My New Punishment Part 5

My New Punishment Part 5
By Nocti Raven
nocti.raven@gmail.com

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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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Sam was one of my oldest friends. Years ago, when I was too shy and awkward to make friends on my own, he’d talked to me in class, brought me into his circle. I owed him a lot. And by Wednesday, he was looking like the ideal candidate for the position of my babysitter.

Despite what Jess and Ryan liked to say, I really was one of the smart kids at school. And of my circle of friends, only Sam was as smart as me. And if intelligence didn’t signify maturity, what did?

Sam had other advantages, too. He was a pretty small guy, and he’d taken some flak over the years for being one of the short kids, so maybe he’d be a little more sympathetic to my slow-coming puberty. He wasn’t quite as skinny or awkward as I was, and he’d actually received some positive attention from girls for his curly hair, but he was still a social misfit like me, and no less a virgin to boot.

And he hated Ryan almost as much as I did. Before Ryan had started dating Jess and jumped up the social ladder, he’d been a real weirdo, neither jock nor nerd. The jocks ignored him, so he tried to hang out with us nerds, and we all got pretty sick of him.

Yes, Sam was looking like a pretty good choice. The only thing that concerned me was his sometimes perverse sense of humor. Sam was a funny guy, through and through. Always making jokes, taking nothing seriously. And he never held back when the jokes were at someone else’s expense. But how much of it was all in good fun, and how much was genuine cruelty?

For that reason, I couldn’t completely rule out Zack or Allen. Zack had been my very best friend back in sixth grade, and even though we’d grown apart a little, I still thought he’d have the most sympathy for me. And yet he was probably the least mature of all of them, and perhaps the most likely to abuse the position. And Allen . . . well, Allen had an angry streak. He was a really good guy, but it didn’t take much to set his temper on fire. That was not a good quality in a babysitter and disciplinarian.

Then, at lunch time, something happened. Wednesday was pizza day at the school cafeteria, which meant long lines at the lunch counter. Sam and I had math together before lunch, and math ended early so we got to skip the line. We were sitting together enjoying our pizza while the rest of the gang was stuck in the queue.

“Long line,” Sam said idly. “Almost as long as my schlong.”

“Your what?” I said. I was book-smart, not street-smart, so there were some gaps in my vocabulary where slang was concerned. Really, I should have guessed what he meant from the context, but I guess my mind was on other things.

“You know,” he said with a grin. “I have a schlong, you have a schlort.”

That time I got it. “Fuck you,” I said. It was the only way you could respond to things like that. If you took it in stride, it meant it was true and you were too embarrassed to deny it. If you denied it too emphatically . . . that was basically a confession, too.

Sam chuckled. “Well . . . it’s true.”

“What is?”

“That you have a schlort. A chode. A teeny weeny.”

I froze for a second. He was confident now; this was no joke.

“I do not,” I said, trying not to sound too serious.

“Yes, you do. I’ve gone to the bathroom with you, and you always use the stalls instead of the urinals, even when all you have to do is take a piss. It’s obviously ‘cause you don’t want anyone to see your tiny dick.”

“No it’s not! I just like the stalls better. It feels like I’m at home.”

He kept grinning. “It’s the same reason you never change your pants before gym. We would all see how small you are through your tighty whities.”

Not once, in all the time I’d known Sam, had I ever disrobed in front of him. How did he know I wore briefs?

“You’re crazy,” I said. “I wear boxers, just like you.”

“Oh yeah? Then show me.”

“You want me to take my pants off? That’s gay, you-”

“Keep your pants on,” Sam said. “Just pull the waistband up a little. If you’re wearing boxers, it should be obvious.”

I tried not to look scared, but he’d cornered me. Everything he said was right, and I had a feeling my expression had just confirmed it for him.

He laughed and clapped me on the shoulder.

“Relax, Jake. I won’t tell anyone. It’ll be our ‘little’ secret. But just for the record, you do a pretty shitty job hiding it. If you stand close to the urinal, no one can see anyway. And if you don’t want anyone to know about your tighty whities, make sure to pull up your pants before you bend over to pick something up.”

Allen, Zack, and Curtis showed up a couple of minutes later, and I didn’t contribute much to the lunch conversation. I was replaying that brief dialogue with Sam in my head, analyzing its implications.

That was it. The decision was made. It absolutely, positively had to be Sam.

‘I won’t tell anyone,’ he’d said. He knew such an intimate, humiliating secret, and he refrained from telling. None of the other guys could be trusted to do that.

And, of course, since he already knew about my briefs and my size issue, I had that much less to lose by revealing everything. If I chose anyone else, then two friends would know about that stuff.

