You're probably not getting much lube inside, your natural mucus is dry-ish, and any lube that does make its way inside is being dried out by your rectum.

There are a couple immediate possibilities to help here.

One thing is to make a "lube shooter". Get a infant's oral syringe (the kind with a plunger and a tip that is very rounded) and squirt a couple of ccs of lube into your rectum. This is probably the most direct option.

The second is to use a small water enema first. This isn't as direct, but I find that after I use an enema my naturally occuring mucus is much more slick and my rectum doesn't seem to dry things out as rapidly. Wait about 45 minutes after the enema (it can be very small, about a cup) before you have anal sex.

There are also a couple of generic things to keep in mind.

If you're dehydrated your body will snap up moisture faster. Make sure you drink enough water.

Sometimes your choice of anal sex positions will cause the toy or penis to poke the wall harder than others. If it is still a problem after trying the lube shooter you might want to try a different position. less

Oh no, I have the lube tubes. (I wrote a review on them even) I use it every time. I don't know if it's nerves or what.
I've never used an enema though. It might be worth looking into. But I thought those were just for cleansing your body so you don't make messes. I've never had that problem, unless I use beads. So I don't find it necessary.
Thank you for your advice though. I'll look into some new positions as well. We always use the same one because it makes penetration easier. less