You Betcha! Ch. 03-05

"That's exactly how Simon is to me, too. You're in love with him. I'll tell you all a secret. I'm in love with Simon, too. Sorry that I played it cool, but that was necessary, so I didn't make a mistake and marry the guy. Oh, he's a perfect hubby for a good Italian Catholic girl who knows that she's got him locked in because she'll never divorce him and he has no reason to leave her, ever.

"But he's not the right ... husband for girls like you or me, Becca. Our spouses need to be under our thumbs, as Eddie will be for you, trust me. So, the most he can be is a boyfriend. The most. And I'd rather not take that plunge until it's clear where we stand. Besides, I've already got my eye on a very different spouse ... and the good news is, they're Jewish just like me.

"The bad news, at least for my parents, already worried about grandchildren and such ... she's a girl. She's Paige. Yeah, in case you missed it, I'm bi, girls! And I really want Paige as my bride," Heather admitted to us all, much to my shock and everyone else's.

"Do you really think that you can ... control a ginger like Paige, though? Under your thumb doesn't seem likely if you marry her. Not to discourage it, but I know Paige. She doesn't strike me as the subbie wife type. She's a feisty redhead, after all," Becca observed now.

"I wondered the same damn thing. I mean, we all know Paige. Which is why I wonder about it," Janine added with some confusion.

"Shows how much you know, guys! I love Heather and I would love to be her bride! Incidentally, that time that we compared notes about Simon? We did it ... in bed. After I ate her out and she ate me!" Paige exclaimed, further complicating things, but in a delicious new way.

"And the circle closes," Janine smirked.

"Or the noose tightens," Melanie laughed now.

"Worlds are colliding! If Relationship Simon walks through that door, he will KILL independent Simon! A Simon divided against himself cannot stand!" I teasingly paraphrased George Costanza.

"What about Janine? If I get at least ... three lovers, counting Melanie, Becca, and Heather, whereas Becca would get Eddie, for argument's sake, and Heather gets Paige ... who does Janine get? Just asking hypothetically. I don't think that Becca's ready to take such a dramatic step yet," I asked out of sheer curiosity.

"Not yet, you're right. But she wants to get there, and that makes a huge difference. She just can't bring herself to admit what she really desires, what she truly wants at all. As for Janine, just ask her yourself," Melanie stopped sucking me long enough to answer that query.

"And the easy answer to that is ... I don't know, but I would love to find out. Incidentally, Heather, I think that since you're here, you should consider yourself on lockdown with us. You're now part of the quarantine squad, babe!" Janine's tongue danced with Heather's ... and then Becca's ... and then Paige's, and then mine.

"I think that was the whole point, baby! Oh and ... little confession. It wasn't your house key that I copied, but Becca's. With her consent. We've all been plotting to spend lockdown with you. It's just none of them knew about my involvement ... except Becca. I was the secret weapon, you see," Heather confessed to the rest of us now.

"To what end, though?" I questioned them.

"Oh, that's for us to know ... and you to find out," Becca got the last word for now, using a dirty trick like restarting the episode while Melanie hungrily swallowed my load.

Oh, dear me, what kind of bizarro world am I in now?

Chapter 5

"You know, for a 'good Italian Catholic girl,' Melanie, you're rather open-minded. I don't object to that, far from it. I certainly approve. It's just a cognitive dissonance that I can't overlook. Though, of course, you don't always have to be a 'good' Catholic girl. You could be a bad one now and then," I teased Melanie a little, causing her to snicker before feeding me my snowball.

"See now, I can be a 'bad Catholic girl' from time to time, can't I? And the inner bad girl wants so badly for her fiance to fuck around on her. She even wants to make it happen, while the inner good girl will obey her husband and never even think of divorce or anything of the sort. I told you that you have a hall pass with each of these girls, you know. I mean it, trust me. Of course, even if you had no hall pass with a girl, what am I gonna do about it? I already told you that I'll never leave you. I have no leverage here ... and that's exactly how I like it!" Melanie confessed to me.

"And if I told you to do a girl, which part of you would want to do it? The good Catholic girl or the bad one?" I asked out of curiosity now.

"Both, if I'm being honest. The good girl wants to obey her hubby, while the bad girl wants to experience Sapphic pleasures at last," Melanie admitted to me now.

"So, you're at least bi-curious, if not bi outright?" I inquired of my fiancee.

"Oh, I'm definitely bi. It's all that I can do not to grab Heather and kiss her on the lips," Melanie told me as the episode ran its credits.

