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(Pt.1 of this series can be seen here.

To repeat (or to copy/paste, more specifically):  

For the most part, I only have photocopies of my older con sketches, but for these 1999-era pieces, a commissioner from Back In The Fabled Day sent along scans of the original pencils. To be honest, photocopies might be better, as these pencils are surprisingly light and low-contrast; I had to level-adjust them in Photoshop to a far more pronounced degree than I normally use with contemporary graphite-based images.  (Note: In fact, the second image above is scanned from a photocopy.) 

Anyhoo, as you can see, "damsel-in-distress" pics have constituted a fairly constant portion of my commissions at conventions for over twenty years, most of which featured Kei and Yuri from Dirty Pair in distressing situations. Most of these images are rather far from being "in-continuity" for my version of the DP, as the comics' heavily augmented and cyberpunked-up Kei and Yuri would presumably be a lot less easily damseled by low-tech means. (Hilariously enough, a Patron spotted an actual, in-continuity rationale for this content, which I'll have to scan out of the relevant Dirty Pair volume and post here sometime.) 

And now, a few words about each. Gotta say, Pirate Queen Shasti is pretty neat, regardless of her lack of depth perception:

I'm almost certain I've seen a color version of the illo above, but couldn't dig it up in time for today's post.

I returned to this goofy scenario a year or two later, as this next piece features Kei with the ponytail dating to the never-published Oopera Gloves, Hot Pants & Garter Belt costume variation I drew for a number of con sketches out of sheer boredom. Note that Kei and Yuri's "wench-y outfits" will return in a future DiD commissioned story (or "story", in quotes.)

More Sim Hell-related shenanigans in the next piece, as those glasses seem to indicate that's Santa Sleet. The commissioner had asked for ribbon-related distress, hence the "Xmas present" bit. To be honest, the skeeviness is strong with this one:

The skeeviness is even stronger with the next one, as its Sim Hell-harem flogging scene strikes me now as way too harsh and unpleasant; the scourged Yuri in tears, especially, creeps me out. Years before Empowered, I was apparently already engaged in undermining DiD scenarios with unasked-for emotional content. Ehh, maybe there's a playful and lightly comedic way to depict a flogging (as the commissioner had requested), but I certainly didn't know how to achieve that at the time. 

And look, its the Opera Gloves, Hot Pants & Garter Belts costumes I mentioned! (These, too, will be featured in upcoming DiD "stories".) 

Anyway, still more 1999-2000 con sketches are yet to be scanned, but most of 'em will be from photocopies. Next DiD Wednesday, I'll likely go for some more recent sketch sets. Or should I scan some old images and write up a post addressing my unheralded creation of deviantART's favorite bondage trope, the tape drone? (Not that I wanted credit for it, mind you, as I was still clinging to the hopes of a mainstream comics career at the time.)

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andrew

Your tape drone was extremely prescient. https://www.youtube.com/watch?v=CCDIuZUfETc

KranberriJam

Love the pirate themed ones, perfectly torn clothes and everything~

Burninator

You know, with the little fangs and that particular smile, "Captain Shasti" in the first drawing looks an awful lot like Ocelotina. Conveniently, the pirate hat would block cat ears, Kei being in the way would conceal a tail, and the bra is properly shaped to cover up little decorative cat eyes. And, I've never seen Shasti and Ocelotina in the same room together. VERY intriguing. (Seriously though, cool stuff.)

SuichiTanaka

As someone who was involved in the spread of the tape drone, I'd VERY much like to hear your thoughts on the thing. Positive or negative, I think it'd be an interesting bit of insight.