The experience of trying to write Humor & Satire

A lot of the stuff I've published on this site started with the desire to push myself and try something new. Humor & Satire has always been a tempation, and I finally have something I think I'm ready to submit. But more so than anything else I've written, I have close to absolutely no idea what the reaction to my story might be. Will people think it's funny, sort of mildly amusing, or just a miss entirely?

For those of you who have tried writing something in Humor & Satire, what was the experience like for you? What reaction did you expect from your story, and what reaction did you receive? Regardless of audience reaction, were you happy with the result?

For those who have been tempted, but haven't done it, what holds you back?
Writing humor is like telling a joke at a party, you never know if it’ll land or flop. I’ve tried it, and honestly, the reactions were all over the place. Some people laughed, some shrugged, and one guy said it was “quirky” (still not sure if that’s a compliment). But hey, if it made *me* laugh while writing it, that’s a win. For those holding back, just go for it worst case, you’ll have a cringe-worthy story to laugh about later
 
I've been working on a satirical story, it'll be my first attempt at the section.
 
Mine sat in my unfinished drafts folder for months, both waiting for me to figure out how to end it, and also because I was feeling like I needed to add more jokes, even though it was seemingly more satirical than laugh out loud funny.

In real life some people think I’m funny, others not so much. But I’ve bitten the bullet. The Lit readership will soon get their chance to weigh in.
 
I have a story in the "How to" section of Lit called "Shopping for Sex Toys at Walmart". It's a winner and it's pretty funny, too.
 
I’ve written a H/S story currently sitting in my “in progress” file. I think it’s funny. It’s sexually explicit but isn’t going to get anyone turned on, though. I’m reticent about actually publishing it, though.

The bigger problem would be the description line. It’s a one-act play set in 12th Century Canterbury, England. It involves a particular sexual/legal practice that could be comedy gold mine. It’s by far the most out-there and unconventional thing I’ve ever written.
 
Well, in my previous incarnation here, I hit a mother lode with a humor and satire story that topped the list for a couple of years (and garnered green 'E's, meaning it tickled Laurel's funny bone, which helped its popularity).
It was very funny (I still read it and laugh, years later) , but not at all sexy. I've yet to see a story that really manages to both make me laugh and is hot. I'm sure it's possible.
 
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