Karen's Story

Chapter One - In the Beginning

My name is Charles Ankersby. Well, at least it used to be, and this is the story of my life. It tells the tale of how I came to be Karen Miller. No, you're wrong. This isn't just another autobiography of a transsexual. I'm a transgenderist and, if you're not aware of it, that's a whole different thing.

It's an almost true story. It happened just the way I'm going to tell it to you. I have changed some names in order to assure anonymity for the other people involved. Later, if they're proud and want to brag, they can identify themselves, but I won't.

I suppose my Aunt Jeannie, my mother's younger sister, had a lot to do with the way I turned out. My parents died when I was young. Aunt Jeannie came to me after their funeral and said my parents had asked her to look after me if anything ever happened to them. She said she'd love to take care of me. Jeannie was twenty-four at that time, and one of the loveliest women I've ever seen. At five-foot four inches tall and weighing just over one hundred pounds, she was in wonderful shape. She had shoulder length dark auburn hair and green eyes that enthralled anyone who looked into them for more than a second.

I had always liked her a lot, probably because she'd always spoiled me so. She spent a lot of time at our house and was like a second mother to me. In some ways I had been closer to her than I was to my parents, so when she told me I'd be living with her, I was pleased.

It worked out well for both of us. Between the insurance settlement from my parents' estate and her alimony, Jeannie could afford to quit work and stay at home while she looked after me. That made it easier on her as she had always detested working for someone else.

A year or so after I'd moved in with her, she came home unexpectedly one day from shopping and caught me trying on some of her lingerie. I was panic stricken but thankfully she didn't make a big fuss about it.

All she said was, "Chuck, we're going to have to talk about why you like wearing my clothes. Please don't misunderstand me. I'm not angry with you. I don't mind it at all, but I think if wearing my clothing is important to you, it's something we must discuss."

I decided I had to be honest with her and trust her. There was no point in my denying it. I was standing right in front of her, wearing her pink full slip and panties, with a very obvious hard on. I felt completely ridiculous. There were tears rolling down my cheeks.

"I don't know why," I explained, "but I like the way your clothes look on me and the way they feel. I've been wearing your things for a couple of weeks, but I didn't want you to find out about it because I was afraid you'd laugh at me or punish me."

The look on her face told me she'd do neither. She took me in her arms and said softly, "I love you and I want to make you feel comfortable living here. So if it's important to you, then it's something I'll have to deal with. Please don't ever be afraid to tell me anything. I'll always try to understand and I promise I'll never laugh at anything you feel is important."

"Ok, Aunt Jeannie, I promise I'll tell you everything from now on. Thanks for not being angry. I love you so much," I said, and I meant it.

From that day on, when I'd come home from school, she'd be waiting for me at the door. We'd talk about my day and then she'd have me take a bath. When I got out of the tub, some of her lingerie and clothing would be on my bed, just waiting for me to put on. As she has a small build, almost everything of hers fit me or was slightly large.

I'd spend the rest of the afternoon with her, helping her get dinner ready or doing my homework. After a few months, I became very comfortable in her clothes. I even got so I could walk in heels without breaking my neck.

One day when I was older, Aunt Jeannie told me it was about time that I stopped dressing in her things. For a moment I was very afraid, thinking she wanted me to stop wearing her clothes, but that wasn't it at all.

"After all," she said, "you're not a child anymore. You're at the age where little girls become big girls. I think we should spend this weekend changing you into a young lady. Would you like that?"

"Oh, yes," I exclaimed. I was excited, but a little embarrassed by my enthusiasm. But, as usual, she always seemed to know exactly what was on my mind. "I've been thinking about that a lot lately and I'd really like it. Some of the girls in school have begun to develop and I guess I'm jealous. How can I be a woman, though? I know I'll never grow boobs."

She smiled at my embarrassment. "That's probably true, but there are ways to make up for what nature hasn't provided. Women have been doing it for centuries. I'll make you beautiful, you'll see. Just trust your Aunt Jeannie. She knows what she's talking about."

"Oh, I hope so. I'd love to look as pretty as you do, or like some of the other girls at school. I see the boys staring at their chests as they walk down the hall. It's very confusing for me. When I look at them I feel turned on but envious too. Maybe it's because even though I like girls, I guess I want to be one too."

