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Winky Dink By Margaret Jeanette Toby and Margaret Bower were making love. Margaret wished he was better endowed as he could just reach her magic spot sometimes. This was not the time. She just wished she could do something about it. The next morning she said to him, "We have been married for five years and I think only twice in those five years you have managed to hit my magic spot when we are making love. Why don't you check with a doctor to see if there is something to make your tool larger or longer? You are pretty small in that area!" "I don't need a doctor! Did you ever think about the fact that maybe your magic spot might be recessed?" "I am only asking that you ask a doctor if he thinks he can help." "I don't want to talk about it!" He knew she could be mean at times but she always was sorry for it afterward and would be very loving. He knew she hated her father because he always punished her. He wondered if sometimes she thought of him as her father. The subject was dropped, with Margaret feeling bad she'd mentioned it. She knew he was touchy whenever she said anything about his sexual ability. Three days later they were shopping at the town's mall and walking down the concourse when they heard a woman shouting, "Hey, is that you Winky? Tammy? Is that you? " He recognized the voice. Joyce, a girl he'd known in high school. There was only one Joyce who had a loud voice like that. He urged his wife to keep on walking. He heard hurried steps coming up on them. A hand landed on his shoulder and spun him around. "It is you, Winky, isn't it? I never thought I would ever see you again after you moved away. Isn't this a small world? You remember Dirk, don't you? Well we've been married for four years now." He looked at Dirk and bad memories came into his head. He had bad memories of high school, where both of them had been his chief tormentors. "Aren't you going to introduce your friends, Toby?" his wife asked. "This is Joyce and Dirk Duggan, Margaret. I knew them in high school. We don't have a lot of time so we have to get going." Margaret asked, "She called you Dinky, and then I would swear it was also Tammy. What was that all about?" "It was nothing. Let's get going!" Joyce spoke up, "I can tell you but it's a long story. As long as we're near the food court, if you have time we can get a cup of coffee and I can tell you about it." He was mortified when Margaret said, "I would like to hear all about it. He never told me anything about when he was in school. Toby, go to Haroldson's and get me a pair of suntan pantyhose. I am going to have a cup of coffee with your friends." He walked off his shoulders sagging. As he walked he remembered those awful high school days. He hoped Joyce wouldn't tell Margaret all about everything that happened way back then. He had thought that by moving two hundred miles away he would never meet any of his old schoolmates. He felt a sense of dread. Meanwhile Joyce was telling Margaret the story. Margaret couldn't believe what she was hearing. "The story starts when we were juniors in high school. One day after physical education the boys were taking a shower and one of the boys noticed your husband's small pecker and said something, and they all started calling him Winky Dink for his small pecker. Of course the word got around and everyone started calling him Winky Dink. Then one day at noon four of us girls managed to get him surrounded and pull his pants down. We laughed at his small member and one girl who had a locker right there said he should be wearing a dress with such a small member. She pulled the dress out and five minutes later we had him undressed and wearing the dress. I put a heavy coat of lipstick on him and as I was doing that I saw his shoulders drop, and I knew we had him. I added eye shadow and a heavy coat of mascara. He was like a rag doll. He wanted his clothes back but we locked them in a locker so he couldn't get them. One of the girls said he looked more like a Tammy than a Toby so we named him Tammy. He had to wear the dress for the rest of the school day. We didn't know it but when he got home his mother told him as long as he was wearing a dress he should keep it on. His mother it turns out had a real mean streak in her. He told her what had happened and that night she called me and said she wanted to talk to me." "Well, the next day after school I stopped at their house and thought she was going to give me a real lecture about bothering her son. I was surprised when she said she was not surprised, as her son was not the most masculine boy in the world. She said if I dropped any other dresses off that fit him she would make sure he wore them to school. She said then maybe he would become more of a man. I couldn't believe it, and two days later we girls had come up with nine dresses for him. The next day he came to school wearing a dress. The school principal had him in his office and then I was called in. When I explained that his mother had dressed him like that I knew the principal wouldn't want to get involved, it was a family matter. He was kind of spineless. Every day when Winky Dink wore a dress I would apply make-up to him. It got so he would just stand there and allow me to do whatever I wanted." "He has never said a word about his high school days, and now I can see why. I just can't imagine him in a dress." "He did look kind of cute wearing a dress. But I have to tell you about the junior prom. We girls got the idea of dressing him for the prom. We got a dark blue shoulderless prom dress for him. We talked a girl into asking him to the prom. He agreed, thinking she really liked him. When they arrived we met them outside the school. Dirk helped get him into the prom dress, then took him by the arm and led him in. I told him if he didn't stay until the end Dirk would beat him up. When the court was picked he was picked to be in it and had to go up on stage. Everyone laughed, and when it was time to pick the queen everyone called out Tammy. He just about fainted when the crown was put on his head." Margaret was laughing so hard she had tears in her eyes. She couldn't believe her husband had done all of that. She now realized why he had never introduced her to his mother. "I must tell you I have told him to see a doctor about his size. I know he's awful small down there. I can't think of anything to do to make him realize how inadequate he is." "Why not re-introduce him to a dress? He is really kind of cute in one, you know." "I don't think I could get him into a dress. I have no idea how to go about it." "We're in town for two days. We could come over, and I am sure Dirk can get him into a dress. In school he was altogether submissive in a dress, and I'm sure he will be now. Then once he's in one you can take complete control over him. Do you want to try it?" Margaret agreed, and they immediately went to find just the right dress for him. He returned, just missing them. He couldn't find them so he got a glass of soda and waited. Forty five minutes later he heard laughter and knew at once it was Margaret's laugh. He felt relieved to hear that laugh. He saw both of them were carrying some bags. They were both laughing over something. Margaret said it was time to go home, and then surprised him when she said to Joyce that she would see her later. Joyce handed him four bags and he carried them to the car. As he was driving home he asked what she meant when she told Joyce she would see her later. Margaret told him she had given Joyce their address and told her to stop over any time, He told her he would rather not see either Joyce or Dirk again. Margaret didn't answer him. At home Margaret showed him three dresses she had bought. He had to agree they all looked great and that he couldn't wait to see her in them. He said one was especially feminine and would show off her assets wonderfully. When she