Perceptive forum discussions on Butt plugs:

Rear ender – butt plug
I just got this today and it is HUGE. Is it just me, or am I the only one who cant find a just right size for me? I ordered one that was TINY and this

I got an "ask me" button!
It's the little things in life...(and I am going through a personal crisis) EF sent me an offer to review a new product that is not yet available...

Plug for public fun
So it has always been one of my fantasies to have an anal plug in while in public, and even better - one that can get me off. I tried looking around.

Ace Of Spades Shaped Butt Plugs
Does Anyone Think That These Shaped Butt Plugs Are Better Than Any Other Shaped Butt Plugs? Example: Does This Particular Shape Cause A More...

Custom items/Piggy plug
This is sort of two questions wrapped into one. I have been desperately wanting a pig tail butt plug. Such a thing exists except: 1)they currently...

I'd stay away from rubber - the small silicone butt plug would be my recommendation.

A gloved finger will be a good start, use plenty of lube. Once you are comfortable with your finger then look to something made out of a good safe material, like silicone.

The biggest thing to learn is how to relax the anus, once you can do that the toys will provide more pleasure. Remember, anal play should not hurt! That is why fingers are a better way to start. You can better feel what is going on.

I agree with dwtim. start with a pinky finger with lots of lube and move up from there. If you find it is something you enjoy, then look into buying some anal toys.

I also suggest starting with your finger/s and moving on to a silicone toy if you decide you're ready for something larger.

After you're used to a finger, the small silicone would be better than the rubber. I agree with gunsmoke and everyone else.