Chapter 10

“You know you could have said amber. That’s what it’s there for,” Rich admonished me quietly.

“I know, but I screwed it up the first time, so I promised myself I wouldn’t waste your time by doing that again,” I answered truthfully.

“Then how am I to know that you think you’re approaching your limits? If I’d gone just off your cries and your tears, I would have thought you’d reached your limit after the first two or three. Then I thought you were mocking me when you started giggling.”

“But that’s the whole point, isn’t it, Sir?” I tried to explain what had happened after I’d figured out the color I needed to say was amber. “I mean I kept thinking, one more and I’ll call amber, but I got so far I figured I could make it all the way through and I guess I did. At some point it stopped hurting quite so much, too,” I admitted as though I’d just revealed that it was me who’d stolen the last cookie from the cookie jar.

“Well now I’m doubly proud of you, slut. You used the rule perfectly. And who knows, maybe I’ll never need to punish you like that again?” Rich smiled at the idea as if he knew it wasn’t really possible.

“I hope not, Sir, but I wouldn’t hold my breath if I was you. I’m certainly not perfect although what you did right at the end, was. Even now, I feel so ... loved, I guess I’d have to say.”

I felt myself blushing, but I also felt driven to be completely open with Rich. If I was going to accept I was to be his slut for two weeks, I’d need to suck it up and get over myself anyway.

“I ... ummm I think I felt your thing against me just now,” I mumbled.

It could have just been the fly on his jeans that I’d felt pressing into my butt before I slid my fingers between us and had felt the aloe. Did doing that to me give you a boner?”

I couldn’t believe I’d just asked that! It’s something a sister should never know about her brother, especially if the sister caused that reaction. And he’s gay too! I think that’s why I decided to ask rather than pretending I hadn’t felt what I was sure I had.

Rich had admitted getting turned on seeing me naked but I wanted ... no I needed to know, if spanking me had turned him on separately from just seeing me naked. It would be something to ponder about if it did.

“Is that so bad? Am I an awful brother if I admit it was fun and made me hard?” He asked. He sounded defensive. “I’m not actually admitting you’re right, but if it was hard, does that mean you didn’t still deserve punishment?”

In my head, his words translated to, could I let him do the same thing again just because he enjoyed it, if it had in fact caused that reaction? My butt was burning, but I’d had that weird out of body experience that I didn’t understand and that was a little fascinating, almost enjoyable to me.

That thought led to an even crazier thought. Could I do something about his boner even though I’m his sister? He really has given his all so far, to working with me. But I knew I could never ask him if he’d let me do THAT and I chastised myself for even thinking things like that.

“For the next two weeks, I’m your slut, Sir. If you can’t bring yourself to discipline me when I mess up, I’m going to fail. If you enjoy it, I won’t be mad,” I assured him, hoping he’d take my answer in the spirit it was intended.

I snuggled for a few more moments then, without being told, I slid out from his embrace and into the Present position on the floor. I’d had enough time to recover from my well deserved punishment and I knew we had work to do before Rich would call it a night. I needed to get back to being Rich’s slut, not him being my cuddle bunny.

The moment I settled into position, I quickly lifted my butt off my thighs just a tiny bit so my cheeks weren’t being squished into the back of my lower legs and heels.

Owwwie! Luckily I kept my mouth clamped shut so Rich wouldn’t think I was complaining. But ooh boy! Was my butt ever going to be the same again?

“Okay, I suppose you’re right, it’s back to work,”Rich sighed as if convincing himself too. “But I’m the boss! You ask before you do anything, slut. Remember that!”

“Yes, Sir. I’m sorry, Sir. I just thought, it’s already after ten, and we’ve got school in the morning,” I justified my actions.

“Well, now that’s two things to remember, slut. Who’ll do the thinking for us?”

I knew immediately what he meant. “You do, Sir. Sorry again,” I said with a smile to show I wasn’t mad.

He was taking this game really seriously, and that’s a good thing. I’d meant what I’d said about needing his help and if he’d been only half committed like I might have been in his shoes, we would be screwed.

It’d still take some getting used to though, obeying my little brother but I’d learned two other things as well. First, he wasn’t dumb, and second. I had to stop thinking of him as my little brother but rather as my coach. A peer, not just a second-class member of the family. He’d certainly shown me that he wasn’t a second class anything as my butt kept reminding me.

“The second thing is that if you go to school tomorrow, you’ll be going just dressed in your undies and with a dunce cap on your head like in that movie we watched last month,” he grinned.

