Bet Your Sweet Ass Ch. 01-02

Chapter 1

"There is no fucking way that the Suns are going to beat the Pistons, bro! Not gonna happen!" my sister, Natalie, asserted with no small measure of confidence, being the big Detroit fan that she was.

"I think that you're underestimating their new draft pick center, Lamont Rogers," I smirked.

"He's just a fool who skipped college to go straight NBA. We don't really know how good he'll be," my sister pointed out.

"He was in the Army and helped organize basketball games for Afghan boys and girls while there. He's not a lightweight. Trust me on that. I can feel it in my bones," I retorted.

"Okay, if you're so fucking sure that Phoenix will win, how about a bet?" Natalie taunted me.

"I don't bet money. I can't afford to throw it away, just in case I'm wrong, and I don't want to take your hard-earned dollars, either, sis," I refused.

"I didn't mean money, bro. I meant ... sexual favors," Natalie spoke that loud enough to wake the dead, certainly loud enough for our significant others to hear her.

"Excuse me? You mean like incest? Not to mention cheating?" I remarked.

"Hey, it's not cheating if I want to watch!" her boyfriend, Aaron Palmer, shocked me by grinning.

"Me, too! This could be hot! I could send a letter to fucking Penthouse or Family Affairs or whatever about the time that my boyfriend fucked his own sister and how fucking, steamy hot it was!" my girlfriend, Bianca Giordano, absolutely stunned me by going along with it.

"Woah, back up here, I don't mean vaginal sex, because that could lead to ... deformities and shit, at least with incest. What I'm talking about is sodomy. What I propose is that if Detroit wins, and thus I win, I get to peg my sweet brother as often as I wish. If Phoenix wins, and thus my dear brother wins, he can stuff his cock up my ass as much as he wants, with no stipulations except lots of lube ... which, of course, is a stipulation for the pegging as well should I win. Relax, bro, I'll be sure to give you a reach around, if you agree to play with my clit. So, how about it? If your girlfriend and my boyfriend are still okay with that?" Natalie licked her lips as she winked at us invitingly.

"So, for how long here?" Aaron inquired now, apparently curious and eager.

"Permanently. It would be a lifelong deal. Lifetime pegging rights to my sweet brother. I would so enjoy that. Even thinking of it is enough to make me wet ... we could take them along on our honeymoon and everything. You'd still be up to marrying me if that's the only exception to our wedding vows, right, dear? I mean, babe, it's not like he'd be pounding my pussy and you admitted that you find the idea of incest rather hot, right? It could really help keep things steamy in our marriage," Natalie worked her charm on her man, not that she needed much effort, given that Aaron had already signaled his approval of incest in principle.

"True. I am a bit of a voyeur and frankly something of a sub, but not really into taking it up the butt myself. Watching another guy do it, especially your brother, that's pretty kinky and hot," Aaron blushed a little.

"You just like me riding your cock and your face, isn't that right?" Natalie teased her boyfriend.

"You got me pegged, though not in that way," Aaron joked, making us all laugh, "Though I also enjoy your long legs. Damn, those legs are sexy as hell!"

"Quite the contrast to Nathan here. I love it when he pounds me from the back, does me doggy-style, and bends me over. If you lose, Natalie, you're going to experience pleasure like you've never imagined, hon. Trust me on that front. When he goes up my ass, oh, damn, it feels great! Dios Mio!" Bianca reminded us of her mixed Puerto Rican/Italian heritage for a second.

"Well, as a switch, and given that Aaron doesn't really go for anal sex, I won't deny that I'd enjoy being taken and used roughly up my butt. I can almost guarantee you that I would, as a matter of fact. It's a nice contrast and meets different needs, either way. It meets Aaron's and your need to watch, unless I'm wrong. It meets my need to either Top or bottom, depending on who wins. If I win, it would meet Nathan's need for a good prostate massage, if you will, not to mention sex where he could relax and submit, just enjoy it. I think that he would like that, if I had to guess. He's my twin, after all.

"If he wins, it meets his need for some strange booty and I suspect my tight ass would really bring him some pleasure, plus the chance to dominate and play the aggressor. Plus, being twins, we really should have some kind of intimacy between us, don't you think?" Natalie rattled off her reasons for going through with the bet, mostly to convince me, as our partners already seemed on board with it ... I was the only one with doubts, despite our sibling bond.

