Well, I don't actually remember how it came about the first time, but probably just curiosity. I do believe her first anal experience was with me. Our anal sex routine pretty much started with her blowing me and "lubing" me up with her saliva, followed by her spreading her ass cheeks and letting me enter. She never warmed up with a dildo until later on, when I bought her that purple dildo, which is shown in this thread. After I bought the dildo, the anal slowed down a bit because she used to stick that up her ass while I fucked her normally. Doggy-style was one of her favorites, but when she was feeling really good, she would ride me for a few minutes while we were fucking anally, which was awesome as well. As far as coaching me goes, she would definitely not be shy about letting me know when it hurt or when I was going too hard, but I didn't listen often, as when she complained of it hurting, I would go harder. She didn't really scream, just moaned, and yes, she was sore after each anal session, as one would assume.
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