To add some context, I have always been aroused by how nice my girlfriends anus is. However it has always been a bit of taboo for me, but at the same time it was what made it so intriguing. Her favorite was for me to go down and give her some sloppy passionate oral. As I was licking her pussy, I decided to give her anus a lick. Her body jolted with excitement as I teased it with my tongue. It was funny because she would always act like nothing happened. Every-time as I went down, I felt her hips move closer to me while exposing her asshole. so again I would lick it but this time I generously wet my finger and stuck it in while while I gave her some doggy. Afterward, she brought it up. She was like, it was a bit different but I really enjoyed it. further down the road, she ordered some training plugs and wanted to move up in size before we gave it a go since I'm a bit on the girthy side. When she was ready, we decided to get a room and some drinks and was really set on trying it. I licked her asshole as usual then firmly pressed the plug in (she confirmed she was ok). After some foreplay, she removed the plug and applied a generous amount of some special lube we had for anal. As I pressed against her, I felt her push back. With every thrust, I felt my penis gliding more and more in. The rhythm gained a-little bit of momentum . We had anal for about 20 min, it was amazing. I checked in on her and she was ok, she wants to do it again.