So this one has taken a long time to get done. Life kind of ambushed with me demands on my time that had to be put first. Most of that is over now, but even if it isn't, I am generally someone that finishes what they start. The finale begins in the next chapter and I hope to have this story finished by the end of the year.
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I'd been my sister's slave for about a month now and we had mostly settled into a routine. We knew what days and what times she could take her time with me and when we only had time for me to get on my knees and eat her out.
Since Cynthia had stepped all over me in a range of shoes and gotten me off with one of her feet. We hadn't really done anything new. I did spend a bit of time every week - usually Wednesday - being used as a foot stool and she continued to talk about her plans to use the nipple clamps on me whilst I was down on my knees.
I was happy with the way things were going and Cynthia seemed to be really happy too. It had been almost a week since my last orgasm, but before that I'd gotten two a week and she'd repeated having one foot in my mouth and one on my cock for two of the occasions and I didn't even have to roll dice for that to happen.
But now my devilish little sister's next game was afoot. She was standing in front of me holding an envelope that had "for my pathetic big brother," written on the front in her fancy handwriting.
"You can't open this until we're alone tomorrow, but it's important that you have it now," she explained.
"Why?"
"Because I want you to be certain that your performance tonight matters."
"Is this about bowling?" I asked incredulously.
"Yes. Our parents will be out most of tomorrow and what we do tomorrow does not depend on the roll of a dice, but how well you do at bowling."
"I see. And are you going to be unlocking me to go bowling."
"Of course not."
"That's going to make it harder."
"Is it? Is it really?" She smirked. She was not talking about making bowling harder.
"You're pretty consistent, so I want something that'll make you feel like you're in danger."
"But I don't know what's in the envelope..."
"You don't have to know everything yet, but I will tell you a few things," she smiled and sat down on my desk chair and twirled the envelope around in her fingers. "If you average 150 or less or somehow don't make a hundred in any game, I'm going to torment you and make you wait at least a few more days before letting you out."
"That shouldn't be a problem," it had been like five years since I'd scored less than a hundred and I was drunk at the time, and I'd still scraped a 150 average.
"Things get better for you every 10 points your average goes up and just to make sure you're motivated, you'll get that kiss you want if you average 200 or better."
And suddenly I was more excited for bowling since... I don't remember when. Since I got my own balls?
She went on to explain that I'd be punished in some way for any gutter balls and open frames I had which definitely meant I'd be getting punished tomorrow. I could bowl a clean game, but over three games I'd probably have three or four opens.
I put the envelope in my desk drawer and waited excitedly for us to leave. I was worried that the cage would trip me up and stop me getting a 200 average which was pretty common for me, but by no means a guarantee.
Before I knew I was at the alley staring down the first set of pins, I threw the ball to leave only the 10 pin standing which I easily picked up. I flashed a quick smile at Cynthia. At the start of the second frame though, my cage caught my skin as I was stepping forward and I let the ball go and it almost took a single pin, but it fell into the gutter at the last moment. I turned around and now Cynthia was smiling wickedly. Right. She was going to enjoy punishing me for that.
I finished game one with a score of 179 me in third place behind both my father and Cynthia. It had been messy game and the cage was seriously threatening my ability to string strikes together.
Whilst my parents were getting drinks between games Cynthia sat next to me and said, "better get it together," then she leaned in, "an average under 180 gets you the clamps."
That was more motivation to play better, but it didn't change my goal. I was aiming for 200 and a kiss, not to avoid nipple clamps, but that would be a consolation prize.
Game two did go better and I scored 205, but that still left me needing 216 in the last game. And in the last frame of game three it came down needing a strike and a spare. I got the strike, but was then foiled by a 7-10 split. I did get one of them, but it wasn't enough and I finished with 215 and a series total of 599. 1 short.
"Damn."
"You still won," my father said, "how about some pool?"
"I'd rather do another couple of games of bowling," Cynthia said flashing me a smile.
"Well your mother and I will be playing pool. Son?"
"No point in three of us trying to play pool and leaving Cynthia on her own, I'll bowl."
And then our parents left me and my sister alone on the lane.
"So, can I still try for that 200 average?"
"Yes."
"Thanks."
"But you should try your best not to throw any gutter balls or leave any more open frames. The penalties were based on us playing only three games."
I did go on to leave some open frames during the next two games but I did finish with an average of 202 and feeling pretty satisfied with myself when it was time to go home.
Going to sleep that night was rough. There was a mix of excitement and anticipation because I knew something good was going to happen tomorrow, but there was a lot I didn't know. And there was a bit of worry too - there were enough gutters and open frames over five games that I was probably in for a punishing experience too. All the excitement had me straining in my cage too and it took a while for me to calm down enough to get some sleep.
I did wake up straining in my cage and immediately decided to get things done starting with a cold shower. I wanted to get everything I could done before our parents went out so my sister could have her way with me for as long as possible. I had everything done with an hour to spare and I'd even put dinner in the slow cooker and put some chicken breast in to marinade for lunch. I didn't see Cynthia whilst I was cleaning, but basically all of her chores were already done.
Our parents told me they were going out and to make sure Cynthia gets up before noon and before the car was even out of the driveway I had a message from Cynthia.
-Go to your room and kneel naked on the floor in front of your door with the envelope in your hands, but do not open it yet. -
I did as I was told and knelt on my bedroom for what felt like an eternity but I could see my clock and it had only been ten minutes by the time my door opened and Cynthia was standing there looking incredible.
She was wearing the red lingerie from a couple of weeks back and only that. Her feet and legs were bare as were homes and for the most part her shoulders were too. The red lingerie was a couple of shades lighter than the deep wine red of Cynthia's lipstick and nails and it hugged her hips and flattered her breasts.
"Close your mouth, you look stupid."
"You look like a goddess." It sounded cheesy, but I wasn't lying.
"Duh. I am. And as your goddess, shouldn't you be a bit closer to the floor?"
I lowered my head all the way the carpeted floor and she put her foot on the back of my head and rubbed it firmly.
"Would you like to find out your fate?"
"Yes."
She moved her foot from my head. "Then open the envelope."
I leaned back on my heels, but was still on my knees with Cynthia looming above me as I opened the envelope. My eyes wandered straight to the top of the paper where for scoring a 300 - something I still hadn't done - it said we'd have sex and I just stared at that for a while. I wouldn't hesitate to have sex with Cynthia, but I hadn't thought for a moment it was something that was really on the cards. And maybe it wasn't, there was no way I'd have a gotten a 300 with the cage on and she knew knew that, but what could have been was going to torment me for days if not weeks and that was probably what she wanted.
My eyes went to the bottom after that, detailing being abused for the next few hours by nipple clamps, trampling and a riding crop and not being allowed a release for up to another week. And I was confident Cynthia considered that a real option and would have enjoyed it.
What the extreme scores had in common was that she'd be wearing white lingerie. So maybe I'd have gotten to fuck her like she was my girlfriend if I'd gotten a perfect game. If I'd scored badly, I would have definitely been tormented by the fact I couldn't.
And true to her word, scoring over 180 spared me the clamps and scoring over 200 won me a kiss. Higher scores than I'd gotten would've spared me her shoving her feet into my mouth - not sure that was a bad thing - and would've won me multiple orgasms.
"We'll be starting with the punishments for your open frames and gutter ball."
I'd forgotten about that and looked for that section. She was going to slap me once for every open frame and trample me for a minute for every gutter ball. I'd only left seven opens in five games and she wasn't wearing any shoes, it wasn't going to be that bad.
"Are you ready?" She smiled.
"What happens if I say no?"
"The same thing that happens if you say yes."
