I have lived both sides of the coin your looking at.

I was new to the lifestyle, and had been playing with some very experienced submissives who gave me lots of good advice on technique with a variety of activities. As my experience level grew to what I now consider moderate levels, I have played with some very new submissive.

What I learned and have found most valuable is the ability to read the submissives body language. I find that doing this makes the experience so enjoyable for both me and the submissive. To read their eyes/hands/legs/feet as I am playing with them. Seeing when what I am doing becomes too intense so that I can temper the intensity, yet maintain their experience to a level they enjoy, as well as that I can have fun with.

So my advice to you is learn your submissives body/mind. Watch her during times your not in play together, and you mention those clothes pins in those tender places. Learn how to read her body as you play, she will unknowingly speak to you how she feels, and if your paying attention, you won't have to ask if she enjoyed it. It will be in her eyes that she is.

Two additional items that may help. Learn as much as you can about the safety concerns for the given activity you wish to participate in with her. If you know what would cause real damage, then you will have confidence your not going to permanently hurt her, you will only have to pay attention that you haven't gone beyond her ability to withstand the activity. The other thing you can do is an activity checklist (the others also mentioned this) do this on a regular basis as the two of you grow (both of you fill it out). This way you see where each of you are going in your likes and desires.

Remember, if it isn't fun.... Why the fuck are you doing it?

V/R
ID