Chapter 10

When Berry was done with the homework test I’d given her, I picked it up to grade it. She passed this particular test with a score of exactly ninety percent. At first I thought she’d cheated. It took me fifteen minutes of poring slowly through the textbook, attempting to find the pre-printed answers. They simply weren’t there. After that I went online and found the matching teacher’s guide that DID have the answers.

Berry was cruising through school because she had to be there, NOT because she found it easy – she just remembered things taught without paying particular attention to what was sinking in. Once she began to apply herself to her own education she could be, if she chose, an ‘A’ student. When I looked at her in disbelief at her score, she grinned and poked her tongue out at me in fun.

Part of me decided at that point that she HAD to have cheated after all and that made it easier for me to put her through her paces with some advanced training while Cherry was set a new task of her own. I put Cherry in Casual Position because she didn’t need a writing surface then handed her my laptop. Since none of her family had attempted to drop in for a visit yet, it would be up to Cherry to put some of her training to use – she was to send emails to each family member, outlining her training and some of the reasons for it.

As with Berry, I made her multitask while she produced her emails. One of the items we’d brought home from the emporium was a ‘personal massager’ that plugged right into an outlet – so no batteries to replace. I had her sit on it while it was running. Sounds easy, right? I didn’t even make her use it directly on her pussy although I did ensure it was on a high setting. I didn’t want her to climax - I did want her to know it was running and vibrating against her butt plug and that sensitive little area between her cunt and asshole.

The purpose was to have her concentrate on what she was doing and ignore the distraction I’d supplied. I’d learned over the last days that sexual stimulation could be just as effective as a whipping in much the same way as a whipping could be sexually stimulating when done correctly. Cherry already knew to tell me if for some reason the stimulation was becoming too pleasurable. She’d agreed and for some reason that I still didn’t clearly understand, volunteered to a cool-down period if the stimulation became too intense.

When it had first happened, I thought Cherry was getting off on the denial-of-climax angle, sometimes called ‘edging’ I’d later learned. We’d talked and Cherry had tried to explain that the training wasn’t about having a man around to get her off – rather to ensure she didn’t get off and subvert the whole point.

Berry had to remove her butt plug and clean it with her mouth before her training. I inspected her carefully before we began and found I could already get two fingers easily into her ass now. I don’t think she was as pleased with that development as I was. Once she’d cleaned my fingers I checked out her pussy more fully. Unlike her mother, she was incapable of being fisted yet. Her cunt just didn’t dilate as much as her mom’s could.

“This is advanced training, Master?” Berry winced as I attempted to ease my pinky inside her.

“This is BASIC advanced training, yes, Strawberry.” I casually replied while she puffed out loud breaths at the discomfort I was causing. “If you are to be pleasing to others in all ways, your holes must be able to accommodate a fist for a woman’s amusement as much as a cock the size of Mule’s or that guy last night.

“But I’m really not gay, Master and Trix would never do that to me!” Berry objected.

“Not being a lesbian has no impact on what you may be required to subject yourself to, in the pursuit of other people’s amusement. It’s not about the sex, it’s about the submission,” I explained. My pinky finally penetrated her, allowing me to use my thumb against her clit more effectively.

“But sex isn’t supposed to huuuuuurt!” Berry wailed as I tried yet again to get my thumb into her.

“It’s not hurting me at all, Strawberry. I assume you’re selfishly thinking that any enjoyment I might get out of this training is less important than your comfort? Remember, you wanted this. Now show me how far out you can stretch your nipples,” I ordered.

Berry did a really good job of distending her own nipples. It had to hurt to do it yet she had a good grip and was doing a fine job of it. I guessed the pain in her tits was offsetting the pain in her pussy.

“Why am I causing you discomfort, Strawberry?” I asked, hoping to remind her WHY she was accepting this training in the first place. I wasn’t disappointed.

“Because I’m lazy, stubborn, hurtful, obnoxious and a bunch of other things, Master,” Berry admitted. Surprisingly she seemed calmer once she began to think about why she was getting her pussy stretched.

“Don’t forget that you’re a lying, manipulative schemer too, Strawberry,” I said, pulling my fingers out and slapping her opened cunt. Cherry looked over at her when I did that, probably identifying with Berry’s predicament. I regularly beat Cherry’s pussy although I’d taken to using a spatula on her cunt whereas I was only using my hand on Berry’s at this point.

Another thing I planned to do was call her Strawberry when she was immersed in the advanced training. Either name was correct, however I thought it prudent to remind her that being called the more casual sounding, ‘Berry’ was a privilege and not her ‘official’ name. It’s a small thing and I’m sure some would think it pedantic of me to distinguish the difference however I could hardly call her fuck toy or cum dump or something like that when she isn’t either one ... yet.

