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He led me into the living room and asked "so are the nylons for me?" too nervous to answer I nodded and took my coat off to reveal my full girly outfit and his lit up. He looked me up and down and told me how amazing I looked. We sat on the sofa together, he had some very explicit gay porn on the TV a little twinky guy getting fucked by an old man.He asked if I was OK and I told him yes I'm fine, I could see his cock bulging in his sweatpants, I reached over and started to stroke him through the material. Dizzy asked me if I wanted to see it and all I could get out was a sheepish "OK"He pulled his sweatpants and released his hard throbbing cock, it wasn't like pornstar huge but it was far bigger than mine, I wrapped my hand around it, fingers barely being able to touch my palms and slowly started to jerk him off, I loved watching his foreskin slide over his head, the warm feeling of his hard cock my hand, I was mesmerised. I was snapped out of my day dream when I felt his hand on the. I pulled my fingers out and quickly replaced them with four fingers from my right hand; he was now dilated and ready to be impaled. With my left hand I coated my cock heavily with lube, spread his cheeks and removing my fingers, placed the tip on his greasy anus. I reached under, grabbed a nipple, and leaning forward whispered in his ear, “Are you ready to lose your cherry, I am going to take it.” He moaned a faint, “Yes”. 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.
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