Chastity with Steve Pt. 05

Steve had been locked up for some time now. It had been his idea originally, but I have really begun to enjoyed it and have run with it. I have made it a point to push the limits with him in an effort to see how far I could take it. So far, I had pushed him a bit, but had not really gone as far as I could. When Steve got up, I gave him a very long list of chores to do around the house. He had gotten very good at doing what I wanted him to do. This was usually his key to a release.

Doing chores was a good first step, but I wanted more. I decided that I needed him to work harder for his next release. Steve was toiling away at his chores as fast as he could. He was sure that a release would happen, if he made the things on the list disappear. While he was doing his work, I made alternate plans. I got on the internet and put the words "random number generator" in the search engine. A few things popped up but one caught my eye. It was called the wheel of misfortune. It was specifically designed for women that had their men in chastity. I read the site and discovered that the wheel was not really random. There were a hundred different results that the wheel would produce. They ranged from one day between releases up to 365 days. Most of the results were skewed to the high end. I spun the wheel a couple of times to see how it worked. The first result said he would be locked up for seven days, the next said sixty days. I was beginning to like this.

A current user noted in the remarks that they spun the wheel twice. The first number, was how many days before release, the second result was how many orgasms the keyholder got to have before release day. If the man did not achieve, bring the keyholder to the orgasm goal, then he would stay locked for another period equal to the first period. I got wet just reading this. This was the perfect game for Steve. This was going to drive him nuts. I left the computer open on the site and waited for Steve to finish his work.

Steve finished his work at around 5 pm. He bounded into the kitchen and stood in front of me with an expectant smile. I reached down and jiggled his cage and asked him if he was ready to play. He responded loudly, with a yes. Steve expected me to get his key. Instead, I turned the computer so he could see it and explained the new game. Steve read the information on the site. His entire body drooped as he realized what he was about to sign up for. I told him that he had no choice. Then I told him that his release date was now up to him. He now needed to press the button to choose a release date. He pressed the touch screen and the wheel spun quickly, then it gradually slowed down. The wheels speed slowly decreased to the point where he could see the numbers going by. He saw 365 days, thirty days, sixty days. Steve was losing his mind, hoping that he would get lucky and hit one day.

Finally, the wheel stopped on twenty-one days. Steve's response was one word. FUCK! I laughed and told him that this was the first number, he still needed to spin for the number of orgasms he needed to give me. Steve pressed the screen again. The wheel spun rapidly then slowed to a crawl and stopped. Thirty was the result. Steve needed to give me thirty orgasms in twenty-one days. Wow, I thought, that's more than one per day. I had never had more than one a day, so this was going to be fun.

I looked at Steve and told him that he had better get busy, if he was going to meet his goal. Steve quickly approached me, dropped to his knees and pulled down my sweat pants. Next, my underwear slid down to my ankles. Steve then buried his tongue into my very wet pussy and began to work on my clit. I giggled. He definitely knew what needed to be done and got right to it. I put one hand on his head and the other on the kitchen counter to steady myself. Steve tried his hardest and made quick work of it. I had a nice orgasm all over his mouth. Once I caught my breath, I looked down and told him that this was number one and he had twenty-nine more to go.

Steve buried his mouth back into my pussy and went for number two. I pushed him away and told him that he had to wait, he wasn't going to get thirty in one night. He groaned and made a sad face. He asked me when he could give me another. I told him that he would know, when the time was right. The rest of the evening, I purposely wore some short shorts, that show my ass off. His eyes never left my body all evening. Just before bed, he was watching the game on TV. I stood in front of him, blocking the TV. He asked me to move out of the way. I pointed at my crotch and asked him if he really wanted me to move. Like a flash, my shorts were at my ankles. Steve's mouth was working its magic on my clit a second time. The second orgasm took a bit longer. Steve really worked hard, but was able to pull off another successful orgasm. I was really enjoying this new game.

Steve's mouth worked overtime for almost two weeks. He had pulled off a remarkable twenty orgasms in fourteen days. He now had to accomplish ten more in seven days. I was not going to make it easy on him. On day fifteen, I told him that my pussy was off limits to his mouth and the next ten orgasms had to be done some other way. Steve went out and purchased a vibrator from a local sex shop and brought it home. I laughed. He bought one that plugged into the wall. He said he wanted to be sure it was strong enough to get me off. He certainly was working hard for his release. Steve laid me down and buzzed my clit. Damn, that thing was like a jack hammer and I came in less than a minute.

I opened my eyes and looked at him. He was proud of himself for giving me an orgasm that fast. Steve looked like a conquering hero. His new toy might screw up my plan, I thought. I wanted this to be tough for him, but that vibrator was going to make it too easy. Sadly, it felt so good and worked so well, I didn't want him to stop using it. Over the next few days, his toy worked its magic quite a few times. That little shit was going to get his release. Steve was only one orgasm away when we hit day twenty-one. I made it a point to try to stay away from him all day. He chased after me like a bloodhound all day. He finally caught me around 6 pm. He told me that he had worked hard and he wanted to finish his duties and get his reward.

He got to his knees and plugged in his magic wand. He pulled down my pants. To his and my surprise, I had started my period. My underwear had blood on it. I pulled them up and ran to the bathroom. Steve just stayed there on his knees, totally dejected. I cleaned up and put in a tampon. I came out of the bathroom and found Steve laying on the floor in the fetal position. I had never seen his so depressed. I told him that he waited too long and that next time he needed to plan better. He was so upset, he couldn't speak. I felt bad. Steve really had worked hard. However, if I gave in now and unlocked him, he would never learn his lesson. I decided that I was at least going to play with him a bit. I told him to get back on his knees. He knelt in front of me and I got on my knees too, eye to eye. I reached down and picked up his vibrating friend. I told Steve that he had to look into my eyes. If he looked away, I would stop whatever I was doing. He agreed. I took my other hand and grabbed his caged cock. I turned on the vibrator and put it on the high setting and placed it on the cage.

Steve's eyes rolled back in his head. I reminded him to look into my eyes. The vibrator buzzed loudly and made the metal cage rattle. I asked him who he loved. He said that he loved me. I asked him how much. He said that he loved me more than I could imagine. I told him that if he did, he needed to prove it. I wanted him to cum quickly and cum in his cage. I worked the vibrator around the end of the cage, then touched his balls with the tip. He began to shake. I told him to cum, cum right now. His body stiffen and my hand became wet. He continued to shake and my hand got wetter. I looked down. Steve had produced an impressive amount of ejaculate. I released my hand from his cage. His sperm drooled out of the tip of his cage onto the kitchen floor. I took my cummy hand and rubbed it all over his face and mouth. Steve, continued to shiver. His body was producing cum, but poor Steve was not getting any pleasure from it. He was on the very edge but could not go over. The perfect ruined orgasm.

Once his fluids stopped dripping from his cage, I pushed his head down into the puddle and told him to clean up his mess. He seemed to be in a trance and bent over without saying anything. I watched as he slurped up his wasted seed. I actually wanted to play with myself, it was so erotic. His downfall was making me horny. Once he was finished slurping up his mess. I told him that the clock has restarted again, twenty-one days and thirty orgasms. Steve fell to the floor and assumed the fetal again.