I knew what movie he was talking about. It was a comedy, and there was a scene where a guy woke up at school after getting drunk the night before due to a spiked punch at his friend’s party. In the movie he’d found himself waking up in the assembly hall in only his tighty whities and a great big white cone-shaped hat on his head with the word, ‘Dunce’ on it in big red letters.

Of course there was an assembly happening at the time, too. It was really funny watching it happen to him, but I would never have wanted to be in his shoes!

“What? You wouldn’t dare, Sir! Please don’t do that!”

I wasn’t sure if he’d really consider making me try to get to school in my underwear, hat, or no hat, but if it had just one result, it’d be to end his thoughts of bossing me around at school based on the agreement we already had. I’d get in so much trouble that the least result would be that he’d only be allowed to boss me around at home.

“Hello, slut. Earth to slut. It’s FRIDAY! If you head to school tomorrow you deserve everything you get!” Rich cracked up laughing and I felt about an inch tall. Then I giggled too. He was right about that!

We laughed together for a moment then Rich got serious again.

“I was thinking. About the amber thing. You said you thought about using it and you didn’t. That was perfect. But I’m not having you think it’s okay to use it just because you woke up on the wrong side of the bed and have a hair up your ass about something.”

“Okay, Sir. I understand. Does that mean you’ll punish me if I use the word?” I figured that’s what Rich was working up to, if he’d enjoyed spanking me.

I was already trying to resign myself to the idea that although the red and orange were our safety words, I’d still never be able to use them without major consequences. That was probably a good thing, though.

“I don’t want to punish you for carefully concluding you’re in too much pain. That would be a jackass move if you’re already hurting. No. I’d rather reward you for not using it when you wanted to. But I want to limit it more.”

I clearly heard the word reward and although there was not much I could think of that Rich could do to reward me, I liked the sound of it! I also didn’t know what he meant when he said he wanted to limit it, though.

He’d told me to call it out, tap my head or blink furiously if I needed to use it. Those sounded like the bare minimum already!

“I don’t understand, Sir,” I admitted.

“Of course you don’t. That’s why I’m going to tell you, slut. I’ll have to think on the reward part but what I meant by limiting it, is that it’s already limited to pain. You don’t get to call amber when I hurt your feel-goods. Sorry about your luck. I also think it should be limited to discovering your limits.”

“Okay, I thought we’d covered that. That’s its purpose, isn’t it?” I was confused that he needed to bring it up.

“I’ll give you an example. Tonight, I spanked your ass cherry red and more. It’s going to still be sore tomorrow. But you didn’t say amber. So, I know you can take thirty spanks with the hairbrush. If you were to get punished tomorrow with thirty swats, you shouldn’t be able to say amber, because you’ve already proved you can take it.”

I know my face lost its color. I felt a little sick. I couldn’t take another thirty swats right now! Another ten and I might be willing to say it!

“I ... I don’t know, Sir. You don’t know how sore my butt is right now. It was all I could do not to cry out when I got into this position and sat on my heels!”

“Yeah, I get that, slut. But you took thirty so I know that you can do it again in the future. I’m not saying I’d do it again to you while the pain’s still so fresh. That’d be like adding to a punishment that’s already been given.”

“Oh,” I said, relieved. “So, I can only say amber when you’re doing some new punishment?”

“Yeah, but not just punishment. Some of the things in the red pages are about tying a slut up and doing things with her asshole, pussy or other parts of her body,” he said. “That means you have to be able to endure them, and I don’t know how tight your ass is or how sensitive your nipples are. I need to find out. If you think I’m being too rough, you need to tell me, but keep in mind that there are minimum requirements to the pages,” he said, spreading his hands to express his dilemma.

Him saying that just made me want to see what was on those pages even more! I’d know without trying them, whether or not I would be saying amber. I didn’t need a fist up my butt to know I couldn’t take one!

“Can we study the pages together then, Sir? I will need to prepare myself mentally before I ever attempt things I’ve got to be able to do flawlessly in two weeks. I KNOW I WILL do them, but I need to know what to prepare for,” I promised.

And I had to get over the fear that was percolating inside me too. This list sounded scarier and scarier by the minute.

“Okay, but I have questions I’ll ask while we’re looking. And I liked having you up on the bed snuggled into me. So get that burned ass of yours back up here with the list,” he ordered.

I rose, picked up the list, then carefully moved back into his embrace without complaint, reminding myself over and over that I was just doing what I was told and there was nothing sexual about cuddling up to my brother.

I assured myself that some siblings cuddled all the time, and there was nothing sexual about it. The Russel twins were always holding hands, and no one at school ever accused them of being lesbians. They were just close sisters. I ignored the fact I was naked, and my nipples were again rock hard. The air was just cool in my brother’s room.

