Taylor Enters Beauty Pageant

"Oh-kay." I say smiling back a little nervous.

"Taylor Sherman, right?"

I just nod.

"I'm Rob, Rob Fisher." H extends his hand to me.

"Hello." I shake his hand.

"Guess you'd like to know how I know you." He's still holding my hand.

I have to play naive, "yes."

"You entered this years beauty pageant, didn't you?"

"I did, yes."

"Well I'm one of the judges and so far you're winning." Still has my hand.

"Oh really?"

"Oh really. I saw your before and after pictures and I really couldn't wait to see you on stage."

"Really?"

"Really. And can I say something. I hope I don't offend you but,"

"But?" I ask.

"It doesn't take much for you to make the switch from boy to the sexy little girl sitting here."

"Well thank you."

"No, thank you." He finally let my hand go. "Is the. If guy your boyfriend?"

"No, he's my friend."

"Well that's good to know. Why are you here?"

"I'm having a drink."

"I see that by why here? At a gay bar."

"Oh, well it seems safer than going to a straight bar and..." I let that hang there a moment before finishing, "and I am just exploring my feminine side."

"Would you like help with that?" He asks boldly.

"Do you smoke?" I ask.

"I do."

"Have any?"

"Not here, wanna go smoke some? I live five minutes from here." His fingers are running up my bare thigh. I feel my little cock twitching in my panties. This was the same feeling I had when Billy and I were making out.

"Sure, why not. But I have to text my friend and let him know."

"No problem."

I quickly text Billy letting him know what's going on. He asks if I want him to stay close by but I tell him he'll get me an Uber. He says he'll stick around until he knows I'm okay. Then he says we'll talk later and be safe.

I really felt like a girl with him as we left the bar, first he pulled my chair out for me then we walked out with his hand on the small of my back. As we stood out front he was really checking me out. "You really are a sexy little thing, do you know that?"

"Thank you. It's always nice to hear."

In the Uber I sat close to him and let his hand feel up my legs in a subtle but obvious way.

He lives in a townhouse and it's very nice, neat and tidy. Once we are there I do accept a glass of wine and we sit in his kitchen/dining room on tall stools at the breakfast bar.

He excuses himself to get the weed and I look around. It's a cozy place with a second floor, looks like he's very neat and tidy.

I like the way he touches me and he's not a bad looking guy, which helps. I also like the way I feel.

After he came back and we smoked he's sitting very close to me, his legs apart on either side of me.

"Can I tell you how lucky I am right now?" He says rubbing the outside of my thigh.

"Can I tell you something?"

"You can tell me anything."

I took a deep breath then say, "the only thing I've ever down with a guy is kiss. So I'm a little nervous."

"There's no need to be nervous. We don't have to do anything if you're uncomfortable."

"But I want to." I say putting my hand on his looking in his brown eyes.

He pulls me in close and our lips meet and his tongue drives right between my lips and we make out for a few hot moments. I even stand up and into his arms, and feel his hard dick on my side.

"I would like to be your first." He says.

"Okay." I say quietly and nervously. I remind myself why I'm doing this and that it's for my future. But is that all?

He stands up towering over me and leans down kissing me passionately again and I feel like I am freely giving myself to him completely.

He breaks our kiss and reaches his hands beyond my ass and lifts me easily as I wrap my legs around his waist. He carries me down the hall to a bedroom in the back and walks us to the bed.

He lays me on the bed and continues to kiss me on my cheeks and neck. One by one he releases the buttons from their eyelets until my black lace bra and breast forms are freed to him. He kisses all around my chest removing my breast forms so casually as though he has done this before.

His hand slides under my bra squeezing my nipple then leans down and kisses and bites gently.

I moan aloud as his hand goes over my bare belly and over my skirt lifting it subtly then his hand is on my panties and between my thighs.

He begins rubbing my little cock like it's a vagina as I close my thighs around his hand moaning uncontrollably.

My knees bend, toes pointed out and my back arches as his mouth on my nipple and hand in my crotch sends chills all over my body driving me crazy.

He slides me over just enough to climb on the bed next to me. His hand moves as he now runs it down over the outter part of my thigh with my legs bent, and down to my ass as he's still nibbling on my nipples.

"Ohh Rob," I whimper as it's completely making me swoon. I feel so sexy, so girly.

Then I feel his hand groping and cupping my ass all over and he moves up and kisses me and I kiss him back sweetly holding his face with both my hands.

