Chapter 29

My sister instructed me to clean up my bedroom. She made a big show about how I didn’t know what I should use to clean the carpet. Charity offered to teach me how to clean, but Lindsay said she would do it.

“You have your slave orientation tomorrow! Dad said you need to focus on that,” Lindsay told Charity.

“You are right, Ma’am! I am very excited and nervous!” Charity beamed with a look of enthusiasm.

“I am sure you will do fine,” Lindsay pet Charity on top of her head. It was patronizing, but Lindsay sounded genuinely supportive of Charity.

My Father focused on training Charity that afternoon. In a way, it was a lot of like physical fitness training but also education. He took her into the dungeon to do most of it. We did see him give her frequent and impromptu one-word commands. It was fun watching her spring up from the ground and snap into attention. Charity’s boobies bounced, and her ass jiggled with an elastic perfection.

Lindsay took me upstairs and lectured me on how to clean my room as she did.

Once we got up to my room, she laughed wickedly. I was holding the steam cleaner and some spray bottles.

“You did very well, Matt!” She patted me on the head in the same fashion she had Charity, but she didn’t seem supportive at all.

“I did what you asked! You said that you wouldn’t tell Dad what I did last night, but you made me lie to him!!” I seethed with anger.

“Tut-tut!” Lindsay wagged her finger in my face and shushed me. “I want you to call me Ma’am or Miss Lindsay!” she looked overjoyed.

My mouth fell open in shock.

“I didn’t think I’d enjoy that as much as I did. I think I’d like Simon and Lucy to call me Miss Lindsay as well. After all, I am the authority figure when Dad isn’t home!” she mused.

“You promised you would leave them out of this!” I reminded her angrily.

She wagged her finger at me and made me say “Miss Lindsay” before she would answer my question.

“I promised you nothing, and you were the one who CHOSE to lie to Dad when I asked the questions. I won’t make either of them ask to submit, but you are going to do that later today. You liked getting spanked. I could feel your gross little boner dripping cum on my knee. Did you think I didn’t notice? You think Dad didn’t notice?” she asked.

“If Dad had noticed, he would have stopped it,” I insisted.

Lindsay slapped me across the face - hard! “Do you need another reminder of who you are talking to?” she asked.

I should have slapped her back. It was so abrupt and shocking that she reached out and slapped me like that.

“No, Ma’am,” I cradled my face. The pain stung - much worse than it had on my ass.

“Your bony ass hurt my hand, but damn! Your jaw must be made out of marble!” Lindsay shook her hand as if it hurt. I was glad it did. “You think this is a picnic for me? I had to watch a grown woman squat and piss like a dog while she preened and mewled like an animal. I had to touch you physically!

“Then, don’t do this!” I pleaded and added the “Miss Lindsay!” when my sister narrowed her eyes at me.

“This is happening. Things are already in motion. You will clean your room. You will come down and eat lunch. You will call me Ma’am and Dad, Sir. You will say it is because you accept that we both know what is best for you - just like a teacher. You don’t call a teacher by their first name. You call them Miss or Mister. I’ll say how much I appreciate you and respect you for that. You think it is easy for me to lie to dad about how much I respect or appreciate you?” she giggled wickedly.

“What then? I have to strip naked and beg to submit like Kyle, Ma’am?” I begrudgingly called my sister Ma’am.

“Yes! That’s a great idea,” Lindsay pat my head again. She was clearly not afraid I’d knock her block off for touching me. “I didn’t think I’d like to see you naked around the house. However, watching you waddle around with your underwear and shorts around your ankles was the highlight of my morning. It was a great touch! I loved the expression on your face. You looked embarrassed, but at the same time like you were seeking our approval to be naked. I thought Dad was going to freak out when you had a boner. He was uncomfortable like the rest of us, but you can get away with it as long as you stand in the corner anytime you get a chubber. Yes, take off all your clothes and beg to submit to HIM. Tell him some bullshit about how you want to learn to be gracious, humble, and all that stupid shit. Tell him you want to help around the house and be a good boy, and the only way you can do it is if you lose some of that ego of yours!” she chuckled.

“He isn’t going to go for this!!” I insisted before reluctantly calling my sister Miss Lindsay again.

“He probably won’t, but you are going to ask. I’ll reluctantly volunteer to help keep you in line just like I do Charity. Oh don’t worry,” Lindsay noticed the worried expression on my face “I won’t make you piss like a dog. I will probably ignore you for the most part. I’ll make a show of giving you some chores and assignments to do. Don’t worry! I won’t cage you in the living room or anything like that. At night, you can still sneak out with your little girlfriends. This is just pretending. I will make a show of making you behave and do your homework at school too! You know I really don’t care, though, right?”

“Yes, Ma’am,” I agreed she didn’t really care whether I learned something or not.

