My New Punishment Part 3

My New Punishment Part 3
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 3

I sat on a bench outside my school, watching dozens and dozens of my schoolmates bounding past, free and carefree. For most of them Friday meant forty-eight hours of freedom. There were plenty of jocks, the cool kids who planned to drink and party and probably get laid. There were guys more on my level, who would spend the weekend playing video games. And there were the girls, so many, so diverse, so incomprehensible.

And then there was me, probably the only one not happy for the ending school week. Because this was the fourth Friday of my new life, and I had finally gotten used to it, started knowing what to expect. Three Fridays ago, this had all begun when my classmate Ryan squeezed my balls for the first time. The Friday after that, Ryan had slept over for the weekend while my parents were away. That meant that he and my little sister Jessica, his girlfriend, spent the weekend spanking me and occasionally squeezing my balls some more. And, of course, Ryan made me suck his dick. Then there was last Friday, which had begun like the one before and like this one.

Last weekend my parents weren't out of town, so Ryan and Jess couldn't own me for the whole weekend, especially since Ryan didn't sleep over, lest he freak out my parents by getting caught trying something with Jess. But he did stay for dinner, during which the rule that kept me naked when he was in the house did not relent. My parents, of course, were amused. And I didn't escape that night unscathed. Jess asked me to clear the table after dinner, like I was the maid or something. I knew better than to question the order, but I made the mistake of setting all the plates down on the counter instead of loading the dishwasher. Jess said I was doing a half-assed job, assuming someone else would finish my chore for me.

A few minutes later we were all in the living room, and Ryan held me in the diaper position while Jess assaulted my butt with her hairbrush for my laziness. At least it was my first Friday without a ball squeeze since the beginning. Mercifully, Ryan left shortly afterwards, after giving Jess another sickening, wet kiss goodbye.

I sat on the floor sobbing, a quivering naked mess, while Mom and Dad talked to Jess about the whole situation. Needless to say they were delighted with how the whole thing was working out. The fact that I was constantly nervous around my little sister had kept me on my best behaviour, and I had stopped talking back. Ryan, they said, was an absolute joy to have around, so mature and so good with me. Dad confessed that he'd been a little nervous about the ball squeezing at first, but he'd warmed up to it rapidly after he realized how effective it was. He said he should have known that Jess and Ryan would give me exactly the punishment I needed, not more and not less.

I considered telling them that Ryan had also raped me in the mouth, but I couldn't stop crying. It was just as well. I knew I'd never be able to get the words out before embarrassment clogged up my throat. And why would they believe me anyway? Even a suddenly well-behaved kid like me had a naughty little boy at the core, and he would tell any lie it took to get out of future punishment. That was the story I knew Jess would spin, and the one I knew my parents would believe.

But as I sat there on the bench, waiting for Ryan to emerge from the school so we could walk home, I realized that it had been at least a week since I even thought about trying to find a way out. I was helpless to resist, of course. Not only was Ryan stronger than me, but my willpower faded to nothing in his presence or Jess's. But still, I had to at least have hope. Hope was something, even if it was impractical. At least if I kept telling myself I had to stop this, maybe my subconscious would work on a way.

Then I noticed Ryan strutting out of the school building, chatting with a couple of guys from the football team. I knew them as the guys who'd given me and my friends wedgies and purple nurples back in grade six. Ryan hadn't always been one of them. He'd been nearly friendless not that long ago, partly due to his arrogance and partly because of his weirdness. Ryan had straddled the line between jock and nerd, not as athletic as the athletes, not as geeky as the geeks, but smart enough and athletic enough to be on the fringe of both groups.

But now he played football with the big boys. His social status had risen considerably when his relationship status on Facebook changed to reflect his relationship with Jess. Conquering a grade seven girl was ballsy, and it earned him major points. And since it was public knowledge that he was dating my sister, no one asked any questions when the two of us walked home together. Thank God Ryan had agreed to keep my situation private. At least I hope he honoured that agreement. It drove me crazy sometimes wondering if he or Jess had really managed to keep it all a secret from their friends.

