Kylie's New Life: The Ball

Story Info
Kylie wants to spend a night as a girl and becomes a woman.
2.3k words
4.46
19.2k
14
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
AmeliaZay
AmeliaZay
145 Followers

I was nervous but the girl on the phone assured me that their salon assured me that they were very friendly to LGBTQIA clients. I almost chickened out. I had never been particularly feminine at five foot eleven and two twenty with a long beard. I was never mistaken for being a woman. The thing was I wanted to be at least for a night. I was willing to shave the beard for tonight. This night was going to be special.

They shaved my beard, gave me a mannie peddie and fitted me for a wig cutting and trimming it to get it ready for the night. The girls were so nice. They were so supportive and complimented the dress I was planning on wearing. My nails were all painted red to match it.

It was about a month before I had even heard about it, The Rainbow Ball, a night of dancing and fun for everyone in the LGBTQIA. I had been quietly crossdressing for maybe a year now. And though I was usually fine being a guy I wanted to just have one night just one being a woman.

I got home after my time at the salon and it was already getting late. The Ball started at 8pm and it was already 4pm. I ate a light meal and started getting ready. I showered and shaved. I had naired myself the day before but shaved everything again including my face. I rubbed lotion into my skin making it soft. I started my makeup. That was harder, I had never done my full face but I did manage to make it passable. The wig was next, I clipped it in place. It was time for the dress. It was a red ball gown with a corset style bodice with sheer off shoulder straps. The skit was wide and layered sheer material. The top had rhinestones and it had glitter and was very very girly. I started with a white strapless bra and matching lacy panties with white pantiehoes. I put on my dress on slowly pulling on slowly, it felt so good as I zipped it up.

I looked at myself in the mirror and slowly put on a golden tiara. I grinned big and twirled. I put on a pair of black heel boots with golden buckles. (Yes I could walk in them) it was time. I managed to get to my car fairly easily. One of my neighbors might have seen me but I did not care. I drove away slowly. About an hour later I had arrived.

I checked in under the name Kylie. No one even questioned it. Everyone here was gay bi pan or whatever. I was not even the only guy in a dress there. I went to the dance floor and twirled on my own for a while, but with no one to dance with I moved aside and let others dance. I was so happy smiling and swaying and feeling the dress rub against me and the rustling.

"Can I get you a drink?" I looked up, he was tall, about six foot five with broad shoulders. He was bald with dark skin and dark eyes. He was smiling. "My name is Jacob, may I get you a drink?" I felt myself blushing. He extended his hand to me. I finally found my voice.

"Yes please, and thank you" he smiled showing perfect white teeth.

"May I know your name?" I started to reach for his hand and he took it and kissed my knuckles. I blushed harder

"Kylie... My name is Kylie!" He smiled again, still holding my hand.

"It is a pleasure to meet you Kylie," he bowed to me, "as I said my name is Jacob. Is this your first time here?" I nodded. He flashed another smile. He got me a drink and we stood together. I was too nervous to say much as I drank it. He seemed to be fine with the silence though. "So Kylie, where are you from?"

"I live about an hour away from here."

"Planning on staying the night?" I shook my head no.

"I am just here to have fun. I just wanted one night where I could be girly in public" he grinned again flashing those teeth.

"Would you like to dance?" I nodded and he held out his arm and I put my hand through his elbow. He lead me out to the dance floor and turned to face me putting his hands slowly onto my waist. He smiled as I put my arms over his shoulders. He pulled me close and we started to move in slow circles. I could smell his cologne, I wondered if he could smell my perfume. "You are very beautiful Kylie." I blushed my face, turning a bright shade of crimson. He held an arm over my head and twirled me, catching me in his arms. I leaned against him as he put his arms around me. I twirled back around and he did something that surprised me. He kissed me gently on the lips just a quick peck. Yet I found myself smiling as he pulled his lips away.

