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 3: Strut Your Stuff!

We spent the rest of the day the way we had spent the morning. However. Around four in the afternoon I had to start my transformation back to being Brett. Amazingly, it only took about a half hour after we got the breast forms unglued from my chest.

It felt weird to be wearing guys clothes again. The most noticeable change was the lack of breasts, but the clothing just felt really odd. I got used to it again quick enough and soon I was headed home.

 

****

 

The next week went by quickly and soon we were only days away from the pageant. I, of course, had been practising over at Katie's place and was feeling rather confidant and comfortable as Britney.

With Katie's help and a little bit of paperwork I was officially in the pageant and we received the official rules and instructions. The pageant was going to be held during a pep rally on Wednesday afternoon and anyone involved with the pageant was excused from their morning classes.

Apparently, the first round was going to be casual wear. Since we knew the judges were going to be looking for who made the most realistic, yet feminine girl, we decided I would be wearing a causal skirt.

Second round was going to be party wear. For that I would be wearing something that showed a little more skin. Something 'sexy' to quote from Katie.

Final round was going to be formal wear. I don't think I really need to explain this one, just your typical prom dress kind of thing.

However, We were informed that if there was a tie between two or more of the contestants, that there would be a swimsuit competition to determine the winner. I just prayed that there wouldn't be a tie. Although it did get me wondering what I would look like in a bikini.

 

 

I didn't have to wonder very long. Thursday night we went shopping to get what I needed for the pageant. I already had casual girls stuff so we went straight to party stuff. Several stores later we had finally agreed on an outfit.

Next was the formal wear. There were only two stores in the mall that sold that kind of stuff, so that's where we went. We both chose the same dress, it was the third one I tried on. After we got that dress we headed for the shoe stores.

We found a pair of sandals that matched the formal first. They were the exact same colour as the dress and had a four inch heel. Next was a pair of heels to go with the party stuff.

Katie picked out a pair for me to try on. They were or pair of platform sandals and the heels on these shoes were massive. They had to be around five to six inches high, which would make me about 6'2" tall. They were a pair of strappy sandals. The straps were made of a shiny pink ribbon that criss-crossed up my legs and tied together just below my Knees. We bought those too.

I figured that we were now done with shopping, once again I was wrong. Katie led me across the mall to a store called 'The Bikini Hut', you can probably guess what they sold there.

Much to my embarrassment I was led around the store and made to choose which suits I liked. I tried to pick a one piece, but Katie put it back and told me to pick two piece suits only. After I was done making my selections. I was stuffed into a changing stall and made to try them all on and model them for Katie. Most of them covered the thong I was wearing to keep myself in place and I wasn't made to model the ones that didn't. We ended up buying two of the bikinis I tried on and then called an end to our shopping trip.

 

****

 

I was sitting on the bus, dressed as a girl, surrounded by bags of girl's stuff that l had just purchased, with my girlfriend sitting beside me. We were holding hands and I was just enjoying the ride when 'he' got on the bus. I froze, my heart stopped beating and I started hyperventilating all at that moment. 'He' was my best friend. His name was Greg and we had know each other since first grade. We knew each other inside and out. We couldn't hide anything from each other. We practically had that thing that twins do. Where they almost seem to read the other's mind. The thought came to my mind to try to hide but before I could even move he had spotted us. He looked shocked as he walked towards us. As he walked the length of the bus to where we were sitting in the back, his eyes never left me for a second. He walked up and sat down across from us, he continue to look me over.

"You look pretty. I knew you were going to be doing the pageant thing, but I never would have guessed you'd look this good as a girl."

I just sat there in shock. That was definitely not the reaction I was expecting.

''Uh... Thanks?" That's about as much as I could come up with at the moment.

"No prob. So what did you buy."

''Nothing." Greg just gave me a look, he wasn't buying it. "Just some stuff for the pageant. That's why I'm dressed like this, I had to try stuff on."

"You seem pretty comfortable like that. How long have you been dressing as a girl?"

