This is such a great question. Honestly, every punishment offers a great deal of difficulty because i know it means i have disappointed Master. Because Master incorporates many different kinds of punishments, i find many of them difficult in different ways.
Emotionally, i would have to say that being denied the privilege of serving Master is most difficult. To know that i have disappointed Him so much that He feels it best to not have me serve Him is absolutely awful. It makes feel sad, ashamed, and lost.
On a humiliation level, having write about my transgressions is absolutely the worst. In the past Master has had me write about what i did wrong, why it was wrong, what i should have done, and why i won’t do it again. These writing assignments are awful. The entire time i am writing it, i know the answers and i know that i knew better from the beginning. These are humiliating for me because it is embarrassing to know that i made a mistake that was totally unnecessary.
Physical pain is also very tough. Master has used a variety of implements for my spankings. This far Master has used His hand, a hairbrush, His belt, a metal spatula and the wooden handle of a bath brush. i will be and say that i have not felt the full force of all these implements. Master took a while to get used to the idea of inflicting physical pain on me (a result of 30 years of being told to never hit a girl.) Lately, Master has really come to understand the importance of the pain within O/our dynamic. Master chooses the belt most often as it is handy. my least favorite is the metal spatula as it is very large and covers a great deal of skin. The spatula offers a swift sting over a large area and offers no flexibility to soften the blow.
Every single punishment is difficult. If it were easy it wouldn’t be very effective. Each and every punishment leaves me feeling ashamed but loved. (For more on my feelings during punishment please read this blog post.) Master is always looking for more punishment ideas to add to his arsenal, so please feel free to share you favorite punishments, or least favorite as the case may be, in the comments section below.
(thanks STAR for the great question. i enjoyed really thinking about the different punishments and putting my thoughts on paper.)