Chapter 17

Master Thorne took a long sip of his frozen drink and then set his glass down on his slave Ruthie’s back. The older slave was at his feet, serving as his table. The most interesting thing to me about Ruthie was that in the face she looked like the type of person who would send everything back at a restaurant and be a real tough bitch. However, while she was at his feet she seemed docile and tame. She reminded me of a tiger that appeared to be rendered harmless by their trainer. You know they could shred you in just a few seconds and if you look in their eyes you can see the smoldering fury that once knew no limits.

Yet, the tiger was now a pussy cat that thought only of trying to please her trainer! The expression on her face was mild annoyance at best. She wasn’t judging us and she didn’t seem concerned about what just happened.

The expression on Master Thorne’s face suggested he had entirely run out of patience with us. Unlike Ruthie, he definitely was judging us and we had not measured up. I had not handled my slave and my slave had done the unthinkable faux pas of launching her butt plug out of her ass after an unbridled outburst of laughter.

I felt the old master’s eyes burning into me as if he were enjoying my bewildered indecisiveness. He had an intimidating bearing about him and his slow very deliberate movements made me instinctively pause and wait for him to react. It was as if I needed to know what to do from him simply because he made me feel like he knew much more than I did and his approval was important to me.

Charity was frozen on all fours in a panicked state. Time felt like it slowed down as she looked up me with tears in her eyes and repeated apology after apology. She had just shot her butt plug out of her ass after a hearty laugh. It didn’t seem like that big of a deal to me but everybody’s body language including hers made it clear it was.

I also felt the attention from others seated in our general vicinity, including the slaves parked nearby in squatting positions who were probably laughing at me for looking completely out of my element. No one said anything, and I heard no laughter. Can you imagine people laughing at you and mocking you without saying a word? That is how it felt.

Dicktatress Moxxi watched me standing over Charity with a puzzled look on her face. She may not have heard the joke at her expense or she simply didn’t care that I had made it. She shrugged and told her daughters that the food was getting cold. The apathetic shrug as she turned away was almost as bad because it was as if she had just seen a car wreck and said there was nothing to be said and nothing to be done. She had her own problems and didn’t want any part in mine.

“Is that the boy you snuck out to see last night?” Moxxi asked Stacy as they walked away.

“No!” Waverly insisted as they walked away and after a knowing stare from her mother, she admitted, “Yes, but how did you know about that? did one of my dads tell on me?”

“No, you just told on yourself. That boy is way too old for you anyway,” I heard her tell her daughter. Stacy had told me she was in the same grade as me and if I wasn’t in such a panicked state about Charity’s predicament, I might have realized that was probably another of Stacy’s lies. Stacy had also told me Bambi was around my little sister’s age, and while they both seemed more mature than Lucy, I didn’t have time to think about that right now.

Stacy reached behind her back and stuck her finger and thumb into her butt crack. She made a motion with her fingers like she was pulling an imaginary swim suit out of her crack. It was probably just a nervous twitch.

“Stop playing with your butt,” Moxxi chided her as the three women walked back towards where the rest of their family were at the pool. I would have loved to watch them wiggle their big asses all the way back but I had to address what just happened.

“You need to be punished,” I observed as I crouched down and looked between Charity’s legs at the wide-gap in her anus and directly at her pretty, wet pussy quivering in the sun. I felt it was what I was expected to say. Charity had all this remorse on her face and in her body language. She pouted and nodded her head without argument. Charity’s expression of timid resolution to accept whatever happens next was enough to tell me she accepted that I would be the one to punish her.

I looked at Master Thorne to seek direction. He returned my look with an expression that was neither approval or disapproval. The fact that he did not intervene suggested to me that I should punish Charity myself.

