I don't know why space pirates are so hot, they just are. I think it's the fact that they swashbuckle, therefore it logically follows that they also know how to unbuckle your swash. Also, the puffy sleeves and the fact that pirates (both male and female) often wear chest-baring outfits. And they take what they want. And they're all about the booty. Anyway, here's a gallery of hentai space pirate images, including the Intron Depot Bullets 4 Space Pirate Blue PVC figure, who caused some controversy with her naughtiness. (Amazon won't even show you an uncensored image of her.) I also got carried away and threw in a couple of non-Hentai images, the cover of Lesbian Pirates From Outer Space and Ralph Maris's Space Pirates comic, just because they rule so much.
There are two main hentai space pirate videos that I came across. The first is the totally awesome Uchuu Kaizoku Sala, or Space PIrate Sara. It's pretty much what it sounds like: Sara is an ass-kicking Space Pirate whose top gets shredded a lot. But she also faces down other pirates, as in this sequence where she uses a special space-based ray beam that shreds her rival's armor and a good deal of her clothing: And here's a clip from Spaceship Agga Ruter, another anime series which features an evil space pirate named Jannis. She captures a duo named Taiyo and Kei, who have a distubingly ambiguous mommy-boy relationship. (They're not actually related, thank goodness.) Jannis has captured Taiyo and Kei for the 1 million credit reward money, but then Taiyo decides to show Jannis what he's learned about using her pressure points to make her feel good (and making her clothes miraculously disappear), in this sequence: I especially like the robots having robot-sex while they watch the humans. Too bad Jannis has her own weird quirk: if she reaches orgasm, she turns into a ferocious killer beastie: