Anal play is safe and comfortable when you respect three rules: a flared base, plenty of lube, and patience. Problems almost always trace back to skipping one of them.
The flared base rule
The rectum does not have a natural stop. Anything you insert needs a base wider than the toy itself so it cannot travel. Every anal toy we sell has one. Do not improvise with anything that does not.
Lube, and then more lube
The anus does not self-lubricate. Use more than feels necessary and reapply. Water-based lube works with every toy. Silicone lube lasts longer and is a good choice with steel or glass, but keep it away from silicone toys.
Start small and size up slowly
Begin with a plug around one inch in diameter. Wear it for short sessions, a few times a week, and only move up when the current size feels easy. Most people take several weeks to move up one size. A training kit with three graduated plugs is the least wasteful way to do this.
About prostate massagers
Prostate toys are curved to press forward toward the belly. The good ones stay in place hands-free and have an external arm for the perineum. They are a comfortable second purchase once a medium plug is easy.
Cleaning
Wash with warm water and soap or a toy cleaner immediately after use. Non-motorized silicone, glass, and steel can be boiled for a few minutes. Store toys separately so materials do not react with each other.