February 3, 2003

 

Cindy Anderson

a story by Carol Clark

 

Allison Anderson looked out through her kitchen window as she rinsed a few dishes and put them in the dishwasher. It was a bright Saturday morning. Her husband Ralph had left early for his tee-time with his buddies. Ralph and Allison's daughters, Sally, who was in her final year of high school, and Janet, who was a freshman, were at sleepovers. This was the perfect time for Allison to have a talk with her son Billy.

As Allison heard Billy come down the stairway, she called to him. "Billy, I would like to talk with you," said his mother, in a tone of voice she reserved for serious matters. "Come with me to the kitchen."

Billy followed his mother's voice to the kitchen, where she poured herself a cup of coffee, sat at the table, took a sip, then looked over Billy's face as he sat down with his hands folded on the table.

"Billy, I need to talk with you. I have chosen this time because your father is out golfing, and your sisters are both on sleepovers. I need to ask you a question, so I will just ask: Why have you been taking clothes from your sisters' rooms and hiding them in your room?"

Billy sat quietly. He could only wonder if his facial expression was giving him away. He calmly replied, "Mom, what do you mean?"

"Billy, I know this may be difficult for you, and maybe you would rather not talk about it now, but if there is something you would like to discuss with me, please tell me. I would rather know the truth."

"What do you want to know?" he asked.

"Well, let's start with this suitcase," pointing to one of her suitcases on the floor against the counter across the room. "When I was putting clothes in your closet, I wondered why my suitcase was in there. I opened it and found two complete outfits of your sister's clothes, plus a pair of Sally's shoes. I asked her about it, she was as puzzled as I am."

Billy waited a moment, looked briefly into his mother's eyes, then looked down to his folded hands. "Mom, . . . I don't want to be untruthful with you. But also I feel uncomfortable telling you. The truth is, I put those clothes in the suitcase. I tried to choose things that Sally would not notice were missing. I did not want to use any of her favorite things. I like to dress as a girl. I don't know why. I have always been this way but did not want to tell anyone. I feared you would not understand. Even I do not understand. Why would a guy want to be a sissy and dress as a girl? I don't have an explanation for it, but dressing as a girl is something I like to do."

Allison sat speechless. She had a feeling that Billy might say this. Although he was an outgoing "boyish" boy, he had never been a "rough-and-tumble" sort of boy.

"Billy, being your mother has been a joy for me. You have always been the perfect child. But this is something about you I never suspected. Aren't you happy as a boy? Do you wish that you were a girl?"

"Mom, I really do enjoy my life as a boy. And I don't know if being a girl would be what I want. But I do enjoy dressing as a girl. And thinking about how different my life would be if I were a girl. I have tried not to feel this way but the feeling always comes back. When I see a pretty girl, like Sally or Janet, wearing a pretty dress, I just feel like that is what I want to do too."

"Well, then. When did you last see either one of them in a dress?" said Allison with a chuckle. I haven't seen them in a dress or skirt in some time now! But let's talk about you. When did these girlish feelings start? Have you ever talked with Sally or Janet about this? With anyone? You're in eighth grade now. When do you dress up?"

"Wait a minute, mom! One question at a time?"

"Sure, then. Why don't you just explain to me how this all started. Tell me about when you first started to know that you liked to wear girl's clothes."

"Thanks, mom. I'm glad we are talking about this. I had been afraid to bring up the subject before, but there had been so many times that I wanted to ask you or Janet about this. I feel more comfortable talking with Janet about things than with Sally. But I was always too shy to ask even Janet if I could . . . You know that Janet has a closet full of cute dresses but she hardly ever wears them; she prefers to wear jeans and a tee shirt and sneakers. What would she think about her brother, a boy like me, wanting to wear her clothes? But I could not wear dresses without being laughed at.

"Come on now, Billy; you're doing fine; Relax and continue, said Allison with a reassuring smile.

"OK, mom. I'm really nervous. Ever since I was little, I enjoyed seeing Sally and Janet in their pretty dresses. I always wanted to be able to wear dresses too, but I was afraid of what people would say or think of me. Sometimes I would sneak a few of their things into my room and quickly try them on. I was always afraid I would be caught. I would put on panties and a slip, a dress, shoes and socks, and enjoy the feeling of being dressed as a girl. I never kept the stuff too long, and I was always careful to put things back where I found them. Then I started keeping things in the suitcase. I usually dressed after everyone had gone to bed. There were a couple of times when I had to dash into bed, dressed as a girl, and pull the covers up to my neck when I heard you coming!"

