I'm with my girlfriend at a beach with beautiful clay cliffs. The beach has a clothed section, where we were, and a nude section further down. I got bored and took my camera and went for a walk to take some photos of the cliffs. We stumbled upon the nude section accidentally (honestly, it was our first trip to this island). My gf was amazed at the nudies. She excitedly grabbed my camera and against my objections took about 10-12 photos of the nudies.
Post-vacation: She calls me and tells me to email her the vacation photos. I send her about 15 emails with 10 photos each. All sorts of vacation pics -- us on a boat, at museums, at dinner, etc. Well, my Outlook auto-entered names once you started typing. For all of these emails to my gf, I typed in the first 2 or 3 letters of her first name and then hit enter, as Outlook recognized her.
After I sent the emails, I went to my 'Sent' folder and saw her name there for every email...except one. You see, my previous female boss had the same first name. And Outlook auto-entered HER name on one email. No problem, I thought. She'll just see us on a picnic or whatever when she looks at the emailed pics.
I opened that email and to my horrifying horror of horrors, the first thing I see is a shriveled-up pecker of a fat 70 year old man on a beach (taking up about half of my computer screen), with an equally droopy old fat nudie married couple in the background, full frontal.
I looked at the other 10 or so photos on that email, and yup, all of them were nude beach photos. Virtually all of the nudie pics my idiot gf took ended up on an email to my former boss.
I panicked, started pacing the room, and then fired off a second email to my boss telling her to just delete my earlier email as it was just boring photos meant for someone else. I talked to her several months later and she poker-faced told me that she never received it
"I really don't use that email address anymore." I'm 95% sure she was lying and now thinks I'm a sick pervert who likes naked disgustingly obese senior citizens.
True fucking story.