Victoria's Secret: Hotel Hooker!

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A roleplay goes sideways as she ends up hooking for real.
5.7k words
4.38
150.2k
146

Part 2 of the 7 part series

Updated 08/30/2017
Created 06/08/2015
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"You look a little lost, love?" the prostitute laughed, looking in my car window.

I did. My Rolls was fine; there were a lot of expensive cars in the red light district. However men, not beautiful women, drove those cars.

"I'll pay you for your time. £200 pounds for the next 30 minutes" I said.

It was an absurdly high price, especially in this neighborhood, but I didn't want to haggle. She was just the right mix of sexy & seedy and I'm a woman able to buy what I want. The hooker immediately got into the car.

She directed me into the parking lot of the hotel she worked at but we didn't get out. I wanted to talk, I explained. Just talk.

The prostitute said her name was Julie. I said mine was Victoria, before realizing it was a mistake to use my real name. Oh, well. I offered her my hand, and she laughed, saying, "That's normally not what my customers want me to hold."

Funny, but I was too nervous to laugh.

I explained to her that my boyfriend Randolph liked to visit prostitutes. He had actually suggested that I dress like a prostitute to help him live out his fantasy, but I had laughed at him. I was the daughter of an Earl, and a trust fund baby! Me, a prostitute? The idea was absurd!

Since he wasn't getting what he wanted from me Randolph began going out on his own, risking disease, his reputation at the firm, and our social standing. That simply would not do.

"I want to... please him," I explained. Make his fantasy come true. I want to be his whore."

"There are Halloween costumes on the Internet, love," Julie chuckled. "Of course they don't teach the things I know at Oxford."

"Yes, quite right. That's why I'm here. This is a world that frightens me. A world I don't understand."

"Does it excite you, love?" Julie asked. "Does the thought of being a hooker for your boyfriend turn you on?"

My blush answered her question.

"Why don't you just hook old Randolph up with one of those posh escort services? That way he can get what he wants and you won't risk—"

"Randolph doesn't want a high class prostitute. He said he wanted me to be garbage, right out of the gutter... a suck-him-off-in-the-alley-for £15 hooker." "I want to be...authentic," I explained, looking down at my trembling hands. "I want you to teach me how to act trashy, like a real whore."

I was so lost in what I was saying that I had forgotten I was talking to a person. When I finally looked up I saw that Julie's face had hardened. "So that's why you picked me? Because I look like trash? Because I'm garbage beneath your feet, Miss Posh?"

"No, I didn't mean that!" I said, realizing too late how insulting I had been. "I picked you because you looked... smart. Smart and... experienced."

"Experienced?" Julie laughed. "Yes, that's one word for it. Sucking dongs all day will get you experienced real fast. Okay, love, times up. You want to find out what it's like to be a prostitute, come down here tomorrow and we'll spend the afternoon together. I might even let you watch me do a trick, through one of the peepholes."

I both shuddered and felt a wonderful rush of excitement at the thought. This was more than I had hoped for.

"Don't bring your car, though -- it will get boosted in 5 minutes if you leave it outside. Take the bus. And don't bring that candy ass "STEAL ME" handbag, either. Put your ID and money in your shoe."

"Is that safe?" I asked. "The bus, I mean?"

Julie laughed. "You want safe, stay on your estate, Queen Victoria. 2PM tomorrow, here in the parking lot."

"I see. Is there a bus that—"

I was too late. Julie was already strutting down the street, trolling for her next trick.

The next 24 hours were a blur. Picking out plain clothes that wouldn't get me killed in the red light district was the first challenge, mastering a mass transit system was another. My maid explained how the buses worked, but seemed confused as to why I didn't use my driver. Why indeed: I'm sure my chauffeur and the other vulgarians who worked for me knew the place I was going, another indignity that made me shudder and want to pleasure myself all at once!

Aisha, who works in the kitchen, was able to lend me some jeans and a modest white shirt that didn't look either too sexy or too expensive. It's hard to look plain when you're not. I put on sneakers and put my credit card, cash, and ID in my shoe. Not daring to take my smart phone, I sent my chauffeur out to fetch me a disposable, which I buried deep in my pants pocket.

I brought a thick wad of cash, but standing on it made me feel a bit safer as I changed busses twice to get near the red light district. From the stop it was a 10 block hike.

It was Friday, but only 1:30 in the afternoon, so there wasn't much traffic. I had gotten there early, partially because I didn't trust the bus schedules and partially because I was too excited to wait. Unfortunately that left me with some time to kill in the parking lot.