I felt terrible for Charity because the flap of her anus was stretched open and she must have been intensely humiliated knowing that people could see inside the hole she poops and farts with. There was something so vulnerable and raw about a sexy woman being obscenely exposed that way and not immediately trying to cover it with her hands. She waited compliantly for me with legs spread like I was a doctor inspecting her body to make her all better. My calm words seemed to make her even more passive and accepting of what would happen next. I couldn’t believe that my words made her calm. The part of me that lacks confidence wanted to believe she acted calmly when I spoke to her to help ME feel less awkward. If that was the case she was the greatest actress of all time because her tits and cunt flaps stopped quivering and her entire demeanor shifted from panicked guilt to contrite and reserved.

Either way, it worked, and I tried to take control of the situation. I had to stop thinking of myself as a kid completely out of his element.

“Yes, Mister Matt, I understand. I am sorry for my mistake. I should not have been listening to your jokes, and I wasn’t concentrating on my role here,” Charity sniffled like she was crying. “I know I embarrassed you and the family and I accept whatever punishment you think will teach me never to unclench my anus in public again!”

I didn’t mean she needed to be punished by ME. I was thinking of Master Thorne or even Squire Carlos. He and his family were watching from the nearby blue cabana and waiting to see what I would do.

I knew that Dad hadn’t given me permission to punish her. He also hadn’t give her permission to be disobedient. I had created a barrier in my mind that I felt I should not cross and this felt like it was on the forbidden side.

I could imagine my dad with his arms folded, looking at me with disappointment, and I knew it was wrong to punish her. At the same time, I could see everyone else with their annoyed expressions, judging me that I hadn’t done it already.

I made a snap decision at that moment. With all the attention focused on me, I had do something. All I knew was whatever I was going to do I had to decide in that moment. “Lead, Follow or get out of the way,” was a figure of speech my father said all the time. Getting out of the way wasn’t an option and no one was telling me what to do. I had to lead and that meant making a decision.

Strangely, It was something Lindsay had said before about it being better to ask forgiveness than permission, that helped me to decide what to do. I couldn’t ask Dad’s permission right now, but given the circumstances, Charity had to be punished, and no one else was going to do it.

“Fine, you need to be spanked,” I decided. I had seen plenty of punishments since I arrived, but the one that everybody knows as the most basic is probably spanking. It still felt taboo that I should spank another person. I was, after all, only a teenager and had never done that to anyone else. My Dad hadn’t spanked me since I was very little and even then it happened pretty rarely because I was always in Lindsay’s shadow and by comparison, pretty well-behaved next to her.

The only reservation I had was that Lindsay had told me to spank Charity and be mean to her.

I crouched down where she was on all fours. Snot rolled down Charity’s nose, and she looked pathetic. She couldn’t look right at me. “Please, Sir, forgive me!” She was sad.

I felt in that moment it would be crueler NOT to punish Charity. I might have had sympathy for her if being spanked was not fair. I reminded myself that slaves get spanked in public for things like this all the time and Charity wanted more than anything to be a slave. Charity seemed to NEED to be punished in order to feel any redemption about what she did.

I pushed any guilt or second thoughts I had about proceeding from my head. I divorced myself of sympathy for Charity as well. This should be over quick and it wasn’t going to kill her. I had heard Charity scream in agony for hours in the dungeon last night. Charity looked like she came out of that session more in love with my father than when she went in! Any pain or humiliation Charity felt from this punishment would pass.

I popped my slave mom on her butt with the flat of my hand as hard as I could. “One!” I counted, and then I began to do another and another. I felt some of the guilty feeling of people staring at me melt away. I felt relieved that I had acted instead of standing there like an idiot. It felt good to be touching her butt with the flat of my hand. Charity stuck it out for me as if offering her ass to me to do with as I pleased. My palm touched both the rim of her stretched out asshole and her pussy flaps. I could feel the piercing on her clit on my hand. I was smacking her butt and being careful not to hit her hard enough that she would get angry or cry out. I spanked her ass like I was slowly playing the drums on her butt. I imagined her ass cheeks were a pair of bongos.

I felt a sense of redemption for doing this now that I had begun the punishment. I had made a decision and followed through. I felt pride in myself for that.

