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Gue$$?

She'll do anything for her mom

How did I get here? What do I do now? I can’t believe I allowed them to talk me into doing this. When did I decide I wanted to become an object for men to leer at? Do women actually like being objectified and degraded by men for fun?

The music began to play in the common room of the sorority house. Around me stood these Barbie doll looking girls who thought their body was more important than their brain. The way the guys out there sounded made me wonder if they could be right.

I usually despised this kind of gathering but when Meadow came to me and told me that I would get a portion of the money raised, I knew I had to at least try.

I researched how to dance in front of oversexed men and women by watching Coyote Ugly, Bring it On, and some other brainless dribble. I couldn’t believe people watched that drab. I felt my brain cells cry out for some sort of knowledge. If I didn’t need the money, there is no way I would be here.

I picked up the scrap of fabric and held it up. How could Meadow expect this thing to cover me up?  I looked at the other girls as they walked around in their thongs, they did not seem to have an issue with their breasts hanging out. They pulled the white t-shirts over their body. The question mark with a ‘Gue$$ ?’ logo stretched across their breasts. I looked down at my size DD’s and hoped no-one would guess their size.

I stripped out of my jeans and shirt. As I looked at my white cotton underwear and bra Meadow walked into the bedroom and came to me. “Winter, look at you, how have you hidden that body for all this time? You are gorgeous.”

I blushed as she praised a part of me I only saw as normal. Nothing special, not like my knowledge. I graduated high school at sixteen, aced my first three years of college, but now I need this money. My mom was my biggest supporter, she always pushed me hard. She reminded me that looks come and go but a brain is with you no matter what.

“Come on girl, those guys are going to love you. I am sure they won’t know what hit them when they see you. Let’s get this t-shirt on. Here put a little gloss on your lips.”

Meadow took the white fabric out of my hand and pulled the t-shirt over my head. She grabbed a pair of scissors from the vanity and made a slit at the neck to make my cleavage stick out even more. She then applied some lipstick to my lips and pulled my hair out of its normal ponytail. Meadow proceeded to brush my hair out and told me to shake my head. When she turned me to face the mirror I gasped.

'Who is this woman?' I had never looked at or thought of myself as a woman before.

In nineteen years I'd never had a date or had a man look at me like they would like to date me. I wondered if Kai would be here. I'd had a crush on him for years.

“Winter, your group is next. Are you ready for this?” Meadow asked concerned.

“I'm as ready as I'm going to be.” I laughed nervously.

“You can do this. You’re beautiful. When you go out there dance around a little, then take a pitcher of water and dump it over yourself. Make sure your tatas are on display, girl.  Chloe is going to be recording the guesses."

Meadow handed me a drink as she explained this to me. I downed it one gulp. The bourbon made me cough but gave me the courage I needed. I looked back before I walked into the common area as Meadow took off her skirt. The last thing I saw was her tan cheeks with a black thong between them.

The common area was full of people, both guys, and girls. The other contestants were dancing around them. These girls were in their element. They danced in clubs and at frat parties. One of the Barbies came up to me with her fake smile. “I don’t know why Meadow brought you here. You're never going to win. Why don’t you just keep your nose in your books?” she said while dancing around me.

“Fuck off bitch! I need this money, I don’t expect you to understand. Someday when you realize the world does not revolve around your body then maybe you'll be able to see why this is important to me,” with that I started shaking my ass and moved away from her.

I thought of my mom and reached deep inside for my inner ‘coyote.’ I knew I could do this. I moved to the music, shimmying and shaking my body, then bent forward, grabbed the pitcher of water and in front of a group of frat guys dumped it all over my breasts. The water was cold and my nipples hardened instantly. The t-shirt didn’t hide anything and the guys started hooting and hollering.

I heard Chloe call me to the front of the room. “Alright girls and boys,” she yelled. “We have here for your viewing pleasure Miss Winter in all her gloriousness. What do you think of these gorgeous girls? Write your guesses down.”

As she spoke I followed the lead of the girls before me, I leaned forward pressing my breasts together, moved closer to the group in front of her and allowed them to dump more water over me. I couldn’t believe I actually was doing this. I needed to do this and win all the money I could though. With that in mind, I listened to Chloe.

“Guesses ready? Let’s see who is the closest to Winter’s size,” Chloe held up my white cotton bra so all could see she had the correct size.

“Everyone here knows how this works, the person closest to the correct size will get to fondle her tatas. In the event more than one person guesses the correct size then we will draw straws.” I turned to Chloe and whispered in her ear. “Well, well, well, it seems Miss Winter here is quite daring tonight. She has just upped the stakes. If more than one person guesses her correct size, you can all fondle her gorgeous breasts tonight then try to outbid each other to have a night with Winter."