showed him a nylon baby doll pajama he joked that she just needed the top when she wore it. After supper she asked if he would be a dear and do the clean up. He agreed, and while he was loading the dishwasher he heard the doorbell ring. Then he heard unintelligible voices and when he was done went into the living room. He was shocked to see Joyce and Dirk there. "I invited Joyce and Dirk over so we could talk about old times. I have never heard you say anything about your school days and they were kind enough to say they could tell me about them." "Why don't you go change into a Tammy type outfit so your wife can see how pretty you can be?" Joyce said. "I am not going to change and you can't make me. This is my house and you have no right to even suggest such a thing." "I know what; we will ask your wife if she wants to see you as Tammy. Margaret dear, would you like to meet Tammy?" "I think I would. I laid out an outfit on the bed for Tammy. Toby, why don't you go in and change into Tammy?" "I am not going in to change! Get that idea out of your head right now!" He sat with his arms folded across his chest. Dirk got up and quickly got him standing with his right arm in a hammerlock. He still refused to change. Dirk put more pressure on his arm, and the pain was getting unbearable but still he held firm. When Dirk put still more pressure on his arm he finally agreed to change. Joyce told Dirk to escort him into the bedroom. Dirk spun him around without letting go, and he was sure his arm would break at any time. In they went, and the two women followed. When he was in the bedroom, Dirk quickly got him naked from the waist down. He started to unbutton his shirt, and he couldn't believe it when Margaret handed Dirk a pair of scissors to use to cut his shirt off. Standing completely naked with Dirk holding him in the hammerlock he couldn't believe this was happening to him. He tried to squirm out of the way as Joyce glued breast forms on his chest. Then she attached a strapless bra to him, bending the hooks, knowing that that he wouldn't get it off without help from someone. . He involuntarily lifted each foot as Dirk lifted him a bit so Joyce could get the nylons on him. She wrapped the garter belt around his waist and soon his nylons were attached to the garters. Then she attached a gaff to him telling him it was too big for him but it was the smallest one made, and she was laughing. Then Joyce got an inspiration. She applied a thick coat of lipstick to his lips. She saw his shoulders sag and knew he was defeated again. She told Dirk to let him go. He was now in his rag doll mode, the same as when he was in high school. She put a slip over his head, and next came the dress that he had told Margaret was so pretty. She had him slip a pair of heels on and soon had the ankle strap locked. She said he was already looking pretty, but he just stood there as if in a trance. Margaret had never thought she would see the day something like this would happen to him. Joyce maneuvered him backwards and down onto Margaret's vanity bench. Then she proceeded to do the rest of his make-up. She did him in dark slutty colors and laughed when he made a face of disgust. When she said they forgot that he would need a wig, Margaret said she had one she had worn a couple of years ago on Halloween. Minutes later he was adorned in the chestnut brown wig with curls framing his face. Joyce opened a jewelry box and soon found a pair of clip-on dangly earrings. Then it was a necklace and bracelet. She slid his wedding ring off, saying the way he was dressed he shouldn't be wearing a man's ring. She slid the watch off of his wrist and soon found three rings which she put on his fingers. Joyce stood back and looked at her handiwork. She said she thought she'd done all right, transforming him. Margaret commented that he looked like a completely different person. Dirk joined in, saying he looked just like a Tammy to him. Margaret told him to get the three of them a drink and to serve them on a tray. She smiled when she saw he was having a bit of difficulty walking in the heels. Joyce noticed the false nails kit on the vanity and asked Margaret if she thought he should have long painted nails. She agreed saying she thought that would complete the picture. He served the drinks in the living room, but Joyce got up and told him to come with her. She had him sit down at the dining room table and had him put his hands flat on the table with his fingers straight out. When she was done he had the prettiest pink fingernails of anyone they had ever seen. His cheeks were blushing bright red. Joyce handed him her drink and told him to take a drink. He did as instructed. The two of them stayed for some time, telling how Dirk was an expert witness in an up-coming trial, and they were in town to study the situation so he would be aware of the layout where the crime had taken place. Joyce finally said, "We have to leave and get back to our motel. Why don't you and Tammy come up to visit us sometime? We only live fifty miles away." "That sounds like fun. When can we get together?" "How about driving up next Friday? We have two spare bedrooms and you and Tammy can spend the whole week-end. I'll call some of our old high school friend and we can have a party Saturday night." Margaret said that was a great idea and Dirk drew a map of how to find their place. They left and Margaret told them they would see her and Tammy next Friday evening. "Well, Tammy, I must say you do look really nice. In fact I think I like you looking like that better than the way you looked before." He was getting his senses back now that Joyce and Dirk were gone. He demanded, "This is ridiculous. How could you let them do this to me? Get me out of these clothes right now!" "No, I think you should stay in those clothes for a while. You look so pretty and you must admit you are not much of a man." "I am enough of a man to know this is absolute stupidity. You can't be serious leaving me in a dress!" "I think you should stay wearing dresses until you can truly admit you are not much of a man. You will wear dresses until you admit it, then I will decide whether you should go back to your men's clothes or not." He was shocked. She had never spoken to him like that before. He was enraged that she wasn't helping him get these clothes off. "How could you let Joyce lead you into believing I belonged in a dress? She was my biggest tormentor in school, and you actually go along with anything she says. I can't believe you'd do that!" "Well, I think it is a great idea. Like I said, I think you look better in that dress than you did before. I think you should continue wearing dresses. In fact I am telling you that you will continue to wear a dress until I decide otherwise." He had never heard her talk like that before. He was at a loss. He decided to take a different tact. "I am your husband and I demand you help me get out of these clothes!" He saw an angry look come over her face and she walked out of the room. She returned two minutes later carrying two purses. She handed him one and told him to come with her. He said he wasn't going anywhere. She grabbed his ear and pinched and twisted it, and in those heels he had to follow her. She led him out to the car and got him sitting in the passenger seat. Then she got in and drove. He had no idea where they were going. She stopped when she got to the far end of what was the red-light district of their town. She stopped and said, ?Now you can get out and walk home from here or you can agree to wear dresses until I say you can stop. You have two minutes to decide." She told him when one minute past then with thirty seconds to go. When the time was up she asked him for his answer. He said there was no way he was going to continue to wear dresses. She told him to get out but he wouldn't move. She got out and soon had his door open and told him to get out right now. He