Cleo had told me to make him cum before I caned him, she said it would hurt more. I gave him a second enema to be on the sale side and then put on my strap on and with him in the diaper position I fucked him up the bum and wanked his cock at the same time. He still had not come so I withdrew the strap on but kept on wanking him. When still nothing happened I spanked his cock for not coming and then put him over my knees with his cock wedged between my thighs. As I spanked him again he was humping my thighs and I hoped this would make him come at last so I could cane him de-spunked as Cleo h...

Cleo had told me to make him cum before I caned him, she said it would hurt more. I gave him a second enema to be on the sale side and then put on my strap on and with him in the diaper position I fucked him up the bum and wanked his cock at the same time. He still had not come so I withdrew the strap on but kept on wanking him. When still nothing happened I spanked his cock for not coming and then put him over my knees with his cock wedged between my thighs. As I spanked him again he was humping my thighs and I hoped this would make him come at last so I could cane him de-spunked as Cleo had instructed. After about 100 spanks, to help him climax I said he could touch me and so I made him get up and told him he could touch my boobs and kiss my bottom while he wanked. There is obviously something wrong with him because he still didn't come, I think it's because he wanks too much. I decided I would just have to cane him harder to make up for him not having come first. I made him bend over and selecting my first cane I started to cane him hard. After 3 strokes he jumped up out of position rubbing his bum. I spanked his cock to make him bend back over and then gave him a volley of 3 very hard very fast strokes that had him jumping around protesting and moaning. I made him bend back over and got my second cane, giving six of the very best. His bum was very sore, all the cane stripes were on the sensitive lower part of his bottom and looked very painful indeed. I placed him back over my lap so I could spank him on his caned bottom, this time it would be a much longer spanking, but I had to stop after 135 spanks because he had finally actually come on my leg! I made him lick his spunk off my leg and then I put my skirt back on and made him bend back over for some more of the cane. I selected my longest cane and started to thrash him on his already well caned and spanked bottom. After 3 strokes he did his usual thing of jumping up. I pushed him back down and delivered another severe volley of hard fast strokes that had him reduced to a quivering mess. After a good scolding I sent him to stand in the corner with his hands on his head. I think you will agree that from the state of his bottom, this was his most severe thrashing yet.

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