Seeking advice for first timer

Hi M btw
Just got my first set of plugs. One small one and one larger one. Have experimented with objects in the back door before.

Now I have been using the small plug for a few weeks now, it fits well and is super fun but I have one concern when I sit down with it inside it kinda goes all the way in and it scares me every time so I always have a hand on it. So maybe I thought I had gotten used to it so I tried to size up but it couldn’t fit so I backed off and went back to the smaller one.

I do warm up and always use lots of lube and do an enema before anything begins.

Question?
1. When do I know when to size up ?
2. Should I invest in better quality/type of plugs ?
3. Should I do more warm up ?

Edit 1: I appreciate all the comments so far (20min after posting) learning a few new things ! And I apologise for being a noob at this please be patient with me. Thank you !

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