Mercy is for the weak

This one was quite tough.

Without a question it had to be public, it had to be extremely humiliating, but it couldn't lead to Ben getting arrested and I suppose It wouldn't do to completely ruin his reputation.

It was clear that this would require some prep time.

And so I left Ben alone for a while. Of course I took some precautions. I put roughly the same safeguards into place as Ben to prevent him from accessing the app. Naturally I ironed out his mistakes and also forbid him from mentioning the app in any shape or form to anyone but me.

Ben did appeal to me quite a few times, but I just ignored him. I'm sure he enjoyed dreading whats to come.

And so a week passed until all the necessary preparation where made. I called Ben in my room on a beautiful sunday morning.

“Good Morning, Ben” I smiled. “Did you sleep well?”

“Yes”, he sounded wary, I am sure he was aware what was coming.

“I am going to humiliate you now, Ben. I can say with confidence that today will be the most humiliating day in your life. The things I have planned for you, kinda scare me myself, but sometimes you just can't back down, you know? Before we start I just want you to know, that I love you Ben. And I will always love you. No matter the things that will happen to you today, please remember that. With that out of the way, are you ready?”

“No?”

“Good answer”, I grinned.

I had Ben getting dressed. (he was allowed to wear what he wanted) and made him wait outside.

I did take my sweet time. Anticipation is very important and I wanted Ben nice and worried.

Once I finally joined him outside I was pleased to notice that this was the case.

I took a moment to bask in my superiority before finally revealing what I had in store for him. “Alright. Walk around the neighborhood for 30 Minutes, while embarrassing yourself quite significantly.”

For a moment nothing happened. But then...nothing happened.

After a few seconds Ben started to look at me in confusion. “Why aren't I doing anything?”

Because that wasn't an order. I want you do to it out of your own free will.”

That didn't please Ben. “What the hell Sis, and what does “quite significantly” even mean?”

“That is for you to figure out and for me to enjoy, sweet Brother. Just let me warn you that If I should find your performance lacking, you will have the difficulty raised to “severely” And this time it will be with a command.”

Ben was contemplating it. I had a pretty good idea what he was thinking. “You will just have me go twice, anyway”, he deduced.

“Where would be the fun in that? But just to cover my bases, if you flat out refuse you get to do “quite significantly” and “severely” both via command.”

“Ugh...”

“See? No matter how you look at it, doing it from your own will is clearly more beneficial.”

“I need at least some time to prepare.”

“I'm feeling generous so I grant you that. You get five Minutes.”

Ben spend the majority of those five minutes pacing back and fort on the front porch His mind clearly racing.

No matter if its your own subconscious or not, ultimately you are still **** to obey a command. Your body moves on its own and ironically that gives you a bit of relief. Doing things out of your own free will. was without a doubt much worse. The easier course of action would be to just suck it up and let me command him. But Ben was way too stubborn for that. This was quite genius, If I do say so myself.

“Alright”, Ben finally decided. Took a deep breath and started undressing.

“This is fine, right?” he asked trembling when he was in nothing left but his underwear. “This is extremely embarrassing , you know.”

I mustered him briefly, my eyes lingering at his black boxershorts. “Well, to be honest I was hoping for something a little more creative...”

“Give me one more minute”, he declared and rushed back inside.

“Swapped your shorts I see.” Ben now stood before me in some baby blue boxers adorned with evil penguins. It was certainly a long time since I last saw them.

“Nice” I granted him a grin. “But why not go all the way and wear briefs tough?”

“Absolutely not!” Ben stammered extremely red. “Please Sis, this is really my limit, ok?”

Oh Sweetie, you have no idea what your limit is. “Get walking then, Penguin Prince. Oh and wear your shoes. Don't think you get out of this by faking an injury.”

“The Weather is really nice” I commented walking alongside Ben. I originally intended to keep my distance, depending on what crazy stunt Ben planned, but this was rather pleasant. “Must be nice feeling the breeze on your exposed skin like this.”

“Maybe I get skin cancer from exposure and die. That would be an improvement to this.”

“My, if you can still joke around like this, you can't be too embarrassed.”

“This is just me coping, ok? You can give me that much.”

“Hmhmhm...” I mused meaningfully.

The Streets where fairly empty, but not completely deserted. Ben did get the odd look every now and then, but the weather was indeed nice enough that it wasn't a completely unreasonable look.

That was until we turned a corner and came face to face with a cute girl.

At first the Girl had trouble processing whats in front of her, then she loudly gasped and widened her eyes. “B-Ben is that you?” Ben's reaction was equally flustered.

Now this is getting interesting. “A friend of yours?”

“Y-yes t-thats Marcie, a classmate.” Ben managed to stutter out.

I had to **** my grin back down. “Nice to meet you Marcie, i'm Rina, Ben's big sister.”

“N-nice to meet you” Marcie replied still taken aback. “Um...why are you dressed like that?”

“I forgot my clothes at home.” Ben answered.

“Huh?” we both replied.

“And I usually don't wear Undies like this. All my other pairs are in cleaning!”

“Ok...” Marcie looked like she wanted to flee any moment.

Is he doing this on purpose?

“And, and i'm i'm sorry but I need to go now. You know I really have to pee and i'm worried that I won't make it.”

“Alright, alright, I'm getting second hand embarrassment.” I put a hand on Ben's shoulder. “He just lost a bet against me.”

“I see.” Marcie smiled uncertain. “That must have been quite the bet.”

We said our goodbyes to Marcie and parted ways. I had to stifle my laughter, with very little success. “Oh Ben...that was amazing...i never thought you would pfft...”

“I thought I had to! And be quiet, she might still hear us!”

“That's a good thing. I am supposed to laugh in a situation like this.”

Ben looked out me, pouting. “That doesn't count, Sis. You can't just make things less embarrassing for me.”

That led to an uncontrollable burst of laughter. “My sides..my sides! Ben you are killing me! That was your plan all along, right? Murderer, Murderer!”

“This isn't funny!”

I desperately tried to reign myself in. “Y-yes don't worry Ben. What I did doesn't matter, you did very well.”

“So did I pass?”, he asked hopefully.

“What do you think Ben? Answer honestly.”

“I...don't think I did.” As soon as the words left his lips, there was an absolute look of shock on his face.

“Oh wow, really?” This produced another burst of giggles. “You are way crueler to yourself then I thought.”

“i..i..no...i didn't mean...” Ben looked absolutely defeated.

I smiled and tussled up his hair. “Guess what? Doesn't matter, you still passed.”

“R-really?”

“While it is awfully tempting to see what you could come up with. This looks like a case where I have to protect you from yourself.”

“Thanks, Sis...i really mean it. Thanks that you stop here.” He breathed a sigh of relief.

“Well....i wouldn't exactly put it that way.”

Ben looked at me puzzled. “You said I passed.”

“Oh Ben you are adorable. This was for Punishment 3. Pretty much just a warmup so I decided to go nice and easy on you. You don't think this took one week to prepare, right? Now comes the final one. Remember, you made me piss my pants for an entire week.”

Ben now seemed genuinely scared which pleased me to no end. “You aren't going to make me...”

“Hold that thought. Because whatever you might imagine, it will be worse, much worse.”

I leaned over Ben like a predator and spoke the words.

“Activate Program”