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Heh, my women have all been unhelpful with my curiosity about how to play with boobs. I adore flat chests and almost flat. But there are no boobs to play with, only the nipples. Large, soft breasts used to bore me, but now I like to put the woman on all fours and pat them from the sides like a cat swats a ball hanging on a string. Or pat them from below with cupped palms. With the right timing, a palm catches one before it has fallen all the way back down. Pat them to the rhythm of a nursery rhyme. This game is only possible with large and squishy boobs.
I’d openly ask her to take your hand with hers and have her show you what she likes.
It can definitely hurt when you squeeze it. But i recommend the alternative of sucking and licking the nipples instead. You can also flick and pinch the nipple, it stimulates pleasure for the girl when penetrating.