Aunt Jeannie gave me a very surprised look. "That's the first time I've heard you say you wanted to be a girl. When did you decide that?"

"I don't know. I guess maybe I've always felt that way. Spending a lot of time in your clothes has made me realize I'm much more comfortable as a girl. I guess I'd have been happier if I'd been born that way. Does that make me weird or something?"

"Believe me, you're not weird. There are a lot of people in this world who feel exactly as you do. Many of them eventually end up having operations that change their sex to the one they feel they should have been born as. It's becoming more and more common all the time. So don't think you're a freak. You're definitely not.

"But enough talking," she said. "Let's see what you're going to look like as a young lady. Go hop in the shower. Make sure you shave your legs and underarms well. We want you looking your best today." She gave me a pat on the rump to speed me on my way.

I felt a lot better knowing I wasn't alone in the world. I didn't want to be a freak. I quickly undressed and got into the shower. I couldn't wait to see how I'd look as a mature woman. I shaved my legs and underarms, making sure that not even the smallest hair remained. It didn't take long as I've never been very hairy. After drying off, I softened my legs with a moisturizing lotion, then covered my whole body with perfumed dusting powder, just Jeannie had taught me to do.

She was waiting for me in her bedroom sitting on the edge of the bed. She checked me over to be sure I'd shaved well. "I want you to wear the things I choose for you, but just for today. That way I can be sure you look as good as possible the first time you see yourself as a young woman. From then on, you can wear whatever you like. All right with you?"

"Sure, that's fine with me," I answered. I was so happy that she was going to let me get dressed up as adult that I didn't care what she'd selected. Besides, I knew she had great taste in clothes, so whatever she picked out for me would look good.

First, she had me put on one of her pretty pink uplift bras, and then insert some foam rubber falsies she told me she'd bought just for today. With the falsies in, I felt as if I were complete for the first time. So feminine! But when I put on the matching pair of pink panties, my erection made the whole thing seem silly.

Jeannie was determined she was going to do something about that problem. She knelt down in front of me and caressed my penis through the soft fabric of the panties. Just before I was ready to come, she took it out and sucked it between her lips. I lasted about three seconds before I gushed into her mouth. To both our surprises, my erection didn't disappear. She had to do it again before I finally went limp.

But even after all that, the bulge in my panties was still considerable. We tried several different things to conceal it, but nothing seemed to hide this very unfeminine protrusion. Finally, after several other methods failed, much to my embarrassment she tried a sanitary belt and napkin. The belt was made of elastic, about an inch wide. She slipped it around my waist and then attached the sanitary pad to the two hooks that dangled from the belt. She tucked my balls and penis back and with the sanitary pad pulled very tightly, it turned out to be the perfect answer. I put the wispy panties on again and this time they looked like they were made for me. Not a bulge in sight!

"Oh, Aunt Jeannie," I said, "I can't believe how well it works. By the time I get on all my clothes, there won't be any sign of it at all."

Jeannie and I decided that, as we were going to dress me as a young woman, not a girl as we had in the past, a pink garter belt and stockings would be fun for me to wear. She showed me how to put the garter belt around my waist and then helped me put on the sheer stockings. I was amazed at how pretty my legs looked and the feeling of the stockings on my legs was wonderful! If it hadn't been that my cock was so tightly compressed by the sanitary napkin, my erection would have caused another unsightly bulge.

Next, she handed me a pink slip that had a wide band of lace at the top and hem. Jeannie had learned early on that pink was my favorite color for lingerie and just about anything else. I wriggled into the lovely slip, adjusting the straps to fit. The smell of my perfumed dusting powder, combined with the soft, silky caress of all this pretty lingerie, was making me feel very feminine. It seemed so very natural for me to feel that way.

She picked out a pair of black patent leather shoes with three-inch heels for me to try on. They fit perfectly, but when I tried to walk across the bedroom, I nearly broke my neck. Jeannie laughed and said she knew I'd get used to wearing higher heels very quickly.

