Winner Takes All

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Addie gets more than she bargained for after losing a bet.
4.4k words
4.19
77.5k
51

Part 1 of the 2 part series

Updated 09/29/2022
Created 07/24/2014
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Laura Matthews didn't talk to me for a week after I turned down her invitation to go dress shopping for our junior-high school dance; Lisa Thornton in the ninth grade only wanted to talk to me when she needed someone to vent to about her latest fight with her boyfriend, mom, or little brother; and Christina Morritz spread ugly rumors about me sophomore year because she was insecure about her own self. All of them were ex-best friends and a glaring reminder why I didn't hang out with girls any more. My junior year of high school I finally found my kind of friends: Lyle, Joey, and Conner, all graduating seniors and a solid replacement for each girl friend I had lost. They had already been friends for years by the time I stumbled across them but the four of us had been inseparable. My name is Adeline Andrews and back then I was one of the guys.

Most people considered me a tom-boy. Sure I wore cut off shorts and tank tops that showed off my figure but that was only around my house when it was too hot for anything else. More often than not, though, I wore baggy band t-shirts and jeans. I had no problem telling crude jokes or going on grand adventures or playing video games. This was what allowed our friendship to work. The guys appreciated that I could keep up with them, that I was just like them.

As the years went on, the four of us grew closer and closer. My mom had met them and eventually became comfortable with the idea of me going out with them, even staying over at their houses sometimes. They were as protective of me as a group of older brothers, which she had to admit gave her peace of mind. Even though I was tough, it made her feel better to know I had three strong guys looking out for me. It was a good thing she couldn't read my thoughts though, because if she had known about some of the ideas going around in my head about them, she would have changed her mind in a heart beat about letting me run with them so often. I wasn't like other girls but I can say I had one thing in common with most: I fantasized about boys very, very often. To have three attractive boys around me for hours on end almost every day of the week was both a nightmare and a dream come true rolled into one.

While hanging out with Conner, watching a movie stretched out on his bed, my mind would suddenly wander into an alternate reality where we are having wild sex there instead. My imagination was so vivid, I would swear I could feel him inside me, feel myself nearing an orgasm and had to clamp my lips together to keep from reacting to it. All the while, right next to me, unsuspecting Conner just watched the movie. The same thing happened when I was with Lyle. Any time he touched me, whether it was a hug, an arm around my shoulder, or even if he only nudged me to get my attention, I got hot and excited, envisioning those hands feeling me all over: groping and pinching and teasing. Joey wasn't a part of these fantasies. He was the 'quiet one' every group of friends has. The one who is the nicest, most responsible when things get serious, and most well mannered. It was hard to believe he would say something even remotely sexual, let alone do. When I first imagined sex with him it felt...wrong, as though I was forcing him to do things he didn't want to do by having him appear in my fantasy. I left Joey out of it then and focused solely on dreaming of Lyle and Conner. Time and again I had to wonder, with the way they sometimes looked at me or where their hands would drift to when they tickled me, if they didn't dream of me, too.

On a sultry afternoon in June, the four of us sat camped around a wide screen TV in the shoe box Conner and Joey called their apartment. It was Joey's birthday; he was the last of the guys to turn twenty-one. Even though I was only twenty, and therefore by law still a minor, I had been invited over to celebrate with them by cracking open some cold beers, eating pizza, and spending the whole day just playing video games. The apartment was filled with the clicks of mashing buttons, outraged grunts, victorious jeering, and the occasional slurp of beer stolen in between games. I had never had beer before and was thrown off my first sip for expecting it to taste like crème soda, but to keep up appearances I kept drinking, although only taking baby sips.

The air conditioner was broken so as it got hotter, not cooler, with the sun setting, I began to feel myself glisten with sweat. Conner was happy to take my controller when I handed it to him, which gave me a chance to make some adjustments. The hair scrunchie on my wrist wrapped around my shoulder-length blond hair, securing it in a messy ponytail on the back of my head. With my hair up, I could feel the gentle winds from the open window on my face. But I was still too hot. My t-shirt had to go. I swept the shirt by the hem over my head, my chest still covered by the plain black tank top I wore underneath, but just barely. It was a bit on the small side with thin, loose spaghetti straps. It covered my tits but not without showing a little off the top. After the shirt passed from in front of my eyes I could see that the guys had paused the game and were staring at me, each one half grinning.

