I travel a lot for work, and the wife and I use cell phone pictures as part of our phone sex routine and we're usually really good about deleting them right after they're sent. It worked without a hitch for a couple years, until we had a mishap with a few of her friends.
We were meeting my wife's girlfriends at a bar and my wife and I were arriving separately. I got there first and had a few drinks with her friends. The wife called to ask for directions, and I took care of that, but then one of her friends wanted to talk to her. They were going on and on with the usual convo, so I excused myself to use the bathroom.
When I got back, he table was all laughing and got really quiet when I sat down. A few were blushing noticeably. I asked what the joke was, and the friend told me that when she hung up the phone, she thought it would be fun to dig through my cell pictures. She ran across a cock pic I had sent to the wife the month before and had forgotten to delete. The pic had been passed around the table and all the girls agreed that my wife is a very lucky lady.
She got lots of high fives when she showed up. I was surprised that she didn't act embarrassed, she seemed proud. I certainly wasn't embarrassed after the overwhelmingly positive reaction from everyone.
We still hang out with most of those girls and its funny, ever since that night, my wife and her friends occasionally pepper the conversation with big dick and threesome jokes. They always seem more excited to see me as well.
Probably one of the best mistakes I've ever made