My New Punishment Part 2

My New Punishment Part 2
By Nocti Raven
[email protected]

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This story is intended for ADULTS ONLY. It contains explicit depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.

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Constructive criticism is welcome.

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My New Punishment Part 2

My whole life changed that fateful day, when my pompous classmate Ryan and my little sister Jessica were declared my personal disciplinarians. Ryan was 14 like me, and Jess was almost 13. They were empowered to decide, as my parents once had, when I had done something wrong, and I was obligated to submit to whatever punishment they decided on. And, of course, there were really only two: a drawn-out, agonizing spanking to my bare butt, and an excruciating squeeze to my balls.

For about a week after that, everything was more or less calm. Ryan came over for dinner twice, which I realized was normal now that he and Jessica were dating. I was always on my best behaviour after the initial shakeup, and more than a little jumpy whenever Jess and I were in the same room, but having Ryan in the house was a new level of discomfort. I barely spoke a word when he was over, except when he asked me if I'd been good lately and I replied "yes, sir," which is how he'd privately suggested I address him. At school the only class we shared was English, and I managed to avoid him well enough there, but at home he was unavoidable. At least my conversation wasn't missed at the dinner table, because Ryan chatted up both my parents like a regular adult.

Unfortunately, living in awkward terror couldn't be the worst of it for very long. One Friday night, after precisely one week as my disciplinarians, they got a chance to use their power again. Mom and Dad were going away for the weekend, and they decided that, even at my 14 years, I was too badly behaved to be trusted alone at home, so supervision was arranged. Ryan would stay over for the weekend, helping Jessica babysit me. Not that she needed any help, of course. She just enjoyed his company and thought that I might as well.

One of my first acts after Ryan and I arrived (we walked home from school together) was to express my opinion that I really didn't need a babysitter, and the he and Jess might as well just ignore me and do their own thing for the whole weekend. As disturbed as I was by the idea of Ryan and my sister together, it was nothing compared to how violated I felt just standing in his presence, knowing that every time he looked at me he was seeing me naked again, red-assed like a little boy, and with my balls in his hand-I shuddered at the very thought.

Ryan looked me right in the eye then, and told me I was in the wrong. For me to advise him on what to do this weekend, I had stepped out of place. I did not know better than him. He would tell me what to do, not the other way around.

After making sure my shoes were off, he steered me into the living room where my punishment would take place. Jessica, whose school ended half an hour before ours, was already home, and she came running downstairs at the sound of the door opening to greet her boyfriend. After their quick hello kiss made me cringe with embarrassment, she noticed me standing in the middle of the living room and immediately figured out what was going on. Ryan explained what I'd done wrong, and Jess thoroughly agreed. She added that by insisting that I was mature enough to stay home unsupervised, I was technically attempting to break the rules.

The happy couple sat together on the sofa and ordered me to strip naked. Jessica had already seen me bare dozens of times, and Ryan had twice, but that didn't make it any easier. The fact that I was now stripping on their authority rather than Mom's made me feel even more naked before them if that makes any sense. Knowing they had this power, to order me naked, it made clothing seem nonexistent. It made me feel so completely powerless. Just as I had always feared, Ryan was my master in my own house. And Jessica, my younger sister, was my mistress.

And then there was the embarrassment of just standing there like that, all on display, without even my hands to cover my shameful nudity. I knew that even if I tried to cover myself, they'd probably say "hands at your sides." And if not, Jess would giggle, laughing at the futility of my gesture, of hiding something they'd both seen already and laughed at already.

Seeing those two together, eying my equipment so critically . . . it made me wonder how just how much they'd done together. Now Jessica was looking at my air conditioning-shrunken little stub of a penis with that same smug superiority as Ryan. I cringed as I faced that realization head-on for the first time. Ryan was bigger than me in more ways than just his muscles. And Jess knew it.

Before the spanking began, Jess made me approach the sofa, face away from them, spread my legs, and bend over. She tapped my balls just hard enough to make me cringe, then began bobbing them up and down. She wondered aloud whether this offense warranted a squeeze in addition to the spanking. Ryan gave her a loud kiss on the cheek and told her that I would be punished in whatever way pleased her. It would almost have been cutely romantic if anyone but Ryan had said it. And if they hadn't been talking about squeezing my balls.

She thought about for a moment, and I almost cried right there for how trapped I felt. Trapped between accepting my fate, my punishment, and whatever worse torture they'd surely think up if I tried to run.

In the end Jess decided that I could get out of this with just a red butt. But even that couldn't bring me to rejoice because she hinted that the reason for her decision was that my balls would inevitably feel some punishment in the coming weekend, and there was no reason to rush into things.

