mind next time you require new panties and bras.” We went through the same thing in the sportswear department and then in Misses dresses.
Amy told me that probably I would be wearing dresses and skirts along with my feminine blouses and slacks. Saturday night, I wore a nightgown for the first time to bed. I enjoyed the soft nylon as it caressed my hairless body. It seemed that Amy enjoyed my wearing this lavender gown as well. We had a sexual experience that was probably the best we had enjoyed since our honeymoon, twenty years earlier. Hmm, maybe there was a small upside to my situation. Monday morning, Peggy came into my office, saying me that she wanted to take her two-week vacation starting next week.
I told her that there would be no problem. In the meantime, I tried leaving a message for Rodney to call me. By Wednesday day, he had not returned my call. I needed to have him pay me a least fifty dollars and maintain payments each week. What I really wanted was to be paid in full for his loan so I could return to wearing my own clothes and not have to keep my body free of hair. I called my attorney and explained that I had made the loan to Rodney and his payment history.
Peter, the attorney I used from time to time for my business, asked if I had a promissory note and a lien on the Cadillac. When I informed him that the original loan was made through a friend who paid me each week by withholding the money from his check, I was told that it would be difficult to enforce. I could try to get a judgment. However, as Peter informed me, the cost to recover $1400 would be about $1000. Not much point to going down that road, obviously.
Peter told me that possibly the court would not enforce my claim to the debt due to lack of an agreement. It would be Rodney's word against mine. I would be wearing dresses to work until I collected, I thought glumly. Knowing Rodney would fight a court battle had me thinking carefully about resorting to legal action.
Friday night, I informed Amy that I had not been able to get a check from Rodney but was hoping to see him next week. Saturday morning, Amy assisted in putting the hair removal lotion on my body. After my shower, I patted myself dry, then she applied body moisturizing lotion to soften my skin. Amy seemed very pleased with the results. Was it normal for a wife to enjoy her husband wearing women's clothing and being hair-free?
Was there something about Amy that I hadn't known even after twenty years of marriage? Was my feminization something she had been planning all along? Had the Rodney situation given her an excuse to realize a long-suppressed fantasy? Monday morning, true to my word, I went to the office, wearing only feminine clothing. I was able to walk properly in the three-inch heels, having practiced for the past two weeks as my wife watched and instructed me how to walk, turn and stand in them.
Thank goodness Peggy was on vacation. I had packed a salad and a piece of fruit at the urging of Amy. Tuesday, Amy came to the office, having me take her to a small ladies' tea room for soup and salad. I am sure she was making sure I was in the proper wardrobe. It was shamefully embarrassing having the women at the tearoom watch me walk while wearing thin high-heeled shoes. At the end of the week, I tried calling Rodney at his shop. No one answered the phone.
Even though I was embarrassed about having Rodney or his workers see me wearing heels and back-zipper pants, I drove over to his shop. I needed to collect at least fifty dollars. The gate and door to his shop were locked. I noticed several cars in the bays but no one was around. I walked around to the back of the shop to check the door there, extremely aware of my every step in the heels. I could hear them click on the concrete and, while it was a bit of a turn-on, I was terrified that one of Rodney's men would suddenly appear and see me in them.
What lie could I tell to explain my predicament? Had Rodney told all of his co-workers about my situation? Fortunately, no one was around the shop building, so I was able to make my way back to my car without incident. Once seated, I realized that my forehead was covered with sweat from my nervousness. Saturday morning after showering, I sat down at my wife’s vanity while dressed in panties with a matching pink bra, garter belt, hose, a pink camisole, and three-inch black heels while Amy showed me how to apply makeup to my face.
This included using a cleanser before moisturizing my face, liquid foundation, setting powder, eyeliner and shadow, mascara, eyebrow pencil, blush, and lipstick. After I put on the blouse and pants, she sprayed me with perfume. She brushed my hair which had grown slightly since she had given me a haircut. She tried styling the best she could but my hair was too short to work with. I helped that morning by cleaning the house and doing the washing. Amy had shown me previously how to iron my camisoles and blouses.
