In the early days of phones with cameras I went to a class on incident command systems. There were people from fire, law enforcement, OES, and such there. This one female cop and I hung out some and were chatting. We exchanged numbers but I was not thinking anything would happen. Around midnight she sent me a picture of her tits asking if I wanted to see them in person right then. I had a girlfriend (now my wife) at the time so I declined.

More recently someone at work got drunk and sent me a short video clip of her doing topless jumping jacks. I totally did not see that one coming. I did not reply and she never mentioned it.

Coworker on her own work trip.
 

I had a coworker Kate I worked with for many years. We became friends and pretty close. We never went beyond normal friendship things as we were/are both married.

We were both on work trips for the same company, in different cities. I traveled to the midwest and she traveled to the west coast. We had a three hour time difference. I get a call around 3am and its from Kate. Kate never calls this late, so I picked up out of curiosity. The phone call is from a tipsy Kate. She tells me how great everything went, even got a few clients out to the bar to celebrate. She asked how my trip went. I mumble something because I'm not awake yet. She gasped and started apologizing because she didn't realize it was 3am where I was.

I told her not to worry about it, I had a 7am flight, so I would be getting up soon anyway. She started talking again, a mile a minute and then stopped and apologized again. I told her it was ok. I knew she was really excited and very tipsy. She asked me about my trip and I told her it was fine, but I was in BFE with absolutely no night life on a Friday night. It was probably the most boring trip I had done. I was being dramatic. She continued to tell me about the night for a few more minutes and then said she was going to hang up. I was wide awake by that time and told her I was going to get my stuff packed and jump in the shower. She said maybe your day will look up after your shower and said goodbye.

I showered and when I got out, I had a text message from Kate. It said something like hope you have a better day. The photo was attached. We talked about it at a later date and she said she was very drunk. She worried it would make things weird. I told her not to worry and that I had deleted the photo.

Fun story.