I was going to write something clever, but the Stranger column ate my brain. So I'm not.
However, I got a sweet email asking me about buying one's first flogger, and that's a question I can answer even with no brain. Nervous beginners, what you want is a deerskin flogger, with tails that are not too long, no more than sixteen inches.
Deerskin is very light and soft, and I swear to you, you are not going to really hurt someone with a deerskin flogger. (Unless you poke them in the eye with the handle or something, so don't do that.)
I recommend this one. The Bare Leatherworks guys make lovely floggers. I’ve bought a number of them over the years. I find them very well made, pleasing to use, and they have held up very well to frequent – and often not gentle – action.
One step up in intensity from deerskin would probably be this one, the cowhide flogger. Still pretty soft and pleasantly thumpy, though.
Anything with rubber tails is going to sting and be more intense, and be more likely to leave marks, so I generally don't recommend rubber floggers for a beginner.