Cynthia’s Sissies
A Fictional Story by Wankerino.
Miss Cynthia Remington reclined in her tall red leather-clad throne. She was a pimp… among other things… and ran a highly immoral prostitution ring… and it paid her very well…
Sex sells. It was the way of the world… and her Master understood it better than anyone…
She was 45 but looked like she was in her early 20s. She was tall, slim, and white with long blonde hair and piercing green eyes.
Her angular face would have been beautiful if not for her blacked soul and sociopathic lust for power and money…
This morning, she wore a long, silky black nightgown with shoestring shoulder straps to go over her wide shoulders and reclined in her office as she skimmed her Return-on-investment data.
Her breasts hung heavily on her chest as large as watermelons… she really couldn’t resist showing them off… not after the price she’d paid to acquire them…
She sipped her drink from a crystal goblet and felt relaxation and a sense of liberation flow through her… Her peace was suddenly disturbed by muffled male moaning coming from her bedroom down the hall…
Anger flared in her briefly… disturbing her communion with her Master in the supposed seclusion of her mansion estate was extremely irritating…
She had intentionally left the Police Commissioner tied down and gagged since she had tired of him last night… He wouldn’t be making any further inquiries when she was done with him…
Cynthia was 6ft 3 and rather well muscled, without losing her feminine nature. No man (or woman) could stand before her and not feel bizarre compulsions born of desire.
She owned over 200 prostitutes that were little more than slaves leashed to her will by fear and lust. Most of them had been men… but not when she was done with them…
Her associates had concocted a DNA-altering, hormone-deregulating substance which behaved very much like a virus…
It was ideally applied to the skin or directly into the bloodstream as a different compound, after which it would begin to affect the tissues it contacted… This was known as Stage 1.
During stage 1, DNA instructions would be altered, and the body would begin producing ‘different’ cell formations which were comparable with female development… but usually more extreme…
Needless to say, testosterone levels would deplete to almost nothing, and estrogen would skyrocket…
The subject/victim would find it impossible to maintain serious muscle mass, and breast tissue would grow where pectoral muscles had once been…
Testicles would shrink to a very small size, the prostate would become as big as a baseball, and the penis would never be able to get hard…
The fibers in the penis would never be properly engorged with blood. So the penis would atrophy – occasionally getting hard for very brief moments before orgasm – but even this would cease as the years rolled on…
Then came Stage 2. As the pseudo-virus continued to spread, it would eventually enter the bloodstream and begin affecting the entire body… including the bones and the brain.
Bone structure would become noticeably feminine, and the victim’s IQ would decrease significantly…
At this point, they would be only obsessed with orgasming, sex, simple rewards, and thoughts of punishment… they would be reduced to the state of an animal incapable of higher-level thinking… pitifully easy to control…the perfect slave….
———
The cold winter night air bit hungrily into Jemima’s exposed ankles… It was Friday night, and she was standing on the street corner, as had been the case for her these past months…
The salty taste of cum still lingered in her quietly chattering mouth… She was dressed in black high heels, a pink rubber miniskirt, and a Pink bra to hold her heavy breasts.
Over everything, she wore a knee-length white fur coat of exotic snow tiger. She had received it years ago from her mistress pimp in return for her snitching on a conspiracy of rebellious sluts…
She made a habit of wearing her black panties as well, to hide her shamefully small willy and virtually non-existent ballsack…. just in case she had to bend over…
She would prefer people think her only a stupid slut, than a broken sissy…
After all these years, it still made her heart quiver in sadness to look down at her crotch and see nothing more than a small pink mushroom head over a wrinkled testicle-less scrotum…
It was cold, and she had already serviced 5 clients tonight… she wanted to call her pimp and go home… but she knew other girls who had refused to continue working… They had never been heard from again…
Fear gripped Jemima’s beating heart, and she put the phone back into her purse… The phone slid amongst other items in her purse.
There was an assortment of specially-treated candy, a fake pistol, specially concocted perfume, disinfectant, and a tube of the special cream that her pimp had ordered her to apply to her lips or anus whenever servicing a client…
The cream was greasy and intoxicatingly aromatic, and very hard to wash off…
Suddenly, she was blinded by the headlights from an oncoming car. It illuminated her long, blonde-dyed hair and makeup-strewn face… Her big blue eyes glittered in the sudden light, and her big red-lipstick-slathered lips must have looked almost comical… she looked more feminine than a normal woman…
She must have looked quite the catch – she thought to herself…
She peeked through her dainty fingers and saw that the oncoming car was a familiar client… she sighed in relief…
He was just some loser from around town… He had half-heartedly fucked her once… but now just turned up for blowjobs…
The lime-green pickup truck slowed to a halt next to Jemima. She smiled seductively at the man in the driver’s seat…
“Hiii there baby…. do you want the Usual? Or can I do something special for you this fine evening?”
“… Umm yeh… just the usual…” he replied lamely, in a voice that sounded more than a little girly. Jemima smiled at his neutered voice… He was definitely in Stage 1…
She opened the heavy car door and tried to climb in. She was very physically weak, and her breasts only made it harder. The client reached out and grabbed her hand, pulling her in. She gratefully let him help her.
“Such a gentleman… but you’re not gentle… are you? hehe,” Jemima remarked as she closed the door and accepted the money from the blushing customer.
He was obviously a simpleton loser, even without the effects of the cream. He sat silently in the car, a small tent in his pants, as he drove slowly.
Jemima pulled out her phone to text her pimp about the current situation. As she looked at her phone, she tried to make conversation.
“…Soo… you like live around here or something?…”
“… yehh… just 10 minutes down the road… I mean… um…on the other side of town… out of town…”
Jemima smiled to herself. He really was Such a loser.
“… so I could just visit you? It would be so much more convenient, right?”
“Yeh… I mean no…I live out of town…”
Jemima looked up at him, seeing him cring in shame.
“Sure, baby… whatever you say… we can pull in here, baby.” Jemima pointed to a nearby alley.
As the client pulled in, he glanced nervously at Jemima’s phone.
“… look… can you not film me this time please?” He asked pathetically
“… sorry babe, but rules are rules… My people need to know where I am and that I’m safe…”
“… yeh… ok… sorry…” he replied lamely.
