The closest I ever got to sending nudes was me trying on lingerie at Victoria's Secret, trying to pick something for me to wear when I visited my girlfriend, I took pictures of each option and sent them to my her.

We broke up since then, and I'm sure they were deleted. If by some chance they weren't, I know she'd never ever use them against me. She's not that type of person.

Yes, because I'm not dumb enough to actually send them to people :|