For the past few years, I ran a variation of "The Dread Pirate Roberts" in a small Star Trek text-based sim. I've decided to port it over, and develop it further into a full on fanfiction; with "names changed to protect the innocent." The story will be primarily set in the TNG and later Prime Universe, with a distinct preference for JJ Abrams stardate convention (23xx.yyy), and will involve the Destruction of Romulus later in the story (a plot point from the sim).
"Wes", a pseudonym taken on by the protagonist, the son and step-son of Starfleet Admirals; is captured by the Dread Pirate Roberts, much like Westley in the book and movie. And following along with the plot of The Princess Bride, Wes eventually becomes "The Dread Pirate Roberts." At some point within the plot, he'll be captured by Starfleet, escape custody and steal a SOCOM (Special Operations Command) light freighter, becoming a smuggler, and eventually becoming a legitimate civilian in the employ of Starfleet SOCOM.
Buttercup's role is fulfilled by Meralle, a former Orion slave girl- and one note here, I prefer to ignore the melding of Orions and Deltans in ST:Enterprise and go with more TOS/TAS perspective in that Orion women can, indeed, be enslaved and sold. And while I've got some ideas already for "Buttercup 2.0" (see below), I'm leaning towards an antagonistic initial meeting developing into a *real* relationship, unlike most of my other fanfiction works.
Antagonists will be the usual- Starfleet, Orion pirates and slavers (The Black Kris slaving clan in particular), the Ferengi, etc.
Star Trek, being the relatively rich universe it is, allows for numerous ancillary characters; and as for The Princess Bride? It's in space, and will have various new elements to it. Slavers, pirates, starship battles, etc.
Dramatis personæ:
Jack “Wes Roberts” Landry, ex-Starfleet officer turned pirate after being captured
Meralle Roberts- Wes’ Orion wife, ex Black Kris slave; released by Wes
Sairi Roberts- Daughter of Meralle and Wes
L'illa Roberts- Adopted daughter of Meralle and Wes, post-Romulan Holocaust
Javait- Romulan First Officer
Frank Roberts (no relation) 2d Officer
Tarelton Clemens- tactical officer
Cheraath- Vulcan doctor
Malaerys Taelennis- Betazed Helm
Pádraig Ó Finn- Engineer
JB- Tellerite Security Chief