During the afternoon, she had me practice applying makeup. Once it was put on, I had to cleanse my face and start over until I became competent in making up my face. That evening, Amy decided that we would order Chinese takeout. After calling in the order, I was told to pick it up. Amy gave me a small purse containing my wallet and a tube of lipstick. She went with me but stayed in the car; I had to go into the restaurant to pick up and pay for our order.
I was too nervous to see the reaction of the customers and the counter girl to see a man wearing women’s clothing and makeup. My life was rapidly spinning out of control. Was it really even my life anymore? Certainly, I didn't seem to be the one in control of it. Yes, you could say I deserved punishment for my profligate ways, but was this truly the punishment I deserved? Did any man deserve to be forced to wear women's clothing in public, in his own hometown?
Although I hadn't consciously seen the faces of the other people in the Chinese restaurant, I could hear the comments they made about me. As you would guess, they were not complimentary. My imagination filled in the rest. I could and did picture what they looked like and the faces they must have made behind my back. Those thoughts haunted me for the remainder of the weekend. No matter what I did, suddenly I would have a flashback to my brief time in the restaurant and feel ashamed at what I had done in public in front of strangers.
Monday morning I awoke twenty minutes early since I now required time to make up my face. Amy assisted, telling me not to use eyeliner during office and daytime wear. She gave me a tube of medium pink lipstick to apply, saying I should take the tube to keep my lips freshened during the day. She hinted that she would be stopping by to check on me. Arriving at my office, I quickly went through the front door, hoping no one saw me. Again, I was glad that Peggy was on vacation.
Then it dawned on me, I was fully dressed as a woman, complete with makeup. If I did not collect this week, the final step would be wearing a wig. Once the wig was placed on my head, I would be in skirts and dresses, NOT women’s slacks. I started calling Rodney, trying to get at least a payment, if not the entire remaining balance of the auto loan.
Regardless of being dressed as a woman complete with makeup, I would go to pick up a check, even if it were only for fifty dollars. This would postpone my complete metamorphosis. There was no answer when I phoned. Tuesday, I called several times between doing payrolls. On Wednesday afternoon, I called again. There was a message saying Rodney's phone had been disconnected. My heart sank. I went to my car without caring if anyone saw me.
I knew that unless I could obtain a payment, I was doomed. At the repair shop, everything was gone. There was no notice nor a forwarding address on the door. In the back were a few old wrecks of automobiles. Looking through the windows of the garage, I saw all the furniture and tools were gone. Returning to my office, I called the city property assessor’s office to learn who the owner of the building was. I was able to locate the owner by telephone.
I explained that I had made a loan to Rodney and that I needed to reach him. The gentleman informed me that he, too, was trying to reach Rodney as he owed three months' back rent. He had served Rodney notice over a month ago through the court. From what the landlord was able to learn, Rodney had gone somewhere in Alabama. He had learned that Rodney also owed past rent on his apartment. No one was able to find him, much less collect from him.
This news hit me like a proverbial ton of bricks. I was out over a thousand dollars, plus I seemed doomed to wear female clothing and a wig for the foreseeable future. My head was spinning. Momentarily, I considered driving my car into the nearest brick wall, before I realized that I did have a wife to think of, even if she was the one forcing this horrible situation on me. While suicide was a way out, it was too drastic to follow through with.
I gripped the steering wheel and forced myself to stay on the road and resist the temptation to make a sharp turn into an immovable object. I was so devastated by the news, I ran into our home, threw myself onto our bed, and cried. By five-thirty, after several drinks, I thought, “Perhaps if I prepare dinner, maybe Amy will have a change of heart and release me from our agreement.” Upon arriving home, she was surprised to find me in the kitchen cooking dinner.
Amy was pleased with both my appearance and the fact that I had prepared dinner. Finally, as we were about to finish, she asked about my day. After telling her the bad news, I pleaded with her, “Amy, I understand that I was completely wrong in spending the money on a stupid football bet and making the loan to Rod ney.
I'm sorry and ask for your forgiveness.” Amy told me that while she did understand, she was still angry about not being able to spend our anniversary on a cruise along with several couples from work. I pleaded, “Can't we just forget about our wager? I can not go into the office next week completely dressed in women’s clothing. What will Peggy and my friends think?” She replied, telling me that my friends must not have mattered as I had been wearing female clothing and never bothered to see nor talk with them.