"I'm sorry this has been so hard for you," said Allison, "It must be difficult to keep these feelings to yourself. And I know that you might feel like a sissy for doing these things. "But," she said with another smile, "It would be fun to have three daughters, if only for some of the time!"

"Janet and Sally will be coming home about noon today. Would you like me to tell them about this? I could ask them to dress you up, maybe they would enjoy helping you to be like a girl? Or maybe you would want me to dress you up now? How about if you go upstairs and take a shower, then I could start to fix you up really pretty."

Billy was a bit uneasy. "I don't know, mom. I'm not sure if I am ready for anyone to see me as a girl. It was such a surprise for you to bring this up. Maybe another time?

Mom replied: "I sort of had a feeling you would say that. But now that you have confirmed it was you who put those things in the suitcase, don't you think it is just a matter of time before you follow through on your desire to get dressed all the way? Let's do it. You are going to be my third daughter today!"

Nearly two hours later, Billy was standing in front of the full-length mirror in his mother's bedroom. Allison was standing behind him, her hands rested on his shoulders as she turned him side to side so he could see how he looked from different angles.

"Billy is not a name for a girl like you," said Allison, "And even Billie is too much like your old name. I will call you Cindy, which is the name I had picked out when I was pregnant with you, if you were a girl.

"Cindy" admired herself in the mirror. She was wearing Sally's Easter dress from a couple years ago. Knee-length taffeta with a wide coral sash and short puffy sleeves. The buttons in the back were all fastened, something she could not do when she had tried on dresses before without help. Wearing a dress with back-buttons meant he would need help to be released from wearing it.

Allison beamed; "Are you pleased, Cindy dear? Isn't this about what you wanted? It is not surprising that a boy your age, just 12 and still without all your masculine features, would look quite convincing as a girl. I can't wait until Janet and Sally get home and see you like this!"

"Do they have to see me in a dress? Can't we keep this our secret?"

"Why? Don't you want your sisters to know how much you like to be like them? And I'm sure they would be willing to share some of their clothes with you and teach you some little things about being a girl. I plan to ask each of them to go through their closets and find things you could wear. They probably have things they would not want to have you wear. You will not have to hide or sneak around anymore. Cindy will have her own clothes, and I will have three daughters!

Mom made me stay dressed as Cindy until Sally and Janet came home. Luckily, each of them came home without any friends with them. I could just imagine how it would be if Sally's best friend, Jennifer, saw me this way. How could I have such a cute girl see me like this. Or maybe it would be neat having her see me as a girl. Maybe another time.

Cindy spent the morning with her mother. Allison seemed amused at first, but after a while she seemed quite at ease having her new daughter around. Allison polished Cindy's fingernails and applied new makeup to her face. "This is more makeup that I let your sisters wear when they were your age, but this is a special occasion," said Allison as she finished touching up Cindy's mascara, blush, and lipstick.

The morning went by quickly, It did not seem that long before Janet walked through the front door, and called out, "Mom, I'm home!"

As Janet was coming in the house, I was in my bedroom. I had seen her boyfriend's mother's car drive away as I had looked out the living room window. I hurried upstairs to my room. Mom told me she would break the news to each of the girls rather than suddenly having them see me as Cindy.

"Hello, Janet, how was your sleepover?" asked Allison.

"Great, mom, but we hardly got any sleep. I will probably need a nap this afternoon. Is there any of that pie left?" Janet gave her mother a quick hug, then continued to the kitchen.

"Janet, could we talk?" asked Allison.

"Sure, mom, is there something wrong?" replied Janet as she looked into her mother's eyes.

"No, dear. But there is something I need to tell you. Did you ever talk with your brother about his desire to dress as a girl?"

"What? Billy? Is this a joke? What's happening?"

"There is no easy way to break this to you, I guess, but Billy told me he likes to dress up as a girl. This morning, I helped him dress up. He is upstairs in his room, dressed as "Cindy," a name I gave him to use while he is pretending to be a girl today."

"You're serious? Really, mom! A girl? He wants to be a girl?"

"Well, maybe not to be a girl, but to dress as one and see how it feels to be dressed up as a girl. I told him to stay dressed up until you and Sally got home to see him. But you don't have to see him dressed this way if you really don't want to."

Janet pondered the matter for a few seconds, then said, "Sure. A little girl, huh. My brother wants to be a girl. Well then, let's take a look. I'd like to see him in a dress. My dress? Is he in one of my dresses?"

