I originally wrote this for storysite and decided to amend some errors. The original Story changed immensely and is told from a different point of view other than first person

Two boys discover they are more alike but never had let the other know. One boy is model of feminine attire the other boy just enjoys dressing as a girl and unsure of herself when she begins to find her friend very attractive.

The Model and the Cross Dresser
Jill Micayla

Hal went over to visit his friend Jimmy. Jimmy had called and told Hal his parents were out of the house and that maybe they could hang out together and play on the X-box. Hal said it sounded good but he would be over with in a half hour

Hal hung up and went to his bedroom there he removed the dress he had on. He took of the necklace and earrings, decided the panties and hose could stay and then put on a pair of slacks and a polo shirt.

Hal had asked Jimmy id his sister Sister Elaine was there. Jimmy told Hal she would be out of town for the next two weeks. Hal and Elaine were good friends when Jimmy was away for modeling appointments. She and Hal would do things together including her introducing Hal to being a part time girl.

Hal arrived at Jimmies and saw the picture window curtain open and close, He thought it strange coming from his best friend. He tried the door knob and the front door opened and so he walked in. As he began to turn towards the hallway to the bedrooms he thought he saw a glimpse of a familiar dress behind the door.

He was stunned to see his friend Jimmy in the dress standing there smiling.

“I’ve been wanting and waiting to tell you for a while that I model dresses at designers requests. I hope you aren’t upset?”

“I’m okay with it. As long as it makes you happy and you do look very confident as a girl.”

“I wasn’t sure how you would take my news most people thing I am gay and usually want ot beat me up.”

“I for one don’t think you are gay and I promise not to beat you up.”

“There is a part of me that likes boys when I am dressed like a girl.”

“Again whatever makes you happy I’m not a guy who likes other guys, but I will still be your friend because we always have been. I think you look very nice, I know I’ve seen your picture on several magazines.”

“You mean you are not upset?”

“Should I be?”

“Well no, but how many of your friends like wearing dresses?”

“Several that I know of, but then again they are girls.”

“I meant how many boys do you know?”

“You are my first guy friend that has told me he likes dressing like a girl.”

“Have you ever wondered what it would be like?

Hal was lost for a moment. How was he going to answer that question without revealing that He and Jimmies sister had been out several times as two girls.
I’m an only child so I guess I never had an opportunity to think about it or take any action in doing it.”
Hal was hoping Jimmy would accept his reasoning.

“My sister was responsible for me liking to dress like a girl. When we were smaller we used to dress as twins and do ads for a local dress shop. They called me Jaime when I was in a dress. I liked the attention and soon had a chance to model girls outfits for money.”

“You don’t mind being a girl?”

“When I am dressed like a girl, I walk and talk like a girl and I will hold hands with boys. I have kissed several boys but never have had sex with one.”

“So you don’t know if you are gay?”

“I don’t think I am. I was told I was born with both sexes and that apparently my parents chose the wrong sex for me. I see boys as an attraction for me but I try to stay away as two boys together has to make somebody gay.”

“I don’t think so; if you should have been a girl then you are a girl with girl’s feelings. Liking boys is natural for you. I really don’t believe you are gay. To be honest I think you are very pretty. If I didn’t know you were a boy I would date you.
”
Let’s make a bet, if you win at our playing on the X-box, I’ll change back to boys clothes; however if you lose You have to let me dress you completely as a girl.”

Hal knew he was good on the X-box and would have no problem winning.

“It’s a deal if I win you’ll be a boy for the rest of the day. If I lose I’ll be joining you as a girl.”

When they sat on the bed to play Hal could smell Jaime’s perfume and the thought of being a girl along with Jaime was beginning to work on him. Maybe if he made it look like he was having a problem then he would let Jaime dress him as a girl.

Hal lost all three games they played. He no longer wanted to be a boy but wanted to be just like Jaime. He liked being a girl, Elaine had taught him so much, but how was he going to explain the hose and the panties if Jaime was going to help him become a girl.
Hal knew one way but wasn’t sure if it would work. He himself had never been with a boy little lone with a boy in a dress. Now he was thinking of how nice it could be.

“Jaime I have to be honest. Since you were honest with me it’s my turn. I am right now wearing panties and panty hose. I didn’t know about Jaime until today. I do cross dress as much as I can, but I don’t know how I feel about boys or even boys like you.”

“Do you have a girl’s name?

“Helen, I am called Helen by those who know me was a girl.”

“Well Helen go to my sisters room and pick out an outfit to wear and then I can fix your hair and help you with make-up.”

Hal looked at his watch declaring he needed to be home and told Jaime she was very nice looking and before he could get to the door she came to him and put her arms around him and they kissed. Hal wasn’t repulsed by the kiss but rather thoroughly enjoyed it and then they French kissed and Hal knew that he was going to have a hard time as a boy in a dress was turning him on.

Hal arrived home still in a bit of a daze, he had just kissed his best friend and liked it. He had never kissed a girl, but Jaime didn’t look like a boy or even smell like a boy. Hal wasn’t sure what he was going to do.

His mom was due home any minute and Hal knew that this being a Saturday she would want to take her daughter out to dinner. Mom had been making Hal dress as a girl when she saw him and Elaine leaving Elaine’s house. Hal’s mom wasn’t totally sure it was her son until she saw Hal at home and he was still wearing mascara and eye shadow.