He could read me like an open book. "Um... two weeks now."

"Cool, your good at it."

"Gee, thanks Greg." The sarcasm was hard to miss. He just laughed at that.

Finally I was saved by the arrival of the bus at our stop. We said goodbye to Greg and got off the bus.

"Katie, why weren't you saying anything on the bus? I had to try and explain everything to Greg by myself."

"You did fine. Besides. I'm not going to be there to explain things forever. If you decide to be Britney after the pageant, you're going to have to be able to explain that to people. This was a good learning experience for you."

 

 

The next few days flew by and soon I was at Katie's house getting ready for the pageant that afternoon. While Katie went to make some calls, I went and got dressed. I was going to be wearing the outfit I had on for the casual round of the pageant.

After getting dressed I looked into the mirror. I definitely looked like a girl. I was wearing a pink bra and panty set with all three outfits today.

Over that I had on a denim skirt that came to just above my knees. It had a front slit that was about six or seven inches long and had the normal five pockets a pair of jeans would.

I had on two tops with the outfit. First was a long sleeved white top with two pink stripes down each sleeve. Over that I had on a pink babydoll tee with a white roxy logo across the front.

To finish off my outfit I had on a pair of white ankle socks and a pair of girl's sketchers in pink and white. Once I put my hair up in a ponytail and grabbed the other clothes I would need, Katie and I left and headed to the school.

 

 

When we arrived at school we checked in with the people running the pageant and were then ushered into an area behind the stage they had set up in the gymnasium. The room was sectioned off by several curtains into about twenty changing areas. Katie and I were led over to one that had a piece of paper with our names on it taped on the curtain. We went in and hung up our other clothes and stuff on the little hooks in there and laid out my make-up and hair stuff on the desk. As I was already dressed and made-up, we sat and talked while the other contestants got ready.

After everyone had arrived, one of the teachers running the pageant took us out onto the stage. Since we had gone in the back room, they had set up a runway on the front of the stage. The next twenty minutes were spent instructing us as to where we supposed to stand, walk, enter and exit the stage and having us practice doing each of these things.

Eventually, once they were satisfied that we knew what we were doing, we were sent into the changing area in the back before the other students were filed into the gym for the pep rally. All the girls in the room were busy making final touches on the boy's feminine appearances. As I was already dressed and had my make-up and hair done, I thought that Katie and I would just sit back and watch all the commotion. that's about the times that Katie came out from our little booth carrying a pair of tweezers.

"What are those for?" I asked the question hesitantly, knowing that I didn't want to hear the answer.

"We need to work on your eyebrows a bit."

"Why?"

"Because they're too thick and don't look right on a girl. Besides, I'm not going to do anything drastic with them. Just thin them a bit and add a little more of an arch. They'll make you look even prettier... and I know you like to look pretty." The last part was barely a whisper.

"I'll let you, but you have to make sure that they'd still look normal on a guy. Deal?"

"Deal, now hold still."

So I spent the next ten minutes enduring the torture of having my eyebrows yanked out by the roots, one by one. I did have to admit when I looked in the mirror that I liked how they looked. They made me look more like a girl, but not so overly feminine that they would look out of place when I was dressed as a guy.

I had a chance to sit down and take a look at the other guys in the pageant. As I scanned the room I realized that most of the guys had absolutely no chance of winning. However, there were about three other boys I would have easily mistaken as girls had I met them on the street. I was actually going to have some competition for this thing.

 

 

"Can I have everyone's attention please. We're going to start the first round of the pageant in about five minutes. Please form or line over near the stairs, in the order we explained earlier. When you hear your name called come up the stairs, across to and down the runway. When you get to the end of the runway just pose for everyone, do the turn we practised and walk back and take your place on the stage. Any questions?" There weren't any.

All of a sudden I was really nervous. I just stood there in line, clinging to Katie's hand for dear life. She squeezed my hand back and whispered into my ear, "I love you. You're going to do great.'' I really needed to hear that at that point.

