You Bet Your Ass
Copyright© 2021 by Eddie Davidson
Chapter 21
BDSM Sex Story: Chapter 21 - 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
My eldest daughter probably sensed reluctance from me to do anything more sexual than kissing her. I would have been reluctant to do that with anyone; I guessed she was referring to her licking my private parts. I wasn’t allowed to call them that anymore though – I had to say cunt and asshole, and I think saying it out loud made it seem even more vulgar to have to lick those parts on another girl.
Maybe Jessica was worried I’d stop kissing her now? She knew that was not our call to make.
To me, though, there could be nothing more sexual than kissing. It was like the ultimate expression of lust and desire. I was eager to suck dick and fuck strange guys. Yet I drew a mental line at the thought of kissing them.
Despite that emotional hurdle, here I was kissing Fartbox and enjoying it. I’d never considered myself bi-curious before. It would have been easier for me to agree to licking pussy than it would, to be told to French kiss a female. I was glad I hadn’t been offered the choice of doing it or not doing it. I know I would have chosen not to. Did any of my family want to see me go down on a girl, though?
We got back to swapping spunk with me experimenting with the idea of dripping my cum-laden spit into my daughter’s mouth from a few inches above her.
“Ew, look at them, dad. They’re totally lezzing out and loving it,” Kristina observed, instantly bringing my attention back to my surroundings. Kristina sounded angry that we were doing what we’d been told to do and especially upset that we were acting like ‘lesbians’ even though we’d specifically been told to do that. Her disdain surprised me based on what I’d seen of her and Julie together. It seemed to me that if anyone had lesbian tendencies, it was my youngest daughter.
“Yeah, maybe I should have Phil make two sets instead of just the one?” Danny asked. I’d tuned out their conversation, so I had no idea what Danny had been telling the others or what he meant by a set. A set of what? I wondered to myself.
“How much does he want for them?” Kendrick asked.
“He did a search online at school and said a regular pillory stand costs about a grand, but he promised he could make the sort of one I want for fifty bucks and a chance to be the first to use it,” Danny assured his father.
A pillory? I could no longer ignore the conversation going on around me. “You’re getting a pillory, Sir Danny?” I asked. I know, stupid question. But I couldn’t help myself!
“Yeah, but I was only thinking about Fartbox at the time. I totally forgot about you, Drip,” Danny waved off my question. I was stunned into silence. Both by his casual reference to an item that would immobilize my hands and neck, but by the way Danny had ‘forgotten’ about me. How could someone ‘forget’ about their own mother?
“Where would this pillory go?” I asked, emboldened by the fact that no one was telling me to shut up.
“Jeez Drip, don’t you ever listen?” Chris teased me. “He was saying it’s just a compact one to restrain your neck, wrists and ankles. That way anyone can fuck any of your holes and you’ll have no idea who’s in your cunt or ass. Kristina wants to blindfold you both so you can’t see who’s fucking your mouth, but I think you should be able to see who it is,” he assured me like he was doing me a favor or standing up for my ‘right’ to see who’s cock is in my mouth at any given time.
“Or cunt. Don’t forget what Kristina said about you two dining at the Y”, Danny added.
I wondered just how out of hand this was getting. Kendrick wasn’t putting a stop to any of this discussion, so I wondered if he was simply letting the children throw out as many suggestions as they could before reining them back in.
The agreement had been that I’d do a few embarrassing things in exchange for Kendrick allowing me to play sex games. That had morphed into me and my daughter both being allowed to. For a price. Now here I was, just having shared cum with my daughter while wearing chains that denied me the ability to stand up fully. Jessica had just endured what amounted to a day-long, rough, bruise and welt-inflicting gangbang in previously virgin orifices. Around me, my children were discussing the purchase of at least one pillory to secure us in.
My son Danny sounded like he had enjoyed hurting my daughter Jessica too much today. As if he’d really gotten off on personally causing pain and watching her be slapped, punched, and beaten by a group of equally sadistic boys before her mouth, pussy, and bottom were stretched in every way imaginable. I hadn’t planned on pain being part of my everyday life while I indulged in sex bets. I certainly didn’t want my daughter put at needless risk!