"So, this is just anal with some manual manipulation, as it were, either by handjob or by clitoral stimulation, right? Or are we talking general possession of the bottom, up to and including finger-fucking, fisting, and rimjobs?" I raised the stakes a bit to both gauge Natalie's kinks and test her mettle.

Natalie simply cracked a broad, lustful smile, stared at me a bit, and announced, "I'm game for total ownership of the booty. I like the way that you think. I mean, hell, when not at work or in public, I could keep you bottomless and get to stare at and fondle your butt as much as I wish. I love that idea. Let's work that into the bet. Great plan, bro, but it is going to backfire when I win. I'm going to really love rimming your fine ass."

"This would only work if we all lived close by, maybe even together," I observed.

"True, and that could be a great deal of fun," Bianca licked her lips rather lustily, "I might even go for a bet with Aaron that involves oral sex."

"Yummy plan, but I don't know what Natalie would think of that," Aaron replied nervously.

"Oh, don't be such a wuss and don't hide behind my skirts! We're not married yet and when we do wed, this will be a prior deal that we can grandfather in! If you want to put your mouth where your mind is, go right ahead! What shall it be, not the Suns vs. Pistons, but something else!" Natalie offered her moral support to Bianca, not that I was shocked.

"Yeah, I kinda like the idea of all of us having some kind of intimate arrangement, or at least all of the guys with all of the girls ... though I wouldn't mind a bet with Natalie, too. No matter who wins, we'd all win in the end," Bianca surprised me now.

"Well, it would just be soft swinging of a sort, in any case. No real harm there and I like the idea that nobody is totally left out in the cold," I stated, "But one caveat ... if I win, I reserve the right to lend out your booty to someone else if it suits my mood."

"Deal. Same for you. I like the idea of my girlfriends getting to plow your back field. If they object, I can point out that it's not technically incest," Natalie played with her glasses now, while her other hand slipped down her jeans.

"So, we're going to do this? I mean, we do this, there is no going back. Especially a lifelong deal like this. But as I said, this would require us to be around each other a lot, in order for the winner to claim his or her prize. First bet is already placed, unless anyone objects. If I win, Natalie's sweet ass is mine. If she wins, mine is hers. Either way, we'll have an incestuous affair of some kind and our filial relationship will never quite be the same. Are you really all in? Are you ready to take this step, sis?" I gave Natalie one last out, my gut telling me that I was going to win in spite of my nerves.

"It's a deal, and you guys just witnessed it. Either way, bro, you and I are going to have sooooo much fun! And we absolutely should take our honeymoons together, so that means a double wedding, right?" Natalie licked one finger and let me smell another, which had a very strong pussy scent to it.

"Witnessed and recorded, so no welshing," Aaron chuckled, "Yeah, I know. Not normal boyfriend behavior, but Natalie is a fucking goddess. I absolutely want to see her in action from the outside. It will be like porn, but a lot better, because I'll know that it's real. And I'm telling you, dude, much as I'm not into the idea of taking it in the ass, if you can get past that, being her lover in any sense of the word, her partner ... damn, you're one hell of a lucky bastard."

"Well, I'm not sure that Nathan sees his twin in quite that light. Being a brother and all that, but I tend to agree. Natalie is fucking hot and seeing her in action with anyone ... Then again, I already worship the ground that Nathan walks on, in case he didn't know that. I know that might seem weird, but that's how I honestly feel. Nathan's a fucking satyr, an animal, but he's also ... Well, put it this way. If I wasn't Catholic, he'd be my Messiah," Bianca veered closer to blasphemy by the standards of her faith than expected.

I blushed quite a bit at that, but I wasn't quite sure how my girlfriend would feel about her quasi-Messiah if I lost and had to take my sister's strap-on dildo up my ass. Bianca must have read my facial expressions somehow, because she mouthed, "always." Natalie, to my surprise, looked at me in a way that was so frankly sexual I was a bit stunned to see it on her face. I felt chills up my spine, especially as Bianca gave my sister a very knowing glance and then me the very same lustful gaze. I was somewhat used to it with Bianca ... with Natalie, it was like a sexual earthquake ... I was never quite going to be the same. This had crossed a Rubicon that not even the bet had done ... It was one thing to desire me. It was quite another to view me with such absolute lust.

"Well, that leaves the other two bets, if you're both in earnest," I reminded them, in case they were still interested.