A round of applause and hoots echoed around me. Chloe began to read the guesses. I shook and shimmied around the room one last time.

“Okay, all the guesses on Miss Winter’s girls are in? The results are that we have Jessica, Jack, Alan, and Kai with the correct answer of 38DD.  There were also several close guesses, thank you all. Don’t worry there are plenty more girls to try to guess but you four come on up and see what Winter has going on under this t-shirt of hers.”

Jessica stood right in front of me, she is the president of the sorority. I was not aware that she would enter a guess. She looked into my eyes as she reached up and pinched my nipples through my wet t-shirt. I never had anyone besides a doctor touch me before let alone a woman. I was uncertain how to handle the situation. She then cupped my boobs and pressed her face into my cleavage and kissed down to my nipples. Everyone watched us and I felt butterflies in my stomach as I stood there blushing with my pussy starting to tingle.

Jessica’s hands were replaced by John’s. John squeezed, caressed and kissed my breasts. I felt myself get redder and the tingles increased deep in the pit of my stomach. He ripped my t-shirt open and sucked on my nipples. I let out a gasp as the room became silent. Even the Barbies couldn’t believe I allowed this to go on. They thought I would stop them by now.

Alan fondled and squeezed my breasts together. He leaned down and began to ‘motorboat' between them.  Before I knew it I stood before Kai in just my underwear, blushing profusely.  I smiled at him as he leaned in and touched me gently. He was sweet and tender, not like the other guys.

He whispered in my ear, “You're beautiful, not just your breasts but all of you. When I heard you entered I paid my fifty dollars to be here.”

I didn’t know how to respond but I hoped he won the auction later. I wanted to explore these feelings I had with Kai. All too soon Chloe called time.

I walked back in the other room to get a new t-shirt for the contest as the next girl went forward. I was thinking that if I was going to lose my virginity soon it was for a good cause and I could think of no one I wanted to do it more than with Kai.

I bumped into the girl from earlier with the fake smile. “You think that auction makes you special? What do you need the money for?” she asked.

“My mom had always been my biggest supporter. She pushed me from the time I was born to make something of myself. It was always just her and I. My dad died when I was two. My junior year in high school my mom was diagnosed with breast cancer. She had a mastectomy. Last year her cancer came back and I lost her. All the money I make tonight will go towards her trust to help find a cure for breast cancer. She always told me my body was not as important as my brain. I believed her but when I saw her lose her breast she was depressed for so long I didn’t understand it. Now I can see why. I still believe my knowledge is going to get me where I want to be in life but being a woman has some positive points.”

“I am so sorry to hear about your mom. Thank you for sharing with me. I know we got off to a bad start but I would like to be your friend. My name is Lyndsey. You can have any money I raise tonight for your mom’s trust.”

“Wow!  Lyndsey, that’s so sweet, however, I think we better get back out there. It’s time for the wet t-shirt contest.”

Meadow had just come to the door to call us as we walked out. All of the girls were lined up in front of the room. We took our places as Jessica and few other girls started to dump water on us. We then took the pitchers and dumped more on ourselves. I took my pitcher, stepped forward and shook my boobs as I dumped the water over my head and chest.

I found Kai and smiled at him as I did. I danced around happier than I had been in a while. Lyndsey smiled at me and let out a cheer. Kai whistled from the back of the room. I couldn’t believe how many people were chanting my name. For the first time, I felt like I could win this contest.  Chloe and Jessica judged the applause when they came before me everyone erupted into hoots and whistles. I just kept dancing around, not knowing what else to do.

Lyndsey came up behind me and whispered, “You’re amazing, you got this girl.”

Jessica turned to the crowd, “The winner of tonight’s contest, the surprisingly sexy Winter!”

Chloe then told them, “Coming in a close second and third we have Meadow and Lyndsey. Everyone did amazing tonight and now for the final part of the evening the auction of Miss Winter.”

Meadow and Lyndsey stopped Chloe and spoke to her briefly. “Well, well, a change of events here it seems that after we auction off Winter to her four winners the other pledges and ladies here would like to hold an open auction.”

I looked from where I was standing, surprised at what I had just heard. Meadow came beside me and whispered, “All the money we raise tonight is going to your mom’s trust, Winter. I wish you would have told me what you were going through.”

I didn’t know what to say. I just stood there as Chloe called me forward.

“Jessica, John, Alan and Kai are you ready to start the auction for our beautiful Winter?”

