Before you go to sleep, can be in a bathroom, insert as many fingers as you can from both hands. Pull yourself open and stay like that for two minutes. At least you'll get a bit of stretching then.

Sorry for the late report, life got a bit hectic. I did this at my friends house, however I have not been keeping up with using my inflatable dildo each night because I've been forgetting. Should I start back at the beginning of the process, or is there something else I should do instead as punishment for not doing as I was told?

Start from the beginning. I expect daily reports, either here or by PM. Each one you miss will incur a punishment. Also add to your signature some dislikes that can be used as a punishment.

Wear nothing at all till you get dressed in the morning. Before bed you are to drink three pints of whatever you like.