Anonymous asked - "I was wondering, doesn't it get "boring" if the sub is completely obedient and does everything the dom asks without a mistake, and theres nothing more new to teach or punish?"

To be short, not at all. There is a huge amount of activities in the BDSM lifestyle that one can partake in, and not every submissive is naturally good at them. This means that you can train your submissive in a variety of different activities, and this, if done well, can take quite a long time. My kitten, although not a natural masochist, has an enormously high pain tolerance; this is something that we have worked on together as Dominant and submissive for our entire relationship. She has also been trained in many different types of submission “play”, from masochism as mentioned before to the basic levels of “pet play”.

Apart from training your submissive in the multitudes of different facets of BDSM, you can also work on what they already know; this makes sure that they keep their skill levels at their highest, as well as keeping them on edge. 

You will also find that with a lot of BDSM relationships, the boundaries that have been layer down at the beginning of the relationship will always be fluctuating and evolving; something that your submissive may not have been keen on may become something they are interested, or even eager, to try. This can happen for the Dominant as well; they may find that they are more sadistic then they previously thought, or even in some cases wish to indulge in switching with their submissive partner.

I and my kitten personally avoid this problem by constantly working on what she already knows and does, and constantly discussing when new desires may arise. New things to teach is never a problem, the internet is a vast source of all things BDSM and there are always people to talk to (Tumblr, Fetlife etc) who will be able to suggest new activities for you to indulge. As for new punishments, as long as you know what your submissive finds a true punishment, then it should not be a problem to find new ones. Most of the time the punishments can be drag out or warped into another form of punishment, adding in elements such as location and length of time.

Have Fun

Sincerely Sir