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 dis
play 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.’
Pamela dropped to her knees, placing them on an old cushion she had bought to the alley not long after she first established the doorway as her 'workroom'. She had laddered her stockings kneeling on the bare brick floor the first night she worked here. Her face was level with the punter’s crotch and she reached up and unzipped his fly. Mike looked down at the overly made-up whore as her red fingernails slid down his zip and reached inside his trousers.
Pamela’s fingers freed Mike’s already thickening member from his underwear and pulled it out of his flies. ‘At least he’s nearly hard; he shouldn’t be too long coming,’ she thought; ‘not a bad sized one either,’ she couldn’t help thinking.
Mike watched as Pamela slowly stroked him until he was fully erect and then sighed as she bobbed her head down and took him in her mouth. His perfect fantasy was playing out perfectly in the dim gloom. A lovely older woman dressed as a tart was kneeling before him suppliant to his carnal needs. Mike looked at her heavily made-up face and pretty eyes as she looked up at him. Kneeling as she was, he got a great view of her large arse encased in the black leather mini and her seamed stockinged legs; he loved her red high heels, so whorish.
Pamela saw that Mike was staring at her face and body as she fellated him; she knew that punters liked to do that and she made a point of looking up into his face; she knew that really got them aroused. Hopefully this dickhead would come quickly she thought. Then she felt his hands on either side of her head. He held her in a vicious grip and began to brutally fuck her face. She couldn’t move her face away from his crotch and she was gagging on his cock as it forced its way all the way to the back of her throat.
Pamela started to pummel Mike with her hands as she gagged on his penis. Mike just held her tighter and continued to enjoy fucking her mouth.
"You love this don’t you, you whore. Don’t pretend you don’t. You’re all the same, you say you won’t do this and you won’t do that, but what you really want is good hard dirty fucking don’t you?" Mike was raving now.
"No kissing! No anal! Who the fuck do you think you are; I’ve paid my money and I’ll take what I want," Mike hissed as he held Pamela’s head in a vice-like grip and fucked her mouth.
Pamela had no choice, she couldn’t breath and Mike's cock was choking her, so she bit down on it. Mike screamed and pushed her away; Pamela lay sprawled in the doorway flat on her behind, her legs spread, her skirt rode up to reveal her stocking tops and red nylon panties.
Mike quickly recovered from the nip he had taken on his penis and looked at Pamela fallen flat on her arse before him. He looked up her skirt and his cock began to harden again; he looked at her heavily made up face and knew he hadn’t taken all he wanted from this whore.
"Fuck off!" Pamela shouted at him, "Fuck off and leave me alone!" she begged, hoping her cries would be heard by someone passing the alley. She knew her hopes were forlorn.
Mike moved in to take what he wanted. He reached down and slapped the whore hard across the face bringing tears to her eyes, she sobbed and her makeup started to run; her crying only served to arouse him further.
"Please, please don’t," Pamela pleaded, knowing she was in deep trouble.
"Yeah, that’s it bitch; you say please! You say please and I might be nice but don’t worry Mike knows what you need," he growled.
Mike dropped down between Pamela’s spread legs and reached up under her skirt and grabbed her panties. He tugged and pulled on the flimsy nylon garment until they tore free from her body. Mike bought the sheer panties up to his face and smelled the crotch; then he wrapped them around his tumescent member and gave it a few stokes.
"Nice knickers bitch; they're lovely."
Then he reached out and stuffed them in Pamela’s mouth. She tried to move her head from side to side but he slapped her again and pushed them deeper into her mouth, effectively gagging her. Then he grabbed her ankles and pulled her forward so that her spread legs straddled either side of his body; Pamela fell back hitting her head on the ground.
Mike had Pamela positioned prone in front of him with his throbbing cock inches from the entrance to her vagina. He pushed forward and thrust himself inside; right up to the hilt; Pamela groaned through the gag.
Pamela was dazed from the slaps she had received and from hitting her head on the pavement but when Mike lifted her legs around him she knew what was coming next. She braced as she felt Mike's huge member push past her labia and rudely thrust deep inside her. As a prostitute she had obviously succumbed to hundreds of erect penises inside her before, some a lot bigger than this; but this was different, she was being raped and she felt defiled.
Mike started to fuck Pamela with slow hard strokes enjoying her tight vaginal walls around his cock and loving the feel of her silken stockinged legs against his body. He was pleasuring himself at the expense of this whore. ‘What was it she said? No kissing right?’ he thought, then leaned forward and breathed his whisky breath into her face.
"I’m taking out the gag but if you scream I’ll knock you out you fucking bitch!" Mike panted as he continued to fuck her.
He leaned down over her and pulled her legs up around him in the missionary position and positioned his face in front of hers and took the panties in his teeth pulling the panty gag out of her mouth. Pamela gasped for fresh air but not for long as Mike started kissing her in a frenzy. He pounded his cock in and out of her in time with his tongue as it slid around her mouth. His hands ran up and down her stockinged thighs, laddering her expensive diaphanous stockings with his nails.
Pamela didn’t know what was worse, having her panties shoved in her mouth as a gag or Mike’s fetid breath and slimy tongue as he kissed her. His fingers were scratching her legs and tearing her stockings to ribbons. His penis continued to slide slowly in and out of her, she almost wished he would speed up the fucking and get it over with. ‘Maybe that was it?’ she thought.
