My name is James and I've always considered myself a ladies man. I grew up in a house of women, my father died when I was small and my beautiful mom became so involved with supporting her twin daughters and baby son that she didn't remarry until she became an empty nester. I was the baby of my family. And being the only boy, I had a devoted mom and loving sisters. They all doted over me as if I were a prince. My sisters, Susan and Sarah were not identical twins, but each was beautiful and each grew to be brilliant, capable, and strong women. Having been shown so much love and affection from those three, I grew up to be the type of man that women adored. Knowing how much my mom struggled for us caused me to develope a deep appreciation for women. I took it for granted that a woman could do or be anything and I saw how some men relished trying to dominate them and I simply couldn't. I liked them too much. I became the husband who all the other wive's adored. On Superbowl Sunday, we'd go to parties and I'd hang in the kitchen with the women. That was always more interesting.
I looked more like my father and never had the fine lines beautiful features that the girls had, but still women considered me desirable. I knew how to treat them in a loving supportive fashion and I found I could have any woman I wanted. Eventually I met my wife who is also a strong beautiful woman: a perfect match for me. We have a great marriage, two fabulous daughters, and recently she pulled out a photograph that my mom had taken of me which I had to explain and for once, I found myself tounge tied.
My sisters were four years older than I was. Both girls were extremely popular and always had boyfriends. However, they both liked to avoid too much committment and always had new guys coming to our house. In the spring of their senior year of high school, for once, Sarah had a steady boyfriend. His name was Tim and he made it known that all of his friends were envious of him because he dated Sarah. He'd often ask Sarah if she'd fix up one of his friends with Susan. Both my sisters hardly needed anyone to arrange a date for either of them, but Sarah finally talked Susan into accepting a date from Tim's cousin who lived in the next community. His name was Scott and Susan agreed to let him take her to a movie and dinner one Saturday night
When that day arrived, I had just returned from a soccer game. I was in eigth grade. I was a tall lanky thirteen year old. I was in that awkward stage of not quite a little boy, but not quite a big boy. I was too tall and my face was too soft and my voice was too high, and my feet were too big. Today, we call those kids tweens. I had no plans that night except to finish a science fair project. I assumed the girls would both be out and mom usually got together with some girlfriends on Saturday evenings, but as I entered our kitchen I heard Susan shout, "Mom, he's home." Mom called out good and Susan just grinned at me. Sarah practically ran into the kitchen and breathlessly greeted me.
Something was up, but I couldn't imagine what. Mom entered the kitchen and before anyone spoke, the three of them began to giggle. "Did I miss something," I asked.
"No dear," mom replied, "but the girls and I were talking about Susan's date tonight.."
Sarah interupted, "and Tim's cousin is worried that Susan won't be as... well, as "FOXY" as I am." They all burst out laughing.
Susan jumped in, "when Scott found out we were not identical twins, he thought that I might be the dog of the family."
"And mom had the best idea for a trick we could play on that boy," added Sarah. The three of them had grins that reminded me of three smiley buttons and I suddenly began to wonder if I shouldn't have come home.
"What kind of trick."
"Well James, you'd be part of it. I, uh, well, we thought what if Scott met someone who he thought was his date, but wasn't?"
"Who mom?"
They all burst out laughing. I began to get a sick feeling inside my stomach. I knew what they were about to suggest.
"Why you James," My sisters squealed.
"What?!"
"Darling, hear us out. We could dress you up as a girl. I think you'd be adorable, but still you're a skinny young man and you'd never match your sister with her curves and looks and when Scott comes in and meets you as Susan, we'll see what kind of character this young man has.
"James, please you have to do this."
"There's no way I'll do this."
Both girls started on me. "Please James. Please. You have to help us. Please. We'll be your slaves and we'll do anything you want if you'll do this." Mom had a dreamy smile on her face too. I knew I was melting inside. My mom, and really my sisters too, always looked out for me. Mom sacrificed so much for me and the girls practically worshipped me. Their pleading smiling faces told me how much they'd enjoy it. But a girl? How could I dress up as a girl? It sounded so strange and so unlike anything I'd ever do.
"Can't you get someone else?"
"No," they all cried. "It has to be a boy dressed up as a girl, that's what makes it so funny."
I gave a big sigh and said, "I'll agree to do it, but you can't tell anyone ever." Well, the three of them burst into laughter and took turns hugging and kissing me. My face turned red.
Mom said, "we'd better get started."
"Get started? It's two o'clock. What do you mean?"
They all laughed again and my sisters took me by both hands and led me upstairs. "First of all James, you need to shower while we choose an outfit for you." My face was in a deep frown.
Mom said, "oh James, this will be fun."
"OK," I said. I started to pull off my clothes and I shut the bathroom door. I could hear the girls through the door saying, no not that, oh that's cute, yes, no, yes, no. Boy, I thought, they're going to owe me big time.
After my shower, I walked back into my room wearing a bathrobe. Mon was waiting for me and in her hands were a set of Susan's underwear. "Mom?"
"Here James, try these on."
"MOM!"
"What?"
"Those are panties."
"Of course they are. Come on, slip them on. For me."
OK, for mom I'd put on girl's panties. I took the pink cotten "Jockeys for her" and slid them on. Well that wasn't too bad, but a bra too? What had I agreed to. "Come on young man, let me help you with this bra." I recognised it, one of my sister's old training bras. It had a little padding. I hadn't seen them in several years and now it's laughable to think that my sisters had padded bras.
"Mom, do I have to wear that?"