"Have you ever been with a man, Kylie?" I shook my head no. "So you have never been kissed like a real woman?" I shook my head again. He smiled and he kissed me, his lips pressed against mine slowly. I felt myself responding. Slowly letting myself submit to it, letting a man kiss me with his arms around me. My lips slowly parted, his tongue slipped into my mouth and mine met it and intertwined with it. As he kissed me deeply. I loved it! It felt amazing letting myself be kissed by him. I was reluctant to let him go. We parted slowly. My stomach felt like butterflies were flying around it and my knees were weak, my head swimming. "Would you like to go with me to my room?" I don't know why but I agreed without thinking.

I took his arm again and followed him out of the ballroom to the elevator. I leaned against him as the door closed and he kissed me again, I pressed myself against him feeling his big hands on my back. He broke it slowly letting his lips linger on mine. He leaned over to my ear and whispered.

"Tonight I am going to make you into a real woman" I moaned softly as he spoke into my ear so close I could feel his hot breath. "Would you like that?" I nodded and he smiled that damn smile. He was so handsome. "I want to hear it." I gasped again as he spoke into my ear.

"I...I want to be a woman for you Jacob"

"Mmmmmm good girl!" The door dinged and I put my hand on his arm again as he led me to his room. A mirror on the wall let me see us, him tall and black me shorter with pale skin. I was so nervous and excited. He led me into the room and I found myself against the wall as he kissed me again, dominating me gently, slowly we started to make out. His tongue slipping into my mouth again he pulled me close one arm on my waist the other over my head. His suit jacket came off. I ran my hands up his chest and he was chiseled. I could feel almost pure mussels under his shirt. He slowly pulled his lips off mine, grinning running his hands up and down my body.

"That dress is very pretty, but it's going to get in the way. Why don't we take it off?" I smiled nervously and he slowly started to unzip my dress and it fell around my feet. He smiled looking at my bra panties and pantiehoes. He put his black hand on my waist and kissed me again. This time it slipped down to my butt. He grabbed it gently and I moaned a bit. He took my hand and pressed it against his cock. It was huge!

"You like that baby? It's so hard for you.

"How...how big is it?"

"Twelve inches long and three wide baby girl, and it's all for you." I practically squeaked, that was huge. Way bigger than any toy I had ever used on myself. My smaller seven inch cock strained in my panties. He took off his shirt and slowly took off his pants so he was only in his boxer briefs. They did nothing to hide the bulge, he picked me up and carried me over to the bed, setting me down on the edge. I reached up and put my hands on the waist of his underwear. I slowly pulled them down. It was just as huge as he said twelve inches long three thick cut the head glistened in the lamp light. I gasped and put my hand around it admiring the contrast between my white skin and his dark. I started to stroke him gently. He moaned slowly, "mmmm baby is this your first cock"

"Yes Jacob, this is the first time I have ever touched a cock other than my own."

"You don't have a cock" he reached down and ran a hand slowly over it. I moaned. "This is your clit baby girl women don't have cocks"

"Yes Daddy!" I gasped again. It just slipped out but he smiled flashing his teeth. He leaned in and kissed me. I kept stroking his huge cock, I could feel it's heat and the veins pulsing in my hand.

"Why don't you put your lips on Daddy's cock baby girl" it was not a question I leaned in and kissed the head of it then kissed slowly down the shaft, before licking my way back up to the slit. He moaned softly "that's right baby that's right now suck it, you won't be able to take all of it but do what you can." I could only obey. I slipped the head in my mouth slowly. I started to suck him gently taking what I could into my mouth but keeping my hand around the base of the shaft.

I started to bob my head, sucking as much of the shaft as I could. He moaned in pleasure, pressing and put a hand on the back of my head. He indicated I should look over at the wall. I could see myself in the mirror, his huge black cock in my mouth, me in my white bra panties, pantiehoes and black heels, the golden tiara still in my long brown hair wig with blond highlights. I was a girl sucking a real man's cock.

Jacob pulled himself back letting his cock pop out of my mouth he pressed me back onto the bed and pushed me further up onto the bed spreading my legs. He leaned over to my ear again nibbling at first kissing my neck slowly then back to my ear.