While they talked I could feel one of Ryan's big hands patting down my right buttcheek, like some clichéd evil genius caressing his cat. When Jess mentioned the inevitability of a ball squeeze, I let out a strangled little whimper involuntarily, at which point Ryan took full advantage of my position and tickled the area of my asshole a little, just enough to shock me into bending my knees and stumbling forward.

The gruesome twosome laughed together as I extricated myself from an awkward position on the floor. I flipped over, essentially spread eagle. There was no escaping my constant humiliation.

They decided that Mom's old diaper position spankings had gotten-well, old. Instead they went for a tried and true position which I hadn't felt in many years: over the knee. Since the two were seated together on that couch, I was told to lie over both their knees. Since Ryan had reported that offense, he would be the one actually spanking me, so I was told to lie with my butt directly in his lap. That meant that my dick, small as it was, dangling between his legs, would enjoy the weird friction of his denim jeans closing around it. Jessica's miniskirt-bared legs were pushing up into my stomach.

Ryan reached underneath me to retrieve the new replacement for Jessica's hairbrush as my spanking implement: his belt. I realized how serious this was when I felt Jess's hands on me holding me down-one on the back of my neck and the other on the small of my back. I winced and clenched my butt, praying that tensing myself into readiness would make it all just a little bit easier.

The first blow seemed to knock the wind out of me. My tenseness fell apart as the searing pain of that flexible black leather bit into me. I tried to arch my back in protest, but my sister's hand held me down.

I managed to rear up with agony despite her for the second spank, and I cried out, finding my voice. Jess just put a hand right on the back of my head and pushed me down. She said that if I couldn't sit still and stop screaming, the spanking would go twice as long.

For the third slap, I was cooperative, but sobbing. Despite being 14 and having the pretty good vocabulary that came with the lifestyle of a bookworm, I remember thinking only the word 'bad' over and over again. The belt was bad. It was so mean and sadistic and painful and hurtful and evil that the simple blunt negativity of bad was the only adequate description. Through the whole spanking I just kept thinking, this is really bad.

I don't know how many lashes I got overall. There was a point where Ryan started to go faster and I lost count. That always happened. Even with mom's old spankings, there would always come a point at which I stopped being aware of how much I'd taken. It just became pain. My whole mind was consumed by wishing it would stop. And with Ryan, I felt like I was just crying because I hated that he could make me feel that way.

When it was over, they left me lying across their laps for a few minutes just sobbing. I calmed down after awhile, and wondered whether I was expected to get off. When I managed to stop crying, I heard a noise that chilled me to the bone despite the searing hot pain in my butt.

Jess and Ryan were kissing again, French kissing, sucking and slobbering at each other's tongues and lips. I was 14. I had fantasized about kissing a girl for years, but I felt like a third-grader again, 8 years old and repulsed by the very idea of kissing a girl. Those two going at it . . . the idea was just so disgusting that I felt I had to get away. I pushed down on the couch, pushing myself up and rolling off their laps and onto the floor.

I landed on my butt, which chafed horribly as I struggled to my feet.

Jess and Ryan managed to pull away from each other to laugh at my obviously hilarious antics. As I headed for the door, head hung and butt clenched, Jess called me back. She told me to take the pile of my discarded clothing upstairs and drop it in the laundry hamper, but she was very clear that I was not to put any more clothing on. I was to remain completely naked for the rest of the weekend.

I meekly obeyed and carried my clothes upstairs with me. Just like on the nights of my first two spankings with Ryan, I lay face-down on my bed and soaked the pillow with tears. But it wasn't night time yet. I was still hungry for my after-school snack, and still expected to play video games in the basement rec room, and still planned to end this Friday night like most others, masturbating to what little hard-copy porn I had acquired because my mom monitored my internet usage.

But none of that was possible. I couldn't get to the kitchen or the basement without walking past the living room, and if those two were still in there . . . I couldn't stand the thought of seeing them again. I couldn't bear to imagine how they'd respond if I told them what I was doing. A spanking, perhaps, because I would go for junk food. Or maybe a ball squeeze for wasting my time on games.

Or maybe they wouldn't notice me passing by because they were . . . I refused to let that mental image form in my mind. But now I knew that every time I thought of sex, I would immediately think of them, and that ruled out jacking off . . . maybe forever.

And then I thought of how pathetic I must be, just for having to jack off. Ryan wasn't the only guy in our year who'd found alternatives. I must have heard at least a dozen stories at school about summer camp adventures and "sweet 14" parties gone terribly right, and even girlfriends who embodied every boy's dreams. But I had no stories. No camp, no party, no girlfriend. Not even the confidence to approach a girl. Especially now.

