When I was in my mid-20s, I worked at a small company and sometimes my boss, a woman in her late-40s, asked me to housesit. It was a great gig--she had a great apartment in a fancy part of the city and I would stay there and feed her cat and order takeout. I always slept in the guest room and occasionally had friends over, but nothing too crazy--I knew the doormen were probably keeping some tabs on me.

One time when she hired me, there was some repainting going on in the guest room, so I had to sleep in my boss's bed. I also happened to have just started dating a new girl. She came over to hang out and was poking around. I'd always tried not to pry too much, because I didn't want to mess up a good thing. My gf didn't have that hangup, and quickly found the sex toy drawer. There was nothing too crazy in there, but it was a pretty nice collection of high end sex toys. At first we just laughed about it.

But then we smoked and got a little tipsy and started having sex and she got a gleam in her eye and got up and washed a few. And that's how I ended up fucking my gf in my boss's bed with my boss's plug stuffed in her ass and my boss's hitachi against her clit.

Pretty soon I got a new job, and that was the last time I housesat. I always told myself it was because I was no longer at the company, but I do always wonder...