Femdom Watching Little Sister Ch. 06

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A man decides whether or not to gamble with his release.
2.1k words
4.49
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Part 6 of the 7 part series

Updated 12/09/2023
Created 06/03/2023
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So this was originally part of chapter 5, but it was just too long as one chapter and had an ideal point to separate them in the middle. Thoughts on the pacing of this section (including the last couple of chapters) and the game in this chapter would be appreciated.

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"I bet you want out of that cage, don't you?" Cynthia said whilst we were waiting at a red light on the way home.

I looked at her, "god yes."

She toyed with the key and necklace with her fingers, "but I think it would be really boring just to give you the key and tell you to get on with it."

"Maybe it'd more exciting if you helped?"

"Or I could give you a choice." She smiled. She really was smiling a lot more lately. It didn't necessarily mean something good though, at least for me.

I got honked to start driving but then was able to ask, "what kind of choice?"

"To roll a dice or not roll a dice."

"Okay..." I said nervously.

"But if you don't roll the dice, I'll give you the key for ten minutes to take care of yourself alone in your room."

Well that would be even more boring, so I could already tell that she wanted me to take my chances to make this more interesting. But when I asked for details about the dice roll she just told me to wait, but that I had to make choose whether to roll or not before I pulled into the driveway.

About ten minutes later she said, "If you roll a one, you're not getting out of the cage until Wednesday."

There was no way I was going to take my chances in that case, I'd never been this desperate for an orgasm in my life. I couldn't deal with this for three more days.

Cynthia laughed. "The higher the dice roll the better time you'll have."

Yeah, but two and three could just be wait until Tuesday and Monday respectively. I couldn't take a fifty-fifty chance on not getting off today.

And then Cynthia put some music on with the car radio and told me to think about it.

Right. So even if I made the boring choice, she would have enjoyed tormenting me with the choice for an hour. Even if this choice wasn't hard - I was not rolling any dice - I was excited by her giving me one. It was a little twisted and it made me like being dominated by her more. Like she could have just told me I was waiting until Wednesday and tormented me that way, but this, this was much more interesting.

About ten more minutes later Cynthia turned the radio down. "If you roll a two, I'm going to put some nipple clamps on you and stuff your mouth with my pants or socks before I let you out."

I protested about having been hurt enough for one day, but Cynthia shut me down quickly, "I'm not going to be making you roll the dice and I'm not going to be the one rolling a two either."

"Okay, but..."

"And if you keep complaining, you won't get any more information about the dice roll and maybe everything above two has you wearing nipple clamps."

"Sorry."

"Sorry what?"

"Sorry mistress."

"Now think about what you're going to do."

Two was not a great outcome. But it did suggest that I would get an orgasm for anything that wasn't a one.

"Three is the same as two, but I'll spare you either the clamps or the pants," Cynthia said like she was trying to rhyme after another ten minutes.

And it didn't change much for me.

Ten minutes later without even looking up from her phone, "Four and you'll eat me out whilst you get yourself off."

That wasn't bad and it made me look forward to five and six, but it wasn't enough to change my mind about not rolling the dice by itself.

We were approaching the edge of our village when she told me about five. "A five gets one of my feet in your mouth and the other on your cock."

I did confirm that she would be rubbing me to get me off and not to torment and she made that wicked of smile of hers. She'd given me a chance at something I'd want and she'd knew it. And it was honestly tempting. A four was still good, maybe with some begging she wouldn't put the clamps on for a three and at least with two I'd still be getting off and she'd still enjoy my pain. But I wasn't actually sure what I was going to do, there was a still a chance I'd be waiting another three days. I don't even remember the last time I had gone a week without masturbating. I probably hadn't gone ten days without getting off since I started getting off.

We were pulling onto our street and I knew I had to make a decision in the next minute, but she hadn't told me what six was. It had to be good though right?

As we rounded the corner and home was in sight. Cynthia spoke up, "You get a six and I'll give you a handjob."

I almost choked and it was a good job I was slowing down to start parking. I might have caused an accident if I'd been going faster. That was a good one. Not only had Cynthia barely touched my cock so far, it had been well over a year since I'd gotten a handjob.

"So what are you going to do?" She asked as I was pulling into the driveway. I had seconds to decide.

"I'll roll the dice."

"Good choice."

I parked the car. Cynthia got her own bags and we pretended like we were normal siblings as we went back into the house. And then I waited. Conversations with our parents about how we were spent our day just filled some of the waiting. There was dinner and then finally our parents went for a walk and Cynthia grabbed me by the wrist and took me to her room.

She ordered me to take clothes my off and wait on my knees until she comes back. I had my clothes off and neatly folded in less than a minute and I waited at the foot of her bed facing the door.

About two minutes later she came back and was holding the box of Monopoly.

"Oh come on," I cried. For some reason, the monopoly dice were fucking awful to me. I joked about how some spirit I'd offended had possessed the dice to mess with me and had gotten stuck in there. I couldn't even roll seven when I needed to.

Cynthia just laughed. "You're going to roll one of the dice in this box."

I had a sinking feeling that I was going to roll a one, a two if I was lucky.

