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I put on a rubber and lubed up my cock and her “virgin” ass. Normally I would be gentle with an anal virgin, but this was punishment and I wanted it to hurt. I pushed my greased pole into her tight ass hole, pleased by her pained moan.With my right hand on her hip I grabbed a handful of her hair in my left and pulled to arch her back. I slowly pulled my dick out of her ass as she shuttered, then I thrust back in forcefully. She cried out in pain as her panties fell out into my desk. “Oh, does that hurt?” I taunted, she grunted an affirmative “uh, huh” as I thrust into her again. “You’re such a skank I actually thought you might like this!”I pulled out and as I thrust my cock deep into her ass once again she breathlessly confessed, “I love it! I know I’m a dirty slut, that’s why I need you to punish me Head Master. Fucking me where it hurts is the only way.”This was turning me on even more; I began to quicken my stride. I pounded her ass mercilessly for another dozen strokes.. This is my breast. This is my thigh. This is my shoulder. This is my mons… And then the finger was stroking a determined line over her wet slit, and it was as if all her nerves ended in wet desire. She had to lock her knees to keep them from buckling, grit her teeth to keep from moaning as the finger pushed back downward and then slightly into her. The moan escaped anyway, but the finger was unceremoniously removed. She was panting again, she realized. ‘I’m going to put you on your knees now,’ he said, and his hands were in her armpits holding her firmly as he drew her forward and down. She regained enough composure to bend her knees as he lowered her, felt him temporarily position his leg between hers so that she spread her knees a bit. They came to rest on a soft pillow mysteriously placed there, for which she was grateful. She went to settle back further, but he stopped her. ‘You will move your body only as I tell you to,’ he stated flatly, the voice moving around behind her now.
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