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I would have thought that given Amanda is such a hot babe, the opportunity to wrestle with her would have been leapt at. Even if he lost it could have been a lot of fun doing so, and he wouldn't have been any the worse off. But to back down so timidly, without a fight as it were, simply played into her hands. Allowing her more sadistic side free reign to do whatever she wanted to do to him.

What Amanda did have was a very powerful personality. She was a leader and when she wanted to feminize a guy, either to make a point or because she thought it would be fun, she was capable of getting other people to see her point. The reason that Kyle backed down from wrestling Amanda was she intimidated him and he figured it'd be easier to explain the makeup as him being a good sport without being forced to do it after losing a wrestling match.
As I compress semesters in 6 or 7,000 words, I'll have to be careful to show the resistance. I tended to leave out some of the mundane arguments.
James, the review I was referring to was on Amazon. I considered your review positive and was very grateful to see it. I definitely agree that there are places where it could be improved.

While its important that the guy be resistant to being feminized, the degree of his struggle is less important than how believably controlling and willful the woman (or man, perhaps) demanding his feminization is. A male paralyzed by fear of exposure, afraid to do anything but comply, doesn't make the story less hot.
If the reader is presented with a dominant character who is clearly capable of stripping someone's masculinity from him, reducing him, intimidating him, and turning him into a feminized pet, that's where the hawt comes in.
I thought Amanda was not only entirely capable of this, but rather brutally efficient at it.