Several of us were sitting by the pool, enjoying the warm sun while we took a break from the seminars and parties that were going on all around us. Myself, I had attended 12 of these conventions, designed for the transgendered to meet and enjoy themselves in a safe environment. I saw them come in, Mom, dad, and a skinny kid that was about 14. Nothing special about them, just average folks. But the kid set his eyes on myself and the others, then I saw his eyes go wide, and that little smile of his broke on his face. Even after he was in the water, he kept focused on us, and it became clear to me that the boy was more than curious. His mother was the talkative type, and struck up a conversation with us, asking why we did what we do, were we married, had kids and so on. She was very surprised to find out that all of us there were married, had good jobs, kids, and dressing as women had no effect on any of that portion of our lives. Harmless was the term one of my friends used. Her son drifted over, and began to ask how we did certain things, and it became clearly obvious to all of us that the boy was one of us. Hidden and scared perhaps, but the girl he had inside would appear someday, whether anyone liked it or not.
His hair, blond and shiny, came to just below his ears, and he was hairless as far as we could see. I looked at my friend Joann, winked, and she nodded her head. She also saw it.
"Is it hard?" the boy asked, "doing makeup I mean?"
"Not really" I said, "in fact, I’ll bet that you would be so pretty that most of the girls in your school would be jealous!"
I said that just to get a reaction, and I did, but not from the boy, or his mother. His dad spoke up.
"You guys have the body mass to get away with it. Kenny is so skinny that there is no way it would ever work!"
"Oh, I don’t know about that Jim, Kenny might make a very pretty girl." His mother sounded forceful.
The entire area went silent after his mother said that. We all knew that the boy would turn out to be a really nice looking girl, but of course, none of us would even consider mentioning it, nor would we even attempt to help him, even if his parents agreed, unless one or both of them were in the room at the time. No chance.
"I’m willing to try it dad. The way they look, who knows, maybe they’re right and you’re wrong."
"You would be willing to let yourself be dressed up as a girl? Kenny, are you sure about this?"
"We are on vacation, and a long way from home dad, so why not?"
The kid was provoking his father, hoping he would agree just so we could prove him wrong! That’s when I spoke up, and told the parents that given the boys size, it was doubtful anyone of our people had anything that would fit him, which is when his mother mentioned that there was a super mart nearby, and if one of us went with her, she would buy what was needed, and she would allow us to make over her son! Almost in unison, Joann and I said "okay", and we went to change. An hour later, Joann, Kenny, his mother and I were at super mart. It was easy. A black skirt with small red flowers on it, a red off the shoulder tee shirt, a bra in an A cup, some low black heels and pantyhose. Makeup was not going to be a problem. I whispered in Kenny’s mother’s ear, and she smiled and nodded her head. She took Kenny away from Joann and I, then we picked out a silver metallic sheath dress for him. Twin straps, one over each shoulder, a square cut neckline, and then some silver shoes. This kid was going to be a knock out.
As soon as we got back to the hotel, the mother told her husband that we had invited them to join us that night for our dinner. We had a band scheduled, along with a talent show, and that Kenny would make his first appearance at the dinner that night. We took the mother and Kenny to my room for his makeover. I had him strip to his briefs, then wet his hair and started to put in a few rollers while Joann set out the makeup. His skin was clear and pale, so he did not need a lot, just a touch. In fact, we didn’t even use any foundation on him. Just powder, blusher, eye shadow, eyeliner and lipstick. His mother handed Kenny a pair of panties, which made him blush, but as she turned around, he stripped off the briefs, pulled on the panties, and without a word, tucked his tiny member out of sight! He was definitely one of us. Joann did his makeup, then his mother helped him with the bra, starting to stuff the cups with tissue until I handed her some small foam breastforms, the cheap ones. They were perfect on his frame.
We coached him on how to pull on the pantyhose, but he really didn’t need it, and I’m sure that his mother noticed that. Using a folded washrag, I stuffed it between his skin and panties, one on each side, and all at once he had hips that were in perfect proportion to his age and size. Then I slipped the silver dress over his head and zipped it up. He was young and beautiful, there was no doubt about it. I took out the rollers, and using a curling iron, created a wavy bob that was just right. Silver chandelier earrings and bracelet, then we had him step into the shoes. I thought his mother was going to faint when she looked at him from head to toe. "Oh my" she said even as Joann set him down and started in on his nails. Just some minor filing, then a soft pink polish. Perfume, then I handed him the lipstick. When he looked in the mirror, it would be the first time he had seen himself as a girl, at least this way.
We all saw him pause, then, just like he had been doing it all his life, he colored his lips with the lipstick, saw the gloss on the counter, and added that!
"Emily" he said with no hesitation, "You can call me Emily."
"Your father is going to go nuts when he sees you Ke…Emily!"
"Yeah, I know. This is so cool mom! I love it!"
"Umm, maybe we should let Emily stay here with us while you go change for dinner. We have to get ready ourselves, and I’m thinking that Emily should make an entrance tonight. Don’t you?"