refused to move. She reached in and got his ear again. Soon he was standing on the sidewalk. She quickly got in and locked the doors, and then she opened the window and asked him again if he'd changed his mind about wearing dresses. He answered no with a vulgarity, and she sped off. He stood for a minute, and then started to walk home. At the first corner he saw three women he could tell were street-walkers. He walked on past without saying anything to them. He was in the middle of the next block when he heard a man's voice call out for him to stop. He kept on walking. He had taken about five steps when someone grabbed him. He was spun around, and found he was facing the biggest black man he had ever seen. "What are you doing working my block?" "I'm just walking home." "With that make-up on you are just walking home, huh?" "Yes, that is all I'm doing--walking home." "If you are going to use my block you will pay me twenty-five per cent and favors. Now you look like a smart girl so I will not beat you for using my block to do business. Come with me so I can collect on the first of the favors." He held on to his arm and almost lifted him off the ground. He took him just inside a building and all he saw was a small cot. The big black man reached under his skirt and felt him up, and swore when he felt the gaffe. He said that he would have to use the back door or his mouth. He pushed him down on the cot on his stomach. It didn't take a minute for him to have Toby's skirt up and start entering him. Toby felt immense pain as he was entered. He couldn't believe how painful it was. As quick as it started it was over. He was lifted to his feet, using his arm as a handle. "You are now one of Bubba's girls. All of my girls charge seventy-five dollars for a blow job and two hundred for back door entry or two fifty for front door entry. You can work the block anytime day or night. It is a busy block and I know you can make good money. Welcome to Bubba's harem!" "It is true, I was just walking home. I swear it on a bible!" "Sure, sure you were. If that is so then get going!" He walked out the door trying to walk so his rear didn't hurt so much. No matter what he tried it hurt. He gave up trying. A little over two hours later he was rounding the corner of his block. He started sobbing uncontrollably. He walked up the walk to his house and found the door locked. He rang the doorbell. After what seemed to be an eternity he heard Margaret's voice asking who was there. "It's me, your husband!" "Are you going to agree to wear dresses? If you don't agree you can find somewhere else to stay." "Will you hand me my men's clothes?" "You are dressed all right. A dress is more fitting for you. Now are you going to agree to wear dresses or not. It is getting late and I want to get to bed. You have two minutes to decide." "One minute and counting. Thirty seconds. Times up!" "I'll agree, I'll agree. Now let me in please!" She undid the lock and let him in. She saw he was all disheveled and looked terrible. She knew something had happened to him but what? "How was your moonlight stroll? Did you enjoy it?" "No, a man attacked me and raped my rear end and it is all your fault!" "Don't say it is my fault. You could have gotten back into the car if you would have agreed to my terms. All you did is put off the inevitable." "All I want to do is take a shower and get to bed. Today has been a disaster for me. I wish I was never born." "Come on, I'll help you get undressed." She helped him get undressed and before he got into the shower she made him apply hair removal lotion to himself. In the shower he was amazed at how fast the hair came off. When he was done he said he felt like a new man again. She reminded him he was now a woman for all intents and purposes. She said as long as he felt so refreshed he could get dressed again. Ten minutes later he was completely dressed in the same clothes he had worn before. Margaret told him to fix her a glass of warm milk and two pieces of buttered toast. She told him to serve it on a tray. He brought her snack and she told him to wait and he could take the glass and plate back out into the kitchen. He was going to sit down but she told him he could stand and wait. He was standing and he noticed his legs were sore from all the walking he had done in the heels. She finished the snack and said she was going to bed. He followed her into the bedroom. And she asked what he thought he was doing. He said he was going to get ready for bed. She told him she wasn't going to sleep with another woman of any sort. She took him into the spare bedroom and opened the closet door. He saw some dresses and heels in there. "While you were taking your stroll I moved your new clothes in here. This is your new bedroom. You are not to enter my bedroom unless I tell you to. If I am in there I expect you to knock and ask permission to enter. Do you understand?" He said he did and she walked out. He got the dress off after some maneuvering with the back zipper. He saw nightgowns hanging in the closet. When he went to remove the bra he found he could not get the hooks undone. He tried getting the heels off and found they were locked on his feet. He went by her bedroom and knocked. She told him to enter. He asked her to help him get the bra off and if she would unlock the shoes. "You can leave the bra on. For that matter you can keep the shoes on also. That way you will be that far ahead when getting dressed tomorrow. Don't forget to do your make-up as soon as you get up tomorrow morning. Also there is a bottle of perfume I left on the counter. I expect you to use it and you better use enough so I can tell you used it. Now, good night!" He walked out feeling sick. He couldn't believe she could be that way. His whole world was falling apart. He wanted to die as fast as possible. His rear was still sore and he felt like things were completely out of control. He knew she usually got over things pretty fast so all he had to do was ride them out. He hoped this time too. As soon as he laid down after putting on a nightgown he felt sleepy. He didn't realize how tired he was. In a manner of minutes he was sleeping. When he woke up he thought it was all a bad dream but quickly saw it wasn't a dream. He got up, and thought today Margaret would surely change her mind about him wearing a dress. He did his bathroom things, then went into the kitchen and decided to butter Margaret up by making her breakfast. He decided to serve it to her in bed. He heard her stirring so he quickly got the tray ready and hurried to the door of the bedroom. He walked in and announced that he had made her breakfast. He set the tray down and had the look of triumph on his face. "The breakfast looks nice, but I told you that you had to knock and ask permission to enter this room. Why haven't you done your make-up yet? Are you ready to tell me you are not much of a man and should be wearing dresses? If not, go get your make-up on and you better do a good job on it." "I thought maybe you changed your mind about all of this. Think of what you are saying. You don't really expect me to tell you I should be wearing a dress, do you?" "You better get it through your head that you will tell me you not only should be wearing dresses but now I want to hear you ask me to keep you in dresses. It isn't like you never wore a dress before is it?" He got tears in his eyes and said, "Please I beg of you, stop this right now. You've been after met to see a doctor so I will go talk to a doctor, I promise." "Now when and if you talk to a doctor you can ask for breast implants and female hormones. Then we can get rid of those breast forms. Now go and get your make-up on or I'll put you out the door dressed just as you are now. Now go!" He left the bedroom sobbing. He was putting his lipstick on and a change came over him. He lost a lot of his fight. It was old school days returning. He couldn't believe