Molly (offscreen, sounds like Celestia): Hello there, Digibrony!
Digibrony: Wha? Omygosh. Could it be?! Have I been visited by my role model; my inspiration; my fantastic Princess, Celestia?!
Molly (on-screen): Not~ quite~
Digibrony: Oh… oh my…
Molly: My faithful, adorable student Twilight Sparkle showed me one of your videos. It was… very cute. But I was shocked to find that there wasn’t a single video analyzing The Royal Plot!
Digibrony: W-well, um…
Molly: This will not do! Digibrony, I demand that you analyze my blog immediately!
Digibrony: O-of course, your highness! *ahem*
Ask Princess Molestia is one of the longest-running, most active, and most popular pony art tumblrs out there. Drawn by John Joseco–JoSEco? Jose… JJ, and started in late 2011, the comic spans hundreds of pages, and has been very consistently active.
Originally, the comic was based around a kind of one-note joke in which Molestia, an alternate universe variant of Princess Celestia, abuses her monarchal powers to basically rape and molest everyone in her kingdom to her heart’s content. The comic has never taken itself seriously, but early on it definitely did a bit more to play up Molestia as kind of a creeper. Everything was in good fun though, and Molestia’s victims never suffered more than a bit of embarrassment from her harassment; if anything, most of them either enjoyed it, or learned to enjoy it.
This kind of joke has always been a bit contentious, and your mileage will most certainly vary on how acceptable you find the story. The fact that it’s justified in-universe is satisfying enough to me, because I’m willing to sever it from reality. Yes, rape is something Molly just kind of gets away with, but it’s a fantasy story, and that’s kind of the point. But this is getting heavy, and nothing in Molestia really goes for heavy. Except perhaps for Molly’s ass.
Digibrony: It’s a compliment! You know… more cushion for the pushin!
Molly: Mm, I like that… carry on!
Digibrony: Will do.
After a while, the comic started to split its airtime between Molestia and her sister, Gamer Luna. The two of them have a sort of Manzai comedy thing going on, with Luna as the straight-mare. By now, Luna is as much the star of the comic as Molly, ostensibly because she’s probably a bit more interesting to write about. Luna acts as JJ’s stand-in to talk about video games, even if it’s mostly just to geek out over them, and she generally has a more multi-faceted personality than Molly, who’s mostly about perversion.
Which is fine! I’ve made the case for the aesthetic persona already, and Ask Princess Molestia thrives precisely on the aesthetics of Molly’s persona. One of the things I find to be particularly distinctive about the comic’s art, is that it really emphasizes Molly’s larger-than-life nature. Just as Celestia is in the show, Molly is much taller than the average pony, and as such her presence utterly dominates the entire comic. JJ frequnently draws her taking up huge amounts of panel space, shoving her giant ass right into the proverbial camera, which just makes her already dominatrix personality that much more overwhelming.
Molly: They don’t call me “big sexy” for nothing~
Digibrony: You’re the only one who calls you that…
Anyways, Ask Princess Molestia has a number of fun recurring gags and character interactions. Molestia’s intensely intimate relationship with the extremely cute goody-two-shoes Twilight Sparkle is always a blast. It’s an interesting relationship because even though Molestia will molest absolutely everyone she gets her hands on, she seems to be in a genuine relationship with Twilight. JJ plays on this further when he starts to establish an S&M relationship between Twilight and Trixie, which Molly is only as jealous of as she is enjoying it.
There’s also strong shipping between Luna and Derpy, which is adorable, but never really goes anywhere. Derpy is played straight as a lovable ditz, and is always a joy to see. Other ponyville residents make recurring appearances, but have minimal impact.
The last element that needs to be brought up is the fantastic videos that are put together by JJ and voice actress MEMJ0123, also known as Jen. She started doing voice-overs of Molestia comics about a year ago, with the support of Hannah May as Gamer Luna, and a number of other voice actors and actresses. The moment I actually became a fan of Ask Princess Molestia was when I saw the April Fools role reversal video, featuring Gamer Molly and Lusty Luna. Jen brings an incredibly sexy and smooth voice to Molly, and in one spectacularly meta video, her OC Jem trolls Molly on the phone by using her own voice against her.
Molly: So, you think my voice is sexy, do you, Digi~?
Digibrony: I… uh… my role as a meta-fictional doppleganger of my real-world counterpart makes this really awkward to answer…
Molly: Don’t worry Digi~ There’s more sexy where that came from~
(the two are now off-screen, and credits roll over the rest of the dialog)
Digibrony: Whoa… okay, ah! By Molestia’s Beard!
Molly: You mean this beard~?
Digibrony: What does that even… oh my…
Molly: How’s this for thoroughly analyzing?
Digibrony: Fukken subbed.