The first time whore (for Rocket1010)

LenaDoll

Slutty fucktoy
Joined
Aug 25, 2026
Posts
10
I had fantasized about this for a long, long time. But I never dared to go through with it. Not until now, not until I had moved into another city. A city where I knew noone, far enough away from anyone who might recognize me. But now? Now is what feels like the perfect time to go through with one of my deepest sexual fantasies. The perfect time to work as a prostitute. To become a whore.

I have it all planned out in advance. I bought a cheap, slutty outfit. Not something I would usually wear, but perfect for this: a tiny little lace thong and matching bra, just barely enough to cover my pussy and nipples, and almost completely see thru. A pair of stockings, going up to mid thigh, topped with lace. A tiny skirt, just barely covering my ass cheeks, riding low on my hips, pleated and checkered. A tight white crop top, half a size too small for me. A tiny denim bolero jacket. A pair of black leather stiletto booties, ankle high and decorated with rhinestones. And lastly, a tiny handbag, stuffed with a pack of condoms, and a few bills of cash for giving change.

All of that was in a duffle bag when I left home and took the bus to the train station. There, I went into one of the stalls, and quickly changed, putting my normal street clothes into the duffle, and changing into my whore uniform. I quickly did my makeup in the dirty mirror, intentionally overdoing it a bit. I'm aiming for slutty, whoreis, not well done makeup. When I step out of the railway station toilet, I feel different. Cheap. Slutty, For sale. Like a whore. I quickly stash my duffle in a locker and lock it, the key the only other thing in my tiny little handbag other than condoms, and cash.

My heart is hammering as I make my way to the street I had scouted before: The street that all the street whores were standing on, waiting for clients. The one that everybody knew but nobody talked about. Luckily, the subway was mostly empty, so I got there with just two or three catcalls by men late from their shifts. I feel equally anxious and excited, will I meet one of them as a client later?

Walking the last two or three minutes through the empty streets to the spot I picked, I feel surreal, like I'm floating. I'm excited, but also nervous. My stomach is fluttering, and I feel a wash of arousal. Soon, I'm going to stand on the street to get picked up, like a whore! Soon I'll be a whore! I try to imagine the clients I'll get while I walk, my stiletto heels clicking on the pavement, echoing in the cool, damp air. Rich men, looking for a cheap thrill? Older men with dead bedrooms, pent up and looking for release? What if it's someone unattractive, or a worker, sweaty and dirty on the way home? What if he doesn't want to use a condom? What if a pimp decides I'm on his territory, or the police decide to do a shakedown?

Then I reach the spot I have chosen. I swallow down the lump of nervousness in my throat, plaster on a fake smile, and stand beneath the lonely streetlight on the corner. Waiting for a car to stop. Waiting for my first client to stop, waiting to become a whore.

(Feel free to also send me a private message if you prefer that :) )
 
Ben Anderson was cruising the streets looking for some fresh women for his escort service. He had a few gals who worked for him and some people called him a pimp. But he wasn't really a pimp. He was a provider of women for men to have a good time and operated one of the premier escort services in town. His gals were discreet and while he had a good business, he was always on the lookout for new talent.

Some of the escorts came to him with recommendations from his group of women. But sometimes he cruised the street of the city late at night to see if there was a potential escort working the street. He recognized a lot of women who roamed the streets late at night looking for a man wanting to have a good time. And he had taken a few of them up on their services and found they were not what he was looking for. And then there were the real pimps who controlled the girls under their thumb. Once he found a woman working for a pimp, he was hands off. He knew the pimps and they had a silent agreement that Ben would not try to convince the woman to work for him. One thing Ben didn't want to do was start a turf war.

Cruising the street, he saw the usual women trying to entice a man in a car who had stopped at the curb. He was about to give up when he turned a corner and saw a women standing under a street light in a sexy outfit. He slowed down about a half block from the woman and watched her. He saw she was wearing a skirt that barely covered her ass and a denim bolero jacket that covered a white crop top. He also saw she was wearing thigh-high nylons and ankle high stiletto booties. He chuckled, seeing the boots were decorated with rhinestones.

To the untrained eye of a normal man looking for a hooker, she was just what they were looking for .... a slutty looking whore. He thought about driving past her without any interaction but there was something in the way she stood on the curb that caught his attention. To him she was definitely a novice and if she wasn't careful, a pimp or some deviate could snatch her up and she would be either made to work for pittance or even hurt badly.

