Holiday Special - Rowan's Christmas Humiliation (Updated)

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Jeepman89
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Re: Holiday Special - Rowan's Christmas Humiliation

Post by Jeepman89 »

Can't wait.
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Re: Holiday Special - Rowan's Christmas Humiliation

Post by dsweenz71 »

Santa's Coming

I stood in my birthday suit in front of the three siblings. My dick, in a semi-state of arousal, pointed lazily past them at River the dog, who was looking at me with a ‘what the fuck’ expression.

“We want to watch you stroke your shit,” Piper repeated, and I looked at her shocked. “Do it, or I’ll send our new video to some of your friends at random.”

“No fucking way.” I decided to call her bluff. I could definitely take this kid. And when she unlocked her phone, I’d grab it from her and delete the video. I’d have to solve the iCloud issue, but maybe I could get a video of her and reverse the blackmail.

“Alexa,” Piper smiled, “Send the most recent video in my gallery to Seth Zinck.”

An automated voice came from somewhere unknown. “Alright, I sent your most recent video to Seth Zinck.”

“YOU FUCKING BITCH!” I screamed, unable to hold back. My best friend was receiving a video of me dancing naked and getting hard. How would I ever explain this?

“Maybe you should have done what we asked. You’re being very naughty, you know.”

“MAYBE I SHOULD JUST POUND YOUR FACE IN.”

Little Maxie started to cry, upset by all the yelling. “Now look what you did,” Kelsey scolded, rubbing her little brother on the back.

“It’s okay,” Piper warned. “I’ll send his video to his school’s head cheerleader next. That should teach him.”

“No!” I tried to protest defiantly, but it came out as a plea. “Don’t… please don’t?”

“Start stroking.”

“No… I…”

“Alexa, send-“

My hand never went to my dick so fast. I wrapped my fingers around it, massaging my stiffening cock as my pale white skin turned a hue of pink. I had four sets of eyes on me… five if you include the dog… and I felt a rising warmth that had nothing to do with the heat coming from the nearby floor vent. Maxie was still whining, but they’d changed to whimpers.

“Maxie, would it help you feel better if I give you a really important job?” Piper suggested.

The boy nodded, unaware of what he was agreeing to, with tears and snot running down his face.

I tried my best to ignore them and focus on my own task. I was fully hard now, speeding up my hand. My eyes closed as I tried to pretend I’m in my own home, in my own bed, thinking about Annabelle in her little blue crop top or Jasmine in that sexy miniskirt. My attention shifted suddenly to the girls at the gym, working on their glutes as I drooled behind them.

Announce when you’re about to squirt your cum,” Piper commands lewdly, and I open my eyes. She’s sitting on the floor with Maxie on her lap. Kelsey and Bree are on her right, and both are recording my masturbation session, one on a phone and one on her Ipad.

“Ahh!” I say, gesturing at the devices to Piper who just smiles.

“Don’t worry. You just keep doing what we say, and they’ll all stay in our own private collection.”

I closed my eyes again just wanting to get it all over and done with. I kept pumping, harder and faster, trying to picture the hottest girls at my school in situations that would never happen to them. Tied up in the school auditorium, stripping in the second floor science room, even fingered by the whole team during a basketball practice. I found myself closer and closer to the edge when two soft fingertips touched my nipples.

“You’re soooo naked right now, here in front of us,” Piper whispered, and I refused to open my eyes, to see her standing there, torturing me. “You aren’t wearing a single stitch of clothes in front of four of your neighbours. And they have videos of you, and all your contacts. They own you. They can make you do absolutely anything.”

At the last two words, I tumbled towards the cliff, yelling “I’m gonna cum!” All the images of sexy girls were gone from my mind when Piper had started talking, and I blushed deep as I realized that my humiliation was responsible for the ejaculation. As I felt a familiar warmth leave my body through my swollen dick, I opened my eyes to see little Maxie on his knees. He held a crystal glass to the end of my cock, catching rope after rope of cum as it spurted inside.

“Why are you catching it!?” I shouted. I had the sense not to move, as I don’t want to paint his face, starting a brand-new tantrum.

“Milk for Santy-Clause,” he said with a grin. “Piper says this kind is his favourite.”

I glanced over at the little witch, her face cracked into the widest smirk. “Santa will be drinking it all up too, but he’ll want more than that, so we’ll mix it with some regular milk too.” She took the cup from Maxie and set it on the table.

“Ew, you’re still messy.” Kelsey said, pointing at my dick.

“And I can smell you.” Bree began to gag. Faking it, I’m sure.

“That means it’s time for a bath!” Maxie squealed and Piper gave a nod, looking at me threateningly. Her glare told me, If you don’t do it, you know what will happen.

It was only a few minutes before a tub was run and I was being pushed in my several hands on my bare skin. This is ridiculous, I thought, but complied for fear of more friends seeing documented proof of my naked humiliation.

After I’ve sunk into the warm bath, Piper grabbed a face cloth and soap and rubbed them together. The facecloth was then scrubbed across my chest. She took extra time on each nipple and I couldn’t help but to feel my dick rise again. “Great. Just fucking great,” I thought as she turns her attention to my navel. Her hand continued downward so I reached out and grab her wrist.

“I can do that part myself,” I protested, not wanting this girl to stroke me in front of her siblings, especially with only a face cloth barrier between our skin.

“No, I’ll do it,” she simply smiled, trying to continue. I found myself incapable of releasing her hand though, and she started to get angry.