“We need the lights on, baby… I need to see when I’m working…” Jemima whispered as she set the camera up on the dashboard. She angled it to get a full view of the client’s face and crotch.
Jemima applied a thick layer of cream to her hand and lips as the client pulled down his pants to his ankles… She stared mutely at his dick for a moment.
He was definitely smaller than when she had first seen him… His little pecker used to be 6 inches, but now stood at a shriveled 4 inches…
“..are you still limp baby?… Oh haha that’s actually how big it gets?”
“… oh shit… this is embarrassing…”
“… haha… wow… (She flicked his dick with a finger and stroked his entire crotch with a greasy hand)… that’s got to be one of the smallest dicks I’ve seen for a while”
He leaned back in his seat waiting for her to go down on him. She reached under his shirt and smeared the remaining cream over his chest,
“… what are you doing?” He asked
“…I’m trying to get you hard…”
“… I am hard…I..”
“No honey… If that’s hard, then that’s a sissy dick… do you have a sissy dick?…”
“…. fuck… I’m gonna cum…”
“… you’re cumming from me calling you a sissy?… haha You are such a loser… I hope you don’t cry like last time…”
“…yes miss.. I’m a loser…a sissy loser… please suck my little willy…” He whispered with tears in his eyes.
“Good boy…” Jemima smiled at his submission. This was so much faster than sucking them for 10 minutes…
She lowered her mouth to his quivering dicklet and took it in her mouth…. She slurped for 20 seconds when the warm taste of semen filled her mouth… She compulsively swallowed it and leaned back to breathe deeply as he predictable began crying…
Jemima looked down at his dick… he was still hard…
“Oh wow… You got reserves, do you, sissy?” She smirked as she applied cream to her hand
“… ooof…uh… please don’t call me that…”
She ignored him and reached forward to start jerking him again…. 1 minute later, a thick rope of cum shot out. She aimed it at his face… it splashed him in the eyes as he cried from the emotion of cumming so hard.
“If you’re not a sissy loser, then why is there cum on your face?… haha…”
“..ss..sorry…”
“…. welll ok baby.. I’m leaving now… but if you want to dribble… come see me again…”
“… (sob)… yes baby… thanks…”
“… Don’t be cheeky… I’m not your baby… You pay me to make your little dick dribble… don’t call me Baby ever again… ” Jemima bitchily chastized him. She felt like slapping him, but didn’t want to risk retaliation… he still had balls ‘technically’…
“…I-I-I didn’t mean it like that…. I just like you…”
She smiled at him briefly and watched him lower his gaze.
“…Oh, you’re a sweety… see me tomorrow…”
Jemima smiled to herself. That had gone excellently. He was ready for sissification, and her mistress would reward her for her work… She reached for her phone and turned the camera off before stepping back out into the cold night air again…
“… bye beautiful…” he mumbled as she walked away.
The night was not over, and she would be seeing other clients. Tomorrow night, she would definitely be seeing that sorry loser again… but he would find a real woman waiting for him…
Her mistress pimp always liked to meet her victims in person before they became completely corrupted…
Jemima’s miniskirt hitched high over her big bum, and her fur coat blew in the chill wind. With a shocked gasp, she realized the tattoo on her bum would be visible.
The tattoo was an inverted pentagram. It was the tattoo of ownership her pimp employed… In the middle of the pentagram was a bar code, and deep in the flesh was a tracking device…
Jemima was too much of a bimbo airhead to understand who her employer really worked for… but she understood that showing that symbol to people could be offensive…
She walked off back into the night, hoping that her next customer could fuck her hard… She only came properly when she got fucked… and she needed to cum at least once a day, or she would begin to get withdrawal symptoms.
*****
Part 2…
Cynthia Remington’s fat pussy tingled from her recent orgasm… Most of her thick, creamy ejaculate still lay spattered on the police commissioner’s bruised face as he slowly came to his senses on the bed…
She barely had to try to break him… She supposed his wife had already broken him… or maybe he was just inherently a weak, pathetic man… She came across as the effeminate, credit-stealing, bureaucratic type…
He looked so respectable in his uniform… but naked on the bed with his noodle arms, beer belly, man boobs and receding double chin – he was simply a loser… Cynthia felt disgusted with herself for letting his body even touch hers…
If she weren’t a savvy tactical sort, she would have given in to her psychopathic desire to dispose of him simply… nonetheless – she needed him… for now…
Cynthia’s sleek, muscular body elegantly rolled off the bed … and walked over to the wardrobe…
It was a majestic piece of carpentry, carved from a solid piece of wood… the world’s largest and oldest tree was no more… 80% of it turned into wood shavings… and the remainder was a 16-ft-square masterpiece of faux Edwardian carpentry…
The sheer wastefulness of it always warmed her heart… She reached inside and drew out a long dressing gown of fine gold-laced velvet…
As she tied the robe belt around her tight muscular belly, she was thinking of having him clean her ass… but she didn’t want his piggy tongue touching her anymore…
She glanced back at his spread-eagled body… He was awake now and lamely pulling on his cuffs… He even dared to look her straight in the eye… It was a shame that men tended to stop being submissive after they’d dribbled their load… and this loser had cum twice…
His flaccid 2-inch dick was coated in its own watery jizz… He had actually cum just from her raping his face with her pussy…
“… can I… can you let me out?” He asked lamely. She sighed and felt the first embers of anger flare in her heart.
“Let you out? Why?… you seem to like being tied up…” She bitchily remarked
“(gulp)… I do… if you uncuff me… I can … fuck you?” he insolently mumbled.
Cynthia’s anger exploded before she could control it. She strode onto the bed as fast as a storm wind and had a foot on his chest… She applied too much pressure accidentally… She felt a sudden giving way under her toned leg and knew that she had broken at least 1 of his ribs…
He blurted out in pain as her foot pressed into his fleshy chest… She felt an intense rush of satisfaction at his pained cry… such genuine pain was music to her ears… She sorely wanted to continue – but common sense stopped her…
“… I’m… sorr…sorry…” he gasped
“… you really are pathetic… aren’t you?”
