Has anyone actually fucked their boss or have thought about fucking their boss?

Yes but that's not what I first thought of when I ran across this thread. A friend of my wife's discovered her husband cheated on so she fucked her boss in revenge. It turns out he "had feelings" for her so was pressuring her to go further. Long story short she divorced her husband and married her boss. After nearly 15 years of paying for his step children (including help with college financing) she divorced him and remarried her ex-husband whom she'd been fucking all along.
Plot twist
 
My wife was owned by one of her bosses, about 14 years back. At first they would fuck in his office. Later he got so demanding, he would just text GPS coordinates and she would drive to his car and blow him. He would demand she wear a miniskirt with no panties during these encounters for “easy access.” At the very end, he wouldn’t even drive off the company lot. She would just suck his dick in the parking lot every lunch.

Often he would command her to ride him to completion. And he would take her panties after, so she had his cum running down her legs the rest of the day. He also liked to cum in her mouth, or on her tits and have her rub his cum into her breasts. Perhaps my favorite detail is that he trained her to thank him for his cum each time.
 
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He wasn't technically her Boss, but his Dad owned the company. We were both on her company's softball team and had games once a week in the evenings. Afterward we'd all go to a bar. Sometimes our babysitter had to get home early to do homework, so I'd head home and my wife would stay and catch a ride home later, since they were her co-workers.
One nite she didn't get home until 4 a.m. I saw her sneak in, but pretended to be asleep. I told her at breakfast I'd gone to bed around 11 and asked what time she'd gotten back. When she lied and told me "around midnight", I knew something had happened. Checked her panties in the laundry and they were stiff with dried cum! Neither of them knew that I knew about it, so I stayed quiet and let it continue.
Spoken like a true cuck ;)
 
My wife was owned by one of her bosses, about 14 years back. At first they would fuck in his office. Later he got so demanding, he would just text GPS coordinates and she would drive to his car and blow him. He would demand she wear a miniskirt with no panties during these encounters for “easy access.” At the very end, he wouldn’t even drive off the company lot. She would just duck his dick in the parking lot every lunch.
This sounds hot
 
Oh yea, I've actually had thought of fucking my former boss. She was all that and then some. Huge tits phat ass. I wanted to fuck her ever since I was hired as her assistant. She's a short white woman at that.
 
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Mrs Playin has had dinner and went back to her sisters bosses house with him... Older man who allowed us to use his ranch home many many times over the years. In fact we've used his ranch and particularly his pool there to shoot many thousands of photos through the years. He showed up one day unexpected and actually saw us doing a pool photo session. She did it probably to thank him for being so gracious with him 2nd home. This is one encounter where I have no idea what actually happened because she didn't talk much about it afterwards. I know she came home with a rather large dildo and I expect that she "used' it for him or let him use it on her. Did he fuck her, I don't know for sure, he's be a fool not to have at least tried regardless of his age. I know he took care of her well for the time she spent with him... I later tossed that dildo to her one day when she was in our pool at home. I told her I wanted to see her use it for me and that she couldnt leave the pool for extra lube, not not that she ever needs or uses lube anyway except when I fuck her ass.
 
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