Streetwalker Quota (Commission)
#19 of Commissions
Ash found himself in a bit of debt. Luckily, he's doing some important city work to finish it off. Unluckily, he's not great at it.
This is a commission for sheparddog762mm. I don't normally write in 1st person so this was a fun test of that style.
The heels were the worst. Plenty of things were degrading about my predicament. The chill of the night breeze rolling through the alleyway, the tight mesh shirt with the tube top underneath to better paint myself as a lady, and then there was the cage locked snug around my cock. Least that last part was hidden underneath the hot pink miniskirt, if only when I stood straight.
But the heels? They made my ankles cry during the long hours on the street corner. Trashy hot pink pumps that clicked and clacked across the cement sidewalks. Skylar told me they'd show my ass more, and my ass is what got the big bucks. So much so that he made sure I had lube in this tiny black fannypack the fox made me buy. I used to have a purse, but those were easy to steal and only added to my debt.
My debt...I shudder at the thought of it. I know how much money I've earned today, and it's not enough to meet my quota by this hour. The last guy's seed is fresh on my tongue, cheap bastard slipped in ones instead of fives. Guess I was too nervous to say no, the rottweiler was big in body, and between his legs.
"Hi Ashley." My back stiffens. Looking over my shoulder, I see a short orange fox hidden underneath a tight blue hoodie and skinny jeans. He smiles underneath the shadow cast over his eyes, "You got my money tonight?"
"Sk-Skylar, I-" The sting of his hand is sudden, but not surprising. "Sorry," I muttered, rubbing my chin, "Daddy. I wasn't expecting you to visit tonight."
"That's why they call it a surprise visit, bitch. Have my money or not?" I nod and unzip the fannypack, shaking as I hand him the rolled-up wad of ones and fives. My heartbeat slows to a crawl as he counts it out, knowing fully that it's not enough for his liking.
"Where's the rest of it?" He asks.
"T-that's it, f-for now, daddy." It takes everything for me to not fall to my knees and beg for mercy. "I swear, guys just aren't fishing tonight. I've been strutting like you said."
"You making sure they're paying in full?"
"Yes." His amber eyes squint through my soul. Skylar knows I'm lying, I've seen that face enough times to tell. He unfurls the hood back, revealing that androgynous prettyboy face that entangled me in his web. Pocketing the wad, he thumbs over to the alleyway. "Daddy, please, the night isn't-"
Another slap strikes my face. "No talking back, slut. Go back there and assume the position." There's no getting around it. My heels tap against the pavement on my way down the alley, turning the corner so no one from the street can see us. Back against the wall, I roll my skirt up, revealing the block g-string constraining my cage, and put my arms behind my head.
"Take them off," Skylar ordered, pointing to my underwear. I comply, slipping them through my legs and placing them to his open palm. The fox pulled out his, or rather, my old wallet from his coat pocket, wrapping the g-string around the brown leather. "Open up and bite down on this."
With a whimper, I do so. My tongue tasted the faint scent of my balls across the cloth. Skylar liked to carry my wallet as a reminder of who owned me, as if the key in on his person wasn't enough. This wasn't the first time he'd 'handed' back my wallet either, and, like a fool, I tried running with it. No sooner did I realize that he'd taken out everything that was important. My driver's license, credit cards, even the piece of paper where I wrote my social security number.
Thankfully I'm too broke to make any of that information useful. Well...I guess that's where the street walking kicks in. "Spread 'em, skirt up," Skylar ordered, kicking my feet aside. Breathing haggardly, I rolled up my skirt and let my caged cock dangle freely before him. There's no other warning. Just a swift kick between my legs that had my teeth dig into the wallet.
"Keep 'em open," He spoke calmly while winding another up. The urge to protect my nuts was strong, but fear of what Skylar would do otherwise won out in the end. He didn't need to be hard. The fox had enough force to turn it into a dull pain, a pulsing hell that made my legs struggle to stand.
"How can you fuck up streetwalking?" He mocked between kicks. "All you have to do is offer those pretty lips and take the money upfront. I did it enough for you, you should remember."
He did more than that. Skylar was the first streetside adventure to really give me what I wanted. Outside he was sweet, lovable, and always showed concern despite what I asked him to do. But when I couldn't pay, that's when the sadist came out. Or maybe it was always there? Hiding behind those devilish eyes.
My legs give in. He stops his kick midway as I collapse against the ground. Drool drips from my maw, falling from my face beside tears of agony. But there was a third fluid escaping my body, one the fox before me noticed all too well had scuffed up his shoes. "Christ, is this pre?" He smiled. Skylar knew what it was, but the tone exaggerated his disgust. I didn't answer, fearful of dropping the wallet.
"You're such a freak," The fox jeered, pressing his precum-stained sneaker against my balls. The pressure had my fingers dig into the dirt, but I said nothing. "I mean, most people would be puking after getting hit down there. But you, you love it." His sneaker ground against my cage, pressing down and shaking the cock within. "You masochistic mutt. Can't even make my money on the streets. What am I gonna do with you?"
The rubber ends of his shoe pressed against my snout, smearing the pre across it. "Tomorrow I want you at the club. If you can't make money on the streets, then I'll put you in the stalls." I kept my head down as he took my wallet back. I know pleading wouldn't help, and maybe a night inside a warm stall would be better.
As Skylar walked away, I couldn't help but stare at the ass that entranced me. I wanted my life back, but the carnal desires in me seemed just find resting underneath those cheeks.