"Okay, then. I dare you to do it. Make out with Heather. That's a dare from me, your own fiance," I told Melanie, while Becca, Janine, and Paige listened in fascination.

"Come here, you!" Heather told Melanie as their tongues danced together at last, making it a very sensual Sapphic kiss.

"Wow, that's incredibly hot ... but if we're doing dares, what about bets? I bet you guys that Melanie won't suck Simon's cock out of someone's ass. Now, who wants to volunteer their ass?" Becca interjected now.

"Stakes?" I asked, "and who is taking your bet?"

"Okay, I bet Heather that Melanie won't suck your cock out of someone's ass. Better? Stakes are that I get to suck her tits if I win. I've wanted to suck her tits for a while now. They're such wonderful tits! I know that Melanie loves Simon and would do anything for him, but there must be limits to her devotion, right? After all, they don't know each other that well. It's almost love at first sight, okay, it basically is, but she doesn't trust him that much, does she?" Becca asserted, making what I was sure was a sucker bet for Heather.

"Whose ass and what if you lose?" Heather demanded now, seemingly eager to get on with it now that Melane and she came up for air.

"If I lose, I have to eat your pussy instead. And as for whose ass, that narrows it down to Paige and Janine," Becca asserted.

"What happened to not cheating on Eddie?" Paige laughed.

"Good question and I wish to make an amendment. If you lose, Becca, you have to eat Paige's pussy, not mine. Still up for it?" Heather smirked.

"Sure, but that leaves Janine as the anal fuckee. If she's up for it, that is. If she dares," Becca insisted, "as for not cheating on Eddie, you know the guy would never object to me eating pussy or sucking tits, so it's not cheating in this case. It's only cheating if it's something that your partner would protest or dislike. Eddie would so watch me suck tits or eat pussy, I can promise you that much."

"I see your point in Eddie's case. He'd think that he'd died and gone to voyeur Heaven," I laughed now.

"Well, Janine? What's it to be?" Becca asked her.

"Don't you think that it's taking a huge risk basing this on predictions of Melanie's behavior? I think that your tongue is about to get very up close and personal with my ginger bush, girl," Paige taunted my sister a bit now.

"So that we're all on the same page here, if Melanie sucks Simon's cock straight from my ass for at least a minute, it counts. If she backs off at less than a minute, Becca wins and sucks on Heather's tits for ... how long?" Janine stipulated.

"Since Heather's not lactating, let's make it half an hour, unless she's comfortable with longer," I proposed now.

"Works for me. I'll stick to the half hour ... this time. If she does well enough, I may seek an encore. I have to warn you ... my tits are a big zone for me. When people suck on my tits, it really turns me on. Just ask Paige. Simon, you should try it someday. I think that you'd love it!" Heather winked at me now.

"You mean that you could come just from having people suck your tits?" I asked my loving neighbor.

"Hell, yeah, and I have! Again, just ask Paige!" Heather licked her lips now.

"So, are we doing this bareback, then?" I wondered aloud now.

"Sure, that's why it's a bet. It's also a test of how far I'd go, right?" Melanie licked her lips and I got a strong instinct about the outcome now ... but was my gut to be trusted here?

I shivered a bit as I considered the ramifications. It might not be cheating given Eddie's likely tolerance and a possible lockdown hall pass, but Becca certainly pushed the envelope a bit with everyone here. She showed that she wanted to watch me sodomize someone and see if my own fiancee would do ass-to-mouth for me afterward. That was some pretty intense escalation of events now.

"Plenty of lube, please. I'm about to get my virgin ass wrecked by that thick prick of Simon's. I'm gonna need it, trust me!" Janine declared as she led us to Becca's bedroom and bent over.

"Spread 'em, Janine. Let's get you all lubed-up for my brother's cock!" Becca surprised me now by even kissing and briefly licking Janine's backdoor, "I had to get it a little wetter, you know. Eddie won't mind this, I think."

Then my sister started slipping fingers inside Jane's asshole, applying the lube that Melanie eagerly brought us for this act of buggery. To our complete amazement, Becca really got into it for a minute, seemingly forgetting that her role was to prepare Janine's tush for my prick. She must have enjoyed the taste of Janine's bottom, which would make her more like me than she could ever really know. It was all that I could do not to rim and spank Janine before or after butt-fucking her, her ass looked that damn yummy!