"Your entire body is so soft and silky, baby girl."

"Mmmm," I moan on and on forcing him to kiss me again.

Then he breaks our kiss and places little kisses down my body, each nipple, down over my tummy and stops just above my skirt. Without warning he flips me over onto my belly and runs his hands over my ass.

His hands went all the way down my over my calves to my ankles and feet pulling off my sneakers then slowly back up again. His hands pass over the back of my knees then my thighs and slowly, gently he parts my legs just a little. His hands slid up my ass and I feel his fingers take hold of my panties and begin to pull down.

I look back at him but do nothing to stop him. I watch as he gives a good tug and they come down even more. I lift my hips as he pulls them all the way off and down my legs.

Now I do feel tiny below him, so vulnerable allowing him to do as he will.

"So sweet." He says as he spreads my ass cheeks and leans down.

He kisses both my cheeks sending waves of chills throughout my body. Then I feel his warm moist tongue run from just behind my privates up my crack and over my hole.

I moan aloud, my body reacts to his licks as my ass lifts up.

He does this several times and I moan louder each time. My hips grind against his tongue as he stops at my hole and slides it inside me.

"Ohhhh!" I cry out.

He really digs his tongue into my ass and it is the most amazing feeling my body has ever had. I just moan and wiggle my ass while he assaults my virgin hole. He's no longer being be gentle either, he lifted my ass up by the hips and is really going to town eating me out.

My mouth is open as I breath heavily and moan softly.

Then I feel a sharp intrusive pain as he pushes a finger inside me. I squeal and cry out as he stops pushing but his tongue is still driving in and out. Then his finger is in me, my legs are straining, my toes straight out as the pain is searing hot but his tongue offsets it just enough to make it tolerable.

It takes a moment but the pain eventually subsides and I hear him say, "relax honey, just relax."

I do as he says as his finger slowly slides in and out of my virgin ass. He spits down there giving his finger more lubrication to glide in and out easier.

I'm moaning on and on as he finger fucks me. Then he moves so he's kneeling next to me and leans down kissing me on the cheek and neck, nibbling on my ear and whispering in my ear, "you have a sweet ass Taylor and a beautiful mouth. Look at those sweet sissy lips."

In a dreamlike state I look at him and he puts his hand right up to my mouth putting a finger on my lower lip.

I close my lips around his finger and suck sensually on it. "Mmm." I moan.

"Oh yeah..." he picks up the pace fingering me as I suck on his finger.

"Do you feel like a slutty little girl?" He asks.

"Mmmhmm." I moan.

"I'm gonna stick another finger in you now." He says and then I feel my asshole spread out wider as he slides another finger inside me.

"Mmmmmm!" I moan even more.

He's really fingering my asshole vigorously as I suck on his finger. My ass is rising up to greet each thrust while he goes knuckle deep. With his fingers inside me massaging my anal walls, I'm moaning and swooning while sucking sweetly on his fat finger.

"I'm gonna make you cum baby." He says.

I'm looking up at him holding his hand with both of mine running my tongue all around his finger. That familiar feeling of release is building up in my scrotum as my legs tense up even more and my breathing gets heavier and heavier.

I can feel every movement of his fingers inside me and I'm going to explode. I stop sucking his fingers and open my mouth wide gasping and shoot my load all over the bed as my body spasms and jerks. One load two and more than I've ever cum before in my life as he continues to finger me.

I scream out in ecstasy as my orgasm hits a new high and my body slumps back to relaxation. I'm spent and lay there motionless as his fingers slow to stop.

When they begin to retreat from my virgin hole I miss them immensely.

Then he's behind me again and now he spreads my legs wider as I feel him positioning himself right at my virgin ass. Eagerly I anticipate what's about to happen and he doesn't disappoint. The head of his cock pushes at my hole stretching it wide and I moan aloud as he gets it just inside me.

Slowly he pushes deeper and the pain is searing hot. My hands grip the bed tightly as I cry out and he stops.

"A little at a time baby, just relax." He says soothingly.

I'm way beyond relaxation, I'm in full fuck me now mode. I push back on his cock as it gapes me and goes deeper.

"Ooohhhhhh!" I cry out. "Is it all the way in yet?" I ask timidly.

"No baby but we're getting there."

He pulls back then pushes in again repeating this over and over as my ass rises with each thrust.