Ryan broke away from his friends and headed over to me, a smile on his face. I stood up and began walking with him. I unconsciously fell into step a few paces behind him, following him to my own home. But then I decided it was time to take a stand. The time was right, after all. We were in public so he couldn't try anything, but it was just the two of us on that sidewalk, so we could talk without being overheard.

I walked up beside him, which he noticed at once. I decided to start small, to be respectful and reasonable. That just might work.

First I respectfully asked permission to say something, which he seemed to like. He gave me permission, grinning as if to say, 'this ought to be good.'

I asked that my balls not be squeezed anymore. I appealed to him as a man, for my fellow man was surely aware of how terrible testicular pain was. I tried to explain that such punishment was unreasonable, even compared to spanking, and that it might even be harmful in the long term.

Ryan laughed it off. He made a joke about neutering naughty puppies, then put his arm around my shoulders. He calmly explained that, as a man, he was fully aware of the impact of a ball squeeze, and that he and Jessica were quite capable of applying just enough pressure to cause good, healthy discipline. My fertility, he assured me, was in no danger.

"Please," I said. "Please, it hurts so badly. Isn't the spanking . . . isn't it enough?"

He laughed again. Then, to my surprise, he turned a corner. I told him we were still several blocks from my house and we had just veered off in completely the wrong direction. He flexed the muscles in his arm, tightening his hold on the back of my neck. He knew the way to his girlfriend's house, he assured me. But that wasn't where we were going.

He explained that Jessica felt that the time she was spending with me and Ryan lately was cutting into her normal socializing. She had decided to take this weekend to hang out with her friends, leaving me in Ryan's capable hands. And since Jess was hosting her gathering at our house, I was to go home with Ryan. I suggested that I stay at my house and keep to myself, but Ryan shot that down without batting an eye. He said I was bound to do something wrong eventually, and it wouldn't be fair to Jess if she had to take time out of her get-together to spank me. And besides, the two of us were going to have some man-to-man fun.

"Man-to-boy fun, actually," he corrected himself.

Ryan's family lived in a condo, which made sense considering he was an only child. It was an awkwardly long elevator ride up to the fourteenth floor, but I remember the apartment itself was pretty nice. When he unlocked the door and ushered me in, I took a few tentative steps into the living room, examining my new surroundings. Modern furniture, big TV, nice wide window overlooking most of the neighbourhood...

Then a loud crack split the air. I pivoted to see Ryan standing by a leather sofa, having just noisily slapped it with his leather belt. I froze, no longer curious, now simply afraid.

Ryan listed not one, not two, but three spankable offences I had just committed. Firstly I had entered his home without taking off my shoes. Not only was it a violation of a rule, it showed disrespect that I would treat home with less consideration than my own. Secondly, I was still clothed. It was a sign of stupidity as well as disrespect that I had not assumed that my nakedness rule still applied here. My third crime had been committed before we even got there. Asking to be liberated from the threat of ball squeezes was a big mistake. I was supposed to accept my discipline, not question it. The only one who could prevent ball squeezes was me, by not being bad.

I sauntered back to the front hall and discarded my shoes, then stripped naked. Ryan's house had better air conditioning than mine, and I once again felt my dick shrinking to a nub and my nipples stiffening. As I walked back into the living room to receive my punishment, I looked at that big wide window again. I saw the school in the distance, its front doors still surrounded by a cloud of free, happy teenagers. Then my eyes refocused and I saw my own reflection, scrawny and hairless and totally exposed.

Ryan tried out a new spanking position, then. He told me to lie face down on top of the back of the sofa, one arm and one leg on either side. It was an awkward position to get into, especially since the leather couch wasn't exactly frictionless against my bare skin. And when I was finally in place, my dick and balls were squished uncomfortably against me.

Ryan explained that he was using the couch like an old corporal punishment apparatus called a horse. Customarily my wrists and ankles would be bound to the horse's legs, but that wasn't necessary in this case. He said I knew better than to move, didn't I?