“… yes miss… (gasp)…i’m a joke… even my wife hates me…” he struggled to say. Cynthia’s anger died down slightly… such ‘voluntary’ self-deprecation was even more pleasurable than physical pain…
A flicker of a humorless smile crossed her beautiful angular face… Her piercing emerald-green eyes pierced his… He refused to look at her face out of fear… but looked up her leg at her beautiful hairy pussy mound and her heavy cleavage now revealed slightly by her partly open dressing gown… A drop of pussy juice dripped from her cunt and landed onto his chest…
“… yes, you are a joke … a fat little loser… with a small dick…don’t you have a small dick?”
“…yes Miss Cynthia… my willy is a joke…my wife laughs at it sometimes”
Cynthia smiled and removed her foot… She straightened her gown so he couldn’t see her tits anymore and stepped to the base of the huge sex bed…
“… I’m sure lots of people laugh at it… Your balls are small too… did you know that?”
“… what?…”
“… you have Small Balls… they’re as small as ping pong balls…” Cynthia declared as she cupped his ball sack under the toes of her left foot. It barely spread over the middle 3 toes of her foot and was slightly purple from when she had crushed them in her hand minutes ago…
“… yes… they are a bit small, I suppose…” He huskily muttered… his erection was coming back slowly…
“… small balls mean weak sperm… has your wife ever gotten pregnant?” Cynthia asked, as she flicked them with her toes onto his chubby thigh
“… no…” he muttered with pain in his voice.
“… and she definitely won’t be getting pregnant after I’m done with you…” Cynthia whispered as she kicked his left nut with ferocity that one would kick a rat scampering along the kitchen floor…
The police commissioner didn’t say anything… His whole body tensed, and tears began to form in his eyes… His left testicle was slightly ‘out of position’ and had a purple bruise on it…
Cynthia smiled with delight… she longed to crush the other ball and hear him cry like a girl… but she needed him to have his other testicle… lest she lose any leverage over him… he sobbed quietly as she pressed her foot over his little 5-inch willy… Interestingly, he had not lost his erection… In fact, he looked harder than before…
“… I know where you live, commissioner… I know everything about you… Look me in the eye sissy!” She burst out. At the word ‘sissy’, his eyes reluctantly focused on her intensely beautiful face…
She was still robed to hide her magnificent breasts and pussy… all he saw was a giant woman with piercing green eyes and lustrous ebony hair – one foot crushing his dick against his pubic bone ….
“… Stacy is taking the case… if you don’t go along with Everything she says-” Cynthia slowly moved her foot over to his remaining testicle and began putting her body weight down…
“NO.YES YES YES .. FUCK. I WILL DO WHATEVER YOU WANT…. ANYTHING… just please don’t hurt me anymore…” He cried out
“Good sissy… and when you behave… ” She opened her gown to reveal her watermelon-sized breasts. The nipples were at least an inch long… She moved her foot to his dick again…
“…when you’ve done your part… we can fuck… as Hard.. and for as Long as you like… and as often as you like…” She said as she jerked her foot back and forth over his 5-inch dick…
“…mmm… yes… anything … Anything… You owe me…” he muttered painfully. Cynthia smiled evilly at him and removed her foot. He had been on the verge of climax… she really enjoyed inflicting that sort of pain…
“Good…” She walked off the bed and strode out of the room… She wanted nothing more than to have a shower… her ‘assistants’ would help the commissioner in due time…
——–
Jemima desperately pawed through her sparkly purse… the money was gone!… he had robbed her… tears born of terror began gripping her heart… she had earned over 2 grand last night… and now it was gone!… she contemplated just Running Away… but Miss Cynthia’s officers would find her fast… The tracker in her butt cheek could not be easily removed…, and besides, they would find her anyway…
Tears ran down her face as morning traffic started rolling past her…what a joke she must look like – her fine fur coat was encrusted with mud, and her clothes were completely soiled… her bleeding nose really made her look like the tramp she was…
With a trembling hand she opened her phone…
“… hii… yeh it’s me… something’s happened…. ”
——
A rubber-gloved hand knocked on the expensive oak door.
“Come in, Penelope!” Cynthia called out loudly from the other side of the door…
Penelope stood in the hallway… She cleared her throat and hurriedly checked the mirror to her left… She saw a flat-chested ‘woman’ with short, thinning blonde hair. She wore overalls with big rubber boots. .. She looked like a balding effeminate male farm worker to the untrained eye… She was 30 but looked like she was aging well, though she was into her 60s….
Penelope forced herself to breathe as she slowly opened the door into Miss Cynthia’s office… She was sitting upright at her desk, typing at her laptop. She was dressed in a long black shoulderless dress with a pair of black boots over black fishnets…
She didn’t look up from her computer as she typed away…
“…You’re late, Penelope… My massage session was due 1 hour ago…”
“… I had to … deal with one of the girls…we had a call this morning… she didn’t call in last night… and this morning she claims she was robbed…”
“… punish her then in accordance with how much she owes”
“… I was going to… but she claims she can get us another girl…so if I punish her, it could negatively affect business growth… I wanted to bring the matter before you…”
Cynthia stopped typing and put her laptop off to the side… her emerald gaze fell heavily on Penelope like a guillotine of judgment. Penelope could barely contemplate lying… And she became acutely aware of how feminine and beautiful her Mistress was … in comparison to herself…
“Well… what are the details?” Cynthia asked as she leaned back in her chair
“Male… early 20s… no meaningful friends or family relationships… poor… but clearly loves the services of your workers so much that he will pay the price repeatedly… the ‘medication’ has been applied to him at least 10 times in less than 2 months…he’s deeply into Stage 1 development… we have plenty of footage of him being… serviced … the footage speaks for itself… he seems to be ripe for the plucking… and he has agreed to meet your girl tomorrow evening… I thought you’d like to know… ” Penelope stated matter-of-factly with a knowing look…
Cynthia smiled wryly… as she pushed her chair back.
“… you do do a good job of looking after the girls, don’t you… Penelope… I imagine you must have made quite a good mother…” Cynthia said as she turned to get up
“…actually… I was a mother…” she muttered, with a little pain in her voice as she walked to the corner of the room to retrieve the massage table. Cynthia looked at her with a hint of suspicion.
“You came here after school… you were going to study economics at university?”
Penelope stopped as she was about to lift the table and looked at her Mistress in surprise.