I feel the girth of his fat cock as he spreads my tight hole wider. I can feel the big veins and ridges in my ass as he glides slowly in and out of me. I also feel my limp little dick dripping with my own cum.

"Ahhhh!" I moan as he pulls back then drives deep inside me again and again.

"Is it all the way in?" I ask again.

"It's been all the way in baby." He says panting.

He pushes deep and I feel something stop the fat head of his cock and I seem to cum again, it's a spot that he holds there grinding as I cry out.

I've never felt anything like this before, all I wanted was his cock to stay there inside me as my little tight ass wiggles against it.

He lifts my ass up by the hips and pushes my head to the mattress and really begins sliding in and out of me faster and harder until I'm drunk with lust panting, whimpering and moaning with my mouth open. My whole body being jerked back and forth as he drives his rod in and out of me.

I reach between my own legs and even though my little dick is limp I rub it as though I have real pussy and it's so so wet. I rub faster as he's working himself into frenzy. He's breathing hard, making loud grunting noises as he slams that beautiful cock into me over and over.

"Ahhhh fuck baby!!" He cries out as he pushes his meat deep and I feel it throbbing.

He's pumping and dumping his load inside me and I can feel it fill my ass cavity and it feels so wonderful! I don't want this to end! I never want this to end as my own dick drips another load all over my hand.

But at last he slows to small thrusts and then completely comes to halt with one last squirt of his thick juice inside me. He's spent, collapsing on top of me as we fall to the mattress.

Rob wraps his arms around me kissing my neck until I'm able to readjust and turn my head enough so we make out in long sweet kiss.

When he finally slides his cock out I feel his juices slowly drip out of me and turn so I'm facing him and snuggle into his arms.

This is how woke up hours later still in his arms. At first I thought about getting up and ordering an Uber than I realized I liked this too much and went back to sleep.

We're having coffee in the morning and Rob put my clothes in the wash as they were soaked from last nights romp in bed. So I'm just wearing one of his sweatshirts which covers me enough to be very sexy. I had told him I'll leave whenever he wanted me to but he asked me to stay.

So here I am, snuggled up on his lap as we talked about nothing in particular.

Billy did text me several times asking where I was and if I was okay. Did I need a ride or do I know when I'll be home.

It wasn't until noon when we took an Uber back to the bar and picked up his car and he drove me home. He asked to see me again and I said I'd like that but I did have a busy week especially with the pageant beginning on Friday.

He told me to worry about that, he's pretty sure who he's voting for.

I'm in the shower now and daydreaming of last night. My ass still throbs from the pounding I took and I still wanted more. I loved being a girl and being with a man. Rob is nice and all but I didn't want him as a boyfriend. I knew who I wanted but I knew that would never come true. Billy would never date a girl like me. Mike would be nice too but I'm out of his league. Patrick is a big no so I just resigned myself to the fact I'd have to wait until college. That is, if I can win both pageants.

Sunday was a sit around day and do nothing and Monday and Tuesday I worked. Wednesday Renee and I were home alone after dinner and our conversation took a crazy turn from this pageant and what I would be wearing, to sex.

"Excuse me?"

"You heard me, don't be like that." She says grinning mischievously at me, "how was getting dick for the first time?"

"I'll never tell."

"So you did! Yay! C'mon, tell me!"

"No!"

"Did you suck his dick."

I stared at her and shook my head no.

"Aww why not? It's my favorite part of sex."

"It didn't go that way."

"Wow, you just went right to it huh? But wait, did you fuck him or did he-"

"He fucked me and it was the best thing I've ever done in my life!" I said really fast and was so happy to finally share that with someone.

"Ohhhh my God!!" She hopped out her chair and jumped on me, "you little slut you loved it!"

"I did now get off me."

"Who, Billy? No wait, Pat!"

"Neither. Rob Fisher."

"Nooooo! O-M-G!"

"Get."

"Off."

"ME!" I yelled. She giggled as she fell on the couch next to me and leaned on me. For the next half hour we talked about happened and what he wanted. He wants to see me again and I'll probably go but not until after the pageant. I told her I didn't want to go back to being a boy and she said she kind of thought this would happen. Her and my mother always thought I was too sweet for boy. And she also added I have her full support and I should know our mother does too.

The last thing she had said to me was she had seen Billy Sunday and he looked sort of bummed out. After they had spoken she realized he was jealous. Or hurt that he wasn't the one with me.

I thought about that all week and when I did talk to him he was short with me. No angry just curt.

This will not do.