The Gentleman's Guide to Sending Dick Pictures to Random Women on the Internet.

1) Consider the wisdom of sending a dick picture. If the relationship she is seeking could be construed as a "dating" or "friendly" one, sending your dick at all is mega creepy. And even in the context of casual sex and cybersex, women aren't necessarily aroused by penis JPGs. You might want to wait for her to ask for a dick picture, rather than using it to introduce yourself.

2) Make sure your equipment is suitable. The proper condition for dick photos is clean and dry (seriously, ewww), fully erect, and with well-groomed pubes. If it can stay fully erect without you death-gripping it around the base, so much the better.