Beginner's Anal, Sissy, Crossdressing and Stretching help and advice!

Hi,

I'm currently working my way up to a stretchy and loose butthole. I want one so bad, I practiced before but because of work and life and meds I have to take long stretches of time apart. I want to re-visit this and accomplish this personal goal. I also love CROSS-DRESSING & SISSY RELATED THINGS

1. Does a gaping stretched well-taken care of hole go away if its not maintained properly ( stretched every SINGLE DAY for hours)
   
   
2. Is there a schedule I should make?
   
   
3. What toys should I get? I have no dildos just butt plugs!
   
   
4. How can I avoid making an accident using a hollow plug ( really considering using these graduating sizes )
   
   
5. How long do I need to be constantly stretching to take REALLY BIG TOYS?
   
   
6. What can you take in width, are you proud, and how long did it take?
   
   
7. How did you become a sissy if you are or an anal addict and what steps did you take?

List of My Toys​

1. Doc Johnson Red Boy (Easy)
   
   
2. Tantus Ryder (Easy)
   
   
3. Collins Speculum (Love to see my ass gape so wide, can only hold it up to 2 minutes larger and larger!)
   
   
4. Ballistic Metal Size Small Anal Stretching Plug ( Hollow Plug )
   
   
5. Generic Gradual Plug Set (Only bought because the largest one was larger than red boy at the time)
   
   
6. Doc Johnson Mood (My first EVER plug! in Large - Piece of Cake! I Hesitated then fell in love with anal after trying this!)
   
   
7. Icicles No 27 (I can take this, but it's more like a dildo and not for as long as my other plugs)
   
   
8. Icicles No 26 (Take this easily)
   
   
9. Doc Johnson - TitanMan Rumpy ( Cannot take this fully in, extremely stiff and extremely wide and bulbous, very rigid even with tons of lube, working my way to this! )
   
   
10. Steel Large Cute Turquoise Diamond Plug (1.6 in width, my go to favorite that my ass loves. I love to use this to warm up to my Ballistic Metal Ass Stretcher and lay on my bed with a towel under)

I also wanted to get a Doc Johnson TitanMan Intimidator to stretch my ass with one thing + the value and price of it. Thoughts? what should my next approach be. Also into being a sissy!!!

EDIT: I want to sleep with my plug in my ass tonight, I'm really gonna try very hard. my diamond 1.75 diameter one.