As we stood there in line, we could hear the pep rally get started and the 'student activities chairman' announce that the first round of the pageant would start.

The first guy was called on stage. The crowd went silent for a few seconds and then burst into a mixture of applause, laughter and catcalls. It was almost deafening. One by one each of us was called up on stage until it was my turn.

"...and our next lovely young lady is Britney McMaster!" reluctantly I let go of Katie's hand and walked up on stage. Katie patted my butt as I ascended the steps and told me to smile. I smiled.

As I made my way to the runway my eyes adjusted to the bright spot lights that they had fixed on me as I made my entrance. I stared out into the crowd and spotted a group of my friends at the end of the runway. Greg was looking me right in the eye and gave me a thumbs up. It wasn't until I reached the runway that I realized that nobody was laughing at me like they had at the others. A lot of the kids in the crowd just had a look of awe as they looked me. I even heard one of the kids say to another, 'he actually looks like a girl.' I wasn't sure if I liked hearing that or not.

I walked to the end of the runway and did a couple poses that I thought a girl might make and then turned and made my way back to the stage. As I took my place in line I looked over at the judges and saw them looking right back at me. I just smiled back at them and mentally told myself to calm down, for about the thousandth time.

After about ten more minutes every one of us had made our way up on stage and were all now standing in line. A few minutes after that one of the judges handed a piece of paper to the MC and she walked over to the microphone.

"Well, our panel of judges has made their first cut and we'll now announce those who have been eliminated and ask that they form a line here behind me."

As she read the names, the boys whose names were called formed a line as directed. I realized at that point how the judges had made their decision so quickly. All of the ones being eliminated looked like guys in dresses. After a round of applause they we directed off the stage and the rest of us were brought forward to receive our own applause.

As soon as I got off stage I was quickly whisked into our little changing area by Katie. Within only a few minutes I was sitting there in bra and panties as my hair was being tightly wound onto hot rollers and then thoroughly sprayed with some kind of hair product.

We had about fifteen minutes to get changed while they did their other pep rally stuff and then if would be time for round two.

While we were waiting for my hair to be done, I got dressed in my next outfit of the day. First was some sort of oily stuff that really wade my legs shine. Next was the skirt. It was really short and really flared skirt in white and was made of a really thin fabric. I was just glad I wouldn't be outside in this. It barely even covered my panties as it was. If a strong breeze caught it, that skirt would have been around my waist as I gave everyone watching a free show.

After I had on the skirt, Katie helped me remove the straps from my bra and then I wriggled into a tight pink tube top. Even for a tube top this was really low cut and showed a lot of cleavage. The bottom of the top was cut in a 'V' shape which seemed to point at my bellybutton.

Once I had all that on it was time to finish my hair. We had about five more minutes to finish getting ready. One can of hair spray later and my hair was bouncing around my shoulders in a mass of shimmering curls. Without even pausing, Katie was busy re-doing my make-up.

The shoes were last. They were the pair of white platform sandals. I was really good at walking in them after all the hours of practice Katie had forced me to do. The platforms were five inches under my heel and two and a half inches under my toes. They made my legs look great. The only problem was that I was 6'2" in these shoes, not exactly a normal height for a girl. It took me a little while to get the pink straps properly wound around my calves and tied in little bows on the outside of my legs. After a few failed attempts, I realized it was impossible to put on the shoes without flashing my panties in that short skirt.

I barely had them on when they started to herd us back out on stage. It was the same as the first time. Wait for my name to be called, then head out on stage. This time my arrival on stage was met with some applause, catcalls and a few audible gasps. It occurred to me as I began my walk down the runway. With all the kids sitting on the gym floor and myself up on stage in such a short skirt, they were going to be able to see right up it. I was right.

As I made my way down the runway and back again, I was overwhelmed with comments about my panties. Not to mention an increase in the amount of catcalls being directed at me. I also heard several people, mostly girls, make comments about my boobs. Soon however, I was back on the normal stage, watching the rest of the boys make their way on stage.