She looked at Joann and I, saw that it wouldn’t take us long to get ready, and nodded her head. As she left, so did Joann. She would get ready first while Emily stayed with me, then go with Joann while I got ready. It took about an hour between us. I wore a white silk jacket dress with white heels while Joann wore a red sequined dress with red patent leather heels. With Emily along, we rode the elevator down, then walked right through a fast pitch softball league team that was staying at the hotel. Every one of those boys had their eyes on Emily, and she knew it. I saw her quick little smile and shy look as she passed the boys. Perfect. She even had the look down pat. "Ready?" I asked, then we walked into the dining room.
As we walked in, every eye was on us. Emily was clearly very young, and also not old enough to be a part of our convention, yet, as she was between Joann and I, they all knew that Emily was a boy. Her father stood up when he saw his son for the first time, dressed as a girl. I myself heard him gulp when she stood right in front of him.
"Hi daddy! Well? What do you think?"
"Her name is Emily dear." Her mother sat next to Emily, I sat on her left, then her father, and Joann. Every movement, hand action and gesture was so feminine that I would not have known if I hadn’t helped change her myself. Emily had the gift of youth, beauty, desire, and now, the skills to become a girl, and she knew it. It was written all over her face as she could not quit smiling. With every movement, Emily glittered in the low light, the shiny metallic dress glowing like a light, her small but very nice bustline merely accented by the light. She was in heaven, and began to tease her father, until I finally whispered in her ear.
"Emily, we all know that you like being a girl, and you are cute, but if you continue to provoke your father, just how long will he go along with this?"
That brought her up straight, and after that, she was a perfect young lady. During the comments, and since I was scheduled to speak, I had Emily stand up, then join me at center stage where I informed everyone that the girl they saw there, was the very same young man that we had all seen earlier that day, and with his parents permission, we had made him over. That brought the house to their feet, clapping and yelling. Letting Emily walk back to the table, I watched as she rolled her hips just like a girl would. She was ours now, but she always was anyway. It was a fun party, and later, the band started. Emily’s parents were dancing when a young man appeared at our table, clean, wearing a jeans and a shirt, a smile plastered all over his face.
"Excuse me, but would you like to dance?"
He wasn’t asking me, I’m old enough to be his Grandma. He was looking straight at Emily! Fear crossed her face, just a fleeting look before she smiled at the boy, then took his hand. I looked out, and saw her father staring at Emily as she let the boy take her into his arms and lead her around the dance floor. Emily didn’t even bother to look worried. One dance and she was back at our table, the young man retreating to the doorway. Her father wanted to say something, but I saw the mother restrain him, and Emily was blissfully unaware of the turmoil she had caused her father. Twice more that night the same young man asked her to dance, and twice more she agreed. By the time the party broke up, Emily was in seventh heaven, her mother merely confused and her father perplexed. We all said goodnight, and went to our rooms. I did not expect to see Emily ever again.
The next morning Joann and I were at breakfast when I saw a familiar blonde head walking by. It was attached to a young girl, and she wore a short black mini skirt that had red flowers on it, a red off the shoulder top, her makeup perfect, low black heels on her feet. I saw her parents right behind her as the three of them went to a table and ordered breakfast. Emily had managed to get her parents to let her dress as a girl one more day. I wondered how she did it. On the way out, we stopped at their table.
"I see you’re back!"
"Daddy said I could. He said I look better than some of the girls in our neighborhood!"
"You are very pretty Emily, and I’m sure that you found out something about yourself you may not have known, but don’t push it in peoples face. Just be the girl you are, and live life to the fullest."
"Janet is right" Joann said, "This can be very hard on a person, especially your folks. You’ll have to work on a way to let Emily come an visit once in a while, but I know that you can. Good luck."
Joann and I shook their hands, then started to walk away when her father stopped us when we reached the door.
"She is like you, isn’t she? I mean, she’ll grow up to be like you."
"Sir" I said, "Emily may be like us. That is, she’ll want to get dressed up once in a while and be perfectly content that way. Or she might feel that she has no choice. She might find out that she was meant to be a girl, in which case all you can do is love her, support her, and teach her all the right things."
"Putting on a dress won’t make her crazy" Joann added, "But if you try and stop her, especially if she decides that it’s right for her, then she’ll go crazy, get sneaky, lie to you and all that. You don’t want that, and I’ll bet she doesn’t either."
"It’s just that she’s so damned cute! I never figured my son would…"
"Look like this?" I said, "Or that she would love it?"
"Yes."
He looked frustrated, yet he managed a smile and told us they had decided to let Emily go home with them. I left that day, and have not seen or heard from them, but I might. They have my card, and know how to contact me. Emily, the girl they all discovered, is I’m certain, going to be a fixture at their house, and based on the mother, she’ll be a lady right to her core. Cute too.
This did happen, but as in all things, names change and events are slightly different. It may have even been a girl we made over, just to show her how pretty she really was, or was it a boy, just as described? There were 120 witnesses that saw the girl in the silver dress and bright smile. Was it a boy? Or was it a girl? You decide.
© 2000
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