I Sexted My Boss…And Lived To Tell The Tale

No matter how many embarrassing moments I read in Seventeen magazine when I was younger, none ever seemed to be as embarrassing as the shit that happened in my actual life…If there were a “how to not get fired” manual, sexting your boss would probably be number one on the list. Then again, maybe it wouldn’t be on the list at all, because who would be stupid enough to think that sexting their boss would be a good idea?

Oh, right…me!

Charlie and I hadn’t been dating long, maybe about four months, but things got serious fast. As high schoolers with weekday curfews and bedrooms in our parent’s houses, we naturally had to get sexual in more creative outlets. When we weren’t having sex on abandoned golf courses, we were sexting. Mind you, this was long before the days of snapchat, and if you were sending a titty pic, you better trust whoever you were sending it to.

You should also probably check who you are sending it to, just in case you hit the wrong name from your contact list. Because in 2011, you didn’t directly send a photo in the chat, you had to send the photo from your library to the selected contact.

It was about 10:30 PM, past my high school bedtime of 9:30, and my 17 year old boyfriend wanted “a pic” of me before I fell asleep. Being my spunky and sexual high school self, I turned on my light, quickly snapped a shirtless photo of me half-asleep (messy bun and all) and typed up a corny, loving message to send along with the photo.

As I sent the photo to whom I thought was my boyfriend, I quickly realized that I had made a mistake. I didn’t send the photo (and accompanying message) to my boyfriend, but the assistant manager at the restaurant I worked at over the summer (who just happened to have the exact same name).

Panicking, I called my boyfriend blubbering about my mistake after quickly deleting the message and photo (as if that would do anything to stop the horror that just occurred). My boyfriend, naturally, nonchalantly asked where the pic was, cause I never actually sent it to him.

After calming myself down and eventually falling asleep, I woke up the next day to a text from my manager saying, “Uh, I don’t think you meant to send that to me.” Well, no shit, Sherlock? I can only thank the heavens that it was winter when I sent the photo, and not in the summer when I would have actually been working at the restaurant, and training under the man who had now seen my tits.

So did I have to search for a new job and awkwardly explain to my parents why I would not be returning to my great summer job? No, instead a miracle happened. After conversing with a co-worker I found out that Charlie (the manager, not my boyfriend) had been relocated to another restaurant and would be replaced this upcoming summer. I went back to work that summer, and although Charlie came in from time to time to pick up things, it miraculously never happened during one of my shifts.

Today, I have largely forgot about the horrors of my sexting mix-up of 2011, but I do have Facebook to always gently suggest my old manager Charlie on the “people you may know” section. I wonder if he sees my Facebook page and remembers how I accidentally sent him nudes that one time…And I wonder how I’m still so careless about sexting to this day. If my tits ever resurface on the internet when I’m rich and famous, sorry I’m not sorry.

Gimme More Sex + Dating

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