For the sake of the story, we will say that I was unable to achieve the ruined orgasm in the time allowed and was put back in the cage. Mistress ordered me to dress and handed me her large dildo and told me to bring her to the usual two orgasms. Once I had finished making her scream in pleasure, she ordered me to clean her up. “how does it feel to have your mouth in a well used, stretched pussy.” I just nodded and continued licking her pussy which was more stretched than I had ever seen after the two days of large cock. Once complete cleaning her up, she got dressed and we headed out for the day. When we were out she asked me why I thought she had chosen the large cock all week. I told her I wasn’t sure, and she informed me that it was because she truly did like being fucked by a real big cock now and even though I was ok sized, she needed much more. She also added that if I was lucky enough to get in her this week, it wouldn’t do anything for her so she would not feel as if she missed my pathetic cock the next go around. That night, I fucked her again, same as always, big cock, two orgasms, clean her up afterwards, all the while being degraded.
The next morning she offered me the same deal as the day before. This time however, I succeeded in milking myself on her belly and with only a little hesitation cleaned up my mess. She left the cage off and had me fuck her again with the large dildo, same as before. I was really frustrated this time since I was free, but still couldn’t enter her. I cleaned her up and we spent our day on the town. I was really hoping that when we got home I would get to finally enter my Mistresses wonderful pussy. When we entered however she handed me the dildo and smiled. I knew what I was suppose to do. As she took off her pants and panties, I inserted the plastic cock into my fly and slipped on the condom. Mistress had me sit on the couch and she lowered herself on the giant dildo. She had chosen to ride it this time. Very slowly grinding it she brought herself to orgasm several times. She settled fully down on the dildo and looked me in the eyes. “Does your little cock want to cum in me?” I nodded my head and told her yes very much so. “Fine, but here is the deal, you can fuck me as many times as you like tonight, cleaning me out each time and you will be locked back up tomorrow for another four weeks. Or, you can wait another chastity period and have sex with me the remainder of the month.” So basically I had to gamble here, one night of orgasms now for the month. Or, take the chance that my next period would only be ten days and get two weeks of sex. If I got in trouble or failed in any way a week of that would be gone. I have never had such a hard choice in my life. I had just done four weeks, and knew how hard it had been, but I also knew that taking the chance was foolish since she had made me fail on purpose last month. The longer I sat there and thought, the longer that huge cock was inside her. She was in no hurry for me to decide, as I could tell she was about to cum again.
Maybe the readers of this can help me out?