Lubricant is an absolute must.
Repeat this technique of slow-in, slow-out five or six times, or until you can completely insert the toy.
If you're turned on by taboos and the power play experience anal can entail, that's valid too! Sit this one out if you have hemorrhoids.
There's a lot of fear-mongering and myths regarding anal sex and we want to clear the air.
Move around until you find one that makes you feel most at ease.
The wall between the vagina and anus is super thin, so anal sex can stimulate those hot-spots.