Clothes Gone - Part 3

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The following week, I was sentenced to wear the camisole.  I was able to get Rodney in his office alone for a minute. I pleaded with him, telling him about the agreement I had made with my wife. Unbuttoning my shirt I showed him the pink bra with the matching lacy camisole I was wearing. I told him, “Rodney, I need you to pay me each week.

I am wearing this brassiere because I could not collect your weekly payment. My wife is making me wear women’s lingerie under my street clothes until I collect the money you owe me. Please help me. The only way I can get rid of the brassiere is to collect from you each week.”  “Man, what a bummer,” he replied while staring at my hairy chest covered with a pink lacy feminine bra, and fancy silky camisole. Laughing, he continued, “Your wife must be a bitch. I will try to see what I can do next week, but today, unfortunately, I do not have any money.”  He kept a straight face, but I thought I could detect a hint of a smile. Could I blame him really? Think of the position I was in.

Although he was technically in my debt, I was the one confessing to wearing female undergarments. I was forced to think that he must be laughing at me in his mind.  Not having a check to show Amy, I knew that in the morning I would be adding a very feminine spandex panty girdle with satin front and rear along with my other lingerie under my shirt and trousers. I considered getting cash to hand to Amy, telling her that it came from Rodney, but I had no way to receive cash without writing a check, and, besides, Amy would review the checkbook each weekend.

A horrifying thought entered my mind, “Will I be wearing women’s shoes next?” I tried hard to erase that thought, hoping that I had appealed to Rodney’s sense of camaraderie. He would not let a fellow male down...would he?  Little did I know that he had told his girlfriend that I was wearing a pink brasserie with a very lacy pink ribbon camisole last week, along with the rest of the story I had told him. His girlfriend apologized to me that Rodney had to go pick up some parts and would be returning around five. I waited, passing the time and talking with his girlfriend. After a while, she asked me if I was wearing a bra today.

Knowing that she was examining me closely and could notice a faint outline of the bra cups and of course the adjustment on the shoulder straps of the bra, I confessed, telling her about my bet with Amy and that was the reason I needed to see Rodney this evening. She told me that Rodney mentioned that I would be visiting but had not left a check for me. I waited until six before going home.  During my drive home, I assessed my situation. Not only was Rodney not paying up, but he had broken our unspoken agreement not to tell anyone about my situation. How long would it be before everyone I knew heard about what my wife was putting me through? At that point, Rodney would essentially be blackmailing me.

What leverage would I have to get him to pay the rest of his debt at that point?  Amy had dinner waiting when I got home. She kissed me lightly on the lips as her hands went around my back, touching the outline of the bra I was wearing. She did not say anything about my not receiving a check from Rodney. In bed that evening, she stated that we would be going shopping in the morning to find suitable slacks for me to wear. We stopped at a lady's boutique Saturday morning. The young clerk asked Amy how she might help. “We are here to purchase some pants for my husband.”  “I am sorry but we do not carry men’s pants. We only have ladies' clothing,” replied the clerk in a tone, implying that Amy should have known better.

Amy smiled and said, “Dearie, I realize that this is a ladies' shop. We are here to find suitable WOMEN’S pants for my husband. Would you be kind enough to obtain the size we need? Please show me grey and black pants with a back zipper or a side zipper so he may be sure his new pants will fit him.”  The clerk replied, “I am sorry, Madame. I should have known better. Let me get a tape to measure your husband’s waist and I will be glad to assist you.”  Put yourself in my position. I was standing in a women's clothing store with my wife who was explaining to the young, pretty clerk that I was there to buy some women's pants.

If you think that I was mortified, you would be correct. The clerk recovered from her obvious surprise and acted in a professional manner, but I could imagine what she must have been thinking, and it could not be flattering to me.  Determining that I would wear a size 14, the clerk showed us the rack and started looking for pants. She found a pair of medium gray pants with a rear zipper. “Perhaps you would like to make sure that these will fit your husband.

