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Becoming a whore [F20s/M40s/M50s] [Prostitution] [Outfit] [Dubcon] [Bondage]
Author Summary
hannah-always-horny is a male in Bondage
Post Body

Being a prostitute has always been one of my guilty fantasies. There must be a line where on one side, I'm a respectable girl, and on the other, I'm a whore. It's not clear to me where the line is, but I finally figured out a way to live out the fantasy, so I can go looking for it.

I've always been worried about being recognized if I would try out this fantasy. I don't want it to come back to me in my "normal" life. So my plan is to take the train to a bigger city, about 1.5 hours away from where I live. I'll go there, and work as a street walker for one night. I already scouted out the area, know how to get there, and where I'll stand and wait for customers. The only thing to do is to start.

I've packed a small bag with everything I'll need: A slutty whore outfit, some makeup, a large box of condoms, a small bottle of lube, some change, a small purse. I'm still wearing an everyday, comfy outfit that nobody will look twice at. It's late afternoon on friday, and walking to the train station, getting a ticket, and sitting down into the train, I can hardly believe I'm doing this. My heart is beating fast, and my mind is racing: Am I really about to live out one of my secret fantasies? Will I really be a whore after this night is over?

Nobody looks at me twice when the train finally rolls into the station, and I get off, following the flow of people through the station. I make my way to the toilets, pick a stall, and lock the door behind me. I feel a mix of nervousness and excitement, and quickly start to dress in my whoring outfit. First, a pair of black fishnet stockings. I picked the tiniest, most see through, pair of underwear I could find: Just a g string barely covering my pussy, and a bra straining to hold my boobs. Both are so lacy that anyone can easily see my nipples and pussy through them. Then, I slip on my skirt, a pleated, short schoolgirl skirt that just barely covers my ass cheeks when I stand upright. As top, I wear a cropped, slightly transparent white blouse. And to finish the outfit off, I chose ankle high high-heeled stiletto booties.

I do my makeup next, trying to concentrate. Bright pinkish-red lipstick, heavy eyeshadows and blush. Everything about me should scream "whore" and "slut". My little handbag is easy to pack: Just a bit of cash so that I can give out change, and then I dump the whole box of condoms into it. I check myself: Fuck-me shoes, fishnets, a really slutty schoolgirl outfit, whorish makeup, and a tiny handbag filled with condoms and a bit of cash. Everything about me screams "whore", at least as much as I can make it. I quickly stuff the rest of my clothes in my bag, take a deep breath, and open the door. I feel a flush of arousal as I feel my hips swaying as my heels click on the tiled floor. I deposit my bag into a locker and make my way to the street to take the space I picked out, carrying only the little handbag with condoms, lube, and a bit of change.

Wearing this whorish outfit there's no way I'm getting lost in the crowd. I can hear all kinds of reactions as I walk past people: Tutting, disapproving noises from older people. Other girls giggling at each other, not so quietly saying "What a whore!" Men eagerly staring at me, clearly wanting to fuck me. Groups of guys catcalling me. I feel on display, almost like I'm wearing a price tag. The feeling turns me on, but soon, I have to walk through a few quieter side streets in order to reach the spot I picked. Here, I feel different: Vulnerable, like a little rabbit walking out in front of wolves. There are not many people around, but the few men I see seem rougher. For a little while I hear footsteps following me, and my heart starts beating faster, but he turns away after all.

Finally, I reach the spot I picked out. It's near the start of a street clearly in the hands of prostitutes: There are a few girls already standing at the road, in outfits like mine. Along the road, there are a few seedy looking hotels that rent rooms by the hour. Every now and then, cars with open windows roll by slowly, the man inside checking out the girls. I feel excited and nervous when I make it to the spot I picked earlier. I stop walking, and just stand at the side of the road, tilting my hip a little in a suggestive pose. I'm a whore, standing on the side of the street looking for customers. But no, if I leave now, nothing actually happened, right? Does this really make me a whore already?

A few cars go by, but the men inside stop and pick up other girls. But standing here, being ogled by them, feels different: Before, my outfit was only implying I was a whore. But by standing here, at this street, it's clear that men can buy my body. Fucking me is now just a matter of paying enough. I'm almost lost in thought, enjoying the feeling of standing here, when a car slowly rolls to a stop next to me. Is this it? Am I about to have my first customer? I smile as I walk the few steps to his car, and lean forward. "Hey there, are you looking for some fun?" He's older, muscular but with a slight belly, wearing a T shirt and jeans. He smells faintly of sweat and cheap cologne. Normally, I'd be turned off by a man like this, but for now he seems to be just the right type of man... His voice is deep and rough, and he haggles me down a little bit while discussing what he wants. I agree though, and open the door to sit down next to him. My short skirt slides up as I sit down, and the car seat feels slightly oily and dirty on my bum, for the short drive to the next seedy hotel.

The man, my first client, wraps his hand around my hip when he leads me into the hotel after parking the car outside. The clerk doesn't even look up while booking us into a room for the next hour. To him, I'm just another whore! My client leads me to our room, and my heart beats fast when he closes the door and locks it, while I sit down on the edge of the bed. For a short moment, he's just standing there, looming over me, then he pushes me down onto the mattress, and pulls up my top and bra. He immediately starts to grope my boobs roughly, kneading and pinching them. I moan out, not only because he expects it but because I'm turned on: This man is paying to use my body. In a few moments, he will fuck me, and then give me money for it...