I knew I would have to have a serious one-on-one with Danny just like I’d had with Chris and Kristina, but this one wouldn’t be to ensure he was okay with the journey I’d embarked on. This conversation would be to find out if Danny had come to hate us both for what we were doing. It was clear that he LOVED what we had chosen to do, but it also sounded like he HATED us personally.
I understood and accepted that from Kristina as her mechanism for coping with the stress in her life. But for Danny, he didn’t face the same stressors as a female in junior society where cattiness, backstabbing, and cliques were part of everyday life. Danny already had football with its associated benefits. He was looked up to by the whole school and had a chance at every game to relieve stress in a fundamental way. So what other than him hating us, could inspire him to treat Jessica so badly today?
I came to learn from Jessica that she ASKED him to go harder on her and what I considered to be “treating her badly” was a roller coaster ride of humiliation, sexual objectification and pleasure to my daughter. I was still wrestling with that idea it was for me as well.
As an example, earlier that day I was on the couch in the living room masturbating with a dildo. I had been there “training” my holes. My son walked into the living room and I didn’t stop- couldn’t stop. I wasn’t supposed to stop unless I was instructed to do so – Kendrick had made that painfully clear when he gave me the instruction to do all of this out in the open. It made me feel filthy and powerless and I hated to admit that I loved that feeling – and dreaded it at all at the same time.
“What’s your most important hole, Drip?” Christian asked me, thoroughly surprising me.
I knew he wasn’t talking about needs. If I didn’t have a mouth I couldn’t breath, but if I didn’t have a cunt, he wouldn’t exist. I was a little surprised myself when the answer came unbidden. I hadn’t even thought about it or the person I was specifically saying it to.
I didn’t answer. I had a habit of clamming up when someone asked me a question – it didn’t matter if it was sexual or just about how my day was going. That nasty habit was not going to fly around my family. He struck me across the tits with a back scratcher we had laying around in the living room.
I answered abruptly and honestly. “My asshole, sir.”
“Really? Why?”
Now I really did have to think. Why had I said that? Was it a subconscious desire to tell Christian what I thought he wanted to hear? I decided that didn’t feel completely right. I knew he’d be happy for me to say that but I’d begun to believe it on my own.
“I think it’s because it’s the hole that does the most giving, Sir. If your were to rub my cunt, I’d cum. When I suck cock, I get instant gratification from the look on the face of whoever I’m sucking. I can only get that same gratification by feeling a cock squirt it’s load inside me, but I have to work more to achieve it. I can’t explain it, sorry Sir.”
“So you like to give more than receive?”
“I suppose you could say that, but really, am I? I have a lot to be thankful, having a family as understanding as this one.”
“I like thinking you’re happiest when giving, mom. It just so ... you.”
I didn’t even mind Christian calling me mom when he said it like that. I was almost overcome with emotion. I know a tear of happiness rolled down my cheek. But I wanted to test myself, so I asked Chris if he’d help me with something.
“May I use my asshole on your cock, sir? I’d kind of like to see if I can get you off without cumming myself at all. Fartbox and the neighbors all want to come as much as possible, so that’s not really challenging to them. They should try NOT cumming if they really want a challenge.”
I really meant it, too. I was horny twenty-four seven these days and it was a bigger challenge to stop myself cumming than to just throw myself into an orgasm.
I couldn’t do that with my cunt. It’d be too difficult, just as it’d be too easy to suck or jerk off a cock without cumming. My favorite hole was the one that provided the perfect challenge, so to me, it as just another reason for it being the most important. I wasn’t sure if I was ready to admit that to my son though. I wondered if he saw me as a whore or as a mom or both!
“Have you pooped recently?” he asked as he scrunched his nose. I told him that I had and asked why. “I don’t like brown specks on my dick,” he said.
After that I began regularly using a fleet enema bottle without being told to keep my backdoor empty so that I could take a dick in my ass anytime someone wanted me to perform for them.
My son humped me in the living room that afternoon – and I sucked his cock clean of the “Brown-eye” stain when he was finished shooting his hot warm load up my ass.
“Will you ask me questions like that in the future?” I kissed him on the lips. I kissed my daughters on the lips pretty regularly before the training – it was never sexual until Jessica. I was the first to open my mouth with Chris.
