He had me riding on it with his cock completely outside of my hole, but pressing against it harder and harder and it did feel amazing, but I realized ...that as soon as it started to slip into my hole at all it hurt. So he stopped and licked and fingered my hole a lot more, and I got back into position and after a few more times the head slipped into my hole. I almost saw stars and hollered.He calmed me down again and did more licking and fingering. lt felt good and hurt at the same time because. I wonder whatever happened to him?" Miranda crossed her legs haughtily and lifted her nose as a wicked, satisfied smile crossed her face. I could only guess at the fate of any male who came into contact with these superb women. My Balls tingle all the more. I was then commanded to stand by the ladies with my arms apart. I was measured around the waist, legs arms etc. Agnes had her sissy input the details on a tablet from Agnes' bag. Some 'suitable' clothes were ordered for me.Blanche was now. I got back to the school, showered and was about to get changed. Mr Calvert came out of his office still in his running shorts but no socks or top on. "That was kind of you he said". "Helping Matthew, and staying with him". He put his arm around my waist, held the back of my head and kissed me there in the chaining room. He stopped but I kissed him back. He was an amazing kisser and I didn't want it to stop. "We shouldn't do this" I said. "You can get into serious trouble" but he just looked at. I said I do but I was scared it will hurt. He said if we take our time and do it right it will be bearable the first couple of time then just pleasure. That night he started by liking my asshole, I felt bit tense at first but then I relaxed and started to love the sensation. Soon after he started to push the tip of his tongue in, I almost came when I felt him penetrating me that way. The next day he used his finger for the first time and I loved it, since then he will work my asshole with his.