Crystal's StorySite

The following is a true story. Although some names have been changed, the events of this story did happen as they are portrayed. No part of this story may be copied in any way without the express written consent of the author.


More Than I Ever Imagined!

by Britney


Part 1: A New Image of Self

It all began in October when I was only 14 years old. My High School was having a ''Miss Octoberfest Pageant" in a few weeks and everyone was talking about it. However, this wasn't your average beauty pageant. this was going to be very different. In this pageant the boys would be competing to see who made the prettiest girl.

Every girl in school was after their boyfriends to let them enter them in the pageant. Every boy was refusing to be 'made over'. I wasn't an exception.

I don't think it had even been 10 minutes since the pageant was first announced that my girlfriend, Katie, was begging me to enter.

"Please Brett... I really want you to do this."

"I already said no!"

"Come on, they're just clothes!"

And that's about all I heard for the rest of the week. It was getting to the point where I didn't even want to talk to her because of the constant nagging. Normally if a girl got this annoying I'd dump her, but Katie and I had something special, something I didn't want to lose. So despite my better judgement I agreed to enter the pageant.

Now there were several reasons I didn't want to enter. Besides making a fool of myself and having my friends make fun of me for the next couple of years, There was still one thing that really scared me about doing this whole thing. That was the fact that I knew that I would make a convincing looking girl.

Don't get me wrong, I'm not a feminine looking guy. Its just that I've always been a pretty skinny kid, I've got long hair and I'm not exactly a hairy guy. So with the right clothes and some make-up I'd probably look like a girl.

I tired to push the thoughts out of my mind and didn't worry about it again until Monday morning.


"We need to get started as soon as possible."

"Started on what?"

"On your stuff for the pageant. We need to decide what you're going to wear, how we're going to do your hair and make-up and we also need to think up a girl's name for you to use."

"why do I need a girl's name?"

"You're going to be dressed like one so you need a name that will match how you'll look."

"oh, I guess that makes sense."

"It should probably be close to you're real name so that it won't be too hard for you to remember."

"ok, so what's a girls name that is close to Brett?"

"What about Britney? That's pretty close and its a really cute name."

"can we choose something that's not so... feminine, please?"

"Brett, these are girl's names we're talking about .they're all going to be feminine."

"But does it have to be Britney?"

"That's as close as we're going to get to your boy's name. How about we call you Brit for short?"

"I guess that will work."

"Great! How about you come over to my place after school and we can get you all dressed up? Most of my stuff should fit you, we're abort the same size."

"Katie, the pageant isn't for two weeks, do we have to start tonight?"

"Yes we do. This is more than you just putting on a dress. You have to learn how to BE a girl. That means looking, sounding and acting like a girl. That means lots of practise"

This is just great. It seems like I've really got myself in over my head this time. "Katie, how much is 'lots'?"

"Well I figured that you could practise over at my place everyday after school and then there's weekends..."


"You're going to need the practise."

"Yeah, but everyday!?"

"Don't worry about it, just relax and have fun. Besides, it will just be the two of us... alone... in my bedroom."

I couldn't turn that down now could I?

"OK, I'll meet you at your locker after school."



l wasn't able to concentrate on my school work for the rest of the day. All I could think about was my impending 'dress-up session' over at Katie's place. To say I was nervous would be an understatement. I was scared. Although Katie and I had only been dating for about eight months, I had known her since we were little. Katie wasn't one to do things half way. I knew my 'transformation' was going to be very detailed. And being an only child in a fairly wealthy family and being very spoiled she had the resources to really make me over if she wanted. There was no doubt in my mind that she probably had already planned this whole thing out. School finally ended for the day and I made my way to meet up with Katie.



"OK, first you need to go take a shower while I sort out some clothes for you. Use the body wash, shampoo and conditioner in the shower and then just wrap your hair in a towel and we'll take care of it later. There's also a bottle of hair remover under the sink you need to use before you shower..."

"Hair remover? Is that really necessary?"

"Yes it is, now listen carefully, we need to hurry up. Cover all the hair on your body from the neck down and then follow the instructions on the bottle. When you get out of the shower, use the moisturizer on the counter, put on a towel and come in my room."

Reluctantly I went to do as I had been told. The hair remover started itching like crazy and the 10 minute wait before I could wash it all off felt like an eternity. The body wash and shampoo left me clean and smelling like strawberries. After about 20 minutes I entered Katie's room.

"OK, lets get started. Panties first."

I simply complied and slipped into them. They were string bikini panties in light blue with royal blue edges. They fit fairly snug as I pulled them around my hips. I was instructed by Katie to tuck my equipment back between my legs before pulling the panties up all the way. It wasn't the most comfortable feeling in the world, but it was hardly unbearable. Next came the bra. I was told that I was going to be a 34C for the pageant. The bra was a match to the panties and was soon being stuffed with several pairs of pantyhose. I was then led over to Katie's vanity were she began work on my hair.



