Hey Piper!
I've only done anal a few times. Years ago, I had a few three-ways with a couple. She was totally into dp with her boyfriend and other guys (like me!). She was a very hot little Latina, and very petite, like you, with a very tight little asshole. Her boyfriend loved to take video of us going at it and show it live on the internet. This was in the late 90s, and I don't know exactly how he did it. Kevin and I named dp with her a "Jenna sandwich." She loved the term almost as much as she loved being fucked in the ass. At first, she always wanted us to cum in her ass, but we started cumming on her face, and eventually she came to love that too, especially when we could both manage to shoot at the same time. Jenna was always thrilled when she saw two hard cocks bobbing around in her face and then spurting at her at the same time! Ahh...sweet memories...
snarg