It's called stumping.

I'm pretty sure this is from House of Gord, which was an early (late 90s/early 2000s) BDSM website run by a now-deceased perverted engineer who kind of saw these contraptions as both a challenge and sort of the cutting edge of kink. That's 'cutting edge' as a figure of speech btw, nothing to do with knife play, which is its own separate fetish.

There are other gifs and pics that crop up here from time to time from the Gord days, a lot of latex play and chaining girls to treadmills, putting them on bicycle-powered chariots that simultaneously diloded them as they pedaled, other bizarre stuff I don't even know how to describe... The outlandishness was part of the fun, I suppose.

Most people who enjoy jerking to this stuff don't actually practice it in real life, the equipment is costly and it's time-consuming to get in and out of it, plus it's pretty niche even within BDSM. The 'basic' version of this is basically just latex play; there are rope ties you can do that create the same effect as in the pic, but again, it's time-consuming. Much easier just to use a collar and leash and throw some bondage in for a similar effect.

To answer your question, you're basically looking at the equivalent of a BDSM porn art piece. The people who are involved in this are either paid for it, like the model, or they're at the more extreme end of kink and have always been there in one way or another. I wouldn't really call it a rabbit hole for practitioners; the more you get involved in BDSM the more you realize how exhausting, impractical, and expensive stuff like this is.

/r/WTF Thread Parent Link - i.imgur.com