“Questions like what?”
“Anything, any thing you want to know or would like an answer to, Sir. As long as you don’t let me clam up I’ll respond as honestly and completely as I can,” I reminded him that was one of his father’s new rules for me.
“Do you like kissing me?”
I instantly regretted telling him to ask questions.
“Yes Sir, I do. You kiss very well,” I leaned into him and started smooching and sucking on his tongue – it was incredibly sexual and totally inappropriate – and it made me horny as hell.
I wondered if Chris had ever kissed a girl before – perhaps a boy at school? I was still doing this all under the auspice of preventing him from becoming gay. I was also really enjoying it. “You are a good kisser as well, Sir.”
Danny walked in on us and caught us in the middle of making out on the couch. “Oh, will you two get a motel room or something?” he joked – and slapped his little brother on the back playfully.
“Mom wants us to ask her questions from now on,” Chris stopped kissing me abruptly as if he had suddenly grown bored – it hurt my feelings. I wanted to keep making out. I felt like I was a high school girl making out under the bleachers again.
“Why? She never answers them anyway.”
“She wants us to make her answer,” Chris clarified for me.
“Why?” Danny asked me. It was my chance to be truthful with him.
“I’ve always avoided questions because I am shy, and I know it is annoying. I’d like you to break me of that habit, Sir. Make me answer your question and be as honest and open as I can be – if I am not.”
Danny practiced asking questions and correcting me with the attitude-adjuster by whipping my tits and ass anytime he asked an embarrassing question, and I was reluctant to answer. He said I had to answer fully and not just “respond”. I had no idea how annoying it really must have been that I rarely ever completely answered questions when asked. It was definitely a pattern with me though and I knew it was a bad habit.
Chris noticed that my asshole puckered when I was asked something embarrassing.
“Do you like pain?” Danny asked while I stood in front of him and let him smack me if my answers were not up to snuff.
“No sir,” I said truthfully. I assumed no one “liked” pain but according to Danny – Jessica did. That made sense based on what I had seen of her behavior lately. I gave the wrong answer from his perspective. I was allowed to say that I didn’t like pain but I had to elaborate on my reasons. I received two hard swats across my nipples that left them red and puffy.
“I do not like pain, that is why it is effective to motivate me to behave myself. If I correct my behavior, then I won’t get whipped again.”
“You’ll fuck up something else, Drip.” Danny laughed. He was right and I agreed with him.
“Are you going to get revenge on Chris and I for beating you when this is all over?” Danny asked.
It was a surreal question. It was the first time I really processed there was a time this would be all over. Kendrick had made it a distinct possibility it would last three weeks but he hadn’t been entirely clear whether I go back to normal – or if that was even possible. I desperately wanted to avoid the question because I wasn’t sure yet if I desired to go back to normal.
“I appreciate these little attitude adjustments, Sir. The fact that you and Chris are taking the time to straighten out a bad habit I’ve had since I was a little girl is flattering,” I admitted honestly.
“Chris is just admiring your butthole, I am the one doing the questions now,” Danny corrected. It was true – Chris was pulling my ass cheeks apart and letting them clap back together and playing with me while his brother questioned me.
Kristen joined them shortly after and adding another twist to the “question game” as we called it. They asked me any question – things they’ve always wanted to know about my past or what motivated me. Kristina connected the dots that the more humiliating the pose I was in the more honest I would become.
She told me to lay on the carpet with my legs pulled over my head like a bunny rabbit and then wait for Danny to hit me across my exposed cunt and asshole or my flappy tits. She used a magic marker to write “I AM A COCKWHORE” and “I am training to be a slave” on my tummy after making me admit that I wanted that. Then she had me hold my mouth open and just when I expected her to spit in my mouth she spit right on my forehead.
I nearly had an orgasm!
“I can’t wait to make you go out like that and show you off as the slut you are, Mom!” Kristina laughed. My family laughed with her – they had no guilt about standing over me and looking down on me. They knew this was what I asked them to do and I was secretly glad. The alternative was that they would feel bad about what they were doing and I didn’t want them to feel guilty for something I consented to do.
