try and play with your self first. use lots of good lub. start with your finger and play with the out side. most people tend to tese up when first playing with the back door. so the more you play with it the more relaxed it will be. then when your ready put a finger in. ther are to spinkters the first one is easy to relax the 2nd one is a pain. dont rush take your time. when you have one finger in try moving it inside you and feel around. this helps me relax more. also try and push lightly as if going to bath room. then i like to put pressuere in a circle motion with one finger and seems to help me alot. then when your ready put two in. and work up to 3. i need 3 before i git pegged and she needs 3 before i put my joy stick in. Also when he is trying to put it in after you properly wormed up try taking deep breths that helps.

o and cut your nails thay will grow back. and use a hand glove its a bit smother

Make sure there is plenty of touching outside before any penetration takes place. Ask him to pay some extra attention to the area during oral, gently sliding a finger inside. Not sure how much anal play you've done or if its all new to you.

Also, I'd suggest starting off with a slim toy. I had a very slender vibrator that I absolutely loved. It died and I haven't found a replacement

When you do go all the way, I suggest a good lube (We LOVE Maximus) and open communication. Make sure they go slowly. It might feel uncomfortable at first but it should never hurt. Don't be afraid to speak up. I have only done anal with two partners. The first I absolutely hated every time because a)I didn't speak up when I wasn't comfortable and b) even if I did speak up, he never seemed to mind. My husband now is so in tune with me and my feelings that if he senses something isn't right he stops even before I say anything.

Good luck, have fun and don't rush into anything before you are ready!