The Unlucky Sissy

"Are you sure sissy?" he asked.

I nodded my head.

"You do realise that you could be trading five minutes of excitement and anticipation for a long, long period of frustration?" he continued.

"Yes sir." I replied.

"Very well then," he said with a smirk. "I've set the game up as you described. Come over here so that I can cage you and we'll begin."

I made my way over to him and lifted the hem of my leather mini skirt, I wasn't wearing underwear as he preferred me that way when I was at his house. He reached out and cupped my balls with one hand as he brought the metal chastity cage up to my groin. He eased my testicles through the locking ring before guiding my less than average sized manhood into the cage. Within a few seconds he had it lined up and locked closed with a small pink padlock, to which he held the only two keys. It was a custom made, high quality cage and lock, it could not be cut, lock picked or in anyway removed without the key.

"Come and sit at the table baby and we'll get started," he commanded.

I walked over to the table, my legs trembling with nerves and anticipation. He sat opposite and looked me in the eye as he reached out with his hand. I reached out my own hand to receive the contents, it was visibly shaking as I took the dice from him. This first roll was the most crucial of the first stage of the game as it would determine how many times I would roll it in the next stage. I closed my eyes and rolled the dice, I heard it bouncing and spinning on the surface of the table. I listened intently for any reaction from my master as it fell silent. There was no audible response, I opened my eyes to look at the dice and as I did so caught sight of the grin on masters face, I knew at that point it wasn't good news. I had, of course, rolled a six.

"Still think this is a good idea sweetie? Still no backing out now. Six rolls of the dice. I'll record the results," he said as he grinned at me.

I picked the dice up, swallowed hard and took a deep breath to compose myself. This was of course, potentially complete madness, but there were layers within this game, it was those impending layers and their subsequent consequences that so excited me. I gave the dice a shake and rolled it. A three, not bad, but not great either. Master noted the number as I rolled again, a six, bugger, not good at all. I made my third roll, hoping for an improvement, a one, phew that was a relief. The one had calmed me slightly as I rolled again, this time I got a five, master smiled as he added it to the list, my forth roll was another five. I gulped, i'd made five rolls and hit two fives and a six, if the law of averages was on my side, the last roll should be low, but would luck be on my side? I composed myself again and made the final roll, it was another one, i tried to hide my grin.

He spoke to me in a calm, measured voice, "Well sissy, that was interesting. You rolled 1,1,3,5,5 and 6. That really makes the next choice rather crucial doesn't it?"

He was right of course, but I'd been so focused on the dice rolling that I'd not allowed my mind to drift forwards to future stages of the game. Master held two envelopes, one in each hand. I knew that there was a single piece of paper in each and up each piece of paper there was a single word instruction. A simple 50/50 choice, but with wildly differing consequences. Which one should I choose? There was no way to distinguish between them, I reached out towards the lefthand envelope, my hand visibly shaking and my mouth dry, I maintained eye contact with my master. Just as my fingers began to close to take the envelope, I was sure I saw him start to smile, did he know which was which? I recalled reading something on the internet that said that when faced with such choices, you should change your mind, so I did and quickly grabbed the other envelope before my pounding heart popped out of my chest.

"You should open it baby, but let me see as it comes out." he instructed.

My hands were now shaking so much that I was waving the envelope as if it was a fan, both of my legs were shaking uncontrollably. The intensity of the feeling was exactly why i had wanted to play this game.

"I can't sir, please open it for me." I said to him.

He reached out and took the envelope from me. He slowly drew out the piece of paper and placed it face down on the table.

"Turn it over." he commanded.

I reached out and turned the paper over. Staring at me I saw the single word that I had been dreading.......

"MULTIPLY"

My heart sank, I scrambled to do the maths in my head, but my brain was mush and the number was going to be high, I was totally overwhelmed, what had I done? I was snapped out of it by the roaring, uncontrollable laughter of my master. I was suddenly very hot, I thought I might either pass out or vomit.

"Oh dear sissy, now those ones aren't looking so good are they?" my master said as his laughter subsided.

Of course it's not possible to multiply by one, so we had agreed that in the event of me selecting the multiply option, any ones would be counted as sixes. with hindsight this was a foolhardy decision made whilst horny from thinking about the game Id dreamed up. Yes, this was my game and my idea, I'd done this to myself.

"Lets see then sissy, I think this is going to be a big number i'm going to need my calculator. Six times six times six times five and times another five and finally times three is......... oh dear dear," he paused for dramatic effect. I couldn't look at him, "It is sixteen thousand, two hundred." he exclaimed dramatically

It couldn't be could it? My head swam and my stomach churned. If only l'd chosen the other envelope. The paper in that one said "ADD", that would have given me 21, but instead I'd got 16,200. I tried to calm myself, there was one final set of envelopes to choose from, if I got the right one, it would still be bad, but not as bad as I feared. My master had placed three new identical envelopes on the table. I just wanted to know, I needed to know, it had to be the right one. I snatched the middle envelope and ripped it open, I pulled the paper out and threw it on the table, my heart sank, it wasn't what I wanted, the one word this time said.......

"LOADS"

That was the worst one, I was going to have to take over 16,000 loads of cum before I would be freed from my cage.

"Well sissy you got a bit of luck at the end there." said my master, he was grinning like the Cheshire cat, he was absolutely thrilled with the outcome of the game.

"Really sir, luck would have been "HOURS" that's what I wanted." I replied.

"Well yes honey, that would have been the best for you," he replied as he tapped on his calculator, "You'd have been out in under two years. But you could have got "DAYS", that would have been", he hesitated as he he tapped on the calculator again, "44 years! You got seriously lucky there!" he explained to me.

"But sir, 16,200 loads sir." My bottom lip was trembling, I looked at him for sympathy maybe hoping he'd let me play again, or change the outcome, but I knew that he wouldn't. We'd discussed this up front and I'd signed an agreement to abide by the outcome.

He responded in his calm manner, "You're not thinking straight baby, but that's probably understandable, you're in shock i think. A few gangbangs will bring that number down quickly." He reached for his calculator again, before exclaiming, "Lets say 20 guys each weekend, with an average of 3 loads each, that would be just over five years, see much better than 44 years!"

He was right of course, I knew that before the month was out, I would be naked and on my knees with his big, hard cock in my mouth while I begged him to arrange gangbangs for me, with ever increasing numbers of men and ever increasing frequency to reduce my five year lock up period.