“..No miss.. I worked as a school teacher for 5 years… until your people found me and… showed me how… successful… I could be …if I did what they said…” Penelope muttered as she took off her rubber gloves, revealing a solid-gold watch on her left wrist…
Cynthia noted her slightly remorseful tone… and considered the potential for defection.
“Oh, of course… I mistook you for one of my former assistants… after the medication and the … celebratory rituals… you all tend to look the same to me… Any children?” Cynthia said in an almost friendly manner as she started undressing…
“… 2…. but then my husband saw your girls… eventually he couldn’t … pleasure me… he … or she…works here now” Penelope muttered as she looked down at her own feet – not failing to notice her non-existent breasts… She was acutely aware that Miss Cynthia had had many assistants… she didn’t dare inquire about their whereabouts.
“… You’re richer and more powerful than any school teacher, Penelope… never be ungrateful for the Opportunity i’ve given you… and never forget that you work For Me,” Cynthia declared as she gestured for Penelope to bring the table and towels forth…
The table was an ergonomic padded bench with a pair of Stainless-steel U-shapes attached in front. On either side of the bench were armrests…
As Penelope brought the strange apparatus forward, she felt herself getting slightly wet as her Mistress undid the loops of her dress to reveal her monstrous FF breasts…
Cynthia’s long black hair framed them almost perfectly as she sat down on the bench and looked expectantly at Penelope…
“…aren’t you happy you don’t have breasts anymore, my faithful Dyke-bitch Penelope…. and lay the plastic matting down… these rugs are a devil to clean…”
“… yes mistress…” Penelope mumbled. She knew what was going to happen… Cynthia often liked to bully her underlings… and Penelope liked … and needed… to be bullied… It was humiliating… and necessary…
“… I’m sure you love being Ugly and old, don’t you… flat-chested with thinning hair … soon you’ll be bald… just wait until our next celebration event… won’t that be nice … to be Liberated from the unfair expectations of womanhood?”
“…yes mistress… can … can I show you my … my shame…?…” Penelope mumbled… She was extremely wet now… her thighs were practically drenched as she had urinated herself.
“…yes bitch… you may…” Cynthia said with a growing smile as she watched Penelope undress…
Penelope started with her work boots. She placed them next to the wall. Then she took off her rubber overalls…. She placed them next to her boots… then she started undoing her leather belt…
Up until now, anyone would have assumed she was just a guy with hormonal problems… She was now dressed in tattered trousers and a long-sleeved blue shirt… the only nice thing she had was a gold watch she wore on her right wrist… and quite frankly… it was a Man’s watch….
She shuddered as she unbuttoned her T-shirt… She looked down her boobless chest and saw her little beer belly and a pair of long nipples protruding from her relatively muscly pectoral muscles…
She remembered when she had quite normal-sized breasts…. she wondered what it would be like to have proper breasts again… that could have fed children… that could have made her feel like a woman…and made men actually like her…
She then looked at Miss Cynthia’s breasts… They were almost as big as Penelope’s own upper body… the soft curve of them was intoxicating… They were Perfect… Penelope felt another gush of fluid come from her crotch…
She hesitantly looked down at her drenched trousers before continuing to undress… slipping her arms from the sleeves of the shirt, she threw it with the rest of her clothes… Finally, she undid her trousers.
They were sticky against her ankles due to her excessive vaginal discharge… she took them off and threw them gracelessly with the rest of her clothes… Now she was only dressed in socks… and her rich man’s watch…
“…mmm show me your crotch Penelope…” Cynthia ordered, leaning back in amusement…
Penelope’s face turned an extra shade of red as she took her hands away from her crotch to reveal her freakish pussy… It was lipless… wrinkly…fleshless… rimmed with a rug-like layer of hair…and gaping with a pair of flappy wings going down her soaking ankles…
She could have taken half a baseball bat in her Disgusting Pussy without noticing….and her clit was basically non-existent… Getting off like a functional female had become impossible for Penelope…
“Welll… it’s no wonder your husband wouldn’t fuck you…” Cynthia quipped as she slowly fingered herself… Penelope could barely understand how her Mistress could get off to her broken pussy and her titless chest… but Penelope needed the humiliation… it was the only way she could cum…
The ‘woman’ came out of her day-dreaming and stepped forward to grab each magnificent breast with 2 hands… She carefully placed the left one in the left cup… and then the right… They were so heavy… her Mistress’s back muscles must have been very strong to carry them around all day… As the last breast slotted into place, Cynthia sighed with relief.
