My New Punishment Part 4

My New Punishment Part 4
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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Our parents were away on business, so Jess and I were having a lazy Saturday afternoon at the house. Lazy for her, at least. For me it was pretty stressful. Jess was reading a book and simultaneously filing her fingernails. The nail filing kept both of her hands occupied, so I held the book for her. I suggested that she just tell me when to turn the page, but she’d pinched my cheek and called me uncreative. Her solution, she said, was much more fun.

She kept her foot planted squarely on my crotch; when it was time to turn a page, she applied a little pressure to my balls with her toes. She didn’t press too hard, but it was a signal I couldn’t ignore.

How easy would it be to just get up, put my clothes back on, and say “No more”? Once again I looked at my little sister’s slender leg, lean and fit, but not exactly muscular, and told myself that she could not overpower me. Sure, I was a little on the weak side for a 14-year-old boy, but I could easily overtake my 12-year-old sister. Without Ryan around, and without my parents . . .

Jess’s toes flexed. I winced and turned the page of her book. Actually, holding the book up was starting to make my arms tired. Soon they’d hurt almost as much as my balls. This was unreasonable. This was just ridiculous. How could anyone let this happen?

Suddenly Jess looked up at me over her book. “Whatcha thinkin’ about?”

I looked down. It was better to look at her toes on my scrotum than into her eyes.

“Nothing.”

She giggled. “I’ll take your word for it.”

No, I couldn’t possibly overpower her. I couldn’t even look her in the eye. Once again I told myself that there was only one way out of this: being a good boy. Doing what I was told. Following the rules. Sitting naked on the couch and letting my little sister squish my balls for fun. I really was too pathetic for it to be any other way. If I’d let myself get into this, I obviously didn’t have what it took to get out.

Suddenly jess pressed down on me again. I didn’t think it had been long enough for her to have read a whole page, but I flipped it anyway. But she didn’t take the pressure off my balls. I felt muscles contracting all over the lower half of me as my body begged for escape. But I kept myself there, under her toes. It would only get worse if I pulled away.

But the pain . . . so intense . . . there’s something profoundly horrible about a constant, light ball squeeze; it builds up to be even worse than a hard quick one.

“What do you want?” I wheezed.

“This means close the book,” she said.

I did, and I immediately dropped it on the coffee table to relieve the building pain in my arms. Jess released my balls, but that pain lingered more insistently. It was neither nice nor reasonable of her to introduce a new phrase to this code of ball-squeezing without explaining it first, but it was no good telling her that. Better just learn it for next time.

Would there be a next time? I really hoped Jess wasn’t planning on communicating with me entirely through ball squeezes. I don’t know if I could interpret a more complex code while dealing with the pain.

Mercifully Jess crossed her legs, withdrawing her toes from my groin. I sighed heavily.

My sister looked very frustrated. Ryan was away with his new guy friends for the weekend, on a camping trip, I think, and Jess was very bored in his absence. I think she was more interested in

toe-squeezing my testicles than in reading her book. I wondered why she didn’t just hang out with her girlfriends, and she seemed to be reading my mind.

“This sucks. All my friends are hanging out with their boyfriends, and mine is on some stupid boys’ weekend.”

I cringed. Ever since the beginning I’d feared this moment. Things weren’t going her way, and she had no one to take it out on but me. And my only hope for eventual freedom was to just lie there and take it. She was mad at her friends for being off with their guys, she was mad at Ryan for being off with his guys . . . Why didn’t I have guys to go off with? I had friends at school, but I just felt weird socializing now that Jess and Ryan had taken over my home life. Actually, my friends were probably wondering why I hadn’t been hanging out with them recently.

The answer, of course, was that Jess would be mad at me if I went off with my friends, just like she’s mad at Ryan. He had the right to go out every now and then, and all she could do was get annoyed. But I was her property. I couldn’t go out without my dear sister’s permission . . . unless I was looking for a spanking of truly terrible proportion.

But what if I got her permission? What if I asked her . . . and she said yes? Maybe she could use some alone time. She certainly hadn’t had much lately. And maybe she’d idly tortured me enough for one day. If that was true, if there was even the slightest chance that it was true, I needed to make her realize it before she started abusing me to get back at her friends and boyfriend for abandoning her.

“Uh, excuse me,” I said. I’m not sure when, but somewhere along the line I’d lost the ability to address her by name.

She looked at me with a surprised but patronizing smile, like she was looking at a baby who’d just said his first words. “Something you’d like to say?”

