You Bet Your Ass - Cover

You Bet Your Ass

Copyright© 2021 by Eddie Davidson

Chapter 27

BDSM Sex Story: Chapter 27 - EPIC level story about a house-wife and her daughter who are notorious for making kinky but harmless dare bets around the house. The primary author is Mike McGifford and I have only helped shape it in collaboration. This is the BEST story I've ever been a part of writing.

Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa   Consensual   Slut Wife   Incest   Mother   Daughter   DomSub   MaleDom   Humiliation   Light Bond   Spanking   Anal Sex   Analingus   Enema   Exhibitionism   Masturbation   Sex Toys   Illustrated  

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I was learning not to hesitate – not even to think too much. If I turned off my brain and sucked, fucked or bent over when I was told and just obeyed, I felt much less guilty about what I was doing with and for my family.

I could NOT hesitate, even if it meant sucking a cock that had just been inside my pooper and I certainly didn’t hesitate with that task anymore.

I quickly dropped to the floor and began lavishing Christian’s cock with my tongue. It tasted like pussy and earth. My bottom was not as clean as a whistle, that was certain, but at least there weren’t streaks to lick off him as there had been on previous occasions, so I didn’t gag.

“That’ll do, Drip. I just wanted to be primed, not drained,” he assured me, pulling away from my mouth. “I’ll get enough chances to do that today. Tell you what. I’ll even choose you for the milking competition so you can win at least one, okay? Dad wants you downstairs in five, so finish up whatever you need and put on the outfit dad laid on his bed,” he told me.

With that, he left me kneeling on the bathroom floor and walked off, not even acknowledging my clear, ‘thank you, Sir.’ I was too busy being impressed with Christian’s ability to stop before he came, to be offended that he’d dismissed me the way he did.

As I said, I had no idea what games had been planned for the day, but if the ‘milking’ Chris mentioned was what I thought it was, it seemed that the game would be a contest to see who’s cum went the farthest. No matter who milked Christian, his semen certainly erupted more powerfully than even Danny’s.

To me, it didn’t seem completely fair to judge a slut on how hard they could make semen spurt, but if that were truly the competition, I had no doubt whoever made Christian cum would take the competition. Ken couldn’t ejaculate as hard as Christian despite him being much bigger than Danny and certainly girthier than Chris.

I adjusted my smudged lipstick in the mirror then dropped back to the floor even though I was alone. Kristina had made me crawl so much it had begun to feel more natural to crawl now, and I didn’t even think about it. I just crawled from the bathroom to the bedroom, looked to see what Ken had laid out for me and got a surprise.

On the bed was a crisp, cotton white blouse and skirt from my days in the workforce. I really thought my ‘old’ clothes had all been disposed of. It really felt weird seeing them laying there. Like a reminder of an age gone by. There was even underwear. An actual lacy bra with matching panties and stockings. The only thing not from my days in the workforce was the black patent leather stilettos.

Kristina would hate them as much as I disliked wearing them. They had at least a five inch heel and I felt like I was tottering around on my toes when I wore them. Kendrick had purchased them for me a few years ago, and I’d only worn them a few times for him - never to work.

Sure, they did great things for my calves, but they’d just been completely impractical. Lately, as far as footwear went, they were ‘demure’ compared to some of the things I’d worn on my feet. Any footwear I was allowed at all was the sort of thing a stripper would wear on stage rather than an executive, to a meeting.

I donned the outfit and crawled downstairs, paying particular care to ensure I didn’t ladder my stockings. The first person I saw in the living room was Fart Box, although she looked like Jessica to me. The biggest surprise was that this ‘Jessica’ person was wearing a tee-shirt, jeans and Martins on her feet.

The second shock was that she was sitting on the couch for all the world looking like she’d just warped a month back in time to when she was my daughter, freshly home from a day at the mall. Her hair was even in a ponytail, and she wore practically no makeup. She once again looked sixteen and nothing at all like a slut.

The second person I saw was Elizabeth. SHE looked like a goth-girl who’d come to the wrong house. She was sitting next to Jessica on the couch going over a sheet of paper. Elizabeth had the whitest foundation she could find, black lipstick and black makeup around her eyes. Her clothing consisted of black work boots, laddered stockings held up by suspenders that disappeared under a leather skirt and topped by a corset worn on top of a black tee-shirt.

