Dear jade:
There r many factors that make anal sex easier & more enjoyfull for u.

1- The lubrication: use as much as u can & choose a proper one
I think the best lubricant u can use is KY jelly or Moisturizing face creame. Don't use petrolium jelly (vaseline)!

2- The position: it's one of the most important factors in anal sex!
to my expirience the best position is to lay on ur back get ur ankles with ur hands and pull them to urself as much as u can
the other greate position is doggie style.

3- Relaxation: Remember! the more u think the less u enjoy!Just lay down and relax.The stresses may cause ur sphinctures tighten and cause a lot of pain. just relax and enjoy.Having an enema will help u alot for relaxation

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Just think!
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Burice Stravinskey