"Don't let us stop you," Lyle said.

Rolling my eyes, I said playfully, "Shut up, I'm done."

"Are you sure," Joey said with a slight pout. "Maybe you're too hot in your jeans, too?"

I gaped. "Don't you start," I said, throwing one of the pillows on the couch at him. "You're supposed to be the good guy." He grinned my way to let me know he'd only been kidding. Neither Lyle nor Conner gave any such indication. My skin prickled as one of my fantasies sprung to life, this one involving both of them taking me at once, but I forced the images of Lyle bending me over the arm of the couch and Conner passionately kissing me out of my mind. There was no way I could get away with it when all three of them were around, someone was bound to notice my reactions. Later, I promised myself.

Reluctantly, the boys returned to playing, in Lyle's case watching, the game. I felt a lot better free of the heavy cotton prison that was my t-shirt. The breezes coming through the window wrapped themselves around my bare shoulders, skated across my partially exposed chest. We went back to joking and being buddy-buddy, but I could tell me removing my shirt had reminded all of them I was a girl. There seemed to be no end to the smirks and sideways glances where their eyes would move up and down, Joey's too! I would be lying if I said I didn't like the attention. No one had ever looked at me, boyish, stubborn, plain ol' me like that. I had a nice figure, I guess, but the way I kept it covered up no one would ever know. Their wandering eyes were fodder for the fantasies. A steady throb began between my legs that I took great pains to suppress.

When It was time to trade off controllers, Lyle and I went head to head. I hadn't been winning very often. Without any type of console in my house I didn't get as much practice as the guys. However, the alcohol having dulled his senses, I managed to beat Lyle in a fighting game by a hair. As was customary, I began my victory speech.

"Better luck next time, Lye." I gushed, giving him a smug grin. He rolled his eyes up and spoke to the ceiling.

"One time in a million and she starts gloating," he said. "It was luck."

"No way, dude! You had to put in effort this time and you still lost. I've gotten better at this game. Better than you, even." An inciting 'Ooooo' went up from Conner and Joey. What I said was the overstatement of the year, but I couldn't help feeling smug and kept going on and on.

"You couldn't win again." Lyle took up his controller from where he let it down after he'd lost.

"Is that the ungraceful loser's way of asking for a rematch?" My beer sat on a coffee table beside me and as I took my time sipping from it, Lyle's fingers tapped against the floor, impatient.

"Are we gonna play or not?" He was trying desperately to hide his smile, to seem genuine about his annoyance, but my cockiness was too ridiculous, even I knew it. "Unless you're scared to be called out, of course," he added.

My tone nonchalant, I said, "I'm not scared, only thirsty. Can't a guy take a drink?" I picked up my controller, pressed the start button, and waited for Lyle to do the same, but he didn't. A glance in his direction revealed that he wasn't even looking at the screen anymore.

"Thinking about what I want if I win," he explained. Ah, low stakes gambling. Just what we needed to spice things up. And if Lyle got to make a bet, I did, too.

"I know what I want: bragging rights for the rest of the month," I said without hesitation. Lyle seemed unconcerned.

"And when I win...you have to do what ever I say for the rest of the night." I had to think about that one. If I lost, did I really want to be subjected to any of Lyle's embarrassing tasks. He'd probably tell me to dip my toe in the toilet, drink week old milk that Conner and Joey were sure to have kept in the fridge, or dance around with ice cubes in my pants. Nevertheless, I had run my mouth too much to turn back now. We shook on it. On three, he pressed start and the game began again. Although I fought hard, at the end of three rounds it was Lyle who landed the finishing blow to my fighting avatar. Player one wins/Player two loses glared out at me from the split screen. The guys erupted, howling like baboons. I sat back against the coffee table and waited, sipping on the beer I'd been nursing all night, casual as if I hadn't just made a raving ass out of myself.

At the end of their celebration, Lyle sent a smirk my way, a playful gleam in his eye.

"Ready to meet my demands," he said.

"Lay it on me." I tried to seem unaffected, bored even, but the humiliation that was sure to come was having an affect on me.

"Remember, you've got to do everything I say, otherwise you're a punk who-"

"I know that, Lyle. I'm not a sore loser. Unlike you." I added with defiance if only to show them that I wasn't going to mope and guilt him into letting me out of my end of the bet. "I'm not a wuss."

