Prescription

Author's Note: Not-so-explicit story but we are getting close sweeties, I promise. Gotta work my way up to it lol. Originally based on a writing prompt, "Mob Boss who looks a lot different than they used to."

CW for peril (held at gunpoint by mommy), dubious consent, impact play, transphobia mention, whorephobia.

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The handle came away with an unsettling clatter but, greatly relieving for Lili, could tumble safely away to the carpet. Every other mansion she'd seen was floored-to-ceiling'd with rich, deepening hardwoods as percussive as they were unethically imported.

Someone at last had the unwise taste to make things a bit softer, and no one would hear Lili's heels clacking away then back to the evening's do.

She pressed the door openly, slipping through the gap into a gently-lit abyss. No one would notice. Lili turned to peer behind the door and felt a warm, metal cylinder press itself against her cheek. At least that's what she thought.

The fireplace twinkled and crackled slowly in the shadow's eyes, Lili looked away burning with terror while her body froze in place. "Gotcha."

"Goodness me, awfully sorry Mam. Just-- getting myself lost is all now." Perhaps the definitely mob-affiliated lady, tucked away in a dead-quiet study, hadn't just heard several minutes of failed lockpicking, followed by some furious few minutes of unscrewing.

"Hmm. I don't think I'm as sure, my eyes have followed you all evening, darling. Has something been making you nervous?"

"No no, Mam. Quite ordinary for my face, always greeting with anxiety. And come to mention it, I'm here with--" Smack.

Before she could dare wonder where the barrel was the shadow had circled round and spanked her, then pressed the pistol harshly into the curve of her back, forcing her forward into the room's centre, away from escape.

"What is it you're looking for?"

"Oh nothing important-- please-- just, the bathroom?"

Lili hadn't hydrated for hours beforehand, spiro would get in her way, so even a few sips of dinner's rosy pairing had left her lightheaded. The shadow's disbelief smouldered in the pause, before it slammed the door shut and sent Lili's nails digging into her palms.

"You'll have your knees on my rug now, darling. Any other move and pop."

She would have stayed frozen without the fire, it wasn't the worst to sink down next to it, and most of her was pretty bare at the moment.

Lili held herself close, and still, but her eyes searched till she spied the iron poker just outwith her reach. It was a bit of hope.

"Now, I'm going to need you to answer at least one of my questions properly, or your evening will be much less pleasant than the rest of my guests."

My rug. My guests. Oh no. "Who do you work for?"

"I was oh--" The shadow uncast itself and she was-- incredible. High-heeled boots fell away to a dark and silken affair that made sure to demonstrate every muscle on her.

Lili shuddered, and not only from base intimidation, as a clutch bag was plucked from her fingers. "--accompanying a gentleman, Mam. I work a shop, but... sometimes find myself needing the help."

The lady pulled a high-cheek higher -- stretching lips, painted like dark chocolate, into a grimace. She was perusing through the bag, tossing out six sizes of condom, a packet of makeup wipes, a small granola bar and--

"Hmm, lying."

--the German-made subcombat was perhaps too much of an upgrade over the typical prostitute's derringer. It was disarmed quickly and placed on the desk, far out of reach.

"Don't tell me it's for self-protection."

Technically that wasn't a question, so Lili kept silent. She looked again at the poker -- that was closer, for now -- but the lady could see her twitching in place. Ca-click.

"Bend over."

Lili's breath roared over the flames, hot and heavy with muffled panic.

"I told you, if you won't tell me when I ask you, then you'll tell me when I hurt you. Now bend the fuck over."

Her head juddered, trying to stay up as she bent herself down. Suddenly, desperately, she pulled back up. "Wait! It's-- there's a rival. But I can't say more--"

A boot hoisted itself over Lili's shoulder and stomped her into the carpet, sending her dress rising over her ass. "Because they'll kill you?"

The sharpened heel dug into her shoulder blade. A smile from above watched as Lili chafed her cheek against the floor, nodding in awkward terror.

The heel pulled free so the lady might kneel down and draw Lili's face up to hers, the other hand finding itself wrapped around the taught hem of her dress. "Darling, if that's all you plan to say then I'm going to be the one killing you. And there's a lot that could happen between when I would, and when they would."

She pulled, exposing terribly insubstantial lingerie and sending the thief sprawling into her own bosom, face blooming red as the thief attempted to withdraw.

"Back down, darling."

Lili pressed her face against the rug, felt the heat licking at her nearly bare arse, not seeing the crop now resting in the lady's hands. "It's, respectfully, more complicated than that, Mam. They're holding something that I rather need-- AHhh."

The pain was quick, sharp, and heavy. The only relief a better, if bitter, understanding for her present position.

"Continue." That was just her testing Lili, enjoying her.

"She's got a hold on all my-- Ahh." Lighter. Lili had slipped and not noticed. "--meds, she has my medication. AHHHh." Harder, the lady's twisted version of a reward.

"What kind?" Crop falling before Lili could speak again.

"EEek. Hormones, they're hormones. I'm--" Lili felt it resting on her, waiting. "Fuck, Mam. I'm a tranny, okay?" She felt the pad drawn up her back, shivering as it slowly pulled away.

"Quite the blasphemous word for yourself, darling. And who is she?"