Studying her for a few more moments, Ben decided to take a chance and see if his original assessment was correct .... she was a novice. There was a slight mist in the air as he pulled his vehicle to the curb. She was staring at him and he knew she was new to the streets. But was she good enough to be part of his escort service. There was only one way to find out.

Rolling down his window he acted like a normal john, smiling at her, seeing her bend over, showing him a nice cleavage she was presenting to him. "Hey .... I know a nice quiet place we can go to ger acquainted and get out of this weather. How much do you charge?" He waited for her answer wondering if she would tell him her quickie rater, hourly rate, or would she give him a cost for all night.
 
Standing beneath the streetlight I quickly realize that I can't see that far outside of the light cone. The bright light that illuminates me makes it a little hard to see the dim and dark spaces around it. I hear a few cars pass by, and I see them when they get close. So far, none have stopped. With each car going by, it feels like I can sense the man inside checking me out, judging if I'm worth his money and time.

Then, suddenly a car stops next to me, and the passenger window rolls down. My heart starts pounding, and I feel my cheeks flush. This is it! I saunter to the window with my hips swaying, and lean over. My skirt rides up my butt cheeks, and I hope that noone walks behind me for the next few moments. At least, my cleavage is great I think, pushed up and forward by the tight bra and tank top combination.

"Hey, handsome!" I wink at you. "For you, it's 25 for a blowjob, 50 for sex. If you want more, we can always find a price we agree on." I wait with bated breath. My prices were more-or-less random, based on the best research I could do, but it was difficult to get a feeling for how much to charge. Will he go for it? If yes what will he choose?
 
I see your sexy smile and smile back as you wink and tell me a blowjob is $25 and $50 for sex. When you add that we can find a price we can agree on, I instantly know you are under selling yourself. Girls on the street make more than unless they don't have a pimp to work for. With a pimp the price is higher because they take a higher percentage.

I could see a certain uneasiness in your eyes as you waited for my response. "Sounds reasonable baby. I think I want more than just a blowjob or sex."

There was something about you that struck me in a good way. I got a gut feeling you could be one of my best escorts. I wasn't sure why but it was just a good feeling. I had a feeling you were fresh and not burdened with past encounters with men.

"How about I pay you $500 for the night. I know of a nice motel close to here and we can get a bottle of wine and have a good time tonight." As I wait for your answer, I wonder if you have a pimp, or boyfriend, or husband. When I see you thinking about it too long I add quickly, "Come on honey make a decision. The cops don't take kindly to guys and gals like you and me. What do you say ...... $500 for a night of fun." I see you mulling over the amount and wait.
 
My mind is racing when I hear your offer. $500 for a whole night is a nice sum of money, but can I trust you enough? Somehow standing here in public seems safer. But then, I would always have to go with a client, wouldn't I? And am I really sure I can manage at least 10 clients tonight, to make up for your offer? I haven't even had any other offer apart from yours!

I come to a decision. "Sure, handsome, that sounds good!" I open the passenger door of your car, and get inside. Sitting down, my short skirt hikes up my butt cheeks, and I feel the fabric of the seat directly on my ass. I give you a wink. "Let's go, then!"
 
I see you struggling with my offer and smile when you make your decision. I watch you slide into my sports car , seeing your short skirt ride up, revealing soft thighs.

I can’t see what you’re wearing but I’m guessing it’s either a string bikini bottom or a thong. When you give me a smile and wink and say "Let's go, then!" I sense you’re trying to act as if you did this a hundred times.

Putting my hand on your bare thigh I squeeze a little and move my hand up and down your thigh. I feel your leg tighten up a little and wonder if you’re going to go through with being a hooker.

I keep my hand on your thigh and drive away from the curb. “I think you and I are going to have a great time tonight baby,” I say squeezing your thigh again.

It doesn’t take long to get to the Westside Motor Lodge. It’s a nice place I own and I keep a suite ready for me whenever I want it. I also own some high end hotels my gals use for business. But this is where I always take new girls the first time so they don’t get scared.

“Here we are baby,”. I hustle out of my side of the car and open your door. I still see a bit of nervousness on your face. “I can’t wait to get you inside baby and have some fun.”

Opening the door to the suite, I turn and take you into my arms. My hands reach under your short skirt and cup your bare ass, feeling my cock start to harden. “How about a nice kiss to get us started?”
 
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