Mike noticed a subtle change; Pamela was no longer struggling; in fact she was returning his kisses. Her arms had moved up to embrace him and she was rising her arse up against him to meet his thrusts. She was fucking him back!!!
"You fucking slut whores, you’re all the same, you just can’t get enough dick can you?" Mike groaned.
Pamela continued to play her game, ‘Get this guy off and then get to the police,’ that was the plan now!
"Yes Mike; give it to me honey; you know I need it," Pamela lied, convincingly she hoped, whispering into Mike’s ear.
Mike was lost in the pleasure of fucking this whore when a little alarm bell went off in his head.
"You fucking bitch! I know what you’re fucking doing! You need it hey? Well let’s see how bad you need it baby!"
With that Mike pulled himself off Pamela and looked down at her. Her coat was opened and he had managed to tear open her blouse revealing her large white breasts. Her skirt was dirty and rucked right up around her waist to reveal her red garter belt which were attached to her sheer black nylons now in tatters on her bleeding thighs. Mike groaned with pleasure at this picture of a woman ravished.
Mike reached down and grabbed Pamela by the hair and pulled her to her feet. He spun her around and slammed her face first against the door.
"So you need it do you whore! Well here it is!"
Mike kicked Pamela’s legs apart and positioned himself behind her. He pushed his now rock hard penis between her fleshy buttocks and rubbed it up against her fleshy labia to coat it with her cunt juices then pulled back and started to force it into her back passage.
Pamela couldn’t believe the excruciating pain she was feeling as Mike invaded her with his weapon. She tried to relax her sphincter but Mike just kept pushing himself slowly and steadily inside her. She thought that she felt herself tear and she screamed again at the intense pain.
Mike was passed caring about her screaming; he was living his ultimate fantasy raping this fat cow.
"Yeah baby that’s it; take it for Mikey; take that cock!" he chanted over and over.
Eventually he forced himself inside her as far as he could get, his crotch hard against her soft fat buttocks. Then he thrust in and out as slowly as he could, but he couldn’t hold back; the pleasure was just too much. He pushed forward and buried himself to the hilt in Pamela’s arse and exploded. Stream after stream of hot semen shot from his cock deep inside Pamela’s arse. Mike grabbed Pamela’s face and twisted it around so he could kiss and lick her as he shot his load.
Pamela was now numb with pain. She was barely conscious and only just aware of Mike anally raping her. The only thing keeping her on her feet was the pressure of Mike behind her as he fucked her and her will power to stay conscious. Then she felt him take a mighty lunge and bury himself even deeper inside her and she felt her insides tear again, the hot flood of Mike’s semen increased the pain of the wound. Then the sick fuck was kissing her. This maniac was kissing her whilst he raped her.
Mike collapsed against the prostitute as his orgasm subsided. He eased himself out of her and reached down and picked up the shredded red nylon panties off the ground. He wiped his deflating penis on them and spun Pamela around to face him. Her face was a mess, her makeup spread all over it. She just stood there in a daze.
Mike kissed her gently on the lips then pushed the come soaked nylon panties into her mouth, leaving half of the flimsy garment hanging out.
"Don’t forget your knickers," he laughed.
"Thanks for the fuck; keep the money bitch," he mocked as he disappeared up the dark alley.
Before she passed out Pamela made a vow: ‘This Bitch is going to get revenge!’
It took Pamela three months to recover from her ordeal. Somehow that night she made it home to her flat and called her Auntie Doreen who came straight around. Doreen didn’t ask her niece what had happened, she didn’t have to; it was obvious. Pamela never told her Aunt the details of what happened, she was too humiliated. Pamela’s wounds, internally and externally, healed quite quickly; it was her mind that took the time. She eventually regained her self-confidence and was capable of leaving her flat to shop and so on, but she needed to work; and there was only one thing she knew that she was good at. It was Pamela’s resolve for revenge that kept her going and got her through.
‘This bitch is going to bite back; one day I will find him and he will pay for what he did to me,’ became her mantra.
Pamela discussed going back on the game with Aunt Doreen who refused to entertain the idea of her niece working the streets again.
"I’m in my fifties now love, come back and work at my place, it won’t be long before you can take it over, I’m getting to old for this game anyway," she implored.
And so it was. Pamela went back to servicing punters at Aunt Doreen’s brothel. There was security there, both in the numbers of girls on a shift at any one time, and from Doreen’s live in boyfriend Steve. His nickname was "Iron Bar Steve" and he had once done a stint in Chelmsford prison where he worked as a 'hard man' for Eddie McManus who was the hardest man there and ran the jail from the inside. Steve was the bouncer at Doreen’s establishment and he kept the punters in line if they played up. Steve had been living with Doreen for nearly twenty years (except for his stint in Chelmsford); he was only in his forties, nearly ten years younger than Doreen but they loved each other, and Doreen confided one night after a few gin and tonics, that she still kept Steve more than happy in bed. In fact, she implied, they both enjoyed a very exciting and varied sex life.
Six months after she started working again Pamela got her chance for revenge. She was walking past one of the rooms in the brothel when she heard the unmistakable voice of her rapist coming through the door. It was Mike! He was ranting at Susan; the poor girl had him in room number two as a customer.
"You’re all the same you slags, dressed up in your sexy gear leading a guy on and then won’t do what he wants. Bitches! Fucking bitches! Now get over here and suck my cock!" he ranted.