Lili couldn't answer that, she couldn't. If she wasn't screwed already this would kill her for sure. The rug was stained by a few heated tears, but she hadn't felt it come back down--

Thwack. The lady's sympathies had harsh, impatient limits it seemed.

"YAAAHaha. Fuckin' hells. It's Coloski, Reb Coloski."

Lili tried to peek up but was quickly shoved back down, crop pressing against her temple as the lady mused. "Fucking bitch. And how'd you end up stealing for her?"

"I was--" Lili breathed in, and out. It was too late to deal out half-truths. "I ran out of my meds, and they refused me anymore and I couldn't go back, okay? So, worked the few connections I had, Mam, and I guess it-- worked its way up the chain."

The lady eyed Reb's thief, her thief now. Every family traded in debts but Coloski always loved to play with vulnerability.

"And now you don't get any more -- until a job is done?"

"No, I-- Ahh."

Not that she didn't love it also, but this kind was insulting -- and not for her to play with.

"Straighten up, darling. Pull those legs apart for me." Even if the dress wasn't hiked it wouldn't have helped now.

Her cock -- there's not a gentler way to describe it, sorry Lili -- pressed against the ungenerous mesh at her front, the lady brushing her crop against it, drawing it along her thigh, begging to drive out more answers. Or perhaps just a few more squeals.

"She make you do anything else?"

"I've had to do things for jobs, Mam, but not for her-- Eeeh." It stinged much more here. The lady need only swipe over, not under, and leave Lili with little padding to save her. "But, she promised she'd help me -- Ahh -- promised I'd be out of her debt for this job."

"She set you up."

Lili shivered and blinked, looked at her with dumb shock. A quick smack was enough to squeal her back to her senses. "Eeee-ahh. W-What do you mean?"

"She's done it before." The lady nodded her head to the side. "How much do you know about the Victorinos?"

"Only that is their mansion. Boss went missing some years back but then in comes this woman, sister I think, and takes over in his stead. Not my place to ask why, Mam."

She bent down, graced Lili's lips for a terrifying moment. Her hair was composed into long, black waves, with a rather predominant nose imposing its own beauty on her face.

She looked in Lili's eyes and purred.

"This woman."

"M-m-m-miss Victorino?"

"Yes, darling?" This thief was all hers now. "Did you think I was another lost guest, like you?"

Lili tried, unsure of what she'd even say, to answer. "I-- AHHHhh." It was swift, and hard, and landed much closer to her centre than was bearable.

Vic -- Miss Victoria Victorino -- was talking now, and her thief needed to shush.

"Bitch sent you into Dante's Inferno, where it would be quite undue on my reputation for anyone to walk out."

She started padding the crop against Lili, who tensed at its rhythm and found herself blushing and hardening in response. "There's a mutual agreement I think, if one meant to test me, to let me dispose of one of her more useless tools, from time to time."

"Dispose?" THWACK. "YAAAaaah."

"Kill."

Vic narrowly missed the luridly pitched lace between Lili's legs. On purpose -- the threat brought her enough joy and there wasn't quite such an evocative pain to draw from messy, jumbled parts.

Tears parted from the thief's eyes. "Are you gonna?"

Vic sighed, giving Lili a soft, crooning show of sympathy. Laying the crop behind her and sinking down to Lili's side, holding stiff as Vic's arms wrapped around her.

"You're still a thief, and a liar, and I can't let you go-- but--"

She grabbed Lili by the chin, squishing her cheeks and forcing her to look at a very, very particular cabinet, its contents exposed by crystal glass.

"--do you know what your prescription is?"

---

Lili was still scrambling herself back together as she hurried back to the lobby, pulling her dress the pitiful distance down she could. Miss Victorino was shortly behind her, and even if she tried to run first she'd have to get past--

"There you are, whore. What're you doing?" Her gentleman had his fingers clutched viciously around the whole of Lili's arm, pulling her against a dusty, velvet coat. "Waiting till I'm drunk so you can sneak off without doing what I paid you so damn much for?"

The cheapest bastards always expected the most for it. "N-no sir, but--"

"But nothing. I paid you. You fuckin' belong to me--"

Lili could hear boots where the carpet ended. Feeling a far tighter grip work its way around her other arm, as the man began to stutter. "W-w-woah, hey! Boss Vic! Man!"

"This one's mine now, Harv." Lili saw his eyes widen, for a moment in annoyance, then in fear. He gave way as Vic pulled. "Tell the footman what she owes you, and the right amount. You'll get double that for your trouble."

"Of course, 'course Boss. I won't forget to--"

"Now. And don't fucking harass the staff on the way out." He scrambled, and at least wasn't Lili's problem anymore.

Vic groaned in frustration. "And, he in on it?"

Lili was too close to look up, so just shook her head. This part wasn't a lie. Coloski gave her medication, but Lili still needed the money. And she couldn't be blamed for a double booking when it's what got her in here.

"Shame. He calls me man again and he'll be wishing it was merely treachery. Now, about you-- hmm."

Vic's closeness was having a certain effect on Lili. She belonged to Vic now, her mind familiar with an ecstatic mote of what that meant.

But whether it was better or worse than Reb, it wasn't good -- the humiliating delirium that fear held over her was clearly visible to Vic. And, to everyone else in view.

Vic pulled Lili close to her chest, running fingers through her hair, bestowing a dignity though only so she could make her lose it again later.

"I think I've entertained enough guests for tonight, you however have scarcely begun."