A few hours later (at least I think it was) I was snapped out of my thoughts by the excruciating crack of Ryan's whip-like belt on my still naked butt.

I cried out, and Ryan just snickered. He placed a hand on my butt once again, kneading my cheek like dough, aggravating that horrible sting with every finger. I twisted with the pain, holding in a million objections. Ryan calmly told me that he and Jess had ordered a pizza for dinner, and invited me to join them. He said I needed to eat to get a little meat on my scrawny bones.

We ate at the dinner table, not like three kids having a sleepover but like a proper grown-up family. I was a little surprised that they actually let me eat, 'cause being sent to bed without dinner was just the kind of classic demeaning punishment I'd come to expect. Seeing my surprise, Jessica laughed.

"Oh Jake," she said. "What kind of babysitters would we be if we didn't feed you?"

Ryan laughed. I just ate, silently asking why I was entitled to food but not clothing.

Almost seeming to read my mind, Jessica chose that moment to inform me that she and Ryan had made a new house rule. In order to make punishment more convenient for Ryan, I was instructed to be naked whenever he and I were in the house. If he ever caught me in so much as a sock under this roof, I'd feel it in my butt.

I shifted in my chair, for the last feeling in my butt was still quite touchy.

Not surprisingly, I lost my appetite halfway through the meal. Some combination of my nudity, the way those two were eying each other, and the searing pain in my backside left me unwilling to eat.

I nervously asked permission to leave the table. I regretted it almost immediately.

Jessica called me ungrateful, and Ryan made some clichéd quip about starving children in Africa, then another about how a scrawny wimp like me needed nutrition. I instantly apologized and promised to finish everything before me, which seemed to calm them down for the moment, but they remained eerily stern-faced as they watched me consume every mouthful. I never thought I'd find pizza so unpleasant, but by my last slice, it was disgusting.

It felt like I was five years old again, a pouty kid who fussed over meals and got scolded for it.

After dinner I was led back to the living room. I couldn't feel the food in my stomach anymore. Just the butterflies that came with knowing I'd failed to make amends for my "ungratefulness" by finishing the pizza. More was to come. As terrified as I was that this would be the impending ball squeeze, I was even more afraid of another spanking on top of the lingering earlier one. I don't think I'd ever been spanked twice in one day before.

When we entered the living room, they sat on the couch again, though this time with a little more space between them. Oddly, I was instructed to kneel. I didn't get why at first, but I realized they probably enjoyed that arrangement. They were like the king and queen sharing their great throne, and I was the pitiful peasant, to poor to afford clothes, kneeling properly before them.

That was what I thought anyway. Then Ryan explained what was about to happen. Since I hadn't cared for the dinner so thoughtfully provided for me, I would be treated to an extra special desert. Ryan spread his legs a little and told me to crawl forward. When I was kneeling right between his knees, with my bare front practically touching the sofa, Ryan unzipped his jeans and pulled down the front of his boxers.

I flinched as his dick popped out from behind the plaid fabric, then I stared at it for a second, weirdly transfixed. As I had known and feared, he was undoubtedly bigger than me. He was still pretty floppy, but already as big as my stiffest erection. In my mind I had imagined it being scary big, like porn star big, but this was somehow worse. This was realistically better than me. Believably better. It wasn't superman's dick, but it was a man's dick. Suddenly mine felt smaller than ever. I could practically feel it contracting to a little button at my crotch.

Ryan told me what to do. He told me it was simple. The only thing I had to be careful about was my teeth. If he felt teeth on his dick, I'd feel fingers around my balls.

He was hard by the time he'd finished saying that. It was pointing up a little, but he shifted his butt higher on the couch and levelled it straight between my eyes. I winced. I didn't know what to do. I was overwhelmed with how wrong this was. I had dreamed of my first blow job, jerked off to the thought of it dozens of times. I had built up the fantasy a thousand different ways, with a thousand different people. But the one thing that every scenario had in common was that someone else was sucking my dick, not the other way around. I was not supposed to be on this end of my first blow job.

Seeing my obvious stalling, Jessica cordially suggested that I start with a kiss.

I silently thanked her for ruining my first kiss too. But I knew I couldn't delay any longer without risking more harsh punishment. I closed my eyes, licked my lips, and gave the head of Ryan's big, manly penis a big wet kiss. I held it there, and he tensed up, pushing it in past my lips. He must have inched forward on the couch because my lips were around his shaft before I knew it.

"Come on," he said. "Up and down."