It was him alright! The memories of the evening Mike had raped her in their alley came storming back.
Pamela’s heart began to race and she ran down the corridor to Doreen’s office.
"It’s him; the bastard who raped me. He’s here, he’s in room two with Susan!"
"Are you sure? Mike’s been a coming here for years off and on, he’s a bit rough but I never took him for a rapist?" Doreen asked, a concerned look on her heavily made up face.
Pamela broke down and fell into her Aunt Doreen’s arms sobbing, she told her every detail of what that man had done to her on that cold wet night. Doreen poured them both a stiff drink and they began to plot Pamela’s revenge.
"Revenge is dish best eaten cold," quoted Doreen, "Let's make the punishment fit the crime," she added.
Doreen and Pamela waited a week; during this time they planned Pamela's revenge and acquired the necessary items to ensure the punishment fit the crime. Mike was obviously a vicious woman hater; his litany of 'Bitches dressed up in sexy gear who won't do just what he wants,' was to become the basis of their planned revenge; a theme if you like.
During this time Doreen enlisted Steve's help; he was instrumental to their plan. Of course when Doreen told Steve what Mike had done to Pamela, Steve just wanted to smash his head in "I'll castrate the bastard!" he said; but Doreen went on to explain how her and Pamela's plan was so much better. And so, the trap was set.
Mike made his called the brothel about a week later and asked to see the sexiest girl available. Doreen took the call,
"Mike, you have been such a valuable and reliable customer over the years that I've booked you in for a special treat. My prettiest girl and I'll let you have an hour with her for the cost of your normal half-hour session."
"About fucking time you gave me something; I've been coming to your shit-hole knocking shop for years now and I have to tell you I never had anything for nothing and your slags always lead me on; they never give me what I want," Mike growled down the phone.
"Oh don't worry Mike; we'll make it up to you this time honey; you will get everything you deserve," Doreen sweetly answered.
"See you at six then honey; bye." Doreen hung up the phone then commenced dialling Pamela and Steve.
Mike arrived at Doreen's establishment at 6:00pm sharp looking forward to his special deal.
Doreen met Mike at the door and escorted him directly to the basement dungeon room. Doreen had dressed up specifically for the evening and although nearly sixty she looked very sexy in a whorish way. She was wearing a tight black leather mini, a white silk long-sleeved blouse, black stockings and shiny black patent leather high heels. Underneath she was wearing red silk camiknickers over a red satin garter-belt and a matching bra was visible under her sheer blouse. She wore lashings of makeup and her blonde hair was piled high on her head. She looked exactly what she was; an old prostitute.
"I hope I'm getting something better than you Dor'; you look real sexy but fuck your old enough to be me mum," Mike whinged as they entered the dungeon.
"Oh don't worry Mike, you're going to get exactly what you deserve!" Doreen flicked back across her shoulder.
As Mike passed through the door he noticed another sexily dressed older prostitute sitting on the bed in the centre of the room. Then he recognised her! My god it was the whore he had raped in the alley; then he felt a little sting on his neck and then nothing but blackness. Mike awoke some time later but he didn't know where he was.
He looked around groggily and realised that he was still in the basement of the brothel but he knew something was seriously wrong. Something just wasn't right, he couldn't move for a start and his clothes just didn't feel right on his body. The he realised he was bound to a chair. Both his legs were bound to the legs of the chair and his wrists were bound to the arms. Positioned in front of him was a full-length mirror; he couldn't believe what he saw in it.
Reflected back at him was a plump, overly made up whore. Mike looked her up and down. She had a blonde bob, her eyes were heavily made up with mauve and blue eyeshadow; black eyeliner outlined her heavily mascaraed lashes. Her foundation and face powder had been thickly applied; her rouge was just as heavy and bright red lipstick completed her whore's painted face. She wore a large gold choker necklace and matching drop earrings.
Next he noticed her clothes. She wore a long-sleeved blouse of sheer nylon; he could see a black brassiere through the sheer material. The garment had ruffles at the front of the decolletage that came all the way up to her neck so that no cleavage was visible, although she had huge tits straining at the front of the blouse. Where the cuffs ended, her wrists were tied to the arms of the chair but he could see her red painted whore's fingernails.
She wore a red lycra miniskirt that just covered the very tops of her thighs; because she was lashed into the chair it bulged a little at the waist around her potbelly. Her legs were encased in sheer taupe stockings that glistened in the overhead light; on her feet were bright red high-heels. He could see her stocking tops where her skirt was hitched up around her thighs and he saw the silver glitter of her garter snaps at the end of the black suspenders that lead under the mini to the suspender belt. Her thighs were slightly opened and he glimpsed the gusset of a pair of black satin panties.
Each of her slim nyloned ankles was firmly bound to a leg of the chair in which she sat. Then it dawned on him; he was looking at himself!
Then he started to realise the strange feeling of the clothes on his body. The sheer hose on his legs were light and sexy; they felt like gossamer silk sheathing his legs. His cock and balls were encased in the softest of satin panties; they gently caressed his sex organs and the cheeks of his bottom. The skirt felt strange but sexy as the tight lycra spandex squeezed his potbelly and thighs. The blouse was made out of the sheerest of gauzy material that he had ever experienced and it lightly caressed his upper body. He could feel the bra underneath the blouse snug against him, a light padding material was obviously being used to fill out the bra cups to create the huge false tits.