“If you fuck up and get bad grades, or misbehave, then Dad might blame me. I’ll apologize and say I wasn’t strict enough, and THEN I’ll make your life hell,” she said.

“You said that I only had to do this for two weeks, Ma’am,” I reminded her.

“Yes, I did. Two weeks should be sufficient to make Dad believe I am capable of running the house,” Lindsay mused.

“You are making it sound like this is permanent, Ma’am!” I complained. “There is more to this than just being able to come and go as you please!”

“Very clever,” Lindsay looked impressed. “I will ride your ass for two weeks. If you fall in line and don’t give me any reason to continue, then I will stop. I have bigger and better things to do with my time,” she said.

“What was the real reason you did all of this?” I wanted to know why she went to all of this trouble.

“You like to think there is some grand plan for everything. I did this because I could. It is really that simple. I wanted to come and go as I please. However, now I realize that I’d like a toad for a pet. You are my toad. In fact, I’d like you to ask Dad for a submissive name today. I think Toad would fit you,” she chuckled.

“I am not doing that, Miss Lindsay!” I insisted. The fact I just called my sister Miss Lindsay when I challenged her authority probably made it seem less than convincing.

“I can make Simon or Lucy be my toad if you won’t do it. You’d like to see Lucy as a toad, wouldn’t you? She can do the splits in the nude and dance around for my boyfriends when they come over! I bet she’d get off on it!” Lindsay promised me.

“You wouldn’t dare do that! Ma’am,” I insisted.

“You have no idea what I would dare to do. I probably wouldn’t invite my boyfriends here anyway. I don’t like competition. Lucy is cute, and Charity has an amazing set of tits. I might invite over guys I want to use, though. If they have something I want, then I might let them have a little fun with Lucy or Charity,” she chuckled.

“You wouldn’t do that to your little sister, Ma’am!” I implored Lindsay to take it back.

“I noticed you didn’t mention your precious slave Mom just now. You’d be okay if I made her serve my friends? Just not Lucy?” she chuckled.

“No, I mean yes, Charity would because she is here to serve. She’d serve whoever walked in the door as a guest. I know you are evil, but you wouldn’t blackmail Lucy into that! That is beneath you, Ma’am!” I said.

“Oh? You may be right, Toad! Dirty work like that is beneath me,” Lindsay chuckled sardonically. “Would you blackmail her for me then? That could be fun. I could trade your freedom for hers,” she said.

I said I would never do that.

“Then you have the job of Toad until I decide you don’t. Look, you would do the same thing to me if the shoe were on the other foot. So would Lucy and Simon!” she said.

“We would never do something like this, Ma’am!” I insisted.

“Oh? so if I marched downstairs and stripped naked and begged Dad to allow me to submit around the house, you wouldn’t take advantage of the situation?” she smirked knowingly.

I wanted to tell her I wouldn’t, but she knew I wanted payback.

“You’d make me do all sorts of pervy things!” It was as if she read my mind and knew that I was thinking about jamming the biggest object I could get up her ass.

“Lucy and Simon wouldn’t, Ma’am!” I defended my little brother and sister without admitting that I’d spank the shit out of her if I could.

“Did you see Lucy squealed like she just got tickets to backstage at a One Direction concert when Charity became a table for her? Lucy enjoyed Charity providing her undivided attention and doing whatever she told her. If I had to listen to Lucy’s insipid prattle and pretend to enjoy spending time doing whatever she wanted, it would be more torture than letting you stick your dirty finger in my mouth and play with my tits!” she insisted.

Lucy didn’t seem sadistic, but she did enjoy treating Charity like a human pony or a table. I could definitely see Lindsay’s point.

“Simon is all about making a buck in the quickest way possible. I am just lucky I’ll graduate before the little fucker is in High School next year. I wouldn’t put him past him to rent me out for dates with nerdy boys!”

Lindsay described an online dating site called “SugarDaddies.com,” where pretty girls meet up with men with money. “He probably set up a nerdyboys.com just like it. Then boys would bid money to take me out on a date. I’d have to go out without any panties or bra and be nice to them. Not give them any guff for the entire date and at the end give them head or something,” she was very specific.

“You seem to have really thought this out,” I said.

“Simon and I are a lot alike. I know how his reptile brain functions. If he could exploit me, then he would. I respect him for that. I would do the same to him if I thought there was any value in it,” she admitted. She noticed a bulge in my shorts.

“Take your pants down,” she chuckled and insisted I take my shorts off. The door was shut in my room, but I did as she told me.

“You are hard! Did you get hard thinking about me getting rented out to strange boys? Or you got hard wishing I would rent you out to them?” she laughed.

It had been a combination of things, but I had pictured her renting me out to hard-up girls - NOT boys.

