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What would be a good anal toy for trying to get into trying anal sex for the first time
The common recommendation for beginners to anal sex is to start with small stuff, slow tempo and a lot of lube!
When it comes to anal, there can't be too much lube.
If a small plug still hurts your partner, using a finger for a start is a good way to go.
Also, your GF just may not feel completely relaxed, and this could be the reason of pain. I guess, in this case, open discussion about her concerns, setting the scene and choosing the proper position where she'll feel more comfortable and relaxed would be helpful.
You may try using the smaller butt plug. There are a lot of various kits for beginners which helps to work the way up, such as Booty jewels beginner set
, Booty explorer silicone set
or Love you back kit
And I suppose it may be interesting for you to learn some info about preparation to anal play
, anal play itself
, how to choose