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Losing a Bet
🕑 Added 2022-03-24 12:46:43 +0000 UTCI've always been a bit of a gambler and it's that attribute that has led me into my most perverse and sexual adventure to date. Now granted, I am only eighteen years old and have much more of my life to live but that doesn't make my statement any less true; it just takes away the strength of the statement. At the time my story takes place, around Christmas of 2006, I stood about five feet and four inches and weighed around one hundred and twenty pounds. I was a small man, still a boy. I couldn't even grow any facial hair yet. I had long, dark brown hair that rested just on top of my shoulder blades. I had grown it out for a bet. I was bet that I would not cut it until I graduated high school for five hundred dollars. With graduation only five months away, I had pretty much all but won it. I had soft features and was a bit doughy where I hadn't played a sport in a little while. One thing I was famous for at my school, besides my pension for taking ridiculous bets, was my cute, bubble butt. The girls loved to slap the hell of it as they walked passed. My ex-girlfriend said it was the sexiest thing about me. All of this being said I have to admit, I looked a little androgynous at times.
My story begins at my uncle's house in rural Kentucky. I was visiting my cousin Jenny with my younger brother, Derek. We had eaten dinner and were sitting in the living room watching the film, Scream. I'm Ashley, by the way. It's a family name. And yes, I realize it doesn't help my gender neutrality.
"Hey, Ash!" My brother ask suddenly.
"Yeah?" I replied.
"What year did this come out?"
"1998."
"No, that can't be right. It has to be earlier than that."
"No, I am like 98 percent sure it was 1998."
"I don't know that doesn't sound right to me."
"Well, that's when it was, so deal!" I said harshly.
At this point Jenny started laughing at us which I think embarrassed my brother a little because he gave me a pissed off look. My brother has never submitted to the little brother role. We bicker often. We are only eleven months apart, so we usually do most things together; same sports teams, etc. But my brother is the more athletic one in the family. He over took me in height when he hit fifteen; he is about six feet tall. He is in great shape and pretty popular with the ladies. That has given me kind of a complex, so I typically am a smart-ass to him and put him down when I can to assert dominance. But I do know that he could definitely kick my ass if he wanted to, I just hope he doesn't.
Jenny said, "Here I'll look it up! Derek, when do you think it is?"
"I swear I think It is like 1996." He replied.
"Ashley, do you want to make it interesting?" Jenny ask.
"What do you have in mind?"
"Well, a bet of course. But no money, I want something silly that will benefit me with a laugh. So like a dare."
"Fine, I'll do it."
"Okay. What is your dare?"
"If I win, you and Derek have to run one lap around the house outside... naked!"
"Hey! Why do I have to? This is between you and Derek."
"You orchestrated this whole thing. You are always protecting him and siding with him, so either that or no deal!"
"Fine! But if we win, you have to let me give you a makeover and dress you up like a girl completely. That means panties and a bra! And you have to wear them all the way home to Lexington. I know you'll have to stop to get gas, so you have to pump it too."
At this point I was getting a little nervous, those terms were pretty intense. Jenny has been trying to give me a makeover and make me pretty forever now. She says she knows I'll be so pretty. You would think that a sixteen year old girl would have gotten over the whole makeover thing by now! But I knew I was right. I answered. "Done. You guys are going to look so fucking stupid. It's so cold outside too! Hahaha"
"We will see about that!"
We all got up and made our way to the computer. Jenny googled Scream and the results popped up on the screen. I was wrong, it was 1996. I had her search a few other things before finally conceding to the victors. Jenny and Derek started laughing hysterically. Jenny was able to get out, "You know I probably wouldn't make you do it if hadn't been such a dick earlier."
"But..." I shut up. I had lost and am soon to be humiliated.
Jenny stopped laughing and wiped the tears from her eyes. "Come on! I have a lot of work to do! Derek, you have to stay here and be the judge once everything is done."
"Like a pageant judge" He laughed.
"Exactly!"
Jenny grabbed my hand and took me to her bathroom. She started fooling around under her bathroom sink and withdrew a wide variety of things. At once I noticed the Nair and razor. I felt concerned. "Jenny, I am not shaving my body!"
"Yes, you will. I want to do this right."
"Seriously! No!"
Jenny grabbed a pair of scissors and then grabbed me by the hair. It hurt like hell and I dropped to my knees.
"Ouch! What the fuck!"
