At least twice
It has at least happend on two occasions, both times because my girlfriend is a bit slopy with her phone. The first time it happend was when me and my girlfriend just hade started dating 4-5 years ago. She had been to a consert during the weekend and she was showing some pictures from it to some of her colleagues, only girls. After the last picture from the consert a picture of her self popped up and it showed her posing fully naked in front of a mirror with a sexy face. She was a bit embarresed but since she knew her colleagues quite well it was not that big of a deal. They mostly laughed about it and teased her for a while.
The other time was during the summer in August last year when she was visiting her parents in an other town. Her parents were working during the day so she was home alone in their house and decided to tan in their backyard. She usually tans topless but since no one else was there and her parents backyard has almost no insight she also went bottomless this time. During the day she got turned on laying naked in the sun so she sent me some naked pictures of her while I was at work, everything from her just being naked in the backyard to her rubbing her pussy. Later in the evening she was showing her parents some photos she took before she started tanning and the same thing happend now as when she was showing pictures to her colleagues, a naked picture of her popped up. Luckily for my girlfriend it was only a picture of her laying naked and tanning in the backyard and not a naughtier one. But still, she was embarresed as hell, much much more then when the same thing happend with her colleagues.
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