After working on my hair with a curling iron and trying several different styles of make-up I was brought back over to the closet to get dressed.

"Can I at least wear something casual?" was my final plea after begging to wear pants for the last 10 minutes, even after being informed numerous times that her pants wouldn't be long enough to fit me.

What I ended up with was a denim skirt, that was way too short, a pink turtleneck sweater and a pair of black knee high boots with a 4'' heel. I was then led over to the mirror where my fears were realized. I looked like a girl!

I stood there staring at myself. The golden curls of my hair bounced as I turned my head from side to side. I couldn't believe how I looked. My legs were definitely my best feature due to my height. At 5' 9" I had some pretty long legs and in a short skirt they seemed to go on forever. After a few minutes Katie came up behind me and wrapped her arms around my waist.

"I can't get over how beautiful you are," she whispered in my ear. "I knew that you would be pretty but I didn't expect you to look this good."

"Me neither."

Katie slipped her arms out from around me and turned me around to face her.

"Would Britney like a kiss?"

"Yes she would."

We moved closer until our lips met. As our lips ran together l felt a hand on the back of my thigh. It gently caressed my leg, slowly moving up to the hem of my skirt. I was becoming lost in the embrace, and then the hand was up my skirt, running softly across my panties.


Our make-out session lasted for the next 30 minutes until were were both worn out. As I lay there on the bed reflecting on what had just happened between us, I realized that over the last 8 months that we had been dating we had never had such a passionate time as we had just had. Although I didn't want to admit it, I knew that I liked the way that the panties had felt as Katie had stroked them or the way that our kiss felt with us both wearing make-up. I really didn't want to accept the way I felt, but l knew that I really enjoyed the way that I was dressed and I felt as through Katie did too.

"Katie? Can I ask you something?"

"Sure, What's up?"

"Do you find me more attractive dressed as a boy or a girl?"

"Oh Brett... to be honest, I don't know. Before today I was really attracted to guys, I was really attracted to you, but after seeing you all dressed up I couldn't believe how turned on I was by the way you looked. I still really like Brett, but Britney really turns me on. I know it sounds weird, but that's how I feel."

"Oh... I think I like Britney too."

"Really? That's so cool, maybe you can still be Britney after the pageant is over."

"Maybe, this is still pretty weird."

"Well lets get back to work. First we need to re-do your make-up because it is really messed up. Then we start your first lesson, walking in heels."

"Ok, but you should probably fix your make- up too."

Katie turned to look at herself in the mirror and started to giggle at the sight of her reflection. "Yeah, it looks like some girl has been kissing me, there's lipstick all over my neck."



"You seem to be getting the hang of those heels. You even swing your hips when you walk, it looks sexy!"

"Well if it looks sexy, come kiss me!"

"I just fixed your make-up and I'm not going to fix it again tonight. If you want a kiss so bad then you're going to have to learn to do your our make-up."

With that I was then given a quick lesson in the art of make-up. I was in the middle of doing my latest attempt at mascara when Katie's phone rang, scaring the crap out of me in the process.

"Brit, that was your Mom. she said that your brother is on his way to pick you up. We need to hurry up and get you changed."

I changed faster than l ever had before. I ended up just putting on my boxers over the panties. I quickly scrubbed at my face to remove any traces of make-up, only to look in the mirror and realize that my hair was still full of curls. Just then the doorbell rang. I ended up with my hair pulled back in a low ponytail and with my hat on you could barely tell that it was curly. After one final kiss I was out the door and on my way home in my brother's car.



The rest of the night was uneventful and I was soon back at school, bored out of my mind. As I sat there in class I couldn't help myself from daydreaming about the upcoming time over at Katie's place. I knew that I shouldn't be looking forward to being dressed as a girl, it just wasn't normal for a boy to do things like that. But I couldn't help remembering what the clothes had felt like the day before.

The day soon ended and Katie and I made our way to her house. Within a few minutes after arriving I was already changed into girl's clothes. For today I would be wearing a fairly tight fitting red dress, once again with a very short skirt. With that was a pair of 3" heeled sandals in black and of course, bra and panties in red.

"That dress looks awesome on you Brit. Hmm... but we need to find something better to use for your boobs though. Why don't you go and try to do your make-up while I try to find something."

''Uh... ok, what about my hair?"

"Just put it in a ponytail for now."

So with that I sat down to do my make-up and Katie left to go find me some better boobs.

I'm not exactly a pro when it comes to hair and make-up, having only done them for the first time the day before.

So after about 40 minutes I was finally done and went to go look for Katie.

I found her in the kitchen with the phonebook open and several pages of notes.

"Hey there beautiful. I thought you got lost up there."

"It just took me awhile to get everything on right. What are you doing?"

"I'm trying to find you some boobs, remember?"

"In the phonebook?"

"Uh huh, and I think I found some too. I'm going to get them this weekend."

"Uh... ok. So what are we doing today?"

"You're getting pretty good in these heels, so today I think we'll work on your mannerisms."

