There won't be much discussion between Anon and Celestia about boundaries, but she isn't exactly going to mold and shape him either. She's going to push his boundaries, but if she comes up against a line that he refuses to cross, she won't force him over it.>>30034508
The horsedong is going up Anon's ass eventually, but it'll take a fair amount of time before she's laid the groundwork and prepared him for it. She doesn't want to fuck Anon in the ass with a strap-on, she wants Anon to want her to fuck him in the ass with a strap-on. She knows that he likes being dominated by mares, and she knows that he likes having things put up his butt by mares, she just needs to make sure that he's ready to be mounted and bred by a mare.>>30034521
Basically the first part was him being paraded around a public area in women's underwear and having a buttplug stuck in him, so you could argue that it's already at that point. Celestia isn't going to be verbally abusing him, chaining him up in her basement, forcing him to lick her hooves clean, or whipping him until he's gushing blood anytime soon, if that's the kind of stuff that you're worried about.
That being said, I should offer the huge caveat that I'm not even a hundred percent sure if I'm going to continue. I'll try to continue today or tomorrow, but don't be surprised if this is all you get. I have no shortage of ideas, but that's part of the problem: I just want to write something short, but I've got a fucking novel's worth of stuff I'd like to put into it.
But anyway, the hypothetical next update won't be about stuff going into Anon's butt. As for the also hypothetical future beyond that, how do you guys feel about aftercare? I'd love to write about Celestia pushing Anon a little too far and spending an evening bathing, cuddling, and comforting him to make up for it, as long as people would also like to read it.