Bad Bets

Note: So as per usual, this story is heavily centered around anal with some light free use elements though NO ACTUAL SEX SCENES HAPPEN since I was more interested in dialogue, attitudes and the scenario. If that doesn't do it for you just skip this one. Also, I doubt I'll ever do a story from the girl's perspective again.

*****

Opening the door, I was greeted by Dan as usual; the others never could be bothered being the ones to answer it. "Hey, look what I brought," I said, holding up a case Double Brown with a smile.

"Hey yourself," he said. "A pretty girl that always shows up with beer, have I ever told you you're amazing?"

"Yes, but I think it could do with repeating."

Walking inside I'm greeted by Dan's other three roommates sitting around watching the match with a chorus of mumbles. Rick and Nathan look over quickly before turning back to the screen while Karl's eyes linger on me longer. Usually, I wouldn't blame a guy for it, usually. But the way Karl was so obvious and intent about it rubbed me the wrong way. I gave him a flat smile and hoped he wouldn't try talking to me.

It didn't work. "Careful, you keep coming over and we might think you're in love with one of us," Karl said.

"Please, I just want someone to watch the game with; you know how my friends are," I said. It was true, the only reason I went over to Dan's so often was because none of my girlfriends were really into soccer but he and his mates, except Rick, loved it; coming here just beat watching it alone.

Tossing the beers to each of the guys, I take my usual spot next to Dan on the couch and settle in to watch the soccer World Cup.

Just 11 minutes into the game, Germany managed to score the first goal to all of our surprise. "Wow that was fast, aren't soccer games supposed to be slower? Don't these things usually end with like 1-0 or 2-1?" Rick asked.

"Yeah, usually," I said with a frown. "I mean it still could, just because they got one now doesn't mean they'll score every 10 minutes. Brazil's still got this."

"Well aren't you confident. You don't think Germany has a chance?" Dan said.

"They've got a shot, but c'mon, soccer's like the only thing Brazilian's have. I say they've got it."

"Oooh, you know what? Just for saying that, I hope Germany wins," Dan said with a smile.

"Pffft, hope is for wusses, how about we make some bets instead?" I said with some bravado.

Dan raises a brow. "Oh? What do you have in mind?"

"Hmmmm, how about this; if Brazil wins with two, you chauffeur me around for the next couple months?" I said.

Rick piped up. "Hey it'd be really convenient if you won that bet huh? Since your license is suspended for the next two months and all, that's a real coincidence you came up with that number."

"Thanks Rick," I said.

"Fuck off, that's a shit bet," Dan said giving me a look. "Like you said, soccer's all Brazil has, that and corruption. Sorry Grace, I'm not biting."

"Come on, it's not that bad, Germany's odds are like 5-1. Just ask for higher stakes, don't be a little bitch Dan."

"Nope, not happening, you can go suck my dick, I'm not driving you around for two whole god damn months."

"Alright. I'll do that," I said after pausing for a moment to think it over.

"Do what?"

"I'll suck your dick"

"What?"

The guys turned and stared at me. Blushing a bit, I repeated myself. "You heard me, you win and I suck your dick." I didn't really want to, but the odds were on my side and public transport fucking sucked.

"Seriously? For a bet? Grace we've been friends a long time, don't you think that would make things weird between us if I win."

"Only if you make a big deal out of it. It's just a blowjob Dan, you don't need to freak out about it." I didn't know if it was the beers, the fact I enjoyed a bit of gambling or something else, but the idea of gambling my body was kinda doing it for me and before I could even stop and think about what I was saying, I added "besides, think about this mouth on your dick and my pretty face looking up at you." I even made a show of it by opening my mouth and sticking out my tongue, letting a drop of spit fall on my shirt.

I noticed Dan start breathing faster and Nathan elbow him when he didn't say anything. Guys are so easy.

"Alright, so how about, if Germany wins with two, you-then I win the bet?" Dan said, finally finding his voice.

"Deal," I said quickly, confident that Brazil had it.

The conversation and jokes had stopped; instead everyone was now watching the match with quiet intensity. 23 minutes in, the quietude was broken when Dan started laughing while I was gulping nervously. I wasn't so sure Brazil could claw its way back with three more goals now. Despite what I'd said I didn't actually want to suck Dan's dick. Stupid alcohol, stupid gambling.