"I am going to make you into a real woman baby girl, I'm gonna use my cock on that pussy of your, I'm gonna breed you baby take you so deep."

"Yes Daddy please make me a real woman please use that hard cock on my girly pussy!" He grinned that damn smile again. He kissed me again and then reached for the lube. He ran a hand down my clit cupping my balls and rubbed gently at my pussy through my panties and pantyhose. He reached up and pulled my panties down then tore a hole in my hose all the way from my clit to my pussy. Letting my clit free, he lubed up his fingers and slowly rubbed around my virgin hole. Slowly pressing one finger into me. I gasped and moaned slowly as he started to push it in and out of me. "Oh Daddy!" I gasped again and he pressed another finger into me then another.

He pulled out suddenly, and for a moment I could not figure out why. I felt something else at my hole, something huge. He pressed his monster cock into me slowly. It was so big he told me to just breathe and relax. The head was inside of me so big it hurt he let it sit for a moment before pressing deep into me with a single thrust. I screamed in pain and pleasure feeling his balls slap against my ass.

" Oh fuck baby your pussy is so tight, are you ready?" I could only nod as he started to thrust. It was so big and so hot deep inside me I moaned and gasped my legs wrapping around him. The pain went away slowly being replaced by an intense pleasure. He kissed me going harder and faster, hitting me so deep in my pussy so deep. I gasped and started to cum hard my clit shooting out my hot white girly cum.

"Oh God oh God Daddy you made me cum with your hard cock oh fuck Daddy it feels so good. He kept thrusting harder and harder deep inside of me. I felt myself orgasming again no cum this time something deeper inside of me spreading through my whole body. My eyes rolled back in my head. As his huge cock fucked the last of the man out of me.

"I'm gonna cum soon baby girl" he grinned over me "I'm gonna breed your pussy baby after this you will never want to be anything other than a girl my girl" I wrapped my legs tighter.

"Do it, Daddy I want to be a girl forever." He kept thrusting harder and harder. Then I felt it, his cum deep inside of my pussy so hot filling me up. I felt myself orgasm again flowing through my whole body. It was all so much I lay there breathing heavy his cum deep inside me still as he slowly pulled his cock out of me he lay down next to me pulling me against him.

"So want me to be my girl from now on?" I could not answer, but he held himself against me.

"Yes Daddy, I want to be your girl" he leaned in and kissed me.

"Good answer baby girl."

AmeliaZay
AmeliaZay
145 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
7 Comments
RachelPrRachelProver 1 year ago

Oh how I do love dark meat!😜😜😜 my goodness 12 inches ouch! I've had eight and yes, he was black and I loved being his white bitch.

AnonymousAnonymousover 1 year ago

I have always wanted a Cder /Sissy or Transgendered Lover prefer one with a nice size Cock but not a 12 incher lol 8 at the Most and yes I do love Oral and anal

AmeliaZayAmeliaZayover 1 year agoAuthor

Hey all! Just wanted to say thank you to those of you who have read and enjoyed this story, and any of my other ones. Some of you may have noticed this is not my best work. I basically stress wrote this story and put it up over the course of a single night. Why? You might be asking. Basically mental health issues. That being said I stand by my work and I hope to put more into this story in the future. I feel like part two of this series is far better. I will keep going and keep improving again thank you all, you have been great!

AnonymousAnonymousover 1 year ago

First of all I want you to know that I liked it.. I read the whole thing an I got a hard-on reading it but the 12" cock. Hmmm.. I know there are some out there but it's a little over-dramatic for first time sex for the guy who just wanted to be a girl for just one night. Maybe develop the story a little more in the middle first. If guys want a story with a fast start and a quick big bang ending.. it was great. I want to simmer a little more before the heat is turned up.

KatiwantsKatiwantsover 1 year ago

A wonderful story!! I hope there will be more!!??

Show More
Share this Story

Similar Stories

Lost Bet Straight guy lost a bet, has to dress as a girl to a party.in Transgender & Crossdressers
Freshman Bride Pt. 01 Zach's college messes up his dorm room so he goes off campus.in Transgender & Crossdressers
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
More Stories