He could also feel and taste the makeup on his face. The lipstick tasted sweet and slightly greasy but pleasant; just like it tasted when he kissed a woman. But the most disturbing thing, besides waking up to find himself dressed as a whore, was that he could feel his penis starting to harden in his panties. He wasn't sure if he aroused because he was attracted to the cuddly crossdressed whore he saw in the mirror (she was certainly dressed just the way he liked his women to dress) or because of the sweet caress of the lingerie and female clothing on his body.
But why was he dressed like a crossdressed whore; and more importantly why was he lashed into this chair? Both questions were about to be answered.
"Well don't you look pretty Mike," he heard a woman's voice coming from behind him; it was dripping with sarcasm.
Then Pamela stepped forward and came into his field of view. Although it had been a while, Mike recognised her immediately; it was the prostitute he had raped in the alley.
"What the fuck are you doing here. I fucked you once and you weren't up to much love; give up the game before your cunt falls into your arse!" he snapped at her contemptuously.
Whack! His head snapped to one side as she slapped him upside of his face. Then though teary eyes he saw Doreen walk in front him; she looked sexy. She had disposed of her miniskirt and blouse and was standing there in her red silk camiknickers, matching bra and a red satin garter-belt holding up her sheer black stockings; shiny black patent leather high heels completed the ensemble. Her heavy makeup had been touched up. Dressed only in her lingerie as she was, she looked quite dominating.
"Well fuck me Doreen, you don't look too shabby for a wrinkled old cunt!" Mike snapped again.
Whack! Whack! This time it was Doreen who slapped his face; she stumbled on her heels she hit him so hard.
Mike shook his head and this time took a good long look at Pamela; she looked very different tonight. She was wearing a black corset and waist cincher. It looked to be made of a satin material and although Pamela was plump it cinched in her waist, emphasising her large breasts and buttocks. Suspender straps ran from the garment down her plump thighs and were attached to black seamed nylon stockings. Her feet were shod in the highest of high heels he had ever seen. The ensemble was completed with bright red nylon panties.
Pamela had on her usual lashings of makeup, this time very dark and Goth like. Black eyeshadow, eyeliner, mascara, pale foundation and powder, but bright blush and bright red lipstick and matching fingernail polish. She wore a black wig and her hair was worn high almost like a beehive. She looked every bit the dominatrix.
"What the fuck do you old whores think you're doing! When I get out of this chair I'm going to slap you both until you bleed, then fuck you senseless, just like I did to you that night in the alley you silly old trollop!" he spat at Pamela.
Whack! This time the blow was so hard that the chair fell over with Mike strapped in it; it was no slap it was a full-blooded punch delivered into his right side.
Someone with great strength lifted Mike upright, still strapped in the chair. Now he was scared. Then Steve walked into view and he got really scared.
"What the fuck is this about? What's happened to me? Why am I dressed this way? Why am I tied to this chair?" Mike pleaded through the pain in his side where he had been punched.
"Well Michele," Steve began.
"NO! NO! Fucking NO! My name is Mike!" the crossdressed slut tied to the chair cried out.
"Well you see Michele," Steve went on as if Mike had not said a word, "I have decided to name you that because you remind me of a girl I knew in Chelmsford Prison. She wasn't really a girl of course but she was prettier than you and a lot better behaved once we tamed her."
"So I've named you Michele, and the girls here agree it's a good name; and of course they also agree that you need to be tamed. In fact this was their idea; mostly Pamela's, but then again you raped her you cold blooded cunt, it's only fair that she choose your punishment!" Steve went on.
"You can't! You can't!" Mike/Michele tried to go on but Steve shut him/her up with a 'bitch slap' across the face.
"Just shut the fuck up and listen. Your punishment has been designed to match your crimes."
"You continually complain that the girls get dressed up all sexy and then lead you on; that is, won't give in to your perverted whims, so you knock them around and abuse them."
"But most disgusting of all, you raped Pamela and left her on the ground in that cold dark alley. Now you are going to get the same treatment," Steve said matter of factly.
"Oh n…" Michele tried to interrupt and received another bitch slap.
"So we lured you here, drugged you as you walked into the dungeon for your 'freebie', shaved your legs, and turned you into a woman. Dor and Pam have done a miracle and turned Mike into Michele!"
"It took some doing, shaving, dressing and making you up while you were unconscious but the girls said it was pleasant work knowing what they were going to do to you eventually." Steve finished.
"Oh it was disgusting touching you after what you did to me," Pamela said, "but it will be worth it!"
"Now you look exactly like what you have always despised and abused; a fat old whore dressed up sexy and ready to work!"
"And now we are going to give you what you gave me; pain, humiliation and abuse! You can cry and scream all you like; this room is soundproof."
"We are going to rape you!" Pamela finished.
Mike realised now what had happened to him and how much trouble he was in. He started to whimper.
"Oh shut the fuck up Michele; shall I shut her up for you Pam?" Steve asked Pamela.
"Any way you like!" Pamela shot back.
Steve pushed the mirror out of the way and stood in front of Michele. He could see the tears in her eyes and her mascara starting to run down her pretty cheeks.
"Fuck you! You get the same sympathy you showed Pamela," Steve spat at her.
Steve unzipped his fly and extracted his semi hard member. Another 'Michele' in another time and place (a few years ago in Chelmsford Prison) had described his cock as monstrous the first time he hade her suck it, and the description was apt. It was only seven inches long but it had a massive girth and ended in a gnarled purple knob; thick red and blue veins stood out all along the length of the monstrosity.