I left Berry briefly to check on Cherry at this point, telling Berry her nipples weren’t elongated enough. “All proper sluts have long nipples. Since you’ve never had a baby suck milk from them, we’ll have to stretch them the old fashioned way. If you tug on them long enough, they’ll stretch,” I assured Berry, having no idea if that was true yet hoping it really was. It certainly looked wonderful watching her make the attempt. I made a mental note to begin using breast pumps.

I looked over Cherry’s shoulder at the emails she was currently writing. This one was to her brother, Donny. Her spelling was atrocious and her grammar was even worse. I wondered what grade she left school at. That television show, ‘Are you Smarter than a Fifth Grader?’ proved that her education was probably equivalent to a fifth or sixth grader’s.

“Damn, Cherry. This is absolute crap. No one sends an email like that unless they never want to lay eyes on the recipient ever again. You just listed some of the shit you’ve done to him. Sure, make him angry all over again and never want to see you as long as he lives. It’s not as if he is winning the lottery to come over here and see you strutting around the apartment naked. You make it sound like he’d be winning the grand prize, seeing his own sister nude. You are NOT a prize. You’ve been a royal cunt to him in the past. This is supposed to be an APOLOGY for that, not a Publishers Clearing House advertisement!”

“I wasn’t to that part yet, Master,” Cherry whined before I cut her off.

“Make sure you’re spelling out that you want to make things right and invite him to get even if he wants. If you want to list things you’re sorry for you can and you should. ONLY after you make it clear that he can be assured you’re going to be punished for every single violation of his trust, attempted destruction of his pride and assurance that you’re serious. AND after you invite him to witness your penitence in person.”

“You wouldn’t really do that though, would you Master?” Cherry asked nervously.

I picked up the crop off the table and swung it at the fleshy part of her ass not being sat on right at that moment to highlight my instructions. “You. Will. Show. That. You’re. Truly. Sorry. In. Person. And. You. Will. Make. A. Point. Of. Inviting. Him. To. Watch. So. He. Knows. You’re. Serious.” Each word was highlighted with another swat. When I’d originally told her she’d have to do that, she must have thought I’d been joking.

This was to be where the rubber hit the road as it were. Training is one thing. Training with an audience of a family member you’ve wronged would leave a more lasting impression. Doing penance naked in front of that family member would be a lesson she’d not quickly forget. I smacked her other ass cheek about the same number of times while reminding her that the red, squiggly lines under her misspelt text meant that she had an opportunity to correct what she’d written as she was writing it.

I reached down and cancelled the page of text she’d already painstakingly written. “Start again. You can’t really be that stupid! I don’t want to see spelling mistakes and misused words on your next attempt. No one comes ‘too’ a house. That roughly translates to them bringing a house with them as well when they come.” I rapped my knuckles on the top of her head as if I was awakening her brain. “And spread those huge fat old ass cheeks of yours. Maybe the problem here is that you’re not feeling the butt plug or vibe enough? Concentrate more on what a pain in the ass you are and maybe feeling more pain in your ass will help. Jeez. What a dumb cunt!” I exclaimed for good measure as I faked disbelief, shaking my head in disgust as I moved back to Berry.

I resisted the urge to look further at Cherry in order to gauge her reaction to my harsh words and actions. I hoped both had had the desired effect however I didn’t want her thinking I was interested enough in her to give her any more of my valuable attention. It was, I noted, nearly half a minute before I heard the keys clacking again.

I went back to plunging my fingers into Berry’s pussy while I had her bounce her tits, continuing to hold her own nipples. She nearly let them go in surprise when my thumb penetrated her asshole this time.

“As you can see, this maneuver can be used to control a bitch when the opportunity arises,” I explained, pinching my thumb against my second and index fingers through the membrane that separated her cunt from her ass.

With just these three fingers, I was able to lift her butt off the floor. Her hands automatically dropped to balance herself even though I wasn’t about to lose control of her body. I could easily imagine Berry hadn’t intended to drop her hands however the idea was that she would do ONLY what she was ordered to do while in advanced training. I really had no choice other than to correct her for her lapse in judgement.

With my fingers in her pussy and thumb in her ass, I got to my feet, pulling Berry to hers as well.

“I’m sorry, Master,” Berry pouted, hoping to beguile me with her favorite expression into going easier on her for her mistake.

