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Most of the women in the ring are well used and are nowhere near as tight as she is. Many have had kids. I could feel the head of my cock finding it way deep inside her, and as I like to do when I am right up tight and into her as far as I can go, I rest and let the woman adjust to the sensation of having a cock deep inside her. I watched her face as I slid my cock slowly all the way in. At first she sort of bit her lip then realized I wasn’t going to hurt her going in. Then I could feel her sensing the feeling of my cock going in slowly, she squeezed her vaginal muscles as I went in a couple of times, and I smiled at her acknowledging her action, she didn’t say anything but just smiled back with a look of concentration on her face as if to say I am not going to miss one second of this.Once I was right in and my balls were up tight against her beautiful firm tight ass and her legs were over my arms, I was pressing my entire body to hers.She whispered to me, “I am in. After putting on a pair of girl's white tennis sneakers (Barry's, of course; Penny's would never have fit), I pulled the sweater over my head carefully, so as not to mess up my makeup. Penny settled the wig on my head and gave it a few brushes. She pulled a pair of hoop earrings, a pendant necklace, and a handful of thin jangly bracelets out of her jewelry box and said, "Good thing you already have pierced ears." I stood looking at myself in the mirror. I looked to be about sixteen years old, maybe a junior in high school. I reminded myself of someone. I thought about it for a few minutes, then it came to me. "I look like Olivia Newton-John did in Grease," I said softly. Penny nodded. "Honey, you look absolutely gorgeous. If I can make myself look half as good as a guy, we're going to be the hit of the party!" I helped Penny don the pads and outer clothes for her costume. We had to wrap her breasts with an Ace bandage to flatten them. "I look good, except for.
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