“Out of the tub this second!” She shouted. “Or I go send your videos to every single person you know.”

I scrambled out of the tub like a horse startled by gunshot. She commanded me over the side of the bathtub.

“You’ll learn to do as you’re told the first time,” Piper informed. “After a good and wet spanking from each of us, you’ll never disobey again. Either that, or you’ll be in this position a lot.”

The only ray of hope that appealed to me in that moment is that, since Piper wanted to record the scene, she would be last to spank me. I hoped my butt would have dried by then so her slaps wouldn’t be as hard.

Little Maxie started things off, and he giggled as his hand made contact. Thwack, thwach, thwack. He alternated, left cheek then right, squealing with delight as my ass turned pink.

Bree took her turn next, her spanks considerably more forceful. A series of involuntary gasps escaped my lips as she delivered them. My ass was red and hot by now.

Kelsey followed Bree, and thought to re-wet my ass with the face cloth. “Damnit,” I said out loud and she smiled.

“Didn’t think we’d let you go dry, did you?”

She delivered ten of her hardest in quick succession. SLAP-SLAP-SLAP-SLAP-SLAP-SLAP-SLAP-SLAP-SLAP-SLAP.

I was panting at this point, like River, their dog, but it wasn’t over yet.

“Here Kels’, hold the camera for me.”

Piper walked up and instructed me that I was to count off each spank, thank her, and ask her for another, pleading it to be even harder. “So, for example, you will say ‘One. Thank you. Can I please have another, but harder this time. Try it yourself.”

“One. Can I have another harder one?”

“Wrong! If you mess up, we start over, and we’re going until 10, so make sure you have it right.”

She had me practice a bit more until I was sure I had it. But it didn’t matter. Once she started slapping my ass, progressively harder each time, I messed up at the third.

“Oops, guess we start over,” she cackled.

Eventually I made it to ten, but my ass was on fire at this point. I climbed back in the tub, my dick back in a flaccid state, and cringed as my burning bottom touched the water.

The second time I was in the bath, I did nothing to prevent Piper from feeling up my cock. The damn thing was rigid and swaying by the time she was done with it, and it even gave the odd throb on its own as I got out of the bath and dried off. I suggested that I keep the towel, but the children were having none of it.

Bree looked out at the freshly fallen snow. The storm had changed to flurries now and was looking to stop completely soon enough. “It’s the perfect lightness for snow angels!” she yelled, and within sixty seconds flat, they had me back outside, laying in the snow and waving my bare arms and legs.

The ice cold snow provided much needed relief for my burning ass, but I chose not to tell them that. Unfortunately, they had me make another snow angel on my front. That one wasn’t so fun.

“Poor little baby,” Piper teased, as I trembled with coldness. “Let’s get you back inside and warmed up. We can put out some cookies for Santa before we get everyone to bed.”
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Jeepman89
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Re: Holiday Special - Rowan's Christmas Humiliation (Updated)

Post by Jeepman89 »

Nicely done. A very enjoyable chapter. Loved the bath and the spanking scene and of course the snow angels! What will they do to him next, I wonder. Santa's not the only one who's coming.
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Re: Holiday Special - Rowan's Christmas Humiliation

Post by lugro »

dsweenz71 wrote: Thu Dec 21, 2023 10:49 pm Santa's Coming

I closed my eyes again just wanting to get it all over and done with. I kept pumping, harder and faster, trying to picture the hottest girls at my school in situations that would never happen to them. Tied up in the school auditorium, stripping in the second floor science room, even fingered by the whole team during a basketball practice.
Yeah... None of this would ever happen to- oh, wait! :lol: :lol: :lol:
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Re: Holiday Special - Rowan's Christmas Humiliation (Updated)

Post by Trundle »

So happy to see a new chapter posted!

As always brilliantly written and although you don't need to have read Seth's High School Humiliation to enjoy this story it definitely helps pick up on little easter eggs and ironies.

Rowan panicking about Seth seeing him in an embarrassing position :D Don't worry Rowan, I think even if he did see this video he'll have more than enough of his own shame soon enough to cancel this out. Rowan having a fantasy whilst jerking off, of someone being fingered by the basketball team in the sports hall :lol: Don't worry Rowan that will happen!

Love how cruel the siblings are, especially Piper. Spanking was something I was actually waiting to see in the Seth story, maybe at this stage it won't happen with Seth, so it was great to see it happen here. Spanking is great in these stories as it's the perfect mix between physical pain, although nothing serious, and the shame of it happening. The shame is often much worse than the physical pain I think.

With Rowan already being made to jerk off I wonder what is next for the poor boy. Is it the final installment I wonder?

Love this, I like the idea of multiple stories in this universe. The women and girls in this neighbourhood seem very cruel :D
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Re: Holiday Special - Rowan's Christmas Humiliation

Post by switch87 »

dsweenz71 wrote: Thu Dec 21, 2023 10:49 pm Santa's Coming
My dick, in a semi-state of arousal, pointed lazily past them at River the dog, who was looking at me with a ‘what the fuck’ expression.
Absolutely love this sentence, for so many reasons lol. Comedy gold. :lol: :lol:

I am lazily imagining a universe where the evil Piper brings Rowan right to the edge of orgasm, then smears something sweet on his cock so that River jumps in and licks him to completion. All so that she can blackmail him with footage of him engaging in bestiality.

(OK, OK, it was just a joke. No need to look at me with all these 'what the fuck' expressions. :lol: :lol: )

Just my way of saying I'm waiting eagerly for the next part!
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