A car pulled up beside me. A fat middle age bloke with a missing tooth leaned out of the car. "How much, sweetie?"

"How much for what?" I said, genuinely confused.

"You," he said back flatly.

I was horrified. I had dressed plainly, but he thought I was a prostitute selling my wares! Panicked, I turned and ran away, stopping when I encountered a doughnut shop to hide in. Taking some money out of my shoe I dropped it on the counter, buying me the time I needed to hide from the world for an hour as I stared at the coffee I didn't touch.

I was on time, but Julie was not there. At long last Julie, coming out of one of the rooms with a customer, beckoned me into a different hotel room that faced the parking lot.

The "tour" was interesting: a bed, an enormous "party pack" of condoms, a standup shower and an old toilet with the bowl stained a horrible brown. The room stank and I wondered when the place had last been vacuumed or the sheets washed, but dared not ask. In some ways the very foulness of the place pleased me; for I knew even Randolph couldn't fantasize about anyplace worse than this!

Julie dumped a brown paper bag with some clothes on the bed. "Strip of your clothes, love. We'll get you all prettied up."

"I beg your pardon?" I said. "I'm quite certain I don't understand."

"You wanted to know what a prostitute would dress like. You're a bit taller than me, but I got one of the girls to lend me something. Something borrowed, something blue!" she chuckled.

I watched, mouth agape, as the clothes were laid out onto the bed. There was so little there, and those horrible red boots!

"Come on, girl, STRIP OFF," Julie demanded. "You're the one who wants to look like a whore, remember?"

Julie laughed when she saw the huge wad of money, platinum credit card, and ID in my shoe. "You could buy this hotel with that!" she said, placing the money and cars with the disposable phone on the bed.

I covered my breasts when I took off my bra. I knew Julie was comfortable with nudity, but there was something unnerving about having a fully dressed prostitute evaluating me and looking me up-and-down and grinning at me like the Cheshire cat as I stripped. It was almost like I was the prostitute! And the feeling of my bare feet on the putrid "rug" was truly disgusting!

I hesitated when I got down to my knickers. Julie smiled. "The moment of truth," Julie snickered. "Come on, your highness. We need to see that tight little money-maker of yours. Hand 'em over."

Reluctantly I surrendered my knickers to Julie's grasp. "Not bad. Turn around. I want to see your ass."

I blushed as Julie let out a slow whistle at the sight of my bottom. "Nice. Sir Randolph is a lucky man. My ass hasn't been that tight in 10 years. But that pussy is way too fluffy."

"I keep it trim," I explained.

"You'll keep it bald," Julie corrected. "Faster cleanup. In this business, it's all about the volume. Remember it's not your pussy any more. It's your inventory."

My vagina was inventory? The idea sent a chill down my spine, but it was tremendously exciting, too. Lost in the degradation of it, I let Julie take me in the bathroom and shave my vagina bald with a can of Barbasol and a cheap disposable razor. The cream burned, but Julie was gentle if a bit workman like. She caressed me towards the end and to my embarrassment I actually rocked through an orgasm even as she left me bald as a billiard ball.

The outfit that Julie selected for me was basic cowgirl: a white tube top with no bra, an obscenely short & tight denim skirt, and thigh high red hooker boots that were too big. I tried not to think about who wore the lacy red knickers before me, but they certainly didn't smell very good. Even with the short skirt I wanted to skip the dirty red knickers all together, because of their rancid smell, but Julie insisted feeling "well used" down there was a key part of the experience.

Makeup was next: purple eye shadow with a bit of glitter, false eyelashes, too much red rouge on my cheeks, bright red lipstick, eyeliner everywhere "so they can spot you in the headlights." The makeup got caked on thick and fast and by the time she was done I felt more like a clown than a lady.

A blonde wig over my stylish and carefully coiffed black hair completed the transformation. I spent the next several minutes staring in disbelief at the girl in the mirror, the cheap prostitute who looked nothing like me: my bare white thighs, my bouncing breasts with my nipples clearly visible through the fabric, my tight butt cheeks and underpants peeking out from under my skirt at the slightest movement, my whorish makeup.

"You're a hot little number, Vicky," Julie laughed. "The punters are going to love you."

Vicky? I gave the cheap little tart with the pointy nipples and red boots a hard look. Julie was right. Victoria had vanished, and I was now Vicky. The girl in the mirror had no money, no class, no education, no resources at all. The only thing she had to offer anyone was sex.