what she was saying. In the bathroom he wiped his eyes with tissue. He slowly and methodically applied make-up, not making it a slutty as he had yesterday. He finished, then looked closely at himself in the mirror. He thought he didn't look bad; in fact he looked pretty nice. He went into his bedroom and picked the purple dress with the wide white lace trim. It was made out of nylon, and the top being tight, it showcased his breasts. When he looked in the full length mirror he thought he looked nice in it. Then he wondered what he was thinking. He felt sick that he was wearing a dress. He went and retrieved the Sunday paper from between the doors. He started reading the paper. He half expected to see an article telling about what was happening to him. Between sections he saw Margaret walk through. Then he heard her on the phone. She said loud enough for him to hear that she would see whomever she was talking to in twenty minutes. He wondered who she had invited over now. She came in and told him he should scrub the kitchen floor. She told him to go do it now. He went and did as she said. He got it swept good and was getting the bucket full of sudsy water when Margaret came out and told him to put away the mop and to do it on his hands and knees. He couldn't believe she wanted him to do it that way. She watched as he got some rags out of the closet and started. She reminded him that he had to rinse it with clear water after he was done scrubbing it. He was just starting the rinsing of the floor when he heard the doorbell ring. He heard Margaret tell someone to come in, and then silence. Then he heard Margaret say for someone to look in the kitchen and see the new housewife. He looked up and saw Henry Carter, his boss, standing there. Henry had his arm around Margaret's waist. Margaret saw the shock on his face and said, "Oh yes! Henry and I have had a thing going since the Christmas party two years ago. You don't really expect me to go unfulfilled, do you? He has a full-sized tool to use, not a midget one like you have." He thought he was going to throw up, seeing this and hearing what she'd said. The two of them then left, and he watched as they headed for her bedroom. He couldn't believe she could be unfaithful to him. But she was. He finished the floor and went back to read the paper. He felt terrible and wondered what to do. Twenty minutes later Margaret and Henry came back with their arms around each other. Henry said he would see him at work tomorrow and he watched as they French kissed at the door before he left. "I can't believe you could be unfaithful to me. How could you do something like that?" "You can't satisfy my needs, so I just found others who could. You really don't expect me to continue wanting good sex and not getting it from you do you? Now tell me you are not much of a man and deserve to wear dresses. Tell me you are more of a woman than a man." He sat mute and didn't answer her. She wasn't about to give up. "Come on, you know you are going to tell me so why don't you tell me now?" "I am never going to tell you that! Get it out of your head!" She was looking at the ads. Suddenly she said Women's World was having a big sale on dresses and that they had to get down there. He quickly found himself holding his purse and she was telling him to get into the car that they were going shopping. From last night he knew he might as well do as she said so he got into the car. Ten minutes later they were in the store. Margaret looked for the most fancy dresses she could find. She held three different dresses against him and picked two. Then she found the perfect dress for him. It was a red satin brocade dress with a side slit in the straight skirt. She put it in the cart and then saw one she knew he had to have. It was a green mini-dress with rhinestones trimming it. She had him try on all of the dresses. He complied but felt stupid trying on dresses. They took them all. Then Margaret saw the panties and bras on sale. She picked panties and bras that were bright colored and lacy. Then she found a cheap woman's watch on sale. Right there were necklaces and bracelets, and she picked some bright gaudy ones for him. Then she stopped at the perfume counter and told the woman she wanted something floral and heavy. He could have sunk through the floor when she sprayed some on him. The scent was so strong it just about overwhelmed him. She took two bottles, as it was on sale. Then she saw the personalized pins lying on the counter. She picked one that said 'Tammy' and told him that now, everyone would know his name. They checked out and before he got in the car she pinned his name pin on him. He looked like he had just been shot. At home after he had put all the clothes away she told him he should thank her for getting him all the pretty things. He gave her a dirty look. Margaret got up and came by him. She slapped his face as hard as she could. He was in shock. "You better stop giving me those dirty looks. Now you will thank me for getting you all those pretty things or I'll slap you silly." "Thank you for getting me all those pretty things." "You can do better than that. Thank me properly and tell what you like the best or you will be seeing stars." "Thank you for all the pretty things. I love them all especially the name pin." "I guess that will be acceptable. Now are you ready to tell me you are more a woman than a man." He turned away and then sat down in the recliner. She told him to get out of it, that she wanted to sit there. He didn't want to get out of it but got up and went to his bedroom for some peace and quiet. His peace and quiet had lasted a half hour when he heard Margaret call Tammy. He reluctantly got up and went to see what she wanted. She told him to start supper after he redid his lipstick and used his new perfume. He did as she said, not knowing why. He made supper, and as they were eating Margaret told him if he'd done what she'd asked before this, this probably wouldn't have happened. He asked her what she was talking about. "The first year we were married I asked you to see a doctor for your small penis. I have constantly asked you to see a doctor but you always rejected the idea. You would never even ask if there was something that could help. As small as it is it might as well not be there. For all intents and purposes now it isn't there. It came to the point where I considered divorcing you, then Joyce gave me an idea. It wasn't her idea but mine to do this to you because you are more like a woman than a real man." "I promise I will go see a doctor and see if there is something that can be done." "It's too late for that! You ran out of time. So now you can wear your dresses and be like the woman you are. You can go to the doctor and see about breast implants and female hormones now!" "What will it take to convince you that I will change?" "I really don't know. Sometimes I think I should divorce you, then I think about the fact that, believe it or not, I still love you. I am all mixed up about this. That is why I am trying this to see if we can work something out." He didn't know what to say to that. He was glad to hear she still loved him but he doubted she would work things out this way. He was depressed that he was going to be wearing dresses for who knows how long. He thought that if she really loved him she wouldn't be doing this to him. Then he thought about the fact she no doubt would tell a judge he wore dresses and the judge would sympathize with her. He hoped they could work this out but he wanted it soon. He was depressed with the thought she had gone outside their marriage to be satisfied and with his boss no less. That night he went to bed dreading tomorrow and going to work wearing a dress. He wondered if he could convince Margaret to let him go to work wearing his regular men's clothes. The next morning he woke up early and made noise making the coffee. He heard Margaret