All I had to do was deliver at least seven more of these swats, and this would be done and over. I felt silly for overthinking the punishment. A weight was lifted from my shoulders because what I was doing felt like nothing at all.

The thing I didn’t realize at the time was that punishment wasn’t supposed to feel like nothing at all. I was doing it all wrong.

“Son, if you want to kill a mosquito you will have to hit harder than that,” Master Thorne was standing over me, looking down. “I assume that is what you are doing?” he wasn’t smiling. The Master was condescending, but he was absolutely right.

I wasn’t doing much more than getting my hand sticky by smacking her butt. The unfulfilled look on Charity’s face suggested she agreed with Master Thorne. Charity had complied with the punishment without once complaining. The look on her face suggested to me that she was disappointed that this was all she was receiving in the form of punishment. I don’t think she wanted to enjoy the punishment but I got the distinct impression she felt this was hardly a punishment at all.

“Do you want some help, Son?” Master Thorne asked me charitably. He wasn’t amused and he was looking down his nose at me like I was a clueless newbie. He wasn’t wrong – that is exactly what I was.

“Yes,” I said and paused the buttslaps I was giving Charity. They were ineffective anyway.

“What is your name?” he asked me, and I told him it was Matt. I introduced Charity as my slave mom. I liked that term that Stacy used, and Master Thorne didn’t question it.

“Well, Matt, you know there is no shame in asking for help. We are a community. I can see you are struggling here and I’d like to help because this is quite frankly, painful to watch.”

I stood up and asked him to show me how to punish Charity.

“No, I am NOT going to do that,” he said. “I did that earlier, and you and she didn’t learn a damned thing from that. Why would I repeat the same action and expect a different result? We tried the osmosis method. Now, we are going to try the hands-on approach,” he told me very rationally.

I assumed by osmosis Master Thorne meant that I could pick it up just by being around how real discipline works.

“I heard her apology and your mom has a lot of work to do giving one, and you have a lot of work in learning when to accept one. I am going to skip that lesson for now. We all saw what she did and why she did it. Did you tell her what her punishment is going to be?” he asked me.

“Spanking,” I said. I was nervous about talking in any greater detail. I thought it had been obvious because I had been spanking Charity’s ass all this time.

“Is that what you were doing?” Master Thorne’s deep voice revealed a trace of condescending humor. “I thought you were trying to bore the lovely creature to death. I see it now, yes I suppose you were trying to spank her,” he said. I saw Ruthie suppress a laugh from back at Master Thorne’s table where she remained dutifully on all fours.

I didn’t argue or stick my tongue out at him. I accepted that I didn’t know what I was doing and he was absolutely right.

“The carpenter’s toolbox has a tool for every job. If all your problems are nails, then you only need a hammer. Not every punishment should be spanking. There are many ways to correct a misbehaved slav when she makes a mistake. I am going to teach you how to apply a spanking like a Carpenter. The first step is to understand that Carpenters don’t just nail things into walls willy-nilly with no plan. They measure them, and they know specifically how many nails they need to do the job. How many spankings do you think she needs?” he asked.

“Ten?” I answered with a guess.

“Like the commandments? It is a nice round number, I suppose, and it was good enough for God. If it were Ruthie I’d do a hundred, but Ruthie would never release her plug without a strong hurricane-level gust or a solid yank from our paperboy,” he chuckled.

Ruthie maintained a stony expression when Master Thorne mentioned the paperboy. I wondered if he was kidding or he invited the kid who delivered their newspapers to try to pull her plug out. I imagined a boy about my age drawing Excalibur out of Ruthie’s ass and Master Thorne dressed as Merlin declaring him the new King of the Britons. I tried not to chuckle at that mental image and pay attention to what Thorne was telling me.

“The punishment needs to be appropriate and commensurate to what the slave has done — in this case, spanking, while not very creative, is appropriate. On a scale of one to ten with one being the minimal corrective measures and ten being the most intense but appropriate punishment, what do you think is warranted here?” he asked me my opinion.

