Holiday Special - Rowan's Christmas Humiliation (Updated)

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
dsweenz71
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Holiday Special - Rowan's Christmas Humiliation (Updated)

Post by dsweenz71 »

Rowan's Christmas Humiliation

The following story involves Rowan, the “best friend” character from another one of my stories: "Seth’s High School Humiliation". Although it is a spin-off of sorts, and would be considered 'canon' in Seth's universe, you do not need to have read SHSH prior to this story; in fact, this holiday-themed story occurs a few months prior to that story, so you would not even have to worry about spoilers of any kind.

This story will have three parts:

Frigid Exposure (scroll below)
Santa's Coming
A little Christmas Magic (aiming to post around December 25)

Image
Cover art created using AI.

Content warning: This story contains a teenaged boy humiliated by younger neighbours. Reader discretion is advised... move on if you don't want to read this type of content!
________________________________________________________________________________________________

Frigid Exposure

“Take that!” I shouted through my gaming headset. I’d gotten the final kill for my team, and a blue pop up on my computer screen indicated that I was “#1 Victory Royale!” Not bad, not bad. Especially for being out of practice. I hadn’t played much Fortnite in years, but this year’s winter break had just been so mindlessly dull that I didn’t know what else to do with myself.

It didn’t help that it had been snowing since the 22nd, and it was now just after six on Christmas Eve. We’d already broken local records for the most snow in a single snowfall, and it was supposed to continue overnight. Stupid climate change; What did it have against me!? It was seriously crashing any and all holiday plans I’d considered. I hadn’t been able to make it to the gym, the hockey rink, or even to Seth’s place as we’d planned before break began. Instead, I had no choice but to place stupid Facetime calls with my best friend. Hanging together in person is cool, but talking on the phone with the homies feels gay. It had been socially acceptable during the pandemic, of course, but in high school, trends can change fast. Now, it’s gay again. I don’t know why. I guess it’s an athlete thing.

I closed my computer and headed downstairs to grab an orange soda from the fridge. My mom was standing at the bottom of the stairs, looking out past the Christmas tree at the snow coming down. Her cell phone was perched between her shoulder and her ear as she rubbed the back of her head absent-mindedly.

“No, of course it’s not a problem. He’ll do it. Don’t even worry.” Somehow I knew she was talking about me. “And we’ll get there somehow. Rhonda hasn’t failed me yet.”

Now mom was referring to her car, Rhonda the Honda. Even I’ll admit, she’s a persistent little automobile, if nothing else. And she really is ‘nothing else’.

As mom hung up the phone, she looked over at me. “Our neighbor, Trisha… she’s just gone into labor. I have to give her a lift to the hospital. Her husband hasn’t been able to get back from his business trip because of the snow… and there’s no one else around.”

“Oh, mom… I don’t even think Rhonda can get through this mess of a storm.”

“The main roads are supposedly plowed, and she’s got no one else, Ro… We’ll have to make it work. She needs your help too.”

My ears perked up as I remembered her offering. “My help?” What could a woman in labor possibly need my help with?

“She’s got other kids.” She began counting on her hand. “There’s Piper, Bree, Kelsey and… oh, little Maxie. And their dog. You’ll have to go over and hang out.”

Mooooooom,” I tried, even though I knew I had nothing better going on. “I don’t want to babysit a bunch of little kids.”

She scoffed as she unplugged the tree and then checked that the stove was off. I easily recognized her ‘leaving-the-house tour’. “You’ll hardly be babysitting. Piper’s 13 and I’m sure she’s more than capable, but Trisha would prefer someone... more responsible around.”

I knew exactly what mom was doing. Boost my ego, and you’ll get more out of me. It’s like, my weakness. Can’t even control it most of the time.

“Plus, I know you always wanted to play Santa,” she was almost saying it in a sing-song voice, to make it more appealing. “You’ll get to put the presents under the tree later tonight.”