Rich put his head against mine so we could both see the pages he held with one hand. I could almost feel him breathing. He had no problem being pressed up against my side even though I was naked.

I needed to focus on the task at hand, not Rich’s hand casually cupping my boob as if there was no other place for it to go while he held me against his side. It didn’t help that the first section on the first page was devices and the next words read, ‘Torture toys - tits’. The words alone made me shudder.

“Whoa. Mr. J doesn’t know how to start a list subtly, does he, Sir,” I joked to cover my angst.

“Remember he said this list covers things a slut should be able to do once she’s been a slut around Jim long enough to learn all twelve positions. I imagine by that time, a slut’s usually been subjected to more than just this stuff, a few times over. So how tough are your titties,” he asked and then squeezed the one he was holding, as if kneading dough.

I hissed a little at how rough he was, but at least he didn’t have fingernails long enough to dig into my skin. I imagined that’s what it’d feel like if a sports masseuse was massaging a breast, and it was only the sudden squeezing that had caught me by surprise.

It didn’t really feel too bad. Kind of nice, to be honest, but I was also sure the nice would turn into not nice after a while if Rich didn’t let up. Those thoughts happened after another, purely instinctive realization hit me.

Oh God, my brother is squeezing my tits! I almost jerked away from his touch by pure instinct. I had to remind myself he wasn’t my brother. He was my coach, and he’d touched most parts of me already, while I was learning the first five positions. But he hadn’t manhandled me like he was doing now, either.

“That feels ... okay, I guess,” I admitted to Rich.

“How about this?” He said, releasing his grip and adjusting his fingers to squeeze my nipple until I let out a yip of pain.

“Sensitive!” I squealed but didn’t try to pull away even as he pulled my nipple away from my boob.

“For the demonstration, you’ll have multiple clothespins on your lovely udders, slut. These puppies surely are spectacular tits for your age, too. Have I said that before? None of your friends has a pair even close in size and yours are so plump, full and perfectly shaped. I like the tanline you swimsuit left, but I’d like to see a bikini tan line more. You know they’re almost as good as mom’s. I’d tell you if they weren’t.” He bragged.

It was uncomfortable hearing Rich say he’d spent time comparing my chest with my mom, but I already knew he had. I’d seen him do it. What I hadn’t known is that he had watched my friends’ chests too. Still, it was nice to hear him say he thought mine were the nicest of our group.

I already knew they were the biggest, but the nicest? He’d clearly never seen Megan’s bare, or Sarah’s either. Although hers are so small, she had to resort to a padded bra. Mine have been the bane of my existence since they’d started growing when I was eleven.

I’d never even started with a training bra. I went straight to an A-cup. Then after that, bras never seemed to fit perfectly until recently. And they are heavy too, lugging them around everywhere. But it was nice to have the verbal validation and not just jealous glances of the girls in the locker room at school that had made me reluctant to let mine be seen, even by my friends.

Rich released my nipple and moved his hand back to gently cupping my boob again. I sighed in relief. I could stand to have my boob cupped like that in his strong, large hand all night.

“It seems like I get to choose whether or not to put them on your nipples or just the areola and tit flesh on either side, leaving the nipple itself alone. But look at this,” he nodded to the page. “It says here, a row of clothespins are joined like a daisy chain with string, forming a chain of at least four and then they’re jerked free. That sounds like fun for me, but what’s the actual point?”

“Because it’s humiliating, degrading and might make me cry?” I suggested. “That seems to be the whole point of everything Mr. J does.”

“Yeah, I guess,” Rich said with a shrug like there was nothing wrong with Mr. J’s views. “We’ll do it tomorrow. Your funbags are big enough to hold six or eight each, I figure.”

“But you’ll start with just one or maybe two, right, Sir?” Having clothespins clamped to my boobs didn’t sound nearly as much fun to me as it did to Rich. But it was part of it, so I’d do it, even if I had to work my way up from just one on each boob.

“We don’t have proper nipple clamps either. You’ll have to be able to endure the alligator type ones for at least two minutes. But you’re a tough slut. I know you’ll be fine. I have some electrical clips in my science set. I’ll find them in the morning and we’ll use them.”

Rich clearly had more faith in me than I had. I was starting to think maybe reading through this list wasn’t so smart. It was just plain scaring me, and we were still on the boob section.

I kind of switched off at that point, comfortable enough just listening to the sound of Rich’s breathing, which was getting a little faster as he read about what I’d have to endure from instruments like a tawse, whatever that was, a flogger, which I could imagine and a cane, which made me gulp.