“Well, I . . . I just haven’t spent time with my friends in a while. Do you think maybe I could . . .”

She hmmmed emphatically and reclined on the couch’s armrest, extending her legs into me so I had to recline too. My stomach became a footrest for her. I noticed that I could see up into her little miniskirt from here, but she crossed her legs at the ankle before I could even tell what colour her panties were.

She was looking up at the ceiling intently, clearly thinking. She unconsciously pinched my nipple between her big toe and second toe, and I resisted the urge to squirm away from that. That was so odd, how even after all this, I still had the instinct to shy away when they violated my personal space, to push their hands away when they reach for my balls. It was just getting slightly easier to resist that instinct. The humiliation was always there, too. Sitting there naked in front of my sister never got any easier; it was as embarrassing now as ever

“You know,” she said suddenly, “I think this whole set-up has a big problem.”

My heart was racing. A problem with the whole set-up? Was she about to change it? Could she actually end it?

“The problem is that we’ve kept it all in the family.”

My heart just about stopped, and then started racing even faster. Keeping it all in the family was the one thing I appreciated about all this. If that was a problem . . .

“You’re clearly an irresponsible little boy, Jake, and you really do need constant supervision, either from Mom or Dad or one of your nice babysitters. But Mom and Dad have to work a lot, and me and Ryan both have our own friends, and also our time with each other. This has worked out pretty well for this past month, but I think you’re going to need some new babysitters going forward.”

Then my heart definitely did stop for a second or two. “No,” I said. “Please.” I scrunched up my face as I held back tears. Retreating from Jessica’s feet, I rolled off the couch and got down on my knees. “Please,” I begged. “No one else.”

I just sat there, hunched over, eyes clenched shut, for about thirty seconds. Then I heard a familiar sound: the sound of Jess’s palm clapping down on the skin of her thigh. She tapped it twice, and I knew what was coming. When I looked up she was already in position, her back straight and her thighs parallel to the floor. She patted her thigh again.

I straightened up and wiped away a tear that had crept through my wincing. It was a pointless gesture, as Jess certainly knew. Seconds later I was over her lap; she flexed a thigh muscle against my dick, squishing it into my pelvis. She actually was quite fit; maybe I couldn’t overpower her after all.

The spanking was as brutal as Jess could muster with her bare hand. It was painful, but I only cried a little. It really was the least of all the spankings I could get these days. Jess’s hand was nothing compared to Ryan’s, or to the hairbrush she sometimes used. I was sobbing, but I still had the strength to prop myself up when it was done. I got down on all fours because it was the only comfortable position that kept my butt friction-free.

Jess seemed to like that position; she knelt beside me and lightly grabbed the scruff of my neck like I was a dog.

“Jake, when I decide something like that, you don’t get to say no. If you were mature or responsible or smart enough to make those decisions yourself, you wouldn’t need me here babysitting you.” She ran her hand down my back and onto my butt, stinging horribly. “But I guess I do my best thinking while I spank, because I had an excellent idea. We’re going to bring someone else into this. You’re getting another babysitter.”

I held in yet another futile protest, but I couldn’t stop myself sobbing a little harder.

“Oh, but it’s not all bad! I shouldn’t be doing anything nice for you after your little show of disrespect, but I’m in a nice mood today. You’re going to be spending more time with your friends from now on, because one of them will join our babysitting team.”

I found the strength to raise my head and look her in the eye, begging ‘no’ with my tear-streaked facial expression. She just smiled.

“But it gets even better for you. You know your friends a lot better than Ryan and me, so I’m going to let you choose which one it should be.”

My shoulders began shaking; the fatigue of holding up that book was returning to my arms. I almost said ‘no’ again, but I channeled it into something that would offend her less.

“I . . . I can’t.”

“Of course you can. You’ve known those guys for years, and all you have to do is say a name. I’ll do the rest.” She got to her feet. I followed her up with my eyes, but when she was fully upright I just found myself looking up her skirt. I respectfully looked back down to the floor. “I know this is a big decision, Jakie, so I’m giving you one week to make your choice.”

I started to crawl away so I could look up at her and reply, but she stuck her toes in my side and pushed until I fell over and rolled onto my back. Now I found myself looking right up into her face.

“But you’d better have a name for me by next Saturday. If you don’t, I’ll choose one of my friends instead. And I’m guessing you’d rather be babysat by a guy who likes you than by some 12-year-old bitch who’ll probably let her boyfriend fuck you in the ass.” She gave a sinister little wink.