I had no idea! Any answer might be the wrong answer. Master Thorne carried himself with a quiet confidence like an Army Colonel and my instinct was that to say one on a scale of one to ten so that I could apply the simplest punishment. I had the least chance of fucking up something simple.

I was already nervous about my father finding out. This question eroded my resolve to punish Charity and made me feel like I shouldn’t be the one making the decision. I felt that if I couldn’t even decide how hard Charity should be punished how could I be the one to deliver the punishment?

I could still pussy out and say that I didn’t want to do this at all. Something inside told me that I had to do it and that stopping was still not an option.

“Five?” I asked for something in the middle. I was asking Master Thorne, but I was looking at Charity’s gaping asshole while I said it.

“Are you talking to me? Then look at me when and engage me. The answers you seek aren’t in that slut’s dirty little asshole,” Master Thorne shook his head and snickered.

I wasn’t so sure about that. I was fascinated by the gap in her anus. I felt ashamed for being caught looking up Charity’s unplugged asshole again. The black rim forced her asshole wide but hid all the mysteries inside that hole from plain view. It was usually plugged and it looked so vulnerable and exposed right now.

I was tempted to continue to look at her asshole but instead I repeated my response of a five on a scale of one to ten as I looked right at Master Thorne. I did so this time louder and with more confidence in my voice.

“A five would translate to about fifty solid swats but since I have a frozen drink and I don’t think you have the will or desire to follow through then how about we double what you originally intended to twenty swats? Ten swats are at best a warning and not a correction.” he suggested.

I nodded that was fine. I wanted the Master to just tell me what to do next. I was confused, inexperienced and simply lacked the confidence I’d make the right decisions. I wanted to be like Master Thorne and my father but I still felt I was just a dumb kid and at any moment Master Thorne would realize that and tell me to go home.

Yet, Master Thorne treated me more like an inexperienced young adult who needed guidance. It may have been humiliating for someone with more ego but for me it was a huge step up.

“Go ahead and inform her of her punishment and tell her to collect her unsightly plug. We mustn’t leave that lying around for someone to step on,” Master Thorne told me.

I couldn’t believe he was asking me to tell her to crawl over and pick up her butt plug.

“Son, Are you hard of hearing? If so, Ruthie is an expert in sign language. I am not in the habit of talking twice and repeating my instructions. If you don’t want my help there is an ice-cold Margarita over there I’d rather be spending time with.” Master Thorne had patience for me pussy-footing around with this any longer.

It wasn’t lost on me that Ruthie was over there as well and had specifically said he wanted to spend time with the Margarita instead of her. I assumed she knew that he meant her as well and I got the very distinct impression that under Master Thorne’s gruff exterior was a loving teddy bear of a man that was delighted his wife was his well behaved slave.

“Crawl over there and get your butt plug,” I sounded shaky.

Master Thorne wasn’t’ overly critical. He told me that my instructions could be more specific as we watched Charity turn and crawl like a lizard slithering across the hot cement.

I noticed there was a little fudgie-like drip of brown on the black turnip shaped buttplug. It looked quite a bit larger once it had popped out of her ass and clattered on the ground.

Charity hesitated for a moment, and I was going to point out the fudge stripe on the plug, but Master Thorne shushed me. “You have done your part. Let her follow your instructions,” he spoke to me softly that I should just go with what happens next.

Charity lowered herself over the plug and picked it up with her mouth. She clenched it in her teeth and crawled back to where she had been before. She had just degraded herself by following my instructions, and there was no going back now. I had officially given her an order other than a core position command, and she had followed it.

The fudge stripe looked like the drippings of a Popsicle after a warm day on the black rubberized turnip. It didn’t seem overly disgusting or like a big wad of poop but I knew that it came out of her ass. I was shocked to see her pick it up and grip it in her teeth without any reservation. I decided not to say anything more about it. It both excited me that she had done it and puzzled me that she didn’t freak out about picking the dirty sex toy up with her mouth.

