Okay! I spent the last few hours reading all the entries and figured I'd at least try to provide something for each entry. Hope it's actually helpful.
Division: You had some inklings of very good prose here, but you got too caught up overexplainig every detail. It's a bit of a balancing act, but if you ever find yourself in doubt, tend towards less, not more.
Outside Context: I, uh. I dunno. It feels more like someone describing an improbable tabletop RPG occurrence than any actual story. Why did the stray human run constantly for weeks? Why is Gensokyo collapsing inside of a few weeks? The plot itself is... well, I get that this was kind of a shaggy dog runaround story, but you came at it from the wrong angle. Most of the story was told in... well, the story, not actually having characters doing things, and what was there was mostly just memetic reference. You have all the pieces of what could be a pretty amusing parody here, but they're not really put together into a coherent whole.
Impetus: First off, your sentence structure needs some work. It comes across as snippets of fragmented info, and occasionally misses commas to help the sentences flow. That can work in a given style, but for regular descriptive writing, you want to spend a little more time on your grammar. Same goes for spelling, punctuation, and overall polish. It's not just about writing what happens, but communicating your ideas, and that needs clarity. Give your stuff time to cook, so to speak.
Machinations: My biggest problem here was the dialogue and stream of consciousness. It was a bit overwrought and stilted.
Untitled/Youmubutt: Like I said above, work a little on proofing, but your opening prose is pretty good. Things like itself versus it's self, and so on. Try not to get caught up on little details when trying to paint a big picture. Also, scene transitions should be made a little clearer--a few extra lines or a break. Also: References! I love a good nod now and then, but try not to make them too obvious.
A Truth to be Told: This one was probably the best-written in category as of writing this. The ending, or lack thereof, is a bit contested, and I find myself agreeing that it needed just a little bit more. As for constructive suggestions, try to add a little bit more description to the environment. I fall into the same sort of writing, letting dialogue drive it, and it's something that needs to be consciously worked on.
Answers: Your sentences are all sort of clipped and awkward--they don't really flow well as Ally's thoughts. Interesting opening premise, though.
Rooibos: This one was probably the most technically proficient thus far, but a bit brief. The interplay was good--it caught the right tone of banter. More time and practice will do you good.
In Case of Trouble: This is interesting, but I think you suffer a bit from overly florid prose. It does capture the feel you were going for, but remember above all else, it's here to be read. If it's cumbersome to read all the way through, even if by design, then that's detrimental to the telling of the story. The ending was adorable. Good show. (And on a final note, if the title was a Bastion reference, +10 anon points.)
DOLL: Enh. Yandere never did it for me. It was written well enough, but the substance was all "oh no creepy doll."
Where the Fox was Tamed: This had an interesting kind of mythological/fable feel to it, and I enjoyed it. But as a vet category writer, it had a few stilted aspects that needed work--the expressions of Yukari's annoyance in particular rubbed me the wrong way. But Ran's naive innocence and cleverness came through nicely, and her whimsical nonlogic was very endearing. Overall very good.
Initiation: This had all the terror and dread of the first hunt, and the violence was good and visceral. The last line felt very off, however--and while succinct, it didn't really feel right. Good combat, just work on your window dressing.
Dogfight: This one needed a bit of a better ending as well. The fighting was good, Momiji's struggle to puzzle out Sakuya's trick was interesting, as was the "reveal," and then Sakuya dropping the hammer on her. A little melancholy for Momiji, but on the whole pretty good. Also, the idea that Sakuya has a shack full of knives is hilarious.
Building Bridges: This one felt overly-descriptive as well--and honestly, one vibe I got from it was "this was written on little to no sleep." I dunno if that's accurate or not, but it could definitely have benefited from a thorough proofing, if it lacked one. That said, you have good ideas--fun background for Parsee. Just work on your delivery.
Bond Fire: This one was nice, but I felt it was a bit too long and roundabout. I know, half my advice is "too long" and the other half is "too short," I'm helpful. I mostly felt like the prose was just a little bit too much each go-round; a little bit trimmed from just about every instance would make this a much shorter piece without costing it anything.
Nicotine Rhapsody: This one was mine.
