For what it's worth, my ex-wife was short, overweight, and had huge boobs, and my dad blatantly asked her to flash him her bra all the time. Then he said once she is used to that, maybe she can flash him her boobs, too.
She never flashed him either, but she thought about it for a long time. The thought of my dad seeing her bra and boobs turned her own a bit, but she never went through with it.
My dad never bothered to ask my current wife because he knew she would kick his rear for even asking.
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