I felt a chill as I looked at my image. The girl in the mirror begged for contempt, and was the sort of cheap, trashy, garbage men spilled their seed on as much in disgust and contempt as lust. I was glad Julie had done this to me for I NEVER could have made myself look this way! I felt completely degraded but also incredibly excited. To make matters worse my excitement caused my pussy juices to slosh and mix with the dried stench of the whore who had worn the lacy red knickers before me, creating a noxious brew

Without even thinking, I reached between my legs, and wetted my fingers. Instinctively I turned my face away as I brought my fingers up to my nose. My stench was appalling!

"Nice and trenchy," Julie laughed, grabbing my lacy crotch for a good-luck rub. ""I can smell the juices dribbling down your thighs. You're a real slut, Vicky."

I smelled like a rotting fish but Julie was still not satisfied, dousing me liberally with a noxious "perfume" in an unmarked bottle. The scent was a mix of burnt trash, undiluted Pine-Sol, and stale urine, but the more I tried to shield myself from it the more the laughing Julie sloshed on me.

"It will make you stink like a whore," she promised, as if the noxious stench already wafting up from my 'trenchy' pussy hadn't done that already.

I was struggling not to puke when the door opened and an unshaven man in a leather jacket strode into the room. He was squat, in his early thirties, and muscular, with an ugly scar on his right cheek.

"Here she is, Jake," Julie said. "The posh bird I was telling you about. All setup in her room."

"But this is your room," I said, confused.

"Naw, this is your room. The sink and shower don't even work in this shit hole," Vicky laughed. "Here's what she brought you, Daddy," she said, nuzzling up to the thuggish intruder.

I watched in stunned disbelief as Julie handed the brawny thug my phone, ID, credit card, and my thick wad of bills, which Jake immediately stuffed into his shirt pocket.

Jake's orders were stark and to the point. "You'll be working the hotel lot tonight. You stay right out in front of the room so Julie and I can keep an eye on you. You're young and blonde so you'll do okay. Julie will be setting up your tricks and collecting your money for you, so don't worry about cops or weirdos. Jake & Julie will keep you safe, love."

Jake sealed the deal by coming over and kissing me deeply, stuffing his tongue into my mouth. I pushed him away hard.

"I just wanted the clothes," I protested. "I'm not turning tricks for you. I'm not a whore!"

"You sure stink like one," Julie said, laughing.

"And you look like one, too," Jake snapped. "Listen bitch. Ya got no money, no phone, no money and no way out of here, except through Jake. I own your ass. And tonight, Miss Posh, you're going to earn your supper flat on your back with your feet in the air."

"You are mistaken, sir," I said, in my best high RP accent. "I am not a prostitute. However I promise to pay you a handsome gratuity upon my safe return to —"

Jake was not in the mood. Yanking me over his knee he exclaimed, "I don't negotiate with my whores." Jake had my short skirt up and my knickers down around my knees in a flash.

SPANK! SPANK! SPANK! SPANK! SPANK!

Julie laughed as Jake set my bottom ablaze. I had never been struck before but hand never supposed that a mere hand spanking could hurt so much. Soon I was kicking, crying, and showing the disgusting pimp my complete inventory. I'm ashamed at how quickly I buckled and to this day wonder if it was my shame or my excitement that made me cross this final line.

"Stop! Stop! Please! I'll do it. I'll do what you say!"

"Do what?" Jake demanded. SPANK! SPANK! SPANK!

"I'll turn tricks for you." SPANK! SPANK! "Lots of them!" SPANK!

"Why?" SPANK! SPANK!

"Because I'm a whore!" I cried out, sobbing with defeat.

"Prove it," he said, rolling me off his lap and onto the filthy carpet.

Thirty seconds later I was kneeling on the disgusting rug with his member in my mouth, filled with disgust as my pimp directed me through my first trick.

"Suck it good, whore," he directed. "Swirl that tongue around. Lick the first few drops off the tip. Now underneath -- it's really sensitive there. I can tell you're new at this but you'll learn. A bit more suction. That's a good girl. I'm letting you suck me bareback, because I know you're clean, but all the Johns always use a rubber. Is that clear?"

I bobbed my head as I slurped at his dick. "Yeah, that's a good girl. Now don't swallow my jizz when I squirt. I have something special planned. Here it comes."