I smiled at that. I never had younger siblings. This could actually be a little fun, if the kids were cool. “There better be milk and cookies for Santa,” I said, as I pulled on my coat.




As I entered the neighbor’s home, there was a flurry of gratitude as Trisha thanked me about fifty times between shallow breaths, and her very pregnant (and about to be un-pregnant) belly was rushed toward the door by mom. As a playful border collie barked a few times and then sniffed around my crotch, Trisha hurriedly told me that the kids had already ate and that she’d scribbled a list of important things in a note left on top of the fridge. With a final fifty-first thank you, she closed the door and instructed that I lock it behind her, which I did.

I noticed the house was eerily quiet for having four children somewhere inside. I decided to walk around, find them, and introduce myself. I found two in the living room. The one watching Paw Patrol on the mounted flatscreen TV was definitely little Maxie, a boy of probably four with blonde hair, similar to mine. His whole hand was in his mouth (gross) as he was standing motionless, captivated by the TV. A girl who looked a little older (maybe nine) was sprawled out on the coach. One leg was way up on the highest cushion and the other draped off the side. She was wearing Spongebob jammies, and looked to be playing a game on an iPad.

I cleared my throat. “Hi, I’m Rowan,” I announced to the room. “I’m the babysitter.”

I don’t know what I expected. A little attention maybe? Excitement to meet someone new? Maxie was still transfixed, looking as if he hadn’t heard me at all. The girl on the coach simply said, “Kelsey.” She didn’t even look away from her game.

I left the living room, familiarizing myself with the rest of the house. Main floor: Living room, kitchen, dining room and bathroom. Two sets of stairs, one to the basement, and one to the second story. A front door and a back door.

Besides the original two kids, there was nobody else downstairs. I climbed up to the second floor. The first door concealed a room with a set of empty bunk beds, and the second door revealed what was definitely the parents’ room. I opened the third door, and a girl’s scream reverberated through the house.

“WHAT THE FUCK!?”

I’d accidentally opened the upstairs bathroom door and got an eyeful of a thirteen-year-old girl sitting on the toilet. “Why didn’t you lock the door!?” I shouted as I closed it again, just as frustrated as her.

“BECAUSE I DIDN’T EXPECT A FUCKING PERV TO OPEN THE DOOR OBVIOUSLY!”

I tried to bite my tongue. Sometimes, I say too much, and it can get me in trouble. All it would take is for one of these kids to tell on me, and for Trisha to then tell my mom. I didn't want to be punished, of course, but even worse, my mom would be disappointed in me. It's worse. Trust. If you know, you know.

“Are you okay, sissy?” The fourth and final child had quickly emerged from the last door on the landing. She looked to be about twelve years old, and an expression I could only guess was concern as she looked me up and down.

“I’m okay NOW,” her sister called back through the door.

The girl was still looking at me oddly. “I’m… uh, Rowan. Yeah, Rowan.” Why was I stuttering? Imbecile.

“I’m Bree…” the girl replied slowly. “And Piper’s the one you walked in on.”

“I didn’t actually walk in. I just… oh, whatever. I’m here to babysit.”

The washroom door opened, and a now fully clothed Piper entered the hall. She flicked on the light, I guess to get a better look at me. “We don’t need a babysitter.” She said coldly.

“Well… uh, your mom thinks you do.” I was trying to stand my ground. This girl was already getting under my skin though. I wondered how long it would take for Trisha to have her baby and get home.

“Just stay out of my way,” Piper demanded. “And knock before you open a washroom door.”

Piper stormed into her bedroom, slamming the door behind her. This left Bree and myself standing awkwardly in the hall, at least for a moment. Then, Bree shrugged, re-opening the door, and following her sister inside.

Well, that’s one brat I’ll be avoiding, I thought, heading back downstairs. I figured I might as well read the note Trisha left.

It was certainly scribbled by a person in labor, and she decided it was perfectly acceptable to write it in cursive, which is already hard for me to read, since they don't teach it in my district's curriculum anymore. I did my best to translate what I could.

