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In my own opinion it isn't a matter of finding someone who can spank hard enough to cry it is going to have to be someone you connect with enough to bring tears about during a spanking.
I have had some sessions that left me completely black and blue afterwards and I barely moved and made no more noise than a possible gasp for air upon impact a few times. However, I've had other sessions with someone I'm extremely connected with and a few strokes and I'm starting to sniffle because it was all based upon emotions and emotions are the only thing that can bring tears for me.
I realize that you may be different because arent we all, but might be a good place to start with just finding someone you can have a connection with and build from there.
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