Thats probably the point, that he's too small to achieve such a monumental task easily. So instead she's setting him a near impossible task to see how hard he will work and how much he will devote himself into trying to massage her cheeks like that. Depending on how he does will determine where on her he gets to be placed afterwards.
I know that if I were him I'd give that tush all the attention and work that it deserved and keep going until a desired level of satisfaction is achieved in her :D
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