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^^^^ In moderation. You don't want to be impairing your judgment or affecting your ability to feel pain. But a little extra help in loosening up, if you need it, is ok.

Also I should have mentioned health and cleanliness. This being the place where poop comes from, good idea to explore the area AFTER a bowel movement, not right before. I like to have a small enema before doing any play, but your mileage may vary. If you do, the ordinary Fleet disposable enemas are fine, but tip the solution out and just use ordinary plain water. It also depends a lot on diet - try to eat a healthy, high-fiber diet. A high-fiber diet is also good to preventing bowel cancer, so it's a win-win situation really.

Also with lubes, you obviously want to stay away from oil-based lubes if you're using a condom. Water based lubes are fine, but tend to get tacky or sticky and often need reapplication. I've found the best lube for anal sex is silicone-based lube, but be aware you can't use silicone toys with it or they'll deteriorate. I also recommend against Analese or other lubes that "numb" the area - you need to be able to feel if there's pain or discomfort so you can tell him to stop, slow down or whatever.

Also, for best results, take photos and post them on Pixies. And tell us how it goes