I got my chance sooner than I’d imagined. “Who’s up for putt-putt and dinner out, tonight?” Kendrick asked as he joined the rest of my family in the living room with Jessica – she looked freshly fucked and happy. Her hair was a mess and she had cum dripping from her nose.
They demonstrated the question game for Kendrick, and he quickly approved but decided to call it an “Affirmation” of my place in the house.
“Do you like eating cunt, Drip?” Kristina asked as she pointed to Jessica’s well-beaten purple snatch.
“No, Ma’am,” I replied.
Chris beat me with his wooden backscratcher several times because he felt I must be lying when I said how much I preferred to give pleasure and suck dicks. I had to admit I hadn’t thought about it like that to them and apologize.
“So, you like eating ass and cunt equally as much as you like sucking dick?” Kristina clarified.
“Yes Ma’am,” I could have left the answer a simple yes or no but I had learned to offer my reasoning that afternoon. “I love to give pleasure – I am a cock whore – I am training to be a slave!”
I repeated the words she had scrawled across my belly – with a magic marker!
“We’ll see,” she laughed skeptically.
I’d had no inkling that Kendrick would want to have another family outing so soon again after the bowling alley, but then this outing was quite different from the last one for two reasons. The first was that this time, my family was truly having a full family fun night together. The bowling alley outing had been Kendrick, Danny, Chris and Kristina doing their thing and me and Jessica doing a sex bet while trying not to be noticed - or caught - by them. The second thing was that this time, everyone was on the same page and mine and Jessica’s roles were to be half the entertainment for my family.
Kristina had bluntly told me she was going to take full advantage of my head. NO! I don’t mean that she wanted what you’re probably thinking. That comment came as part of a bigger discussion - more of an argument, I guess you could say - between Christian and Danny. It wasn’t even an argument centered around me but rather this time, Jessica, or Fartbox, as they had quickly become used to calling her. Chris was upset that Danny had monopolized her at school and he said that wasn’t fair.
His problem stemmed from her red and puffy pussy and recently abused asshole, not to mention the welts and bruises she’d brought home. Chris felt that Danny had taken advantage by not including him in what he’d done with Fartbox at school. Danny’s defense was that Fartbox was a single toy, not three of them, and Kristina had taken his side. It had been more intense for me than anyone else, I think.
Even Jessica had taken part in the argument. I just knelt in the living room next to my oldest daughter, keeping my mouth closed and my thoughts to myself while they worked things out. Danny calling Jessica a ‘toy’ had triggered me. I imagined Jessica as exactly that, and my secret fantasy was away and running.
Jessica ignored the reference but had things to say about her position, too. She insisted that she was not to be ignored. That she was as much a member of the family as each of them were and, as such, had just as much say in how she could spend her day while staying within the boundaries of the new family rules.
Jessica’s not shy. She told them straight up that she’d do all the same things as me but woe betide anyone who took her for granted. She said she’d accept any punishment Kendrick dished out AFTER she’d taught her brothers a lesson that would leave their dicks in casts. Jessica always wants to be the center of attention. Me? I preferred to not be in trouble.
The Memory Enhancer didn’t even scare her. Kristina threatened to use it on her if she didn’t ‘remember her place’ and Jessica didn’t back down. What followed was a demonstration of Kristina versus Jessica and Jessica winning the round even after the Memory Enhancer had been employed several times.
Kristina’s attempts at belittling Jessica simply didn’t work. If Kristina had said some of the things to me that she said to Jessica, I would have been a puddle on the floor, a broken shell of a woman but Jessica? Not even close. Jessica just agreed that she loved to taste snatch and proved a number of times she’d do humiliating things without complaint, as long as her siblings respected her for doing them.
I thought things would come to a head when Kristina ordered her older sister to go get the roll of paper towels from the kitchen. Jessica acted for a moment like hell would freeze over first, but with little more than a nod from Kendrick, Jessica was on her feet. Then back down on her hands and knees at Kristina’s insistence. She crawled to the kitchen and brought back the paper towels.
At that time, only Kristina knew what the paper towels were for. Danny asked, suggesting that the roll was too big to be effective at beating sense into Jessica. Kristina just smiled and told him that he’d see soon enough.