She had a bunch of stainless steel accessories including a nose ring, lip ring, and at least a dozen earrings. She looked downright scary to me, not at all like a slut who was preparing for a bunch of sex games.

I heard a lot of conversation coming from the direction of the dining room. It seemed clear that Jane was holding court there, with Tiffany, Dianne and Suzanne in attendance along with Kendrick, Danny, Kristina, and Julie. Christian scared me when he came up behind me.

“On the couch, mom,” he ordered. “You’re not an animal. Not yet, anyway,” he laughed.

I hesitated. I’d spent more than a week both naked and not allowed to sit on furniture. It’s amazing how just a week can reinforce such simple things as not being allowed to sit on furniture. Christian hadn’t even commented on my outfit. He’d just assumed it’d be easy for me to revert back to being Carrie, his mother. It was very confusing to me, but I did as I was told.

Just as I got seated, Kendrick came out of the dining room.

“Ah, the players are all here. Great. You look wonderful, Carrie. I haven’t seen you ready for the office in ages!” he grinned.

Had I stepped through a wormhole or something? Kendrick hadn’t called me Carrie in ages. “Thank you ... Master?” I replied, not sure if that was the right thing to say or not.

“Listen to her. Calling me, ‘Master?’ What would her friends at work think of me if they’d heard that!” He laughed at Jane next to him. She giggled merrily. “Just a nice little get together, that’s all this is. It’s so nice to be able to host the neighbors and their friends for a little soiree. And we have lots of fun activities planned, too!”

“Your wife seems confused, Kenny,” Jane giggled after a glance at me. “I’m guessing she really doesn’t know what’s going on after all,” she admitted after a few moments. “That’s hardly fair. I did say I wasn’t going to be a part of anything that wasn’t fully consensual,” she added.

I felt like Jane was somehow sticking up for me, as if reminding Kendrick she had stipulated her own rules for the day and me not knowing what was going on, was coming close to violating one of them. Ken looked at her without a word, but I could see his mind working.

“Carrie already asked to be able to do sex bets, and you said you didn’t want to compete against someone who was just following orders like a robot. That’s why she’s dressed in her old-timey clothes along with Jessica. I wanted this to be a fair competition and I figured them both starting on an equal footing with you and Liz would be the most fair. Just because she chose to exclude herself from the planning doesn’t mean she’s not excited to participate,” he finally said as he turned his focus to me as if daring me to disagree.

That declaration surprised me. I hadn’t intentionally excused myself from helping to plan today’s events! I’d simply done what I was told and tried to stay out of trouble. Sure, I’d complained to myself that Fartbox had been all up in everyone else’s business and had not acted like a proper family slave while I’d tried to show her by example how she should act, but I’d never said I didn’t WANT to be involved in preparing for today.

As far as I was concerned, no one could blame me for not participating in planning when I hadn’t been invited to help. I felt like what Kendrick had said required a response from me. From Carrie. But I felt embarrassed being called Carrie again after all this time, much less being called upon to defend my non-actions.

“I just want to see you all put your money where your mouth is, Jane,” I said sweetly. “I’m happy to be surprised by whatever games you all have organized, and I know that Fart ... Jessica and I can beat you and Elizabeth, winning whatever competitions we get thrown at us,” I replied with confidence.

I meant every word, too. I’d been treated like dirt all week in preparation for these games. Kristina had been so rude, demanding and demeaning all week that I believed there could be no insult I couldn’t ignore or accept with grace.

I’d been called fat, skinny, pale, old, wrinkly, lazy, stupid ugly and had been compared unfavorably to farm animals, furniture, and even food. Danny had slapped, spanked, whipped, punched, pulled, twisted, and in every way he could think of, disciplined me. Chris had indiscriminately used all my holes and had stretched every one of them in some way, although his biggest focus did seem to still be on my butt hole.

Ken had been present for much of that and had even upped the ante a few times in many of his children’s dealings with me. He’d even encouraged Chris to have sex with me while I was already pleasuring my husband, although it seemed he’d kept that sort of thing away from Kristina.