“… milk me…” Cynthia whispered as she rested her hands on the armrests and closed her eyes. Her long black hair fell around her breasts like exotic ebony silken drapes… framing her breathtaking face and goddess-like breasts…
Penelope wasted no time as she pulled out 2 large aluminum buckets and placed each one under each heavy tit…
Starting at the top of the cleavage, she forcefully pressed all the pressure points to dilate the vessels that transported milk to the nipple… After stimulating these pressure points, she would massage the entire breast in a downwards motion…
Her mistress forbade the use of milking machines, strings or ropes… she preferred the ‘massage experience’ even if it took longer…. When the milk build up was sufficient, she would lower her salivating mouth to the nipple and suck…
Eventually the thick, creamy, pungent milk of her Mistress would fill her mouth up faster than she could swallow… The remainder of the milk she would squeeze into the buckets… When the milk flow slowed… she would start again…
Her big strong hands artfully caressed each breast… first the left… then the right… she had always found that allowing a break for each breast ensured the next load of milk was as efficient as possible…
A beautifully subtle and intricate network of pulsing blue veins showed in her Mistress’s boobs when she was lactating… massaging the breast tissue around the veins always seemed to please Cynthia the most… She groaned as the pressure in her breasts was relieved by the quivering hands and mouth of her assistant…
Needless to say… Penelope was incredibly aroused during the whole process… The humiliation of servicing such Magnificent breasts pleased Penelope excessively, considering that she had lost her own breasts on account of becoming the freakish broken titless female that she was now…
The buckets were almost full now… It was hard to believe that Cynthia’s breasts had actually increased slightly in size over the months that Penelope had worked as her ‘assistant’…
“mmm… suck me, Penelope…. The sissies will have enough milk, I think… mmmm,” Cynthia moaned as she lovingly drew Penelope’s head into her bosom… Penelope’s mouth sucked and swallowed eagerly for what must have been half an hour as she pathetically humped her crotch in rhythmic motions like she was riding a willing male slave… She was so close to cumming…. She looked up at her mistress’s relaxed face…
“… (suck slurp)… Miss.. (slurp)… Cynthia…(suck)… can I … (suck slurp)… cum now? (slurp)”
Cynthia lazily opened her eyes to see the small pool of liquid between Penelope’s ankles, where Penelope was kneeling… With a lazy kick of her right leg, she kicked Penelope in the crotch…
“What are you, Penelope?” She asked as Penelope slurped away
“…(suck)…I’m (suck, slurp)… a pathetic (suck) loser (slurp)…”
“…mmm … yes you are…” Cynthia smiled at her desperate subject’s admission. She kicked her in the crotch again… but Harder… and then again Harder… Harder…HARDER… The third kick caused Penelope’s bum to rise into the air with a deliciously Meaty Slap, which elicited a muffled grunt from her…
Her little beer belly jiggled from the blow… She gasped as she stopped slurping down milk and moaned in what could be described as a genuinely feminine quavering orgasmic cry… Penelope ground hard against her mistress’ ankle; she came as hard as a water fountain…
To Cynthia, it felt like she was trying to block a water jet in a spa… It really was amazing how much such an ugly woman could cum…
Cynthia checked her watch as her pathetic assistant diddled her gaping pussy and sucked away the last drops of milk… The pressure from her breasts was receding… she didn’t feel so irritated now… but she was still horny…
She was used to having her ass licked at least once per day… that pig of a police commissioner could keep his tongue to himself… she preferred the mouth of a woman… even if she looked like a man.
“Enough, Penelope…” she said as she reached back toward the desk to grab her phone… Penelope either didn’t hear her or ignored her as she kept sucking away at her tits…
“ENOUGH… ” Cynthia repeated…. She was surprised that her assistant was not responding.
She reached forward and grabbed her by her thinning hair… She pulled her head back excessively hard and pulled out a handful of hair…
“I said ENOUGH,” she said strictly to her assistant. Thick, creamy milk poured briefly from Penelope’s gaping mouth…
“…. sorr..sorry… I didn’t hear you…”
Cynthia back-handed her like a disobedient housewife… Penelope’s face snapped back… she had tears in her eyes…
“Hear better next time… It’s 11 O’clock. I’m behind schedule. And I need to have my ass licked…” Miss Cynthia said as she stood up and hitched up her dress around her beautiful love-heart-shaped arse…
She wasn’t wearing any panties… the sight of her huge fleshy mound made Penelope’s mouth water… it was hard to believe that Penelope had been a normal woman 2 years ago… now she was just a cunt-hungry titless lesbian with a gaping cow cunt…
“…of course, mistress…I’m so selfish… please forgive me…” Penelope replied breathlessly
“…you can apologize with your tongue… come here…”
Cynthia stood up and walked back to her desk… she opened her laptop and checked the time… 11:05… she still had some work to do… an appointment for a business call from one of her investment contacts… she had to double-check her cash and digital income data… and various schemes to inflate/crash the value of stocks – not just to benefit her…. but to cause harm for harm’s sake…
The world was a marvelous place… and being on Top was orgasmic… She hitched her dress up around her waist and pulled a knee-high stool to the edge of her desk… She pushed her bum out and pulled her laptop towards her… hitting 2 birds with 1 stone was the essence of Efficiency… and efficiency was the cornerstone of success..
“…Don’t stare at it… Eat It” She rudely said to Penelope… As Cynthia flicked through her emails, she felt 2 hands spreading her fleshy ass cheeks… then a warm, hard, penetrating tongue began cleaning her better than any shower could…
To Penelope, the sight of her Mistress’ asshole was a welcome sight… To any sane person, the sight of an asshole (even a clean one) would elicit revulsion… but to an intensely degraded and broken sub-slut it was incredibly arousing… She stretched the cheeks and observed them as they spread around her face…. an amazing sight… she wished she still had a clit to diddle so she could cum easier….
Only humiliation turned her on now… and there was nothing more humiliating than eating another woman’s asshole… she gazed at it for a split second… There was a strange tattoo… it looked like an inverted pentagram with the center being the asshole itself… she didn’t care… she was too cum-drunk to care…
Picking up her phone, Cynthia dialed her contact.
“…Hello… This is Cynthia Remington speaking … mmmm, oh yeah (her asshole dripped with warm, musky saliva)… yes…we talked over email…oooh…. yep, that’s the spot… I mean… email… (the tongue licked and kissed her ass hungrily)….
I’ve reviewed your business portfolio that your accountant sent me. I wasn’t aware of it. I’ve talked with my people to your people…OH FUCK… I’m CUMMING… I mean… sorry I was…ooohh… talking to someone (Penelope had started eating her swollen, puffy pussy like a starved minx)… uh yeh… I’ll be COMING to coffee with Shawn on Monday… and I think we’ve identified a loophole in your business plan… excuse me…”
Cynthia put the phone down and turned around. She spread her legs around Penelope’s head and pulled her head in… The Dominant Woman shuddered intensely as her pussy mound was devoured by the Subslut Lesbian Penelope… Cynthia silently cried in ecstasy as she squirted all over her assistant’s face and titless chest…
She breathed gratefully before turning around again… She lifted her dress again and invited her assistant to continue…
“…. sorry about that…. I spilled my drink and made a mess… ”
*****
Part 3…
Cynthia Remington’s fat pussy tingled from her recent orgasm… Most of her thick, creamy ejaculate still lay spattered on the police commissioner’s bruised face as he slowly came to his senses on the bed…
She barely had to try to break him… She supposed his wife had already broken him… or maybe he was just inherently a weak, pathetic man… She did come across as the effeminate, credit-stealing bureaucratic type…
He looked so respectable in his uniform… but naked on the bed with his noodle arms, beer belly, man boobs and receding double chin – he was simply a loser… Cynthia felt disgusted with herself for letting his body even touch hers…
If she weren’t a savvy tactical sort, she would have given in to her psychopathic desire to dispose of him simply… nonetheless – she needed him… for now…
Cynthia’s sleek, muscular body elegantly rolled off the bed … and walked over to the wardrobe…
It was a majestic piece of carpentry, carved from a solid piece of wood… the world’s largest and oldest tree was no more… 80% of it turned into wood shavings… and the remainder was a 16-ft-square masterpiece of faux Edwardian carpentry…
The sheer wastefulness of it always warmed her heart… She reached inside and drew out a long dressing gown of fine gold-laced velvet…
As she tied the robe belt around her tight muscular belly, she was thinking of having him clean her ass… but she didn’t want his piggy tongue touching her anymore…
She glanced back at his spread-eagled body… He was awake now and lamely pulling on his cuffs… He even dared to look her straight in the eye… It was a shame that men tended to stop being submissive after they’d dribbled their load… and this loser had cum twice…
His flaccid 2-inch dick was coated in its own watery jizz… He had actually cum just from her raping his face with her pussy…
“… can I… can you let me out?” He asked lamely. She sighed and felt the first embers of anger flare in her heart.