Kristina made Jessica squat right there in the living room facing away from the three of them yet still right next to me. I’d had nothing to say, and Kristina praised me for being a good girl. It was humiliating receiving praise for simply kneeling naked before my own children and more so for the smile and the pat on the head Kristina gave me. I felt more like an obedient animal than anyone’s mother at that moment.
Chris made the most of the situation by having Jessica hold her butt cheeks apart. He told her he wanted to see her pucker, as if saying that was a way of reinforcing his ‘ownership’ of that part of Jessica’s anatomy. Jessica just laughed and did as she’d been told.
Kristina put a couple of paper towels on the floor between Jessica’s feet while she squatted, looking over her shoulder at her younger sister and boasting that she didn’t have a problem following orders, as long as she wasn’t ignored. Exactly the opposite of how I was feeling.
“Take a dump, Fartbox. I’m sure Chris would love to see you pump a turd out of your fart box,” she laughed, thinking that she’d finally, mentally bested her sister.
“I don’t need to go, but I’ll try. I can’t promise you’ll want to stay in the room after the effort though,” Jessica replied, letting rip a little fart right next to me before anyone could even react to the order she’d been given.
“Oh wow! Did you see her asshole flutter?” Chris asked no one in particular. He seemed the most excited of any of them. I just remained silent, although being right next to the source of a fart was NOT my idea of a fun time.
“What did you think it’d do when she tried to push one out? Open like an iris and be accompanied by glitter?” Kristina asked. Her tone suggested she was feeling annoyed that Jessica wouldn’t flat refuse to do such a disgusting thing in front of everyone. In fact, I think Kristina was beginning to feel sorry she’d ordered it. Her tone more suggested she wasn’t anything close to as excited as Chris sounded. She’d ordered it and Jessica was trying to comply without the least hesitation.
Jessica tried and tried. All she could produce was another couple of farts. I felt like she was somehow directing them at me. It was awful being right next to her. I bit my lip and remained silent.
“Maybe she needs a butt plug back in there to loosen up her asshole?” Christian suggested.
“How about a tongue instead?” Kristina suggested with a giggle.
“That’s not funny, Krissy. I’m not putting my tongue in Fartbox’s ass after it’s just had who knows how many guy’s loads of cum in there,” Chris thought his twin was suggesting he do it.
He hadn’t actually said he didn’t want to, just that he was grossed out at the idea of getting another guy’s cum on his tongue. I imagined Kendrick was jumping for joy inside, although on the outside, he just smiled a little.
“That’s what the other slut’s for!” Kristina giggled again. She still hadn’t settled on a name to use for me.
“Oh yeah!” Chris said as if he really had forgotten I was right there. Good idea, sis.”
“See? It’s your butt, although it’s part of Fartbox. We have to work together, dude,” Kristina said, then quickly explained why she’d agreed with Danny earlier. I was breathing a mental sigh of relief, thinking that now Kristina had made her point about how they each had an area of control and that they needed to work together. Right up till Kristina made her next comment.
“I bet a whore would love to get her tongue up in there and fish around for a little more leftover cum.”
“You mean Drip?” Danny supplied helpfully.
“That’s right, it’s Drip, now. I’d forgotten. But there are no other whores in the room feeling left out,” Kristina laughed, looking me right in the eye as she said it. I immediately lowered my gaze and blushed. It felt wrong to hold Kristina’s gaze. Just as wrong as the idea of putting my tongue in Jessica’s tailpipe.
“Well mom? Why isn’t your tongue already in there? You heard Kristina!” Chris grinned.
“She’s a little slow sometimes, bro. You have to tell her specifically what you want, or she won’t understand.” Kristina then focused on me. “That’s right, isn’t it, Drip? That little brain of yours isn’t so good at understanding big people stuff, is it?”
“Yes, Princess. I mean no, Princess,” I said, at first agreeing I would put my tongue on Jessica’s pucker, then realizing I was supposed to answer Kristina’s question. Kristina had said she wanted to humiliate me and I was feeling particularly humiliated. Still, it was easier to just agree with Kristina than to argue that I was not a simpleton like Jessica would have.
“See what I mean, Chris? She can’t even answer a question that simple!” Kristina said in triumph as if her previous attack on my intellect had been fully funded.
