Taylor Enters Beauty Pageant

I've been working on this for sometime now. It's purely fiction and all for my entertainment that I'd like to share. If you don't like it there's no reason to be cruel or mean. Just scroll on to something else. Everyone else just enjoy. There's more cumming! MUWAH

"I'm not doing that! No way no how forget it!" I had said at the time, over and over again and yet there I was doing exactly what I said I wouldn't. That was the day I became a girl in a beauty pageant for boys as girls. My friends had convinced me that I would not only win the counties pageant but that I could definitely win at states too.

At the time I didn't see it, I thought there was no way I could pass myself off as a girl but as I sat at a vanity desk while Daisy did my makeup and talking the whole time explaining what she's doing and how I had to this myself, I admitted maybe they're right.

I was actually very pretty as a girl. I have the hair; dark, shiny and wavy brown and below my shoulders. And I have what my sister always calls 'androgynous' features, high soft cheek bones, full pouty lips and cute button nose along with big brown eyes. I'm slight of build, thin and not very masculine at all. Long thin arms attached to a thin frame, flat belly and tiny waist and unbelievable girlish hips and an incredible cute bubble butt. I'm even blessed with long sexy legs.

The legs I've always noticed but until the week before the pageant I hadn't seen the rest of me as feminine until Daisy and Renee helped transform me into one.

This pageant is a really a big deal where I come from and everyone really gets into it. Everyone except the fathers I believe. My dad left us when we were very young so it was just me, my mom and sister. And they were both very excited for me.

My sister Renee said I have to be convincing, that I need to live the part, be a girl until the pageant. This way the judges are sold on my commitment to this. I argued against this as I do have a day job and there's no way I'm working the local convenience store as a girl.

Both Daisy and my mother starting name dropping, telling me about all the other boys in the past that did just this and won or was runner up. I knew a few of the guys they mentioned and they were very passable and convincing as girls. I just assumed they were gay and loved it. As it turned out one guy in particular stayed the part even though he didn't win the pageant. He did win in another way, he ran off with a very rich guy and they're still together, so I hear.

That's all well and good for him but I still didn't want to go to work with makeup on. And that's not even close to what they are telling me to do. We hadn't even gotten to the dressing up yet.

It began easily enough by knowing my sizes, I'm either a size six or petite. My shoe size (in ladies shoes that is) is a 7 in some 8 in others. My mom already knew this and really spent more than she had for a wardrobe for me. And my sister donated some things she no longer wore.

I had already showered and shaved and while I sat there listening to Renee and Daisy telling me what I had to do to get ready I thought this is really a bad idea. Why did I let them talk me into this?

They had an assortment of panties for men called gaffs, basically these are designed to hide my junk painlessly. They also had various bras and bralettes. This included breast forms.

I had to try on everything to make sure it fit and to see what I looked best in, according to them. Short shorts, very short and very tight. Tops of every style, skirts from mini to full length and dresses. They had several dresses that I would need for the pageant that were like prom dresses and these were pretty amazing.

As I changed into outfit after outfit and looked at the pictures they were taking and reflected on them I couldn't believe how beautiful I really looked. In some of those more provocative outfits I was down right sexy. Trying on and changing outfit after outfit took the entire day. My mom even made a great meal for us and I ate while wearing a floral summer dress.

They convinced me that I needed to be a girl from now on in order to win the state pageant.

The big deal for my mom is the prize money, it would set me up big time. The county pageant prize money is good but the state pageant was twenty five grand! That's a lot of money for a small town boy, er, girl like me.

That night I slept in real panties and a t shirt and woke up feeling extremely horny. Horny enough to get myself off looking at my legs and feeling myself up. After a shower and quick shave I looked at what I had to wear and ya know what, there was nothing there that wouldn't make me look casual, just girly clothes that I'll look the part wearing.

I almost backed out of this whole thing right then and there but the idea of all that money spurred me on to go through with it.

I chose a white halter top, skinny jeans and plain white sneakers. After applying my makeup and brushing out my hair I dressed and in a way it felt good. Especially with the jeans and panties holding in my privates, that felt sexy. I still couldn't get over how hot my ass looks in anything.

