If you can't find confidence in any other aspect of Skype sex, find confidence in that.
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It helps if you get excited by showing off your own body, and are eager to stare longingly at the bod of your person of choice. Remember, you're going to be moving your laptop around to get a better angle of your genitals, so I wouldn't worry too much about keeping a straight face.
Lots of advice about Skype sex will tell you that lighting and posing are very important because you want to look your best for your audience. Make sure that overhead light doesn't make you look like you're in jail. I like the way it looks, but I mostly like it for the pleasure it brings me.
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Even though you might be thinking, "My God, those are the greatest pectoral muscles in the history of pectoral muscles," there's no way for your partner to know that unless you spit it out. Personally, I couldn't care less if there are naked pictures of me on the internet, since there already naked pictures of me on the internet. Skype and most other video chat services include a little picture of you nested in the big picture of the person you're chatting with. The person you're all twitterpated over could turn out to be a jerk.
That's nice, because it means that if you try to screengrab their bits, you're going to get your bits all up in the photo, too. If it really makes you uncomfortable (remember: dies on the internet. If you're cool with that risk, know that you're in charge of what your partner sees.
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(Granted, if you're really a criminal mastermind, you could crop it out, but let's call it a deterrent.) Mostly, don't be a dick. You can always opt out of including your face in the frame.