Chastity and orgasm denial discussion

My Locked Boy and I enjoyed a fantastic evening. I went to mess with him, making promises not to touch his backside but just tease it. Eventually, I secured him to our bed using four-point restraints, fitted him with a ball gag, and looped the leash from around his cage base ring up through his gag strap before clipping it back to the cage; this kept his head held high unless he chose to let his balls get tugged. While handling him, I decided to be mischievous and toy with his rear after all, despite my earlier promise. First came a curved glass dildo we own, followed by a larger silicone one of similar shape. I managed to coax out several thick drops of cum while he remained caged, so I opted to uncage him and try ruining his climax—a feat I hadn’t pulled off before…or at least not like this! Let’s just say I succeeded in doing it three consecutive times! It was incredibly diabolically satisfying watching the semen ooze out rather than shoot forth. He described it as a terrible, unfulfilling sensation! Afterward, I released him from the bed restraints and immediately secured his hands behind his back with handcuffs inside the shower. I shaved him and managed to put his Jailbird cage on by myself—an achievement in itself since I lack experience doing so alone. Needless to say, I feel quite accomplished while he drifts in an exhausted haze. Several firsts occurred that night: 1. Prostate milking; 2. Three ruined orgasms; 3. He was uncaged and I avoided putting my mouth or pussy directly on his cock; 4. Shaving and re-caging him without any assistance at all…by the end, he remarked, “Oh, shit…now I really won’t ever be able to touch my dick again.” Overall, a very good night. Now I wait for his return from the store with our late-night snacks!