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I took the pink dildo, raised my balls, and put it in between my legs, leading the tip to my hole. I would have almost preferred her doing it instead of me, the idea of me doing it to myself made me feel more humiliated and controlled rather than being forced. I pushed it in slightly, trying to test what I was about to get myself into. The tip slid in slowly, I gasped at the pain. It felt as if i was tearing myself open. Callie watched on anxiously, admiring, giving pointers, egging me on. I pushed it in further, breathing harder now and taking in more breath the further it went in. After about 5 minutes I had worked it almost 7 inches in. Callie loved the way i looked, she did my hair while she waited for me to work my dildo in, she put my semi long hair in tiny pigtails. I looked like such a girly slut with red make up, pig tails, and a pink dildo in my ass.After the stretching was done, Callie squirted some KY jelly on the tip of the cock so she could watch me. He closed his eyes and tried to hold back but couldn’t anymore and came all over his stomach. Sam was a little red faced, but enjoyed making him cum.“Sam, that was great. At my age you don’t know how many orgasms you have left.”“Mr. Stevens, please don’t talk that way. You are still a young man and hopefully will have many more orgasms in you.” She laughed and winked at him. “Will you charge me if I need a massage after soccer practice?” she playfully asked.“No, giving you a massage would be my pleasure and always free.”Richard knew that he had reeled her in a bit and needed to change tactics to get what he wanted, since he didn’t know how far he could push her voluntarily. The next Friday she was changing into her pajamas to get ready to give him his weekly massage and he walked into her room suddenly while she was completely naked. “Mr. Stevens, I am getting dressed! What are you doing in here?” She tried to cover her nakedness.“Sam, you have been teasing me since you came.
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