This is my first attempt at an erotic story of any type. It is my sincerest hopes that you will enjoy this story. All warnings apply; if you are under 18 go away. If you enjoyed this story please e-mail all responses to me at [email protected]. This is not your typical story about a boy who needs to or has to dress like a girl. I thought some people would like something a different. I revised this story to fix grammar and spelling errors. The content has not changes and I fully intend to continue this series. I just hope I got all of them. Hope you enjoy this story as much as I did writing it. I know it’s been a long time coming, things in my life prevented this from occurring before. My apologies for the delay in a proper re-write.

This story is copyrighted by the author and is allowing free distribution to Crystals Story Site, Fiction Mania and Big Closet. Please look for more stories from here soon.

And now!

My Life in a Dress

By Sara D:

Chapter one: Finding out who you are.

Well I guess I should start by telling you a little about myself. My name is Shawn and I am a 14 year old boy, 5 foot 5 blond hair 110 lb. and I have fare skin. I have always liked being a boy and doing boy things. I liked playing with hot wheels, trucks and riding my bike. The only difference in me from other boys my age is that I am Gay, and I have a major crush on my best friend Josh. I can't help myself. He is just beautiful. He's my age, 5 foot 6 brown hair, a smile to die for, light skin and a body that could kill.
Josh and I have been friends since the two of us where in diapers. I and as long as I can remember I have always had a crush on him. Only till recently did I realize I was falling in love with him. Because every time I look at him I felt strange and I would get hard on just looking at him. It all came to light between us l one day during lunch period while day and Josh interrupted my day dreaming and said. "Hey, Shawn are you all right man?"

"Huh, oh sorry I was just lost in thought." I said recovering from the daydream

"Ok man. If you need to talk about something I am here for you". And that's how he is. A really nice guy, one of the reasons I love him so much. But as usual I kept to myself, feeling, that if I told him the truth I would lose our friendship forever. On the other hand I would do anything to get into his pants, Hey I'm a teenager I think about sex. Allot! Ok so get off my back. Well anyway after we were finished eating we went outside to take our afternoon stroll to look for chicks as he would call it. Josh would look at girls and say how cute they were, and point out which ones he would like to go out with. I would always respond with my usual agreement even though I never cared what any of them looked like.

After our stroll we headed for Gym class. Josh and I had our lockers next to each other. No let me tell you I have seen Josh naked a few times at his house and during gym class while changing but today was different. Today while we changed for gym he took of his boxers and revealed he had a hard on. This is the first time I saw him with a boner, and there I was staring right at it. Oh my god I thought. Then with a sly grin, he says, "Ok that's it, you and me are going to talk after school." Then he left to go to class.

The entire time during gym class he would not look at me. All this time I was sweating buckets, thinking he was going to pummel me or worse. After class was over he was his good old cheery self and changed in front of me without any more words said until we started to walk out to our next class when he said. "Don't forget Shawn I want to talk about this after school". This made me worry even more. The rest of the day went really slow. Josh and I met after school and started to walk home. He was quite at first but then he started to speak.

"So Shawn, tell me what's up with you?"

"I don't know what you are talking about" I responded hoping he would drop it.

"Come on Shawn, I'm still your best friend, just tell me the truth."

"The truth about what?" I was still afraid to say what I really wanted to.

"Bro., come on I saw the way you were looking at me at lunch and then I again saw you staring at my dick while changing for gym today."

"You saw that?" I said trying to shirk my desire not to talk about this.

"Yes, come on tell me!" He said with a roar.

"Are you sure you want to hear it?"

"Yes Dam it, SPILL IT!" He yelled.

"Ok man." And I actually started to tear up a little. He then put his hand on my shoulder and rubbed it in a friendly manner.

"No matter what I will always be your friend."

I tried to get the words out and my voice cracked as I began. "Look Josh, I'm Gay and I think I'm in love with you." Holly crap did I just say that, it just came out. I then tried to take back what I had just said. "Sorry man, I did not mean that."

"Yes you did, and I still am your friend but I don't like you in that way. Let's go home, ok."