“Let you out? Why?… you seem to like being tied up…” She bitchily remarked
“(gulp)… I do… if you uncuff me… I can … fuck you?” he insolently mumbled.
Cynthia’s anger exploded before she could control it. She strode onto the bed as fast as a storm wind and had a foot on his chest… She applied too much pressure accidentally… She felt a sudden giving way under her toned leg and knew that she had broken at least 1 of his ribs…
He blurted out in pain as her foot pressed into his fleshy chest… She felt an intense rush of satisfaction at his pained cry… such genuine pain was music to her ears… She sorely wanted to continue – but common sense stopped her…
“… I’m… sorr…sorry…” he gasped
“… you really are pathetic… aren’t you?”
“… yes miss… (gasp)…i’m a joke… even my wife hates me…” he struggled to say. Cynthia’s anger died down slightly… such ‘voluntary’ self-deprecation was even more pleasurable than physical pain…
A flicker of a humorless smile crossed her beautiful angular face… Her piercing emerald-green eyes pierced his… He refused to look at her face out of fear… but looked up her leg at her beautiful hairy pussy mound and her heavy cleavage now revealed slightly by her partly open dressing gown… A drop of pussy juice dripped from her cunt and landed onto his chest…
“… yes, you are a joke … a fat little loser… with a small dick…don’t you have a small dick?”
“…yes Miss Cynthia… my willy is a joke…my wife laughs at it sometimes”
Cynthia smiled and removed her foot… She straightened her gown so he couldn’t see her tits anymore and stepped to the base of the huge sex bed…
“… I’m sure lots of people laugh at it… Your balls are small too… did you know that?”
“… what?…”
“… you have Small Balls… they’re as small as ping pong balls…” Cynthia declared as she cupped his ball sack under the toes of her left foot. It barely spread over the middle 3 toes of her foot and was slightly purple from when she had crushed them in her hand minutes ago…
“… yes… they are a bit small, I suppose…” He huskily muttered… his erection was coming back slowly…
“… small balls mean weak sperm… has your wife ever gotten pregnant?” Cynthia asked, as she flicked them with her toes onto his chubby thigh
“… no…” he muttered with pain in his voice.
“… and she definitely won’t be getting pregnant after I’m done with you…” Cynthia whispered as she kicked his left nut with ferocity that one would kick a rat scampering along the kitchen floor…
The police commissioner didn’t say anything… His whole body tensed, and tears began to form in his eyes… His left testicle was slightly ‘out of position’ and had a purple bruise on it…
Cynthia smiled with delight… she longed to crush the other ball and hear him cry like a girl… but she needed him to have his other testicle… lest she lose any leverage over him… he sobbed quietly as she pressed her foot over his little 5-inch willy… Interestingly, he had not lost his erection… In fact, he looked harder than before…
“… I know where you live, commissioner… I know everything about you… Look me in the eye sissy!” She burst out. At the word ‘sissy’, his eyes reluctantly focused on her intensely beautiful face…
She was still robed to hide her magnificent breasts and pussy… all he saw was a giant woman with piercing green eyes and lustrous ebony hair – one foot crushing his dick against his pubic bone ….
“… Stacy is taking the case… if you don’t go along with Everything she says-” Cynthia slowly moved her foot over to his remaining testicle and began putting her body weight down…
“NO.YES YES YES .. FUCK. I WILL DO WHATEVER YOU WANT…. ANYTHING… just please don’t hurt me anymore…” He cried out
“Good sissy… and when you behave… ” She opened her gown to reveal her watermelon-sized breasts. The nipples were at least an inch long… She moved her foot to his dick again…
“…when you’ve done your part… we can fuck… as Hard.. and for as Long as you like… and as often as you like…” She said as she jerked her foot back and forth over his 5-inch dick…
“…mmm… yes… anything … Anything… You owe me…” he muttered painfully. Cynthia smiled evilly at him and removed her foot. He had been on the verge of climax… she really enjoyed inflicting that sort of pain…
“Good…” She walked off the bed and strode out of the room… She wanted nothing more than to have a shower… her ‘assistants’ would help the commissioner in due time…
——–
Jemima desperately pawed through her sparkly purse… the money was gone!… he had robbed her… tears born of terror began gripping her heart… she had earned over 2 grand last night… and now it was gone!… she contemplated just Running Away… but Miss Cynthia’s officers would find her fast… The tracker in her butt cheek could not be easily removed…, and besides, they would find her anyway…
Tears ran down her face as morning traffic started rolling past her…what a joke she must look like – her fine fur coat was encrusted with mud, and her clothes were completely soiled… her bleeding nose really made her look like the tramp she was…
With a trembling hand she opened her phone…
“… hii… yeh it’s me… something’s happened…. ”
——
A rubber-gloved hand knocked on the expensive oak door.
“Come in, Penelope!” Cynthia called out loudly from the other side of the door…
Penelope stood in the hallway… She cleared her throat and hurriedly checked the mirror to her left… She saw a flat-chested ‘woman’ with short, thinning blonde hair. She wore overalls with big rubber boots. .. She looked like a balding effeminate male farm worker to the untrained eye… She was 30 but looked like she was aging well, though she was into her 60s….