"Uh, Dan? How about we change the bet?"

Dan looked over at me with a smug smile. "What, feeling nervous? Not so confident anymore?"

"No that's not it, a bets a bet, I just... thought we could make things a bit more interesting and go double down or nothing," I said, refusing to take the bait.

"Okay, let's make things more interesting then. How about if Germany manages to score three, you let me fuck you?" Dan said, keeping the mocking smile on his face.

Looking for a way out, I figure this at least gives me a shot at getting away so I agree. "Deal. But if neither side gets a third then the bets over and no one gets anything yeah?"

"Yeah, that's fine Grace, bets over if neither gets three." Dan could've said no, but he let me off the hook instead. I don't think he actually wanted to force me into anything, he was just teasing me with the new bet.

"Dude," Karl said shaking his head. "The fuck?"

Less than a minute later, my mouth was open. I was back where I started, just in a deeper hole.

Dan turned slowly to face me. "Hey Grace, look you don't actually have to, we're just messing around, I was just fucking with you before," Dan said sympathetically.

Karl punched Dan in the shoulder. "DUDE!" Dan ignored him.

I should've swallowed my pride and agreed but I didn't. "No, no seriously you don't have to do that. I meant what I said before. I'm not gonna try worm my way out. I was just thinking, maybe we could change the bet again? Double down again?" I said.

"... Grace," Dan started.

Cutting him off "Dan. How about, if Germany gets a fourth I'll... I'll let you fuck my ass instead? You game?" I said trying to project confidence and probably failing miserably.

I saw Dan gulp hard and the rest of the guys give each other looks.

"Grace... I think we should just call it quits. This has gone far enough, this is all just a piss take right? No need to dig a deeper hole or keep up the charade."

"It's not a charade, if I make a bet I'm going to keep to it. I just want to make things more exciting is all." Argh! He's giving me a pass! Why couldn't I just take it? Instead I said "Look, ever since you broke up, you've moaned about Lily never doing anal, you've clearly got a thing for it and I'm saying you can do it with me, you can fuck my ass. I know you've been trying to get inside any girls butt for the longest time, but now that one's offering, you're gonna say no? C'mon."

Dan was breathing heavily now but still seems reluctant to take the bet. I shouldn't keep pushing him, I was just making this worse for myself by saying that stuff but I can't help it.

Dan breathes out and shakes his head. "This is insane."

The other guys were keeping quiet and listening intently to our conversation while trying to covertly hide the pitched tents.

I don't know what came over me. "You know, no one's been up my butt before. It's unexplored territory! But you could be the first," I said with a laugh. "How often are you going to get the chance to be the first up some poor girl ass?" That did it, I could tell Dan's cock was now firmly at the steering wheel.

"OK," Dan said finally after a painfully long pause.

Two minutes later, just 26 minutes into the game the scoreboard read Bra 0 - Ger 4 and I couldn't believe the universe was trying to fuck me so hard.

Having gotten ahold of himself, wrenching the controls away from his cock, Dan went back to his nice old ways and tried to let me off the hook. "Grace. OK seriously, this has got to stop, this has gone too far."

"No Dan, I-"

"Nope, don't care, I'm done, I'm out of the bet, I officially forfeit, it's over Grace," Dan struggled out the words with difficulty. I felt a wave of relief hit me but at the same time... there was also just the tiniest bit of disappointment.

Which was when Karl spoke up with a grin. "Hey if Dan doesn't want to go through with the bet I'll take it." I wanted to punch him in the face. "Yeah, let's double down again like before. Say if Germany gets a fifth, how about you let all 4 of us fuck you in the ass? What do you say Grace? You game?"

"What? You're not part of the bet Karl, you can't do that," Dan shot out. "Grace don't say anything, it's already over, it's too late."

"No Dan, I told you it was fine, I don't want to be given an out... I just like raising the stakes is all." Why, why, why, why, idiot!

"Alright Karl," I said with my heart absolutely pounding out of my chest and against all better judgement. "You've got a bet, all four of you can have a turn in my asshole if Germany scores a fifth."

Despite the previous bets, I still held out hope. Bad luck, good, they didn't exist, they were something our brains made up. The prior results had no bearing on the future and I knew how unlikely five goals were during a world cup was.