My mom wasn't home but Renee was and offered to give me a ride to work. She said I looked like the sweet girl next door. She also told me not to worry about Mr. Brogan, he knew I had entered the pageant. That meant everyone I knew was aware of it.

I had been extremely nervous going in but Mr. Brogan, a slightly overweight balding guy was very nice and accepting of me. And since it was just him and I for the first four hours of my shift I was okay with it. Even when people I knew came in, they were all very friendly with me and liked this look on me.

Then Micheal D'Marcus came in for cigarettes and he got all shy and quiet when he approached the counter. I've known Mike most of my life and this could have been the turning point for me in changing my mind again and ending it now. But it was the way he looked at me and his shyness that really turned me on and I loved it. He's always been the type of guy to shut down and get shy around pretty girls and now he was doing that with me.

"Hey Mike." I say as I rang up his cigarettes.

"Hey Taylor."

"What? No opinion on how I look?" I push.

"You look uh, you look nice." He says avoiding eye contact.

"Seriously? Nice? Don't I look pretty?"

"Don't push it Taylor." He says smiling at me before heading for the door.

"But you know I do!" I say as he's leaving. He just gives me a glance and a smile and leaves.

I have two other buddies that knew I was doing this and Patrick and I have been texting. He wanted the whole story on how it felt being a girl. We're people being nice to me or making fun of me. Did I like the attention? Has Billy seen me yet?

Billy, my best friend in the whole world was in on the whole conversation about me entering from the start. And yet I haven't seen him or heard from him. He'll turn up soon enough, I was sure about that.

Around eleven Trish and Carl came in and Trish just loved how I looked and immediately began talking to me like I was actually a girl. Yeah, we were having a girl talk. Carl, a nice guy that works hard and minds his own business kept staring at me. Trish kept saying he thinks the new girl is hot. I forgot she was talking about me.

All in all it was a good day. I was hit on so many times I got bored with it. The guys that knew me seemed awkward and the bolder ones actually talked to me like I really was the new girl in town.

It's nearing the end of my shift and I called my mom to see if she'd pick me up. She said Billy was coming to get me.

Great.

I see his silver Honda parked out front and after clocking out for the day I head to his car.

Billy and I are complete opposites, he's a big guy and I'm not. He's the ladies man and I'm not. He's athletic, I'm smart. He's usually very funny, I'm more of a smartass. He's very clean cut and all american, definitely not me.

I climb in and he's looking at me sideways with a slight grin before pulling out and heading home.

"I didn't think you'd go through with it."

"Well, that's what ya get for thinking."

"And how was work looking like this?"

"Weird."

He just nods.

"Mike came in." I told him.

"I know. He told me. I think he likes the new you."

"Do you?"

"It's still you, you just look different." He says.

"It's for the money Billy. You do realize that don't you?"

"Of course, Renee told me."

"Good. Where are you going?" I say as he makes a left when he should've gone straight ahead.

"The park. Unless you don't want to."

When we go to the park we chill by the lake and smoke weed, talk about nothing and crack each other up.

At first that seemed to be exactly what we were doing. We had a our usual banter and laughed it up as we sat on a picnic table scarred with people's names carved in it. My name is on there as is Billy's.

Then he got all serious on me. "Do you know Nick Reardon?" He asked me.

"The guy at the bank." I nod.

"Yeah. That one."

"Yeah but not personally. What about him?" I ask.

"You know he won this a few years ago?"

"Wasn't that like ten years ago?"

"Whatever the point is he won and he doesn't look anything like a girl."

"Now, but if I remember he did pull it off."

Billy nods as he throws a rock in the lake and we watch as the ripples spread out. "That year was a tough competition. Lots a passable and pretty contestants."

"I don't remember that."

He ran off a few names of guys that no longer live in the area and some that do. Then I remembered that pageant, there were a lot of pretty girls in it. Some years have been like that, very pretty very passable guys as girls. Some years, not so much.

"Taylor, this year there'll be some guys in it that do this all the time. Kristen Marks, ya know him?"

I nod, Kristen is actually a guy that's been crossdressing forever.

"Gary what his name-"

"Trimball?" I say.

"Yeah him."

