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I wanted to prepare my asshole for my boyfriend. I planned to surprise him with anal sex but I wasn't sure if I might be too tight for him. I asked my room mate for some advice and he was ignoring me for his video games until I lifted my dress to show him my butt plug. He got a boner and started jacking off to me! I thought that maybe he could help me out and see if my ass could be stretched and prepared a bit better!