It was a bit tricky to hold my teeth apart while my lips caressed his clammy skin, but I did what he said. I winced hard, crumpled my eyebrows together in frustration, and let an involuntary whimper escape from the back of my throat, and then I leaned forward and took the rest in. It went in pretty deep, almost enough to make me gag, but thankfully not quite. I was a little surprised when I made to the base and felt his pubes tickling the tip of my nose. He had a thick, curly bush, the same dirty blond as his hair. That put me to shame as well. My hair was darker than Ryan's, but my pubes were still sparse and downy. But they already knew that. They had already laughed about it.

And the taste . . . I did not like the taste of Ryan at all. His flesh tasted the way my hand smelled after touching myself for a while, like dick sweat. It reminded me of the boys' locker room at the school gym. And like most scrawny geeks, I hated gym.

I went back and forth a few times, and Ryan seemed to like it, arching his back and sighing and all that. But I think I was going too slow for him. Soon he grabbed onto my head with his hand and started guiding me through the motion. It was getting harder to keep my teeth apart. I groaned with the slowly growing ache in my jaw, but Ryan wasn't listening. He was just enjoying himself, and I assume Jess was too.

After a minute he inexplicably pushed me away, leaving a telltale string of saliva still hanging between my wet lip and his wet dick. I panted with relief from the strain on my mouth, so delusionally happy to be free that I managed to convince myself it was over, even though my knowledge of male anatomy told me that fat lady hadn't sung yet. Ryan stood up, knocking me back from my knees onto my butt. His pants and boxers slid down to just above his knees. He walked over me so I was between him and the sofa, then he spun around and told me to do the same. I was a little confused but Jessica reached over and steered me around by the shoulders. I ended up sitting on the floor with my back against the sofa.

Ryan walked over, his throbbing, slick member now level with my face again. But this time he didn't want me to do any work. He put a hand on my forehead, like he was holding me in place, and rammed his way into my mouth. He went on faster than before, and he added the bizarre new sensation of his pendulous balls tapping against my chin with every thrust. I wasn't even sure if it was technically a blow job anymore, or if he was just fucking me in the face. Again my jaw began to protest and I was emitting as much sound as I could under the circumstances, but there was no stopping him.

Until he stopped, that is. He just stopped, half in my mouth and half out of it.

"Suck," he commanded.

I began to apply as much stimulation as I could without rocking my head back and forth and then – and then he came, right as my lips were just around the head. He squirted at least four strong bursts of warm goo into my mouth before they started to die down. It didn't shoot down my throat as I'd feared, but it seemed to coat the roof of my mouth, and quite a lot dripped down onto my tongue.

He told me to tighten my lips as he slid himself out. Then Jessica reached around and placed her hand across my mouth, sealing it. She told me to swallow, or she'd pinch my nose. Ironically that taste was slightly less alarming than the taste of dick itself. For some reason Ryan's semen actually tasted better than mine smelled.

Ryan pulled up his pants and closed his fly, then sat down on the sofa next to Jess, panting lightly. They exchanged a sickeningly lovey dovey smile. Then Ryan looked at me and asked Jess to give me a squeeze. I turned around to protest, but Ryan said he'd felt my tooth brush against his dick near the end, when he was going really fast. Jess obligingly reached down over my shoulder and right to my crotch. I was powerless to push her hand away, even though I'm sure I was stronger than her. But when her fingers closed around my testicles I finally found the strength to protest.

"Please," I said, "it was an accident. He was going really fast. I didn't mean to, I tried my best, I swear."

She smiled warmly and told me that even though I'd done my best, I had to be shown that there are consequences for my actions. The squeeze would motivate me to do better next time.

I was about to ask, 'next time?', but she tightened her grip before I could make a sound. I cried out, my voice breaking almost instantly. It was a hard, fierce squeeze, but mercifully quick. She withdrew her hand right after, letting me double over in pain.

Then they sent me straight to bed. It wasn't even 8 PM yet, and I was tucked into bed with the lights turned off. I hadn't been to bed this early on a Friday . . . ever. I hadn't been tucked in with the promise of being checked on since I was at most seven. I was checked on only once, about an hour after bedtime. Ryan came in and sat on the bed next to me. He asked if I was awake, then asked how I enjoyed my special dessert .

"It's your sister's favourite, you know. Oh come on, don't cry about it. Jess tells me I taste better than her last boyfriend, so count yourself lucky."

That remark sent chills down my spine as he walked out. How many boyfriends had Jessica had before? How much had she done? I already knew her experience far outstripped my own, but just how far did it go? Did I even know what a blowjob was when I was her age? God, I felt so young, so immature next to her. It wasn't right!