Finally, though, Janine's butthole was ready and I eased my first inch or two inside her. I gave her a moment to catch her breath, but then she bucked her hips on her own and I slid more of my dick into her derriere. I stopped again and she audibly moaned in response before bucking her hips yet again.

"Thanks for giving me a moment to cope, but you can stop the slow-poking. I'm horny as fuck now! Ram me deep! It will hurt, but I like it rough!" Janine pleaded with me.

I picked up the pace and sure enough, Janine moaned again ... and again ... and again. She moved that butt and her hips back at me repeatedly, trying to draw me deeper into her cornhole. On an instinct, I started slapping those olive-skinned buttocks of hers and she moaned even louder. There was a very strong feeling that she wouldn't want to give this up. I had created an anal monster and she'd crave sodomy for the rest of her life now that she gave up virgin ass to me.

"You know that this is ... yours now, right? Forever yours! This ass belongs to you! No matter who I date or marry or whatever, you ... can ... have ... this ... on ... tap!" Janine announced now in front of everyone present.

"Repeat that, please, for posterity, Janine! I want to hear this for the record and I want future generations to know that MY BROTHER owns your sweet Iraqi ass! Are we clear?" Becca asked Janine as she hit record.

"SIMON HAVEN OWNS MY ASS!" Janine screamed in a way that there would be no mistaking her words on audio.

"Attagirl! I'm extremely pleased at this, since it means that I can asked to borrow it from Simon, not from you, and you'll have to give it up to me ... if he tells you. Hell, if I have to, I can borrow your sweet ass for Eddie's use as a peace offering after all of the cheating that I've done today," Becca licked her lips while Janine bit her bottom lip from my strokes inside her butt.

"You've surrendered the booty to me, to me, a guy with such a fat cock that you might well leak blood from your asshole when I've finished, even with lube? Hot damn, that's sexy as fuck! You really must dig pain!" I admired and fondled Janine's buns while I plowed her backfield now.

"Yes ... yes ... fuck it harder ... deeper ... fuck ... my ... ass! FUCK MY ASS!" Janine begged for rougher sodomy now, stunning even me.

"Yeah, I'll lend Eddie Janine's ass when he comes back if it helps. It's the least that I can do for him, you know," I grinned as I felt Janine's well-oiled asshole clench and rub my prick in all the right ways, too.

"Oh, fuck ... yes ... yes ... yes! Deeper, please ... harder ... rougher! Stretch my ass! Take it! Ravish it! Ravage it! Use it! Ram it ... deep!" Janine couldn't take anymore and she creamed herself on me.

She also squeezed my dick so hard with her butt muscles that she practically pulled all of my cum out of my balls. She extracted every drop inside her bottom, making me flood her bowels with my sticky spunk. Then she relaxed her pucker and I slid out of her with a loud pop. I looked down and was pleased to see that it was clean. She must have cleaned out, but why? Did she plan all along to give me her anal cherry or was that meant for someone else to take? Was this something that she did often, just in case?

I knelt behind Janine's ass and spread her cheeks to lap up some of my own cum from her tasty tush, which just made her squirm and cum all over again. She squirted me right in the face in response to my tongue exploring her delicious booty that way. Well, it was MY ass now, so I might as well devour it, right? My own creampie didn't taste bad at all, at least not to me, but she was clearly a squeaky clean girl, even regularly cleaning her butt as she should. I now realized that Janine really took pride in her bottom and would always take care of it as a sign that she respected herself. Good for her!

"Hey, bro, don't forget that you can lick my ass, too, whenever you wish ... you can spank it, too! Just don't think that you can fuck it, not unless or until I say so. That's what Janine's asshole and Melanie's mouth are for, apparently," Becca reminded me, even as Melanie knelt and took every inch of my cock between her lips now.

Melanie had this determined look on her face and the message in her eyes was very plain. Becca had lost her bet and would soon have to spread Paige's thighs for her late-night snack rather than sucking on Heather's tits. Paige winked at Becca and me, parting her legs in eager anticipation of my sister muff-diving her. I had the distinct feeling that Becca would soon get hooked on eating Paige out, too.

"I think that it's clear that Heather wins this bet, isn't it?" Janine smiled as she watched Melanie suck my cock eagerly straight from her own ass.

"Yeah, Becca ... crawl between Paige's legs ... and pay up!" Heather taunted my sister, who simply winked at me and knelt to honor her bet.