I didn't swallow. He ordered me to smear his disgusting scum around my lips, the inside of my nose, and my upper lip and mouth, "so you can smell and taste your Daddy all night, and never forget you're mine." I wish I could say that the horrible odor in my nostrils drowned out my urine/disinfectant perfume, but the extra emission only added to the unbearable stink that swirled in my nostrils.

"You work until 10 PM," Jake said. "That will make you worth the trouble of breaking you in."

"Girls get lazy on the clock," Julie observed. "You should make her earn back the money she brought. You get sixty percent...and I should get another twenty percent for managing her. She can pay us back out of her share. You & I can split her tips, Jake.

I didn't understand why I had to pay back the money Jake had stolen FROM ME, out of a measly 20% of my proceeds no less, with Jake & Julie stealing MY tips. But with my ass still burning from the spanking and his scum in my mouth and on my face I was in no position to object.

Jake quickly counted out the money I had brought him -- an emergency stash of £600, less the money I had spent for bus fare and coffee. "That will keep her busy," Julie chuckled, clearly pleased that I had to earn so much!

As he pocketed my money Jake's voice was cold. "Turn her out," he said flatly. "Make her earn it."

Half naked and humiliated, the laughing Julie paraded me up and down in front of the hotel, my tits and ass bouncing as I pranced back and forth in my high heel boots. My clownish makeup made me look cheap, but my long coltish legs, firm tits, and youthful skin compared favorably to the older, cheaper, more battered whores I was competing against.

Within minutes I had my first customer. I learned the lingo fast: "Half & Half -- blow job and intercourse - with a disgusting geezer old enough to be my grandfather. It took forever to suck him up, and at £40 total that means I netted a measly £8. In the past I was always the owner, skimming my percentage off others work, but now the math that had once delighted me filled me with horror. I had to earn another £580 plus. Vicky really would be earning her keep with her legs spread and her feet in the air!

I needed to work faster. I was still pulling on my knickers when Julie pushed me back out on parade.

The next one, a manual, was faster, but I netted a measly £2 to jack off a fat man who promised me he'd warn me before he came but ended up squirting his load on my face. Jake was right -- hand job or not, always use a condom.

I had made a mistake picking the red light district closest to my estate, but I was glad for my garish makeup and cheap appearance. I actually knew who my 3rd trick was.

I didn't know his name, of course. He was a brawny Jamaican and I remembered him only because I had complained about the way he ogled me while I was sunning myself by the pool while he dug out a sewer pipe in the blazing sun. He had been fired on the spot.

I wondered if he remembered me but he didn't seem to. For a moment I actually considered asking for his help, but quickly returned to my senses. I doubted he'd battle my pimp to free me after what I had done to him. Revealing that I was the British aristo-bitch who had fired him would make fucking me all the more enjoyable.

I didn't know his name when he worked for me, but I would never forget it from this day on. Shamar ordered me to dance a humiliating striptease for him, peeling down to nothing but my best whorish smile. Then I got down on my knees to suck his 10 inches until it was as hard as black steel. Shamar's penis had a large bulbous head, which came in handy when for an extra £5 he became the first man to ever fuck me up the ass.

When I tried to explain I didn't do "that sort of thing", he laughed and told me already paid "the bitch outside for your tight butt hole, you stuck up bitch." He fucked me on all fours on the bed, facing the mirror. I think he wanted to see the look on my face: him laughing and grinning as I gritted my teeth.

My saliva had left his pink condomed shaft soaked, and the shame of the humiliation hurt me far worse than the penetration. He was rough, laughing as he pumped his thick cock in-and-out of me like a piston, enjoying the look of helpless degradation on my face as he porked me.

"You stink, whore," he said in heavily accented Jamaican, "But you look like fancy lady I worked for once. She had a mole near her titties like yours, and a red stain above her ass" he said, laughing as he slapped my butt. "But this is my plantation and I am the master here, white girl. Feel my cock inside you, whore? I stretch your tight ass good. Shamar your master now."

I turned my head as I heard a voice from the doorway. "That's it, Vicky, give him a good ride!"

"Yeah, give the John his money's worth!"

To my horror Vicky and a couple of the other girls were standing in the doorway, laughing at me as I got reamed. A sharp slap on my ass from Shamar refocused me on my job."

"Who in charge here?" Shamar demanded as he pumped my ass.

"You are...sir", I said meekly.

"Dat right. If Shamar call you in from field, slave girl, to fuck you up the ass, you run to my big house like dog. Shamar is yer master now."

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