Will anal every get easier?

I want to do anal, I love the idea of it however it has been very difficult for me. I tried it for the 3rd time today. The last time I tried was about 1 year ago and it was so painful I cried but endured it.

I got descensitizing lube, anal douche device and a butt plug. I used all 3 today but it was still so painful. At one point the burning sensation was gone but each stroke just triggered this strange pressuring sensation I could not endure. It made my leg go numb and I was sweating so much. I had to stop.

I want to really be able to do anal comfortably. Will it get easier with time?