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I've always found that kind of an erotic fantasy too. I have tried it with a few partners but the problem is I'm sitting right next to somebody who I think is sickeningly hot and after a few minutes I find that there are just to many tempting places to put my cock besides my own fist and it falls apart from there. For me it seems more like a foreplay technique then the setting for an entire session.
A few techniques you could try would be to gently guide her in that direction during foreplay, you move your hand to take care of yourself, push her hand to do the same and see if things take off from there. It could be a good way to break the ice for the first time.
How about just starting on your own? If the mood is striking you go to town and see if she follows. Knowing its a fantasy of yours it would be a pretty hard clue to miss.
Bring it up out of the blue. "Hey you wanna? If you don't like it we can always stop." No pressure and the adventure is there is she wants it, seems kind of win/win to me.
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