[M4F] [Fantasy] In debt to the Thieves' Guild

Content warning; if you’re not into all of the following, respectfully DNI: torture, necrophilia, scat, watersports, bestiality, STIs, smegma, rimming, prolapsing, menstruation, general filth, musk/scentplay, vomit, ugly bastard, gore, slaveplay, fantasy raceplay, rape, mind break, food play, orientation play, and all other similar depraved delights. The prompt itself is reasonably tame, but those are some of the things I’m hoping to explore in this roleplay. Make no mistake, I’m looking for the most fucked up among the fucked up here.

You were caught. Again.

It was the third time this month already, and you had already been on thin ice; unable to pay your dues to the Thieves’ Guild for the second month in a row. Between dues and bailouts, you were nearing five-thousand gold in debt to the Guild. Not a good look for someone who had only been a member for half a year.

Like the previous times, a man came to retrieve you not long after you were chained up and tossed in jail, having paid your bail on behalf of the Guild--no matter your standing, they never let one of their own rot in a cell. He grabbed you roughly by the arm, and the two of you made your way to the Black Coffer--the Guild-owned tavern, the basement of which served as the center of operations for the Guild, and where the Ledger awaited.

The Ledger, as he was known, was head of the Guild; mastermind behind all that happened in the dark shadows of the city, and arguably the second-most powerful man in it behind the King himself. There he sat at his desk running numbers, organizing heists, and setting bounties, while his harem of whores split their time between rubbing all over him and working the tavern above. You hadn’t any clue how any woman could agree to do that, not for any amount of money in the entire Kingdom would you so much as touch that man. The Ledger was a fat man--no way around that--on the verge of being unable to walk for himself. He must’ve been at least fifty years old, with a bald head and thick neck, and a stomach that must’ve hid his own pecker from sight. The man glistened with a persistent sheen of sweat, though his pungent odor told you that sweat was probably the most pleasant thing that he secreted.

When you descended the stairs, you were greeted by that regrettably familiar fetid stench, and the unmistakable sound of a whore hidden underneath his desk, throating whatever meat he had down there. Two more stood on either side of him, running their hands all over his chest and stomach, occasionally planting soft kisses on his cheeks, or whispering sweet seductive nothings in his ears.

You figured you should be more repulsed than you were.

“Six-thousand, four-hundred, eighty-eight. You owe me six-thousand, four-hundred, eighty-eight gold” the Ledger spoke with a deep grumble, his voice nearly shaking the rafters of the building, like some loud belch. “Do you have any plans to pay off your debt?”

“I’ll steal it” you said, hopeful that maybe you’d be successful this time, and conveniently forgetting the countless times you’d failed already.

The Ledger let out a frustrated grunt. “Bah, you’ve proven yourself worthless as a thief! Do you have any other ideas, or are you as stupid as you look, girl?”

“I… I…” you struggled to find any words, but none came to you.

“Worthless! Worthless little bitch,” he said with a sigh. “As I see it, you have two options. One, I kill you here and now and sell your body parts to the limb grafters, or two…” a devilish grin came to his fat face “you work for me.”

You raised an eyebrow. “Don’t I already work for you, sir?”

The fat man laughed. He turned to one of his whores, and ran a hand through her silken hair. Her face lit up in a wide smile, and you could’ve sworn she had herself a mini-orgasm from that alone, the way her legs shook and she let out a breathy moan. “Not as a thief, sweetheart. As a tavern maiden. The pay is five-hundred gold a week. You’ll have your debt paid off in thirteen weeks. But by that point, I doubt you’ll want to leave.” The Ledger chuckled again, and then his breathing deepened, and his eyes rolled back into his head. You thought he might be having a heart attack at first, but after a minute the third whore emerged from underneath his desk, thick, yellowish seed dribbling down her chin--and you could now see she was heavily pregnant. One of the other ladies embraced her in a deep kiss, swapping his rancid cum back and forth.

If you were telling the truth, you would rather have been executed on the spot. Damn you self-preservation instincts and aptitude for lying. For what it was worth, you at least knew now how a woman could be suckered into being one of the Ledger’s whores. But it was only thirteen weeks. Three months and a whisker. You’d done worse for less, hadn’t you? And there was no way at all you’d ever end up like those weak-minded whores, too. Right?

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If you made it this far, congrats! It should be pretty clear what I’m going for here, but I’m definitely open to changing the exact dynamic to fit your personal preferences. Most details are up for being changed, in fact, so long as the general premise of “in debt to a fantasy crime boss” isn’t lost.

If we gel nicely, I’m more than happy to move to Discord for the roleplay, but I prefer to stay on Reddit while we discuss things.

Hope to hear from you soon, but either way, happy roleplaying!