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I knew exactly who to text, and all it took was,“Hey!” Scott replied almost instantly, “I know what you really need.” I said, “I know you do?” He replied, “When?” I said, “I can be over at noon and stay until the football game is over.” He said, “Come here but be prepared!” I showered. I didn't dress up but I kept it real simple, plain sweat pants, tank top, and a sweatshirt and left immediately. I arrived and didn't notice anything unusual. I went to the door and was greeted by a smiling Judy. She led me to the hot tub which we got in to and made small talk. I had no idea where Scott was or that anything else out of the ordinary was going to happen. We talked about the party and other things women do, until she said, “Let’s get ready.” We went to her bedroom she began rubbing massage oils on me but then told me to lay on my stomach and relax. She applied lube on my ass until she could work her fingers inside to loosen me up, and fit me with a but plug. I was oily and horny. She. My penis slid in easy and soon I was all the way in her and pumping. She spread her legs wider to let me slide in as deep as possible and arched back further to be able to slide all the way out and back in just so I could try out new things. I wanted her to feel every inch of me. I was holding on and not cumming as I had hoped but it was though, when suddenly my penis slid out of her vagina. I tried to recoup and not drop the ball so I pushed forward to slide into that sweet hole I so dearly wished I had on me. In her excitement she had raised her back too high and when I drove back down I hit her anus, I didn't realize why it would not go in at first so I kept pushing but she knew right away because of the pain, before she could react I slid into her, "Oh no oh no" she screamed and I stopped, "you're in my ass, oh the pain, don't move Danielle!". I stopped and felt instantly bad, I knew how much it could hurt, especially with something this size. She was breathing hard, trying to.
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