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ask her,
she knows her own breasts better then anybody else ;)

Breast play is good anytime; although having just said that, there are some dos and don'ts.

Work your way from outside her clothing to inside and actually touching them in progressive stages and as her arousal continues to build. So, unless you are going for a Quickie or roll playing in which you perhaps back her up against a wall and have your way with her, better to brush over them as your fingers move to other areas. As things progress you can give them more and more time and attention as well as exposing them in stages for more intimacy.

The nipples and surrounding Aerola really only turn on after she becomes very aroused. Until reaching this stage, just give them fleeting attention while continuing to kiss and caress the rest of her body. How you disrobe her depends upon the mood and circumstance. If she is not completely nude in the beginning, then remove her clothing in stages over time as her arousal builds. You can cup her breasts from outside, later unfasten her top button by button, slipping fingers inside to do the same over her bra. Moving right along, you can move fingers down from the neck, slipping them inside a cup. The top can come off and the bra unfastened and left to dangle as you continue to explore in more depth and detail.

Breasts are not all the same, or, should I say--women are not all the same with regard to breasts. You will have to learn how she likes them involved in your lovemaking activities. Some people like ongoing stimulation up to and right on through an orgasm; others find early play pleasurable yet, later, very distracting when trying to trigger the orgasm.

Unless your partner tells you that rough handling is OK with her--don't. Fondling should be loving, caring, soft and gentle for the most part. Perhaps the most important "don't" is to don't twist a nipple. A gentle tweak is OK, which is a similar but a more gentle movement. A dry palm or fingers are OK for any casual caress; however, if you are going to pay prolonged attention to a nipple, then use saliva or a lube.

Whether a woman is new to lovemaking or very experienced, explore and learn what she likes and does not, and later take your cues for what to do from her reactions. You may find that one nipple is more reactive than the other. If this is true for your partner, then you can devote more attention to the one that is more sensitive. Apparently, there is a direct line between the nipples and the genitals. For women the interaction is much stronger than it is for us guys. For whatever reason, placing a layer of material like a sheet over our nipple(s) and gently scratching one or the other with the edge of a fingernail produces a stronger reaction than direct contact. Presumably, this will hold true for her as well. Test for it and see.

I like giving my wife's nipple some progressive bouncing by using my hand like a washboard. This can be done with a flat hand and fingers together, or, slightly spread apart. Just move your fingers over the nipple and let it bounce between them. This is one thing you can do if she likes it.

For a woman whose breasts lie flat against her chest when she is flat on her back, you can get astride her and press your palms against each, rubbing them in a circular or grinding motion against her ribcage.

Of course there are the standards like kissing, licking, sucking, and lapping that can all be done amoung other things. As always, explore and learn together.