"Okay then, Miss Not-A-Wuss, go get us all some more beers. Chop chop." It was plain he had had too much to drink, all of them had, but I rose from my place on the floor and headed to the kitchen. When I returned painfully cradling three ice cold beers from the fridge in my bare arms, I found the three of them now huddled together on one couch, Lyle in the middle, whispering in low, conspiratorial tones. Clearing my throat dramatically to break it up, I passed out the drinks.

After the beers were opened and the boys had guzzled from them with earnest, I asked, "Now what?" They exchanged one last glance, Joey's natural peach complexion blossoming to rose red, before focusing their attention on me.

"Dance," Lyle said. He folded his arms behind his head, leaned back into the sofa, and waited. When I didn't move he said, "Is there a problem? Dance. No, it doesn't matter how. I know there's no music, just-" Lyle sighed, fed up with my stalling. He picked up the game controller at his feet and with the press of a button, the game's main menu with theme music began to play on repeat. "Now. Dance."

What else could I do? The fact that it hadn't been what I was expecting him to tell me didn't mean anything. I danced. It also didn't matter that I couldn't keep on beat with the music or that I wasn't really dancing, just hopping awkwardly from one foot to the next. The guys had their eyes trained on my bouncing chest. As I mentioned, the tank top I wore was too small, hardly able to contain all of me, and as I moved I could feel my tits ready to pop over the neck line. There was nothing I could do to change that, though. If I stopped dancing or even tried to pull my top back into place, I would be severely chastised for doing anything other than what Lyle had told me. Or maybe I just made that rule up myself. Maybe I wanted them to see; there was no doubt they, a bunch of drunk, horny boys who had had a taste of me and wanted more, wanted to see. In any case, even though I felt a little uncomfortable, it was a lot of fun to hold them entranced as I moved my body. I noticed their hard-ons pressing up against their jeans; noticed their hands eagerly stroking through the denim but itching to touch me and that was when the realization set in that for once I wasn't pretending; this was reality. The excitement was mounting in me. I got more into it: shook my hips, tossed my hands up.

"This needs real music," Joey decided. He shut off the TV and pressed a button on a stereo system in the corner. As he resettled on the couch, his hand again massaging his crotch, a bassy R&B song filtered out of the speakers. It was just the thing to put me even more in the mood. I pulled off the scrunchie, my hair came tumbling down my shoulders. With a few more hops, as I had predicted, my tits, still held securely in a red full-cup bra, popped over the neck line of my tank.

"Take it off," Lyle was quick to command. Still dancing, I began to dispose of the scant top in the same way I had my t-shirt, rolling it up from the hem over my head. The guys watched in rapture, and their attention motivated me to get creative; suddenly, I wanted to see how well I could do in exciting them. Would it be as easy as they had excited me; as easy as I had imagined?

I had seen girls in movies doing all kinds of moves that guys liked so, taking a page from them, I strutted up to Lyle and turned my back to him, shaking my tight ass just inches away from his face. I was no expert and I know it might have been a bit awkward at first but, once I got the hang of it, I fell into a rhythm.

Lyle's hands took hold of my hips. He eased me in closer as I bent low, my hands on my knees for support, and shook to the music. His hands moved in circles on my hips, he caressed and slapped my ass again and again. The spanking did things to me. My smile, along with my arousal, grew.

There were more hands on me: squeezing one reddened cheek and the other, slipping between my legs to rub my clit through my baggy jeans. Feeling almost painfully aroused, I glanced over my shoulder to see the guys' expressions while they explored me.

"Wow," Joey's voice was little more than a whisper. His hand was the one massaging between my legs, I was shocked to discover. Of all the guys, Joey had been the most direct. "I don't believe it," he said, "There really is a girl under here." His finger slid further down my slit, as if he were trying to insert it into me through my clothes. My breath caught in my throat.

"Maybe," Conner joked, giving my right ass cheek a squeeze. "But she still moves like a dude."

"What does that mean," I said. It was strange but, all of a sudden, while shaking and dancing half naked before the guys, being referred to as a dude was an insult.

"It means you aren't using the right parts," Conner explained. "I'm barely hard at all."

