First of all there is nothing to be afraid of. I'd definitely take time and explore myself first before letting anyone near the ass. It doesn't cause hemorrhoids unless you do it daily like 50 times

However really go and try yourself, I have a suggested list of toys you might try. There are also videos and books by Tristan Taormino like the The Ultimate Guide to Anal Sex for Womenthat will help you understand your anatomy and the pleasures connected with it. Anal sex is great if done in the right way, if you rush into that, believe me it will take a lot of time before you try it again.

Here is my beginners post about the toys:

Think big - start small If you want to get into the anal play area with comfort and ease I guess the best thing is to start with smaller dildo like the:

Blush UR3 Anal Starter

or a silicone alternative:
Sedeux Please

To grow up I'd suggest:
Pure Skin Player jr

The silicone alternative is:
VIP Super Soft

For Butt Plugs:

The best training of all times (after you grow out of the beginners toys):
Triple Ripple

Best Butt Plug (I guess many will agree):
Ryder

And finally my personal favorite among plugs:
Gapers Organic

Generally speaking that's my product advice. For lubes you have to look for yourself what suits you more. Just don't use silicone lube on silicone toys, it really kills them. The rest as usual, hygiene, foreplay, foreplay, lube -> and plenty of fun

I hope that you will have lot of fun on the way. Try to involve your partner first with toys and later on get it done