Chapter 1

“There is no fucking way that Bernie Sanders is going to win the Michigan Primary, bro! Not gonna happen!” my sister, Natalie, asserted with no small measure of confidence, being the Hillary fanatic that she was.

“I think that you’re overestimating her crowd size, counting on outmoded data and demographics, ignoring the real anger over Flint water and the loss of jobs, the TPP, and the general sense that Clinton has sold out to the Goldman Sachs crowd. Bernie’s tapping into that with a fury. He’s gonna be the revenge of the millennials and the blue collar, hard hat Democrats, those who haven’t been seduced by Trump, that is. This is an anti-Establishment year, plain and simple,” I smirked, having known friends in Detroit and gotten a real sense that this was not a normal election cycle at all ... Donald Trump’s ascendancy over even Teabaggers like Ted Cruz was proof of that.

“He’s just a washed-up old socialist, bro! Besides, we’re both Jewish, we know what anti-Semites people can be, even now. There’s no way that one of us can ever win over enough goyim to get elected President. It’s a sad truth, but the White House is unofficially a Christian-only place,” my sister pointed out a very real and painful fact about how tough it was for Jewish candidates for higher office even in 2016.

“This year ain’t normal, sis. Trust me on that. I can feel it in my bones,” I retorted, thinking that would be the end of it or expecting either her boyfriend or my girlfriend to speak up by now ... then again, her boyfriend was a Republican and my girlfriend was at best a semi-political independent flirting with Gary Johnson.

“Okay, if you’re so fucking sure that Bernie 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 Hillary wins, and thus I win, I get to peg my sweet brother as often as I wish. If Bernie 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 Democratic Primary, 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, Kasich wins Ohio, I own your mouth, but if Trump wins Ohio, you own mine. Think that you can handle that, smartass?” Bianca told Aaron, who smirked at that.

“No way. Trump is sweeping the primaries. He’s gonna nail Ohio! 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 Trump wins the nomination outright, instead of a brokered convention. That bet will take longer to discover, but 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 cuddle and take turns spooning with you, my twat against your ass and vice versa. I want to snuggle naked under the covers with you, babe. 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 won’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.