Taylor Enters Beauty Pageant Pt. 02

"Stop staring it's beginning to look like your vain."

"Shut it, Billy." I shoot back teasingly.

"Seriously," he walks up behind me and looks over my shoulder, "I like this one better than the little black dress."

"The little black dress is the hot. It really shows my body." I say looking at that one again.

"The outfit you have on now really shows off your body."

I'm wearing blue denim short shorts and a tight white tank top and I'm barefoot. We took several photos of me in this too and I swipe to that picture. Yeah, this does show all of my body too but still, the little black dress photo is hot.

This morning my mom took me to get this new hair style and I absolutely love it. I loved my long hair but this really makes my face look girly, more feminine and pretty.

Then Billy came over and we talked about what had happened. He said he didn't think I would actually go through with it. That when push came to shove I wouldn't sleep with Rob. I didn't give Billy the details I just told him I was doing what they had all suggested. I also added I wouldn't sleep with Rob again.

Then we began taking pictures because I wanted to post on Instagram and see what kind of reaction I'd get.

We set up a profile then downloaded the three pictures with captions before going out on the back porch to smoke.

"Can I say something that may or may not come out right?"

I giggled at him, "yes! What?"

"You really do look like a girl now. And it suits you."

"Aww, thanks bud. I like this look too. You like my hair now?"

"I said that already."

"Can we kiss again? I like the way you kissed me." I couldn't believe I was being so bold but I had to go for it.

"Taylor! Holy shit! Renee's here."

"No she's not. Her and Paul went to Cedar Mills for a couple days."

"Your mom?"

"C'mon, she's gone for the day?"

"Where did this come from?" He asks looking embarrassed.

"Let me give you a blowjob then."

He laughed at my audacity and it wasn't a comfortable laugh.

"Taylor! Holy shit, you're serious?"

I put my cigarette out and stood up taking his hand in mine and he let me lead him back in the house and down the hall to my room. He never pulled away, no more protesting he just went with it.

We get in the room and I lock the door behind me and walk him to the bed pulling him down on top of me and we begin kissing right away. His hands grope all over my body and I shiver with excitement.

I can feel his manhood on my belly and I want that now. I forcefully roll us over and now I'm on top as I straddle him and our kiss intensifies. Our tongues dancing with each other as his hands grab my ass and he squeezes firmly. I let out a soft whimper of delight and break our kiss.

I move down his torso and kneel between his legs as he we both hurry to get his jeans shorts off and I pull them down his legs. With him naked I stare in awe at the sight of his magnificent cock.

I never really saw Rob's dick when it was hard. I did sneak a peak when we were getting out of bed in the morning but that wasn't nearly like this.

The mushroomed shaped head is pinkish red. The shaft is long and thick with veins running this way and that. He's shaved down there which is a nice surprise.

I reach down with an open hand and touch the soft skin over his hard cock. It's longer than my hand and I reach down with my other and wrap my hand around it as best as I can.

"Mmm," Billy says quietly as he watches.

"Shh, I've never done this before."

"Really?" He seems surprised.

"Really. Just practiced with my sisters toy. Is that okay?" I ask looking him in the eyes.

Billy just smiles and nods.

As I hold his dick I begin to stroke him up and down slowly with both hands. I'm still in awe of seeing his meat like this in my tiny hands.

I've watched lots of porn videos and one in particular always does it for me. This beautiful young brunette girl made love to this man's giant cock with her lips, her tongue and mouth slowly and extremely sensually. I only finished the video once or twice.

I lean down as I held his dick up and I kiss the head softly, sweetly as Billy lets out a long low moan. I keep the head between my lips for a good long time as my tongue swirls around the rim and I feel him wiggle getting anxious with excitement.

Now I moan as my lips slide over the head even more and I'm really getting into this. I go up and down the head slow and purposeful as my tongue slides down the backside of his shaft.

"Ohhh shit..." Billy groans.

I pull back looking up at him as string of my saliva and his precum attach to my lower lip. I wink at him before opening my mouth wide and going back down on him taking an inch, two in my wet mouth. I'm drooling and sucking and bobbing on a few inches of his fat cock nice and slow enjoying every moment of this.

I continue stroking him and my saliva has lubricated his shaft nicely. I have a nice grip with both hands as I take more in my mouth then back up again. Again and again as I moan and whimper over his grinding and grunts I suck his beautiful dick lovingly.

All trace of my masculinity is gone except for my little penis which has soaked my panties and shorts. I'm all girl now as I suck on Billy's big dick whimpering, moaning and keeping eye contact wanting only to please him. In less than a week I lost my virginity as a girl and now I'm sucking my best friends cock wishing I had someone behind me pounding away at my ass. It was safe to say Taylor the boy was no more.