Roan (she spelled it wrong),
Thanks for [a bunch of illegible words] last minute.
Kids are good. Let Riv (whatever that means?) out back [illegible words again]. Backyard has fence so no leash needed. Careful of lack of back door (looks like there's a back door to me. Poor woman in labor).
Bedtime no later than 9. Gifts in my closet. Put under tree when kiddos asleep.
Piper might want to help. (over my dead fucking body).
TYSM!!!!!!!!!!
- Trisha


What I could read was pretty straightforward, but obviously she’d been in a rush. No big deal. I looked around the kitchen and saw the dog laying by the back door, giving me a stanky side-eye. “You want to go out, I suppose?”

The dog lifted his head as if to say yes. The note had indicated that he didn’t need a leash, and that they had some sort of fence in the backyard, but there was also some stuff that was unreadable. I figured I might as well inspect the backyard, and make sure everything was locked up. The last thing I needed was to lose the family dog. I bet that little bitch Piper would just love to peg that one on me.

I threw on my boots and stepped outside. Since I was only going to be a minute, it wasn’t worth getting my jacket from the closet. The dog tried to follow me out, so I shut the door behind me. The snow was pretty deep just off the back deck, and it was fairly dark, a little after dinner time, so I reached for my phone to use the flashlight function. Shit, I didn’t have it. I must have set it on the counter when reading the note. I turned back to the house and reached for the doorknob.

I came to the realization pretty quickly that I had mistranslated part of the note. It hadn’t warned me of a lack of a back door. It must have said “Careful of lock on back door. This realization occurred because I was now standing on the back doorstep, locked out of the house.

I cursed my luck and tried to think through my options, but there was really only one. I knocked and waited. No response. I knocked louder. Nothing. What the hell? These dumb children. There’s four of them. Why were they leaving me stuck out here?

I walked around to the front of the house, grumpily, unlatching the gate that kept the backyard fenced in and pushing it open with a lot of strength; The snow had accumulated quite a bit, making it challenging to open. My feet also sank so deep in the unshovelled snow that it caused my boots to be completely covered, with snow tumbling into the top of both. I could feel the lower part of my grey sweatpants soaking through.

When I got to the front door, I skipped knocking completely, hammering the doorbell with my finger. “Come on you stupid punk kids,” I whispered under my breath, my teeth beginning to chatter slightly.

“Who’s there!?” Finally, a voice. Unfortunately, it was the last voice of the four that I’d wanted to hear.

“Piper, it’s me, Rowan. The backdoor locked on me. Let me in!”

“I’m glad you finally learned that it’s polite to knock,” she said back through the door. “But I don’t want to let you in! We don’t need a sitter! You live next door. Just go home!”

Oh, how I wish I could have. “I can’t! I don’t have my key, and I forgot my phone in the kitchen. Come on, I’m freezing out here!”

Piper went silent for a moment, but I could hear her talking with someone. “I heard from a friend of mine that you go to the gym a lot. Do you have muscles?” she called out.

“I… y-yeah, I h-have m-muscles, but they’re d-d-doing nothing for m-me out h-here.” I was shivering more now. I couldn’t even control it anymore. I should have taken the time to grab my jacket. Or, at the very least, my phone. I’d bet if I threatened to call Trisha, they’d open the door some fast. Unfortunately, I’d already let slip that my phone was in the kitchen, so the threat wouldn’t do butt all right now.

“We – that’s my siblings and I – want to see all your muscles. We have no need for a sitter, but if you entertain us, I suppose we could find a use for you! We’ll let you in just as soon as you strip off all of your clothes!”

“WHAT!?” I shouted, and my teeth suddenly ceased their chatter. It was probably the surge of red-hot anger that flowed through me at Mrs. young Satan in there, AKA Piper. What she was suggesting was completely ridiculous.

“I think you heard me loud and clear. Now make up your mind before we go back to what we were all doing.”

