21 - 40 of 241 Bookmarked Items in Problem Sleuth
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A collection of streams of consciousness from a P.I Headmate of mine! In case you didn't read the tags, none of this is headcannons, it's all "word of god" [hah hah]. Title is from the IDKHOW song of the same name. If you have any questions/want to know more about him, ask away in the comments or hit me up on tumblr! :]
[If Pickle Inspector is god and I'm writing down things that he says/feels, would that make me a prophet?]
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Late Calls by prometheanTactician
Fandoms: Mobsterswitch - Fandom, Homestuck, Problem Sleuth (Webcomic)
14 Oct 2014
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Pernicious Innovator has dropped off the map for a few days, and no one really thinks much of it until Deadeyes phone rings.
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Pernicious Innovator, desperate to maintain Deadeye Detective's attention, makes a mistake that costs the Scoundrels a payout three years in the making.
Or in other words, how Pernicious Innovator faces the consequences of his actions.
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“You’re,” he gulps, “You’re queer, right?” It drops like a brick. His words sting.
“Um.” The investigator looks away. They both knew the answer to that. They’d been dancing around the incident since it happened, Sleuth walking in on Inspector’s secret. Inspector, wishfully thinking, had hoped they’d just never speak of it- of Sleuth seeing him dressed in pretty lace, staring at himself in that thrift-store full-length mirror in his room. The lingerie was supposed to be private, a secret- a soft, sweet secret just for himself. Pickle Inspector doesn’t respond, face flushed.
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Heterosexual Men Wrestling (Gone Wrong) (Gone Sexual) by DaylilyAntares
Fandoms: Problem Sleuth (Webcomic)
14 May 2023
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Two DEFINITELY heterosexual men roughhouse and it somehow turns into gay sex? Notably there is fisting. Ace Dick is inconsiderate and Problem Sleuth is perpetually in love with awful men. Skill issue.
i cannot come up with a better title.
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Bookmark Notes:
Hehehehheeh les gooo
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Bookmark Notes:
Only sex fanfic I’ll bookmark because this is golden, goddamn wonderfully written and a goddamn hilarious ending
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Reasons Why Diamonds Droog Hates Christmas by noxeulalie
Fandoms: Homestuck, MS Paint Adventures
25 Dec 2011
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You can tell when the festive season truly begins when you walk into a department store and see a rack of novelty ties.
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As quick as you are on the uptake, your current realization took you longer than you’d like to admit. To give yourself credit, you’ve been focusing on the professional end of things. You have a city to run, and with that comes pest control. The prime example being Team Sleuth.
Specifically, Problem Sleuth.
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You are one of the top Problem Sleuths in the city and why the fuck do you have wings.
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Your name is Problem Sleuth, and you are just trying to get home. You're bandaged up and beaten, and the last thing you need is some asshole holding you up in a back alley.
So of course, some asshole decides to hold you up.
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Stabdads Shorts and Not So Shorts by prometheanTactician
Fandom: Homestuck, Problem Sleuth (Webcomic)
11 Jul 2014
- Words:
- 7,444
- Works:
- 4
- Bookmarks:
- 12
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Kinkfills: Noncon Edition by homesmut_superfiller
Fandom: Homestuck, MS Paint Adventures, Problem Sleuth (Webcomic)
05 Jun 2014
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Fills I've done for the Homestuck Kink Meme, specifically the Nonconsensual material. May contain underage works as well.
- Words:
- 15,223
- Works:
- 12
- Bookmarks:
- 3
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Scofflaw has a habit of hiding his motivations. It's annoying, sure, but Deadeye is generally good at working them out.
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Slick catches Sleuth snooping around his office and "questions" him. They both know what this is.
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A recently turned vampire Sleuth forgot to eat and during his hunt he finds none other than his rival-with-benefits, Spades Slick. And then they fuck.
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Midnight City - Team Sleuth by ashford2ashford
Fandom: Homestuck, Problem Sleuth (Webcomic)
10 Sep 2025
- Words:
- 49,028
- Works:
- 4
- Bookmarks:
- 3
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Problem Sleuth lives his last days to his fullest by spoiling Slick while knocking out things on his bucket list but not telling slick about dying. At least they had some fun before he kicks the bucket :))))
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Problem Sleuth had been very surprising at first. Spades Slick had expected him to die the first time he sent Hearts out to whack him, but he hadn't. Every single time Slick thought he'd seen it all, the asshole came back with something new to get on his nerves. Or not. It varied by occasion.
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The most dangerous man in the city really should stop underestimating the most intelligent man in the city.
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All Edges of a Koch Snowflake by The_Magical_Crawdad
Fandoms: Homestuck, Problem Sleuth (Webcomic)
08 Jan 2012
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There is more to Pickle Inspector than Diamonds Droog could have expected.
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Part of why you chose the apartment you live in, as opposed to that nice, cheap place closer to your favorite tea shop, was the fact that it had a secret room. In the past you used to use this space to play imagination fort, but lately you’ve adapted it to a new purpose.
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