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” Debbie turned her head towards me, “I’m sure I will Sir, I’ll never do anything like that again I promise, but I know that I deserve to be caned.”I selected the first cane that I would use on her. It was a light, whippy cane with a crooked handle and although capable of inflicting a mighty sting it would provide a relatively tolerable start to her caning. “Six strokes with this cane Debbie,” I informed her as I squared the cane to the centre of her gloriously reddened bottom. “Are you ready?”Debbie tucked her hair behind her ears and then reached forward to clutch the far edge of the desk before responding, “Okay Sir, I’m ready.” There was an air of trepidation in her voice, perhaps only to be expected from someone about to receive eighteen strokes of the cane on their bare bottom. I allowed myself a moment to savour the scene, the beautiful reddened buttocks, the sight of her vagina and its surrounding enchanted forest of pubic hair peering so provocatively between the tops of her. A few days later my gf called for me to head over to her place. she told me that her sis. and her agreed that i would be the first to do her little sister. her sister was curious and wanted to know what we were doing and wanted to try it. so they discussed what Daniel and her were doing and how it felt. her little sis. wanted to try it with my friend, but my gf thought that it would hurt way to much and it probably wouldnt fit in her. she said that i would be perfect for her bc i was small enough that it wouldnt hurt as much and because i probably had the dick size as a guy her little sisters age (her little sister was two years younger than julie), so maybe it would be ok. her little sister was very short about 4'7or 4'8 and much thinner than my gf and had a flat chest. it was really weird the first time it happened. we did it in the dark. my gf told her that it would hurt a lot the first time but for her to take it and it would get better the more times she did it. i just.
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