Under ordinary circumstances, there was absolutely no chance I would… or even could… strip for them. I don’t think I could physically bring myself to do it. Outside of sports showers, I hadn’t been seen naked since a stupid game of truth or dare at 13, and that was an experience I’d never want to relive. At the time, I was underdeveloped for my age, a fact which my friends Seth and Preston found hilarious when I took off my boxers and ran to the mailbox. Even the girls from the party were laughing at me, holding their thumb and pointer close together, with some even joking that their little brothers had bigger dicks. Since that single party, I hadn’t been in a single relationship. It was partly due to the reputation it caused me, and partly my own insecurities, I guess. My best friend Seth and I always joked I had negative rizz, but we both knew that single party had affected me a lot.

But this wasn’t normal circumstances. I was literally freezing. I didn’t have my phone, or a way into my house. The snow wasn’t supposed to be stopping anytime soon, and the temperature was only going to get colder as the night went on. Mom wouldn’t be back next door until God knows when. I had the grim realization that I would actually be dead by the time she got home.

“Last chance! What’s it gonna be?”

“F-f-f-f-ine.” I finally spit out, not wanting to delay further. I wanted to get back inside right away, so I began to pull off my clothes. “I’m d-d-d-d-doing it now.”

The shirt came off first, leaving me bare-chested, my nipples rock hard in the cold winter air. I had a firm chest, strong from many days at the gym. Those underdevelopment comments had actually been what inspired me to start going. I was proud of the progress I’d made over the past few years.

My stomach was firm too, although I was still working on defining my abs more. A sandy-blonde treasure trail led down under my waistband.

I pushed down my pants and underwear together, knowing there was no time to waste, but then I realized I wouldn’t be able to pull them over my boots. However, if I stepped out of my boots and socks, I realized I’d then have to put my bare feet on the cold snow. Not seeing a better option, I dropped my shirt to the ground and stepped on that, shielding at least a tiny bit of cold from my skin.

“I’m n-n-n-naked!” I shouted, hoping they’d open the door now.

“Put your hands on your head!”

Ugh. Demon child. “Okay!” I yelled back. “I d-d-d-did.”

I heard the lock click, and the door began to open, but only enough for a phone to pop outside. Suddenly there was a flash of a camera. “HEY!”

“Wanna see?” Piper teased, and the phone appeared briefly again. I squinted, thinking she was showing me the photo she’d taken, but instead I was greeted by my own lock screen suddenly unlocking. What the hell!? She just used my face ID on my own phone to unlock it. The door shut and locked once again.

“Wait! I did what you said!” I yelled. “P-p-p-p-please, it’s cold!”

“Just a minute!” Piper called back, laughing. I heard a scurry of action on the other side of the door but had no idea what they were doing. I didn’t like that she had full access to my phone right now, either. But there were more important issues at hand.

I tried to plead with her, but she’d gone somewhere, and I couldn’t get a reply. Finally, after another two or three minutes, the door opened a second time. “Pass in your clothes if you want to come in.”

“No! I… oh, f-f-fuck it. F-f-f-fine.”

I passed everything in, now standing directly on the cold snow. The door closed once again, but this time for only about thirty seconds. Then, it opened wide. Little Maxie was the only one standing in the doorway.

“Your thing is big,” he said, pulling a slobbery finger from his mouth, and pointing at my penis.

“No it’s not,” came a voice from the dining room table. It was Kelsey, still on the iPad. “It only looks big to you because you’re little.”

I looked down as I closed the door behind me. I was cold, and I noticed that my dick, which usually looked to be a decent size on top of my well-trimmed bush of pubic hair, had shrunken in the sub-zero temperatures. I felt embarrassed, so I cupped my dick and balls with my left hand.

“Nuh-uh,” said Piper from the stairs. “You’re here to entertain us. Not to cover up! That was the deal. Hands away.”

I wanted to tell her to go fuck herself, but there were two sets of very young ears nearby. “You just said to get naked, you didn’t say I couldn’t cover up.”

“I believe I just did,” she retorted. The friggin’ sass on this kid.

