I have had ups and downs for the past 2-3 years, but now I'm about to date a straight guy who's REALLY into me (and knows I'mtrans) and I really like him so far as well, and the topic of anal comes to my mind again.

I know anal requires a lot of trust and respect in order to relax your body, but what would you recommend me to prepare myself if that day comes?

I have 3 sizes of silicone plugs that are very comfortable to wear (the largest I need to warm up to). They are 2.8, 4, and 4.5 cm in diameter. A former dom said that that should be good enough. Do I need to wear them daily or...? If I do, would glass or metal be better for hygiene purposes?

I also can't seem to orgasm from anal only. I can, however, finish myself by doing the last 5 to 10 seconds anally using an njoy wand. I'm hoping that practice makes perfect.

Does anyone have any recommendations to essentially help me with sex life? I know anal is not the one and only thing in the toolbox, but I want it to be awesome for both of us. Anything that I can do to prepare my body is very appreciated.