I fumble his belt and jeans open while he gropes my boobs, and just pull the front down with his underwear, letting his cock plop free. It's already hard, he's clearly looking forward to fucking me. I get a condom from my little handbag, and rip open the packaging. He grumbles quietly, but allows me to put it on him, especially as I gently massage and caress his cock and balls while I do it. Like him, they smell faintly of sweat, but serving someone I don't really find attractive as a first client seems appropriate, and the whole situation turns me on.

It's time, and I'm actually panting slightly: I slide the last thing covering my pussy away, dropping the tiny g string onto the edge of the bed, and lay onto my back, spreading my legs, inviting him to come and fuck me. My short skirt falls up, and my whole body is laid out in front of him, on display and his to use for the next hour, if he wants. And the only thing he had to do is pay for my body. My first client wastes no time: He gets between my knees, slides his cock between my pussy lips, and pushes his hips forward. His cock slides deep into my pussy, and I moan out loudly, throwing my head back. He starts to fuck me with forceful thrusts, slapping his balls against my ass. I'm moaning and panting without needing to pretend, getting fucked by my first client as a whore is such a turn on! But before I can cum, he gives a few deeper, harder thrusts, before thrusting deep into my pussy. His cock starts to twitch, and the only thing preventing his cum from flooding my pussy is the thin latex sheath of the condom.

When he's done, panting and bent over my body, I gently slide his cock out of my pussy, and slide the condom off of his cock. I use a tissue from the box on the nightstand to wipe his cock clean, then throw the tissue and condom in the trash. I just serviced my first client! My mind is racing, and I don't pay a lot of attention while he does up his pants and belt again, hands me my pay, and leaves after saying a gruff sounding "Thank you". I sit on the edge of the bed for a while, holding the cash in my hand, feeling excited and aroused. I just serviced my first client. I'm a whore now. I will always be a whore now. I put the money away, put on my slip, pull down my bra and top again, and get back to my spot on the street.

I service two other clients in the next hour: One of them looking like a distinguished businessman, who takes me to a different hotel to fuck me, and gives me a large tip. The other one is a young guy, who tries to haggle my price for a blowjob in the parking lot down, but ends up agreeing to pay full price, after I offered him to shoot his load over my boobs. Standing back on the street, they still feel a little sticky inside my tiny bra and top, even after wiping his cum off with tissues.

Then, another car slows down next to me. It's a convertible sports car, with a tanned gym bro sitting in it. He wastes no time, even while I still take the few steps to his car, he asks out loud: "Yo babe, I wanna fuck your ass. How much?" He flashes a bundle of cash at me as I bend down. His brazen demand, making it clear that I'm a whore to anyone within earshot, sends a tingle through my body. He agrees to my price without hesitating, and after I sit down next to him, he speeds off to the hotel where my first client took me. He just walks in, expecting me to follow, and quickly rents a room. The clerk still doesn't look up. I'm still just a whore to him.

The gym bro just swaggers along to the room, and I follow him. He locks the door behind me too, and immediately turns around, dropping his shorts. His cock springs free, and I genuinely gasp: I'm not an anal virgin, but he's easily the biggest one I've had in my ass! But he's paying, and I'm horny enough to give it a try... "Bend over the bed, babe." He points, and I get on my knees just in front of the bed on the grimy carpet, laying my body down on the bed. My skirt slips up over my hips, and my ass is on display for him, only the thin strip of the g string covering my asshole. I pull out the tube of lube I brought, and he grabs it, pulls my g string down to my knees, and squirts a bit of lube onto my asshole. He spreads it around with his finger, sliding one inside of me briefly: "Holy shit you're tight, for a whore." Then he positions his cock against my asshole, and I concentrate on relaxing it as much as I can.

He doesn't waste much time, but immediately starts to push forward. The lube helps him slide into my sphincter, and he spreads my tight asshole open more and more, until finally, he slips inside of me. I grip the mattress and bury my head into it, groaning out as he violates my tight ass with his huge cock. I don't even think about how many other whores already got fucked on the mattress, only how much he is spreading my asshole open. He starts to thrust, fucking my ass deep, until his balls slam against my pussy, then pulling out almost all the way again. I still grip the mattress, it feels like he is splitting me open each time he thrusts, but I lift up my head and look back at him: "Ooooh god yes, fuck my ass just like that!" I fake-moan and gasp, mixed with a few real groans, while he clearly enjoys himself. He has good stamina too, and keeps fucking my ass for what feels like an eternity, while I fake-moan and writhe beneath him, pinned at the edge of the bed. Finally, he lets out a loud moan himself, and I feel his cock pulse inside of me, emptying his load in my ass. He withdraws, and I'm left panting, bent over the edge of the bed, glad that he's done. My ass feels like it's red and gaping... He wipes himself off with one of the tissues, just drops it next to my face, and then throws the payment we agreed on earlier next to it. "Thanks, babe. I'll tell my bros where to find you, that was great." With that, he's gone, and I'm left to clean up after his cock. I clean my ass as well as I can, wipe up the cum that's dripping out. He definitely left me gaping a little, and it feels like I'm walking bowlegged when I make my way back to my spot again.

(Continued in comment)

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4 months ago