Yay, Celestia is teaching him and he's learning!

Good one, Anon, you're a fast learner! Soon Rarity won't mean shit to you!

Wow, now that's something, I wonder if she meant all those letters to be a self-help book or something?

Wansered through your gallery on impulse.

You know, it occurs to me that Celestia is sort of manipulating him as much as anyone else. Especially if social niceties are raising to the point of manipulation, her pointed questions about trust come to mind. She leaves him a door out, but that's always sort of a bogus thing because if you know someone is insecure and doesn't want to be Outside the circle, any escape from it becomes just a way of subtle blackmail... Or genuine encouragement. They are different but they can look so similar.

A man chooses and a slave obeys https://tenor.co/vRfz.gif

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The thing is, the safe word and way out in a BDSM relationship (of which Anon and Celestia are effectively taking part in) is not a form of discouragement or blackmail. It's an option for BOTH parties. either one of them could back away at any time, and the other party cannot guilt them for it, operative word being cannot. Why? because the entire relationship, like most relationships, is inevitably built upon trust. If a dom keeps going when a sub doesn't want it, that breaks the relationship and creates mistrust.