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This was the first time I successfully inserted a medium butt plug in my then still tight asshole. My anal ring hurt and stung before I could slide the butt plug past the wide base. I was naked, and my wife helped me sit on a chair with the butt plug pointing up. It was awesome as I lowered myself slowly down and I slid down the plug. My butthole stung for a second and it was finally inside of me!
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