For some reason he was unusually merciful with that spanking. I got five lashes from the belt on each of my butt cheeks, then another five across both. It was excruciating as always, but it was brief enough that I had only just begun to cry, and I didn't lose count of how much I'd taken. I looked up through my tears and the reason for the spanking's end became apparent.

A man stood in the doorway to the kitchen, and he could have been a clone of Ryan aged an extra thirty years. He wore a proud grin.

"So this is the kid you've been telling me about," Ryan's dad said. "You're right, he does look like a ten-year-old."

They shared a laugh, and Ryan's dad praised his son's work. He said that at first he'd been a little uneasy about his kid spanking another kid, that something about it didn't seem right. But then he realized that he hadn't had to spank Ryan in almost eight years, and that he'd been a picture of maturity since. And now that he'd seen me, seen the scrawny, hairless, immature little boy that I must be, it all made perfect sense. If I was 14 years old and still this pathetically childish, I was in desperate need of some stern guidance. And there was no one in the world more qualified than Ryan.

So Ryan's maturity and responsibility weren't just a show he put on for my parents. Even at home he was really that good a kid. But that still didn't give him the right to hurt me like this! Sure, I wasn't as hairy or brawny as Ryan, but I was every bit as smart as he was. Didn't that count for anything?

Then Ryan's dad explained what Ryan seemed to already know. His wife was already waiting for him up at their cottage so they could spend the weekend closing it down for the upcoming winter. That meant Ryan was to act as my babysitter yet again.

I shuddered at the thought of a weekend with just the two of us.

My tormenter's father left, then, leaving us alone. And Ryan seemed very happy about that. He told me to get off the sofa-horse and follow him down a hallway. I was a little surprised he wasn't going to continue my spanking. Don't get me wrong, I was definitely happy. Just surprised.

Ryan brought me to his bedroom, which, to my envious astonishment, actually had a lock on it. He opened it with a key he took from his pocket and ushered me inside. His room was an interesting and envy-inducing place indeed. He had a computer, nicer than mine and password protected. His bed was a queen-size, compared to my twin. He had another window with a glorious view, and even a telescope set up next to it. I hadn't known he had any interest in astronomy.

"It's not for astronomy," he said, reading my mind as I eyed the expensive-looking apparatus. He explained that it was a birthday present from an uncle who'd wanted him to get into astronomy, but he'd only found one use for it. A number of neighbouring apartment buildings had pleasantly wide windows as well, and a telescope was useful for curious spying. He said he even caught the occasional pair of breasts.

I realized that he probably wouldn't have told me that if Jessica were here. This really was a man-to-man atmosphere. Oh, sorry. Man-to-boy atmosphere. He was going to talk to me on a different level, maybe reveal a little more of that evil I knew was in him.

Then he just told me to lie on my back on his bed, lift my legs and spread them. I resisted the urge to sob. My tears from the last spanking had barely dried and I was already in diaper position for another one. And yet . . . this was unusual. Usually a diaper position spanking was a two-person job, one to hold me in place and one to spank. But Ryan just stood right in front of me and held my ankles apart.

Then my heart skipped a beat.

His pants were gone, and his rock-solid dick was sticking out of the fly of his boxers, looking bigger than ever. A part of me had suspected this was coming ever since the blow job, but I had managed to force myself not to think about it. But it kind of made sense. For Ryan a weekend without Jess was a weekend without sex. I had only ever jacked off, but maybe when you got something more than that, like Ryan had, you couldn't just go back to doing it yourself.

I scolded myself for even considering any justification for what he was doing. It was wrong. He had no right. I wanted to hate him for it, to complain at least, but I felt . . . so powerless. In this position, there was nothing I could do but lie there and take it.

"Please," I whimpered, "don't."

He looked at me with satisfaction, like I had only said that because I knew he liked to hear it. And I realized he was right. I couldn't effectivelyy beg for mercy, but at least I could get on his good side.

Then suddenly he let go of my ankles and walked over to his desk. I was completely taken aback. Could my plea have really worked? No, of course not. He reappeared between my legs and I instinctively lifted them back up. But I think Ryan rewarded my pathetic grovelling. He placed a couple of fingers on my butthole and I cringed from the wet chill, but I realized it was a big blob of some kind of lubricant. That was actually very nice, as it made what came next a lot easier.