Penelope forced herself to breathe as she slowly opened the door into Miss Cynthia’s office… She was sitting upright at her desk, typing at her laptop. She was dressed in a long black shoulderless dress with a pair of black boots over black fishnets…
She didn’t look up from her computer as she typed away…
“…You’re late, Penelope… My massage session was due 1 hour ago…”
“… I had to … deal with one of the girls…we had a call this morning… she didn’t call in last night… and this morning she claims she was robbed…”
“… punish her then in accordance with how much she owes”
“… I was going to… but she claims she can get us another girl…so if I punish her, it could negatively affect business growth… I wanted to bring the matter before you…”
Cynthia stopped typing and put her laptop off to the side… her emerald gaze fell heavily on Penelope like a guillotine of judgment. Penelope could barely contemplate lying… And she became acutely aware of how feminine and beautiful her Mistress was … in comparison to herself…
“Well… what are the details?” Cynthia asked as she leaned back in her chair
“Male… early 20s… no meaningful friends or family relationships… poor… but clearly loves the services of your workers so much that he will pay the price repeatedly… the ‘medication’ has been applied to him at least 10 times in less than 2 months…he’s deeply into Stage 1 development… we have plenty of footage of him being… serviced … the footage speaks for itself… he seems to be ripe for the plucking… and he has agreed to meet your girl tomorrow evening… I thought you’d like to know… ” Penelope stated matter-of-factly with a knowing look…
Cynthia smiled wryly… as she pushed her chair back.
“… you do do a good job of looking after the girls, don’t you… Penelope… I imagine you must have made quite a good mother…” Cynthia said as she turned to get up
“…actually… I was a mother…” she muttered, with a little pain in her voice as she walked to the corner of the room to retrieve the massage table. Cynthia looked at her with a hint of suspicion.
“You came here after school… you were going to study economics at university?”
Penelope stopped as she was about to lift the table and looked at her Mistress in surprise.
“..No miss.. I worked as a school teacher for 5 years… until your people found me and… showed me how… successful… I could be …if I did what they said…” Penelope muttered as she took off her rubber gloves, revealing a solid-gold watch on her left wrist…
Cynthia noted her slightly remorseful tone… and considered the potential for defection.
“Oh, of course… I mistook you for one of my former assistants… after the medication and the … celebratory rituals… you all tend to look the same to me… Any children?” Cynthia said in an almost friendly manner as she started undressing…
“… 2…. but then my husband saw your girls… eventually he couldn’t … pleasure me… he … or she…works here now” Penelope muttered as she looked down at her own feet – not failing to notice her non-existent breasts… She was acutely aware that Miss Cynthia had had many assistants… she didn’t dare inquire about their whereabouts.
“… You’re richer and more powerful than any school teacher, Penelope… never be ungrateful for the Opportunity i’ve given you… and never forget that you work For Me,” Cynthia declared as she gestured for Penelope to bring the table and towels forth…
The table was an ergonomic padded bench with a pair of Stainless-steel U-shapes attached in front. On either side of the bench were armrests…
As Penelope brought the strange apparatus forward, she felt herself getting slightly wet as her Mistress undid the loops of her dress to reveal her monstrous FF breasts…
Cynthia’s long black hair framed them almost perfectly as she sat down on the bench and looked expectantly at Penelope…
“…aren’t you happy you don’t have breasts anymore, my faithful Dyke-bitch Penelope…. and lay the plastic matting down… these rugs are a devil to clean…”
“… yes mistress…” Penelope mumbled. She knew what was going to happen… Cynthia often liked to bully her underlings… and Penelope liked … and needed… to be bullied… It was humiliating… and necessary…
“… I’m sure you love being Ugly and old, don’t you… flat-chested with thinning hair … soon you’ll be bald… just wait until our next celebration event… won’t that be nice … to be Liberated from the unfair expectations of womanhood?”
“…yes mistress… can … can I show you my … my shame…?…” Penelope mumbled… She was extremely wet now… her thighs were practically drenched as she had urinated herself.
“…yes bitch… you may…” Cynthia said with a growing smile as she watched Penelope undress…
Penelope started with her work boots. She placed them next to the wall. Then she took off her rubber overalls…. She placed them next to her boots… then she started undoing her leather belt…
Up until now, anyone would have assumed she was just a guy with hormonal problems… She was now dressed in tattered trousers and a long-sleeved blue shirt… the only nice thing she had was a gold watch she wore on her right wrist… and quite frankly… it was a Man’s watch….
She shuddered as she unbuttoned her T-shirt… She looked down her boobless chest and saw her little beer belly and a pair of long nipples protruding from her relatively muscly pectoral muscles…
She remembered when she had quite normal-sized breasts…. she wondered what it would be like to have proper breasts again… that could have fed children… that could have made her feel like a woman…and made men actually like her…
She then looked at Miss Cynthia’s breasts… They were almost as big as Penelope’s own upper body… the soft curve of them was intoxicating… They were Perfect… Penelope felt another gush of fluid come from her crotch…
She hesitantly looked down at her drenched trousers before continuing to undress… slipping her arms from the sleeves of the shirt, she threw it with the rest of her clothes… Finally, she undid her trousers.
They were sticky against her ankles due to her excessive vaginal discharge… she took them off and threw them gracelessly with the rest of her clothes… Now she was only dressed in socks… and her rich man’s watch…
“…mmm show me your crotch Penelope…” Cynthia ordered, leaning back in amusement…
Penelope’s face turned an extra shade of red as she took her hands away from her crotch to reveal her freakish pussy… It was lipless… wrinkly…fleshless… rimmed with a rug-like layer of hair…and gaping with a pair of flappy wings going down her soaking ankles…
She could have taken half a baseball bat in her Disgusting Pussy without noticing….and her clit was basically non-existent… Getting off like a functional female had become impossible for Penelope…
“Welll… it’s no wonder your husband wouldn’t fuck you…” Cynthia quipped as she slowly fingered herself… Penelope could barely understand how her Mistress could get off to her broken pussy and her titless chest… but Penelope needed the humiliation… it was the only way she could cum…
The ‘woman’ came out of her day-dreaming and stepped forward to grab each magnificent breast with 2 hands… She carefully placed the left one in the left cup… and then the right… They were so heavy… her Mistress’s back muscles must have been very strong to carry them around all day… As the last breast slotted into place, Cynthia sighed with relief.
