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He was never really outside of his home a lot so it saved me a few trips to the bathroom. But this particular night he was out in his back yard, which was right next to my bedroom window. I couldn’t help standing there watching him with his shirt off revealing his perfect chest.I slid my hand down into my panties and watched as he cleaned up the few things he had on his back porch. I slid my finger into my pussy after playing with my clit and began sliding it back and forth moaning softly as I added another finger. Watching him there sent me over the edge as I exploded on my fingers then hurried to the bathroom to wash up.About an hour later while I was sitting in the living room watching TV I heard the doorbell ring. I got up and sighed hoping it wasn’t my parent’s home early and opened the door to find Mr. Jenson standing there with what looked like a briefcase. “Hello Emma, may I come in?” he asked softly. I opened the door more for him to walk in and he did so, “What brings you. He stopped at my sphincter and got ready to push. Then he thrust this time his dick was able to stretch the muscle more easily, but it was even more painful. I sobbed "Please stop.". But he felt the muscle giving way and made one more concerted effort to get his dick into my man pussy. The pain was excruciating; all I could think of was to push back and get this thing out of me. I tried to push it out as hard as I could. My sphincter opened, and his giant dick squeezed through. The pain was terrible even though it had popped through my cherry; there was no relief."Fuck him," Mistress ordered as she frantically rubbed her clit. He started to fuck me; first, he pushed all the way in. More stretching, more pain, it wasn't sliding well at all. Then he pulled out almost all the way. As the head pulled back through my sphincter, it felt like the biggest most painful shit of my life. He pushed back through again this time it slid in not really easily still fucking painful but sliding this.
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