My eyes widened. She knew. I was wrong about Ryan; I’d thought he’d keep it between us that he’d sodomized me. I thought he’d gone too far with that one, and wouldn’t tell Jess about it. But I guess it was like he said . . . just another punishment. Jess probably didn’t even think of it as sex. More like masturbation but not quite as pathetic.

Jess walked away, and I lay there prone on the floor, afraid to move and chafe my butt against the carpet. I think Jess made

lunch or something; she asked if I wanted any, but I was too caught up in my own thoughts to answer. I was going through my friends, weighing the pros and cons of each, trying to guess which would make this hard and which would make it easy. I didn’t have that many friends, so it didn’t take long to go through them all over and over again.

Could I trust any one of them not to tell the others?

Could I trust any one of them not to take advantage, like Jess and Ryan did? They were my friends, but they could be jerks just like anyone else. Was any one of them mature enough to handle this responsibly and humanely?

My heart skipped a beat. Mature? Yes, that was it. That was what it came down to. I needed a mature, responsible babysitter. A mature and responsible babysitter would be fair and just . . . he wouldn’t do what Jess and Ryan did. If I could choose wisely, and pick the most mature and sensible of my friends, not only could I avoid a lot of pain and humiliation, but I could bring it to Jess and Ryan as evidence. ‘He’s more mature than you are, and I was mature enough to recognize it!’ That was too good an argument for them to ignore. And moreover, I’d have an ally.

Yes, this was good. As terrifying as it was to consider one of my friends knowing about all this, it could be the key to ending my humiliation once and for all. Ryan would be so furious when I finally managed to escape! He’d made me a slave, and Jess had just handed me the key to freedom. Maybe he’d get as angry at her as he did at me. Yeah, that was a nice thought: Jess getting punished like she punished me. I couldn’t think of any way for Ryan to get his comeuppance, but being out from under his thumb was good enough for me.

Pleasant as those thoughts were, I knew I had to bury them. Jess and Ryan both had a habit of knowing what I was thinking like it was written all over my face, and I didn’t even want to think about what they’d do to me if they knew I was considering this.

But, of course, I did think about it, and the lifetime of spankings and ball squeezes that flashed before my eyes almost

made me want to forget the whole thing. But I didn’t. I just kept telling myself, ‘you can be free.’

One thing at a time, though. First I had to make a choice, and I had to make it very, very carefully.

***

I thought about my decision constantly over the next twenty-four hours. I even made tables and charts on my computer, trying to add up all the pros and cons of each of my friends. I listed everything I could remember them doing that was mature or immature, that showed a sadistic streak or a sympathetic one.

But it was tough, because I couldn’t save my work. If Jess or Ryan saw what I was doing, they might suspect my goal, so I had to delete it all in the evenings, and reconstruct it from memory in the morning. Everything on my computer was an open book to Ryan and Jess because of another development in my punishment. Earlier that week Ryan had decided I had too many basic freedoms, so he decided to rob me of my right to masturbate. In addition to removing the box of tissues I kept in my room, this meant he and Jess now regularly checked my computer for any traces of porn.

Not only did they check my browsing history and search my hard drive, but they’d taken steps to make certain I couldn’t hide anything. Ryan had granted me my wish for password protection, but only he and Jess knew the password, so they controlled all my access to my computer. Moreover, he’d installed some second-rate third party browser that didn’t have a privacy mode and couldn’t delete its history. And I couldn’t install another browser without Ryan’s administrative password. And if I did web search for a solution to all this, it would show up in my history and my balls would suffer.

I could still masturbate in the shower, of course, and in the bathrooms at school, so it wasn’t too big a problem. I just hated having restricted access to my own computer. Especially since Jess always made me log out when my curfew hit, which was at 10:30 on weekends.

So at 10:38 on Sunday night, I was lying awake in the dark, naked except for the blanket. Ryan had said he might come home that day, so I’d spent the whole day naked just in case. But neither he nor my parents had made an appearance. And I’d managed to get through the whole day without drawing my sister’s wrath.

I was going over my friends for the billionth time. I’d finally managed to narrow it down just a little by eliminating Curtis. He was just too mean-spirited. That left three candidates, and I meant to have it down to two by Wednesday. With luck, seeing the guys at school would help me make my choice. Maybe I could even ask some covert questions to assess their maturity.

I was trying to think of a casual way to ask whether my friend Sam believed in corporal punishment when I heard the front door open and close. Jess didn’t go out this late on school nights, so it had to be someone coming in. And I only heard one set of footsteps. Theoretically it could have been Mom or Dad, since their trips were separate, but they usually met up at the airport and came home together. That really just left one possibility.

