I Bet...

The following was requested by totesanalt and therefore I cannot claim that the original idea was mine. Posted here with their permission.

***

I opened the door and there was Connor. "Hey Janet. Is Winnie home?"

I groaned. My roommate's four-week romance with Connor could best be summed up in a series of loser moves on his part. Pestering her for a date like a friendly puppy? Loser. Being so poor that he expected her to go dutch? Loser. Not treating her a princess like he ought to? Loser.

Leaving her alone with Dwight 'The Chadmaster' Davis right after he'd abandoned her at a party due to some 'family emergency' bullshit? Well that had turned out to be the biggest loser move of all.

I smiled at Connor in a way that that communicated that he wasn't welcome and that he should vacate the premises immediately. Connor, though, was apparently an idiot as well as a loser. "Is she home?" he repeated. There was a gleam in his eye that was completely at odds with the way he'd been spectacularly dumped. He gripped something in one of his hands; a poker chip, battered and scarred, with the red-and-blue colouring faded from age. His fingers rubbed it's faded sides.

I frowned, adding 'weirdo' to the list of descriptions I had filed away for Connor. "She isn't here. And even if she was, she doesn't want to see you."

His lips pursed into a petulant frown. "When is she coming back?"

I kept that 'fuck off' smile on my face even as irritation flared inside. "I wouldn't bother. Winnie's dumped you for a real man. Didn't you get the memo?" It had actually been a pic sent via WhatsApp of her being cuddled topless by Dwight- taken by yours truly- but never mind. "Now would you kindly go back to your parent's basement where you belong?"

His face crumpled a little under my cheerful aura of contempt. Harsh, but once he knew his place it would be better for him in the end. I turned away and moved to shut the door-

"I bet," he said suddenly, every word slow and uncertain, "that you won't invite me in."

I paused, the door halfway to closing. I frowned.

And then I turned around, sneering. "You think, what, that I wouldn't invite you in?" I laughed. "You think I'm afraid of you? Come on in then, little puppy." And with that I opened the door, one arm flung out wide in an exaggerated gesture of welcome.

The idiot stared at me and then down at that ugly-ass poker chip. He stepped into our lounge room as though expecting a trick. "Why did you let me in?"

"Because," I said, "I wanted to see the dazed expression on your face when I proved you wrong."

He nodded slowly and said, "You've always hated me, haven't you?"

I just smiled and shrugged. A second later he said, "I bet that you don't have the guts to tell me why you hate me and what you said to Winnie about me."

Easiest bet I ever took. "Fine," I said. "You really want to know? Yeah, I told Winnie that you were a loser."

"A loser?"

"Look, Winnie's like me. She deserves a winner, you know? Someone rich. Fit. Popular. Someone who can treat her right."

"Winnie didn't care about that stuff."

"Well, my girl Winnie's got some odd notions about romance. So I took her aside and explained to her that she was too hot and too popular to settle for a guy like you."

"You mean a loser like me." His eyes narrowed. "You introduced her to Dwight, didn't you? To break her up with me."

I said in my sweetest voice, "No hard feelings, right?"

"No hard feelings?" He closed his eyes and then gave a weird little laugh. "You're making this all too easy for me, you know?"

"What?"

"Nothing." He gripped the poker chip with a sudden intensity and said, "Janet. I bet that you won't show me your boobs."

I laughed, shocked. "I'm sorry?"

"You heard me. I bet you wouldn't show me your naked boobs."

Shock turned quickly into disgust. I was proud of my boobs. They were full and firm and glorious to look at. Men couldn't help staring at them when I entered a room. My boobs could cause traffic accidents. They once had.

My point was my boobs were awesome and thus reserved for real men. Handsome men. Rich men. Winners. Not sad little Connor.

On the other hand...

Connor stood there with a strange little smirk on his face. Did he really think that I'd chicken out? That I wouldn't do it?

Did he, and this was what really pissed me off, think that he was going to win?

I said, "You know what I bet? I bet I'll show you these babies and you'll drop dead from a heart attack." I let my hands move down to my shirt top and, with a single careless motion, pulled it off over my head. He swallowed as I took off my bra. I posed, one arm cocked at my side, thrusting my chest out. I felt a thrill race down my spine at the sight of the silly look of shock on his face. "There. See?"

"Yeah," he said. "I see." He reached out to touch my chest-

-and got slapped hard for his trouble. "What the hell do you think you're doing?" I hissed. I kicked at him and he retreated, cowering, while I covered up. "You really think you deserve to touch me? Listen to me, you little shit-"

"I bet you won't let me grope your chest," he said quickly.

I laughed. "Seriously? You still going on about that?" I moved my hands away from my chest. "Don't think this lets you off the hook. You think I won't let you touch my boobs? Fine. Go to town. I'll be standing here, bored shitless." He frowned, uncertain. "Well?" I made an impatient gesture. "Go on, then!"

