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"And? Did you learn your lesson?" The mechanics of this little game I've set up for her are beginning to dawn on her. "N...no, more please." I love the addition of the please, it's great role play on her side. The first stroke is barely visible and the second one is barely leaving a mark, so I decide she can take a little more of a firm stroke, I extend my arm behind me and bring it down forcefully, bring it down firmly across both of her cheeks. She lets out a cry and she trembles for a second. She stays silent for a few seconds before she almost hesitantly says "...More". I quickly bring the cane down on her again, she was unprepared and lets out a stifled oh! sound. "More...what?", I ask her. "More...p..please". I push down on her neck a bit, forcing her to stick her rear out a little, with a long swing that produces a dramatic swooshing noise, I bring the cane back down on her, hitting her right on top of the reddening welt from the previous blow. She cries out for real this. I ran my hands around and across her big beautiful butt. It was so soft yet firm. I spread her cheeks and stared at her asshole. "Anna-Brooks.." "Hm…S-sir?" She was exhausted, barely able to speak. "Get ready." "Huh?" And then she felt my finger inside her anus. Her eyes shot open and she whipped her head around at me. "What the hell, M-Mike?!" "I'm going to fuck you up the ass, Anna-Brooks. Have you ever done anal?" "No, hey wait!" I smiled and shrugged. "It’ OK. I fucked your little mouth like you wanted. Fucked your little pussy like you wanted. So relax. I think there's a part of you wondering what my cock feels like up your ass..." She hesitated for a moment, then nodded. Anna-Brooks was beginning to feel the first ripples of pleasure from my finger slowly working in and out of her virgin hole. The one thing she'd never let any boy do. But it felt good, and damn him, Mike was right; there was a part of her wanting Her Man to take her in every way he could. She laid her head.
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