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On the Limit
For those that play and indulge their fetish with a partner, how do you ensure your tolerance is not pushed past your comfort zone?  Do you discuss things before hand and stick to that or maybe press on just a little further?  Do you have a safe word (how does that work with a gag)?  Are there postmortems where you can say that wasn't quite enough or it was too much?  How do you control things safely?
Always in strict uniform
I am fortunate in that Mistress interprets my reactions very well as to when pain moves beyond the threshold of pleasure. But if not I just advise her politely that my limit has been exceeded. I can't recall it happening when gagged, although as Mistress likes to be thanked politely after every stroke, I am rarely gagged for punishment.
Quite simply you learn has you go along.
With a new playmate you talk to them first, find out what they like and dislike. Maybe make some suggestions of your own but always respect their wishes.
Then comes the fun part! You gently test their limits pushing them to what they consider to be their limits and then when they use the safe word you stop. Feedback is essential especially if you will be playing with them again.
The more they trust you the more they will submit to you. Eventually you should be able to play without the need for a safe word, experience at reading body language is also a massive aid which is why it is worth the time and effort to get to know someone both in kink and vanilla.
While people have different views I would never gag someone until I was happy that I knew then well enough to read reactions and body language. Vigorous shaking of the head is what I would expect if my playmate was in trouble or distressed while wearing a gag.. Personally I would never leave someone who was gagged unattended. Also I would recommend anyone who was playing as a Dom to be a qualified first aider as you are the person who is responsible for the well being of the submissive.
Finally as with anything of this nature consent is everything so good communication and trust is paramount. That is why it takes time to build this type of relationship.
A sobering reminder that some fetishes do need to be played slowly and carefully, Yvette-Louise as some (such as gagging) can lead to unsavoury outcomes if not carried out in a safe manner.
Great post YL and some really good advice. In addition to what has been said it may be worth considering an alternative to a safe word. It sounds quite obvious but it does work. Simply by holding something in your hand and letting it go/drop when you reach your limit- ideal when using gags.

It should also be stressed again that gagging is not really a newbies game although there are many types of gags that make an introduction more pleasant. A hollow ball gag with cut outs is good as it allows easy breathing, as does a ring gag. Both however induce drooling so provide a waterproof bib! More severe gags will have breathing/feeding tubes to allow a good flow of air and some extreme gags incorporate nasal breathing tubes too.

Anyone care to suggest their safe words?
Always in strict uniform
No safe word necessary. But we use the traffic light system if playing and need some feedback on pain levels.
Know thy self, sissy.  Don't whine, don't pine, learn to expand your mind.   
Like sissysoft the traffic light system is my preferred way of working. Red is one of the best safe/stop words to use has it only has one syllable which makes it quick and easy to say.
But surely everyone goes directly past green, right?
Always in strict uniform

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