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Sorry, this is training and not cruelty. How is this sissies manpussy going to have more fun until she opens this boi's hole further. He should be riding with friends pushing him down slowly. I have a guy half his size in his 20s who accepts challenges like this with gentle moans and is thanking me for making him be all sissy he can be. It takes time but with attitude and determination you'd be surprised what manpussy can take.