She asked, “How long have you been wearing women’s clothes?”
Sheila Compton had everything going for her. She owned a real estate company with five offices in three cities. She was active in the community and was a volunteer for different charities. It was the middle of the morning and she was headed home to grab a copy of the budget for one of the charities she was on the board for. She thought she would slip in quietly so as not to disturb her husband of seven years. She knew he would be on his computer doing his job as a software engineer.
She quietly slipped into the house to grab the papers in their bedroom. As she passed her husband’s office she glanced in. She saw him intent on his computer screen. She noticed the floral shirt he had on. As she grabbed the papers she thought he doesn’t have a floral shirt.
She stepped into his office. She made a little noise clearing her throat. He turned toward her. She saw the lace trim on his shirt. He stood up as his face got redder and redder.
When he stood up she saw he had a dress on. She said, “What the hell are you wearing?”
He answered, “It isn’t like it seems. Let me explain!”
She cut him off saying; “I don’t have a lot of time for talk right now. We’ll talk about this later.”
She saw a key lying on the corner of his desk. She asked what it was. He said it was the key to his belt. She grabbed it.
She said, “I guess I don’t need to tell you that you better be wearing those clothes when I get home. If you are going to wear those clothes get some lipstick on.”
He said he didn’t have any. She told him there was plenty in the bathroom drawer and he better look presentable when she got home. Then she turned and left.
He sat shaking for the longest time. He never expected her at this time of day. He figured he was dead meat now. He wondered what she would do, leave him or kick him out.
At noon he went and had a sandwich and glass of milk. He usually had a sweet roll with his lunch but today he didn’t feel like one. When he finished eating he was going to go back to his office. He put the dirty plate in the sink and heard his heels clicking on the hardwood floor. He then remembered Sheila telling him to get some lipstick on. He had never worn lipstick before. He hadn’t worn any make-up before. He stopped at he bathroom to go to the toilet. Then he looked in the drawers until he found the lipsticks. He took one and opened it. It was a brown shade. He thought about how Sheila looked when she wore that. He put the cap back on and grabbed another. It was bright red and he held it by his dress and saw it was almost a perfect match with the roses that were on it. He applied some to his lips. It didn’t look right. He washed it off and tried again. This time it looked better.
He was working on his latest program when Sheila came home. She headed straight for his office. She told him it was time to talk. She said she would see him in the living room.
He finished up and went to talk to her. He was scared of what she might do. She was sitting looking very upset. He knew he didn’t want to upset her any more than she was now. He sat down in the easy chair facing her.
She had watched him come in. She noticed that he moved with ease in those heels. She thought he has had a lot of practice in those. She knew she was angry and she didn’t want to lose it and blow everything. She just wanted to find out why he was dressed like that.
She asked, “How long have you been wearing women’s clothes?”
He said, “It all started when I was about ten years old. One day we were home alone and my sister dressed me in her clothes and had me do the dishes and help her around the house. The next morning when she woke me up she had me put on another of her dresses and help her with the wash and then had me sweep and mop the kitchen floor. After that for the next couple of years about once a month she would have me put on one of her old dresses and help her. This went on until I was sixteen then she stopped. I would sneak into her room when everyone was gone and try on her clothes. I know she knew because she left a note on one of her dresses one time saying try this one on. After I graduated from high school I quit dressing up. I thought I was over it.”
Sheila asked, “When did you start again?”
He replied, “About five years ago. I stopped at a garage sale and saw a dress that caught my eye. It looked so nice I couldn’t help myself. I bought it and hung it in the spare bedroom closet. It hung there for a month then one day I tried it on. It fit beautifully and I had to get the underclothes and shoes for it. I went to Wal-Mart and got the underclothes and stockings and then went to a self-help shoe store and got a pair of heels. After that it just escalated. Now, maybe one day or two days week I put something on for the morning and after lunch change back.”
Sheila said, “Well, you were overdo to get caught. I have stopped home before and you never had anything like that on. Was there ever a close call?”
He answered, “No, you never came home when I was dressed. I guess I was just lucky.”
She asked, “Do you really like how a dress feels on you?”
He answered yes that it felt different and he felt like a different person.
Sheila said, “Well, John, I guess it isn’t as bad as I thought but you let me down. I thought we didn’t have any secrets from each other. That hurts the most. You owe me big time for that reason alone. I think you should be punished don’t you?”
He replied, “Punished? What are you talking about?”
She said, “You did something wrong in not confiding about your dress to me. I have in mind what could be called pleasant punishment. Are you willing to accept your punishment?”
He saw she was settled down considerably so he agreed to whatever she wanted. He asked her what she had in mind.
