I really like the title of this thread and can think of two instances where this could have played out but alas didn't.
The first involved my ex Wife Karen who used to design and later sell low line jewellery, she employed a really camp assistant named Tim who I found irritating bitchy and overly opinionated, she on the other hand found him hilarious and would often encourage him in some outrageous antics and foul mouthed rants.
He took an instant dislike to me and seemed quite jealous if Karen and I went anywhere or planned anything that didn't involve him.
Karen quite enjoyed the fact that we really disliked each other and would purposely play us off against each other just to get a reaction.
I'm openly ticklish and she was well aware of that, and one evening she told me that he'd caused a scene with a customer that could cost her a potentially large order, so I urged her to either get rid of him or reign him in.
Her reply was "Keep on and I'll get him to tickle the crap out of you"
I instantly shrugged it off and said something along the lines of "You'd need him and a dozen more" taking the macho line and the fact he was only about 5ft 6" and nine stone soaking wet.
However she'd planted the seed and I've always imagined and still do about nasty Tim tickling me senseless while she watched.
Various scenario's coming to mind, with the kinkiest being me wearing nylon stockings or pantyhose, bondage, stocks, wrestling, being drugged, you name it, I've come (cum) to some sticky ends in those humiliating fantasies.
The other instance involves my Auntie and a rude antagonistic neighbour.
I'd known from a young age that my Aunt was Ultra ticklish (it must have been a family weakness) and I remember her regularly at loggerheads with her jealous neighbour.
My memories are always of them arguing and my Aunt coming out on top, with the other Woman always backing down, bitterly and resentfully retreating.
Then I had the shocking notion of 'what IF her neighbour found out' (about her ticklishness) which again lead to some wild thoughts and occasional dreams, one such idea I typed in the stories column. Link:
https://www.ticklingforum.com/threa...-bitch-f-f-nylon-feet-with-new-images.440249/
So yeah, this thread can open up a real can of ticklish worms.