My youngest daughter had made it clear she had no desire to see me used like a sex doll by a man. She hadn’t said so in words, but her belief clearly seemed to be that I was not good enough for her father to fuck, and she seemed to encourage him to get relief from her own sister in preference to me.

If anything, Kristina preferred to see me act like an innocent little puppy or some other baby animal she had to be a surrogate mother to.

While I sat there feeling silly sitting on the couch with Jessica and Elizabeth while everyone else stood around me, Kendrick set the parameters of the games. He made a formal invitation for anyone in the room to participate, although only scores from the four core players would be recorded.

He insisted there were a couple of games planned where only the core players could participate due to the limited number of dicks available, to which Jane assured him she’d solved that problem.

“When you gave me the outline of your ideas, I knew there’d be a need for more cock, so I invited a couple of guys. They’ll be here in a little while, but they have to take their families to church, first. As I promised, I invited James too, but I really don’t think he’ll be too interested in everything you want to do. Still, he promised to be here for that one event with the sheet. Chris is going to message him when the time comes,” Jane assured Ken.

“You gave out our address?” Ken asked skeptically.

“Don’t worry, Kenny. They’re discreet. They have too much to lose themselves, if their wives and families learned what they really like to do for fun! Trust me, Kenny. They’re good people. You might even know one of them. He’s a lawyer. Ronald Richards? No? Well, he’s no good at small talk, and he’s got a little dick, but he’s like the energizer bunny. Real nice guy.”

There was a knock on the front door and I automatically made to stand up but Danny beat me to it.

“Steve! You made it, man. Got some pussy for you today, brother!” I heard Danny say to someone at the door.

“I just wanted to see for myself, brother. If that slut sister of yours is anything to go by, then your mom has got to be a fox!”

I was instantly on edge. Had Danny been spreading stuff around school? Kendrick would have a fit! I was very aware that Ken didn’t want people knowing what went on in this house. His job was almost as important to him as his family.

“Hi Steve,” Kendrick nodded his greeting to Danny’s friend, which allowed me to relax. Danny and Kendrick must have known about the extra attendee.

“Hi Mrs M,” Steve said, coming over to the couch where I sat next to Jessica and Elizabeth. “Hey FB. Haven’t seen you so dressed up in a while,” he grinned. I guessed he had been making a subtle reference to her being covered from neck to toe. It also answered my question about what Danny’s friends and teammates called my daughter.

Steve was the cornerback on Danny’s football team and was slim, tall and very fast. He was also very black. If you heard him, you’d think he was just a somewhat snobby white boy but to look at him, your opinion would be that he was a Nigerian exchange student or something. His voice certainly didn’t match his appearance.

Steve clearly knew what role Jessica had begun to play in Danny’s life and had accepted it without question. This was however the first time since all this started, that he’d been invited to our house. I was immediately glad I was dressed the way I had been the last time we’d actually spoken.

“Call me Carrie, please,” I insisted, smiling up at him.

“Not Drip?” he asked with a grin. He’d clearly been filled in on what was going on around here.

“Not today, Steve,” Kendrick said before I could figure out an answer. Carrie and Jessica are just two horny sluts today out to prove they’re more skilled than the neighbors here. Do you know Liz from school? This is her mom, Jane,” he said, before introducing Julie, Denise, Suzanne and Tiffany too.

Steve seemed to spend an inordinate amount of time checking out Suzanne. He finally spoke to her directly. “Are you going to be involved in these games today too?” he asked her bluntly, making his way closer to her. It seemed Steve had a penchant for older, vore voluptuous women and the brazen confidence of youth. It was like he’d reviewed the menu and decided on his main course already.

Suzanne didn’t seem in any way offended by his critical eye. “If you’ve got a BBC, I am,” she replied.

I immediately thought of the British Broadcasting Company. I had no idea why she cared about that. I was so naive.

“Yeah, Baby! Let’s get this party started!” he laughed, invading her personal space and casually throwing his arm around Suzanne’s shoulder. I immediately thought of salt and pepper then amended that to Jack Sprat and his wife.