Our dressing room is in the rear. If you follow me, I will show you. Then I will find a pair of black pants with a rear zipper for you,” the clerk told Amy.  In the dressing room, Amy told me to remove my shirt, pants, and shoes. I stepped into the lined Dacron and polyester pants. Amy stepped behind me, hooking the snap and closing the zipper. She then adjusted the side-belted buckled waistband. “The pants are a good fit although you need a little padding to fill out the butt. I have the perfect solution at home that should allow you to have a rounded tush.”  The clerk came, in carrying a pair of black pants with a rear zipper and a high-waisted belted front.

She watched as I took off the gray pants, now exposed in my lacy undies. Her mouth dropped as she covered her giggling the best she could. She stayed in the room as I put on the black rayon and wool pants. Amy was pleased as both pairs of pants would require me to unzip from the rear when having to go to the bathroom. She liked the pants because there was only one small pocket on the left side which, she pointed, out would hold a tissue and maybe a tube of lipstick.

I left the store wearing black pants knowing that everyone in the store knew I was wearing women’s slacks. With the zipper in the rear, there was no doubt as to the gender these pants were made for.  Arriving at home, Amy had me take off the slacks. She went to her dresser going through her lingerie drawer until she found a small panty brief with a padded derriere. I struggled into the small but powerful piece of lingerie. The brief put pressure on my stomach, flattening out my front, compressing my manhood, and giving me a rounded butt.

When I put on the pants, my rear was smooth as well as the front of the pants. Amy read just the belt buckle, taking in about a half-inch on each side of the waist.  Amy had me walking up and down the bedroom turning and posing. She told me, “The padded brief is just what you needed to complete your look. Put on your shirt, take a jacket and we will go out to dinner.”  I was embarrassed as we walked through the restaurant.

It seemed that we had to walk several blocks until arriving at our table. I was aware that several women were whispering to their friends as I walked by; they noticed my pants had a plain front and the zipper was covering a fully rounded derriere. Since I had no pockets to carry my wallet, Amy paid for dinner.  When I asked how I was supposed to manage during the week without a place for my wallet, she said, “ Charlie darling, you will just have to figure out something. I know you can arrive at a solution. If all else fails, you can always use one of my purses!”

“Please do not joke about this problem. It is bad enough that people will realize I am wearing lady's pants. How am I going to keep it a secret at work? Why did I ever agree to this?” I asked.  “Maybe you will be able to collect these next two weeks so you can return to wearing your male slacks,” she stated.  The next week at work I was perfectly miserable as I tried to hide in my office not exposing my new pants to Peggy. I tried to keep Peggy busy and had her running errands as much as possible. One day, as I was leaving my office, Peggy said, “Charlie, for some reason this past week, you have had a different look about you.

You must have lost some weight. Your stomach appears to be smaller and you appear slimmer.”  That evening, I pleaded with Amy, telling her that I was sure that Peggy realized I was wearing women’s pants and she might learn that I was also wearing bras. What would happen if she knew that I was wearing lady's lingerie?  “I am sorry but you should have thought about the consequences when you made the wager. Maybe your male ego told you that you could not lose and you never thought that you would be faced with wearing feminine apparel,” she said, smiling.  “Maybe Peggy thinks exactly what she said, that you've lost some weight. Probably she has not even noticed any change in your clothing. Most people are too wrapped up in themselves to even notice something like that,” she advised me.

It was time again for me to have my hair cut but wearing feminine pants, a camisole as well as my other undies, I would not dare to return to my old barbershop. My wife suggested that she could trim my hair that evening. I was surprised that she did a good job using her hair scissors and the trimmer on my electric razor. She left the back a little long for my liking but did a good job on the sideburns and around my ears.

The very next morning, I called Rodney three times, leaving word for him to return my calls. Finally, around four that afternoon, I caught him at his shop. He promised that he would have some money for me that Friday. It was subtle but I could swear that he was annoyed by my politely asking him for the money he owed me which he was overdue on. “Rodney, it's very important that I collect last week's payment as well as the payment for this week.