"I was careful to choose things you would probably not mind him wearing. He is wearing a very feminine party dress, actually it is one of Sally's Easter dresses. Let me go get her. Cindy, I mean."

Janet waited downstairs as Allison went up to Billy's room.

"Cindy, dear, your sister wants to see you. She promised to be open-minded about this and to try and understand how you feel. Now grab your purse and follow me down stairs."

Cindy stood up, looked briefly at herself in the mirror, then followed her mother.

Janet stood silently as she watched her mother walk down the stairs, followed by a young-looking girl. This was Billy? Janet was taken aback by how much Billy looked like a girl.

"So you're Cindy, huh. Mom told me about this. You want to try being a girl? Well, you do look like a girl. I'm surprised how much you do look like a girl. I wouldn't have recognized you as Billy. But, why now? Have you always been like this?"

Cindy was feeling less uncomfortable than she thought she would be. Here was one of her older sisters, seeing her dressed as a girl, and seemingly not surprised.

"Mom, how long is Cindy staying with us? She should at least stay for dinner!" said Janet.

"Actually, maybe for the weekend?" replied Allison. Twenty four hours or more as a girl will help her gain a better understanding of what girls do. Arising in the morning as a girl, spending the day as a girl, doing the things her sisters do, I think she will gain a really good experience this weekend as a girl. Have you any advice for your new sister?"

"Yea. Keep your legs crossed and your knees together! You know that the boys will be looking over a cute girl like you. Have you considered how you would handle having a boy look you over with that knowing look? You know what boys want from a girl!"

"That's enough of that, Janet!" said Allison. "Cindy is a sweet girl and there are things she will need to know. But you're right. I think boys would find Cindy attractive.

"Janet, why don't you take Cindy up to your room and show her around?"

"Sure, mom. Cindy, this way!"

Janet bounded up the stairway, quickly as she usually did. It was easier for Janet, since she was in sneakers, jeans and a tee shirt, while Cindy was wearing a dress and pretty shoes.

As Janet entered her bedroom, she jumped up on her bed and turned around to see Cindy demurely walking into the room.

"Don't you feel like a sissy, Billy? I mean, why would a boy want to dress like a girl? Boys never have to look pretty, they don't have to worry much about how they look. Why don't you tell me a bit about all of this, "Cindy!"

As Cindy began to talk, Janet was looking her over, wondering how her brother really felt dressed up in girl's clothes.

"Did mom make you wear everything? Panties? I can see that you're wearing nylons or pantyhose, and probably a slip too! How do you think you'll get out of that dress? One of us will have to unbutton you or else. Maybe that's what you want, to be stuck wearing a dress? You didn't answer my question, don't you feel like a sissy?"

"Janet, this is serious for me. I don't mind if you are amused by this, but I really wanted to try doing this. I know I could not really be a girl, but the thought of dressing this way has always appealed to me. I have always wanted to dress as a girl, and now I have the chance. Maybe I am a "Sissy," but this is what I want to do.

"Well, now, little girl. How far do you plan to go with this? Do you want mom to let you play little-girl dress-up all the time? Shall I look forward to having you dress up as my sister all the time now?"

Cindy explained how the morning had been spent, with Allison dressing her in several outfits and taking video of everything.

"You mean you let her video everything? Wait til this gets around. My brother my sister! Let's take a look at the video!"

"Wait, now, Janet. Can't we just talk first?"

"Sure. What do you want to talk about?"

"Well, first, what do you think? Are you surprised? Can you tell me how you feel?"

"I come home and my brother is wearing a dress. Everything. From panties to girl's shoes, wig and makeup to a pretty dress. Not what a sister would expect from her brother. How do you think I feel?"

"Are you offended? "

"Not offended. Surprised, maybe. Puzzled, yes. A boy wanting to dress like a girl. I guess it happens but I had never thought it would be my brother who likes to do this. Give me some time to think about it. I'll let you know!"

"Mom said she was going to keep you in that dres until Sally gets home. But mom asked if I would pick out some things from my closet for you to wear. Let's take a look."

Janet went to her bedroom closet and moved clothes down the rack with her hands, moving things around and pulling some clothes out and on the bed. "You can wear most any of the dresses that fit you. You probably have noticed that dresses are not my thing now. Its funny that a boy would want to wear dresses, and girls want to wear pants!"

Janet picked up a dress from the bed and held it in front of Cindy. "You would be such a sweet girl wearing this. With the right hair, shoes, and everything, of course. Do you think about dating boys when you are a girl? Is that something you want to do?"