Steve reached out and grabbed Michele's head in both of his strong hands. Michele looked up, she had a pleading look in her eyes but Steve would have none of it. He released one hand and placed it on his semi erect penis and began to rub it all over her face. Michele was horrified; the feeling of the slimy member being rubbed on her cheek, over her chin and even in her eye socket was sickening. She opened her mouth to protest and Steve took the opportunity and pushed his now erect cock over her lipsticked lips and into her mouth.
Pamela and Doreen looked at the man they had turned into Michele being abused and degraded by Steve. Doreen was not concerned that Steve enjoyed forcing himself on the crossdressed whore, he had told her of his adventures in Chelmsford; and besides they had a very kinky sex life and allowed each other to take multiple partners anyway.
Pamela and Doreen looked at each other and smiled; this bastard was getting exactly what he deserved; a dose of his own medicine.
"Stick it to her Steve," Pamela goaded Steve on as he forced his turgid member into Michele's unwilling mouth.
Steve smacked Michele across the face again drawing blood from a small cut inside her mouth.
"You take this bitch or else I will break your fucking jaw!" he swore.
Michele could only capitulate, she opened her lips and felt the hard spongy mass of Steve's cock enter her mouth. She tasted her own lipstick, the salty taste of her own blood and another slightly salty sweet taste that could only be Steve's pre-seminal fluid leaking from the eye of his cock. Michele gagged as Steve forced his cock into her painted mouth right up to the hilt, his balls resting on her powdered chin. He groaned.
"Take that you slut!"
Pamela now had her first taste of her revenge as she watched Steve's cock disappear fully inside Michele's mouth.
"Yeah, take that you fucking whore! How does it feel you dumb cunt! Take that cock you fucking rapist shit, I hope it fucking chokes you!" She spat at Michele.
As Pamela and Doreen started to savour their revenge, Michele felt utter humiliation. Steve began to fuck her mouth; his hard member pistoning in out of her lips as Steve held her head steady and stood between her splayed legs fucking her face. Michele felt the hard cock sliding between her lips, over her tongue and slamming into the back of her throat. 'My god, how do these girls willingly give head,' she thought as her mouth was raped and she gasped for breath.
Then Michele couldn't believe what happened next, she felt a hand caressing her nyloned thigh. The hand was stroking up and down from her knees to the very tops of her thigh and sometimes disappearing under her skirt and stroking her pantied crotch. It was Doreen! Michele looked down and saw the old hooker was kneeling beside her chair, Doreen's hand was under Michele's skirt stroking and rubbing the sleek material of her stockings and panties.
Michele found what happened next even harder to believe; she started to become aroused, her penis hardening in her panties. Steve continued to drive his cock in and out of her painted mouth and was quickening his pace. Michele felt Steve's penis become rock hard and start to throb; she knew what that meant, Steve was building to his orgasm. Oh Christ, she was about to get a mouthful of semen. But what the fuck was Doreen playing at?
Doreen had now lifted Michele's skirt and was rubbing Michele's penis through her silky satin panties. Michele had started to harden and Doreen grasped her penis and started to wank her. A small telltale wet spot appeared in Michele's panties; she was enjoying the forced masturbation even while Steve was raping her mouth.
Michele had now got used to Steve's member thrusting in and out of her mouth. Although she was not enjoying what Steve was doing to her, she had come to tolerate it. She couldn't understand how she could be so sexually aroused though. Doreen was stroking her hard cock through her panties and she was getting harder and responding to the luxurious stimulation of the satin panties being rubbed against her member. Michele actually started to buck in the chair thrusting her pelvis in time with Doreen's strokes. This also caused her head to bob up and down, inadvertently providing stimulation to Steve's hard cock in her mouth; he could also feel her tongue starting to work around his cock lashing at the sensitive underside of his penis.
Michele was now concentrating on the feeling of Doreen's ministrations to her sensitive penis. Doreen had now slid her hand inside Michele's panties and as the painted fingernails of one hand raked her scrotum through the satin panties, the other was wrapped tightly around Michele's shaft and was viciously wanking the hard member. She was half choking on Steve's penis and was working her tongue around it to try and squeeze more air into her lungs as Steve pulled back enough to let her breath.
Steve took Michele's bobbing and bucking as capitulation; her movements were certainly increasing his pleasure so he slowly released his grip on her head. Michele was now sucking in time with Doreen's wanking and she hadn't even realised it. She felt Steve's cock stiffen and convulse in her mouth and suddenly realised he was about to ejaculate.
'Oh my God,' Michele thought. 'This cunt is going to come in my mouth and I'm fucking encouraging him. What the fuck am I doing?'
Pamela was standing back watching the first part of her plan come together. Mike sat there dressed as Michele tied to the chair. Steve stood between her stockinged legs his thick cock sticking out of his jeans, Michele's lipsticked lips sucked on his cock as he thrust in and out of her mouth. Doreen kneeled to one side of the chair with her hands in Michele's lap. Michele's penis was sticking up proud out of the waistband of her black satin panties as Doreen wanked it furiously with one hand and stroked her scrotum through the panties with the other. Michele's miniskirt had been rucked up around her waist and as she bobbed and gagged on Steve's cock she looked just like the whores she had abused. Heavily made up, short skirt, stocking and high heels; sucking a cock just to get it over with; she had in fact become one of the whores she hated and used and abused.