"Yeah, how about this? If, mind you, if, the Cavs beat the Pacers, I own your mouth, but if the Pacers beat the Cavs, you own mine. Think that you can handle that, smartass?" Bianca told Aaron, who smirked at that.

"No way. Indianapolis rules! We'll sweep Cleveland aside! I'll take that deal," Aaron laughingly took her deal.

"I think that Aaron's going to eat his words, and your pussy, pretty soon," I whispered to Bianca, who giggled when she heard that.

"Deal, then?" Natalie interjected, now recording this wager, not the least bit worried about her own fate.

"Deal!" her boyfriend laughed, making Natalie wink at Bianca for some reason.

"Natalie, I think, agrees with you and me. I think that she looks forward to me owning her boyfriend's mouth. I wonder if she knows that she'll be tasting my pussy a lot when he kisses her," Bianca whispered to me, both of us laughing heartily.

"And the final bet?" I recalled, "One between the girls?"

Natalie finished her Long Island tea and looked my girlfriend dead in the eye, "I bet that the Mavericks crush the Rockets. Whatever happens is final. Deal?"

"Stakes?" Bianca licked her lips as she took the offer.

"Let's mix and match. Stakes depending on personal preference. I win, I get to play with your tits whenever I wish. Including the right to suck them like you're my personal milk dispenser. How about it?" Natalie teased her, but she often tended to ogle as well as envy Bianca's breasts.

"And if I win, you have to let me shower with you and shave your legs and twat. It's not quite sex, but it's damn close and the idea of doing that with you makes me wet!" Bianca confessed, a revelation was probably brought on by the Long Island tea, but had all three of us thinking "holy smokes!"

"Well, well, I think that someone has a bit of a lesbian crush on my sister!" I teased Bianca, who looked shyly and sheepishly at me, but nodded a bit ... there was something girlish and adorable about it all, actually.

"So that's a deal, then? Oh, and Bianca, it's a bit more mutual than you think. Though just a crush, of course," Natalie blushed a little now, but stuck her tongue out at my girlfriend.

"It's a deal," Bianca agreed coyly as I held the phone to record the agreement.

"So, that's the parameters of all three bets, and all three are binding, final, and permanent. Agreed? I kind of like that we all have some skin in this game. All three of us can await our destinies with some nerves and anxiety, but also some anticipation. I mean, whatever else happens, we will have a new, intimate relationship with each other that will be hard to forget and impossible to sever. Think of the wonderful consequences there," I confessed for my part, making the others look at me with a mixture of shock and awe.

"Well, the first bet is yours with your twin's. That will be fun for sure, no matter what takes place. Either we'll be treated to your grunts and whimpers as your sister takes your cherry ass and makes you her bitch, or we'll get to witness you plunder her delectable booty and make her your slut for life. I can just see it now, either way, and damn if it don't make me horny as hell!" Aaron declared his true feelings, getting a high five from Bianca for her part.

"Just don't forget, hot stuff, that if you lose, I'll be sitting on your face a lot more than you could ever imagine. It's a very good idea, though I don't remember whose, to move in together, because I fully intend to claim my prize, namely your lips and tongue. Better get some practice on Natalie's snatch, because your mouth will get a lot of use from me," Bianca teased Aaron with a gesture strongly suggesting cunnilingus.

"As much fun as this is, we've gotta get some sleep, you know. Good night, sis, and pussy boy! I have the feeling that I'll get used for my body some time in the night, but to be fair, you can't rape the willing. I'll just have to put up with the objectification, won't I?" I joked around a little.

"Another reason to move out, besides all of us having been out of college for a year now. I don't think that we want Mom and Dad privy to our little ... wagers, do we? We can use the excuse of pooling expenses, which they'll believe, I imagine. As for me, Aaron has a lot of work ahead of him tonight. I intend to give him the practice that Bianca suggested, just in case, plus I really, really want to drain his balls. I do love you, I hope that you know that, teddy bear," Natalie squeezed the somewhat portly and short Aaron Palmer, whom she had once described to me as "pudgy, cute, and adorable ... I just have to squeeze him at times and I could never give him up."

To say that Bianca raped me that night was to understate things considerably, and when I asked her what had her hottest and heaviest, she admitted to me, "It's the thought of you sticking your thick cock up Natalie's ass and absolutely blowing her mind. You are going to make her toes curl and her juices flow. She won't know what will hit her."

