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With just a little pressure I felt him relax and the head slipped in. I let him get used to that. I knew he thought that his cherry had been taken and that he had performed perfectly. Little did he know that it was the easy part, I had prepared him as much as possible for that but the real deflowering was yet to come. I then pushed a little more and felt the resistance of the inner sphincter. “This might hurt a little when I take your Maidenhead.” I pushed a little harder keeping pressure on the reluctant muscle but not forcing it. I could feel him moving trying to find a way to allow me in but there was no entrance.I thought maybe with position the sphincter would dilate and allow penetration, but that didn’t happen. There was only one way now to achieve entrance. I grabbed his hips, told him to push out, waited until I thought I felt a slight dilation and then rammed my cock through the barrier. He screamed in surprise and pain, I stayed still while he adjusted to the new sensation. . I guess, if Will does it, I guess it's OK." Good, I know a spot where we can park and won't be disturbed." Jessie drove us to the township park. We parked in the far end of the parking lot, away from the homes along Route 30.I asked, "What do you want me to do?" Let's warm things up a little. My Dad took the back seat out of the van. We'll have plenty of room in the back." I hopped out of the car and followed Jessie to the back of the van. We climbed in and shut the back door. I sat down and Jessie straddled my lap, her legs locked around my butt.We pressed our lips together. Our mouths opened and our tongues dueled. My excitement and my cock grew rapidly. Jessie pulled her blouse and bra off while I removed my shirt. I kissed and massaged her beautiful tits for a few minutes. I tried sucking on the nipples. Jessie grabbed my head and pressed it into her tits, maximizing my contact with her nipples."Oh, God. That's good, Kyle. Keep doing that." she moaned. I continued sucking and.
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