This time we were each bought over to stand in front of the judges. Once there, they would announce either to go down and sit with the other students (aka ''you're cut") or to go back stage and get ready for round three. Eventually I was first in line and went to take my turn in front of the judges. I mustered ever ounce of courage I had and stepped up to the microphone smiling.

"And your name is...?"

"Hi! My name is Britney, but my friends call me Brit!" I had used the most girlie voice I could and it was practically oozing with cute.

"You must have a lot of friends, you're a very pretty girl."

For some unknown reason, I blushed a little, smiled and then did a curtsey for the judge and said, ''thank you! I wish I could be this pretty all the time." That got some comments from the audience.

"Well, I don't see any reason why you wouldn't look that pretty all the time."

This was the longest any of the judges had talked to any of the others. Mind you, all of the ones who had been before me had been cut, so I took this as a good sign.

"My parents don't approve of me dressing like this. Dad would ground my for life if he saw me right now"

"I'm sure they wouldn't mind too much. This is a beauty pageant after all. Besides, I'm sure you'd look pretty no matter what you were wearing. I bet you would still be prettier than most of the girls here if your Dad made you dress as a boy all the time." That got a blush from me and some laughter from everyone else.

"Maybe," was my timid reply.

"Well, we're glad to have such a beautiful young lady in our pageant. So why don't you head to the back and get ready for the next round." I merely nodded my head and headed to the back to get ready.

 

****

 

"You were great out there! But what was with the curtsey?"

"I have no idea. I just did it without even thinking."

"Maybe you're more of a girl than you thought. So did you mean what you said out there?"

"Huh?"

"About wanting to look pretty all the time."

"I dunno, sort of I guess. I like being a boy though, so not all the time."

"The judge said that you'd be pretty when dressed as a guy too, remember? I think she's right."

"What's that supposed to mean?"

"It means that I think you're pretty. Is there something wrong with that?"

"No."

"Good. Lets go get you dressed then."

I was quickly stripped back down to my bra and panties and sat down in front of Katie. She started on my hair first. I would be keeping the curls, but they would mostly be pinned up on the back of my head. I sat there while Katie worked away on my hair and tried to put together the puzzle that was my feelings. My life had been so much easier before I started dressing like a girl. I decided I was going to have to take a break from all this as soon as the pageant was over.

"What do you think?"

The question pulled me back to reality and I looked in the mirror. Damn, I looked good. The curls were all now piled up on the back of my head, except for a few that hung down around me bare shoulders.

"It looks great Katie. I just wish it was on you, not me."

She took my chin in her hand and turned me to face her. "Well I think it makes you look beautiful." She leaned in for a kiss and I eagerly met her embrace. We had been going at it for several minutes when Rebekah walked into our little booth and made herself known with her comment, ''cool, lesbians." Katie and I booth gave her a look the could kill.

Rebekah was a mutual friend of ours. She was part of the group of girls that Katie hung out with and was probably Katie's best friend. Needless to say, Katie was closer friends with her than I was. It was about then that I realized that I was sitting there in just my underwear. I could feel myself blushing profusely as I tried in vain to cover myself up with just my hands.

"Look Katie, she's blushing."

"Katie, can I talk to you for a minute... in private." I looked up at Rebekah and she left. "Why is she here?"

"I asked her to come help me do your make-up. She's better at that than I am."

"But why didn't you tell me she was coming?"

"Because I didn't think it would be this big problem with you. What's the matter anyway?"

"My problem is that I'm sitting here in nothing but girls underwear and I don't want people seeing me like this."

"When did you become so modest?"

"Well its different if its only me and you."

"Well give me a sec and I'll go and try to work this out, ok?"

"ok"

 

****

 

The solution was a big sheet wrapped around me and tied behind my neck. I have no idea where Katie got it, but I sat there happily covered up as Rebekah went to work on my face. It took what seemed like hours, but finally she was finished. I turned to look in the mirror but was quickly stopped by Katie.

