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Anonymous
1: Heck yes.
2: Depends on how much control she has over the tail. 2a: if the tail is under her direct control, approach with a chastity belt on. let her try to jam it in, then catch it and tie it down to something. 2b: if she doesn't have any control and the dicktail just fucks whatever comes in range, I first go out and kidnap another girl, tie her up, and toss her into range. Let the dicktail do its thing, and while that's happening, I slip in and stick it in.
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