While the endless ass pics and reposts are annoying (personally I like the clothing aspect of things), I think it's a comfort thing.

That makes sense, but then the issue of it stifling new content comes into play. Why bother making new stuff when everybody wants the same old thing?

Part of the reason I don't post pics is because A. I'm pretty sensitive about my look and B. I'm not comfortable having a lewd picture of myself on the internet. It may never come back to me but there's still a chance that someone may recognize me.

I completely understand that. My pointing out all the ass pics wasn't to suggest we need more lewd pics of people, especially if they're not comfortable. It was to bring attention to the fact that people would rather post uncreative, repetitive things, rather than new content.

I do agree though, subs like r/sissyfitness have gone a long way from what they used to be

Which is really the fault of the mods, which is sad. They were great subs, but for whatever reasons, the mods didn't enforce the rules and destroyed good communities.