Digger: I liked this one, probably my favorite thus far. It caught the cynicism inherent to a life hard lived without drowning in it; it captured the violence and gore and muck without wallowing or obsessing over it. It was conversational and to the point, and it worked. And the ending was stellar.
Missed Connection: SPAGHETTI MERMAID. Amusing. I could practically see her talking to herself in the "mirror" as she psychs herself up. A nice departure from the "classic" storytelling formats we've been getting, and pretty solid.
Hisou Tensoku; or, The Catfish: Okay, this was pretty funny. Poor, put-upon Iku and a spoiled celestial is usually a recipe for good fun. I guess if you want critique the plot is, you know, but SOMEHOW I DON'T THINK THIS FACT ESCAPED YOU, so thatsthejoke.jpg. Good solid entry, had a good time reading it.
Unfortunate Scent: Melancholy, but not overly so. Once the dog reveal was made, the brief, simplistic thoughts fit into place nicely.
The Unluckster Musicians and the Curious Vampire: >Kill the time pun
11/10 contest over everyone go home. But seriously, this one is pretty funny too, though honestly I could have lived without the memes and the slight bits of meta. A few small errors here and there, but otherwise pretty all right. Not the worst story about braining a vampire I've ever read.
Cat: Interesting premise, and the contrast between the precision of the numbers and the abstraction of Alice's wooden thoughts. A strange candidate for being that far out of touch, but it worked well enough. [spoilers]If I see that fucking cat one more time...[/spoilers]
Difference: Yeah, this just needed a little more... anything, really.
Farewell, Our Better Halves: Sad and bitter and full of regrets well-spun. It manages to capture the way things turn out wrong even despite our best efforts. Yuyuko getting what she wished for in the worst way helped encapsulate that. I almost want a continuation, seeing how the unlikely new Konpaku and Yuyuko get on in the following years. (Almost.)
Heart to Heart: Nice. Short, sweet, and doesn't overstay its welcome. Also a nice chaser to the grief in the last entry, though each was good for opposite reasons.
Densha de R: Reimu sure didn't seem to give many damns about any step of this train ride. The entire penetration was what, one line? And while I could tell you were angling for the ending by that, muted sex doesn't really make for arousing sex. It was more "this is a thing that happened" than actual erotica.
Heated Passions: This one kind of suffered from the same problems as the first, just not in a train. There was very little heat and not all that much passion. It was more cute than anything, which I guess isn't a bad thing.
The End of Sunflower Racing: This actually did a pretty good job balancing the sex with the shift in tone from dominance to equal footing. A few minor details here and there, but nothing really worth marking out. Other people might complain about the male Wriggle thing, but it suited me just fine, I'm not really a futa fan.
Ready, Willing, and Able: Ow. Also, there really wasn't all that much sex in this, but eh. It is what it is.
Dr. Kirisame or: How I Learned to Stop Worrying and Love the Bomb: Marisa
Hilarious and terrible. GJ, and I do so love a good, bad title.
[x] Consensually Love The Maid: It was all right, and fairy ass is always a welcome sight, but... "your tongue transforming into a tool of female pleasure?" Really? It was all right, but a few lines were a bit silly. Still, cute ending, fun sex.
Black Lotus: >milk the magic out of Byakuren
... Well! The break-y rape-y things aren't my favorite, but it was well written.
A Compromise: This one was a bit like the fairy maid one--some of the wording and slang just got silly. The antics themselves were cute and funny, though. Bretty gud. ...though the later dirty talk didn't do anything for me. It's kind of hit and miss by nature, and I didn't have the luxury of getting super into it, so take that with a grain of girlcum.
Now then, my actual votes:
ROOKIE: [x] In Case of Trouble. Honestly, this one had its flaws, but the story and the telling were entertaining, and it came to an excellent finish. All of them had some problem or other from a technical standpoint, but in terms of story content alone, this was my favorite in the category.
VETERAN: [x] Digger. There were strong cases to be made for most of the entrants, but Digger's tone hit me just right. It also wasn't overly long--something that's valuable in writing--and had a strong punch for its ending.
ADULT: [x] The End of Sunflower Racing. This one struck a good balance in the gory details and not going overboard, and it managed to capture the "working relationship" of Wriggle and Yuuka well. I liked it both as porn (most of them did the job there) and as a story, so it was my overall favorite.