Can you please make an effort to pay both weeks?” I pleaded with him. I figured that on Friday, I would ask him to pay the $1500.00 remaining on the loan in full by the following week. Then I could return to normal. My agreement with my wife stated that when the loan was paid in full, I would gain back the privilege of wearing my masculine clothes. Friday and the following week, I would devote my focus to having the loan repaid in full.  Friday afternoon, after waiting for close to an hour for Rodney, I received a check for only one week’s payment. I am not sure he noticed my feminine pants even though I tried to hide the back zipper by wearing a sweater over my shirt. I was disappointed in receiving only fifty dollars but I informed Rodney that I needed the balance of the money next week.  Rodney told me that it would be impossible for him to pay the loan in full next week but he might possibly be able to pay me within the month. I had screwed up by not requiring him to sign an agreement.

If I was not so preoccupied with trying to keep him from seeing what I was wearing, I would not have made the mistake of not insisting that a lien be placed on the car's title, naming me as the lien holder. I was able to obtain only a promise that he would try to see what he could do about making at least two additional payments the next Friday. Gee, how nice of him. Since he understood my situation, you'd think he'd do everything he could to help me out instead of making the half-hearted promise to “try” to have some money for me soon.  Very little was said that evening as Amy and I ate out at our favorite Chinese restaurant. I gave Amy the fifty-dollar check during dinner. From the look on her face during dinner, I knew that soon I would be exchanging my shirts for blouses.

My fear that Rodney might blackmail me seemed more realistic with the passing of each week without full payment of his debt. I felt as if I was falling into an abyss with no bottom in sight. Next week, again I did not get a check from Rodney. After dining out, my wife and I went to the department store where I tried on several styles of blouses. Amy decided on long-sleeved plain cotton and Dacron blouses, one light blue, one tan, and one white. I considered myself lucky as we had looked at nylon blouses, some with pleats, some with sheer sleeves, and others with detailed flowering in various colors. I left the store wearing the light blue blouse, which might have passed for a man’s shirt except it was cut tighter and buttoned on the opposite side.

The weekend was sheer misery for me. Now the only masculine clothing I wore was my shoes. Amy kept kidding me by saying me how much nicer I would look wearing heels instead of my bulky shoes. Would I? Really? Was she just saying that or did she really believe it? I wasn't sure what I believed about myself anymore. I did know, however, that being seen in public in women's clothing was not going to be easy, or fun.

Monday morning, I was embarrassed about going to work. Except for shoes, I was completely dressed in ladies' apparel. I was certain that Peggy would now notice that I was wearing a blouse rather than a shirt.

If she did notice, she did not say anything to me. Again I was surprised when Amy came to visit, and suggested that we have lunch together. At her suggestion, we went to a small tea room where we both had a chef's salad and tea. During lunch, Amy suggested that it would be a good idea if we both started a diet and tried to exercise more to firm our bodies.  Returning to the office, Amy spoke briefly with Peggy before leaving. In the afternoon, I started calling Rodney, reaching him on the second try. Rodney told me he was working to get the money he owed me. Desperately trying to believe that he really was trying, I did not bother calling him until Thursday afternoon. Rodney told me that he had just received a court summons and he would not be available until late Friday.

Finally, at five-thirty on Friday, I was able to talk to him on the phone. Because of having to go to court, he had not been able to borrow the money. When I asked him about the possibility of getting fifty dollars, he told me that his wife had the checkbook and she was out of town. My heart sunk into the pit of my stomach. What could I do? The next step was wearing high heels shoes with the rest of my outfits. Everything was lost.

Driving home that evening, I tried to think of ways to end our wager and maintain peace in our marriage. Amy was in the kitchen as I came through the back door. She took one look at me before saying, “I see by your demeanor that you failed in getting a payment for your auto loan today. Care to talk about it?”  I told Amy that Rodney had promised that he would try to pay me the entire balance of the loan this week but wasn't able to follow through. I had high hopes, though, that he would come through for me next week. I said it but in my heart, I didn't believe it. After all, Rodney had not given me any reason to think that he cared about helping me. I certainly could not rely on his assistance.  “For your sake, I truly hope that he pays you in full. I do not wish to embarrass you further. We'll purchase some heels for you tonight after supper.

Since you may be paid entirely next week, we will only buy one pair. Now, let's finish our supper. I have broiled some fish. We will have green beans and a small salad for dinner as I am trying to cut back on the calories we eat.”  Not a word was spoken during dinner. I was ashamed knowing that in a few hours, everyone I came in contact with would see I was wearing high-heeled shoes. They would then realize that I was wearing a blouse and pants without a front fly. Helping Amy clean up the kitchen, I desperately pleaded with her not to continue with our wager. I told her that she had made her point and I was totally sorry for losing our money.

