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This resulted in his little cock usually dribbling cum as I worked the dildo in his ass. Before the end of the year was out I asked if he would wear a panty when we had sex. He was a little hesitant at first saying "it was just something I wanted to try, I am not into wearing woman's close." I asked him to do it for me that it would make the sex more enjoyable. I then took the bag out of my closet and showed him what I bought for him. He tried one on and I started to rub his little dick through the panty. He got instantly hard and I rewarded him with a bj. Stopping short again of him cumming and pushing the dildo in his ass. I licked and kiss his balls as he came shooting down my back and the side of my face.While we played like this for a while I started to introduce my strap-on in his ass while he wore the panties that I bought for him. He was getting more used to being fucked than actually fucking. It was close to a year and he had not put his cock inside me. I wanted to introduce. VERY slowly I started sliding my finger in. after just ½ inch, I realized that it was very tight and that my middle finger might be to big. So out came middle finger and in went my pinky. I retraced my steps with my pinky first over her clit then around it a couple times then back to her opening. Slowly I slid it in. much better and most of all she didn’t seem to have any discomfort like she showed with my middle finger. I slid it in just a little then backed out for another try. The second time it went in more then half an inch. Over and over I moved in and out till I got to her hymen. I pushed up against it and moved around in circles. Since I had already knew how a woman gives birth, so I knew that where my finger was could stretch. Slowly I worked on her pussy. Finally I managed to get my pinky all the way in. Man, what a feeling. I just love feeling the inside of a woman. Slowly I pull my pinky out of her pussy and start to go with my first choice, my middle finger. After about.
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