Karen's Story
Keywords: Story, Karen's,
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*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.
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Keywords: Story, Karen's,