To start, small toys like butt plugs and lube. You can buy larger toys as you get more comfortable with the current size. That's about where my knowledge ends... I'll leave the rest to others who know way more than I.
Typically it is best to adjust using sized toys(you can buy kits) and butt plugs to get used to the sensation and pressure commonly associated with anal penetration. The idea here is to go as you're comfortable and progress to sizes large enough to allow for intercourse. LUBE LUBE LUBE. Especially while beginning (and often under all circumstances) this is your best friend. Any more questions or anything just get at me. This is sorta my area of expertise lol
But yeah, lube like there's no tomorrow. When you think something is small enough to go in without lube, you're wrong. Work your way up over time.
Originally Posted by RJinLR
If done correctly you should experience only a minor discomfort usually from nervousness and adjustment to the sensation. It will be new. Stop as often as you need. I recommend going with a bead to that has different sizes on it before you start with the different plugs and trainers.
Typically if starting no yourself the best position is on your side almost with one leg hiked. This forces certain muscles to relax and provides more control over entry for you and your training toy