"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."