“I want you to shave all your pubes, including around your balls while you are up here. It will make it more obvious you put some thought into this when you ask dad later. You do have a razor, don’t you? What am I saying? You haven’t started growing hair on your face yet. I’ll get you a razor, but I am not going to teach you how to use it!”

I stood there with my shorts around my ankles, waiting to be told I could put on clothes.

“I want you to finish and come down fully dressed and ask me to inspect your room. I’ll give you the signal when I want you to ask Dad. I don’t want it to be too soon. I want you to strip while you are asking to make it more dramatic. You can pull your shorts up now, Toad,” Lindsay said.

I did so without a word.

“I want you to say Yes, Ma’am, when I tell you to do something,” Lindsay waited for me to acknowledge her answer with a Yes Ma’am before leaving my room.

My first impulse was that I wanted to knock everything over and yell in a furious rage. I restrained myself, though. It was probably what Lindsay wanted. She had played me for a chump. If I suddenly started acting resentful and angry, then she would find a way to use that to her advantage.

It still seemed surreal to me to ask to submit around the house. I couldn’t picture my father allowing it. I thought that my best option might be to go overboard and ask for the full Kyle McGifford treatment. If I asked for way too much, then my father would never allow it. The problem with that strategy was that if he did, then I’d be stuck. It was a real pickle.

The safest thing to do was to ask my dad to let me submit around the house. I’d have to listen to my sister and clean up, but she promised she’d leave Lucy and Simon alone. She also promised she’d let me do what I want at school and after hours. The question I struggled with was, could I even behave with the least amount of submission possible with a straight face? Could I ever look at anyone in the house in the eyes again after I did? There were so many unknowns to this idea. Would I have to call Simon and Lucy, “Sir” and “Ma’am”? They would laugh at me!

Lindsay had built a precarious house of cards here. If it all fell apart at some point, it might land on me. She could still reveal all the humiliating blackmail she had on me and implicate me in all of it. If she could pull it off, she might still end up pulling Lucy and Simon into it.

Lindsay clearly was the kind of person who wanted to get someone before they could get her. If either of them challenged Lindsay’s authority, they could end up in her crosshairs as a target.

I felt it may be best to go to my father and just tell him everything. I would have to own the blackmail she had on me, but then she couldn’t weave an even bigger web and ensnare everyone in it.

I have to admit that the only thing that prevented me from storming downstairs and doing that was the fear of his reaction to my part in all of this. I needed time to get my courage up, but there was another knock on the door. I had not even started to clean yet!

It wasn’t Lindsay because she would have just walked in. She did tell me she was bringing me a razor, though.

“Hey Cowboy,” Claire said as she stood in my door. She was dressed in a sexy half-top and a pair of denim short-shorts with holes in them. She had a green sack in one hand.

“Usually, when a hot chick knocks on a boy’s bedroom door, they don’t make her wait in the hallway,” Claire McGifford smirked at me impishly as she noticed the stunned look on my face.

“I am sorry! I just had a lot on my mind and thought you were someone else,” I said.

“Oh? expecting other girls?” Claire picked up my sheets and sniffed them. She could smell the sex on the sheets and looked at me like she was impressed.

“No, nothing like that! I just had a lot on my mind,” I welcomed her into my room. My mouth became dry, and my heart started racing. Claire exudes wanton sexuality and promiscuousness. I was shocked my Dad let her come into my room.

“Me too! A lot came to a head last night after our dinner at your house,” Claire smiled coyly at me and plopped down on my bed and luxuriated.

“Is that for me?” I asked of the green sack.

“I don’t think those things would look very good on you,” she mused that it might be interesting for me to try them on anyway. Claire stopped kidding and said the sack she brought with her was the reason she was here.

“I have some bad news, Cowboy” Claire writhed on my bed like she was testing it out. I wanted to join her, but I was still too stiff and shy. I didn’t like the sound of bad news. I already had enough of that today.

“We won’t be able to go out on our date on Friday after all,” Claire said.

That tears it! I officially had the luck of Charlie Brown, and Claire was my Lucy all along. She had held the football out for me to kick the winning goal, and then at the last minute, when I went to kick it - she yoinked it out from under me, and I landed flat on my back! This was just par for the course.

I began to wonder, had she ever intended to go out with me? Had I been some sad joke? Had she taken pity on me when I asked her out, and then after she realized I wasn’t even close to the kind of guy that was in her dating league, she realized she couldn’t go out on a date with me?

She unsnapped her shorts and started to wriggle out of them.

“I thought we might as well go ahead and have sex now since we would have after the date,” she looked up at me hungrily and removed her top.

I was stunned. Claire was already undressed, and she pulled on my shorts and tugged them down. My dick was rock hard, and she looked pleased.

She pulled me down with her on to the bed. We began to dry-hump and cuddle.

“You looked disappointed when I told you we couldn’t go out on a date, Cowboy!” she said as she kissed my nose. “You really wanted to waste all that time getting to know me when we could have just been doing this?” she said as she ground her hips against mine and gyrated. She let her pussy lips glide up and down my cock without inserting it.