“Lube up Fartbox’s ass with your tongue, mom. I mean even if she still can’t poop, she’s getting a plug. Girls look good with something in their asses. I might use the foxtail. I think it’ll suit her,” he mused out loud.
“It seems more to me that she needs to be punished for not speaking clearly,” Danny put in. He went on to say that the rule was, I was supposed to immediately reply in full and complete sentences, and he mimicked my, ‘yes Princess, no Princess’ response in a really awful falsetto that was more about making fun of my reply than sounding anything like me.
“Well punish her tits then. I don’t want you putting welts and bruises on her ass and thighs like you did with Fartbox,” Chris said, sticking up for me.
I didn’t want to have my boobs slapped either, but at least my youngest son was doing his best to protect my overstuffed butt. That came out wrong. What I meant was that punishing my boobs terrified me. I didn’t want them spanked either. Still, it was clear my two boys still had things to work out between them, and somehow, I’d become a featured item in their argument. Kneeling there naked didn’t mean I would be forgotten.
I personally would have preferred to have been put in the corner as punishment, but I couldn’t bring myself to suggest it. It was just too embarrassing to suggest a punishment for myself even though I recognized that Danny had a point. I really had broken a rule, and I deserved to be corrected.
“There’s not much meat on those udders to punish,” Danny complained before his expression brightened. “I know, five minutes with binder clips on her nipples should remind her that she has rules now. Is that okay, dad?” Danny deferred to his father, rather than me.
I gulped when Kendrick again nodded. HE should try putting binder clips on HIS nipples before agreeing to allow Danny to do that to me, I thought. I had visions of massive clamps on my nipples, and I shuddered in fear. Danny must truly hate me if he was willing to cause me as much pain as I was imagining a pair of binder clips would provide.
Danny seemed to have read my mind. “This is for your own good, Drip. You said you wanted to get better at that, and I’m only willing to do it because I love you,” he said.
I didn’t understand. I couldn’t understand. How could my son be willing to cause a world of hurt because he loved me? If he loved me, he’d want to ensure I avoided painful things as much as possible!
“Come on, Drip. Were you lying, or do you REALLY want to be a better person? You don’t look happy about this at all and that hurts. Jessica let me whoop on her tits just because I wanted to,” he complained. “You want me to enjoy myself too, don’t you? Or is this all about giving Drip what she wants at no cost?” He asked.
His logic was sound, although I didn’t understand how he could admit he liked the idea of abusing my body. Would I or could I ever agree to let him cause me pain just because he wanted to hear my reaction? Where would it end? What if he wanted to nail my boobs to the wall? Would he expect me to agree to that as well?
“I know, I know, Drip. It’ll hurt like a motherfucker. But I haven’t even fucked you, so I’m not one. But it won’t ruin your tits or anything, and it’s five minutes for you to reflect on the cost of not answering immediately or fully. You’ll look forward to the Memory Enhancer once you’ve experienced this, right?” He asked. I heard the hope in his voice. He wanted me to agree instead of just subjecting me to his sadistic punishment idea.
“Thank you Sir, Danny. I appreciate the effort you’re going to, to help me. Of course, I’ll accept your judgement call on this,” I assured him.
“And?” He prompted.
What more could I add? I agreed to having my nipples crushed under the insidious clips! I’d even THANKED him! I looked at him blankly. I had no further answer to give. “I’m sorry, Sir Danny. I don’t want to be selfish,” I added, hoping that’s what he wanted to hear.
“Five minutes, Drip. Maybe it’ll prompt you to remember what you’re missing,” he insisted. “Now go get a couple from my desk, he told me.
I scampered away on my hands and knees, navigated the stairs and found the clips in his room. I admit I tried a couple of different sizes on my tummy before I bought a pair back. The tiny ones I’d grabbed first turned out to be the most hellacious. The biggest ones he had, hurt a bunch too, but not nearly so much. That surprised me and intimidated me more. They LOOKED like the ones that would hurt the most.
I got back and presented my chest to Danny, along with the clips. I’d never been naked so close to my oldest son before. I was glad Jessica had at least licked my face clean by this time because Danny didn’t hesitate to get right up into my personal space. My EX personal space, I guess you could say. My chest was heaving both from my exertions and from fear of what it’d feel like.
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