Pamela stood huddled in the dark doorway, halfway down the back alley. It was cold and a light drizzle had settled in, the sheets of fine rain just discernible in the dull light of the single working lamp halfway down the alley.
Pamela was in her mid forties and fighting a losing battle against the rising tide of age, her thighs and bottom were spreading, her tummy had started to sag and fine lines, not quite yet wrinkles, had recently appeared on her once pretty face.
That being said she was still attractive in a mature unpolished way. She knew how to display her best assets to their full benefit. She had great legs despite her thickening thighs, and to exhibit them she always wore high heels, sheer stockings and the shortest of skirts.
Her spreading tummy was held in place with a full girdle with attached suspenders. Her ever expanding, slightly saggy breasts could be controlled and displayed to advantage with the right bra. Her face just needed more makeup than she used to use when she was younger, so she wore lashings of it. Finally her hair was always perfect, no demure bob or modest perm for our Pamela; she wore her hair big, high and sassy. 'Mutton dressed as lamb, ' her Mom would have called her; but that was Pamela's look. Her regular punters loved it.
Pamela had been a prostitute all her working life. She had held the odd regular job here and there, but always came back to the game. From the moment she had turned fifteen when she noticed the boys furtive glances at her breasts and her uncle Bill's awkward but repeated attempts to look up her skirt and the lump in his pants when he hugged her (which he tended to do way too often and for far too long for propriety); she knew that she had something men wanted. It didn't take her long to figure out that they would pay for it too. She fell into prostitution the way some of her girlfriends fell into jobs such as hairdressing or as shop assistants; it was just the job that best suited her.
Pamela had started working at her aunt Doreen's modest establishment when she turned sixteen. Her mom had raised no objection. To supplement her meagre wage, every now and then her mom had taken in the odd lodger who sometimes paid extra for the privilege of sharing her mother's bed. Her dad had run away when she was still in nappies and she didn't remember him. Pamela dutifully gave half of everything she earned to her mom.
At Aunt Doreen's she had learned the ropes so to speak. At first most of her customers were men who wanted a younger, prettier girl than their wife or current girlfriend. As she grew older she got the men who wanted an experienced woman who would do all the things for them in the bedroom that their wives and girlfriends wouldn't do.
Pamela would do almost anything within reason providing the punter paid her enough. She had done some kinky things in her time, everything from mundane requests for fellatio to dressing punters in frilly knickers and spanking their bums. In fact light bondage and discipline work was her forte and she often took down punters into the special 'dungeon' room in the basement. However she would have nothing to do with the heavier, perverted stuff that was sometimes requested.
She refused any requests for sodomy, role-playing involving rape or incest, heavy sado-masochism; and as for anything involving pissing and other dirty acts; who were these perverts anyway? Go to Germany for fuck sake! The Germans seemed to make all the 'adult' movies involving those revolting acts.
In her mid thirties Pamela's mother had died and she had finally moved out of her mom's old home and at the same time moved out of Doreen's establishment. She set herself up in a nice little flat and only saw her regular customers or those punters who came to her recommended by trusted friends. In her late thirties and her early forties her regulars had dwindled away to almost nothing. They had moved on, found younger women, or just stopped paying for sex. Older and bolder but still attractive enough to pull the punters she had started working the streets.
She could get a legitimate job and with the added income from her few remaining regular customers she could probably make a decent living working at one; but Pamela was prostitute; that's what she did best, so that's what she did.
Life on the streets was harder, but Pamela was no mug. If a punter was nice and looked like he had enough money she took him home for a 'full service'. If the punter only wanted a quickie, was half pissed, or didn't have the money for a full service she would blow him or have him fuck her standing up in the doorway. The doorway in the dark disused alley had become her workroom. She would stand on the main road displaying her wares and until she hooked a short timer, then she would lead him down the alley and into the doorway to complete the transaction. The better clientele had a short walk to her flat.
Pamela, like all prostitutes, had had her share of bad experiences. Safe in Aunt Doreen's brothel there was always help at hand and the worst that had happened had been the odd abusive punter when she'd turned down a request for perverted sex. In her flat she only serviced regulars; but on the street it was different; she had had to deal with all sorts.
