It takes a bit of practice and knowing your body. I've managed to cum like 6 times before from doing it. Personally I find it much easier to do when standing up as opposed to sitting or lying down, and also when I've already cum within the past 2 or so days. When I haven't orgasmed in a longer period of time, I find it more difficult to get the timing right. Although you will get bigger spurts of cum if you can pull it off that way.
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