Hal went up to his room and opened his closet. His closet was divided one side to his masculine clothes the other to his feminine wardrobe.

“Helen, I am home. We have an hour before we meet a friend of mine and her daughter for dinner at the Shamrock. Wear something nice so her daughter will not suspect you of being a boy.”

Hal wasn’t sure what was going on, his mother never took her and Helen out to dine with anyone else. He needed to talk to his mom about the day. He was looking forward to a day with Jaime again. He liked Jaime as a girl and shuddered when he knew she was a boy. He had never had feeling for a girl or a boy and now he was thinking of a girl who was a boy.

Hal was soon dressed, make up was done correctly and the dress he wore was an A-line with a scooped neck. The dress had a tiny pink jacket that matched the dress. He sat in the living room waiting for his mom to come out of her bedroom.

“You look like you are upset, please tell me what it is and maybe I can help you remedy the situatiion

"Oh mom, I feel confused, I discovered I like kissing boys and I am so ashamed that I do."

"And how did you discover that kissing a boy was pleasant for you?"

"I went over to Jimmy's and he was dressed like a girl, I did not react and before I left to come home he came over and put his arms around me and kissed me."

Hal was sobbing; "I didn’t expect the kiss from him but when our lips touched I wanted it to keep going, mom! I French kissed my best friend."

"What did Jimmy do?"

“He acted just as though it was a very natural thing to do. I tingled when he kissed me and I want to kiss him again, but I was scared so I hurried home.”

"Don't you think you owe him an apology for just walking away, and it is about time he let you know that he make a living modeling girls clothes for a catalog?"

She smiled at Hal. "Sweetie if he kissed you and did not react when you began to kiss him back he is probably doing what you are doing right now, trying to figure out how he is going to tell you he was turned by you."

"Maybe I should invite him over and let him see me as Helen and go for a walk to tell him I really like her.”

“You can do that after dinner. We need to get going so we won’t lose our reservations.”
Mom drove quietly as they headed out to dinner, she was usually very chatty but this time she remained quiet. When she pulled into the parking lot and Hal saw Jaime and his mom entering The Shamrock.

“Are the people we are meeting Jaime and his mom?”

“Yes they are, don’t be uncomfortable you already said you liked kissing Jaime and now he gets to meet Helen.”

Hal and his mother entered the Shamrock and headed to their table. Helen saw Jaime staring at her as though he was trying to figure out who Helen was.
Mom introduced Helen to Jaime and her mother. The four sat down the mothers next to each other and the daughters nest to each other.

“I hadn’t planned on seeing you again today. I cannot describe our encounter before I left to go home. Let’s just say I have a lot to think about.

Jaime said that when he kissed Hal he felt different from when he kissed other boys and that he was trying to figure out why Hal was so different. I told him that was probably because everything he does is centered around being a girl. He reminded Hal that he and Elaine were close. He asked how Hal was going to
explain to her about his dressing like a girl and enjoys kissing other boys. I told him she already knew. That she was the one who introduced me to femininity.

The waiter took their orders, and it was quite around the table. When the food came the four chit chatted about the two boys presenting themselves as daughters.

Hals mother told Jaime’s mother that the two girls had become more than just friends.

When dinner was over the four of them went to Hals house for more conversation. Helen and Jaime want to take a walk.

“You do look nice in a dress, I think you could do some modeling.”

“Think for the time being we need to define our relationship. Are we two boys or two girls? I enjoyed the kiss today, but I have never kissed another boy before. I didn’t know how much I was going to like it.”

“I took a chance kissing you but when our lips met I could feel you calm down. I think from now on we just dress as girls. I think you are very cute Helen. My sister did a good job on making you a girl.”

“Can we have a date where you are the boy, I want to experience the things a girl experiences on her first date with a boy.”

“You’re willing to be a girl for me, I can’t wait to tell Elaine how well she did with feminizing you.”

“She had a willing subject, besides she told me that I should have been a model.”

“I can see that, but first we have to have a boy girl date. I’ll pick you up on Friday. Dress casual if you would like, a sun dress would look good on you.”
They embraced again this time Helen was ready for he passionate kiss, what she wasn’t ready for is when Jaime puller her into him with his hands on her butt

Helen was in her room redecorating. She was removing the things that said the room was a boys and was replacing them with definite feminine items. She saw her mom peeking in.

“Do you think I can go to school as a girl? I guess I should wait a while to make sure I can withstand being a girl full time.”

"I agree with you on the wait. I think things are going too fast for you and although you for the moment feel like you want to be a girl forever. It’s not just the clothes and a boyfriend. As a girl you have to really take care of yourself. Let’s take it slow and if I think you should progress a little faster I’ll let you know.”

“I do feel like I am in love with Jimmy, when we kiss I get all tingly and want more.”

“Just take your time. If it is meant to be it will happen if not then there is another who may take you farther into the path of womanhood.”

When Jamie is on the road Helen writes to him daily. She and Elaine spend more time together with Elaine teaching Helen all about being female.

Helen spent a day crying because she was confused. She was very adept at being a teenage girl. She sometimes missed being a boy until she would see a group of boys roughhousing. Then she was glad she had chosen to be a girl.