"Ok, you really don’t care?" I said.

“Nope.” He answered and we were quite the rest of the way home to my house. We had plans to do home work together today and when we reached my house I expected him to go home but he said. "Hey we are still on for home work and play station right?"

"Are you sure you want to." I responded

"Yes dummy, like I said I'm still your friend even if you want to suck me off." He said with a snicker. And that's how it went for the rest of the day, I could not believe it he was cool with it even if I would never get any of him but that's cool I'd rather have him as a friend than not at all. Weeks went by as they always do. Josh would sometimes make fun of me by, saying something like. ‘Hey that guy has a nice cock, why don't you go suck him.’ Or he would flash his but at me and say ‘I bet you wish you could touch this’ and I would smile and think hell yes. Other than that everything went normally for us. We still hung out together. The only difference was he was a little shy when changing in front of me during gym class. The more and more I thought about Josh, the more in love I became with him. To the point it hurt to think about it, knowing I would never be able have him. Then one day while surfing the Nifty archive for stories I think I found an answer. I was doing my usual reading teen boy stories then I scrolled to the bottom and found a transgender story for teens. I got interested and started to read it. It was about a boy who wanted more than anything to be a girl and it ended up him going on a date with a friend of his and kissing. Which intrigued me to no end and I thought to myself, I wonder if I could dress as a girl and find a way to go on a date with Josh. I got up and went to the bathroom and looked at myself in the mirror and wondered if I looked feminine enough to do it. I was still unsure, so I went to ask my mother. Now let me tell you now my mother has always known I was gay and that I had a crush on Josh. We never kept any secrets from each other. So I asked her. "Mom, do you think I look like a girl?"

"Why do you ask honey?" she said with a worried look.

"Well, I just want to know if I could pass for a girl if I dressed the part." I asked again.

She looked at me quizzically for a second then said. "Is this a way to try and go out with Josh?"

"Yes." I responded a little embarrassed.

"Do you think that is a good Idea?" She asked with concern in her voice.

"It's the best one I can think of mom? I don't know what else I can do, and I love Josh so much I would do any think to go out with him."

"I know honey I just don't want Josh or you to get hurt."

"I know mom, but will you help me look pretty. If it does not work at least I tried." I answered hopefully.

"Ok, honey I'll help. I know how much you care for Josh, but as soon as you get serious, like kissing, I want you to tell him who you are."

"I will mom, don't worry."

"Ok honey, I trust you to make the right decision. How do want me to help?"

"Well I want to be pretty for him and I need the right clothes so I guess we should start by going shopping."

"Ok, we will go Thursday after school so you can be ready by Friday for Josh, but that part is up to you ok."

"Ok mom, you got a deal."

So that was the deal, mom would help me dress as a girl and I would find a way to get a date with Josh once I was dressed properly. I went to my room to think about how to make it happen. Then it came to me in a flash every Friday Josh and I went to the local arcade to play our favorite game. I could just show up their dressed as a girl and play that game and see what happens. So now I have my plan. Well Thursday finally came and I rushed home from school. I ran into the front door of the house and yelled "Mom I'm home let’s go!"

She responded "Not so fast young man, or should I say young Lady, get your but into the shower and use this cream on yourself from the shoulders down."

"What is this for mom?"

"It's hair remover, it will help you fit the part of a young lady."

"Ok thanks mom."

I went to my room shucked my close off and jumped into the shower. I washed my hair and then used the cream mom handed me. I waited a few minutes to rinse off, I watched in amazement as my body hair washed down the drain. I was completely hairless from the neck down. It looked weird but felt very nice. I then dried off and went back to my room to get dressed. As I walked into my room my mom followed me in, she had a small shopping bag with her and she handed it to me. With a puzzled look I asked. "What's in the bag?"

"Proper undergarments for shopping to get girls clothes honey go ahead and put them on and then get dressed in some jeans and a T-shirt."

I took the bag and said. "Ok, thanks again mom.”