"Not yet babe, not until you're dressed. Besides, we still have to do your nails."

"My nails?"

Rebekah grinned and held up a package of fake nails. "You get these." I must have made a face because she said, "relax, they're really easy to take off"

Without another word they started on my nails. The fake nails where about a quarter of an inch past the end of my fingers. They had a squared tip and I had seen a lot of girls at school who had their nails done that way. They were also painted in a style that I would later learn was called a french manicure. Soon all ten of them were glued on and I thought they looked really good. Rebekah gave me a hug, wished me luck and then left. It was finally time for me to get dressed.

Katie brought over the dress, hung it up and unzipped the plastic cover. The dress was gorgeous. I was still staring at the dress when Katie came over to me carrying this pink... thing. I knew it was some kind underwear, as it matched my bra and parties perfectly. She held it up, grinned and beckoned for me to stand up.

"What is that thing?"

"It's a garterbelt silly, it's what's going to hold up your stockings. Come here and I'll show you how to put it on."

There was some fumbling due to my now long nails and the unfamiliarity of the garterbelt, but I finally got it on. Katie handed me a pair of stockings to fumble with next. They weren't nearly as difficult. They went on just like pantyhose, only one leg at a time. They were super sheer and really made my legs shimmer. When I tried to attach them to the garters I realized they were more difficult to wear than I had first thought.

Katie ended up attaching my stockings to the garters and once satisfied with them, went to get the dress. The dress was strapless and also in pink. The bodice was practically a corset and laced up in back. It hugged my figure and showed off every curve I had from my boobs down to my hips, where it then billowed out into a very full skirt, due to the countless layers of petticoats underneath.

I slipped into the dress and held my breath as the pink laces were pulled tight and tied in a bow at the small of my back. After straightening the skirt I took a seat and held up the skirt as best I could while Katie strapped the pink heels onto my feet. Next came jewellery. I wore a pair of clip on rhinestone earrings, a few rings, a matching rhinestone bracelet and a rhinestone choker necklace. Everything was ready so I turned around and for the first time, looked in the mirror.

I was beautiful. I also looked about 5 years older than I really was. The make-up was really dramatic and looked fantastic with the dress. I wondered where Rebekah had learned to do make-up like that. I already described the dress, but it looked amazing. Along the neckline of the dress was a row of shimmering rhinestones that really drew attention to the cleavage I was showing. Over the next few years I would spend progressively more of my time as Britney, but I have never looked as beautiful as I did in that dress that day.

My name was called shortly thereafter and I headed on stage after giving Katie a nice soft hug, from which I didn't want to let go. Again, it was simply a repeat of the first two rounds. Go on stage, walk down runway, walk back to stage. Not exactly difficult. That is, until I reached the end of the runway.

There was Greg, sitting in the same spot he was in before. He was still smiling at me and watching me like a hawk just like before. The difference was that now Rebekah was sitting next to him and he was holding a bouquet of flowers in his lap. I hesitantly walked to the end or the runway, where on my arrival Greg jumped up on the end of the runway.

"Hey there. You look great."

"Um... thanks."

"No problem. Uh, these are for you." He stepped forward and gave me the flowers and then leaned in close to me and whispered in my ear, ''they're from Katie." I smiled at that as he stepped back and bowed to me. While trying to hold onto the bouquet, I held my skirt and curtsied to him before heading back to the stage.

Once all of us were on stage the judges took a few minutes and then handed the MC the results. She walked over to the microphone and opened the envelope and pulled out a piece of paper.

"As you all know, this was supposed to be the final round. However, because all of our contestants have made such beautiful young women, our judges can't decide on a winner just yet. They've narrowed it down to three of these beautiful girls. I'll call their names and then we'll dismiss them to go get ready for round four."

That was the point where I was torn. I really wanted to win this thing, for Katie and for myself. But at the same time I really didn't want to be part of the swimsuit round. I'd never be able to live that down. I just shut my eyes and hoped they didn't call my name.

