Uptown

The idea of getting humiliated and used by horny middle aged perverts terrifies you. Worse, you are scared of how tempting it sounds. Besides, you don't want to be out all night. Who knows what Daddy has planned for the morning?

"I'll head uptown, thanks." Principal Latimer lets out a frustrated grunt but doesn't push it further. You are grateful for the ride, so you don't argue when he pushes your head down to give him some road head. You also want to find out if his cum tastes as different from your Daddy's as his does from Mommy's.

You find out just as he pulls the car over. He has his own unique tang, and you hope no one notices it dribbling down your chin as he says, "Keep the change, slut." And pushes you out the car door. You survey your surroundings. You are literally sitting in the gutter right outside a Ritz-Carlton , your limp clit exposed, wearing what can only be described as a hastily assembled crack whore outfit, and you are hurriedly lapping up a dangling strand of semen off your chin. Oh yeah, you blend.

You decide you better find a customer fast, before someone calls the cops on you. As if in answer to your prayers, a Audi pulls up next to you, rolls down the backseat window and a devastatingly handsome young man asks, "Are you alright, Miss?" Before you know it you are pulled into his private parking garage and are stumbling for his belt in the backseat while his chauffeur stares silently into space.

"$300 just for a blowjob? Don't tell me you get even half that for your ass downtown." The small talk and pleasantries were nice, but once it gets time to talk terms he's all business. He feels fit under his suit, much harder than you'd expect a trust fund kid to be. You are tempted to cut him a deal just so you can run your hands all over his chiseled body. And besides maybe he will be your knight in shining armor.

"You can fuck me for no extra charge. And I can pretend to be your little sister if you are into that kind of stuff." He smiles but in a way that makes him seem angry. He pulls you into a kiss devoid of affection or romance, like he's exploring your mouth for weaknesses...he find's plenty. You melt at his touch, crushing your body against his and losing yourself in his loveless, but no less hungry embrace. You feel handcuffs bite into your arm and giggle as he pulls your arms up to clasp them together. "Mmm do I have a kinky big brother?"

"No, you have an undercover cop, arresting the trashy sissy whores that have been plaguing uptown and pissing off the muckety mucks." He pulls away from the kiss and you feel a pit in your stomach. Your mind races in circles. Oh God, what is Daddy going to do when he finds out I got arrested? What is going to happen to me in jail? Will they put me in with the dangerous inmates? Will they let me change clothes? Shouldn't this cop at least have let me suck his cock before cuffing me? Or after, just why arrest me for being a hooker if you don't let me hook first? And so on...

You arrive at the station and the "chauffer" opens your door for you, roughly yanking you out of the car. He is a big brutal man with a crater pocked face of acne scars. You know the type, picked on in school, finally got big and now they want to be a bully. Like you this morning, you realize with a shudder. He painfully plants your face over the trunk, your ass **** and exposed. You shudder as you feel his rough hand slide up your leg slowly, about to reach your ass...

POP

"Quit resisting, whore. I've got to search you fer contraband." You can hear the whole contraband playing after that blow to the side of your head. Feeling spacy as stars flicker in front of your eyes, you notice your Prince Charming is nowhere to be seen. You are alone with the ogre instead. You remain perfectly still, as he holds your handcuffed wrists painfully tight in one hand and gropes you ass with greasy fingers with the other. You swallow a low moan, afraid to even breathe...

POP

"I said quit resisting! If you're a good sissy, maybe I'll let you change before putting you in lock up with the rest of the animals." You try to indicate by your silent stillness that you comply, but you get the feeling Officer Ogre is looking for an excuse to brutalize you no matter what you do. You are thankful for the swimminess of your thoughts at least, you are only vaguely aware of how terrified you should be, and those thoughts are soon replaced by the clumsy, but oh so insistent probing of the pig's pudgy fingers...

"Hmm...see you're smuggling an unidentified creamy substance. Probably some new street ****." You can't tell if Sgt. Shrek is playing dumb to justify his search or if he really is that fucking stupid. When he rubs a glob on his teeth, and grunts "Nngh...pure!," you decide the latter. Either way, he now has all the justification he needs, which is none, to push his pudgy little pecker inside your gaping hole.

"So...fucken...tight!" You wonder which hole he's fucking because despite your best efforts to milk his microdick, you can barely feel him rutting around inside you. You never thought you'd miss his fumbling fingers, but at least you felt them. You think you might actually have a bigger clit than him, and definitely more finesse. "Oh shit, get ready for the monster load of your young life!"

POP

Well...at least you felt something. You are still spacey as you feel his pathetic pump sauce dribble out of you. You are getting so horny you start wishing he would just throw you in lock up. At least those "animals" probably know their way around a sissy pussy. You start shaking off the fogginess with a sweltering shiver. You can't let him put you in lock up like this. They would have to identify you from the fragment left between the inmates teeth...

"Please, Mister Officer Sir, I can be an awfully good girl if you let me make a phone call to my Daddy and change clothes." You look up at him with a mix of plaintive innocence and debauched desire. He licks his greasy lips and pushes you to your knees. You keep eye contact, making sure not to pretend to react with lustful hunger instead of disappointed disgust when he rubs his vienna sausage on your lips.

"That's right...bigger than you're used to I'll bet. Finally got you a feast when you found you a man who don't have to pay for it!" You "shallow throat" his full length and **** your eyes not to roll at his boasting. You bob on his cock, faking "glugging" gagging noises so he thinks you're struggling to take his full two and half inch length. It tastes foul and unwashed, but you slather it with slobber anyway. You try to think sexy thoughts, imagining your Daddy, your Principal, and Prince Charming all taking turns in your throat. "That's right...you're fucken in love with my cawk! Here it comes...don't...you...spill...none!"

POP

You are starting to look forward to his brutish blows. They at least let you know he's done and his shameful spurt wasn't just a dribble of precum. It tastes spoiled, but that could just be the lingering taste of his cock. Besides, you've earned a chance to get out of here and change clothes. Maybe the other inmates won't smell the sissy on you. All you need is just a little more luck...

"Alright, whore. You can make your phone call and change clothes after my shift ends...in about six hours. Until then, enjoy lock up."