I have done it several times on both Skype and Google Hangouts. The first few times I did it was more of a straightforward "show off" type thing where we both gave each other a good luck at the goodies. I have found that older women are a lot more willing and interested in showing off while younger women want to see my bits but won't necessarily reciprocate.
As I've done more chatting online, I've found video to be a fun way to add a twist to roleplaying. With a couple of my roleplay partners, I've built a story up to a big moment and then we've agreed to play out the climactic moments on video chat. VERY hot.
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