"If you don't do this, I swear to God, I'll cut your hair and you'll be out five hundred dollars."
"Okay. Okay. I'll do it. Just let go!"
"Take off your pants and shirt."
I removed my clothing and stood there in only my briefs. Jenny examined me up and down and began rubbing the Nair on my legs and feet and my lower stomach. She got behind me and pulled on briefs a bit and looked down. "Great," she exclaimed, "You have a smooth butt! And it's cute as hell. How'd you get blessed with such a beautiful girl's butt."
"It's not a girl's butt!" I snap.
"Trust me, when I get you in a pair of cheekies, you'll see how girly of a butt you have."
She waited about five minutes and told me to get in the shower and wash off, then she stepped out of the bathroom. I stepped in and washed off all of the hair from my legs. I had to admit to myself that my smooth legs did feel pretty amazing. I grabbed the razor and did a little touch up on the spots the Nair missed. Once I got to my pubes, I settled on the "when in Rome" philosophy and shaved myself completely bare. There wasn't a spot on hair anywhere below my neck. I stepped out of the shower, dried off, and called Jenny back in. When she came in, she was holding a pair of pink and black striped panties with black lace trim, and a plain black bra. I instantly blushed. She looked at me and flashed me a big smile.
"Okay! Put these on and then we will start on your hair and make-up. She turned around and I slid the panties up my leg. They felt really soft. I couldn't believe how comfortable they were. My cock and balls actually didn't feel too constrained. Granted, I've never considered myself well endowed. Hard, I'm maybe four and a half, five inches. I checked out my ass in the mirror. Wow! I couldn't believe that was my ass. It looked sexy as hell. I hiked the panties up just a bit more to show off a little more of my butt. God, I did have a girl's butt! Involuntarily, probably because of the silky feel of the panties on my smooth cock combined with my lust over my own ass, my dick began to grow. Jenny turned around.
"Holy shit, Ashley! You are hot as hell. Look at how amazing of an ass you have. It's not fair to a girl like me with barely any ass to speak of." She then noticed the growing bulge that was tenting the cheekies. "Do I need to leave so that you can take care of that?"
I turned a bright red and turned away from her. She laughed.
"It's okay! It's natural. So, let's put this bra on you . I found it in my closet, it's a 34AA I had back in Jr. high."
I put my arms through the straps and she adjusted them to fit me and the clipped it in the back. Then she pulled as much skin as she could to fill the cups. She did a pretty good job, It appeared as though I had little breasts. In the mirror I was beginning to look more and more like a girl, still pretty boyish though. Jenny sat me down on her bad and grabbed her make-up, a blow dryer, and a straightener. She blew my hair dry and then straightened it. Then she put in a black head band. She then applied make-up. She didn't use foundation, just some jade eye shadow, mascara, a little blush, and a pink lip gloss. She went to her closet and grabbed a pair of black leggings and had me slide into them. She then grabbed a tan linen shirt, that came down just a little below my butt and then put a thin black belt around my waist. She grabbed a bottle of perfume and lightly sprayed my neck and a little in my hair. Then she gave me a pair of cork clogs she had been given as a gift that were too big for her. If I was a girl, I'd say they were cute. Jenny looked me up and down then paced around me and stopped."I think I have done a damn fine job! You look beautiful."
I looked in the mirror, she was right. I looked like a girl straight out of an American Eagle catalogue. I didn't just pass as a girl, I actually looked pretty hot. I'd give myself an eight out of ten. I stood there and admired myself. A smile began to grow on my face; I have to admit, I felt a little girly and very pretty. Jenny noticed. "Ashley, It's a shame you are not a girl because I think you could have almost any boy out there!"
"Oh shut up! I'll admit you did a damn fine job but let's go show Derek so I can go home and get out of all this girly shit!"
Jenny seemed a little hurt by my comment. "You may look like a cute girl, but you have the mouth of a bitch!" I shot her a mean glance and began walking back to the living room. Jenny ran ahead of me and stood in front of the door, she announced, "Ladies and Gentleman, may I introduce, miss Ashley Maggard." When I walked in, Derek had set up his phone to play "Kiss Me" from Sixpence None the Richer, effectively recreating that scene from She's All That. Once I got in, Jenny began clapping, Derek just looked kind of awestruck. I stood there and parried and twirled, just trying to have fun with it. I felt bad for my comment towards Jenny earlier, I knew she was really proud of her work. Also, I didn't want them to think that it bothered me lest they make fun of me about it forever. This went on a little longer and then I tripped in my shoes and fell. Jenny and Derek began dying laughing. "Shut the fuck up, you assholes!" I yelled.