Gary is also a transgender and quite pretty.

"So?" I ask. "You saying I'll lose."

"No, I'm not saying that. I'm saying the competition is tough this year."

"Nothing wrong with that." I tell him.

He takes a deep breath and looks at me serious. "I'd be bummed for you if you lost after going through all of this ya know, to lose to those guys."

"Me too but I thought you guys said I'd win easily."

"I thought so too until I found out they were in it."

I just nod and wondered if this was over before it began. So I said this out loud and Billy came over and sat down next to me.

"It doesn't have to be."

"What's that mean?"

"Do you know Rob Fisher?"

I shook my head.

"He's the head judge in this year's pageant. And from what I hear he's also into boys dressed as girls."

Billy is staring at me and it hit me.

"What're you saying?" I ask.

"Nick Reardon slept with one of the judges that year and won. Maybe, just maybe-"

I stood up, "are you telling me to fuck this guy to win?!"

"Well it wouldn't be like that?"

"You mean let him fuck me?!!"

"Calm down."

"No! Take me home." And I went silent with anger. How dare my best friend in the whole world suggest I also go gay to win this thing. That's it! It's over! I'm going back to my normal self and forgetting this ever happened.

As we drove back to my house in an awkward silence I tried to grasp what he was actually saying. Yes I was turned on by how guys looked at me. I never received attention from girls like that. But could I really fool around with a guy? I'd never be able to show my face again. Or ever get another girlfriend. Not that I had had many of those in the first place.

"Can I tell you something?" He says as we pull down my street.

"What?" I say angrily.

"This wasn't my idea."

I look over at him, "who's idea was it?" I don't know why I asked, I already knew.

"You gotta know Taylor she wants nothing but the best for you! She's been stuck in this town her whole life. And now she's watching Renee go down the same path. Neither of them want that for you too."

"Maybe I do."

"No you don't! Don't even bother telling yourself that. You want to go to college. You want a life that's not here." He shook his head as we parked out front of my house. "I know you better than your own mother and all we've ever talked about is the day we can get outta here. And here's your golden ticket and you're gonna give it away."

"So you think me going gay is the right thing to do?" I ask still a bit snooty.

"I see you as Taylor, that's it."

I sat there a while longer before getting out and heading inside.

The tension in the house that night was fairly thick. I stayed in my room alone playing video games while my mom and sister and her boyfriend Paul waited for me to come out. I had told them if I came out still dressed up then I would try their suggestion. If I came out as myself again then they all knew it was over.

I sent Billy a text, 'can we go back to the park?'

'When?'

'Now.'

'Okay.'

I took a deep breath then looked at my new wardrobe. I had made up my mind. I grabbed a pair of regular satin and lace panties and matching bra and changed. Then I pulled on a black tank top with goth patterns. After I had this on I slipped on tight black short shorts finished off with black Doc Martin ankle boots. I checked my makeup and hair then waited on the text from Billy.

When I left my room and walked down the hall into the living room my mom looks up at me and a slight smile crosses her pretty face. She gets up and walks over to me and gives me a long loving hug.

She holds me out at arms length and looks me over, "you look cute. Where are you going?"

"Out." And I left.

Billy and had sat in silence now for an uncomfortable long time as we passed a joint and bottle of whiskey back and forth. Finally I got up and went to the water looking out at it. Then I walked back and stood in front of him a few feet away.

"I have no clue how to go about this."

"Luckily for you he will."

"Well no shit. But I don't know what he looks like or how to even make myself available to him."

"I don't either but I do know he works at Staples, he's the photography manager or something." Billy tells me.

Staples is in Merchantville which is about ten miles from Avondale where we live.

"He doesn't live here?" I ask.

"No. I only know because your mom knows."

I cross my arms and stand there not sure what I'm supposed to do about this. "So what do you think he'll want me to do?"

"If I were him, anything a girl does."

"Really?" I did like how Billy was looking at me. Maybe I am gay because I was now getting butterflies in my belly.

"Would I have to kiss him? You know, like a girl does?"

He nods, "probably..."

"And does it have to be convincing?"

"I would think so."

"And everything else too?"

"Yeah..."

"How do I kiss like a girl?"