stirring and soon she was in the kitchen. "I don't want to go to work! Can't I wear what I always wore to work? I will change as soon as I get home, I promise." "You will wear one of your pretty dresses, Tammy. I don't want to talk about it and it isn't up for discussion." "What can I say to convince you?" "You can tell me how nice they are and how you really love wearing them. Also, I want you to mean it." He thought for a minute then thought this was his only chance to wear his men's clothes so he said. "I love my new clothes. They are all so feminine. I love wearing the fancy dresses and the make-up. Everything makes me feel sexy. ". "Do you really mean that?" "Yes, I do." "Then there is no problem with you wearing a dress today. You said you love wearing them and they make you feel sexy, so go put on a dress and your make up. You don't want to be late for work." "You said I could wear my men's clothes if I told you that!" "I also said I wanted you to mean it and you said you meant it so go put on one of your dresses, NOW!" He left dejected. She was enjoying her power and even got wet thinking about how she had gotten him to say what he said. He was so gullible. He got dressed and got his make-up on. When he came out of the bathroom Margaret was waiting for him. "You forgot to put your perfume on like I told you, and where is your pretty name pin? You said last night you really liked them. I expect you wear them both always." He did as she said. He could finally leave for work but he had a real sense of dread. On the way to work he wondered if he shouldn't just get a divorce. Finally he decided to try to hold off on any divorcing and try to convince Margaret to let him get back into his men's clothes. He was at work five minutes when he was called into Henry's office. Henry gave him a close look then smiled. "You look very sexy in that dress. I have some good news and some bad news for you. First, the bad news is that I can't have you wandering around in your dresses so I am taking you off of your job. Now the good news, I need a secretary so you can be my new secretary. You know computers and Margaret tells me you can type pretty fast, so you are now my secretary. Did she tell you she got you a raise yesterday? She is one hot woman in bed, I'll tell you that. There is one thing I have to see though. I want to see your small equipment." He was feeling no anger at Henry putting all the blame on Margaret. He was shocked that Henry would expect him to show him his equipment. He knew if he didn't show him, Henry would probably fire him. He got up and lifted his skirt and pulled down his panties. Henry laughed and said he hadn't seen one that small since grade school. All Toby could do is blush. Henry told him he could have the desk outside his office and that there was a woman's toilet down the hall. He was dismissed. He went out and sat at the desk. There was a piece of paper lying there with boot-up instructions for the computer. He booted it up and was surprised to see the company's logo and a well laid out menu on the opening screen. He saw they had the same office program he had on the computer at home. He sat there staring at the screen and wondering what he was supposed to do. The door opened and Henry handed him a tape. He found the machine to play the tape and soon was typing letters. He finished the third letter and was looking around the office. He saw the coffee maker and decided to make a pot. He went back to typing and was surprised when Henry Came out and said he smelled fresh coffee. Henry took a sip of his coffee and told Toby he was doing an excellent job. He handed Henry the three letters he had finished. He had to go to the toilet and headed there. He stepped inside and heard a woman crying in the stall. He was going to step back outside when the stall door opened. The woman was using a tissue to wipe her eyes. "Why are you crying?" The woman was sobbing yet and said between sobs, "I just broke up with my boyfriend; or rather he broke it off with me. We have been going together for over three years and were going to get married. I had to have a physical and they found out I could never have any children. His parents convinced him that he wanted children and he broke up with me." "Now, now, maybe it wasn't meant to be. I am sure a pretty woman like you can find someone who doesn't care that you can't have children. I know it looks like the end of the world but it isn't. There are worse things that can happen." He was holding her in his arms and she had her head on his shoulder. She got herself under control and was wiping her eyes. "You are so nice! Maybe we can go to lunch today? You make me feel so much better. What do you say?" He agreed. They arranged to meet in the hallway at noon. He went to the toilet and redid his lipstick and took a good look at himself. He didn't look half bad. At noon he met her. They went to a small restaurant and were eating their meal. The woman told him her name was Sarah and he told her he was Tammy. "Tammy, have you always been as caring as you were to me?" "I can't really say, you just struck a nerve or something. Maybe it is because my spouse is punishing me for something and I am in a state of turmoil." "Tell me about it, maybe I can help." He debated whether he should tell her or not. He realized she didn't know him and probably he would not see her again. So he decided to tell her everything. "Can't you tell I am really a man?" "No, not really. I have two girlfriends who have deep voices and there isn't anything else that tells me you are a man." "Well, I am and I am married. My wife says my manhood is too small and that I am more like a woman than a man. Last Saturday she got me into a dress and now she demands I wear dresses all the time. Sunday she had my boss over and she made love to him, telling me he was a real man. She says I am going to wear dresses for the foreseeable future. I think she is doing this to justify her unfaithfulness but I'm not sure. I am starting to like the feel of dresses sometimes, and that bothers me." "Don't let it bother you. You are a sweet man and I know you are a caring man. It isn't the size of his equipment or his clothes that make a man who he is; it's what's inside. You appear to care for your wife, or you would have been out of there and away as soon as she put you in a dress. After we met in the bathroom I thought about what you said, and I think you were right, that there is someone out there who is right for me. Your problem makes mine look pretty small right now." "Thank you for that. I think you're right. I just don't know what to do about it." "I think the easiest thing is to accept it and go with the flow. Show your wife she can do what she wants and that you don't care. Do what she says and maybe she'll relent." "Do you think she'll let me get back into my men's clothes then?" "I can't really say, but I think what you really need now is someone you can talk to so you can get over the humps." "I don't know anyone I can talk to. I've never made any real close friends and I never had anyone I felt relaxed telling my personal life to." "You just did with me. Try finding someone who understands what you are going through and talk to them." "You're right. I don't know exactly why I confided in you, it just seemed the right thing to do. Can I call you if I have to talk to someone?" Sarah agreed and gave him her home and cell phone number. She could tell he was a nice guy but that he had little backbone to stand up to his wife. She felt sorry for him. They finished their meal and headed back to work. Before they parted company she gave him a hug and a kiss on his cheek. He didn't know why but he walked back to the office as if he was walking on air. Back in the office he alternated between seeing Margaret and seeing Sarah in his mind. He thought about what Sarah had said, and could feel that she was right. He arrived home