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The pain on Chris’s face as he screamed into the gag was clearly visible and Sally seemed reluctant to force him further. I went over to pres and got out the bamboo cane and approached Sally from behind.Thwack! Sally screamed lunged forward and buried the dildos full length into Chris ass, I gave her a full dozen strokes, Sally lunged forward every time hammering Chris’s ass. “Now Sally fuck him hard and fuck him fast or I’ll give you 50 strokes”.“B..b..b.but, he’s bleeding!”, she sobbed.“Good. Little bit about her she's a black 5'8, somewhere in her late 30's women, with curves in all the right places. We started exchanging emails and this continued for a few weeks, just getting to know each other our likes and dislikes in the bedroom, what my expectations were for my first time and what I wanted to try etc.. We eventually set a date and time to meet up at her place so I could lose my virginity. I got to her place around 1 in the afternoon, was extremely nervous, not knowing what was. She’s a little older than I,late 20’s. Very nice shape. I’ve known her since high school. Once in collegeI got her to try out being bisexual. She seemed to enjoyit..but obviously felt very awkward. We never repeatedthe experiment, and have remained close friends ever since. Now she was crying on my shoulder, and I was feelingbad for the unsisterly thoughts I was having towards her. For the next few months she went through. “If I could guarantee your physical safety, and assure you will find yourself in no disciplinary hot water, would you like to find out if it is a sexually arousing situation for you Jill?” Jill sat there shocked, but not surprised. ‘Idiot” she told herself, ‘you were the one who brought this up.’ She was scared and nervous at the thought, but curious and intrigued at the same time. “I don’t’ know. How could you guarantee those things?” she asked. “Well the discipline issue has already been.
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