"Of course you do." Mom clasped it on. "There, was that so bad?" No, it wasn't, but it still felt weird. "Come on son, lets go to Susan's room." We crossed the hall and of course both the girls laughed when I entered. Sarah was holding these black wool tights.
"No, not those."
"Of course silly. You'll have to wear tights. I always wear them under my skirts and besides, the texture of these will easily hide the little amount of hair on your legs."
"Unless you want to shave them," added Susan. "Come on, we'll help you put them on."
I took a big gulp and sat on a chair. The three of them practically fought each other to help me into the tights. I was surprised at how comfortable they felt as we pulled them up over my legs and hips. Before I had much time to think, mom handed me a short black half slip. "Put this on darling."
"Really? I mean, do I have to?" I knew I had to, but this seemed to be unreasonable. However, as I stepped into it, I was amazed at its lightness. I glanced at my image in Susan's mirror and was surprised at how girlish my skinny shape appeared. My textured dark woolen legs were much like the legs of the girls whose bodies I had begun to notice that year.
Sarah had a charcoal grey turtle neck sweater which she helped me put on. Mom stood by holding Susan's grey jumper. I stepped into it and they zipped me up. Mom laughed, "take a look in the mirror little man."
I blushed, but looked. From my neck up, I looked like myself, but from the neck down I looked like a skinny girl. Someone who boys, certainly older boys, might dismiss, but a girl who was well on her way to becoming an attractive woman. It was surprising, but I reminded myself of the twins when they were thirteen. Susan said, "ladies, let's get him to mom's bathroom and finish his look." I hadn't thought about anything beyond putting her clothes on, but they had to do something with my face and hair. I knew that mom had some wigs left over from her college days and I figured I was about to be fitted with one.
Mom and the girls began to argue over what kind of look I should have. Mom had three wigs: redhead, long. Another that was brunette and long and a third that was blond and short. Mom asked me if I had a preference. I actually did, but felt as though I'd betray something of myself if I expressed it. I shook my head. Happily, mom took the red one and began to put it on my head. I looked at myself and loved it. With that wig, I certainly looked like a girl. My sisters thought it was perfect. Mom pulled it off my head.
"Mom? Why did you do that." I asked.
Mom laughed, "we have to make you up before I adjust it." Uh oh, make up? Well, I had gone this far. I sat back as mom and my sisters fussed over me. Mascara, eye liner, lipstick, and goodness only knows what else was applied. I didn't care for any of it. The lipstick's aroma seemed to settle into my nose and it made me uncomfortable, but when they had finished, the change in me was quite apparent. I could easily pass for a plain girl. I was slim, small busted, but tall and some guys might even find me attractive, not that I'd want that, but in no way was I an equal to my twins sisters or my beautiful mom.
"Well," Sarah exclaimed, " you're definately more attractive as a boy." They all agreed.
"But he is quite adorable as my third daughter," mom laughed.
"Now what," I asked.
"Why, you have to practice,""Practice what?"
My sisters took charge of a lesson in girlhood. They taught me to walk, to sit, how to shake hands with Scott. I made them promise that they wouldn't tell him I was their brother, but that I was a cousin. Susan and Sarah didn't like that, but I threatened to pull off my wig if they didn't. The truth was that I enjoyed being dressed as a girl. It felt different. I looked different, but all the new sensations felt exciting as a tried to move and act like a girl.
Soon it was time for Scott to arrive. Mom was to let him in. Sarah, who he had met would greet him and introduce me as Susan who would be hiding in the next room. I felt so nervous that I worried I'd sweat, but mom had me sit on the sofa and cross my legs. She stroked my head and called me her sweet baby girl. I felt funny hearing that. The doorbell rang and Scott entered.
I suddenly felt guilty because Scott looked like a very nice boy and I wondered why we should pull such a prank on him. I could see the smile build as he greeted Sarah. I saw him glance at me and realised that I almost didn't register. He probably had dismissed me as someone who certainly wasn't Sarah's "foxy" sister. As I was introduced, I saw a brief flash of dissappointment in his eyes, but Scott was a gentleman and he quickly buried it. He was a nice boy.
Then Susan appeared and she said that they pulled a trick on him and that I was their cousin who was visiting that weekend. Scott was such a getleman, he didn't seem mad at all. He laughed and I knew that he thought I was a girl. Then he invited me to come along with him and Susan. I suddenly felt terrorized at the prospect, but mom jumped in and rescued me. "No, No, Jamie and I have to catch up tonight."
However, mom snapped a photo of me and Scott. I was horrified. After Susan and her date left, mom looked at me and asked, "now what?"
"I'm getting out of this dress."
"Stay in it a while."
I felt temptation sweep through me. Why would I want to stay in a dress. Yes, it was enjoyable, but, but....
I pulled off my wig. "No mom, I'm going to take this off and get cleaned up." My foray into girlhood was over.
My sisters and mom said they were proud of me for being willing to do that prank. They never asked me to do anything like that again and one day, I ripped up the picture of Scott and me. Now, my wife held the picture. Mom had made copies. "James," who is this?
"I guess it's me."
A smile spread across my wife's face. "I thought it was you. You're so cute."
"It was a joke, a trick to fool Susan's date."
"I think it's cute. James, this is a coincidence, but I was going to ask if you'd be willing to let me dress you as a woman for the Hanson's Halloween party next month, but I was afraid to even ask. I had no idea you'd ever done it before. What do you think?"
My heart pounded, what did I think? I was a little scared and wasn't sure what to say. What would you do?
© 2001
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