Continuation of submission to a Straight Alpha Male

Hello again Brother. Thank you so much for your answer to my last question. It was very helpful. I am trying my best to prepare for what I hope to be the start of my submission to my Straight Master. I was wondering if you could give advice on 2 separate matters to this end?

First, I have read your preprepared letter and I cannot thank you enough for going to the effort of writing it to help us fellow faggots out. I was wondering if you would advise me to send it before the holiday, so he has time to read and process it? Or should I wait until we are together in the cabin? I am slightly worried it may scare him off or cause him to second guess if he is, as you correctly say, trying to be a nice guy.

Second, as any self-aware faggot should be I am locked in chastity. He is not aware that I do this however. If I am successful in submitting I will have no issue giving him the keys. But I do not want to seem presumptuous or predatory, and I am concerned that if he realises I arrived wearing it he may think negatively of how I have approached submitting to him. Any advice is appreciated, although I understand if you are too busy and only wish for updates once I have given him the letter