With his trousers and underpants around his ankles, Alan Matthews breathed heavily and gripped the far edge of the desk ever tighter knowing that if the remainder of his caning was as merciless as the twelve strokes he had already received, his scorched and throbbing buttocks would feel like they had been positively flame-grilled by the time the cane finally came to rest. Adding to this painful ordeal though, was the fact that Mrs Harwood the Headmistress had remained in the study for the duration of his caning. Although it was customary for two members of staff to be present whenever corporal punishment was being administered, the fact that one of them was not only female, but the Headmistress herself, was a point beyond humiliation for Alan. Although in her forties, Mrs Harwood was an extremely attractive woman. Ever since Alan had gone on a fishing trip with classmate and friend, Jonathan Elliot along with Jonathan’s father, Alan had found himself entering into what was perhaps,. Samantha? No too close to yourreal name, Simone? Sarah? Sue? How about Sasha? Ya, you kinda look like agirly girl Sasha? But what one do you like?" she said. "Um, ya, I guessSasha is ok."Well, ok Sasha let's get going, we don't want to be late for yourappointment do we?" Appointment?" Oh one more thing, I think it's your time of the month girly and we don'twant you to leak."She handed me a feminine pad and a tampon, and I asked, "Do I need both?"She said, "Of course, can't have you walking around in soiled panties canwe? What if you get excited? One is so you don't leak and one is to giveyou a little more of a feminine awareness, do you need help putting in thetampon?"I said that I had never done anything like that before, and she said, "Notime like the present, just go into the bathroom and put one foot on thetoilet pull your panties aside and insert. Here I will be nice here is alittle lube for your first time girly. If you need help I will come in butI think you're a big girl,.
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