“The next thing you want to do is get her in a punishment position. The position should be one that exposes herself to you and gives her a chance to reflect upon what she has done. You don’t come to her, she comes to you.” Master Thorne told me never to squat down to her level to punish her.

“What positions are my options?” I asked.

“You are three steps ahead of me. Stay in the moment with me,” Master Thorne said and then he told me to relax. “She isn’t going anywhere, and there is no rush. You will deliver the punishment in your own time. I am not saying all punishments have to be long, tedious affairs, although those have their relative merits. I believe that an offense should be dealt with as soon as it occurs while it is fresh in their minds. However, there are times I have something to do, and I need to apply discipline quickly. The key here is that you set that pace and not the slave,” Master Thorne asked me if I understood and I nodded. He warned me to speak up because while his advice was free this time, he wanted to be able to enjoy his day at the pool. “I have grandkids coming over here at 2 pm. If you don’t comprehend what I am teaching, then don’t you dare tell anyone that Master Thorne told you to do it this way,” he warned me.

He didn’t want to be blamed if I wasn’t going to listen to what he told me and learn things the right way.

I agreed, and he explained that punishments should never be given from anger. “You may be angry about what she has done. It may have embarrassed you. You may have just told her not to do what she did. You aren’t going to get anywhere with anger driving your actions though.

I quoted from Star Wars, “Fear is the path that leads to the dark side. Fear leads to anger. Anger leads to hate. Hate leads to suffering.”

“I never said you couldn’t cause some suffering,” Master Thorne had clearly never heard Master Yoda, or he didn’t care. “I just said don’t be driven in your decision to apply it by anger. I nodded my understanding and looked again at her butt.

“Now, before I can give you some options on what would be a pretty useful position to apply the punishment, can you tell me what body part you want to spank? You keep looking at her butt. Is that where you want to spank her?”

I honestly had no idea that there was any other body part I could pick.

I looked surprised. Master Thorne chuckled and told me that the butt is a tried-and-true option. “You won’t win any awards for creativity, but I can’t fault the old fashioned methods. They are old-fashioned because they worked in the past.

He told me that there were two easy options. The first was an OTK or “Over the Knee, spanking.” He said that this method works for all kinds of women but that it is most effective when the subject is smaller than the person applying the punishment. I was scrawny, and while Charity was by no means chubby, she was definitely full-figured and very well stacked.

Master Thorne’s second option was that I could have Charity assume the “V” position. “It is a core-command that is more commonly called “The punishment position because bend over and grab your ankles takes too long to say,” he chuckled.

I had another difficult decision to make. Until I was asked it seemed like a purely cosmetic decision to put the slave in a position to be spanked. Now, I realized there were important factors about leverage and body size and it made it difficult for me to decide.

I hate to admit it but I was turned on by the idea of putting Charity over my knee. I picked it despite Master Thorne’s warning that it worked best when the girl was smaller than the person giving her the punishment.

I expected Master Thorne to call me a pervert, but he sighed and said, “You act like a boy who has just been given three dollars to get a Banana Split, and you can’t decide on chocolate sprinkles or Spanish peanuts,” he observed.

He was right, though. After today, my Dad would probably forbid me from going to the pool with Charity without him, and this was perhaps my only chance to ever punish her. I know I was reluctant at first but now I felt if I stopped here it was a wasted opportunity to try it.

I had run the gamut of not knowing if I could or should punish her to a state of skeptical reluctance and finally to confident excitement about punishing Charity.

I felt like I understood some of the reasons people were attracted to BDSM and how it overlapped with leadership in the vanilla world. I know it sounds crazy, but my mind was abuzz with the possible ways I could apply some of what I learned to other aspects of my life. I was also excited to be able to spank a big butt, if truth be told.

I told him that I would go with the over the knee spanking. Master Thorne shrugged and didn’t judge me for making the choice.