As far as Peggy was concerned, Amy would explain the situation to her Monday morning. Amy was planning on taking a week's vacation in order to help prepare me for my new role as a woman. “Yes, you will continue wearing dresses until you have really learned your lesson.” “In the meantime,” she told me, “wearing feminine apparel will constantly remind you of your misgivings.
We will be shopping for the ‘New You’ this coming weekend.” I had left a message for my secretary telling her that I would be on vacation for the next week; I had been informed by my wife that we would have a week of instructions helping me to act feminine so I would not draw attention to myself while dressed in feminine clothing.
Saturday morning, I showered after spreading the depilatory lotion over my body. I was told to wear my fanciest undies as well as grey pants and a blue blouse. Amy watched as I applied makeup. This time, she handed me red lipstick and a tube of gloss for my lips. The first stop was a wig shop. After an hour of trying on wigs, Amy decided on a medium auburn wig with a wave over the forehead and a loop going back to the main body of the hair. In the back, there were curls turning outward from the neck. I left the shop wearing the wig.
Our next stop was the beauty salon, where both Amy and I had a manicure. I had an extensive set of nails glued onto my natural nails, then three coats of bright red polish were applied followed by a clear sealer coat of polish. We stopped for a salad and a half-sandwich before continuing our shopping. The first stop of course was a woman’s lingerie shop. I was fitted for a pair of realistic falsies. The clerk had me remove my blouse, camisole, and bra before bringing out several pairs.
Once I was fitted, the shop owner glued the breasts in place, giving Amy the balance of the glue and a solvent to use whenever necessary. The falsies filled my bra cups. I could feel the weight shifting to the straps on my shoulders. I then purchased four more sets of panties and two bras as well as a high-waist open-bottom girdle. The owner also suggested that, in order to give me a more convincing figure, I should wear a waist cincher. It reduced my waist by two or three inches.
With packages in hand, we went to the car, put the packages in the trunk, then went to the department store. Amy enjoyed my embarrassment. I looked like a woman until I spoke. Of course, she would continually ask questions as she selected nightgowns for me. They were as feminine and frilly as possible, including a soft pink pair of baby dolls with a bellowing short skirt and small thin straps holding the nightie on my shoulders and a matching set of fluffy panties. The clerks did not know what to think as Amy saw to it that I answered her questions.
The ladies shopping in the department, knowing what was happening, stood and watched as I was handed one nightie after another. Then we looked through the slips, finding a white fully laced model. We purchased two white slips and one pink slip of a similar design. From the lingerie department, we went to the Misses department. Here, I bought three dresses for the office. One was form-fitting, and the others had flared skirts.
All were in bright colors, one with a Shawl neckline, one with a Peter Pan collar, and the third with a plunging “V” neckline. In the Sportswear department, I tried on various types of sweaters before deciding on a white and a pink set of matching shells and long-sleeved cardigans in soft lamb’s wool. Amy selected a tight navy blue skirt as well as a red knife pleated skirt and a black straight skirt.
We also purchased several nylon blouses for office wear, one in a pleated tuxedo style, one nylon white see-through blouse with long French cuff sleeves, and another with an Ascot neckline with three-quarter sleeves. From the department store, we went to the shoe outlet and bought myself a pair of red three-inch heels, navy pumps, and a pair of bedroom slippers with three-inch narrow heels. Back at home, I was instructed to put everything in my dresser and closet after removing all my male clothing. I put them into my footlocker and old suitcases.
Amy said we were going out to dinner. I was to wear one of my new dresses along with the waist cincher which I presently had on. She came into the room to supervise as I did my face for the night. We went to a very fancy Italian restaurant in the far suburbs of our city for a lovely dinner. Amy made sure our table was in the center of the dining room. She had put on one of her better dresses and high-heeled shoes for the evening.
Sunday morning after sleeping late, Amy searched the morning paper and found several estate sales. I was told to dress in the tight black skirt over my new girdle, white lacy panties with matching bra and camisole along with the white sweater shell and cardigan. She did my makeup, reminding me that I would be doing this from now on. Amy drove to a house in an affluent neighborhood.