Jessica opened the bid yelling, “Twenty-five dollars.”

Quickly followed by Alan, “Thirty.”

John yelled, “Thirty-one.”

Jessica countered, “Fifty dollars.”

Alan stepped back and John said. “I’ll save my money for the…”

He was interrupted by Kai, “I bid one-hundred dollars for Winter.”

He looked at the other three as they stood shocked.

Chloe then said. “We have a bid of one-hundred dollars going once, twice.” Looking around she smiled at me and yelled, “Winter you are sold to Kai for one evening.”

The rest of the evening went in a blur as the other girls were auctioned off. Everyone had been paired up. It was a fantastic night. I set up a date with Kai for the next evening. I was very nervous as I walked into Meadow’s room.

“Meadow, I need your help. I’ve never been on a date before and the only time I ever kissed a boy was in junior high. I don’t know what to do or wear or anything.”

“Come sit here sweetie, let’s see what we need to do. Clothes are simple. We can find you something between all of us girls. Just be yourself, don’t try to be something you’re not. He'll like you for who you are.”

“You don’t understand, I really like Kai. He is so handsome and smart. We have classes together. I didn’t think he even knew who I was. What if he wants to kiss me or something else. I mean shaking my ass out there was one thing even allowing them to touch me was hard. I just thought of my mom and needing to do it for the money. This is different.”

“It’s okay, Meadow, I'll help you the best I can.”

We were both still in our t-shirt and underwear, Meadow leaned forward and kissed me.

I froze, “Wha... what are you doing?”

“Shh, I am just going to help you feel more comfortable with yourself and with him. I’ll take it nice and slow, if you don’t like something we'll stop.”

Meadow leaned forward again as her lips brushed across mine softly. She slowly ran her tongue over my lips until I allowed her entrance. She caressed my tongue in a sensual dance. She pressed forward and I lay back across the bed. She continued kissing me gently, passionately as her hands began to slide up my body. She lifted my t-shirt, to reveal my breasts as she did so. Her soft hand cupped my breast as she kissed down my neck. She then blew on my nipples making them hard and pointed. I never knew they could be so sensitive and just wanted to feel her warm mouth on them. As if she read my mind she took one nipple in her mouth and sucked on it. I let out a moan unsure where it came from. I felt butterflies in my stomach and feelings I had never felt before.

Meadow lifted my t-shirt off and took my breasts in her hands, she pushed them together and licked back and forth from one nipple to the other. My back arched toward her and I felt heat between my legs. She kept fondling my soft skin and came back up to kiss me again.

“Winter, you are very responsive. I know this is just to help you relax. If you want to stop here we can.”

“You have made me feel better than I knew I could. I didn’t know how a woman was supposed to feel. Does it get better than this with a guy?”

“When you are with the right guy it can be so much more. Your body has so many sensitive points for them to find. Like right here..” she kissed the nape of my neck which sent shivers through my body.

“You should think about all these feelings tonight. Tomorrow we are going to go shopping to get you some pretty lingerie so you are ready for Kai. Why don’t you stay here at the house tonight, and we can get Lyndsey to help us out tomorrow?”

The next evening as I waited for Kai I looked in the mirror. The girls had helped me a lot. We went out and got sexy underwear and a little black dress. They wanted me to get some super high heels but I just couldn’t do those. I chose a simple pair of sandals to keep myself comfortable.  They took me to the salon and we had gotten manicures and pedicures. I felt like a Cinderella. I just hoped my prince liked me as much as I liked him.

Kai arrived right on time. He kissed my cheek, “You look gorgeous. Wow, you didn’t have to do this for me. I like you as you are.”

“Thank you, I really enjoyed getting dressed up today with Meadow and Lyndsey. They were a big help.”

Kai and I went to dinner and then to a local club. We met up with a couple other people including Meadow and Lyndsey with their dates. We all had a great time. We danced, talked and just hung out. None of them made me feel uncomfortable and Kai stayed beside me the entire evening. He made me laugh and I felt like I’d known him forever. He took me back to my room and I invited him in.

“I had a wonderful time tonight. Thank you. I hope it was worth your hundred dollars.”

“Winter I wanted to ask you out for awhile but didn’t know how to. I only went to that sorority party because Meadow told me you were going to be there.”

I was surprised at his admission then nervously stood on my toes and kissed him softly. When I went to pull back he put his hand in my hair and held me close. He looked into my eyes then kissed me more passionately. His tongue found mine in a sensual dance. At first I felt awkward then I relaxed into his kiss. His kiss was different than Meadow's but it felt amazing. We continued to kiss for several minutes then adjourned to the couch.