Pamela smiled as Steve groaned; she knew what was coming.
Michele felt her own climax building; the frenetic wanking Doreen was giving her cock coupled with the strange but luscious sensation of the silky satin and nylon lingerie was just too much pleasure for her to bear; she needed release. At the same time she knew that Steve was about to ejaculate a disgusting mess in her mouth but there was nothing she could do about that; her orgasm had taken control of the situation and she felt it build and start to explode through her womanly body. Her cock-clitty started to spurt.
At the same time she heard Steve groan and felt his cock convulse in her mouth. Stream after stream of thick, ropy, semen filled her mouth. At the same time Steve grabbed the back of her head and pushed her face hard into his groin; she couldn't breath because he held her so hard against him and the flood of semen that filled her mouth. Michele started gag and retch on the semen flooding her mouth; she swallowed what she could but streams of the viscous fluid poured out of her nose because she couldn't swallow it fast enough. Also her own orgasm had just commenced and she started convulsing as the first jet of her own spend erupted from her penis; which was being wanked furiously by Doreen.
"Now!" screamed Pamela.
And Michele suddenly felt the most excruciating pain ever. As the first stream of ejaculate left Michele's clitty Doreen heard Pamela's cry and with her other hand she squeezed Michele's scrotum as hard as she could; at the same time she viciously twisted and squeezed her penis. Michele's orgasm came to an abrupt halt and she nearly passed out with the pain.
In the space of one second Michele had gone from the ecstasy of orgasm to the most cataclysmic pain she had ever experienced. Her cock and balls felt like they were on fire; the pain made her gag and she fought back the urge to vomit. She knew that would be fatal as Steve was still in the throes of his own orgasm and the last streams of his semen were shooting into her mouth. She tried to swallow the salty mess but her gag reflex was making her choke. Steve's sperm was flooding her sinus and running out of her nose making it impossible for her to breathe; she was sure she would die.
On the other hand Steve used Michele's choking and shuddering to increase the pleasure of his own orgasm; he pressed Michele's head harder into his crotch and as the last of his discharge pulsed out of him, he shuddered with the intensity of his orgasm. When he had finished he pulled his semi-hard member from Michele's mouth and rubbed his semen all over her face with his cock; her makeup mixed with his semen and her tears. She looked like a mess as she gasped for breath, choking and crying.
Pamela just smiled.
"So Mike, how does it feel to raped, you fucking prick!"
"Come on don't cry shit-head; you asked for it. I'll quote you if you like: ""You’re all the same you slags, dressed up in your sexy gear leading a guy on and then won’t do what he wants. Bitches! Fucking bitches! Now get over here and suck my cock!" "
"Isn't that one of your favourite rants; well now you know how it feels!"
"See Mike, or shall we say Michele, you asked for it. You just sat there all dressed up like a whore and in the end Steve had to take what he wanted. Sure, just like me you capitulated and tried to get Steve off; especially when Auntie Doreen started stroking you. But now you realise rape really is a violent act and there is no pleasure to be had by the person being raped!" Pamela finished.
"I'm so sorry," Mike/Michele shuddered, trying to breath deeply to combat the excruciating pain in her groin.
She was crying and gasping for breath. Tears streamed down her face, her mascara running and her lipstick smeared all over her face. The makeup was mixed in with Steve's spend and as she felt the sticky mess start to dry on her face she felt degraded and ashamed.
"I'm sorry; please let me go now. I've learned my lesson and I'll never abuse another woman I promise," Michele sobbed.
Pamela replied from across the room, her voice slowly getting louder as she approached Michele from behind.
"I don't think you have learned your lesson Mike. In fact I think you are far from it; but I'm going to take part in your final punishment personally; to make sure you know just how much I hate you"
"After all it's only fair that I get to do that; you raped me remember?"
"I'm the Bitch you left raped and broken on the filthy ground in that alley with her panties stuffed in her mouth; you remember? You told me; and again I quote: "Thanks for the fuck; keep the money bitch,""
"Well this Bitch bites back Mike! I spent the money you threw on the ground beside me to buy you a present in fact. Now open those come caked eyes and see what the Bitch bought for you!" Pamela exclaimed and walked around the to the front of Michele.
Michele looked up and horror filled her; she screamed…….."NNNNNOOOOOooooo!!!!!!"
"But Michele; I'm dressed just how you like your whores look!" Pamela teased.
What Michele saw when she opened her eyes was Pamela, still in her black corset and waist cincher; the suspender straps running from the garment down her plump thighs and attached to black seamed nylon stockings had now been adjusted slightly. The suspenders had been adjusted because protruding from the crotch of Pamela's bright red nylon panties was a huge black strap-on cock. Pamela rocked on her high heels and made the black rubber penis wobble inches from Michele's face.
"Remember what you did to me honey; well it's time for revenge; Steve, Auntie Dor, come and give Michele an attitude adjustment. You know what I mean; put her in an attitude that will allow me to use this on her," she smiled cruelly looking Michele right in the eyes.
Steve was standing to one side pushing his now flaccid cock back into his jeans. He zipped up and sauntered over.
"NO! NO! NO! NO! NO! NO! NO! NO! NO! NO! Pulleeeese don't" Michele begged and tried to tear herself free of the bonds holding her in the chair.
