We had experimented with chastity before. Tim wasn’t my Sir, more like a close friend and part time Sir. When we played I was defiantly the boy. He knew about my strong interest in long term chastity, and had kept me locked for as long as a month in an access denied belt we split the expense on a year earlier.
One night we were out at dinner and he asked, “How would you like to take this interest of yours to a higher level?”
“What do you mean?” I asked.
“We had talked about doing a longer period in chastity before, but I don’t think a set time would mean as much as some uncertainty. Would you be willing to spend a considerably longer period in chastity?”
“Yes,” I answered. “What do you have in mind?”
He smiled and began to share his idea. “First well lock you up, then two factors will determine the length of time you will be in chastity. First, we will flip a coin. Heads means weeks, tails means months. After the coin flip you will roll two dice. The number you get will determine the number of weeks or months you will be in chastity. As an added bonus, if you roll an even number you will have to repeat this process at the end of your sentence. Should this second re-roll occur the heads and tales will up the anti. Heads means months, tales means years.”
He grinned ear to ear and I was hard as a rock.
“So you’d be looking at a minimum of 3 weeks and if you roll an even number possible decades in chastity. What do you think?”
“Wow,” I responded. “That’s pretty intense. We’ve never done anything like this before.”
“Are you willing to do it?”
“Yes, I’ll probably regret it but yes.”
“Good tonight I’ll restrain you, shave you, jack you off possibly for the last time and then lock you up.”
We finished dinner and went to his house. I was so horny I couldn’t stand it. We did as he said. He kept me on edge for hours before finally letting me cum. After that he cleaned me up and put on the belt. He removed the restraints and I sat up. He put a coin and two dice in front of me.
“You can roll the dice first, then flip the coin if you wish. Rolling a 12 would probably be more exciting if you didn’t know if that meant 12 weeks or 12 months.”
I liked this suggestion, so I rolled the dice first. I got a 10. I flipped the coin and got a heads. “So, 10 weeks,” I said.
“Well a possible 10 weeks, 12 years are ahead of you my boy.”
I was so horny that I wanted out right then and there, but I had to settle on sucking Tim off and letting him fuck me.
Those ten weeks passed quickly, I reached my sexual frustration peak around a month and stayed at that level for the next six weeks. Tim restrained and hooded me once a month to remove the belt for a cleaning. He was very careful not to let me cum. I was tempted to thrust my pelvis at him trying to make an accident happen. In the end I am a good boy and adhered to the rules of chastity, I wouldn’t be cumming for at least three more months, and possibly many years.
On the night of the decision Tim cleaned me as he had before and locked me up again. Handed me the coin and dice again and smiled.
“Heads means months and tales means years remember.”
I smiled a little nervous. This time I started with the coin. I couldn’t bear not knowing if a 12 meant a year or 12 years. I flipped, and the coin landed tales up. My pulse raced. At best I could hope for a three. Tim and I decided that if I rolled an even on a tales then the coin would not be used on my next re-roll and years would be assumed. I rolled the dice, my hands were shaking with anticipation. They landed on six. My fate was sealed, I would be spending a minimum of 9 years in chastity. I wasn’t feeling too horny after that, but Tim was rock hard and took the opportunity to fuck me raw.
Two years went by. I can’t say I love it, but I’m not miserable. I’d still say Tim and I amount to fuck buddies, but we’re close enough that I don’t feel like I’m missing a relationship. I miss sex, as one would expect, but I know that I have at least 7 more years to go. I’ll be 32 by the time this may end. Tim and I have talked and decided to use a coin after all. Heads will mean years, and tales will provide me with a choice: life in chastity or total removal of my cock and balls. I had already been intrigued with castration, it’s what led me down the road to chastity, and surgical removal of my cock and balls would mean I would be in chastity for life but without a belt to get in the way. Who knows what I’ll decide? I’m resigned to knowing that it is unlikely that I’ll roll a 3 with a heads. I have a 50% chance of never using my cock again and a 1/24 chance of only have to endure 3 additional years. Wish me luck.