She said, “Seeing you like to wear dresses you can continue to wear woman’s clothes 24/7 until I tell you you can stop. How does that sound?”
He said, “It don’t sound bad, but what if we go out?”
She said, “That’s the chance you take! Either accept the punishment or I get upset and I don’t know what will happen.”
He heard and felt the ice when she said that. He accepted her punishment. She asked him how many outfits he had and he told her probably a half dozen. She said that was enough for a fashion show, maybe tomorrow night. She asked if he had a wig or anything like that. He told her no and that he had three bras, two panties and two slips. That was all.
Sheila told him to come in the bedroom with her. Once there she unlocked his belt and told him to take his dress and slip off. She put a pair of her panties in each of his bra cups then handed him a pair of her tan slacks to put on. She said they were from when she was heavier. They fit him pretty good. She handed him a blouse, which he put on.
Then Sheila said, “The stores are open for a little over two hours yet. We are going to get you a wig. There is a wig shop in the mall where we can get one. Let’s go!”
He didn’t want to refuse so he said there were no pockets in the slacks. Sheila handed him a clutch purse to carry his wallet in. She told him to redo his lipstick so they could go. He asked about his shoes and she told him to keep the heels on. He redid his lipstick and they were on their way.
At he mall they had to walk through Sears to get to the wig shop. At the wig shop the saleslady giggled as she fit a skull cap over his hair then placed a brunette wig that came down almost to the middle of his back. She adjusted the bangs and fluffed it a little. They took it and he felt better now that he looked more like a woman. Sheila led him out of the store and instead of heading toward Sears she went the other way. He followed. She led him to a medical supply store. She talked to the clerk and soon the clerk came out with four different pairs of breast forms. Sheila selected the largest ones filled with silicone and guaranteed to look and feel natural.
Then she led him to an earrings place. When they left he had three studs in each ear. Sheila had also gotten him two pair of dangly earrings. Then they stopped at Victoria’s Secret and she got him a half dozen of the laciest panties and fanciest bras he had ever seen.
He complained his legs were starting to hurt so she stopped at a shoe store and they got him two pair of flats. He wore one out of the store and immediately his legs felt better. They stopped and got a sundae at an ice cream shop. When they finished Sheila said it was time to go home.
On the way back to Sears, Sheila spotted a sundress that she thought would be perfect for him. They went in and before he knew what was happening he found himself in a changing room trying on a sundress. When they left he now had two sundresses.
They got home and he put the clothes in his closet and dresser. He was tired and when Sheila came in he told her he was ready for bed. She told him to undress but hen let know when he was so she could attach his breast forms. She attached them and he said they were so heavy that he might fall on his face. They both laughed. She then handed him one of her old nightgowns. It was a full-length nylon gown with what seemed to him to be a lot of lace.
When he got up the next morning Sheila handed him a panty girdle to put on. It was very tight but she said it would keep him feminine looking. Then she took out a green silk dress with yellow flowers decorating it. She said it was one from when she was larger. It fit him but was a slight bit tight. He was going to put on a pair of black flats but she asked if he had a pair of white shoes. He said he did and she told him to put those on instead. He put on the white strappy heels. He didn’t especially like them as they had four-inch heels.
As they were eating breakfast Sheila told him that as long as he was dressed as a woman he could do some cleaning, like change the bedding and cleaning all the carpeting in the house. She told him he better keep all of the clothes on and keep his make-up looking nice. She left for work and he started the cleaning.
On the way to work she thought about his dressing and how good she felt when she told him to clean the house. She knew she got a wet spot down below when she told him that. She remembered the look on his face when she had picked up the key to his belt. She wondered how far she could go.
He finished the cleaning before noon and decided to eat an early lunch before starting work. He liked the feel of the silk dress. He had never worn a silk one before. After lunch he redid his make-up and went to work. It was almost impossible to work given the erotic feelings he was getting from the clothes. Finally he gave up on the work.
He went into the living room and instead of turning on the TV like he usually did he just sat and thought about what was happening. Sure he was being punished but it was delightful. He thought about how lucky he was to have Sheila. He decided to do something special for her.
He went on his computer and made a special thank you card for her. It thanked her for being his wife and being so understanding. It had a heart with an arrow through it. He was pretty proud of it.
Sheila was on her way home and thought about John. She thought about taking some of the pleasant out of the punishment. She didn’t know how he would take it but wanted to give it a try. She thought if she pushed him a bit he would want to stop the dressing like a woman.
When she got home the first thing he did was give her a kiss and hand her the card. She looked at the card and gave him a kiss and thanked him for the beautiful card. She had second thoughts about pushing him then decided that pushing him was the only way to end his dressing.
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