Whatever. If they want to see my junk, let them. Here’s your Christmas present, you little perverts. Take a good long look.

Knock knock knock. A sudden pounding sounded at the back door and I almost jumped out of my skin. I quickly dodged into the living room, out of sight of the door. Who the hell was here?

Despite my mini-heart attack, I was thankful to learn that it was Bree coming inside with the dog.

“River took a pee,” she said. River? What a stupid name for a dog. I bet Piper named him. “And his clothes are hidden really well.”

“That’s awesome,” Piper responded. “So is his phone.” She turned to me now, as I emerged back into the kitchen. “Did you hear that? You’ll only get your phone and clothes back if you give us exactly what we want for our holiday entertainment!”

I bit my tongue again. This was getting way too out of control. “Look, you can’t make me do anything. My mom is driving your mom to the hospital, and then she’s coming back. I’ll tell her everything, and you’ll all be in trouble!”

Bree looked over at Piper, a look of concern on her face, but Piper was undeterred. “I thought you’d threaten something like that, which is why I transferred your contact book over to my phone. I think if I sent the picture to your mom first, with you outside naked, she’d believe whatever story I cook up. You also had a lot of friends’ names in there… Annabelle, Collin, Jasmine, Preston, Sara, Seth, Vance… what if I sent that photo to all of them. You looked pretty cold and small in the picture. It’d make an amazing Christmas gift for some of them, I think.”

“Don’t,” I pleaded, defeated. “Please, don’t do that.” Somehow, in the matter of thirty minutes, this girl had gone from being an innocent neighbor that I knew almost nothing about, to a little blackmailing twerp with the upper hand. She essentially had my balls in her hands.

“Then entertain us; dance for us.” she smiled and looked over at Kelsey. “Hit it, DJ.”

Kelsey opened an app on her iPad and a song began to play. It was a bit of an older song, but I recognized it right away. Sexy and I know It, by LMFAO. We’d used it once at a pep rally with the basketball team and had even coordinated a little dance. Did Piper know that? Nah, she couldn’t. She was still in middle school for another few months. It had to be a coincidence.

I didn’t want to dance, but reluctantly, I complied. If you could call it a dance. I mostly just twisted my hips and bopped my butt to the music. Truth be told, I was simply scared shitless that this kid would send out the picture of me naked. Maybe she was bluffing, but it wasn’t a chance I was willing to take.

I’m embarrassed to say that it wasn’t just Sexy and I know It either. They had me dance to two more songs: Girls Just Wanna Have Fun, and All I Want for Christmas is You. By the end, I was covered in a sheen of sweat and blushing a rosy pink, but the kids didn’t seem to care. They were all smiles.

“It’s getting bigger!” Maxie squealed excitedly, pointing his slobbery mess at my dick.

He wasn’t lying. All the bouncing of my cock while I danced had stimulated the damn thing. I also realized that I hadn’t taken a leak in a couple hours, since before I’d been playing Fortnite. A growing need to urinate was helping the boner along.

“Oh my God,” Kelsey grinned. “How big will it get?”

“Not too big,” Piper teased, and looked directly at me, pinching her thumb and pointer together. Again, I flashed back to that traumatizing experience from when I was thirteen. This kid clearly evil. There was no other explanation. She had somehow figured out the perfect ways to get under my skin.

I just wish in retrospect that I would have noticed that Piper had propped her own phone up against the toaster and recorded not only my three dances, but also the rise of my dick at the end. She only informed me of the video’s existence after she’d confirmed that it had been fully uploaded to her iCloud gallery.

