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My hair was getting longer. I was pleased about that because Master Ian would not let me wear a wig. When out dressed as a sissy, every thing would be...feminized except for my hair, and that gave me away every time.I got plenty of practice at giving head too. Master Ian loved to get his cock sucked and Caroline sucked him in every position possible. I had learned how to pace myself to bring my Master off every time. The only thing that had really surprised me was my first punishment. I had never. “It felt like it was her way of saying goodbye. Not like we’d never see each other again, but as if a phase of her life had ended. When she got in her car, she gave me the briefest of hugs and a quick kiss rather than her usual mashing of bodies together and a deep French kiss.”“You knew that had to happen someday. And I’m pretty sure you were encouraging it.”“Oh, I did. And I was. I’ll be fine. She’ll always be special, even if we don’t end up together the way she’d hoped.”“It’s probably. " Were you washing? Did I disturb you?" She asked obviously referring to how I was dressed, or undressed as it were."No. Not washing." Oh, is this the time? Am I to learn making love?" Her voice sounded scared, but also excided."Come closer."She came promptly and stood in front of me, waiting for me to say what I wanted, displaying the subtle signs of her virginity, a flush across her cheeks indicating embarrassment, a hint of awkwardness revealing a lack of full awareness of her own body. I. ..." she beggedHe thrust his hips forward aggressively penentrating her dry pussy, causing her to scream as pain ripped through her body. He drove himself into her inch by painful inch, ripping her as he went, until his balls pressed against her clit. He paused for a few moments as she thrashed beneath him, to his enjoyment, her body clenched him tightly. He grabbed her forearms tightly, instantly bruising them with his vice like grip, sending agonizing pain up her broken arm. He pulled.
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