Kendrick got back to what he was saying. He explained that any or all of the girls present could play in any of the games. Kristina stopped him by reminding him that she did NOT intend to participate in humiliating herself in front of a ‘bunch of horny boys’.

Kendrick promised her that he understood, but he wanted assurances that she hadn’t changed her mind about the game she had suggested. I had no idea Kristina had suggested a game, much less intended to participate. I bit my lip and said nothing. It was far too late to complain about my youngest daughter suggesting a sex game of any sort. She’d already been exposed to a lot of sex and both Jessica and I playing with our girly bits or each other.

“The sheet please?” Kendrick asked Jessica, holding his hand out for the paper Elizabeth and her had been looking at when I’d come downstairs. I still had no idea what was on it. Elizabeth passed it to him. He scanned it, folded it, and put it in his pocket.

“The first ten minutes is a general warm up. Does anyone have any questions?” He asked the room as a whole.

I certainly did! I had no idea how many games there’d be, what I’d need to do, what the specific stakes were, or even how long the games would go on for. No one else seemed to have a single question. It was like THEY had all been fully briefed. Even Jessica.

“Ummm ... what exactly are we playing for? I mean what’s the consequence here?” I finally asked when it seemed like Ken was about to continue. The funny thing was that really was the ONLY thing I actually did know. I just wanted to hear it from Ken.

“A week in the care of the winner, of course. There can be only one winner and a bunch of losers, so the competition is to discover who’s the best and who’s the worst overall. You’ve all agreed that the only limitation is that no permanent injury or disfigurement can be inflicted on the worst loser during that week. Anyone can play because it just makes things more interesting. Even if all four of you come in last, there’s still a winner and a loser between you. I’m personally looking forward to seeing the pretzel game. Dianne has assured us it’s something else.

“What’s the pretzel game?” I stupidly asked. From what I’d learned of Dianne, it’d probably involve being tied up. That was her special thing.

“I am not going to spend an extra hour going over each game with you, Carrie. You forwent that chance when you refused to help plan this. Just be where you’re supposed to be, when you’re supposed to be there,” he chided me, making me feel even more foolish.

I wanted to argue that, as Jane had pointed out I looked confused because I was. No one had told me a single thing. I didn’t even know why I was all dressed up. I’d finally gotten used to being naked practically all the time, and my bra felt like it was constricting me and the skirt felt like it was smothering my pussy.

“If you don’t have any valid questions, we’ll start. Okay ladies. If you plan on competing in any of the games at all, line up here. Everyone else, to the patio!” Ken said as if he were leading an army.

Ken led the way with Danny, Steve, Christian and Kristina in tow. Tiffany looked at Jane, started towards the kitchen then changed her mind. Kristina stopped too.

“Come on, Julie. What are you waiting for?” she asked.

Julie had hesitated with an expression somewhat like Tiffany’s. “There’s one game I thought I might like to play myself,” she admitted to my youngest daughter.

“Really? You say that now? Jeez, Julie. Not you, too. Which game?” Kristina wanted to know.

“Ah fuck it. We can repeat the game later, I guess,” she said, not answering the question before hurrying over to join Kristina. Tiffany seemed to decide the other way and joined her friends as we also got up and formed a line. So there’d be up to seven of us playing at least some of the games.

“I was thinking you were going to wimp out, Tiffany,” Jane laughed to her friend.

“Shit got real, is all,” Tiffany replied with a shrug.

“I know what you mean,” Suzanne said. “This is going to be crazy good fun though!”

“Okay girls, let’s make a real entrance, here. I want military precision when we march out there. Heads up, backs straight, tits out! All except you, Dianne. I know you don’t have any. Start with your left foot!” she said before counting down while marching in place.

“Bitch,” laughed Dianne.

I felt particularly silly as I copied Jessica in front of me. Jane, who was at the back of the line, continued to give instructions. Jane didn’t give the command to move until we had all begun marching in place and everyone was in step. It sounds easy, but it was a full 30 seconds before everyone was marching in place the same. Elizabeth led the line and didn’t move until her mom signalled her to do so. It was like they’d practiced or something. They all certainly seemed to have been expecting this.