At least I like to think it did. The only way to look back on that day is to remind myself that it could have been worse.

I squirmed and twisted for all I was worth while he forced his way in. It was by far the strangest, most violating thing he'd yet done. This was worse than the blow job. At least things going into my mouth was natural. Things were only supposed to come out of my butt. He was invading my body, and I felt like he was claiming it too. He had already come into my house, my room, and my family and made them all his own, but now I was his too. He wasn't just using me and torturing me, he owned me. This was it. If he could do this to me, he could do anything.

After he made it all the way in, he paused for a moment. Maybe he was just enjoying that weird sensation that his crotch was right up against my butt. Then he started thrusting, started fucking me. Truly raping me. It hurt, but not as much as I thought it would. Even though it was a hundred times more embarrassing and violating than a spanking or a ball squeeze, I managed to get through it without crying. I just lay there, feeling it, wishing it could be different.

I'm not sure how long he did it for. Maybe half an hour, maybe less. When he was done I didn't really feel his cum squirting inside me. It was probably lost in the gooey mess of lube. I cringed as he slowly drew himself out. He wiped off his dick with some tissues, then did the same to my butthole, stuffing his tissue-wrapped finger a couple of inches in.

Ryan was panting and sweating, much more than when I had sucked his dick. I could only imagine that this was how he was after he and Jess had sex.

That was the first time I ever let myself think those words. I had been aware that it was happening for a while, but I had never before allowed myself to imagine them together. Now, though, I couldn't help it.

Ryan tucked his dick, still half hard, back into his boxers, then he took off his t-shirt and tossed it in a laundry hamper. Standing there in just his boxers, Ryan looked quite intimidating. He was no body builder, but he was lean and defined. The physical contrast between my skinny body and his athletic one had never been out in the open before. His visible muscles, his big dick, the fact that he'd just raped me, even the fact that he wore boxers and I wore briefs – all of it just made me feel like nothing compared to him. He was rubbing my nose in it. I was a boy and he was a man. As if he hadn't just proven it. He owned me.

He offered me a hand. I lifted my limp arm to meet his firm grip and watched his bicep flex as he pulled me up to my feet. My legs were wobbly and my butt felt weird, but I managed to stay standing. Then he asked me if I liked it.

Once again I knew what he wanted to hear, and once again it was the truth. I shook my head and weakly uttered, "No."

He reached over and curled his fingers around my balls, holding them just hard enough that I tensed up with discomfort.

"You asked me not to squeeze your balls anymore, and even though you had no right to ask that, I was kind enough to offer you exactly what you wanted. What I just gave you was a potential alternative. If you had said you liked it, I would never have squeezed you again. I can't speak for Jess, of course, but your balls would never have felt my hand again. But you said no. You spurned my generous offer." He squeezed tighter. My face contorted with pain. "Now you'll have to live with both. All of it, really. Spanking, squeezing, sucking me off, and now your new punishment. And if you keep up this attitude of yours, Jess and I will probably have to add more to the repertoire. So be good, respect your betters, and don't question the rules."

He let my balls go and I fell to my knees, clutching them. Ryan lightly jabbed me in the ribs with his sock-clad toes, nudging me in a direction I couldn't recognize through the pain. I blindly but obediently began crawling that way, and soon found myself in the hallway outside his room. He said he would give me a few minutes to think about things while he got changed, whatever that meant. Then he closed the door behind me and I heard the telltale click of a lock.

I lay on the floor for a few minutes, waiting for all my pains to fade a little. I realized that I had been at Ryan's house for less than two hours and already he had spanked, squeezed, and fucked me. I shed a tear wondering how much worse this weekend could possibly get.