"I feel the same. Only one way to fix that," Lyle said. That meant a new command was coming. "Okay, Addie, stop dancing. Turn around, face me." I did. "Take off the bra. Slowly."

For convenience, I only bought bras that unhooked in the front which I was grateful for at that moment. Conner wants to get hard, huh, I thought as my fingers toyed with the clasp. Let's see how he likes this. In one fluid motion, I unhooked the clasp and turned my back on the guys. The cups fell to either side. To the sound of zippers, I let the straps slide down my shoulders, then tossed the bra over my head. Out of nowhere, an odd feeling washed over me; a mix of feeling free and attractive, but also nervous. Not only had I never shown my naked body to anyone before, I was scared to know what the guys would have to say about it. I gave myself a quick critique. My 34B tits were round, full, and sat low on my chest; large, flat areolas the color of milk chocolate with erect nipples sitting in the center. Would the guys approve? Pulling in a steadying breath I turned slowly, my chin high to face them and their exposed, hard cocks. It was only a second as the guys took me in then began to clap. It was a slow clap of awe. Instantly empowered by the reaction, I gave a little wiggle.

"I've got to taste those." Lyle didn't waste time; he hoisted himself up from between Conner and Joey, grabbed me around my waist, lifted me off my feet, and stumbled backward to crash down on the other sofa so that I landed on top of him, on all fours, with his face pressed against my soft, fleshy orbs. His tongue extended and traced a circle around my areola, a sensation which left my nipple tingling. He did it again and again and finally took the nipple into his mouth, sucking. Leaning over to hold myself up with one arm, I bravely went in for a little action myself. My free hand dipped into Lyle's jeans, already unzipped and unbuttoned, and drew him out. My hand closed around his dick and pulled on it gently, jerking him off. He hadn't been expecting it; his hands gripped my ass suddenly. From there, one arm wrapped around my waist, holding me in place, the other snaked up to my other tit where he pinched and squeezed the sensitive nerves, then rolled my hard nipple between thumb and index finger. I gasped, my head rolled as far back as it could go, then turned to the right where I caught sight of Conner and Joey, hard dicks in hand, as they furiously stroked; their eyes locked on me.

Conner was bold. He didn't want Lyle to have all the fun with New Addie, and rose from the couch to join in. He towered over me with his dick in my face, poking at my lips. But, stubbornly, I wouldn't let him in. After all, he hadn't been the one who'd won the bet.

"Lye," he complained. I didn't let Conner have any part of me until Lyle, reluctantly, removed my tit from his mouth just long enough to order me to take him, then resumed suckling me. My mouth opened. Conner eagerly shoved six and a half inches of throbbing cock inside the warm hole and began thrusting, his hand on the back of my head, fucking my face as though it was the only chance he'd ever get at pleasure. The smooth head brushed the roof of my mouth, the tip of my tongue grazed his shaft over and over as he thrust in and out. My lips tightened around him. I had never sucked dick before, but Conner's deep, throaty moans told me I was doing it right.

That was when I felt a tug at my jeans. It was Joey. Soft spoken, mild mannered, Joey hadn't even bothered to ask Lyle's permission. I began to realize that maybe he was the most sexual of the three of them and he'd fooled us all. There was nothing stopping him. Lyle wasn't paying attention, my hand was supporting me while the other tugged Lyle's cock, and my jeans were loose; no tight skinny jeans for this tomboy. Joey was able to get them down around my knees in seconds. Oh well, he was the birthday boy after all. He could have his fun. On all fours, I was in the perfect position for him to deliver a sudden spank to my panty clad ass. It made a crisp, loud smack and sent a jolt through me like blast of electricity. I grunted from the pain, but trembled from the pleasure, dipped my chest lower and rocked back toward him for another, which he gave me. I was too happy to receive. After each slap, Joey would gently rub the feeling out of my cheeks so as not to hurt me too badly, and gave me more as long as I kept signaling I wanted more.

My panties dampened with moisture as my arousal grew. I felt beyond myself, unable to believe that what I had been waiting for all along was happening. These friends of mine, almost since as soon as I'd met them, were meant to have me this way. Soft, restless moans, even with my mouth full, forced themselves out of me while the thrill of what I was doing shook me all over. I wanted more, wanted Lyle to take it even further. Sure enough, after about ten minutes, Lyle spat me out and addressed us all.

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