We sat on the couch as I lifted my dress off for Kai. I revealed my new black bra to him. He sucked in a breath then cupped my breasts, he ran his thumbs over the nipples making them peek through the satin. He kissed my chin along my jawbone to my ear. When he sucked on my earlobe it sent tingles through my body. He opened the front closure of my bra, my soft flesh filled his palms, and he then squeezed them and pressed them together.

He whispered into my ear, “I love your breasts. They are so full and firm, so soft. Your nipples respond to my touches. I want to taste them.“

He kissed down my neck, he sucked at my nape then over my collarbone to my breasts. He sucked my nipple into his mouth. It felt so good.

I moaned before I bit my lip. He sent chills through my body. Kai sucked each nipple into his mouth. He squeezed my breasts together as I ran my hands up over his back into his hair.

“Mmm, ooohh.” I never knew anything that made me feel so free. I wanted more. I wanted Kai.

He continued savoring my flesh as I arched my back pressing my chest to him. He kissed downward over my ribs and abdomen down to the top of my black thong. He looked into my eyes as his fingers found my moist core. He slipped under the fabric to my wet kitty.

My body responded to his touch while the butterflies grew wild in my stomach. I needed to feel him. I didn’t know what else could quench the fire within. I looked into his eyes, whispered only, “please.”

Kai stood up and lifted me in his arms. He carried me to my bed. I lay back as he slipped my panties off, then I watched him undress. I had never seen a naked man before and I watched in amazement. Every button revealed his muscular chest. He had a tuft of hair that led to the button of his slacks. He slowly opened his belt before he flipped the button on his pants. As he pushed them over his hips he took his boxers with him. I saw his hard cock and let out a gasp.

“Will that hurt?” I asked nervously. “You're so large.”

He laughed, “Yes, darling I will fit. Your body will stretch around me. There will be a little pain, but then I hope you will feel nothing but the pleasure. Are you sure you want to continue? We can stop.”

“I want this, Kai. I want to give myself to you. Please be gentle with me.”

“Of course, Winter. You are precious.”

With that he crawled beside me and kissed me passionately. He inserted a finger into my wet slit. It felt amazing. Then he entered a second finger which was a little uncomfortable but still bearable. He pressed his thumb on my clitoris as he curved his fingers. He brought me to my first orgasm quickly. My body jerked under his ministrations. I moaned in ecstasy. He moved over me in the midst of it, he pressed his cock to my drenched opening. He slipped easily in until he hit my hymen. He pressed harder until he broke through kissing my moans.  He pushed until he filled me up and stopped. He held himself still until I relaxed around him.

Kai held himself up on his forearms as he began to move slowly. I was so full, it felt beyond any word I knew. I closed my eyes as Kai moved his hips up and down. He was very gentle but I didn’t want him to hold back. I began meeting his thrusts. He leaned down taking my nipple into his mouth and sucked. He was making my body quiver all over. I felt his cock throb against my walls as I erupted. It was euphoric, there were colors behind my eyelids. I moaned and yelled as I dug my nails into Kai’s back.

“Oh Winter, fuck you’re so tight I’m going to cum all over your gorgeous tits.”

He pulled out, got on his knees and stroked his cock. I looked up at him through hazy eyes as the first shot of cum landed on my chest. It was warm and sticky. Another rope landed on my nipple, I took a finger and swirled it around the sensitive nub before I brought it to my mouth to taste it. It was kind of salty but not a bad taste. I sat up and took Kai’s cock between my lips to clean him off. He was soft but hard. I ran my tongue over the head then brought my mouth to the base of his cock. I pressed my lips together and came back up as I cleaned him completely.

Kai kissed me deeply, then went to the bathroom. He came back with a warm washcloth to clean me off. After he made sure I was no longer sticky, he took me in his arms spooning me as we drifted to sleep. His hand cupped my breast all night.

I awoke the next morning with a text from Meadow, “We raised five thousand dollars for your mom’s trust. I am going to ask the sorority alum if they will match it. We’ve voted to have this fundraiser every year in honor of you and your mom. Hope you had a great night. I want deets later. Luv you gurl.”

I smiled as I curled back into Kai’s arms and drifted back to sleep. I thought I saw my mom in my dream. She smiled at me and told me she was so proud of me.

I didn’t think I could go through with it but was very happy I did.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com with this note attached, it has been posted without my permission.

Copyright © {2018/infinate}copyright by tonyal
Everything I write is a product of my imagination, rarely is there any truth thrown in. Any resemblance to any person or place is purely coincidental. This work in any form may not be copied or used in any way without written permission from the author(s).

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