Derek quipped, "Wow! She has the mouth of an angel!"
"Tell me about it. So what do you think?" Jenny replied.
"She is pretty girl! Great ass! I'd give her about an eight"
"Okay! An eight's fair. We don't want her getting a big head anyway."
Jenny and Derek laughed some more."Okay, Okay! We have all had our shits and giggles. Derek, let's go! I want to get home before it gets too late."
"No, no, no," Jenny ran from the room and returned with a camera, "I have to take a few pictures of my masterpiece."
I threw in a few quick poses with Jenny snapping away. Then Derek took a few pictures of me with Jenny and then finally Jenny took a picture of me and Derek. He put his arm around me and pulled me close. Jenny looked at the picture ad remarked, "If you two weren't brother and sister, you'd make a real cute couple."
I looked at her and laughed, "I don't think Karrie would like that!" I then made a whip noise. Derek blushed and looked down at the floor. We all laughed and joked a little while longer and then Derek and I left.
"Goodbye Ashley! Maybe you and I can go on a double date next week. I know some real cute boys!"
"Haha, very funny. But we both know they'd both be drooling over me the whole time instead of your broke ass... and I have a dick too!"
"You fucking cunt! I'll kill you."
I smiled and laughed playfully. "Whatever, bitch!"
Jenny smiled and yelled through her giggles, "Cunt!"
We climbed into Derek's car. As I got in, I noticed him checking out my ass. Gross! My own brother was ogling me like I actually was a girl. I smirked though, I felt kind of devilish, like I had some new kind of power. We drove a little ways before we stopped at a gas station. Derek turned off the car, "Okay, you have to pump the gas!"
I looked up at him, "Do I have to? I'm already humiliated enough. Would you do it, please?"
"No, bitch! Go pump my gas."
I stuck out my bottom my lip and fattened it up and widened my eyes real big. It was my first attempt at the pouty, puppy dog face. "Please?" I begged in the girliest voice I could manage.
"Okay! Fine" He got out of the car. I couldn't believed that worked. We usually argue forever, until someone finally gives in. This is one of our shortest bickers in like five years. While I was like this, I was going to use this to my advantage. Derek opened the door, "Hey! I'm going to grab a coke. Do you want anything?"
"Umm... A diet mountain dew. Thanks."
That was weird. I am not used to Derek being kind or polite. He was acting like a real sweet heart. It seemed genuine. I didn't know how to handle it. I watched as Derek went inside. Two guys smoking outside the store were staring at me. We made eye contact and one of them gave a flirty wave, I rolled my eyes and turned away. I could hear them both howling-- it made me smirk. Derek returned, hung the pump back up, and climbed in. He reached in the bag and pulled out a diet mountain dew and a rose."I felt like since you are only a girl for another hour and half, you should get some of their luxuries." I looked at him with suspicious eyes, "Thanks..." He laughed, then I did too, and we drove off.
We drove on a little ways and were almost to London, Ky when Derek was pulled over. He had speeding about fifteen miles an hour over the limit. Derek has always been a bit of a speed demon. "Oh great! Someone else is going to see me like this." Derek looked at me, "just act as girly as possible and I swear he won't know, you really do look like a pretty girl."
The officer approached the window, tapped it twice and Derek rolled it down. The officer ask, "License and registration."
Derek handed both to him.
"Do you know how fast you were going?"
"Umm... seventy-five."
"Try eighty-six!"
"Ouch...yeah."
"You are also in a construction zone. The speed limit is fifty-five. You were going thirty-one over."
Derek had only had his license for six months and had already received two warnings and two tickets. He was going to lose his license because of this and he knew it, I knew it, and this officer was about to find out about it. On top of that the fine would be huge. He would have to work a summer job just to pay it off. The officer walked back to his car. Derek looked like he was about to cry the whole time. I just sat there silent. Derek finally spoke, "Shit! If I lose my license, Karrie will break up with me for sure." I looked over, he was facing straight ahead and tear began to roll down his cheek, he tried to catch it before I noticed but he didn't. I look back ahead. The officer returned.