We completed my outfit with an off-white blouse and a short pleated plaid skirt. The skirt was a bit loose on me around the hips, but she told me not to worry. She would be able to make minor adjustments to many of her pretty things so that I could wear them.

All this time I was becoming more excited, thrilled really. I was somewhat nervous, yet pleased at each step as we continued my conversion into a young woman.

She tried several wigs on me, but all the styles seemed too adult. In the end, as my hair was rather long, Aunt Jeannie used her curling iron and did my hair in a very pleasing feminine style.

We went through the whole business about makeup and jewelry. She said I'd have to learn to do this myself in the future so she'd explain each step as she went along. Putting makeup on properly, she told me, was an art. Too much makeup made you look cheap, and not enough made you look plain and unhealthy. Jeannie was an expert. By the time she was finished, I looked exactly like a very pretty young girl.

My reflection in the mirror was stunning, especially to me. I had never imagined I could look as nice as I did. The makeup, the foam rubber breast pads and the grownup clothes made all the difference.

We left the bedroom went into the living room as Jeannie wanted to show me a few more things about being a lady. She led me to a chair and said, "I'm sure you don't want to look all wrinkled, so when you sit down, make sure your skirt isn't all bunched up in back. You have to be conscious of how you sit as well. A lady either crosses her legs or keeps them together. Try it and see how you do."

I had been watching women and the way they do things for quite a while, so it was very easy for me to slip into their role. I smoothed my skirt out in back and then slipped onto the chair. As I experimented with crossing my legs, I was enthralled with how sexy my stocking clad legs looked peeking out from under my skirt. I loved their silky feeling.

When I got up, she hugged me and said, "You seem to be a natural at being a woman and you look much more like a pretty girl than I'd ever hoped for. So much so, that we'll have to pick out a name that's more suitable for the new you. Calling you Chuck would seem silly now."

"How about Karen?" I suggested. "I know a girl at school by that name, and I like it a lot. I'd like to use Anne as a middle name." She knew why. It had been my mother's name and I still missed her very much.

"That's a great idea. We'll start calling you Karen right away. I know your mother would be pleased. If she were here today, I think she'd be as supportive of your need to be feminine as I am. I'm very proud of you, honey. I've just got to show off my pretty niece. We've gone to too much trouble today to just sit around the house without anyone seeing how lovely you've turned out. Let's go shopping at Northland mall. That's perfect. Then we can buy you some pretty clothes of your own."

I looked at her like she had suddenly gone crazy. "You've got to be kidding! I can't do that! People would point at me and laugh," I complained.

"Honey, they'll not only believe you're a girl, but I'm sure once the boys see you, they won't leave you alone. Come to think of it, that might prove to be a problem. How will you feel if men pay attention to you? Are you going to like it or will it make you nervous?"

"I've thought it once in a while, but I'm not sure how I'll react. I've had some dreams about meeting a man, but I'm not sure how I'd feel if it actually happened. Do you think it means I'm gay?"

"No, probably not. Most people have similar fantasies. You might be bisexual, but judging from the way you reacted earlier, I'm sure you're not a homosexual. Bisexuality is becoming very prevalent these days. I found out a few years ago that I'm bisexual and so are some of my friends. So even if you are, don't worry about it. It just means all the people in the world are your potential lovers, not just half of them. What's so terrible about that?" I knew I was blushing, but I couldn't help it. Sex wasn't something I'd ever discussed with anyone before.

"I guess that makes sense," I said. "I've never thought about it that way. I know women have always turned me on, but I think I fought any attraction I felt for men because all my friends hate gays so. I didn't want them to think I was one."

"Most children act that way because they don't understand gays. As they grow older and get to know some gay people, they realize they're not very different than anyone else."

I had to admit it was comforting to know I wasn't as strange as I'd thought I was. She took my arm and told me, "You and I are going to go shopping now, Karen. We're going to buy you some pretty things of your own. How would you like that?"

"I'd like it a lot but I'll be scared to death," I admitted. "Are you sure no one would be able to tell I'm not really a girl? I'd die if anyone found out."

She gave me a reassuring look. "No one will be able to tell you're not a girl because, in my opinion, you really are a girl. You think like a girl, you act like a girl and now you even look like a girl. You look more natural now than you ever did as a boy. So don't even give it a second thought. Don't you feel as if this is the real you? I'll bet you're a lot more comfortable with yourself now."