She then left the room and I dropped my towel and opened the bag. I was amazed at what I found inside, a pair of pink satin panties, and matching bra. I thought how cool, an early start. I put them on but realized that the bra was a little difficult at first but I got it on by pulling around front and clasping it together that way. I then pulled up the panties and I must confess the felt wonderful. I finished with a pair of jeans and a t-shirt and pulled on my shoes and ran down the stairs to let my mother know I was ready to go. She grabbed her purse and we left for the mall. My first ever trip to shop for girls clothes. I had no idea what my mom had planned for the afternoon. I was a little scared but otherwise ok about not knowing what was to come. We soon arrived at the mall and mom parked outside a major department store. We walked in and went straight for the juniors department and boy was I in for a learning experience. I had been in that area before, but I never really paid any attention. I never would have guessed that there was so much to choose from. We started to look around and my mom bluntly said. "What would you like to get?"

"I have no idea, what do you think?

"Ok Shawn let’s see".

We looked around and she would ask my opinion about a certain dress or skirt, I had no clue. All I wanted is to look good so I picked a few out and said. "We should try these."

"Ok." She said and she pointed me towards the dressing rooms. I then turned white, she can’t be serious oh my god, I thought, is she crazy. She obviously saw my misgivings and horror. "You'll have to try them on to get a proper fit so you look good for Josh."

That did it I was in the dressing room in a second. Both dresses I had picked out fit good and looked really nice. With some padding up top, a wig and makeup I think this is going to work. That's when my mom asked to see me so she could see how the dress fit. I hesitantly stepped out of the safety of the dressing room and showed my mom. At the same time the sales lady walked up and asked if we could use any help. We both said no. Then she surprised us both by saying "That dress suits your daughter very nicely."

"Thank you." My mom told her.

After putting my heart back in my chest I put on my regular clothes. We went to the counter to pay for the things we liked. I ended up with two dresses, one skirt, a few blouses, 3 pairs of panty hose and 2 pairs of shoes. I did not get heals though I wasn't ready for those yet. My mother and I then walked out of the mall and she drove for a block or so and pulled over and surprised me and said. "Are you ready for the next step?"

"What step is that?" I asked a little confused.

"You will see in a minute, go over to that bathroom in the park and take an outfit and put it on then I'll tell you where were going."

I was a little apprehensive but did as she asked. I think she was having more fun with this then I was. I walked towards the bathrooms and stopped in front of the men's room and looked at mom for assurance. She casually pointed towards the women's bathroom. I looked over and got the hint. I walked into forbidden territory and started to undress. There I was a boy in the women's restroom in nothing other than a bra and panties. I then set my clothes on the bench and started to pull out the items I would be wearing. I first pulled out a package of tan nylons and put them on. Let me tell you, they are harder to put on then it looks. I got them on eventually. I then took out the dress and slipped on over my head, again did not look quite right. I then got an idea. I then grabbed some toilet paper and stuffed the bra until I was satisfied with the size of my new bust. I pulled out the white flat shoes and slipped them on. I looked in the mirror and saw myself in a dress for the first time. Ok for a start oh well I'm not done yet, this is just the beginning. I then folded my old clothes and put them in the bag I brought with me. I then straightened the dress and walked out to the car. As I opened the door and sat my mom corrected me by saying I should smooth the dress under me before I sit. So I tried again and did it right.

She then said. "You look nice sweet heart, by the way have you thought of a name for yourself yet?"

"Um No, I haven't." I thought for a few seconds then thought of my favorite character, How about Sara?"

"That's sounds perfect, Sara, yes perfect."

"Thanks mom."

We then began to drive of too who knows were. We then pulled in front of my mother's beauty salon. I then felt really uneasy. But she promised only her friend would their and would not tell anyone else. So I reluctantly walked into the salon. I was greeted by Carol my mother' hair dresser and close friend.

"Hello Fran and this is?" she said.

"This is my daughter Sara." Mom pointed to me.

"Well hello Sara and welcome, come over here and sit" She pointed to one of the chairs next to a sink and mirror.

