The Will of the Dice

Submitted by: Davidphys

  • This story is an adaptation of "Wish Me Luck" with permission of the original author.

Tim released me from my chastity cage and began to jerk me off.  After not cumming for a week and a half, I desperately wanted to shoot my load.  I was almost there, moments away for cumming, when Tim slapped me in the balls - hard.  I cried out through my gag and fought against my bonds.

Finally, when Tim had had enough - a blowjob, a fuck, and my lengthy torment - he let me cum.  Sadly for me, he stopped rubbing just as I was about to cum. I was left on the bed, unfulfilled, in the ropes overnight with Tim by my side, cuddling me.

*    *    *

Tim was a close friend of mine; he was my fuckbuddy and part time dom.  He loved making me cry out in pain just as much as watching me silently suffer.  Of course, I did suffer when I was locked away for days or weeks in my chastity cage.

The day after my release and torture, my cock was free and I went over to Tim's place to have some good old fun ending, this time, with a pleasant orgasm.  While Tim might torment me when we were doing BDSM, he would give me unrelenting pleasure when we otherwise met.

Afterwards, Tim asked me about progressing with our chastity play. "How about we take your interested up to a higher level?"

"What do you mean?" I asked.

"We'd talked about doing longer periods in the cage before.  I think it would be fun to try a little game.  We could roll some dice to see how long you would be kept in chastity.  That way we could possibly get into long term chastity, but with the added benefit of uncertainty"

I was anxious at not knowing how long I would be kept locked for but I found it highly erotic. I wanted to be left wondering when my next orgasm would be.  I said yes.

"Alright," Tim said, "tomorrow I'll lock you up and then flip a coin.  If it lands on head, you'll be locked away for weeks, tails and you'll get months. Then you get to roll two dice.  The number you get will determine how many weeks of months you will be in chastity.  Oh, and you have to roll an odd number to cum. If you get an even number, at the end of the time period you'll have to roll again.  This time, the coin will be more important: heads means months, tails means years."

The idea of not knowing if I'd get to touch my dick for for years made stand right up. I was looking at anything from three weeks to decades without cumming and not knowing which. If I had simply reach down and given myself a few tugs, I would have blown right then.  I began to rub my hard cock against him but he said to save it for the morning.  I lay in bed with Tim that night with a perpetual hard on.

*    *    *

I woke up the next morning due to a funny sensation in my groin.  I tried to sit up but my hands were tied down to the bed, keeping me flat on my back.  Tim was shaving my groin of all of its hair.  When he finished, he wiped me off and said we'll shave the rest later.  Tim then straddled my face and shoved his dick into my mouth.  He fucked my face for a good fifteen minutes before squirting his juices into my throat.  I cleaned of the lovely cock before its owner left the room with me still tied down.  A few moments later, Tim came back holding some bags of ice that he packed around my cock.

"I'm sorry, John, but you won't get to cum for at least three weeks."  He gave a chuckle.

I was devastated, but Tim's ruthlessness made my cock stay harder for long than it otherwise would have when packed in an igloo.  When my dick shrunk to the size of a young boy's, Tim pulled off the ice packs and slipped on my chastity cage.  He locked it up and put away the key.  Until I rolled the right number, I was locked away from my favorite toy.

Tim untied my restraints and said, "Now, take the shaving cream and razor, go to the shower, and remove everything besides the hair on your head.  I don't see any reason to accompany you now have nothing to distract yourself with."  Again, he cruelly laughed but still gave me a friendly smile.

In the shower, I lathered up and began shaving everything off.  My armpits, my legs, my ass, everything was as smooth as before I hit puberty.  I toweled off and walked to meet my fate.

Tim handed me two dice.  "It'll be more fun if we wait on the coin.  That way, if you roll a twelve you won't know if you'll be stuck in that contraption for twelve weeks or twelve months," he said, still smiling.

I took the dice and gave them a good roll, right across the floor. The first die was a one but I couldn't see the other - it was under the bed.

"That's a re-roll.  You need to see the dice when they land."  Tim reached under the bed and brought out the hidden die.  "What a shame," he showed me the face up side - there were two pips.

I rolled again, but luck was not with me as I got a four and a six. Luckily, when I flipped the coin, it landed heads up.

"Ten weeks then," I said.

"Maybe ten weeks, but maybe twelve years, my boy," Tim corrected.  He grabbed me and sat me down on his well-lubricated cock.

*    *    *

The ten weeks passed quickly.  I reached peak frustration at a month and stayed just as horny for the remaining weeks.  Every month Tim would tie me up and unlock my dick.  He cleaned it well and shaved any hairs that I couldn't easily get to with the cage on.  He would end the session by sticking his finger up my ass and milking my prostate dry.  He'd often milk me throughout the month, just to ensure I didn't come from when he fucked my ass.  Tim made sure I served my full time.  At this point, he'd accept nothing less than the ten weeks plus three month minimum.

"Heads months, tails years," Tim said as he handed me the coin on the day of the decision.  I smiled nervously.

I had decided to start with the coin; I couldn't bear not knowing whether a twelve would mean one year or a dozen years.  I flipped the coin, caught it, turned it over onto my arm, and revealed that I got tails.  At best I would be locked away for another 156 weeks.

Tim and I decided in the previous weeks that if I rolled an even number that next time the coin would not be used and years would be assumed.  I took the dice from Tim and cast them clean across the room.  A six. I would spend no less that nine more years of chastity.  I felt mildly sick but Tim was rock hard.  He fucked my ass raw.

*    *    *

Six years later and I'm still kept as smooth as I was when I was nine years old.  Smoother, in fact, as I now have my head shaved as a sign of submission to Tim.  I hadn't cum since I was twenty-three and without any prospects of ejaculating for nearly a decade we formalized our relationship.. Now Tim keeps me as his slave.  So much for being fuckbuddies and so much for pleasuring me during sex.

Tim also has a new friend: Mike.  He too is into chastity and signed up for the same game that I did.  The bastard is nearing the end of his five-week chastity.

Tim and I decided to use the coin after all.  Heads this time will mean years and tails will mean even worse: I loose my cock for good.  If luck is not with me on this, Tim and Mike will cut of my penis and I'll never get to use it to cum again.  We decided this was more practical than a lifetime in my cage.  To make matter even worse, I had to roll an odd number, an even number would mean that I would have to roll again but the coin would have to be increased so that at a minimum I would still loose my cock in the end.  Therefore, we decided that if I rolled an even, I would loose my cock then and there - no point in waiting.  I only had a one in four chance of ever using my dick again.

Tim and Mike tied me up good and tight before we started.  Everything was ready in the event that I failed to roll correctly.  My legs were spread wide open and I was gagged and blindfolded.  I would not know what I rolled until Tim either gave me the coin or cut off my cock.

With my chastity cage off for easy access, Mike gave me what might be my last hard on.  Tim placed the dice in my hand.  I could barely throw because of the restraints and the dice mostly fell to the floor.  I heard them hit.  Mike stopped rubbing me.  I braced for the worst.

Tim placed the coin in my hand.  He didn't say the number but I knew that I might get to cum again.  I breathed easy and tossed the coin just as feebly as the dice.

Within moments I felt my dick being severed.  I screamed into the gag. I got no anesthetics and the pain was intense.  I quickly passed out.

I woke up minutes later with my legs untied and above my head.  I now had I mere piss hole just above my sack where my penis once sat.  My ass was being pounded by who I later learned was Mike.  He had made a deal with Tim that he would get to fuck me but in return he would have to re-roll for another period of chastity, this time starting with a minimum of months.  He came to regret this decision four years later.

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