"Oh ... God ... oh, God! That mouth ... Heather, her mouth is like a sponge ... it feels sooo ... good! That tongue ... those lips ... wow!" Paige blushed and cried out in pleasure as my sister ate her out with gusto.

Becca devoured Paige with every bit as much excitement as Melanie put into sucking my dick, both ladies proving that they were naturals at giving oral service to people. Heather and Janine watched with real fascination at the way that each girl performed such eager favors for us. The two of them started making out, too, their tongues dancing with each other during the very slow and sensual kisses. If anyone was squicked that Melanie so gladly and hungrily sucked me right out of Janine's bottom, you could have fooled me.

"I think that she likes how your ass tastes, Janine," Heather teased Janine and Melanie both with that quip.

"Yes, and if I had my way, Janine would live with Simon and me, just so that I could regularly suck his cock straight from her ass!" Melanie spoke up now, even as Paige screamed Becca's name loud enough for the neighbors to hear.

"I think that I'm gonna have to get a hall pass for Paige's juicy twat, if nothing else! Though I'll win your tits in time, trust me!" Becca warned Heather.

"Is that a threat ... or a promise?" Heather retorted, teasing my sister with her ample bosom.

"Less talking, more lapping!" Paige squeezed her thighs to put Becca back to the task at hand: giving her oral pleasure.

"If I date or marry someone, I will so grandfather in Simon's rights to my ass, you know," Janine declared for all to hear.

"Maybe you can put those in your wedding vows," I chuckled, even as Melanie swiped her tongue across the head of my dick again.

"I only wish that we could with ours ... well, we could, but with a secret second wedding or something ... or maybe even a secret first one. Secret ceremony, secret vows, which nullify parts of the wedding mass, but only some parts. Parts like forsaking all others," Melanie thought, "but I don't know how the Church would take that part."

Then Melanie got back to work sucking my cock, of course, even as I said, "not a second or secret wedding. A collaring. The collaring would make it clear that Janine's ass is mine, though it could imply that the rest of us is, too."

"I'd be cool with that. I'd wear your collar proudly, Simon. Think of it as a game of 'Simon says' that never ends and never has to use those words, because you are Simon. I get to play 'Simon says' for life!" Janine assured me just as I came down Melanie's throat and she eagerly swallowed my spunk.

"You'd be not just my anal slave, but my complete and abject thrall for life?" I asked in shock.

"Yes, because even the thought of it turns me on. I'm not doing this because you want it. I'm doing this because I NEED it. I need to be ... yours, I think. You won me fair and square. You own me. For life. Deal with it. I'll sign a contract with you, though I want Melanie to countersign it, if possible, as proof that I have her blessing to serve you for life," Janine announced, making Melanie lick her lips before both of them kissed me with tongue.

"This will make for one helluva marriage!" Melanie told us, "but hell, yeah, I'll sign the damn thing! The way I see it, we're one flesh now. What's yours is mine and what's mine is yours. That means that Janine is ours now, though mostly yours. She's our slave and I'll treat her very well, as I know you will."

That was when Paige squirted all over Becca's face and pulled her up to kiss her softly on the mouth.

"So ... Heather is Simon's friend with benefits or fuckbuddy or bedfellow or whatever. Becca's ass is his for licking and spanking purposes, but not fucking. Melanie is his fiancee. Janine is his rather eager sex slave for life. I feel left out of the Simon fun. What do I get to be for him?" Paige waxed a bit jealous now, her face flush with primal lusts now.

"Girlfriend. You're his girlfriend now. Deal? You can't be his fiancee, because Melanie has that covered. You can't be his fuckbuddy, because I have that covered. You can't be his sister with benefits. Becca has that covered. And you can't be his slave. Janine has that covered. The only vacancy left is that of girlfriend, so that's what you are. You can't be MY girlfriend, after all, since you're already my fiancee, right?" Heather concluded.

"Interesting logic there. Very good lawyering, sophistry even," I teased Heather, "this means that all of you have some kind of intimate bond with me. In a sense, you're all my girls. Now, I have one question for you ... was all of this random or any of it? Did you gals all set out to share me in some capacity, but first you had to tease me to get me all hot and bothered for you?"

"Maybe ... maybe not?" Heather winked at me and blew me a kiss while Melanie and Janine both planted lip locks on me.

That was, inevitably, of course, when Eddie chose to FaceTime Becca's phone...

"Holy fuck, it's Eddie ... what now?" I heard Becca exclaim as she answered her boyfriend's call ... visibly half-naked.