"Oh fuck this!" said Steve and punched Michele in the face, knocking her out.
Michele woke up to the stink of chemicals; then she realised that Steve was waving smelling salts under her nose. At first she couldn't figure out what was going on; in fact she thought she was still Mike having a bad dream. Then it all came flooding back as she started to feel the throbbing pain in her balls and the ache in her jaw from Steve's punch.
She realised now that she had been let out of the chair in which she had been bound but was now in worse trouble. She was locked in a set of stocks that Doreen kept in an alcove corner of her basement dungeon. Mirrors surrounded all three walls of the alcove, front and both sides, so she could she exactly what was going on. What she saw terrified her.
She still wore the long-sleeved sheer nylon blouse and the black brassiere was still visible through the gauzy material. Now where the cuffs of the blouse ended, her wrists were thrust through the holes in the extremities of the stocks, her red painted whore's fingernails stood out against the black wood of the contraption as she tried in vein to pull her hands through.
The red lycra miniskirt she wore just covered the very tops of her thighs. Her legs, encased in the sheer taupe stockings held up by the black suspenders, continued to glisten in the harsh overhead light; they were spread apart by a stainless steel spreader bar attached to her slim nyloned ankles and she could only just balance on her bright red high-heels. Michele realised she could hardly move at all. She could just swivel her head up and down and from side to side to look in the mirrors, her wrists and ankles were firmly secured. Then she realised something else; she was not wearing any underpants. Michele looked up and saw Doreen, who was positioned just to one side of Steve. Doreen was holding the black satin panties she had been wearing earlier and swinging them around her fingers.
She looked to the mirror in front of her and noticed her face had been cleaned and her makeup had been reapplied. The blonde bob was still in place, her eyes were heavily made up with mauve and blue eyeshadow; black eyeliner outlined her heavily mascaraed lashes. Her foundation and face powder had been thickly reapplied and with heavy rouge and bright red lipstick she was again the whore 'Michele'.
Then Michele remembered the last thing she had seen before Steve knocked her out; where was Pamela?
"Ok Pam, she's awake," Doreen called out.
"Well I guess it's time for the whore to pay her dues then; after all she's all dressed up and asking for it just like they all do; hey Michele?" Pamela teased as she approached from behind Michele. Michele looked in the mirror and saw Pamela approaching from the rear.
Michele saw the huge black rubber cock attached to Pamela and began to cry; she realised how vulnerable she was locked into the stocks with the spreader bar holding her feet far apart.
"Please, please don’t," Michele pleaded, knowing she was in deep trouble.
"Yeah, that’s it bitch; you say please! You say please and I might be nice, don’t worry Pamela knows what you need," she growled.
"Sound familiar Michele? We are saying to each other the same words that we said to each other on that night you raped me in the alley; except this time our roles are reversed!"
"Ok Doreen; gag the cunt!" Pamela ordered.
Doreen stepped forward and shoved Michele's black satin panties in her mouth. As she tried to spit them out Doreen pushed them in further until Michele was effectively gagged.
"Now," Pamela whispered into Michele's ear, "the Bitch bites back!"
Steve and Doreen both sat down on a couple of chairs that Steve had dragged over and began to watch the show.
"As I said to Pam; revenge is a dish best served cold, and we have certainly planned this to perfection," Doreen whispered into Steve's ear and gave his muscular thigh a squeeze.
Michele watched in fear as Pamela clicked across the floor on her high heels and positioned herself behind her. She couldn't see much, other than Pamela moving in directly between her spread legs. Then she felt her miniskirt being lifted up and felt a cold wet substance being squirted between the cheeks of her arse. She just had time to realise that Pamela had lubricated her arsehole when she felt the hard rubber cock intrude inside her sphincter.
Michele wanted to scream with pain but the panties stuffed in her mouth prevented her from doing so. She heard Pamela grunt and heard the click of her heels as she rose up and down on the balls of her feet as she began to force the cold hard weapon deep in her arse. She thought the squeezing Doreen had given her balls had been the worst pain she had ever felt but this was far worse.
"Give it to the whore!" Steve goaded.
"Fuck that cock hungry slut!" Doreen provoked Pamela to push harder.
"OHHGGGHH!!!" Pamela grunted as she forced her groin forward and pushed the rubber strap-on dildo as far as she could up Michele's arse. Then she reached down and flicked a switch on the base of the strap-on and it began to fiercely vibrate.
Michele felt her insides tear as the huge intrusive dildo ravaged her back passage. She wanted to scream but her panty gag prevented her from crying out. She started to cry again in pain and humiliation; her makeup running in rivulets downs her cheeks. It was bad enough that she was being raped; but to have Steve and Doreen watch and gloat was so degrading.
"Oh look Pam; she's doing the panda thing again!" Doreen exclaimed, "After all the trouble I that went too to fix up her makeup; the inconsiderate bitch!"
"Does it hurt your 'botty' Michele?" Steve laughed solicitously, "Don't you like a hard cock in your arse as much as you liked my cock in your mouth?"
Michele jerked and convulsed as she felt Pamela flick the switch that made the dildo vibrate in her behind. The pain was now almost unbearable and she thought she would pass out. Her back passage felt swollen and she knew that something in there was torn. When she thought it couldn't get any worse Pamela began to violently fuck her arse.
