My 1st time with anal! Hubby did things right and eased me into it slowly over an entire hour so that when I finally took his cock in my ass I was really able to get right into it and enjoy it. We started off with me using a clit sucking toy to relax while he slowly worked a finger into me. Once comfortable with him fingering my ass we got a tiny plug in and he added a vibrator in my pussy. We gradually worked up in plug sizes step by step and then I was comfortable enough that the nervousness faded into horniness. I sucked his cock and then climbed on and rode him with the plug still in my ass. I reached a point where I was feeling so turned on and so good I just went for it, reached down, pulled out the plug, pulled his cock out of my pussy, lined it up with my ass and just leaned back and drove it in. To my surprise it didn't hurt at all. It actually felt really good, and I just went for it from there and soon he had me bent over pounding my ass until he filled it with cum.
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