"Who gets the first turn? Do we get your ass for the whole day or what? Where are allowed to cum?" Karl asked giddily.

"Slow down asshole, you haven't even won the bet yet."

"Yeah that reminds me, do I have to go slow or can I just go all out on that tight little hole of yours?" he goaded with a grin.

"You get to go last," I said tersely. "A turn means you get to cum once. You can... cum either on my ass or inside it but that's all." I reluctantly clarified. "Please go slow," I whispered out at the end pleadingly.

"Thanks, good to know, just wanted to get the ground rules laid out for everyone," Karl said in a tone that implied he hadn't heard or cared about my request.

Three minutes later my face was buried in my hands. "Oh fuck me," I groaned out.

"In the ass right?" Karl annoyingly added.

I snapped my head up to glare at him. "Yes in the ass. You and three other guys get to take turns fucking my ass okay? Unless you want something more, unless you want to raise the stakes again?"

"Nope, I'm good."

Thinking he would agree, I was surprised to hear him say that. "What?" I asked lamely.

"I said I'm good here. So, when can we collect?"

"Pussy," I said, hoping to goad him back.

"No thanks. I'd rather give your ass a workout."

Karl was annoyingly pleased with himself. Before it could go any further though, Dan spoke up. "Yeah sure let's raise the stakes again."

Now it was Karl's turn to be outraged. He snapped his head around to whirl on Dan. "You left the bet, you can't do that."

"I changed my mind. Grace, you wanna up the stakes?"

"Yeah," I said, looking at him gratefully.

Karl broke in. "Fine, fine, fine. But if we raise the stakes again it better be proper high this time. If Germany gets a sixty then..." Karl paused to think, presumably trying to come up something awful for me to do. After a long pause, his face broke into a cruel smile. "You let me film the whole thing as a porno and put it up online."

"Fuck you. That's ridiculous, I'm not ruining my reputation letting the whole world see my face and watch four guys take turns on my ass! That's going beyond too far."

"Fine, fine, then you can wear a mask, I'm not sadistic you know. You just can't look miserable the whole time. You have to give us the whole pornstar treatment and act like a massive whore. What do you say?"

Dan flashed Karl an angry look. I felt like I should say no, just cut my losses and run but the odds were in my favor... Then again, they were the last five bets too and that certainly didn't help at all. Eh, it was another chance at getting out and the stakes were essentially the same as the last bet only I had to do a little slutty acting.

I gave Karl and irritated look. "Fine, if Germany gets a sixth, I'll star in your little porno. I'll call myself Anal Annie and play your buttslut. You can do that whole bullshit pre porno interview and I'll say all the right things. Hell I won't even touch my pussy the whole time; it'll be like my shtick, I'll be the girl who can only get off on being an anal only whore. Happy?"

"Hmmm could do with some work, but yeah, I am."

This time, more than half an hour passed without a goal being scored. I breathed a sigh of relief. Karl looked like someone had shot his puppy. Dan, Nathan and Rick all looked disappointed too, not that I could blame them but they did their best to keep a lid on it. My relief lasted ten more minutes before it was shattered as Schürrle scored a sixth in the 69th minute. I felt like screaming. Dan turned to give me a sympathetic look. Karl was now grinning from ear to ear, while Nathan and Rick were both just trying to keep their emotions masked. I was just about to speak when Dan beat me to the punch. "How about we raise the stakes again?" I felt like kissing him. Karl groaned loudly.

Before I could agree, Karl interrupted. "Y'know, talk is fun and all, but Dan's right. It's just a charade at this point. You won't actually let any of us cash out, and even if you pretend to, Dan will just save your ass by saying he wants to keep upping the bet. Why even bother pretending, you'll just keep changing the bet until Germany can't score again. We may as well just stop talking about this whole thing right now," he said bitterly.

I kept getting outs but kept refusing to take them. Before I could stop myself, I found myself making up an excuse. "How many times do I have to repeat myself, it's not a charade. You want to cash out, right here, right now, fine. I'll do everything we talked about before with you; the porno, the anal, the video, all of it, but you'd be missing out."