Berry stood naked facing me, her body almost touching my clothing, my fingers remaining inside her, keeping her in place. Her head was only at chest level so she had to look up sharply to look at me. I’d always stressed the importance of keeping eye contact while in training, unlike the stories I’d read online that had the submissive always looking down.

“I’m sure you probably are sorry, Strawberry. Are you sorry for the things you said at Taco Bell yesterday or the emporium, or the truck stop, or even this morning? Maybe you’re only sorry for getting caught trying to influence me just now, or maybe you’re sorry you dropped your hands,”I said while using my free hand to smack her bottom rhythmically.

“I’m sorry for all that, Master,”Berry winced as a slap hit her ass in exactly the same spot two times in a row.

To her credit however, she never lost eye contact and she didn’t cry out in pain. I could see her getting close to tears though. That’s what I wanted to see. True sorrow that she’d done something and earned this response when she could have avoided it if she’d made different choices.

“When you go to school tomorrow,” I began, still holding her close and spanking her ass, “Trix is going to be in charge of you. I don’t doubt for a minute you’re going to test her authority. When she humiliates you in front of others for some of the things you’ve done to her in the past, are you going to be able to take it or will she be reporting a failure to control you?” I asked. I then stopped spanking her so she could properly consider her reply.

“I don’t know, Master. If she told me to do something demeaning right now, I’d do it in a heartbeat, but that’s probably because that’s how I feel right at this minute. By tomorrow, I’ll probably feel like my regular self again,” she admitted sadly.

I wondered if she was sad because she knew she’d feel differently in the morning or because she thought Trix was too much of a pushover to dominate her.

“Would you prefer to find out in the morning or would you rather go to school feeling like you do right now?” I asked, resuming the spanking. I really only wanted the extended spanking to let her know she was not in control of anything at this moment in her life. I could feel the heat of her ass on my hand. And her pussy was lubricating heavily to the point where my fingers were already quite sticky.

“Do I have to answer, Master?” Berry asked, looking down. Maybe her neck was getting tired from looking up so sharply, or maybe she didn’t want me to see what was in her eyes.

“Of course you do, Strawberry. And you need to look at me too,” I insisted, giving her a couple of harder spanks to make sure she understood.

“I really want to be a good person but I’m just not,” she admitted, trying to convince me with her eyes.

“Then in the morning, I’ll make the effort to give you a little more advanced training before school too, okay?” I asked, feeling like it was a totally surreal situation where I was reluctantly agreeing to discipline the teen for no specific reason and that was a gift to her.

“Thank you, Master,” Berry said. I totally believed at that moment she really did mean it.

Her head dropped down again and I know she noticed the bulge in my pants. I hadn’t even realized that in the last few moments, I’d stopped spanking her again and was now just resting my palm on a wonderfully warm, red ass cheek. My fingers were still in her pussy and my thumb still in her ass. I was uncomfortably hard. Part of me felt bad that I was aroused. I was supposed to be, ‘working’ not horny.

“Sir ... um ... may I um, like practice again what we did before?” Berry asked, her cheeks reddening probably as much as her ass cheeks surely were.

“Full sentences, Strawberry,”I said quietly, squeezing the cheek I was cupping.

“I feel like I want to, um, you know ... not for me or anything. But, um ... could I like practice using my mouth on your dick again?” She finally managed, then hurriedly went on with, “I know you’re hard and mom’s busy and everything. I just want to do something nice for a change.”

I couldn’t help it. I looked at her as if she’d grown a second head. This was not the smart-mouthed, trash talking teen who had a sarcastic remark and joke for every occasion. She saw the look and wilted.

“Never mind, Master. I’m sorry for asking.”

Cherry spoke from her place almost behind me since I’d stood Berry up. She didn’t sound angry. In fact she sounded somewhat happy that her daughter had asked to do something nice for another person. “You’re feeling it, aren’t you, Berry?”

“It’s just like the first night,” Berry replied cryptically.

Berry and Cherry seemed to be able to communicate volumes to each other with only a few words spoken, as I’ve said before. This time I felt more looped in. Cherry was asking if her daughter was feeling the effects of the training that had temporarily changed them for a few days after my presentation.

“Berry, you have five minutes. It’s okay if you don’t make me cum however I want you to spend those minutes practicing giving yourself chin nuts like your mother taught you. If you want to make it a challenge, that’s okay too. I’ll give you a treat if I do cum, okay?”

Berry smiled. One of those rare, real smiles. I was asking her to deep throat me and offering a treat for making me cum. This was a first for me - or maybe not a first - yet still new. I was ALLOWING a female to suck my dick instead of chasing one who I hoped would eventually do so. I’d learned a lot from these girls.