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What's the worst sex you've ever had?
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From your mom.
Seriously though, I was on the rebound from my first girlfriend with some tramp I met online. We didn't go on the conventional "date" we had scheduled. After I picked her up, we both agreed in going back to my apartment and got down to business. Eventually, while doing her doggy style, I was pounding her so hard and fast that I slipped out of her vagina and right into her ass. Personally, I was too busy on the job to tell the difference but then, she looked back and said "So, you like it there, huh?". I was confused, looked down and still recall the horrendous smell of shit that wafted up to my nostrils.
I had her jerk me off after that and then 10 minutes later, brought her back home.
I'm sure many have had much MUCH worse, but that's probably my "worst".