Ah! Not over a text...a friend wanted some music I had saved on a USB flash drive. Without thinking, I lent him the flash drive, completely forgetting on that same flash drive I had a file stashed on there named after my girlfriend and content of the folder matched the description...
I had saved those files to a different flash and for some reason I thought I deleted them off of there. When he gave me the flash drive back he said thanks, then jokingly added that all he wanted was the mp3s but the other things were nice as well. I didn't know what he was talking about until I went home and checked out what else was on there...

External HD
 

This actually wasn't my screw up but my wifes! :D A friend of mine from college was passing through our town around Thanksgiving and I had an old external HD that he had let me borrow years ago so I could have a shit ton of music, movies, etc that he had collected. I even bought the same kind of drive since I liked his to keep my own stuff on. For one reason or another he kept forgetting to ask for it back and I kept forgetting to return it, and eventually we both sort of forgot about it being his. Several months ago, I found it and my drive still boxed up from when we moved. I set them both out near my laptop and let him know I had his drive if he wanted to get it back sometime.

He said he would grab it next time he was in town, so I agreed and left it sitting under the computer table. I plugged my drive in and went through all the crap I had saved on there, making some space so I could back up my current laptop, which of course included a not insignificant amount of nudie pics of my wife, among other porn. So I backed it up and put it away back under the table, not thinking much of it. Fast forward to Thanksgiving and we had gone out to dinner with him and his wife, and were standing outside talking as they dropped us off. Of course neither he nor I were remembering about the drive but apparently my wife did since she disappeared inside to use the restroom and returned carrying it out. Again I didn't think anything of it, just thanked him for letting me "use" it for about 5 years and he laughed and said it wasn't a problem.

They left and I didn't think any more about it until earlier this month I went to back up the laptop again. Imagine my surprise when I plug it in and don't see any of the stuff I was expecting to see! For a couple minutes I couldn't figure out what was going on, I thought maybe the backup messed up or something, before realizing this was actually my friend's drive. Not much more time elapsed before I realized my wife must have grabbed the wrong one, not realizing there were two virtually identical drives, and handed over the one with our backups... complete with hundreds of her nudes and sex pics!

Now I haven't heard anything from my friend about it so I don't know if he realizes what he has, formatted it without looking at anything, or just plain hasn't plugged it in yet. I'm pretty certain he would have mentioned something to me if he saw it was our stuff on it. I also know he would have snooped through it to see what all there was, just because! Now I'm not sure if I should contact him and let him know he has our drive by mistake and how to find out if he looks on it without making him too curious! I'm also debating about if and how I should tell the wife about her mistake, I'm sure she would have an interesting reaction LOL... especially since he isn't one of the guys that has seen any of her nude pics before!

Any suggestions on how I should go about it? :)

is what are the breasts of your wife on your avatar? :p

If there is any chance you will be anywhere near where he lives anytime soon maybe you can arrange a visit and bring his drive with you when you do, attempting to complete a trade on the spot with no prior notice - just say you realized he got the wrong drive so here is the "right one", that way he may not get time to go digging through your files before turning it over. Maybe the wife doesn't need to know if your friend says he never looked at the drive and didn't realize he had yours.

I once sent a folder of pics of my shy wife to my best friend. The kicker is he was sitting across from her at table while the four of us were eating dinner.

This may not be the right thing to do. But it's what I would do!:D

Seems like how you go about it is dependent on whether you want him to see the photos or not.

I've decided on my course of action... I definitely want him to see the pics, especially if he will enjoy them and not be weirded out by them. I'm going to tell my wife about her mistake at the beginning of next week when due to work and weekend plans it will be at least a couple weeks before we will have time to go swap drives. This way I can see her reaction and what she wants to do and decide what I'll say to him. I should be able to feel out if he has seen any pics or not and possibly drop hints as to the content on the drive. This will give him plenty of time to snoop and result in lots of nervous excitement for me and wifey since we will have awhile to wonder if he is seeing her in all her glory. Should be a fun few weeks... :cool:

A few years back, my wife sent me some pics by cell phone whilst I was away on business - she sent me a text asking if I have enjoyed the pics ?
I replied "What pictures "
Her reply was " Oh fuck wait a sec "
It seems that she mistakenly sent the pics to our sons cell
Luckily for her he was still in bed so she managed to delete the message
LOL

Unlucky slip that :D