I started to feel a little better when I saw she was not going to freak on me. Mom must have briefed her beforehand. As I sat in front of Carol she asked. "Have you given any thought to what type of hair style you would like?"

"No, not really, I just thought I could get a wig of some sort or pick form a selection." I responded hoping she would have one that I would like.

She then said. "That sounds good and easy. Let's see what we have and then you can pick any color you like."

"Blond" I said a little too quickly but no one seemed to notice.

"Ok, let me go and look."

As she left for the back room my mom smiled at me and said. "Are you sure you want to do this?"

"Yes mother more than anything." I answered.

In a few minutes Carol came back out with a nice looking Strawberry blond wig. She placed it on my head and adjusted it a few times then asked what I thought about it. I looked in the mirror and saw a cute teen aged girl in the mirror looking back at me.

"Wow, even without makeup I look like a girl." My mom shook her head in agreement. Then Carol led me to another table in the salon and began to apply makeup on my face. While she was doing that another woman from the salon took my right hand and began clipping and shaping my nails. After both were done I got to look at myself in the mirror and was totally amazed at how I looked. Even to me I looked like a babe. I thought to myself that I am going to pull this off with ease, I am going to make Josh's heart pound.

"You know Shawn; you look relay good, pretty even." My mom said looking at me with a smile.

"I know mom, it's almost scary." I said looking at my new self.

"I guess I should call you Sara from now on?" Mom said rubbing my shoulder.

"Yes, I should say so, so that we don't confuse anyone for now." I told her confidently and was sure no one would realize I was a boy in a dress.

Then I got a good look at my finger nails, they were longer than before. My mom must have seen my puzzled look on my face. "Honey, you know we will be able to remove those before you go back to school Monday."

"Oh, ok. They do look nice though.” I really did like the look that the nails and make up completed. “Thanks for all the help today Carol, I love the look.”

"You are so welcome Sara; I just hope I get to see you again some time.”

"You will see me for sure, see you next week." My mom answered and looked me over one more time.

“Have a good day Carol; I will see you soon too.” I told her, I had just realized I loved all this extra attention from my mom and had decided that Sara had to come out again some time.

My mom and I walked out of the Salon to the car and drove home. On our way home I told mom of my plan on how to bump into Josh Friday. She said it was a good Idea.

Friday morning I woke up and got ready for my day. Today being a school holiday, I knew Josh would be at the arcade early, so I gave him a call.

"Hello."

"Hey Josh its Shawn. Are you still going to the arcade today?"

"Hell yes, you ready to get your ass whopped?"

"Ha" I laughed. "In your dreams, well anyway I can't make it. I have to go to the doctors with my mom today."

"I hope it's not fatal." He chuckled.

"No my mom wants me to get a checkup and the only appointment they had was for today, but I will try and make it later in the afternoon."

"Ok Shawn, I'll see you later."

"Ok, later dude, bye."

After Josh hung up I check myself in the mirror and made sure I looked nothing like my old self, but what I saw was Sara, the new me and I must say I liked what I saw then wondered this is going to work. I then walked to the corner and waited for the bus to take me to the arcade four miles away. Within five minutes the bus arrived then I was on my way to the arcade. No one on the bus gave me a second look as I sat and waited for the bus to get to the mall.

Chapter 2: The Arcade

I arrived at the arcade in good time and I got off of the bus and walked to the end of the mall where the arcade was. As I walked in Josh was at our favorite game playing away. I walk up behind him cautiously as if I was interested in the game he was playing. He was doing well but not as good as me. I watched for a few minutes. Then he lost the game at a level I had beaten long ago. He turned around, saw me and smiled.

He greeted me as I walked up closer to the game. "Hi, do you know how to play this game?"

"Just a little bit." I answered.

"Would you like to play two players? I'll pay."

"Sure, I'd love too."

He then put in the right amount of quarters for two players and then we began to play. At first I was keeping myself from going a level above him, but after a while he was making the same mistakes he always did. So with sure experience I past him up and won the game and I even beat my own highest score. We both entered our initials and ended the game. He looked at me weird then smiled at me and said. "Either your good at this game, or It was just luck?"