“Will we be able to go on a date another time?” I asked politely as I pressed my body to hers.

“No, I am afraid not,” Claire looked me in the eyes sweetly like I was very naive and innocent. She didn’t look down at her nose at me. It was more that she envied me.

“Can I kiss you?” I swooned. I wanted nothing more than to kiss her.

“Normally, I think it is gross, but I wish you would. Do whatever you like. Anything goes - Just no anal, okay?” she asked like it was a favor.

I answered with a wet sloppy kiss that lasted way too long. I sucked her teeth and tried to jab my tongue down her throat.

“Please keep doing that. It is nice,” she whispered.

I was shocked my Dad let a girl come up to my room. I wondered if this was another of Lindsay’s tricks. I half-expected her to come walking in with my father and point out that instead of cleaning, I was boning and demand to punish me. I even wondered if Lindsay was in on it the entire time.

Something in her kiss told me she wasn’t. She wanted me! I could feel it. I slipped my cockhead into her tight pussy.

“No, foreplay! straight in?” she was half-smiling and half-annoyed.

I realized I should have done something else. I assumed use my fingers or go down on her. I started to pull out, but she held me close and pushed down on my cock.

“No, let’s do this your way, Matt. You are fine,” she said as she rode my cock like it was an honor. She kissed me and rolled over on top of me. “Do you mind if I fuck you like this?” she asked sweetly. I didn’t.

“I am in control when I am on top. I can go as slow or as fast as I like,” she beamed with happiness. She turned around so that her ass was facing me and leaned forward and then back onto my cock. Every time she did, her asshole spread open. I wanted to play with it and stick something in it. It looked pink and puffy like she had just played with it.

“I appreciate you letting me do this, Matt!” She said as she fucked me at a medium pace.

“I appreciate it, too,” I said. It sounded so awkward and stupid when I said it, though. It was like the fumbling words of someone who was talking about borrowing someone’s Xbox controller and not their first time having vaginal sex.

Claire smirked as if she expected me to say something silly and awkward.

“I am going to miss this, but I am glad you are my last. I feel like you are ready to pop. Are you ready to cum for me?” she asked.

My cock was bulging and ready to explode minutes ago. The vision of Claire impaling herself down on my cock was sending me over the moon.

Her ass cheeks spread open each time she drove herself down on the shaft of my dick. Every striation and muscle in her sexy back was visible as she worked herself to an orgasm of her own with my dick as her plaything.

“I am! Why are you going to miss it?” I asked, and at that moment, I had an explosive orgasm inside of Claire’s slick pussy like nothing I had ever experienced. It felt like for that perfect moment, I was in the center of the universe, and everything was right. I felt like a man - like I had just spread my seed and fulfilled my biological purpose on the earth. It was primal and awesome in a way like nothing I had ever known. I usually felt shame after masturbating. Still, in this instance, I knew only this urgent need to pull Claire towards me and hold her tightly.

“You will see,” she let me hold her tight and smiled spritely. “Oh, you like to snuggle after you cum! Such a sweetheart! You are going to make some nice girl really happy, Matt Camden!”

I didn’t want to be a sweetheart! I wanted to consume Claire like a wolf would after he hunted and cornered a rabbit. I felt like she was telling me she was never going to see me again, and yet after cumming, I felt nothing but euphoric pleasure.

She slid off of me and said that she had already taken too long. “I asked my Father’s permission to tell you before I became Temptation. I didn’t ask for permission to fuck you,” she said as she dumped out the contents of the green sack on the bed.

I laid there still basking in the feel of her pussy as it gripped my dick and massaged the cum out of it. It had felt like she coaxed it out at the end.

Claire licked her fingers after touching her pussy and slid off of me. She thanked me for a very sweet fucking. “I will definitely remember that, Sir” she laughed to herself. Claire upended her green bag onto the bed and emptied it.

She told me that it was time for her to say goodbye to Claire and hello to Temptation. I didn’t understand what she meant by that.

The contents on the bed confused me as well. Claire had a leather collar, a butt plug, and a stainless steel chastity belt. I began to panic that she was working with my sister and intended to make me wear them downstairs.

It dawned on me she meant she fucked me for the last time because I’d be in some kind of chastity belt that prevented sex.

“If it is alright with you, I am going to lock this on with your cum still inside me as a little reminder,” Claire started to put the belt on herself. It was designed for a female to wear. The metal belt locked in place and had a tiny slit in the front with metal grippers like the ones Charity had attached to her clit this morning.

“It will be our little secret,” Claire smiled down at me while I tried to recover from my recent orgasm and make sense of what was happening. “I did you as Claire, not Temptation,” she laughed and then tightened the belt and snapped it in place.