He cleared his throat and looked a bit uneasy then said, "well, looking like you do I doubt it would be hard. Just be the girl in a kiss."

I'm definitely gay because I wanted nothing more at that moment than to kiss Billy. So I took a step closer to him and he just stared at me.

"Will you help me practice?" I ask as sweetly and as femininely possible.

"Are you sure?" He asks looking scared.

"Never mind. I know that's asking too much."

"Well wait, are you sure you want me to help?"

Is he in?! "Yes." I take a step even closer.

"Well, come here then."

I close the distance and stand between his legs as he sits atop the picnic table. I put my hands on his knees and step in closer as our bodies touch. His hands grab my ass and he whispers in my ear, "I've wanted to touch this ass."

"I think I've wanted you to too."

I feel his breath on my cheek and I turn his face to face me. Then the time of truth is at hand. I lean in and our lips meet. My whole body tingles as we kiss long and tender. I let out a soft moan.

Then his tongue parts my lips and he's really kissing me. I wrap my arms over his broad shoulders and moan even more.

His taste, his tongue dancing with mine is so wonderful. I've never been kissed like this before. His hands have a firm hold of my ass as he pulls me in tighter.

I let myself just relax and fall into his arms and our kiss deepens. I moaning now and really into this.

At last I break away and lean back as he just holds me. "How was that?"

"It'll need some work." He teased.

I smack his arm and lean back in as we kiss again and again. I felt how good our kiss was now, his cock was hard in the thigh of his jeans.

Billy and I had a make out session for quite some time that night and he didn't push doing anything else.

That night in bed I played with myself because I was so turned on by the events from earlier and I wanted more. Maybe I am gay, maybe this is who I really am. I didn't care now what anyone thought, I am going to win this pageant being the best girl I can be!

The next day, Friday is one week from the beginning of this year's pageant and I spent most of that day learning to do my own makeup and hair. Walking in heels like a lady with my sister even showing me the catwalk. Swinging the hips while keeping my upper body straight and level. Mom and Renee both agreed my voice didn't need any work as I have a soft raspy tone that's very effeminate anyway.

I did work that night and wore black leggings and a cute pink crop top. I really enjoyed the attention and embraced my role as a twenty one year old young lady. While most people are accepting of me there are the haters but they are few and far between.

By the time I got home after eleven that night Billy had texted me and told me a little more about the Rob Fisher guy. Apparently he goes to a gay bar in Merchantville fairly often. He said this would be the best opportunity to meet him. Maybe we could go Saturday night. So I summoned up all my courage and agreed.

Saturday was an early work day 7-3 and afterwards Billy picked me up and took me home. I talked with my sister after Billy left and she gave me advice on how to handle myself and what to expect.

Around 8 I took a shower, shaved everywhere and even did a douche. I watched lots of YouTube the past few days on crossdresser sex and other things related to crossdressing. Next I did my makeup and hair then my nails and toenails before choosing an outfit.

A simple black mini skirt, very mini showing lots of legs and if I move the right (or wrong) way, a little bit of butt cheek. Along with a cute pink three button up cropped top sweater with long sleeves and very light. Underneath I wore black lace panties and matching bra with breast forms and cute white tennis shoes.

I made Billy wait as touched up my makeup and hair then left for my first night at a bar as a girl.

"Wow." Billy says as I climb in his car.

"Eyes forward mister."

"That ain't gonna be easy." He says as we head out.

We're ten minutes away and I ask him how the heck am I supposed to know who he is.

"Well he knows who you are. When you signed up your sister downloaded before and after pictures of you. So maybe he'll find you."

The bar is called The Kingside Lounge and it's just outside of town. After parking and triple checking how I look we head inside.

It's a fairly busy night and there is a very mixed crowd. We made our way to the bar, ordered drinks and found a table to claim as ours.

One drink led to two and then another. Yes I was hit on but mostly by women. One girl in particular was gorgeous but after talking to her for a few minutes she realized I was a guy and her interest seemed to wane.

When I had to use the bathroom I used the ladies room. Then Billy went to use the men's room and thats when a clean cut brown haired tall thin man put a shot glass on the table.

"I know you." He says as he stands there looking me over.