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1. Yumeko & Mary — Daring Constest with Homeless by Archeos_Zabulon

   Fandoms: 賭ケグルイ | Kakegurui (Anime & Manga), Original Work  

   • Explicit
   • No Archive Warnings Apply
   • F/M
   • Work in Progress

   18 May 2026

   Tags

   • No Archive Warnings Apply
   • Jabami Yumeko
   • Saotome Mary
   • Older Man/Younger Woman
   • Homelessness
   • ugly bastard
   • Old Man
   • Public Sex
   • Gangbang
   • Fivesome - F/M/M/M/M
   • Fivesome - F/F/M/M/M
   • Group Sex
   • Dom/sub
   • Double Penetration
   • Dare
   • Gambling
   • Rough Sex
   • Rough Oral Sex
   • Vaginal Sex
   • Anal Sex
   • Degradation
   • Maledom/Femsub
   • Femsub
   • Free Use
   • AI-Generated Images
   • Illustrations
   • NSFW
   • NSFW Art
   • Hentai
   • Doujinshi
   • Digital Art
   • Submissive Character
   • Rough Kissing
   • Contests
   • Aged-Up Character(s)
   • Deepthroating
   • Smut
   • Shameless Smut
   • Dirty Talk
   • Age Difference
   • Rivalry
   • Friendship
   • Public Blow Jobs
   • Public Humiliation
   • Collars
   • Leashes
   • Rimming
   • Outdoor Sex
   • Groping
   • Vaginal Fingering
   • Plot What Plot/Porn Without Plot
   • Porn
   • Exhibitionism
   • Humiliation
   • Public Nudity
   • Consensual Sex
   • Orgy
   • Face-Fucking
   • Multiple Orgasms
   • Multiple Partners
   • Large Cock
   • Come Swallowing
   • Power Dynamics
   • Cheating
   • Kissing
   • Lemon
   • Consensual Degradation
   • Alternate Universe - Canon Divergence
   • Barely Legal
   • Public Masturbation
   • In Public
   • Semi-Public Sex
   • Degradation Kink
   • Humiliation Kink

   Summary

   After graduating from Hyakkaou Academy, Yumeko Jabami and Mary Saotome hit every single one of Tokyo's illegal casinos and end up getting banned from all of them because of their usual over the top shenanigans. But it'll take more than that to stop the two gambling addicts, who decide to face off in a daring contest with increasingly depraved stakes.

   One night, they go to a homeless camp full of dirty hobos and push each other to their limit trying to find the one dare the other will refuse to do. But with their stubbornness, the dares just keep on getting smuttier, with no end in sight.

   Not that any of the homeless men complains about having two sexy college girls willing to disgrace themselves in their secluded camp...

   Series

   • Part 7 of Naughty Girls Having Fun

   Language:

   English

   Words:

   9,808

   Chapters:

   3/7

   Comments:

   27

   Kudos:

   193

   Bookmarks:

   51

   Hits:

   56,607