And there was another thing, too. Sam had proven that he was very perceptive about very private things. If one of the other guys became my babysitter, even if he didn’t tell anyone, it might not have stayed secret from Sam for very long.

I stole a glance at my oldest friend. He was laughing at something Curtis had said, his blue eyes squinting through his glasses. That curly hair was bobbing with every guffaw.

Would he laugh like that when he learned that my little sister was my babysitter? Would he laugh like that when he was told he could spank me and squeeze my balls? I thought about Ryan, about the terrible things he’d done to me, and I wondered if Sam would laugh at those. Would he do them, too?

No, he was my friend. He wouldn’t do that.

But it didn’t really matter. I’d made my choice.

Sam would be my new babysitter, for better or for worse.

***

Ryan came over for family dinner that evening, and as always he engaged my parents in conversation like he was an adult himself. Even though we were only in ninth grade, he was already planning for college and beyond. I can’t say what his plans were, exactly, because I tended to tune out when he went on about stuff like that.

And it’s hard to even pretend you’re interested in the conversation when all you can think is ‘I wish I wasn’t naked; it’s so cold in here!’ Turning up the air conditioning was Ryan’s suggestion. Such a swelteringly hot day, he’d said. I disagreed, but said nothing.

But I snapped back into reality when I became the subject of discussion. Ryan had chosen this meal to tell my parents the good news that I’d be getting another babysitter. It was Jess’s idea, and I wasn’t sure Ryan would be on board with it, but now he seemed downright enthusiastic. Maybe he was happy to get more free time, or maybe he just liked the idea of adding another witness to my humiliation.

My parents also liked the idea. Every time Jess and Ryan ran something by them, I prayed that Mom and Dad would veto it and say they’d gone too far. To that end, I considered telling them Ryan had made me a kind of sex slave. But that was something I could never do. That was something I could never even talk about.

Then, for the first time in over a month, I was included in the conversation. Mom and Dad were both very curious about my choice, and Mom asked if I had a shortlist. I hung my head, staring at my food, not sure how to answer. Should I reveal that I’d chosen Sam? No, that was a bad idea. I had to make it look like the decision was horribly difficult, that I was putting it off as long as possible. Any hint that it was easy might have let on that I planned to benefit from this.

And if I told them I’d made my choice, they might bring Sam into the fold that much earlier. I was confident that he was the right choice, but I was still dreading the embarrassment of his formally becoming my babysitter. Keeping quiet might delay things just a little longer, so I kept quiet.

But keeping quiet was a bad idea, too. Ryan, who sat next to me, reached under the table and gave my right testicle a little pinch. I winced, nearly dropping my fork.

“Your mother asked you a question, Jake.”

“I, uh, I don’t know. I’m thinking about it.”

I guess they got the message that I couldn’t contribute much to the discussion, so they went back to talking about me as if I wasn’t there. Mom rattled off my friends’ names, but she didn’t know any of them well enough to speculate on which I might choose. Dad apparently didn’t think I was up to it, because he asked what would happen if I couldn’t decide. Jess explained her plan to bring in one of her own friends if I failed to make a choice. Thank God I dodged that bullet.

“Then again,” Jess mused, “If he manages to narrow it down to two or three, we could hold auditions. Invite them all over to spank Jakie and give the babysitter job to whichever one does it best.”

“Whichever one does it most thoroughly, you mean,” said Ryan.

Everyone but me found that very amusing.

“Now now,” said Mom. “Holding auditions kind of defeats the purpose of having only one new babysitter.”

I had the impression that I was only to speak when spoken to, but if I could have I would have thanked my mother a thousand times just then. For the first time she was standing up for me.

“If you invite two or three of his friends,” she continued, “you might as well invite all of them. And your own friends as well. And any of Ryan’s. Hell, just post ads at your schools: babysitter wanted for 14-year-old brat. No pay.”

Everyone laughed again. I sank into my chair, wishing I could just slide under the table and disappear.

Mercifully, that was just a joke. With a patronizing pat on the thigh, Jess assured me that only one new person would become part of the arrangement.

Then she said something that made my dick shrivel to a button and my scrotum contract to a patch of wrinkles. I very nearly began to cry.

“One at a time, anyway.”

***

On weekday Ryan usually left an hour or two after dinner. He and Jess couldn’t have sex while my parents were around, so there was no reason for him to sleep over. But today he’d brought an overnight bag.

He explained that he had an early morning football practice tomorrow, and our house was slightly closer to the school than his, so it was more convenient to stay here.

I was a little miffed; I wanted him to leave so I could put some clothes back on. But, as always, I knew better than to complain.