“Now I can be positive that you’ll grant our Christmas wishes. If you don’t, you’ll have a brand-new reputation at school. And first thing’s first.” She was looking straight at my cock. "We want to watch you take care of that thing.”
Last edited by dsweenz71 on Thu Dec 21, 2023 10:51 pm, edited 4 times in total.
TeenFan
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Re: Holiday Special - Rowan's Christmas Humiliation

Post by TeenFan »

A very cool...or should I say Cold start to this story.
I didn't see where Bree's age is mentioned (maybe I missed it)
Rowan is the same age as Seth, right...and this would make him 17 for this story? 16 at the youngest I suppose.
Nobody gets to the hospital and back quickly. Poor Rowan is going to be stuck there like a frozen popsicle for hours. I'm sure the girls
will think of many ways to keep him warmed up. I hope Maxie's observation is accurate about a Big Thing.
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Re: Holiday Special - Rowan's Christmas Humiliation

Post by dsweenz71 »

TeenFan wrote: Tue Dec 12, 2023 5:24 am I didn't see where Bree's age is mentioned (maybe I missed it)
I neglected to mention - she's just slightly younger than Piper, at 12. I'll edit to add in Rowan's best guess (which will be correct). And yes, he's in his senior year with Seth. :)
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Re: Holiday Special - Rowan's Christmas Humiliation

Post by imanewb »

Ah future 'nurses' in training.... maybe?
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Re: Holiday Special - Rowan's Christmas Humiliation

Post by Jeepman89 »

Amazing story! I love babysitting stories and this one is proving to be a great one so far. I also love that he doesn't have a micropenis which is a turnoff for me. Can't wait for the next installment.
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Re: Holiday Special - Rowan's Christmas Humiliation

Post by anthonydemon »

Nice Story! Wich AI you used for the image?
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Re: Holiday Special - Rowan's Christmas Humiliation

Post by Trundle »

Great to get another story in this universe and a christmassy one to boot!

Really great start, poor Rowan. SPH isn't usually my thing but it helps differentiate it from Seths story where he doesn't have that issue and with it only being a short story I'm fine with it. Piper seems sadistic enough to be the heir to Mrs Masters!

I liked Rowan calling talking via Zoom "gay". Obviously it's a silly thing and an offensive thing to say, to use gay as an insult, but I think Kids to this day still do say that so it felt very realistic to me.

Looking forward to Dec 2018 and the next installment.
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Re: Holiday Special - Rowan's Christmas Humiliation

Post by Jeepman89 »

Rowan doesn't have a small penis, I don't think. It was just cold outside and i think the girl was just teasing him. Hopefully, he has a nice sized dick once it warms up.
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Re: Holiday Special - Rowan's Christmas Humiliation

Post by dsweenz71 »

imanewb wrote: Tue Dec 12, 2023 5:34 am Ah future 'nurses' in training.... maybe?
Could be! Good thing for Seth and Rowan that they weren't a few years older and at their school.
Jeepman89 wrote: Tue Dec 12, 2023 5:59 pm I love babysitting stories and this one is proving to be a great one so far.
First one I'm attempting to write. If you can't tell by Seth's story, my fave is usually humiliation at school/around peers.
anthonydemon wrote: Tue Dec 12, 2023 7:24 pm Nice Story! Wich AI you used for the image?
I can tell you via PM if you'd like.
Trundle wrote: Wed Dec 13, 2023 12:41 am I liked Rowan calling talking via Zoom "gay". Obviously it's a silly thing and an offensive thing to say, to use gay as an insult, but I think Kids to this day still do say that so it felt very realistic to me.
I don't typically use slurs unless it feels necessary, but getting in Rowan's head, I couldn't imagine him not using a few. That's just how straight jocks usually are.
Jeepman89 wrote: Wed Dec 13, 2023 1:55 am Rowan doesn't have a small penis, I don't think. It was just cold outside and i think the girl was just teasing him. Hopefully, he has a nice sized dick once it warms up.
Correct. Rowan is average at worst, but I couldn't help but humiliate him about the size a little after he was out in the cold :lol:
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Re: Holiday Special - Rowan's Christmas Humiliation

Post by dsweenz71 »

Just a quick update that part 2 will be out within a few days. Earliest tonight. Latest Wednesday.

Life's gotten a bit busier lately! Thanks for your patience.
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