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While rare, it could be achieved if the inserted penis is small enough and the receiving penis is large enough, most likely with the urethra being stretched carefully until it is able to accomodate (unless tearing is welcome or not a concern). A similar and much more common practice is called docking, which is mutual masturbation by inserting the glans penis into the foreskin of another penis. Needless to say this can only be performed when at least one of the penisses have a foreskin.

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