That got a confused look from him, I continued. "You can stop here now, but I'll just be a dead fish the whole time if you do. See, all the bet says is I let you fuck my ass, but that's it, doesn't say I have to make it fun. But if you take the next bet, I'll take instructions, do anything, anyway you like. Look it's obvious you've got a thing for my ass, imagine waking up, inside it." That perked him up. "Think about what it means, if you take the next bet and win, I'll come over to your room every morning and jerk you off with my ass if you tell me to. So either I'm gonna lay there not moving a muscle, or you could make me beg for it. Tell me to act like a slut and you won't even know if I'm doing it because I have to or because it's what I'm really like, imagine me being Anal Annie all the time. So, how about it? Cash out or keep going?"

Seeing Karl struggle with himself I knew my little speech had done it and gave me another shot. "Alright, let's keep going," Karl ground out after a pregnant pause. "But those stakes still aren't high enough. It was a nice speech, I'll give you that. But what it ultimately amounts to is just taking instructions, lots of risk without much gain on. You have to up it."

"Up it? Up it how? I don't really know how I can raise the stakes any further," I said genuinely confused. "I've never done anal with a guy before and now I'm agreeing to make an anal only porno for you all, I figure that's about as high stakes as you can go."

"Well you figure wrong because I've got an idea. If they get a seventh, you have to be our personal slut for a week. Any hole, anytime, anywhere, any way we want, on top of the taking instructions. Sound fair?"

"Fine," I said tersely. "You win and my holes are your property for the next seven days then." I just had to keep getting them to agree to change the bet and I'd be fine. My bad luck would eventually end; Germany would fail to get any more goals eventually.

Karl finally perked up at that. "Soooo, if I only wanted assfuck you every day?" he said.

"Then I'd bend over and let you," I replied with a sigh.

"And what if I wanted to get a blowjob after," he said with another savage grin. The implication was clear. He wanted ass to mouth. I wasn't sure if Karl meant it or was just trying to freak me out, but seeing this side of him just made me reaffirm my opinion of him.

Gulping hard, I replied "Then after you finished reaming out my asshole, I'd suck you off of course."

"Huh, sounds like a lot of fun." With the drama over, we went back to watching the game intently.

Ten minutes later, in the 79th minute I had my face buried in my hands again. "Fine! A month! A whole month! If Germany gets an eighth, I'm your personal prostitute for a whole month; you can even share me around with other guys if you want. No limits whatsoever for this one, anything sexual goes. Guys?"

They all just nodded slowly. The next 11 minutes were the slowest of my life. Every play meant the world to me, but thankfully nothing else happened for Germany. In the final minute, just when I thought it was all over, another goal was scored, but this time by Brazil. I was finally off the hook. The 5 of us all slumped back into our seats for different reasons.

Dan broke the silence. "Well that's that then. It was fun while it lasted."

"Knew it was too good to be true," Karl added bitterly.

Nathan and Rick just grunted in response.

I expected to just feel nothing but relief, so it came as a surprise when some guilt came along with it. Dan and Karl had called it, it was just a charade and I was just trying to worm my way out of the bet. And they'd let me the whole time. Again and again they pretended to buy my bullshit and let me off. Sighing to myself, I thought there's only one thing for it then. "I'll still go through with it."

The non sequitur took the guys by surprise, but eventually Karl was the first to respond. "What?"

"You were right. I was just trying to get out of the bet. That wasn't cool, so I've decided I'm just gonna go through with all of it anyway."

"Seriously?" Dan and Karl chorused.

"Yeah," I said slowly. "Though I'm probably gonna regret it knowing what you plan on. Look Karl, I'll try to keep to my word as much as I can, but the stuff we were saying before, it was just talk. I've never done anal with a guy before and only three things have ever been up there. That stuff you said, you really can't just do that, it'd... It'd be really bad for me."

Karl wiped the smirk off his face and seemed to consider what I had said. "Sure, maybe not right off the bat on day one. But day 29? That's a whole other story." Ugh, and here I thought he was gonna surprise me by saying something nice.

Nathan had been almost completely quiet the whole time but finally spoke up now. "Grace, really? You're really going through with this? You're going to let the four of us just... do whatever we want to you?"

"A bets a bet." I turned to look over at Dan for some support but he seemed different, he's never looked at me that way before. I was about to ask what was up when he suddenly pulled down his pants and took out his dick, right there in front of all of us.

"Well, best to get started at the beginning, right?" he said.

This could be trouble, I thought.