a completely different person than the one who had left. Margaret arrived home shortly after he did and found him fixing supper. He was humming a tune to himself, and she wondered what had happened to change him. At supper she asked how his day went. He told her about being made Henry's secretary and how Henry had told him he had gotten a raise. Margaret said she had gotten him the raise because when a man is being controlled by his sexual desires he would agree to anything. He didn't say a word about Sarah to her. He cleaned up the supper dishes and wiped the table, then was surprised when Margaret told him to clean the living room. He did as she asked without any comments. Margaret was busy somewhere else and he enjoyed the solitude. He did an excellent job of cleaning the living room. He was sitting relaxing and looking at the nice job he had done when Margaret came to inspect the room. She told him he'd done an excellent job. She told him to come by the dining room table that she had to talk to him. "As far as things lie right now you are not much of a husband here. You have become something else. I do not intend for you to lie around with nothing to do on evenings after work and on week-ends. So I've made a list of duties for you to do each day, and some to do once a week. Look at this and see if I missed anything. He looked at it and read- Monday-Clean living room good Tuesday- Clean my bedroom Wednesday-Clean kitchen completely Thursday-Clean bathrooms Friday-clean all other areas of the house not cleaned previously Saturday-Do laundry-wash and iron everything Sunday-clean all glass-doors and windows plus mow lawn Every day-Make up my bed and every third day change bed linens Cook all meals and clean up after He looked at it and wanted to laugh that she expected him to do all the housework. She would have nothing to do. "Well, what do you think of your list of duties?" "What is left for you to do?" "I will be busy being in charge. Did I miss anything you can think of?" "No, I can't think of anything. By the way we are almost out of coffee." "I did miss something. You can do all of the grocery shopping and you can also get whatever else I might need." "Are you going to have someone crown you queen?" "Very funny! I have an idea. You are going to be more of a maid around here than anything else. Maybe we should get you some maid's uniforms to wear. Then you will look right in place. What do you say to that?" "I don't think that is necessary. I don't need a maid's uniform." "I say you do. Tomorrow right after work we will go get you a sexy maid's outfit so you can look the part." She smiled triumphantly and watched as his face fell and he became very sad. She knew she was in total control of him. The next morning he drank one cup of coffee and headed out before Margaret was up. He got to his desk and started work. Then he remembered to make a pot of coffee. He was typing when Henry walked through saying good morning Tammy. Later he called Sarah and asked if she wanted to go for lunch. She agreed to meet him in the parking lot at noon. At noon he smiled as soon as he saw her. Soon they were seated and eating. He showed her the list of chores and told her about the resultant conversation with Margaret. Sarah couldn't believe Margaret was serious about getting him a maid's uniform. He said he believed she would just to show him she was in absolute charge. Sarah said she really felt sorry for him. She told him he was so nice and probably too gentle to turn Margaret down on anything. She told him she thought he should really think about whether their marriage was worth saving. She told him to think about what he had told her, that there was the right person for everyone out there, that maybe Margaret wasn't the right one for him. He had never thought about it from that standpoint. He did think how much he liked talking to Sarah. She was very pretty and she was a caring person as far as he could tell. They had the most enjoyable conversation he could ever remember having. Back at his desk he thought about all that had been said at lunch. He started to assess if their marriage was truly over. He hated to admit it but he was afraid it might be. Then he thought how Margaret had said she still had feelings for him. He remembered their early days of married life and the good times they'd had. He was in a quandary over what to do. He arrived home and didn't start supper just in case Margaret was serious about them going shopping right away. She pulled in and as soon as she was in she said it was time to go. He got into her car. She drove to Sandy's Uniform's and went in. Margaret spoke to the woman there for close to ten minutes then the woman took her to the two racks that held maid's uniforms. He stood by and didn't pay any attention to them. When he heard Margaret call Tammy, he went in to the two women. The woman was holding three uniforms in one hand and a full petticoat in the other. She led him toward the back of the store and into a small room. She told him to get his dress and slip off, which he did. She helped him get the petticoat on and then the uniform. He thought it was way too short but she told him it was a French maid's uniform and was supposed to be that way. She told him to go out so his wife could see him. He now knew Margaret had told her he was a man. "I don't suppose you get many men in here for maid's uniforms." "We get more than you would ever imagine. It is not uncommon at all." He stepped out and immediately heard Margaret laugh out loud. "You do look so sweet in that uniform. It looks like it was made especially for you. We'll take it." The lady said, "The way this one fits, the others will fit the same. Do you want them all?" "Yes, maybe he should have three black and also the pink one." "Do you want matching aprons for them?" "Yes, I think that would be nice." "Step over here and look at all the different styles we have." Margaret looked at all the different patterns and picked two that had black lace heart shaped pockets and one that had a little lace trimmed teddy bear pocket. Then she saw just the one for the pink uniform. It was pink with a lot of lace and a white lace trimmed rose for a pocket. Margaret said he could leave the uniform on, and then he wouldn't have to change when he got home. She made sure the lady heard that he could get right to work when they got home. He was glad to get out of there, and when Margaret turned the opposite way from going home he wondered where she was going next. She parked in front of Maggie's Specialty shoes and he wondered what was up. Margaret led him in and talked to the saleslady for about two minutes. Then the saleslady disappeared. He looked at some jeweled sandals and liked how they looked. He told Margaret he thought they looked nice, and she asked him if he wanted a pair. He said he didn't really care, he just thought they looked nice. Margaret said they would get him a pair. She grabbed a pair in his size. The saleslady came back with three shoeboxes and set them down on the floor. Margaret handed her the box with the sandals and told her to try them on him first. He walked around in them and they were very comfortable. He sat back down and the saleslady removed them then took a pair of heels out of the top box. He saw they were black patent leather. She slid them onto his feet and fastened the ankle strap, then told him to walk around to see how they felt. He stood up and just about fell over. He wasn't used to wearing five inch heels. He took very short steps and did manage to walk around a bit. He said they were very uncomfortable, but Margaret said he just had to get used to them. The next pair was pink patent leather and also had five inch heels. When he tried to walk in them he said he would never be able to. When she took the next pair out of the box he saw it was another pair of pink patent leather pumps with a wider ankle strap. She