What a tease

Henry stood with both hands dangling procuriously close to his groin. One was placed on top of the other, as two hands were hardly required to hide his meager shame. Because the constant skin of his palm kept grazing his sensitive area he managed to, albeit reluctantly, maintain his ever present bounce of blood flow, forcing his tiny boner to persist despite everything being so incredibly humiliating.

Henry had spent the last several minutes considering his options. He was almost certain Madison wasn't playing a prank, specifically because she didn't look happy. He knew well the difference between Madison cracking an uncomfortable smirk and Madison genuinely cracking up because something funny happened.

In the past, whenever she tried to keep a straight face during a joke, Madison couldn't stay in character for long before busting out laughing and calling it quits. Usually, Henry could see that facade cracking a mile away. So, even when she wasn't done playing her joke of forcing a mock attitude, he would often be able to tell that she wasn't being one hundred percent genuine. She could try to be bitchy all she wants, he knows when she's forcing it. He knows when it's a prank.

Henry knew that if she came back and was upset, like really upset, then it was not a prank, and he would continue to beg her to forgive the misunderstanding and let him in. But, if she were messing around, even the slightest bit, then he would KNOW it was a prank, and until she broke character he'd just play along until she was done. In fact, if he played along to such a degree that it surprised her, that would likely get her to crack and burst out laughing, maybe even calling it off all the sooner. He figured thats especially true if she were just pushing things to see how far they'd go.

But no, despite all of that strategizing Henry still held out hope that his cute innocent stepsister, the one he used to goon over and work so hard to look cool in front of, surely she would not prank him...not his most precious and personal secret. He thought, Shes mean in a cute way, but shes not that mean....right?

A moment later he saw Madison through the large window entering the kitchen with her phone out and a stone cold look on her face. She had been almost smirking just a second ago, but she quickly decided to switch to mirthless as she entered the room with teasing intentions.

She figured Henry would be hiding his little dick, and she also knew the best way to enter the room would be to say the most humiliating thing for Henry to hear. So she said that.

"Eww. Henry stop touching yourself!!"

Instinctively, Henry's hands shot down to his sides and right there, through the clarity of the spotless and streakfree glass (which Henry had just diligently cleaned last week in preparation for his guest, because he is actually a mature and thoughtful young man), his tiny two-inch hopeful dick bobbed northward.

Not only had Henry's hands almost spectacularly revealed his entire open and nervous naked frame to Madison, but his consideration of her mood was also confirmed as she certainly didn't seem like she was joking at all. Thus, Henry almost instantly begged through the class.

"Madison, I wasn't touching.... Just come on, this isn't right. Just open the door already. This isn't how I was supposed to see you when you got here."

"Oh yeah, I bet! I didn't read your diary but I did just look around your place and its a fucking mess. Toys and books and dirty clothes are everywhere. You're a nasty little brat, Henry. "

She played off the lie about not reading his diary real cassual. She watched for his reaction and quickly realized he couldn't care less either way, since he preferred respond directly to her other accusations.

"That's not true, what clothes, you're exagerating! I'm not a brat, Madison, you are!!"

"Ok, tell me then, why are you even out there right now?"

Henry tried to think. Her question seemed genuine, and she seemed really mad. If this isn't a prank, what is the answer? He stood mute and thought hard, which just made him look more guilty to Madison by the second.

"I don't know, I was sleepwalking or something. Just open the door, this is SO not fair!"

Oh, don't try to tell me about fair, you little twerp. I think that what I'm about to do is incredibly fair based on what I just read. And everybody knows I'm the queen of dishing out fair punishments. So buckle up, little bitch.

Madison managed to keep all of those thoughts from flooding out of her mind by way of pursing her lips into the cutest tight sly smile.

Henry instantly felt a pit in his stomach at the sight of her smirk. Shit, she is enjoying this! This IS a prank. I'm going to have to change strategies! Fuck!

Madison, still being genuine, stepped right up to the glass, scrutinizing Henry's body with her eyes as she spoke with her half smirk and reasoned conclusion.

"You knew when I was coming. You were going to wait on the deck for me in your underwear, but you got excited and peed your pants. So at the last second you ran in here and tried to toss em in the trash- you missed by the way, loser- and then you ran back out there to just hide behind your hands, but you locked yourself out. Go on, tell me I'm wrong, I dare you."

Henry thought hard for the briefest of moments. He could see the phone screen in her hands and it was off. She didn't have her phone recording, and nobody else was there. She's clearly doing this just to mess with me. Maybe it's not even a big deal. Just play it cool. There's gotta be an end goal to this prank....maybe it's admitting to whatever she just said.

Henry completes his momentary weighing of options and sighs, resigning from begging and converting to appeasing.

"Yes Madison, you caught me."

Because of the way Henry sighed, and the way his obvious change in demeanor effected his overall stance and tone, Madison instantly felt as though she had achieved something. This wasn't a joke to her. This was Henry's game, and she had caught him. As far as she was concerned, Henry just admitted the truth. And that will just be the beginning, she thought.

"Say it again", she deamnded. "Say everything I just said, out loud to me."

Henry now felt she was clearly pranking him. This was a joke. She was merely embarrassing him and he had to roll with it.
He was just about to begrudgingly repeat the phrase when suddenly, he had a major brain fart! Wait a minute, she's definitely toying with me, but there's no camera on. This is just for her. Since she showed up she got me naked and has been keeping me that way. Oh my God, does Madison LIKE me?! Is that why she's prolonging this prank. Does she actually want to see me like this? Maybe my dick isn't as small as I thought. Maybe she's totally into me.

Henry was almost completely lost in a momentary delusion as his brain tried to cope with the sheer humiliation that was about to come with repeating those words. It was so silly, what she was suggesting he say, and yet here she was, smirking and looking him up and down. She orchestrated all of this, he thought. Maybe she likes me.

So with his blood flow still unknowingly half-dictating his thought process, along with this new odd sense of flirtation, Henry repeated her words softly, slowly, and with a slight lift of the eyebrows as he spoke in a (wanna-be) "sexier" tone.

"I knew exactly when you were coming. I was going to wait on the deck for you in my underwear, but I just got too excited and wet my pants. So I threw out my underwear and said 'to hell with it' and locked myself out here....for you to find me. ...and let me back in."

He said the last part with a bit of a forced smirk. He hadn't looked down at himself for several seconds and the sudden stupid thought that maybe she was into him had completely warped his perception of himself. For the briefest of moments he felt tall and bold.

Madison fought everything to not burst out laughing right then and there.
Oh my God, does this little shit not know when to the jig is up? Seriously, he's still horny and trying to flirt with me? The fuck, Henry. You have no game, and this certainly isn't how you play it. I bet he still thinks his plan might work. ...nope.

Madison's smirk returned as she swiftly double-tapped the side button of her phone, waking up the camera, and aimed the lense at the big full kitchen window.

*CLICK*

"Ok, here's the deal, baby dick", she said as all of Henry's bravado instantly disappeared, replaced almost immediately with signs of milti-level embaressment.

Shit, that was all a prank too?! Of course she's not 'into you', that'd be wierd!! Did she actually just say, baby dick? She still being a punk! Fine, whatever. What stupid little thing does she want me to do now, he thought.

This is going to be epic, she thought.