I went slowly and gently. I started to fuck him with my finger making a point to rub his prostate. “Oh shit man that feels good, keep it up.” I pushed a second finger in. Then I pulled them out and soaked my cock with oil. I also squirted his ass again and I grabbed my cock, put the head at the entrance, and slowly pushed the head in. “Oh shit man that fucking hurts pull it out…shit PULL IT OUT MAN!” “Tom you have to trust me, just relax, and stop trying to push my cock out. Let your ass muscles relax. Believe me the pain will subside and it will start to feel as good as my fingers did.” “Okay… okay I am trying but shit man your cock is so fucking big.” It was comical. Here I was standing behind my friend with the head of my cock shoved in his ass, this big strapping hulk of m man was whimpering like a girl. Finally, Tom relaxed his ass, the pain subsided, and I slowly pushed more of my cock into his ass. I grabbed his hips and shoved the rest of my cock until I had impaled. Once my pants were lose she pulled them down around my ankles, quickly followed by my boxer shorts. My virgin cock was rock hard and 9 inches long directly in front of my teacher's face. She gasped and said, "My, my Simon what a huge cock you have. Have you used that monster on any of the girls yet?" I stammered, "No." Mrs Diamond smiled and asked me, "Would you like me to give you a blow job?" I nodded to indicate yes, so she took hold of my shaft and pulled back the foreskin revealing the pink head and slit of my cock. Her touch was electric on my organ, but that was as nothing compared with the jolt that hit me from my cock when she opened her mouth and started to explore the exposed helmet of my cock with her tongue. She swirled it around and probed the the slit. At the same time she was gently squeezing my hairy balls with her hand. My cock felt as if it was on fire as she took first the head and then most of the shaft of my cock into her mouth and throat. She began sliding her.
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