The first step messed half of us up. Jane called a halt and we started again, this time the first step being the same for everyone. I actually felt kind of pleased to be in a little line of girls looking very professional and disciplined as we marched to the back patio, our shoes all clomping on the dry wooden deck slats before stopping, still in line. I stopped marching, but none of the others did. They were waiting for Jane’s command.

Kendrick, Danny, Steve, Julie, Christian and Kristina all clapped for us, like they were clapping for the highschool football team. There were even a few catcalls and comments calling for more ‘bounce’. No one in the marching line reacted to the applause but I could ‘feel’ the smiles. I was smiling too, even though I felt foolish.

That’s also when I knew for sure it’d been a planned thing that I’d been left out of the planning for. I caught myself and did my best to get back into step with the others before Jane called an official halt to the marching bit. I already felt like I’d failed one of the games. Not a great start, I know. I promised myself I’d take more care to follow what everyone else was doing.

Kristina was standing next to the scale out of Kendrick’s bathroom. In an official-sounding voice, she told us all that we had to have our height and weight measured before the first game. Of course, Suzanne grumbled about that, saying she didn’t see where her weight had any bearing on how well she fucked. It sounded like an argument that had already happened and one she’d lost before, too. I think she’d just brought it up because of Steve.

“Come on, big momma, you can win this,” Steve said, making it sound like he was rooting for her to be the heaviest, as if the height and weight thing was a competition too.

I’m not going to go into details about the height and weight results, except to say that Tiffany was closer to Suzanne in weight than I’d expected. Of course, she was almost six feet tall in tennis shoes. The five inch heels I was wearing became part of my five-ten measurement too. Hardly accurate since I’m really five-five. Jane weighed in the most, even more than Suzanne. It had to be weight mostly in her boobs and butt because she’s nothing close to Suzanne in girth. Dianne didn’t even weigh ninety pounds.

I was so full of questions with no way of getting answers. I mean I was right there with more than half a dozen people who knew all the answers to most of my questions, but no one seemed inclined to let me ask them. I’d tried asking Jessica why we needed to get our height and weight measurements, and she just grinned at me.

“You should have gotten involved with the planning, Drip,” she replied with an annoyingly dismissive wave around her as if to say that it was my fault I was ignorant.

“No one told me I could!” I hissed in frustration.

“No one said you couldn’t, either,” she replied dismissively. “I did, and no one complained.”

“Well involve me now and tell me!” I insisted.

“Nope, too late now. You snooze, you lose, slut,” she was maddingly stoic about keeping her mouth shut.

I tried to ask Jane and she was just as bad. Well, maybe not quite as bad. She at least told me that what had started as a bet had morphed into something more personal. That set off red flags in my mind.

“What do you mean by, ‘more personal’? Do you mean getting with Kendrick sort of personal?”

“I mean it’s one thing for you two to have a competition against us two, but this is going to push me as an individual more than I ever thought it would. It was YOUR lovely daughter who suggested this fucking height and weight thing. Do you really think I want a guy who’s going to later have his dick in me for the first time to know how much I weigh and whether or not I have stinky armpits? How about a kid who’s young enough to be James, checking me for grey hairs?”

That threw me. Jane was someone who seemed to have zero modesty. I could imagine her shouting her measurements to some guy perving at her from across the mall square. Yeah, that had happened. But what she was throwing at me as examples, made it sound like we’d all be getting what Kendrick had called an ‘inspection’.

Jane confirmed it and called it, ‘the price of admittance for participation’ but wouldn’t say any more about it. It seemed that I’d missed more of the planning for today than I’d even been aware of. I mean where was I when they’d all sat down together and agreed on any of this?

Probably I’d been tied up in Danny’s bedroom closet or in my ... I mean THE cage blindfolded, gagged, and listening to rock music through headphones in the living room while I ‘practiced’ sexing myself up with a dildo while everyone was supposedly watching TV.

I would never have known if the neighbors had been over for a planning meeting while I was right there and oblivious to their presence. That thought only made me blush even more. Jane, Elizabeth, and possibly even Dianne, Suzanne, Tiffany, and even Julie could have been present while I was alternating a dildo between my mouth, pussy, and ass, laughing at my antics, and I would never have even been aware of them watching me or worse, totally ignoring me.