I tried to sound as contrite as possible. I had taken a few acting classes back in my college days and I tried to remember how to project sincerity.  Amy thought the matter over before informing me, “No, I expect you to abide by the terms of our agreement. When you get paid in full, you can return to wearing your male clothing. In the meantime, freshen up. We are going to buy your first pair of high heel shoes.” Apparently, my acting wasn't good enough to sway her.  We went to a discount shoe store where customers waited on themselves.

Amy suggested that this would be less embarrassing for me than going to a department store or a ladies' shoe store. This may have been true except that when we entered the store, a clerk asked us if she could help. Amy informed the lady that she needed to have my feet measured; I was looking for a pair of simple plain-toed black pumps with a three-inch spike heel. The clerk was slightly stunned at Amy’s announcement but had me sit while she removed both my shoes. Seeing I was wearing nylons, she took the measurements.

I could tell that she was trying not to make eye contact with me. I can only assume that she thought she would not be able to hide her amusement if our eyes met.  She returned carrying four boxes. She had two styles of pumps in two different sizes. Opening the first box, she slipped a pair of shiny black patent leather pumps on my feet. Amy had me make my way up and down the aisle until I could walk without teetering. I told her the shoes were slightly tight. The clerk had me slip on the second pair, a size wider, which felt more comfortable.

Opening the next box, I tried on a simple plain pointed-toe black leather pump. Since the size 9 A fit, Amy decided that the plain pair would be perfect. She asked the clerk to wrap up my male shoes as I would be wearing the high heel pumps home. My face was crimson as I followed Amy to the cash register with the clerk walking behind us. She asked Amy where I bought the pants I was wearing as she had been unsuccessful in finding rear zipper slacks for herself.

Saturday morning after showering and dressing completely in women’s clothing from head to toe, I approached my wife, pleading with her not to make me wear heels as everyone would realize that I was dressed totally en femme. Besides, I argued, Rodney would be paying in full within the next week or two. I tried to cover my bases in case he needed a second week. I may have said it but that doesn't mean I really believed it.

Amy considered my pleading, saying, “ You know the terms of our wager. If he does not pay you in full next time, you will be wearing makeup. The following week will be a wig. When you wear the wig, you will be completely dressed in ladies' clothing including skirts, sweaters, blouses, or dresses.”  “Is there anything that could be substituted in place of the high-heeled shoes?” I asked. If I could delay wearing heels to work, Rodney would come through and I would soon win my wager.  “If you are serious about not wearing heels, I will offer you a substitute, if you are willing.

This would be your choice. If you remove ALL the hair from your body, including shaving under your arms, I will let you do that instead of wearing heels this week. Is that agreeable to you? However, remember, the next time a payment is missed, you will be wearing your heels. However, if you do decide to substitute, you will still have to wear your heels when you are home this week. What is your choice?” she asked.  I did not have to think, I chose to remove my body hair. Amy told me to go into the bathroom, strip to my panties and bra, then call her. She came when I called, carrying a razor and shaving cream as well as a bottle of lotion.

Having me rinse my armpits, she lathered under both arms, then shaved the armpits clean. She had me take off my panties and bra before covering me from head to toe with the liquid. She informed me that I needed to wait ten minutes before entering the shower, then I should rinse my body. She applied the depilatory over every inch of my body except around my scrotum. I was itching like crazy until I rinsed in the shower. Using the washcloth, I removed all the hair from my arms, legs, hands, and chest. Amy opened the shower door and took the washcloth to my back. I watched all my body hair disappear down the drain.

When I came out of the shower, Amy gave me a huge towel, then showed me how a woman dries herself by patting her body. This was to keep my skin smooth. Then she rubbed on a soothing body lotion. As I slid my panties on, I could feel the soft nylons rubbing across my naked legs. When I pulled the stocking over my smooth legs, I felt a sensation like I had never experienced previously. When the nylons were taut from being attached to the snaps of the garter belt, the feeling was overwhelming.