The Flip Hole
Already a winner by virtue of its name alone, the Flip Hole also (perhaps not so surprisingly) hails from Japan—where a crack team of masturbatologists toiled long and hard to bring you a self-pleasuring device so advanced, so technologically superior, it makes an actual vagina seem quainter than a Jensen steam engine. Its interior contains such inscrutable features as the "Click Orb," "Side Rib," and "Wing Gate." And the promotional video makes you feel like you're docking in some scary alien spaceship from the future. Which is probably what entering a real vagina seems like to the people who buy this thing.

Honorable Mention: the "Autoblow" Robotic blow job
Didn't Harrison Ford get one of these in Blade Runner—like, 27 years ago?