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Unfortunately there is no quantifiable or simple rule here, as his threshold for embarrassment will vary in proportion to his shyness and his pride, which are different in every man. Well, for starters, in the early stages, you will need to give him blatant signs of your interest.
She fingers her shaved pussy to turn her man on and then sits in between his legs, massaging his cock with both hands, watching it get bigger and harder for her.