This is the fourth of eight new video sessions from our recent Sissy Cuck Boot Camp Training at a local hotel! I made cucky book us the King Whirlpool suite, so I would have plenty of space and options for the brutal training I had planned.My Sissy Bitch had been begging like the little wimp he is to let him cum, so I said yes. He was so excited when I told him to put on his new pink frilly sissy outfit and lay back on the bed. He was surely wondering if I was going to fuck him to an orgasm? Maybe suck him till he came? He certainly do did not expect what was about to happen to him! I started out slowly and skillfully blowing him. I could tell he was so close to cumming, as it had been a very long time since I last allowed him to spill his sissy seed. But then I switched things up and climbed between his legs and stroked his little pecker, and he was yet again writhing in agony, needing the release I had promised him.Next came his first surprise. I rolled a condom onto his cocklette and continued stroking him, and telling him that he had better enjoy this, as it may be months before he gets to cum again, and I will definitely fuck many other men before he gets to release the next time. He agreed to that. I also told him he will go into permanent 24/7 chastity immediately after cumming. He again agreed. At this point I could have gotten him to agree to anything. If one of my boyfriends were there, I could have made sissy suck him off, but unfortunately that wasn't the case.Then Sissy started breathing heavily and moaning, and he completely filled the condom with a huge sticky load. Now his testosterone level had plummeted, and it probably occurred to him all of the things I got him to agree to when he was desperate to cum. He seemed content. And then I did something I had never done to him before. I pulled off his slimy cum-filled condom, climbed up onto his chest, and said "Open wide bitch!", and emptied the entire load of cum into his mouth, even squeezing it like a tube of toothpaste to get every drop out. I didn't have to order him to swallow, as he knew what to do!We sincerely hope you enjoy! Kisses, SoccerMomMistress.