"I guess I do, but I'm so nervous about going out in public in a skirt. Won't people who know me be able to tell it's me? You know how the other kids in school would treat me if they ever found out about this. I'd never be able to go back there again."

Well, the flattery eventually worked and I reluctantly agreed to go. Jeannie spent a few more minutes putting the finishing touches on me.

"Here," she said, "you can carry this handbag. Let's put some makeup, a brush and this wallet in it. Oh, and here's a watch for you to wear as well. What about a necklace? Would you like to wear one with that outfit?"

I knew just which one I wanted to wear. "Could I wear the pretty braided gold chain you got in New York last year? I promise I'll be extra careful with it. I've always wanted to see how it would look on me."

"Sure, it's in my jewelry box. Help yourself. Here, put this money in your wallet. We'll have to get you some identification with your new name on it eventually. There are so many fun things we'll be able to do now... just us two girls."

We both had a good laugh at that. Her reassurances had calmed my nerves and I was beginning to enjoy myself. I knew she was right, but I guess I couldn't help fearing discovery by someone I knew.

After a final check in the mirror, we left for the mall. I was still very nervous. It was a new experience for me to be outside as a girl and, as we approached the mall, I was tempted to ask Aunt Jeannie to turn around and take me home, but the thrill of being out as a girl outweighed my fear in the end.

As we got out of the car I felt as if everyone was staring at me. I told Jeannie, but she said it was because I was so pretty, not because they thought I wasn't a female. She said it's something every pretty girl has to get used to.

"There are so many things I want to buy for you, Karen," she told me. "I think you should have some pretty things that will be your very own, like shoes and lingerie and so many other things. Not that I mind you wearing mine, but I think every girl should have her own very special feminine things. You'll see. I know you'll love being a young woman as much as I did when I was your age. It's so much more fun than being a boy."

"You're right," I conceded. "It is fun. I feel so strange, but it's a good feeling." I felt like I was in a different world. I was so much more aware of everything around me. I kept up a non-stop conversation, talking about everything that popped into my head.

As we were approaching the mall, Jeannie stopped me and said, "Karen, you've been getting dressed as a girl at home for a long time. I've been watching you. You behave perfectly as a girl when you're wearing a dress. As the saying goes, you've come a long way, baby. So stop worrying. I guarantee you no one will know the difference."

Walking through the mall, it pleased me to notice that we were getting many admiring glances from men. Jeannie noticed it too and asked me what my reaction was. I had to admit I loved it. Almost immediately I became more relaxed and began to enjoy the feeling of being a woman. It was fantastic! I loved how my skirt caressed my legs as I walked, and the clicking of my heels sent chills up and down my spine.

Maybe it was the novelty of the situation or the fact I also felt more grown up as well. I didn't know why for certain, but I truly loved being a girl. So many men stared at me and I could see desire in their eyes, and that thrilled me sexually. It really did.

Jeannie and I had a great time shopping for my new wardrobe and trying on clothes. We went into almost every store in the mall. I spent at least a half hour trying on lingerie at one of the better department stores. I didn't even get too nervous when one of the saleswomen walked in on me. All I had on was my bra and panties. She clearly didn't think of me as a boy. Luckily, my sanitary napkin hid the bulge in my panties perfectly. She just handed me a nightie to try on and then walked out.

We stopped at Jeannie's favorite shoe store and she bought me four pairs of shoes there. There was a particularly cute young salesman in the store who waited on me. He became friendly very quickly. I was amazed when I discovered that he was trying to look under my skirt each time he helped me try on a pair of shoes. That made me very nervous, but I knew I was also flattered. I did purposely cross my legs a few times and I'm sure he liked what he saw. I had to choke back a laugh. Wouldn't he be shocked if he knew what was really inside those lacy pink panties he was sneaking a look at! I must admit I even flirted a bit with him. Aunt Jeannie watched all this, trying to hide her laughter. While she was paying for the shoes we'd bought, he asked me for my phone number. I was tempted to give it to him, but I knew I couldn't.