"Tickle your ass with a feather" joke?

Question

So I heard a joke about how one man taught another how to bring woman home. He said: "you casually walk up to a woman and ask her: 'tickle your ass with a feather?' If she gets offended, just cover by saying 'particularly nasty weather?' She'll think she misheard you and you move on. If she's up for some action, you can skip all the bullshit and get her home in no time."

The apprentice, of course, made mistake by saying "stick a feather up your ass??" to a woman. The woman was shocked and the guy was panicky, says..." uh ...it's pretty fucking hot out!!!" something like that.

But I could not understand why this is funny (neither "tickle your ass with a feather" nor "stick a feather up your ass"). Is it some kind of homophone or slang joke?

Can someone please explain?

Edited: Sorry for not being clear at the beginning. The context of the joke is about one guy is looking for advice about how to be successful in the bar, and he's got advice. What I don't understand is:

1. "tickle your ass with a feather?" is pretty vulgar, how could you cover with "particularly nasty weather?" it does not make sense to me, what could people misheard?
2. by searching for the meaning, I've found that "stick a feather up someone's ass" means to make him/her happy, which is probably the same thing as tickle someone's ass with a feather, so apparently the second guy did not misuse it (ref https://forum.wordreference.com/threads/feather-up-someones-ass.1428860/), then why is it funny?

Answer 1

(1) The two sentences have similar sounds in them (ick, ass, eather), so if the woman reacts badly the man can pretend that she has mis-heard a comment about the weather. Of course, it would only work if the weather was nasty that day!

(2) The 'apprentice' gets it wrong by using two sentences that don't contain similar sounds.

Answer 2

Though you understand it well enough to describe it here there is no way to explain to you why parts of it are funny or the result of the story is funny. You honestly tell us you don't know why it's funny. That is the end there. You clearly don't care for vulgar jokes so you will not enjoy it.

And yes, we should not be explaining jokes here.

For the record the first fellow describes a pair of Sound-Alike phrases that can be paired up to either beg excuses or get the desired response. It is the failure of the second fellow, too drunk to manage it, that makes the gag. He is intoxicated and so, bungles it. There is no homophone or other in joke to make it work.