After dinner I went up to my room to do my homework. I was trusted to be alone and not put clothes on because of another of Ryan’s bright ideas. He’d rigged my dresser with some kind of noisemaker toy; no matter how slowly or gently I went, I couldn’t open my dresser drawers without setting off a clacking sound that you could hear anywhere in the house.

I resisted the urge to check on Sam’s recent social networking, lest my browsing history alert Jess and Ryan to my choice prematurely. I guess I could have looked up all my friends, but that would have been a waste of time. I finished my homework and curled up with a book until bedtime.

I’d brushed my teeth, said goodnight to Mom and Dad, and shut the lights by 10 PM, as required.

But for the second time in a week, my attempt to sleep was interrupted by Ryan opening my door. I groggily opened an eye to confirm that it was him in the doorway. He was holding his overnight bag in one hand, and a bundle or something in the other. And he wore nothing but his boxers.

It was almost midnight, later than last time. But at least he didn’t seem drunk. That had been unusually scary . . . like he might go even farther than he already had.

He closed the door behind him, and became invisible in the dark. Gently this time, he walked over to me and ‘woke’ me with a pinch on the cheek.

“Hey,” he said softly. “Your couch is a bit lumpy, and your parents probably wouldn’t like me bunking with Jess, so you and I are roommates tonight.”

He dropped the big bundle he’d been holding. My vision had adjusted enough to see that it was a sleeping bag.

But he didn’t get in the sleeping bag.

“Well?” he said. “Get up. The bed’s mine.”

With an involuntary groan, I sat up and left my bed. Once again I found myself standing next to Ryan, and once again the contrasts were painful. His height was average, mine slightly less. He wore boxers, I was naked. He had muscle, I had nothing. He had leg hair, I had nothing. His dick bulged forth in the fabric of his underwear, mine . . . was nothing.

He lay down on my bed and pried open the fly of his boxers. His dick popped out; this time he’d come to me already hard.

He leaned back, put his hands behind his head, and said, “Go on. Make your sister jealous.”

I suppressed another groan. I was tired. I didn’t even care about the humiliation; I just wanted to sleep. But that wasn’t an option. I climbed back onto the bed, knelt between his legs, and lowered my lips around that big throbbing cock.

It occurred to me that I was doing this largely unsupervised. Jess wasn’t watching, and Ryan’s hands were way on the other side of the bed. There was nothing he could do to me. There was nothing he could do if I . . .

I could squeeze his balls, just like he squeezed mine. They were big, but I could still get them in one hand. I could say, “promise it’s all over, or you get what’s coming to you.”

I could have, couldn’t I?

Could I?

I was tired. I had to be overlooking something. There had to be some consequence, some problem I couldn’t remember. Ryan was the one that squeezed my balls, not the other way around. I was disturbing the natural order of things; I couldn’t possibly get away with it.

But he had balls, just like I did. Wasn’t he disturbing the natural order by saying only mine could get squeezed?

No, that was wrong. This was perfectly natural. He was the man, I was the boy. His balls were his strength, mine were my weakness.

I couldn’t squeeze Ryan; the world just didn’t work that way. Somehow, sometime, there would be consequences for defying the order of the universe.

Then Ryan sat up, withdrawing his dick from my mouth. I looked up at him, my lips still forming an O. For a sleepy second I wondered if he really could read my thoughts, or if I’d somehow managed to articulate them with a dick in my mouth.

“Now that I think of it,” he said, “you’re up past your bedtime.”

He grabbed my ankles and lifted my butt out from under me. Before I knew what was happening I was on my back. Ryan was holding my ankles uncomfortably close to my ears, and his dick, now a massive nightmarish column of shadow, glistening with my saliva, was hovering over mine, making it look like a baby’s in comparison.

He leaned forward and whispered to me:

“I don’t care who else gets to spank and squeeze and fuck you. You and I will always know . . . your ass is mine.”

We were both very careful not to make a sound as he thrust into me. I think it was harder for me, though. If I’d known he’d be doing this, I would have unloaded more spit on his dick. It was much harder without the lube.

But he seemed to be even more into it than last time . . . or maybe this kneeling position offered some advantage over when he stood. Either way, I think I felt him going deeper, touching something that . . . something I hadn’t known was there.

For a few fleeting seconds, it almost, just almost, felt good.

When he’d come, he threw me down onto the sleeping bag and quickly got comfy in my bed. Within ten minutes he was ever so softly snoring.

The air conditioning had been turned off, but I’d never felt so cold in all my life.

And for some strange reason, my dick was hard as steel.

The End