got them on him and when he stood up he could only shuffle his feet. It was as if he was walking on tip toe. The saleslady said that was common, walking in six-inch heels. Margaret told her to put the black ones back on him, that he would wear them home. He couldn't believe she was going to buy them and make him wear them. He carefully walked behind her and was shocked when she turned and led him into the store next door. She told the clerk she had placed a special order and they'd said it would be ready now. She gave the clerk her name. The clerk looked at some boxes under the counter and came up with two boxes. She opened one and showed it to her. Margaret said it was perfect. She paid the clerk and then took the box and removed the item. She told Tammy to stand still while she attached his pin. He looked down at it, and couldn't believe she would do something like this. The pin read 'Sissy male maid- Tammy'. He blushed the deepest he had since all of this had started. The letters of the pin were an inch high, decorated in false jewels and visible a good distance away. She led him back to the car. His legs were already getting sore from the new heel height. He felt a sense of relief being able to sit down. He wondered what was in the other box she had gotten. He knew it was nothing good for him. He was surprised when she pulled into a restaurant parking lot and parked the car. He said he wasn't hungry but she said he was either going to come in with her or start walking home. He went in with her. When the hostess was seating them Margaret told her she was treating her maid to supper. The hostess smiled and when she saw the pin on his chest she called him dearie. After they ate and got home she told him he better get started on her bedroom. He was glad to get out of her company. He didn't think he would be able to walk in these heels but did manage to make progress. He got her room done faster than he thought he would. She checked it and declared it to be all right. She told him to get his underwear out of his old dresser in her room. He got it and she told him to put the under shorts in the garbage, then instructed him to cut up the tee shirts for rags. He had tears in his eyes as he did it. By the time he finished he was tired and wanted to go to bed. Margaret had him get her a snack before he could go to bed. Then she wanted him to thank her for getting him all the nice pretty things. He didn't argue and just thanked her. He thought he would be able to leave but she told him to wait in the living room for her. She came back with a camera and started taking pictures of him. She told him how to pose and snapped a dozen pictures then got an idea. She told him to curtsy so she could get a picture of him. He tried but couldn't balance himself very well and it wasn't a good curtsy. She told him to keep trying until he got it right. He started to get cramps I his legs. Finally she said he was never going to get it unless he practiced, She told him she wanted him to curtsy every time he entered a room she was in and to curtsy before leaving her presence.. She told him he could go to bed. He went in his bedroom and the first thing he wanted to do was get the damn heels off. They were locked on his feet so he had to go back to Margaret to have her unlock them. She had a smirk on her face as she unlocked them. He wondered why she had to have pictures of him then thought she probably just did it to make him feel humiliated more. Finally, in bed he felt relieved. He noticed the softness of the nightgown and enjoyed the feel. He fell asleep immediately. He had a dream that woke him up in the middle of the night. He was fully awake remembering the dream. In it Sarah was wearing a wedding dress and when he looked, he was the groom. He smiled, and thought it wasn't possible. She would never marry someone like him. The next day at noon he told Sarah everything that had happened to him the evening before. She sympathized with him and told him he was way too easy, doing everything Margaret told him. She said Margaret was going out of her way to humiliate him. He told her he knew that, but now he wanted to see what she would do when she ran out of ideas of new ways to try to humiliate him. When they got back they were walking into the building and suddenly Sarah turned and gave him a hard hug then kissed him on his lips. He saw lightning bolts and felt a feeling he had never felt before. Sarah said she'd never kissed anyone wearing lipstick before but it wasn't bad at all. He wanted to grab her and return her kiss, but didn't do it. They agreed to meet for lunch tomorrow. That night he did the kitchen. He looked at the floor and saw it still was shiny, so he didn't scrub it. Margaret looked at it and said it looked very nice. Then she told him there were three empty boxes in garage and to get them. He got them and she told him to go into her bedroom and put all of his slacks and shirts in them so she could drop them off at the thrift shop. She had him put the boxes in her car and then he wanted to take a bath. She told him his curtsies were better and that she wanted to get a picture of him curtsying. After six curtsies she had two pictures of him curtsying. She unlocked his heels and soon he was enjoying a warm bath. The next day at noon he and Sarah discussed his options. He said he would make a solid decision this week-end. He said he thought Margaret was running out of ideas and he was looking forward to seeing her melt-down. Sarah told him he was too easy on her, that he should think about fighting back more. He told her he'd never done anything bad to Margaret and he wasn't about to start now. That night he cleaned the bathrooms. Margaret was busy and he was surprised to see her enter his bedroom. He wondered what she was going to do in there. He finished the bathrooms and was proud of how they were sparkling clean. Before he went to bed Margaret told him to change into a regular dress tomorrow after work, not the fancy ones he had been wearing. He wondered what she was going to do but dismissed anything fantastic. Friday noon he told Sarah he thought Margaret had run out of ideas about new ways to humiliate him. He told her Margaret hadn't taken any pictures of him at all last night. He told her he didn't know what he would do without her. She told him she still thought he was way too easy on Margaret, about not fighting her more. He reminded her he was going to make a decision this week-end one way or the other. He told her he'd never made any fast decisions and that he took pride in everything he done. He arrived home and decided to wear the yellow dress with his new jeweled sandals. When Margaret saw him she told him he looked so feminine in that outfit. She asked him to tell her he was more of a woman than a man and should be wearing dresses all the time. She told him he was going to tell her that sooner or later, so he might as well tell her now. He thought for a moment, then said the words she wanted to hear. She looked like she had just won a million dollars. She told him to sit down at the table that she had a surprise for him. He was surprised when she replaced the bottom studs in his ears with a pair of dangly earrings. He could hear the sound of a small wind chime they made every time he moved his head. Then she told him she had one more surprise for him. She replaced his Tammy name pin with a new one. This one read in inch high letters 'Sissy she-male Tammy'. She told him to grab his purse that they had to go. He got into the car with no idea where they were going. When she pulled onto the interstate he started wondering where they were going. An hour later she pulled off and drove like she knew exactly where they were going. She made several turns and soon pulled into a driveway. He had no idea where they were. She told him to come along, so he followed her up the sidewalk and to the door. When the door opened his