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He had read the things we had done in private. He referenced several of them. It shocked me that he was fine with me doing the same thing to my sister. I was excited and hopeful that I’d really get to do that. I was pretty skeptical my sister would ever let me.“Teddy can’t just start whacking me though for fun, right?” Tiffany asked.“You whacked him for fun, didn’t you?” Dad asked her. He reminded her that I would be Master Teddy to her. He had a trace of a smile on his face. “You and your brother will learn that punishment without purpose is counter-productive. If you get whacked as you call it for doing your best, then you will lose your motivation to do your best. He will, however, apply pain as part of your daily training. Is that something you are unwilling to endure?” Dad asked her.“You are not going to whack me harder than anything I ever did to Teddy, will you Sir?” Tiffany asked.“That’s a good question. I don’t know your pain tolerance, but the simple answer is no, it will. We were invited to a party with friends, I knew from the look on her face as she was getting ready that this would be a new step in my humiliation. She chose a very special bra, one that gave her support but absolutely no protection: I spent the entire night trying not to stare at the outline of my girlfriend’s nipples – as did the majority of the males there that night. And then he turned up: the smarmy, confident one. I groaned inwardly when she caught his eyes – if I knew my Mistress well she would delight in choosing him. She had me in agony most of the night, drawing her lips tantalisingly close and pulling away subtly at the last moment, as if our game could slip through the public eye. By the end of the night, when the party had died down and most of them had left, our true colours came out. I sat on the adjacent sofa and watched him pull her top off, eyes widening at her glorious breasts, his eager mouth eagerly and instantly engulfing her hardened nipples. She gasped and.
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