Occasionally a punter would try to get a freebie, but she soon learned to take the money as soon as she entered the alley and before her and the punter got to the doorway. Sometimes if the customer was too pissed or couldn't come for some reason they demanded their money back. Once a punter had slapped her face and called her a whore before running off into the night, but mostly Pamela could handle any situation.
On this cold wet night Pamela's life was about to change forever. Tonight she had invited the wrong punter down into the alley.
Pamela had been about to give up for the night when a punter approached her where she stood at the entrance to the alley. She had watched him walk past two or three other working girls who were huddled in their usual positions on the street. He looked them over and continued on until he came face to face with Pamela. He looked her up and down, surveying her from top to bottom.
Pamela was dressed in a white silk blouse under a short red leather jacket, a black leather miniskirt came to mid thigh, black seamed stockings, and matching red high heels completed the ensemble. Her hair was teased, and framed her mature but attractive face. She was heavily made up with lashings of eye shadow, mascara and eyeliner to accent her pretty blue eyes, her cheeks were heavily rouged and she wore bright red lipstick. The punters liked their girls to look 'slutty'; it added to their fantasies she thought.
"Now you're my type of girl," the man breathed whisky on her.
Pamela appraised the punter. Dark business suit, mid forties, just going to fat, heavy but handsome, a little drunk but sensible. He would do for her last quickie before she went home.
"Glad you like what see darling; it's sixty for short time ok," Pamela made her pitch.
"Fucking expensive for an old pro like you ain't it?" was his response but he stayed put and continued to gaze up and down Pamela's body.
'The ones with plenty of money always argued about the price, ' she thought.
"Look it's sixty; short time in the alley. Take it or leave it; I'd as rather go home anyway!" Pamela snapped back.
"Ok! Ok darlin'; I'm hot to trot and your just my type, lets have you then," another cloud of whisky enveloped Pamela.
"Follow me, what's your name?" she lead him just inside the alley.
"Mike," he replied.
"Let's have the money Mike; then you get your honey ok?" Pamela gave him her best false smile.
Mike fumbled for his wallet and handed over the sixty. Pamela saw the wad of cash he had in his wallet and thought 'Cheap fucker'.
Pamela took Mike's hand and as she led him into the gloom of the alley, as they walked into the gloom Mike placed his hand on Pamela's bottom and pinched; she brushed it away irritably.
"Hold your horses lover; here we are," she whispered as they entered her doorway.
The doorway was recessed far back into the disused building and no one was able to see them unless they came all the way down the alley. Pamela had never been disturbed here yet; then why would she? The building was disused.
Mike turned Pamela to face him and eased her back against the door; he pushed himself against her and tried to kiss her. She pushed him back and turned her face away from him.
"No lover; no kissing Ok? I don't do that with punters."
"What do I get for my sixty then?" Mike asked his face puffed up and reddening.
"You get oral relief, and if you want you can shag me Ok?" Pamela offered her standard services.
"Can I fuck you in the arse then?" her customer went on insistently.
"Look sweetie you can have what I just offered; if that's not to your liking take your money and fuck off; it's fucking cold and I'm tired!" Pamela laid down the law. What she didn't need was the last customer of the night to be a difficult bastard.
"You slags are all the same," Mike cursed; "you come on all dolled up to get a guy horny then you won't play the game properly. How can I shag you without a bit of a kiss and cuddle first hey?" Mike insisted, his voice getting angrier.
"Look I'm no slag and if you don't behave you'll get nothing ok?" Pamela had had enough.
"Alright, alright, give us a suck then sweetheart." Mike capitulated.
'Thank fuck for that' though Pamela 'let's get this over with and get home to bed.'
.... There is more of this story ...
Ma/Fa / Ma/Ma / Mult / NonConsensual / Reluctant / Rape / Blackmail / Drunk/Drugged / Heterosexual / TransGender / CrossDressing / Fiction / BDSM / DomSub / MaleDom / Spanking / Rough / Humiliation / Group Sex / Oral Sex / Anal Sex / Masturbation / Foot Fetish / Leg Fetish / Violent / Transformation / Prostitution /