I felt Billy begin to tense up, he was really thrusting upwards and holding my head in place as half his meat was gliding between my lips to the back of my mouth.

"Ohh fuck I'm gonna cum!" He says in deep voice.

I keep my lips wrapped around the shaft as a powerful squirt of his cum shoots into my mouth, the taste is slightly salty and it's thick filling my mouth. Instantly I swallow this as load after load fills my mouth and I struggle to get it all.

I feel some drip out the side of my mouth and down his rod over my hands. And then finally he seems spent as he slumps to the bed breathing hard.

I didn't stop, I sucked him until the end and then licked his shaft, licked my hands and then his balls getting all his sweet cum.

When I was sure I got it all I continue to hold his meat and look up at him smiling sweetly. I played with his cock rubbing it on my face, kissing it and occasionally licking the head.

"First time?"

"Was that okay?" I ask nervously.

"Fuck yeah but that was really your first time?"

I nod sucking the tip again, I couldn't get enough.

A little later we're in the living room, I had to change again because I came in my panties and shorts and my makeup was smeared. I wore a black mini skirt and crop top with sneakers.

I'm sitting so close to Billy as he holds me. I really enjoyed being cuddled by him as we talked for awhile. He asked me if I'd spend the night at his place and I agreed. He had to go help his sister with her car but he'd text me later when he was done.

I went about my day thinking about what had happened with us and I was so excited for later. My mom called and we talked for a little bit and she told me we need to go shopping before Friday, the beginning of the pageant. I'm off Thursday so we could go then.

The day went on and on and Billy never texted. In fact it was fairly late, my mom was even home now from work and he still hadn't texted. I was going to shoot him a text but I didn't want to push him. And of course in my head this was a disaster! He was having second thoughts, maybe he was feeling ashamed as he is a straight guy. Maybe he was embarrassed by me and didn't want anyone to see us together anymore. Whatever the case may be he was really blowing me off tonight.

It wasn't until after midnight when I finally did get a text from him and he apologized saying it took way longer than he originally planned asking if we could do something tomorrow.

Tomorrow came and went and I didn't see Billy. Then it was Thursday and after shopping with my mom I still hadn't seen him.

I resigned to the fact he was not going to do anything else with me as I have gone full sissy on him and he couldn't be around me anymore.

The pageant itself was fun, I got to wear so many beautiful clothes and outfits and parade around on stage all weekend. True to everyone's expectations I did win and I was overjoyed.

I never heard from Billy. Micheal and Patrick came to see me but not Billy.

The day after the pageant I got a congratulations text from Billy but nothing else. I was heartbroken and sad for our friendship. Maybe I pushed too hard to get what I wanted and ruined everything. When I spoke to Renee she said quite frankly, fuck him! He got his rocks off and now just like all guys he's moved on. So should I. Enjoy my new femininity and get myself ready for the state competition.

All the while I totally forgot to look on Instagram and my photos. When I did I was beyond shocked! The photos received thousands of likes, thousands of comments. I was blown away. Even girls on there commented on how pretty I am and the guys, it was so crazy I can't tell you how many asked me to marry them.

The states pageant is three weeks away and I stayed my new femme self and nobody seemed to mind.

One afternoon a couple weeks before the pageant I was scrolling through some new photos I downloaded and I saw this one comment I had seen several times before. It was from a user named TimidTreyman from Cedar Mills. He had commented on every single photo I posted. So I looked him up.

He's an older man yet very handsome with a bald head greying goatee. He wears glasses and has nice blue eyes. In his photos are pictures of him with a beautiful blond girl. Only the girl is just like me. She is a he and she is stunning with an amazing body.

The last few photographs on his profile are of him alone. In one the caption read, breaking up is hard to do.

In each of his comments to me he said he'd love to meet me since we are so close in proximity and sent a link for me and I finally wrote it down and checked it on my laptop. It's of him and his business, he's in the financial world and there's pictures of him all over the world, Paris, London, Tokyo and even Russia.

There's a link there to email him so I did. It was time for me to move on from Billy and see what the world has to offer.

I sent the email half expecting this to be nothing more than an over zealous admirer. I gave him my email and didn't hold my breath.

In less than half an hour he responded to me sending me his phone number if I wanted to chat directly.

At first we texted back and forth before we began talking. His name is Trey and he was a very nice man. He asked me how long I've been doing this and I explained when and why. I also told him I actually prefer the new me and he said he did too but he'd probably like me as my male self too.

We spoke all week and decided to meet that weekend. He offered to put me in a hotel up in Cedar Mills and I accepted.

I spent all night Thursday packing and getting ready and told my mom I was taking a weekend break.

It was time for Taylor to fly.