"Janet, I am still attracted to girls, not boys. I am not interested in dating boys. But I like to pretend I am a girl doing girl things, so dating a guy is something girls would do, but maybe not this girl.

"What will dad think!" said Janet in an excited yet cautious voice. "Are you going to let him see you this way?"

"We haven't gotten that far. Mom did not say. I don't know."

"Boy, will he really be surprised to find his only son wants to be a girl! A sissy girl at that!"

Janet could see that her joking around was not going over well with Cindy. "Oh, Cindy dear, did I offend you?" said Janet in a mocking, teasing manner. "But, a little girl has to know about so many things. And be ready for surprises!"

"Janet, the phone!" called Allison from downstairs.

"I'll take it down there" said Janet as she raced down the stairs.

Cindy remained in Janet's room. Here she was, dressed as a girl, in a girl's room. She pulled out a few drawers and found an assortment of panties, bras, so many feminine things. Even girls wearing pants had pretty things on underneath. Cindy looked into the mirror at Janet's dresser and pretended to primp, making faces at herself as she pouted her lips, arched her eyebrows, turned her head side to side.

"Just like a girl, alright, its true, you are like a girl!"

Cindy turned around to find Sally standing there. Worse yet, her friend Denise was with her.

"I didn't hear you come home!" stammered Cindy as she looked at Sally and then glanced over to Denise.

"Mom told me the whole story. I hope you don't mind that Denise is here. She had told me before how she liked the idea of making boys dress as girls so I knew she would love to see you this way. You really do look pretty, doesn't she, Denice?" said Sally as she turned to Denise.

Denise walked over to Cindy. "I think that boys should have to do this to give them a "feel" for what girls have to do. It would be good for boys to be dressed up like girls, to wear dresses, makeup, high heels, and be treated like girls. Don't you think so, Cindy?! Tell me that you want to be treated like a girl. I'd be happy to help Sally treat you like a girl. This will be such fun!

 

Allison served lunch to the girls. The dining room had a complement of girls, but only Cindy was wearing a dress. The topics were all aspects of how they would show Cindy how to be a girl.

"Did anyone explain to her about her period?" asked Denise with a slight snicker. Girls her age are just getting their periods so she should know what to expect."

"That's right, dear, said Allison with a smile, all the other girls here have their period, so we will have to show you how to have yours!"

"You're turning beet red, Cindy!" said Janet, pointing to Cindy. "Even through your makeup! Gee, mom, he gets to wear more makeup than you let me wear!"

"Easy now, Janet, Cindy is a special girl so we have to treat her a little differently than I did with you and Sally. Just think, if we had known about Cindy when she was little, she could have been wearing little-girl dresses along with you two!"

"What do you think, Cindy," said Sally with a laugh, "Would you have wanted to wear little girl dresses when you were little? And mary-jane shoes and lacy white socks? I'd think you would have made a pretty little girl!"

"Why don't you girls take Cindy upstairs and get her changed? I need to go to the mall this afternoon and there's no reason she can't go with us. But in an Easter dress? Why don't you pick her out something feminine, yet something that would blend in with the crowd!"

Cindy felt a little bit embarrassed standing in Sally's room, wearing only a slip, as the girls decided what she would wear.

"He, I mean she, should not get to wear pants, she needs to wear at least a skirt, said Sally.

"And a blouse, not a tee-shirt, said Denise.

"And it should be sheer enough to show off her bra! added Janet.

The girls then burst into a big giggle.

"Sorry, Cindy," said Sally, "But don't you know this is as much fun for us as it is for you? Maybe not fun for you, maybe a bit scary for you, going out in public the first time as a girl. This is your first time, isn't it?"

"Yes," replied Cindy firmly, "I've never been outside the house as a girl."

"Well, that is all about to change," said Sally as she held up a long-sleeve white blouse and a grey jumper. "This will make you feel feminine, the blouse buttons up the back!"

Cindy held her knees together in the middle of the back seat of Allison's car as Sally drove away. Mother was in the front passenger seat and Denise and Janet were sitting beside her in the back seat of their full-size Buick.

"Don't worry about a thing!" said Denise as she gently squeezed Cindy's nylon-clad knee. "Just remember, you are a pretty girl, and that's how people will see you."

Cindy felt the blouse buttons pressing slightly into her back as she rested in the back seat. The hemline of her jumper was just above her knees. Her polished fingernails held her purse tightly in her lap. She was experiencing her dream, going out as a girl with her mother and three other girls showing her the way.

- end -

 

 

 

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© 2003 by Carol Clark. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.