There, we purchased many pieces of costume jewelry with clip-on earrings and several sets of screw-type earrings. Looking through the clothing, Amy found several dressy suits and two coats, one dressy, the other for regular day wear, that would fit me. Later that afternoon, she had made an appointment for a make-over at one of the local boutiques that handled cosmetics.
After an hour of trying various colors in both foundations and eye makeup, we went to the drug store and bought application brushes, polish remover, and nail polish as well as a bottle of “White Diamonds” perfume. Monday morning, I was dressed in my blouse and a skirt as Amy taught me the proper way a woman walks, sits, and stands. I practiced raising my vocal pitch and how to modulate properly. In the afternoon, she had me reading aloud, trying to raise my voice.
She went on an errand while I practiced. The balance of the week, Amy had me practicing both day and night until she was convinced that I not only looked like a woman but acted like a woman. Part of my brain told me that a man should not be behaving like this. Another part of it, however, said that, finally, the inside was beginning to resemble the outside.
After all, I had been wearing women's clothing for weeks now. Would a real man allow that to happen? I felt guilty about not fighting my feminization harder than I had. Maybe I should just have refused to put on those panties weeks ago. Maybe. The fact was, though, that with each passing week, less and less of me was objecting to my situation.
More and more, while I still went through the motions of objecting to my feminization, I was feeling comfortable in the frillies. We went out to dinner Friday night. Amy had me order my own dinner. I was surprised that the waiter did not look at me oddly as he took our order. When we had completed our meal, he said, “I enjoyed serving you. I hope you LADIES enjoy the balance of the evening.” Saturday, we went for a drive and a long walk downtown before stopping for dinner. Sunday night, it dawned on me that I would be returning to work in the morning.
I asked Amy how we were going to tell Peggy about this change. I was told, “Do not worry about Peggy. I went to your office Monday afternoon and explained to Peggy what's been going on. She thought something was up as you acted rather strangely the last couple of months. She is expecting you to be wearing a dress tomorrow. I am not sure she would recognize you if I had not informed her. I will be taking you to the office tomorrow as you had better not drive until you get a new driver’s license.” Monday morning, Amy laid out a pink lacy bra with matching panties, my pink slip, and a pink garter belt along with a cincher, panty girdle, and sheer beige nylons.
Once I had dressed in the feminine undies, I did my face as I had been taught, after shaving closely. Amy had breakfast waiting as I put on her duster over my undies. Returning to the bedroom, I put on the red pleated skirt along with the pink shell sweater and the necklace, bracelet, and earrings that complimented my outfit. After putting on the cardigan and taking my red purse which we had brought at the estate sale, I was ready to go to work.
Amy walked in the office door before I did. “Peggy, I would like you to meet your new employee, Cindy Brown. If you would show Cindy her desk and office, I will inform her about the new organization.” Peggy admired me. “I had no idea that you would be so pretty. I love your outfit. Don't worry, Amy explained the situation to me. Here is your new office.” She led me to the office she had once occupied. I saw that she had moved all her personal belonging into my old office.
Amy then informed me, “Cindy, dearest girl, as you have surmised, Peggy is your boss. I had a long talk with her on Monday. This business is small and can remain that way. Peggy and I realized that there has been a lot of time that could be put to better use. She is going to do the selling and handling of the customers in the future. You will do all the computer data entry, making sure the checks and reports are completed and delivered to our customers as well as being the Girl Friday in the office.
In the meantime, Peggy will work to double our sales while increasing our profit margin.” “I will be handling the accounting in the future. Your hours are from 9 to 4. I expect you to prepare our dinners from now on and help clean our house.” Thus my new life began. Things went exactly as Amy said they would, as I now realized they would, as I feared they would. “Feared” is the past tense, you may notice. That is the correct tense as I have now settled into my new role, a role the “old me” never dreamed could be my destiny.
As a man, I never even fantasized that I could be anything but what I was. If anyone had told me how things would turn out for me, I would have thought they were crazy. Not in a million years could I have envisioned what I would turn out to be: a pretty housewife. I was a man, damn it! Was. Look at me now. There is no man to be seen. I am now a pretty housewife and office worker named Cindy Brown. And I am happy.
The End.