"The fine for this is going to be around two-thousand dollars and you are definitely going to lose your license..." he paused, "....but maybe we can work out a deal." Derek and I were all ears. He glanced over at me and licked his lips, I got really creeped out and nervous. He continued, "How about I stand here and watch while your little girlfriend here sucks you off and I'll forget the whole thing!" I looked at Derek horrified, Derek looked back at me in shock. I looked up at the officer. "He is my brother, freak!"
"Even better!" He replied.
"No, you perv!"
"Okay. How about this? You suck off your brother and I'll clear his record. No record of his past tickets will show up."
I got curious. "Why wouldn't you just ask to get your own dick sucked?"
"I like to watch, that's how I get my kicks."
I looked at Derek. He was looking at me with wide eyes of desperation. Two-thousand dollars, no license, and no girlfriend. That's a heavy price to pay just for speeding. And he had been so nice to me earlier, I mean it didn't deserve this but still he was nice. Derek stared back and whispered, "I'm sorry but please?" I didn't want to do this horribly gay and disgusting thing, but I had to. I couldn't make my brother pay that big a price.
"Fine. But you never tell anyone about this!" I looked at the officer, "And I want your handcuffs and baton! I've always wanted some of those.""
"Ooo kink! Fine. Get sucking!"
I got on my knees in the chair and leaned over the center console. I reached out my hands and grabbed Derek's pants, undoing the button and slowly unzipping them. With a little help from him, I slid them down to his knees. I could see my brother's cock growing in his boxers. He was getting very excited. I licked my lips involuntarily and pulled down his boxers. His half-hard dick flopped out. It was huge! My brother was packing some serious heat. He had huge heavy balls that hung low and a long, thick cock. I was mesmerized and jealous all at the same time. How could he be this much bigger than me? It's not fair, but I had to admit it was such a gorgeous penis. I reached out my hand and grabbed a hold of it and started slowly jerking him off. His dick shot up to an impressive eight inches, doubling my own penis. I started to drool a bit. I was really starting to get into this and I haven't even had his dick in my mouth yet. My own penis was rock hard and tenting in my panties. I don't think I have ever been that hard before in my life. I had to admit I was starting to enjoy my submissive role.
Some pre-cum had begun to leak out of his piss hole and was trailing down the head of his dick. I gave him one last look, and lowered myself down to his fat, beautiful cock. I kissed the head and licked off the pre-cum, then I took the head of his cock into my mouth. He tasted salty, hard, soft, warm, and smooth in my mouth; it was a terrific feeling. "Oh! Oh! Wow!" my brother moaned. I lowered myself further, feeling every thick vein that lined my brother's tool until I could feel his dick poking the back of my throat. Then I raised back up, sucking hard, but not too hard, tracing my tongue all along the underside of his shaft. Once back at the top, I began to bathe his cockhead with my tongue, trying to get into his piss slit I then lowered myself back down .My brother's moaning was loud and constant. I took my hands, grabbed his balls and massaged them while I sucked. I then pulled off of his dick and licked it like a lollipop, tracing the veins from the base to the head and back down again. At this point I was worshiping my brother's massive penis. My brother moaned loudly, "Oh god, Sis! You are so fucking good!"
I admit I was beginning to take pride in my work. I wrapped my lips around his penis once again and took him as deep as I could, then I again pulled off of him slowly, squeezing his dick with my pursed lips. My brother's dick was getting harder and he was moaning between every breath. "Oh, you are amazing! You are so much better than Karrie! Oh.. Mmmm."
I was really into the moment and I started moaning and humming on his cock as I sucked him up and down. I was being more consistent and quicker with my pace. I took my other hand and reached into my leggings and began rubbing my dick. My panties were soaked with pre-cum. I don't know why I was enjoying doing this so much. Maybe, it was the pure insanity of the situation, maybe it was all the attention and praise, I have no idea. All I do know is that I was sucking my brother's dick like a cock gobbling whore. My brother slowly pulled me off of him and changed positions to where his back was against the driver's door and his feet rested on my chair. Once settled, I returned to his cock. I kissed it up and down with small, soft pecks, and then I moved down to his balls. Sucking on each one, slowly rolling them around in my mouth. He really enjoyed this and started squirming. I giggled and returned back to his cock, taking it deep once again. I wanted to fit all of that fucker into my mouth! In this position I could watch my brother, while he watched me. I looked up and made eye contact with him and slowly sucked him up and down. "You love your brother's cock, don't you?" He said.