The next 2 hours consisted of me learning to sit and walk in a skirt, use my hands when I talk, etc., and repeating them over and over again.

"Brett, I know you're pretty good at imitating people's voices and you need to learn to talk like a girl. Can you work on that over the next few days?"

I agreed that I would practice sounding like a girl when I had some spare time. As I was getting dressed in my 'boy clothes' again Katie decided to inform me what we would be doing this weekend.

"Plan to spend the weekend over here. Saturday morning we'll get you dressed right away, then you can practice while I go pick up a few things. Then you get to have your public debut, I thought we could go see a movie or something, then do some shopping. My parents are going to be gone so you can spend the night and then on Sunday I thought we could go to the park and have a picnic. What do you think?"

"You want me to spend the whole weekend as a girl, out in public?"

"It will be good practice and we'll get to spend the whole weekend alone together."

"Ok, I'll do it, but if I start to freak out we leave right away. Ok?"

"That's fine. Now give me a kiss before you go."


The rest of the week was about the same as the previous few days. By the end of our time on Friday I seemed to have everything down pretty well. I was as ready as I would ever be for my weekend as a girl.

I told my parents that I was going camping with some friends for the weekend and said I would be home on Sunday. With my alibi in place I grabbed my backpack and my sleeping bag and headed for Katie's place.

As soon as I arrived I was taken upstairs to her room. I was brought over to sit on the bed where I was presented with a large box wrapped in pink.

"Go ahead, open it."

"What's the special occasion?"

"Your birthday silly. Now I know that its not till the thirteenth but that's when Brett is having his party so I though Britney could get her presents a few days early. So go ahead, open it!"

So I did. I tore into the pink paper and soon had the large box open. Inside was all sorts of girl's stuff. It was mostly all underwear except for a few skirts and tops. Katie told me that she had cleared some drawers out for me to use to store my stuff in. When I opened the indicated drawer I was surprised to find another package wrapped in pink. After a nod from Katie I started to open my second present. Inside I found two pairs of girls jeans and what appeared to be a package of panties in a skin tone colour.

In response to my inquisitive look Katie explained that the flesh coloured panties were 100% Spandex thongs and that I should wear them under my panties to keep everything tucked between my legs, especially when wearing tight pants, like the jeans I just got.

"Ok, why don't you get dressed, you can wear your new stuff or any thing in my closet. While you do that I'm going to run out really quick and pick up another of your presents. I'll he back soon."

I started to get dressed by squirming into a pair of the skin coloured thongs and realized that it was really going to be uncomfortable if I got a boner while wearing these things. Next came a pair of orange bikini panties which covered the thong from view. I had to wriggle into the flared jeans and then pulled on the matching bra and an orange long sleeve top. Next I set myself to the task of doing my hair and make-up. Getting dressed and everything had only take me about 45 minutes this time and I had just barely finished when Katie walked in carrying another pink box.

"Happy Birthday to you! Happy Birthday to you!..." As she sang, she pulled out a small cake covered in pink frosting and a few birthday candles from behind her back. "Happy Birthday dear Britney! Happy Birthday to you! Go ahead and blow out the candles."

I blew out the candles and turned my head to receive a kiss. After a few kisses Katie pulled away and handed me the last present. I started to tare away the paper to reveal a pair of breasts staring back at me through the cellophane window in the front of the box. I sat there for awhile, just staring at the package sitting on my lap until Katie grabbed the box and opened it.

"Take your top and bra off."

Reluctantly I slipped off my top and unhooked my bra and then turned to face Katie. She came towards me holding one of the boobs, an eyeliner pencil and a small bottle of something. I stood there as she placed the form on my chest and traced it with the eyeliner. She then did the same thing on the other side of my chest. I looked on as she proceeded to coat the back of the forms with a gel from the small bottle she had been carrying.

"Ok, you need to hold still for a few minutes."

I inhaled sharply as the cold gel on the forms touched my bare chest. Katie stood in front of me holding the breasts firm against my chest. I leaned in and we kissed. After several minutes we pulled apart and Katie let go of the breast forms. I was amazed as they hung securely from my chest. My transformation had now been taken farther than I ever imaged. I stared at myself in the mirror as I put my bra back on. I was entranced by the way the breasts moved as I got dressed. They looked so real, they felt so natural. As much as the breasts were awkward, they were at the same time very comfortable. As I looked at myself in the mirror I felt a completeness that I never had before.

The day had really been appropriate with all the birthday presents as today had really been the birth of my new self. Before today Britney was simply the name I went by when I was dressed as a girl. At first I had some reservations about the name but over the past week it had taken on an intimacy, it had become who I was. Britney seemed to fit into my self image like the missing piece of a puzzle. I was still Brett, but I felt that I was now complete, as though Britney was a part of myself that had been missing all my life.

My life was definitely going to be different from this point on. I had a lot to think about and a lot of inner confusion to work out. All I knew was that Britney was definitely here to stay.




2004 by Britney. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.