"You're assuming that I'll win, then. Thank you for the confidence in me, babe," I told Bianca as she begged me to sodomize her and pretend that she was Natalie.

"Oh, honey, she's whip smart, but she's going to lose and we all know it. She knows it. You know it. Aaron knows it. I know it. Are you fucking kidding me? You're the most analytical, obsessive-compulsive, anal-retentive, methodical person that I know, even more than Natalie, which is saying a lot. She's talking trash there, but she's covering for her own intuition, which is telling her that this is one bet that she can't win. If a guy like you is confident of Phoenix's chances, the Suns will crush Detroit. But, yeah, she knows it. She knows very well that you're going to own her ass very soon," my girlfriend amazed me with her own take on things.

"Think that she figured out when I called her bluff that she had made a mistake, then? Yet she couldn't back down from pride?" I asked Bianca while I continued to bugger her, her hips thrusting back at me with a power that made her own desire apparent to all.

"Oh, it was no mistake, papi. She knew it going in. She planned it this way. She was looking for the surefire loser bet and now she found one. It's perfect from her perspective. There's just no way that she can win and she has never been happier in her life, trust me. Pretty soon, she's going to have to surrender her bottom to you and she's aching almost to get it over and done with ... almost, but first you have to earn it. That's part of the fun. Once you've proven worthy and earned her ass, then she'll delight in giving it up.

"Think that she wants to peg you? Not that much. She'll do it if she wins, because you'll have disappointed her, and yet she'll still love and adore you, but, yeah, she wants to lose. She wants to be your personal butt-slut. I bet that she's practicing the bottom lip bite, too, for when you go balls deep and make her scream your name," Bianca kept up her shocking analysis of the situation now.

"So, this was a sucker bet and she knew that when she made it. Not only knew it, but looked out for it and was glad to find it," I reacted with real surprise now.

"Hell, yeah. Just you watch. You'll win and Natalie will be the happiest girl in the world when you do. Did you see the way that she looked at you, papi? Trust me, while she loves and adores Aaron, she worships you just as much as I do. It's a very different kind of love. It's a love that says, 'Nathan Sikorsky is a motherfucking God and I would fucking sell my soul to be his plaything.' Her love for Aaron is almost maternal. She adores him. She nurtures him. She cuddles him. She strokes his ego. She enjoys the power that she has over him. She protects him. She basically views herself as his babysitter for life and she revels in that role.

"But make no mistake. There is not a relationship of equals. She's the Domme. She wears the pants. She runs the show and rules the roost. And he loves it. He eats it up. It's like he gets to have a Mommy for life to pamper and provide for and protect and guide him. The man-child inside him loves it. He gets to play and kick back and let her take the driver's seat. It's not an accident that he calls himself a sub and a voyeur. It's how he is and she knows it. I can almost promise you that she'll coax him into letting her peg him in time.

"Frankly, from his perspective, it's perfect for him, because to him, she is a goddess. That wasn't a figure of speech for him. He's in awe of Natalie, of your sister, puts her on a pedestal, thinks the world of her, gets his kicks thinking of her in action ... it wouldn't just be voyeuristic entertainment, but a chance to revel in her divinity and his good fortune at being her chosen pet. To him, she is way out of his league, and frankly, I tend to agree. She is a goddess.

"Which is why it's so fitting that her brother is a motherfucking god, and again, she would agree with me there and then some. You might think that she views you as an annoying twin brother or elder brother, albeit by a few minutes, but no ... she considers you the man, the necessary counterweight and foil to Aaron. She needs the boy to submit to her, but she needs the man to make her feel safe in his arms, to protect her, really, and who better than her own brother, the twin who has always treated her so kindly and lovingly at all times? She's not blind to that, believe me. She has to respect and trust a Dom, and with you, she has plenty of that and more.

"Women treat different men differently for a reason. Man children they treat like Aaron, sometimes with love, sometimes with disdain. Men ... grown men, like you? Ones that have proven protective, assertive, that sort of thing? To women like Natalie and me, at least, there is no comparison. I might play along with Aaron's delusions of grandeur, but it's a real hoot. He's a boy. You're a fucking man. I admit that I really want to snuggle him and hold him and such, but I can never respect him the way that I do you, never be in awe and worship of him, never adore him in that same manner.