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I informed him that I would go slow and that I knew his body well enough to know if the pain was too much and that he was too trust me. He murmured o.k., closed his eyes, and slumped against the table. After generously applying more lube, I moved in behind him to get ready. It was at that moment that I thought he might be right, that thing was huge. I gently squeezed and massaged his cheeks around the head of the dildo and slowly began pushing it into him. He was loosened enough from the previous dildo so that his ass accepted the new one, but I could see how much more it had to stretch and I could feel his apprehension under me. I went very slowly and it actually took several minutes for the head to pass his sphincter. He moaned loudly as it slowly began to enter him. I could tell he wasn't relaxing like he normally does but boy was this starting to look good. The site of that huge dildo slowly sliding into his ass got me going again. I held back though so as not to be to rough too. The only catch was that the boys have a ten o’clock curfew the night before a game…so given the three-hour session with an hour in between to get cleaned up…I would have to start at three o’clock in the morning and get sexually assaulted for fifteen hours…each Friday…for four weeks in a row.I thought it over and I really wanted to help out their charity. Then I thought about what the coach might have told them about me and how he himself had used me.So I said, “Tell them that it will be a thousand dollars per session and I’m in.”Their eyes sparkled, as they comprehended the twenty thousand dollar contribution that I was making to the preschool fund.They told me that I would be using their room again that year and that they would be my maids in waiting, bath me in between, and change the sheets. They were so excited that they were shaking…so was I.However, I had visions of five monsters with huge trouser snakes ravaging me constantly for fifteen hours. Taking turns and gang banging.
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