He stepped forward, licking his lips. Sighing, I grabbed one of his hands and pushed it into my chest. A moment later both were busy; fondling, touching, rubbing. From time to time he would massage my nipples, his eyes narrowed as though puzzling out some mystery.

I confess- for all that Connor was a loser, it felt good. Good to have my tits massaged- surprisingly enough he seemed to know what he was doing- but more importantly it felt good to win, to show him how little this all meant to me. As soon as he was done I could throw him out-

"I bet," he said, "that you won't take off the rest of your clothes."

"God," I said, "you really are pathetic, aren't you?" I turned my back to him, looking over my shoulder. "Enjoy seeing what you'll never have, sad boy." I unzipped my jeans and wiggled out of them before kicking them off. I turned around and hooked my thumbs through my underwear. I slowly pushed them down, revealing my trimmed pussy.

He stared at me in a way that made my skin crawl. I waited for him to get a good eyeful before muttering, "Show's over, little man. You got to see me all the way naked- congrats. Now fuck off, will you? I want to call my boyfriend over."

"Getting aroused?"

"As if," I said, ignoring the way that the satisfaction of my victories- coupled with his lingering touch- had created the tiniest trickle of heat between my legs. "It's just that after five minutes of talking to you I need to remember what a real man feels like. Don't you understand what all this proves? You're a loser, Connor. You'll always be a loser. I know it, you know it and Winnie knows it too. That's why she dumped you-"

He stepped towards me, fists suddenly clenching. "She cheated on me. Because you pushed her too."

For a moment I nearly stepped back. Then I rallied. "Yeah. So? So what? What are you going to do about it?"

He let out a long hiss. "I bet you... I bet you wouldn't fuck me."

Silence.

He added quickly, "and enjoy it."

I took a step back.

I took in a deep breath.

I let it out.

I thought very, very hard about where the nearest sharp object was and how I would go about disposing of his body.

"Fuck," I said, putting every ounce of venom I could into each word, "you."

"That's my bet."

"Go to hell."

"Are you giving up the bet?"

"You're a creep and a loser-"

"So you give up."

"Fuck you." I nearly shouted at him.

"Do you give up the bet?"

More silence. I should say no. I should throw him out on his ass. I should call the police. I should absolutely give up and lose-

"No."

"Sorry?"

"I said...no. I'm not giving up." I turned around and walked into my bedroom. I stood by the bed and waited while Connor stepped inside and stripped off, revealing a skinny frame, pale skin and a surprisingly long cock.

I could do this. I could fuck him and I could enjoy myself. Definitely.

...Probably.

He lay down on the bed. His cock jutted out like a pillar from his dark brown pubic hair. I stared at it and he said, "Chickening out?"

Right. If I was going to do this- and I still couldn't believe I was doing this- then I was going to have to do it right. Anything else would be losing.

And so I lay down next to him and I kissed him like he was my lover, like he was the most important person in the world to me; I kissed him like it was his last kiss on earth. I pressed my body against his, letting my lush curves rub against his sparse frame. My hands reached down and grasped his cock, caressing its length. His own hands roamed my body, exploring my chest, my ass. His lips moved to taste my neck and I moaned at the way he nipped at my sensitive flesh. One of his fingers gently rubbed my clit and the delicious friction sent shivers of pleasure through my body. Huh. I guess I knew why Winnie kept him around after all.

He tried to move but I pushed him down onto the bed. He made an awkward squeaking noise as I straddled him and gently impaled myself on his cock. One of his hands found my tits; the other continued to rub my clit as I began to roll my hips. Soon we found a nice, satisfying rhythm, our bodies syncing with each other as we rutted. He pulled me down and I kissed him again, our tongues twirling, our lips mashing. His finger was a gentle blur where we were joined, and I felt my pleasure rising and rising and rising-

There.

I moaned and humped against him as my orgasm claimed me. A moment later he pulsed inside my depths and the hot pleasure of my orgasm merged with the burning satisfaction of victory. We continued grinding against each other until at last I collapsed onto the bed next to him.

Connor was the first to rise, groaning. Reaching for the poker chip, he said, "I bet you don't want to be my girlf-"

I kicked him in the balls and the coin flew out of his hands. He yelped and hobbled over to pick it up while I snatched up his clothes and tossed it at him. "No more bets," I said. "I won, you lost. Now fuck off."

He stared at me for a long moment and I thought he might actually argue with me. Then he sighed and muttered, "Fine. For now." He grabbed his clothes and shuffled out. A minute later I heard him leave the apartment.

I lay back on my bed, naked and content. I was sticky with sweat and saliva and other things. There were hickey marks on my neck and Connor's seed trickled from between my legs. I smiled.

"Some people," I said, "just don't know when they've lost."