The footsteps seemed to travel down the front hall at an oddly irregular pace, then turned into a series of rising thuds as they began to climb the stairs. Jess usually met Ryan at the door, but I guess she was in her room listening to music so she didn’t hear. But the footsteps seemed to be going in the wrong direction. They were coming toward my room, when Jess’s was in the opposite direction.

And still that odd irregular pace, like he was zigzagging down the hall instead of walking in a straight line.

My door creaked open, and Ryan stood in the doorway, a demonic silhouette against the light from the hallway. He looked larger than life, and downright menacing, but it was unmistakably him. I squeezed my eyes shut. Maybe if he thought I was asleep, he’d leave me alone.

But he didn’t. He started walking toward me, slow but with heavy footfalls. I kept my eyes shut, but as he got closer I could smell him. There was an earthiness around him; he’d definitely

come straight from a camping trip. And he smelled like he was coated in dried sweat, overlain with a liberal layer of some deodorant body spray, like he was trying to cover the fact that he’d spent the last 72 hours hiking and climbing and mountain biking without a shower.

Then he was right beside my bed, and I got a whiff of something else. It was periodic, coming with his heavy breathing. Beer, I realized, remembering all the times I’d smelled my dad’s. Ryan was drunk!

Then there was the familiar sound of a zipper sliding open, and another smell: that different musty sweat that came out around the groin.

Something soft touched my lips, and I knew what to do. Still doing my best to pretend I was asleep, I licked my lips, sliding my tongue along the underside of his dick’s head. I heard him grunt with pleasure, so dumb and animal-like compared to his normally sophisticated demeanor. I parted my lips a little, and he shoved himself in. He was still soft, but he seemed to fill my mouth.

I felt him pull the covers down, exposing me from the shoulders up, and he tickled me under the chin with a couple of fingers. I knew what he wanted. I moved my head back and forth as much as I could without making it obvious that I wasn’t just sleep-sucking, and rubbed my tongue over the sensitive spots. I wanted to make him come as fast as I could. Then he’d lose interest and go away . . . I hoped.

But he didn’t come. Instead he withdrew his emasculatingly big member from my mouth not long after it reached its full stiffness.

“Thanks,” he said, louder than he would have needed to, even if I was awake. “Now I’m ready for your sister.” He gave my cheek a painful pinch. “If you like my dick so much, come join us some time. I’ve got enough for both of you. Hell, I’ll fuck your whole family. They seem to like me enough.”

He did a quick pelvic thrust, poking me in the eye with impressive accuracy. Then he left, fly still open, dick sticking straight out in front of him like a jouster’s lance.

I wondered how Jess would react to this. He certainly wasn’t his usual charismatic self; maybe she’d find this crass Ryan disgusting and turn him away. But no, that was so very wrong. It wasn’t even a minute before I heard her moaning with pleasure louder than ever before.

They kept me up till 3:00 AM, so loud I could barely think about my problem. I was very tired the next morning.

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To be continued . . .

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A note from the author:

To anyone who’s enjoyed this series of stories, I sincerely apologize for taking so long to add to it. Inspiration comes and goes, and sometimes life gets in the way of writing. But I’m back, and I hope to have more installations in the not-too-distant future. (Same goes for other stories, by the way, but this is the one I’ve neglected the longest.)

Some readers may remember that I submitted a different fourth chapter last year, which I asked Cassie to remove from the archive shortly thereafter. Sadly I went of half-cocked with that one. I sent it in without proofreading it, and it wasn’t until I saw it on the site that I realized it was badly written and that it took the plot in a direction I didn’t like. I thought that if that was the best I could come up with, this story might just be dead. Fortunately I was wrong about that. I just needed some time for inspiration to strike.

The original chapter four introduced a new character, one of Jess’s friends, and she accomplished nothing because she was basically a clone of Jess, and did nothing Jess couldn’t have

done alone. I reworked the “sister’s friend” character into Emily from “Emily’s Gift” and the girls from “Andy’s Difficult Weekend,” where it works much better. Instead I think one of Jake’s own friends will be better suited to the task of breathing life back into MNP. He’ll be completely unlike Jess and Ryan; better for Jake in some ways, worse in several others. And, of course, now the installments of MNP can come in four different flavors: Jess, Ryan, Jess and Ryan together, and Jake’s friend. And there can be some more drama down the line when the babysitters start butting heads.

But any more than that would be telling.

Stay tuned,

Nocti