heart sunk. He saw Joyce standing there smiling. He immediately knew this wasn't going to be good. They went inside and soon were sitting talking like old friends. He didn't say anything and after a little bit didn't really listen to Margaret and Joyce's conversation. He saw Margaret hand Joyce some pictures and then heard Joyce laugh out loud a few times. He knew they were the pictures of him. Then he heard Margaret calling him. He came back from his daydreaming. She handed him the car keys and told him to get the bags out of the trunk and the garment bags out of the back of the car. He had never noticed the garment bags in back. Joyce showed Margaret the bedroom where she would be sleeping. He was surprised when she said he would be sleeping in the basement. Margaret handed him a garment bag and told him to go change. He went into the bathroom and when he opened the garment bag he was shocked to see one of his black maid's uniforms there. She had even put the black heels he had to wear with it in there. He got it on and went back to the living room. Margaret chided him for not curtsying when he entered and made him curtsy to her and to Joyce. Margaret said she was sure Joyce had something for him to do. Joyce said he could scrub the kitchen floor. She showed him where everything was and before he started he had curtsied to her seven times. He did the floor and when it was done it looked better than when it was new. Joyce was impressed and told him so. She told him if he ever needed a job she would hire him. Margaret unlocked his heels and Joyce took him to the basement and showed him a small room where there was an air mattress and a small blanket. He got undressed and put on the nightgown Margaret had given him. The next morning he put the uniform back on. He was sure the women were going to have him doing something. He went upstairs and the two women were already up. Margaret told him to come with her and led him to her bedroom. She had him change into the green minidress and told him he could wear his jeweled sandals. He felt like singing until he got out where the two women were and Margaret pinned his name pin on him. Joyce chuckled when she saw him. Joyce said they could go shopping this morning but had to be back by early afternoon to get ready for the party tonight. Margaret handed him his purse and the next thing he knew they were shopping at the town mall. In a dress shop he saw a nice pretty dotted dress trimmed with satin bows. Margaret saw him looking at it and told him if he wanted it to get it. He was superbly happy until he heard Joyce laugh out loud. They returned back, and Margaret told him Joyce said the guests would be arriving in about an hour. She told him his party dress was lying on her bed. He went in and saw the red brocade dress lying there. He liked that dress and quickly had it on with its matching heels. It was tight on him but he didn't care. Joyce told him he looked like a beautiful pansy in it. Margaret told him to go put his name pin on, and that his perfume was on the dresser and to use a lot. He went and did as she said. When he came back out Dirk was there, having just gotten back from an out of town trip. Dirk said he smelled just like the fairy he was. The doorbell rang and it was Yvonne, who was Joyce's closest friend in high school. She introduced her husband and laughed out loud when she was introduced to Tammy who Joyce said she should remember from high school as Toby. She said she saw he was still in dresses. Over the next half hour some more guests arrived. They were all people who had known him in high school. Even Greta, who he had a crush on in high school, was there. He felt like crying it was so traumatic for him. Last to arrive was what Joyce said was a special guest. He just about fainted when he saw it was his mother. She said she'd always thought he liked wearing dresses more than he let on. She said he looked just like the wimp he was. He could have died, and it would have been a blessing. Joyce loudly said the server had just called and said she couldn't make it. He couldn't believe it when Margaret said he could be the server. She told him to come with her and when they were in her bedroom she produced his pink maid's uniform and told him to get it on. She knelt down and put his pink heels on him and locked the wide collar. He could hardly walk in the heels and couldn't believe what a difference a one inch higher heel could make. Everyone laughed when they saw him. His mother exclaimed for everyone to look at his fuck-me heels. Margaret told him he better start curtsying and keep curtsying. He curtsied and Joyce showed him all that had to be served. He was going steady for over an hour before they were done eating. Joyce told him to clean up the mess if he knew what was good for him and to get it done fast. He picked up the dishes and started to fill the dishwasher. He got it full and started. He piled the rest of the dirty dishes on the counter above the dishwasher. Joyce and Margaret came out and Joyce told him he could hand wash the remaining dishes. He turned and started the water running. Margaret told him he forgot to curtsy to Joyce. He shot her a quick curtsy. He finished the dishes and went and told Margaret he was ready to go to bed, that he was tired. He asked her to unlock his heels. Margaret asked Joyce if there was anything else she wanted him to do. Joyce said there were three trays of desserts to be distributed. He found himself walking around carrying a tray with little treats on them. When he got by his mother she asked him why she had never heard from him since the day he moved away. She asked why he hadn't even invited her to his wedding. He felt mean now so he told her he figured she hated him so he just let her stay where she was. He was surprised when she started crying. She told him she was sorry for all the hurt she had caused. He knew she meant it and felt bad about his remarks to her. Everyone else had derogatory remarks that they made to him. He felt he could have hurt every one of then and not felt bad about it. She saw Margaret showing Greta the pictures of him. He got all three trays emptied and asked Joyce if that was all. Joyce told him that was it and dismissed him. He had Margaret unlock his heels. He went down to the basement and even with the noise from up above was soon asleep. Upstairs it was getting interesting; Joyce was telling some of the guests how they came upon Toby last week-end and all about how she helped Margaret get him in a dress. She laughed as she told the story. Greta was listening, and as soon as Joyce finished her story she said, "I thought you'd grown up, but you are still mentally in high school. Do you realize you've probably ruined his life and his marriage? If I had known this party was to humiliate him then I wouldn't have come. You are still emotionally a teen-ager. I thought it was funny the first time in high school but after that I felt sorry for him. Where is he? I want to talk to him!" Joyce said he was in the basement. Greta said she probably had him locked in a cage or something. His mother, hearing the whole thing asked Joyce to go get him. Joyce said she would be right back with him. Downstairs she had a very hard time waking him. When she said some of the people upstairs wanted to talk to him he answered that he had heard enough bad comments for one night. He refused to go back upstairs. Finally Joyce left him to sleep. Upstairs she told them he was sleeping and all he wanted to do was sleep. His mother now said to the group, "My husband was a real mean man and I vowed my son would not be mean, I raised him to be gentle, as gentle and soft as I could make him. Now, I think I made a mistake. When you girls brought over those dresses I thought this was the perfect way to make him gentle, as gentle as a girl is supposed to be. I never thought it was to humiliate him as much as possible.