"It's just luck I guess?" I said.

He then asked me "Hey would you like to grab a bite to eat with me?"

"Yah, I would love to." I said anxiously and I thought to myself, this is actually working.

He held out his hand and I reached for it and I held his hand for the first time. Oh what a feeling, I was so nervous. I began to perspire. I hope he doesn't notice. We walked out towards the food court and got some burgers and cokes. We sat down and began to eat.

He then asked "You sure were good at that game, are you sure you don't play it much?"

"Like I said, I've played it a few times before I guess I got lucky, like you said."

"Uh huh sure!" He said with a laugh. "My name is Josh, what's yours?"

"Sara" I said.

After our lunch Josh stood up and asked. "Hey, would you like to go see a movie with me today?"

"Yes!" I said, just a little too enthusiastically.

He then said "What would you like to see?"

I had to think quickly. "Um, How about Mission to Mars?"

"That sound great, let's go." Josh agreed to my movie choice.

So off we went to the theater and arrived ten minutes before show time, what luck. Josh bought the tickets, took my hand in his and led the way towards the concessions line. He bought us some popcorn and some drinks. We then choose seats in the back of the theater and sat down and waited for the movie to start. The lights went down, the music started and the film began. After a while he reached for my hand and held it in his. We sat like that for a while. Then during the dance scene he put his arm around my shoulder and put his hand on my right breast. I could feel it and I shuddered. I fell totally in love. I knew then that I had him, and thought what the hell and I put my left hand in his lap and felt his manhood for the first time in my life. It was wonderful and he was hard. I ran my hand up and down the shaft several times and at the same time was also looking into his gorgeous eyes. He had a very content look on his face then leaned toward me and touched his lips to mine and we kissed for the first time. It was the most wonderful feeling in the world but soon realized my promise to my mom and I got scared at the same time so I pulled away from him and said, "Sorry I can't do this Josh" and then ran out of the theater towards the front doors.

Josh caught up with me as I reached for the door to open it; he grabbed me by the arm and yelled. "Shawn, wait!"

I thought I was going to die. He knows who I am and as I turned to face him with tears welling in my eyes and said.

"How did you know?"

"I've known since the arcade"

"What, how?" I said.

When you won the game you used your usual initials."

"Oh shit" I said.

"Yep, that's when I realized who you were and how you were dressed and said what the hell, if he is willing to dress like that and look as good as you do why not humor him."

"Really?"

"Yes really, but something happened while we were eating."

"What's that Josh?"

"I was thinking about you, I began to realize I was attracted to you, the real you. I’ve been hiding my feelings for you a long time and not acting on them, for fear you would hate me. After you told me how you’re truly felt I was stunned and happy at the same time but for some reason I couldn’t find the courage to tell you how I felt for you. Then during the movie I thought now is the time to show you how I feel and too see might happen. I love you as you, or as Sara, I don’t care which. I love being with you more than any person in the world.

"It was wonderful Josh; I love you so much too, what happens next?"

"I know, I think we should find somewhere else to talk"

"Ok, how's my house sound?"

"Good, let's go."

"Ok." About fifteen minutes later we arrived at my house. My mom's car was in the driveway and we entered the house and my mom was sitting in the living room, she smiled at us and motioned for us to sit. I smoothed my dress, took Josh’s hand in mine and we sat on the couch next to each other. Mom smiled at us and started asking questions.

“So how was your date?” Mom finally asked smiling bigger.

Authors Notes
I ended it here because this is where the original story I posted all those years ago ended. I changed the wording to make it work together a little better and to give myself a place to start the next chapter.

Coming soon, Chapter 3:
I know some of you asked me to keep the story clean. My story must move forward and Josh and Sara’s relationship must also move forward, so in chapter 3 you will find descriptions of their budding relationship, including sexual. I apologize for those who asked for a clean story, but it’s how I see them growing into a true relationship. But I do promise to keep it from becoming too graphic, it’s my intent to keep this series rated R. Thanks again for reading. Sara D.