To make your first steps into anal sex pleasurable and safe, there are common rules for beginners - go small and slow.

For the beginning, the better choice would be a tapered, smooth, small plug made of safe material like silicone. Something like Sweet Love, Classic Butt Plug, Back Play Gem.

If you're not sure what size will fit you the best, you may look towards anal sets for beginners, for example Love you back.

Regarding lubes, first of all, they are a must for any anal play! Oil and silicone-based options have are great because they have a thick consistency and are long-lasting, but they don't work with all types of sex toys materials.

Water-based lubes are versatile, safe for any toys and condoms and very easy to clean up. So if you're going to use silicone toys, water-based lubricant would be the safest bet here.

Don't use desensitizing lubes, because if your session is becoming harmful, you won't feel anything.

As I said, trying anal you should go slowly, gradually working your way up. Stop with the first signs of discomfort.

Do's of doing anal:
- do some cleaning before;
- use a plenty amount of lube;
- go slow and take small steps;
- reapply lube if necessary;
- be aroused;
- be relaxed;

Don'ts of doing anal:

- don't use things that are not designed specifically for anal play;
- don't switch from anal to vaginal/oral sex or use a fresh condom doing this;
- don't have anal sex if you have health issues in that area (hemorrhoids or tears, etc.)
- don't apply any force.

Info about the best toys and techniques you may find in our comprehensive guides:

- Anal sex for beginners;
- How to prepare for anal sex;
- How to choose anal plug;
- Best anal sex toys

I hope this will help!

Best of luck!