Anal Is Fine On My Own But It Hurts With My Girlfriend?

I am a bisexual male and I love anal. I discovered I was into anal roughly 3 years ago and I often will finger myself or find something to insert when I masturbate and it enhances the orgasm and sexual pleasure tenfold.

My girlfriend of nearly 2 years and I have tried anal a few times and for some reason when she fingers me or uses a toy on me it hurts, but when I do the exact same thing to myself it feels great.

It is not a stretching type of pain though, it feels more like too much friction and almost like we dont have enough lube, but when my girlfriend fingers me we use more lube than when I finger myself. AND she has tiny fingers compared to mine. Have you ever experienced this before? And if you have what did you do to fix it?

(P.s. when using toys it is the same story. The toy will feel great when I am alone and put it in myself but when I am with her it hurts for some reason?)

 

any chance you're more relaxed when you're with your by yourself? I had one of my exs that could milk my prostate and it was amazing but the next ex it wasn't the same at all. Lube or no lube it wasn't the same. The first ex could lick her finger and it never bothered me but the last one could put lube and it wasn't the same
?