I saw him pour a bunch of lube onto his condomed cock and then he rubbed some on my hole. He took his finger and slowly pushed it in me to loosen me up and get some lube inside. "Do it Coach."He moved his cock closer to me and I could feel his head pushing against my hole. It was big. Much bigger than his finger. His finger hurt a little bit, so why was I doing this. This was going to hurt. Could it even feel good? There was only one way to finger out. He started pressing his head harder against my hole. I could feel myself opening up. It didn't feel good. It hurt. Then, after a moment, it felt good. "That hurts Coach, go slow," I told him.He nodded at me and I could tell he was going slow. His head started going further and further in and I winced in pain.It hurt but it felt strangely good. Even though it was killing me I let him go in further. He was about 3 inches in and he started to pump. He knew I couldn't take the full thing, or I wasn't opening up enough for him to get it all. When she turned to face me, her pucker was replaced with a broad smile.“Come here my dear boy,” she said. As I took her outstretched hands, she pulled me into a hug. It was the first time we had hugged since November 1st—we had both been naked at the time. As I felt the woman whom I had experienced with no clothes on, the material of her habit was bulky, and the veil and wimple both felt strange against my face. “Oh Toby, Toby, TOBY,” she said, “I know you have been wondering if what happened in the fall would ever happen again.”With great hope in my heart, I asked, “Will it Mother?”Taking my hands, she pushed me away and gauged my eyes. “Yes, Toby. But we must be patient. We can’t let our relationship become so blatant that we should be discovered. We have to be aware of wagging tongues.”For Christ’s sake, I thought it’s been six months!Studying my face, she said, “It’s been a long time for me too, my darling boy. But school will be out in six weeks, and you will be here often.
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