Soon Ryan's door swung open again. By then I had pulled myself up into a sitting position with my back against the wall. Ryan strode out wearing a skin-tight black tank top and a pair of knee-length athletic shorts, and his keys were on a lanyard around his neck. He tossed something to me that landed in a heap on my leg. It was a pair of grey gym shorts barely longer than boxers. He told me to put them on and I didn't hesitate. Other than being naked or just wearing my briefs, I couldn't imagine more humiliating attire. The shorts didn't reach halfway down my thighs and they flared wide enough that you could see pretty much everything if I spread my legs.

Ryan grabbed the back of my shorts and lifted me up with a savage wedgie. When I was upright, he started walking and told me to follow. I realized with horror that he was heading for the door. Before I could muster the courage to object, we were out the door and into the hallway. Ryan locked his apartment and we started moving.

I wasn't even sure if I could walk without exposing myself in those shorts. I kept my usual few paces behind Ryan, trying to keep up despite walking in very short strides to avoid the shorts flaring up. Being out in public made me very self-conscious again, suddenly aware once again of my stiff little nipples and the absence of any noticeable bulge in those skimpy little shorts.

A woman walked past us. She looked like she was in her mid thirties but she eyed Ryan's arms and chest with girlish curiosity as she greeted him. Then she noticed me, suppressed a giggle, and asked, "Who's your little friend, Ryan?"

If I wasn't completely petrified I might have run away. Adding yet another witness to my complete embarrassment renewed my shame for my nudity. I wasn't even completely naked, but I wanted to cover up more than I had in weeks. As much as I still hated stripping for Ryan or Jess, I had gotten used to it. Being exposed in their presence was becoming normal. But this woman, this stranger...

Ryan explained that I was his babysitting charge, then bid the mother adieu with a cryptic wink, and headed down the hallway. I followed, of course, a few steps behind, but he fell back so we walked abreast. The woman, he said, was the mother of his first girlfriend. They had dated for a year, the year of grade seven, and they'd shown each other quite a time. I had never seen this girl because unlike Ryan and me, she didn't go to school in the area. She had attended private schools all her life, and her relationship with Ryan had ended at the start of grade eight when she left for a boarding school. He even confessed that he had considered Jess a bit of a rebound girl at first. Grade nine had just started and the old flame had left for parts unknown...

At that moment I was almost in tears for sheer jealousy. I knew guys had been dating since grade seven, but to stand in the presence of a guy who'd lost his virginity at age 12 was just painful.

We entered the elevator and Ryan sent it down, all the way down to the basement. It stopped after a few floors to admit a couple of boys who looked about 9 or 10. They had quite a laugh at me. They got off at the first floor, leaving Ryan to tell me that he frequently babysat one of those boys. In fact, he was the first charge he'd ever spanked. I was taking an odd little tour of Ryan's world.

Finally we reached his destination: the building's gym. Ryan said it was time for his afterschool workout, and I was going to work with him. He'd given me the shorts because it was against building rules to exercise naked.

I realized that this was just more punishment. He ordered me through push-ups, sit-ups, and a half-hour of jogging on an exercise bike. He seemed invigorated as he outpaced me in each activity, but I was exhausted and in pain almost instantly. I didn't work out. My body couldn't do what his could. He did twenty chin-ups while I struggled with one. Then he walked over behind me and gave me a hand, lifting me a foot or two higher by the back of my shorts. When he let go I fell to the ground on my butt. My shorts were so hiked up from the wedgie that my dick and balls stuck out one of the legs.

Ryan laughed. Then abruptly he stopped laughing.

"You know what I just realized?" he said. "Since you put on those shorts in the hallway, you were technically in my house, in my presence, not naked."

I just whimpered. To complain that I was just following orders would be useless.

He helped me to my feet and walked me over to a weight bench. He sat down, his thighs parallel to the ground, and I knew what to do without being told. I lay down across his lap, my legs to his left and my upper body to his right, and my shorts-clad butt sticking up in the air above his legs. He gave me yet another little wedgie, causing the shorts to all but vanish between my butt cheeks.

Ryan had never spanked me with his bare hand before, but there on that bench, surrounded on all sides by the machines and weights and other equipment that had been strengthening his arms for years, he showed me what he was capable of. And it wasn't any less effective than a hairbrush or a belt.