Pamela pounded the big black vibrating strap on dildo in and out of Michele's arse. The vibrating phallus pressing into Pamela's crotch through her nylon panties started to arouse her. She settled into a steady rhythm and concentrated on bringing herself off. She thrust in and out as hard as she could, both to punish Michele and to increase her own pleasure. Pamela started to spit obscenities at Michele.
"Yes Michele; take it honey; you know you need it," Pamela snarled into Michele’s ear.
"Come on honey you need it don't you? Well let’s see how bad you need it baby!"
"Remember those words you cunt; you said them to me while you raped me!
"You need it do you whore? Well here it is!" Pamela exclaimed and began to frantically rape Michele.
The thrusting and vibrating rubber cock was quickly bringing Pamela to orgasm. She had not expected this but she thought it only appropriate that as Mike had come when he raped her; she should come while she raped him.
Michele was now in agony as the hard rubber cock continued to violate her bowels; a slight pleasant tingle had started to grow in her prostate but the pain she felt overrode any pleasure she may be getting tenfold. She squirmed round and tried to move her arse away from her rapist but she couldn't move. All she could do was move her head and as she looked up into the mirror what she saw repulsed her.
Michele was standing spreadeagled tottering on her high heels, her long sleek stockinged legs forced apart by the spreader bar and her skirt was rucked up. Positioned between her sexy legs was a heavily made up chubby Goth vixen dressed in black lingerie, her sleek black seamed stockinged legs bent slightly as she balanced on her heels and fucked a hard black rubber cock in and out of her soft white arse. She was cursing and groaning.
"Take this you fucking bitch! I'm raping you back you cunt! I'm fucking your skag arse you whore!"
"And I'm commmmmmmming!!!!!!!!!!!"
Steve had been watching Pamela rape Michele and of course the inevitable happened; he became aroused and erect. He opened his fly and freed his hard chubby member and took Doreen's painted fingernailed hand and placed it around the turgid tool. Doreen began to absent-mindedly stroke Steve's cock; she was intrigued by what was happening before her eyes.
"My fucking god Steve, Pamela's actually enjoying raping that poor cunt!" she gasped.
"And I'm enjoying watching her too," Steve smiled as he hatched his own little plan in his head.
Then he saw Pamela begin to thrust in and out of Michele as hard and fast as she could and heard the obscenities she was screaming at Michele and he knew she was about to come. He made his own move and jumped out of his chair and moved it in front of Michele where she was locked in the stocks. He jumped up on the chair, his hard cock jiggling in the air as he held on to the stocks with one hand to keep his balance. Then with his other hand he began to furiously wank his cock in front of Michele's face. He looked down at her.
Michele was now silently sobbing; tears streamed down her cheeks as she weeped muffled cries into the satin panty gag that had been thrust in her mouth. She looked up and tried to implore Steve with her eyes but all she saw was his cock inches from her face as he stroked it and groaned with pleasure. His eyes were locked on hers but they displayed no pity, only lust. Michele's back passage was on fire; she could tell by the increased tempo of the ruthless fucking and by Pamela's grunts and groans that she was about to come. She just wished she would hurry before she exploded in pain. The monster cock was ravaging her insides and the crude vibrations only amplified the pain.
Then Michele felt Pamela drive the intrusive monster right up her, as far as it would go and push for all she was worth. Pamela was coming. Michele grunted in pain into the gag and screwed up her eyes. Then she felt the hot ropes of Steve's semen as he ejaculated in her face. She made the mistake of opening her eyes in surprise and a spurt of warm salty semen flew across her face and into her eyes. It stuck to her face and then dribbled down from her eyelashes and some of the viscous fluid went into her right eye and started to burn. Steve was moaning in ecstasy.
"Take that you fucking rapist whore! Take my spunk you fucking cowardly crossdressed hag!" Steve cried as came.
Pamela was pushing her groin into Michele's buttocks as hard as she could. The vibrating phallus was sending waves of pleasure through her pantied crotch as she pushed hard against Michele's arse to force the base of the vibrating rubber cock against her clitoris. She spasmed and bucked as her orgasm consumed her. Her stockinged legs rubbed against Michele's nyloned thighs, adding to the gathering circles of pleasure that raced up and down her body as she climaxed.
Her orgasm slowly subsided and she fell forward so that she was resting against Michele's imprisoned body. When she gained control of herself she pulled back viciously ripping the still vibrating cock from Michele's arse. A flood of lubricant, blood and other matter began to run down Michele's thigh and stain the top of her stocking. Pamela moved around to the front of Michele, the obscene strap-on phallus still pushed out in front of her like a lewd putrid figurehead.
Steve stepped down off the chair and pushed it back; his tumescent member hung out of his fly, the last drops of semen dripping from the gnarled knob.
Michele opened her one good eye, tears makeup and semen streamed down her face, the other remained closed due to Steve's semen still stinging her there. She was sobbing into the panty gag and obviously in tremendous pain. Pamela moved in and stood beside Steve.
"Was that good for you too bitch?" she asked sarcastically and ripped Michele's panties from her mouth.
Michele sobbed and moaned.
"Please………….no more!" she begged.
"Oh shut the fuck up!" Pamela spat back mercilessly. She took the black satin panties and wiped the last drops of semen from Steve's cock, cleaned the fetid mess of lubricant, blood and faecal matter from the strap on cock still attached to her crotch, and shoved the panties back into Michele's mouth.
She turned around to her Auntie Doreen and said,
"I think I've finished with this bitch for now!"
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The End