I could see that she was tensing up a bit.“Just relax and this will go in much easier.”She relaxed her sphincter and I was able to gently push the...round plug further in her anus. I could see her hands down at her sides grasp on to the sheets. After the plug was just past its full width, about an inch and a half, I let go of it. I quickly slid right in her ass with a small ‘pop’.“Now, you are going to leave that right there until I give you permission to remove it. Now, stand up and face. It was late enough that the pool was almost deserted; the only people in it a small group of people roughly our age. Half of them seemed to be leaving as we arrived, so when we finally stripped down to our underwear and jumped in, there were only two guys in there with us.Anna had been drinking and is a pretty flirtatious person, so before long she’d struck up a conversation with the guys, and the four of us moved together to chat. As we talked, they brought up the topic of “the topless chick. More

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