Boy's training was going very well. It's been 3 months and he seems to get better with each week that passes. More obedient, much better about knowing what to do at the right time. Like milking my cock with his pussy, without being told to. Lately he's even stopped asking on a daily basis if he can cum. For the past few weeks I've not let him cum except maybe twice to teach him it's not about his pleasure, it's about mine, then maybe his, maybe. I was quite pleased with him and how things were going.
One Wednesday afternoon I decided to take the afternoon off and do whatever I felt like doing. So my first stop was home to change and then decide what I wanted to do. I see boy's car in his driveway so I go over and see what's up. I use my key to let myself in and before I call his name I hear his voice. So I follow his voice and he's saying, "Please sir, fuck me. I'm such a good cocksucker, aren't I? Do I have the sweetest, tightest pussy, Sir?" I'm shocked and not sure what to think. So I walk slowly into the bedroom expecting to find someone fucking my boy, without my permission, but boy is facing away from me on all fours and on the bed. He's got a dildo in his pussy and he's fucking himself saying, "Please Sir, please, please let me cum. I'll a good boy, Sir. Please, Sir?"
He has no idea he's being watched so I walk up behind and grab the dildo, yank it out of his pussy. "Turn over on your back and spread your legs, now!" I holler at him. He's so stunned he doesn't know what to do and then starts pleading with me. "Sir, I'm sorry, " over and over he repeats himself. "Shut up and do as your told. You want to cum so bad, so let's make it happen," I tell him. Then I start fucking his pussy hard and rough with the dildo. "Take your little boy dick in your hand and get off," I say. He doesn't know what to do but he does and looks very happy. It doesn't take him but 2 minutes or less to blow and he does with force. All over his chest and a couple of splashes on his lips and he's writhing in ecstasy. I let him clean himself by scooping it all up with his fingers and sucking it all into his mouth. "Now go take a shower," I say to him and off he goes and kisses me before he leaves.
While he's showering I go on-line to find a chastity belt for boy. After searching and then finally deciding on the best one for him he walks in the room and I tell him to sit on my lap. "You have been a very bad boy today so you'll have to be punished. And I have to be assured that this will not happen again. Right now I can't trust and to help regain your trust you'll be wearing this," I explain and the point to the computer screen. He asks what it is and I tell him and he doesn't look pleased at all. I tell him he's paying for it as well and off he goes to get a credit card. I don't hear another question out of him that night.
There was a box waiting on his porch 2 days later so when I got home I went to his house, grabbed the box and waited inside until boy arrived. I had it opened and ready for him when he walked in the door. After kissing hello I told him to strip and his dick was rock hard. "Well we'll have to get rid of that," I smile at him and he doesn't respond just kind of looks at me like how are we going to do that. So I slap his balls real hard but that just makes him leak precum and yell. So I take him to the kitchen, get some ice and we're off to the bathroom. I have him get in the tub, had him the ice and tell him to lose the hard on and quickly. Once he was soft, on went the chastity belt, CB2000. He looked really hot in it and then I thought he needs to know just how it's going to be until I take it off. I start twisting and pulling his beautifully large nipples, which always gets him hard. Then I start playing with his pussy, just teasing him, not really entering him. And finally I slap his balls a few times. "Get the idea boy?" I ask him.
That night before bed I placed a good sized butt plug into his pussy and told him he'd be sleeping with it. During the night every now and then I hear him try to get comfortable and I'd slap his ass and tell him to be still. When I woke he was already awake and waiting for me. I asked him he slept and he said not very well. He looked so sleepy with his red eyes but I explained to him why he's in this situation. He said thank you and I told him to make breakfast. After that I told him to get ready for work and pulled the plug from him and left.
He wore the CB2000 for 2 weeks without it being removed. While he still wasn't used to it he had stopped whining about it. Since he's been good I think I'll let him cum in a day or two. During his CB200 wearing days I've had my cock in him more than usual. I even had a couple of friends over to use him, which I don't normally do anymore. He told me yesterday how he craves my cum even more now. So this thing is working, doing just what I wanted it to do.
Two days pass and I decide he's getting one more long hard fuck before I let his dick free. All evening long I played with his pussy, with my fingers, with dildos, with my tongue, I had him moaning and whimpering. I finally decide to fuck him with my cock but before I do I tell him I'm taking the belt off and he can cum while I fuck him. He's so happy he starts crying so I hold him for a while then lay him on his back and tell him to show me his pretty pussy, which he does with a big smile. "Thank you Sir, thank you Sir so much," he says over and over. "You can't use your hands, the only way you're cumming will be by my fucking you," I tell him harshly. I place my cock at his pussy's entrance and slowly slide into him. I had fucked him for maybe 5 minutes when he lets me know that he's about to cum. I just keep fucking him and his cums shoots up in the air then all over his chest, even his nipples were coated. He's breathing heavily and loving every second and I still haven't stopped but just seeing him brought me over the edge. I pull out and aim my cock at his face, he opens his mouth I blast off. On his face, in his mouth and he looked so good covered in my cum.
After he finished licking himself and me clean, I ask him if he's going to be a good boy and he just looks at me and smiles. The I put the CB2000 back on him and he looks sad. "You'll be wearing this until I say otherwise," I let him know and slap his balls. "Thank you, Sir," he replies. I pinch his nipples and tell him to get up. I had him explain to me why he was home early and asked him if he masturbated any other time since he's been my boy. He said he had but just a few times. I asked him when and where he had played with his little boy dick. Once in the bathroom at work, once in his car, twice in the shower before work and he assured me those were the only times. "Looks like this chastity belt was bought at the right time. You need to learn to control yourself. You know your position being a sub and that's to pleasure me first then possibly yourself. Part of your punishment will be to wear it longer than I originally thought you would and I'll let you know the other part later," I said and let him know how disappointed I am in him. He hung his head and cried. I left him there crying as I walked to the kitchen for some water.
He came out after showering and again let me know how sorry he was. I told him to prepare some dinner for us while I turned on the TV to watch the news.I must have fallen asleep because the next thing I know he's waking me and letting me know the food's ready. We converse while we talk, after we're through he clears the dishes and I go back to the TV to relax. While he's cleaning dinner I yell to him that he looks thirsty and he should meet me in the bathroom. I make him wait a few minutes and go in, unzip, put the head of my cock in his mouth and let go as he eagerly drinks it down. I ruffle his hair when I'm through and walk out as he thanks me. I tell him to get the kitchen done and then find me.
When he finds me I've got some new things laid out on the coffee table. A new longer ball stretcher, a ball divider, a ball gag, and a collar. I tell him to stand in front of me and place the ball stretcher on him and he lets me know it hurts. "You let me know if it's too much in a few minutes," is all I say to him. "Now kneel here and take my cock out and nurse on it until I say otherwise," as I settle in to watch a movie.