"Ok, since it was a tie we'll call our finalists up in alphabetical order. Our first girl is Amy Bailey." A pretty young girl walked forward. She looked way too young to even be going to high school. Her dress didn't do much to help her image. It was a little girl's party dress in a pale yellow and was abundantly adorned with ribbons and lace. She definitely looked like a girl though.

"Ok, our second finalist is Britney McMaster." Damn. I made my way to the front of the stage and took my place next to Amy. "And last but not least is Natalie Myers." She made her way to the front. She was about 5' 8" and was wearing a dress similar to mine. The difference was that mine was pink and strapless while hers was a kind of of a lilac colour and had sheer sleeves.

"Well girls, why don't you head to the back and get your swimsuits on. You've got about 10 minutes to change." With that said we all turned and hustled back stage.

 

****

 

"Uh... thanks for the flowers. Nobody's ever given me flowers before."

"You're welcome babe. Besides, what kinda person would I be if I didn't ever give my girlfriend flowers, especially on her big day. Now hurry up and get undressed."

I managed to get out of the dress and shoes but needed some help with the garters, as I couldn't reach the ones in back. After receiving some help from Katie, I was soon stripped down to the flesh coloured thong.

"Here, put this on, hurry."

I took the pink bikini from Katie, stepped into the bottoms and slid them up my legs. They didn't cover much more than the thong did. Next was the top. I needed to get Katie's help to tie the top in back, but I was able to tie the the other straps behind my neck by myself. I looked good in that bikini. It was made from a wet-look material in baby pink and I was amazed that I had the figure required to wear it.

Almost as soon as I was dressed I was sat down in a chair while Katie let my hair back down. I was then handed a pair of pink thong sandals and a pair of girls sunglasses. After I had the sunglasses on, Katie moved them up on my head like a hair band. We came out from the booth and were soon joined by the other two boys and the girls who were helping them. One of the teachers running the pageant came in the back and told us we had two minutes before they would start the final round.

"I think two minutes is just enough time."

Confused, I turned to Katie and asked, "just enough time for what?"

"This," was all she said as she wrapped her arms around my waist and gave me a deep, lingering kiss that probably did last all two of those minutes. I had to brake the embrace prematurely due to the pain of getting arouse while tucked away in the tight panties. We stood there intertwined with each other until I was called back out on stage.

This time on stage was different. The crowd was practically silent. I did the standard walk down the runway and back without any further embarrassment. It was announced that the judges still couldn't make a decision and that the students would get to vote.

This is how it would work. Each of us would in turn walk to the front of the stage and whoever got the loudest applause would be the winner.

Amy went first. Even in a bikini, she looked like a preteen girl. She got a lot of applause from freshman area of the crowd. I was next and started towards the front of the stage. The noise erupted as I arrived at the edge of the stage. I actually could win this. For some reason I struck a pose I had seen in swimsuit issue of Sports Illustrated. It had looked sexy in the magazine and I hoped I could pull off that same look. From the crowd's reaction I guess I did. I blew a kiss to Katie, who had taken a seat with the rest of our friends and then retreated to my place at the rear of the stage. Natalie headed to the front to take my spot and got a very loud outburst of noise from the senior's section. It was definitely going to be close. The judges would have the final say in who got the most applause. The crowd settled down and and the judges quickly delivered their verdict to the MC to announce.

"Third place goes to Amy Bailey." Amy went forward and received a pink sash and then was directed to stand off to the side.

"And in second is Natalie Myers." As Natalie headed over to receive her sash it finally dawned on me... I had won!

"And the winner of the Miss Octoberfest Pageant is the lovely miss Britney McMaster." I hesitantly stepped froward and received a sash as well as another bouquet and a rather cheap looking tiara replaced the glasses on my head.

I had actually won. However, now the pageant was over and I no longer would have a good excuse the be Britney.

  

  

  

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