1. Don't send them from your own Twitter account, nimrod.
It's quite easy to create a dummy Twitter account where your real identity is almost impossible for most people to detect. All it requires is an email address. It’s not even a violation of Twitter’s terms of service.
2. Use a dummy email address to set it up, dummy.
3. Mask your IP address, fool.
If you are likely to be the target of a criminal or otherwise hostile investigation, you probably want to use a proxy IP or anonymizer service like Tor before you go spraying pictures of your Johnson around the Webbernets. The Electronic Information Privacy Center (EPIC) publishes a long list of anonymizers and other privacy tools – most of them free for the download.
4. Choose your recipients carefully, Einstein.
Which is another way of saying, only send this stuff to people who really want to see it. Randomly shooting out crotch close-ups to comely coeds is not the smartest e-marketing strategy.
Weiner likely got ratted out to Breitbart to someone who either a) was deeply offended, b) saw dollar signs in the opportunity to hang Weiner out to dry, or c) both.
5. Don’t be stupid, stupid.
Don't take other shots wearing the same clothes (or lack thereof) where you're sitting there smiling at the camera like an idiot. Ever heard of Photoshop? Or plausible deniability? If you don't want to lose face, then lose the face.
Finally: The next time you want to send somebody a “package”? Do us all a favor and use FedEx.