At the time, I was glad I was blind and deaf to any audience, but now, I felt even more embarrassed by the thought of them seeing me like that. Now I felt even worse because I COULD have been in on the planning too, if I’d thought to be more assertive and had insisted, like Fartbox had, to be involved with the planning.

Thoughts like that took the wind out of my inquisitive sails. Fartbox was right. I’d had my chance to know. Now all I had left was to do as I was told. I’d at least learned I was somewhat good at that. It was certainly easier than knowing what was coming, so I quit asking questions and waited while Danny called out weights, Chris called out heights, and Kristina recorded the results.

It was still raining. Did I mention that? I don’t think I did. That didn’t seem to bother my family or any of the others, right up to the point when Kendrick told us - the players, that is, to start running laps in our backyard.

Fartbox and to a degree, everyone else, had known this was coming and had dressed accordingly. I was the only one in dress shoes without the benefit of a solid heel. Only once you’ve tried to run in heels on grass could you possibly understand how difficult it is. Also, only then did it occur to me that no one else even had flip flops on despite that being a common form of footwear locally.

They all wore some sort of closed-toe shoe that would be fine for running in. Then me, with completely inappropriate footwear for jogging around the yard. In the rain. Getting completely soaked with very cold rain. My blouse became translucent when wet and the lacy bra underneath was as much on display as if I was wearing it without the blouse.

Don’t get me wrong. I was glad for having it, as even my little boobs would have been sore after five laps of the yard, and I can only imagine how Jane or Elizabeth would have felt, but sometimes being fully dressed can make a person feel more exposed than simply being completely naked from the get-go.

My skirt was dry clean only and would probably be ruined, I thought to myself as I struggled around the yard, barely managing to keep up with butterball Suzanne who had all sorts of verbal support going on from Steve. Support she was loving, judging by the look of determination on her face.

Kendrick and Christian were there for me too, with their own verbal support. I heard them encouraging me and driving me to keep going when they thought I was slacking off while Danny focused on Fartbox although his encouragement included promises of whippings and clamps and other painful consequences for letting him down.

Kristina encouraged Dianne while Julie even had some nice words for Tiffany, although Tiffany must have been a regular jogger and she completed the five laps hardly even winded while lapping me. In my defense, there was one place where my heels completely sunk into the soft, wet ground, and I very nearly had to ditch the heels and run in my stockinged feet.

While maybe I’m making it sound like it was a form of torture, the warm up was actually executed with a lot of laughter and giggling from the ‘contestants’, especially Elizabeth and Jane. Elizabeth jogged with her mom and encouraged her to shake her tits and ass more as she ran past the spectators on the covered patio.

I didn’t really understand why we were all dressed, considering this was to be some sort of amateur sex-Olympics. I would have thought Danny with his love of boobs or Christian with his affinity for butts, would have insisted we run nude. I later found out Kristina had insisted on us starting out dressed. There were a LOT of people to have preferences catered to, and Kristina’s was to embarrass others.

I finished the ‘warm up’ much worse for wear. Not only was my blouse drenched and stuck to me like a second skin, there were a couple of specks of mud on it from other contestants kicking it up with their shoes. My carefully styled hair was a mess and only because my makeup was waterproof was it still in place. Elizabeth’s heavy goth face paint had been destroyed in the short time she’d been jogging.

Ken tried to stop us all from returning to the covered patio after our warm-up but Tiffany ignored him. She wasn’t part of the core group of four, so she didn’t have to listen to him. Suzanne looked at Steve, and he made a gesture that caused her to wait in the rain too. Dianne didn’t seem to WANT to go back onto the porch. She was enjoying being soaked.

The first game is where the height and weight requirement became clear to me but at the same time, confused me even more. I wasn’t paired with Fartbox. Instead, I was paired with, of all people, Elizabeth.

The game was based on the original wheelbarrow game, where one player would act as the wheelbarrow while the other would hold that person’s ankles. Instead of having a wheel, the person whose ankles were being held, would use their hands to ‘walk’ across the yard. Kendrick ordered all contestants to remove their footwear. My shoes were already ruined, so I expected to be throwing them away. No huge loss. They were not comfy shoes anyway.

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