She handed me one of the dice and I looked up at her and put on a bit of a puppy dog face. "Can I at least roll both of them?"

She looked like was she considering it and I was hopeful. If I could take the best of two dice, I shouldn't end up rolling a one.

"It's an interesting idea," she said, "but not today. Now roll the dice."

I gave the dice a proper roll on the carpeted floor. Cynthia was a stickler for proper rolling when we were playing any game with dice, she would not stand for me trying to fudge this.

The dice went further than I intended and bounced lightly off her drawers. It stopped, but I couldn't see the dice well, so I looked up at Cynthia who was closer to it and she was smiling.

"Crawl over and take a look."

I quickly saw the three on the side of the dice, which meant it wasn't a three or four. So this was going to be very bad or very good. And Cynthia's smile told me it was the former. I was praying for the two and not the one and seconds later I was looking down at the dice.

It was a five.

It was almost enough for me to find god.

"Here," Cynthia said as she dropped the key on the floor between us. I realized I'd probably found god about a week ago and she was about to reward me for following her rules.

My hands were shaking as I put the key in, but I eventually managed it and pulled the cage off and it was like I could breathe again it felt so good to have it off. I didn't get to bask in that feeling long as I was ordered onto my back at the foot of Cynthia's bed.

I took my place and looked up at Cynthia who was sitting on the edge of her bed. She ran her toes over my stomach and chest silently and paying extra attention to where she'd left marks with her heels earlier.

"I wonder which one of us is about to have the most fun," she said rolling one of her feet around my already hard cock.

"I think I will."

"Open your mouth."

I did and she slid her small foot into my mouth. All five toes and then she started pressing down firmly on my cock with her foot.

"Kind of pathetic to have so much fun with your little sister's foot in your mouth."

I mumbled an unintelligible response through her toes.

"See. Is it really that fun not being able to talk?"

I grunted.

"My big brother having fun being my pathetic little bitch. This is the life."

I wanted to tell her happy I was to be her slave.

"I wonder how pathetic I can make you be for me," Cynthia mused, "maybe I can get you to cum in the cage one day."

That was hot but terrifying. How long would I be in the cage for that to happen? Would she ever let me out after she had proved she could do it?

She continued with the taunting and after a few minutes I was really leaking. "How many men leak this much for their little sister?" She pulled her foot up to show me and carried a thread of pre-cum a long way.

I wanted to tell her how perfect she was.

"Not many I think, but then there's a lot of words that describe you better than 'man' isn't there?"

I tried to nod.

"There's pathetic of course, but let's try some nouns. Bitch. Slave. Toy. Trash. Degenerate. Any objections?"

I didn't even grunt. She was right.

"I didn't think so," she said. I think she'd have said that even if I had tried to object.

Cynthia started rubbing me more firmly. Not quickly. But with a force that had me moaning loud enough to be understood through my foot gag. I was just praying she didn't stop as I reached the point of no return. Cynthia took her foot out of my mouth and then I exploded all over my stomach with some of it getting on her foot. I shook with my back arching off the floor more than once. Once I stopped shaking, I just lay there with a feeling of quiet contentment and nothing else. It was the best orgasm I'd ever had.

I eventually muttered, "thank you."

"You're welcome." She ran her foot through the cum on my stomach and spread it around. "You know your face was kind of cute just now."

"Thanks."

"Still pathetic, but kind of cute."

I just closed my eyes. That was amazing. And the two of us were just getting started really.

"Put the cage back on." Cynthia said. It wasn't delivered with the force of an order, but more like a request to do something trivial like a close a window you were sitting next to with the asker knowing it'll get done because it's such a normal thing to ask for.

And I did put it back on like it was the most normal thing in the world. Being in chastity. Being my little sister's slave was my new normal, so handing the key over again was natural. I wanted to be beneath her. She wanted me to beneath her. So I was beneath her. It was that simple.

"No cleaning yourself up until you shower tomorrow."

"Okay."

"It should be a good reminder of how dirty and pathetic you are."

"I'm only this dirty and pathetic for you mistress."

"For now," she smiled, "I'm not done with you yet."

"I'll be happy if you're never done with me."

"Now it's time for you to make me happy, there's no way I'm letting you leave this room without pleasing me," she slid back and removed her jeans and pants and ordered me to eat her out.

I obeyed.

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AnonymousAnonymous5 months ago

More please

AnonymousAnonymous8 months ago

This is my favourite type of fantasy, being dominated and completely humiliated by your little sister, the only shame is the story is quite short

AnonymousAnonymous9 months ago

Hate that this looks like end to this really great story..

lunarojalunaroja9 months ago

Great. Submitting to a much younger woman is such an erotic idea, made more intense by her being his sister, and her lovely scorn for him.

AnonymousAnonymous9 months ago

This is really hot story line. Really hope there will be more chapters to this story. The fact that his Dom is his younger sister is smoking hot. And it sounds like their slave master play is making her a happier person pulling her out of her funky Disposition. And I known her older brother is in heaven, and probably hoping she'll start using his cock one day then feed him his cream pie to eat..

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