“… milk me…” Cynthia whispered as she rested her hands on the armrests and closed her eyes. Her long black hair fell around her breasts like exotic ebony silken drapes… framing her breathtaking face and goddess-like breasts…
Penelope wasted no time as she pulled out 2 large aluminum buckets and placed each one under each heavy tit…
Starting at the top of the cleavage, she forcefully pressed all the pressure points to dilate the vessels that transported milk to the nipple… After stimulating these pressure points, she would massage the entire breast in a downwards motion…
Her mistress forbade the use of milking machines, strings or ropes… she preferred the ‘massage experience’ even if it took longer…. When the milk build up was sufficient, she would lower her salivating mouth to the nipple and suck…
Eventually the thick, creamy, pungent milk of her Mistress would fill her mouth up faster than she could swallow… The remainder of the milk she would squeeze into the buckets… When the milk flow slowed… she would start again…
Her big strong hands artfully caressed each breast… first the left… then the right… she had always found that allowing a break for each breast ensured the next load of milk was as efficient as possible…
A beautifully subtle and intricate network of pulsing blue veins showed in her Mistress’s boobs when she was lactating… massaging the breast tissue around the veins always seemed to please Cynthia the most… She groaned as the pressure in her breasts was relieved by the quivering hands and mouth of her assistant…
Needless to say… Penelope was incredibly aroused during the whole process… The humiliation of servicing such Magnificent breasts pleased Penelope excessively, considering that she had lost her own breasts on account of becoming the freakish broken titless female that she was now…
The buckets were almost full now… It was hard to believe that Cynthia’s breasts had actually increased slightly in size over the months that Penelope had worked as her ‘assistant’…
“mmm… suck me, Penelope…. The sissies will have enough milk, I think… mmmm,” Cynthia moaned as she lovingly drew Penelope’s head into her bosom… Penelope’s mouth sucked and swallowed eagerly for what must have been half an hour as she pathetically humped her crotch in rhythmic motions like she was riding a willing male slave… She was so close to cumming…. She looked up at her mistress’s relaxed face…
“… (suck slurp)… Miss.. (slurp)… Cynthia…(suck)… can I … (suck slurp)… cum now? (slurp)”
Cynthia lazily opened her eyes to see the small pool of liquid between Penelope’s ankles, where Penelope was kneeling… With a lazy kick of her right leg, she kicked Penelope in the crotch…
“What are you, Penelope?” She asked as Penelope slurped away
“…(suck)…I’m (suck, slurp)… a pathetic (suck) loser (slurp)…”
“…mmm … yes you are…” Cynthia smiled at her desperate subject’s admission. She kicked her in the crotch again… but Harder… and then again Harder… Harder…HARDER… The third kick caused Penelope’s bum to rise into the air with a deliciously Meaty Slap, which elicited a muffled grunt from her…
Her little beer belly jiggled from the blow… She gasped as she stopped slurping down milk and moaned in what could be described as a genuinely feminine quavering orgasmic cry… Penelope ground hard against her mistress’ ankle; she came as hard as a water fountain…
To Cynthia, it felt like she was trying to block a water jet in a spa… It really was amazing how much such an ugly woman could cum…
Cynthia checked her watch as her pathetic assistant diddled her gaping pussy and sucked away the last drops of milk… The pressure from her breasts was receding… she didn’t feel so irritated now… but she was still horny…
She was used to having her ass licked at least once per day… that pig of a police commissioner could keep his tongue to himself… she preferred the mouth of a woman… even if she looked like a man…
“Enough, Penelope…” she said as she reached back toward the desk to grab her phone… Penelope either didn’t hear her or ignored her as she kept sucking away at her tits…
“ENOUGH… ” Cynthia repeated…. She was surprised that her assistant was not responding.
She reached forward and grabbed her by her thinning hair… She pulled her head back excessively hard and pulled out a handful of hair…
“I said ENOUGH,” she said strictly to her assistant. Thick, creamy milk poured briefly from Penelope’s gaping mouth…
“…. sorr..sorry… I didn’t hear you…”
Cynthia back-handed her like a disobedient housewife… Penelope’s face snapped back… she had tears in her eyes…
“Hear better next time… It’s 11 O’clock. I’m behind schedule. And I need to have my ass licked…” Miss Cynthia said as she stood up and hitched up her dress around her beautiful love-heart-shaped arse…
She wasn’t wearing any panties… the sight of her huge fleshy mound made Penelope’s mouth water… it was hard to believe that Penelope had been a normal woman 2 years ago… now she was just a cunt-hungry titless lesbian with a gaping cow cunt…
“…of course, mistress…I’m so selfish… please forgive me…” Penelope replied breathlessly
“…you can apologize with your tongue… come here…”
Cynthia stood up and walked back to her desk… she opened her laptop and checked the time… 11:05… she still had some work to do… an appointment for a business call from one of her investment contacts… she had to double-check her cash and digital income data… and various schemes to inflate/crash the value of stocks – not just to benefit her…. but to cause harm for harm’s sake…
The world was a marvelous place… and being on Top was orgasmic… She hitched her dress up around her waist and pulled a knee-high stool to the edge of her desk… She pushed her bum out and pulled her laptop towards her… hitting 2 birds with 1 stone was the essence of Efficiency… and efficiency was the cornerstone of success..
“…Don’t stare at it… Eat It” She rudely said to Penelope… As Cynthia flicked through her emails, she felt 2 hands spreading her fleshy ass cheeks… then a warm, hard, penetrating tongue began cleaning her better than any shower could…
To Penelope, the sight of her Mistress’ asshole was a welcome sight… To any sane person, the sight of an asshole (even a clean one) would elicit revulsion… but to an intensely degraded and broken sub-slut it was incredibly arousing… She stretched the cheeks and observed them as they spread around her face…. an amazing sight… she wished she still had a clit to diddle so she could cum easier….
Only humiliation turned her on now… and there was nothing more humiliating than eating another woman’s asshole… she gazed at it for a split second… There was a strange tattoo… it looked like an inverted pentagram with the center being the asshole itself… she didn’t care… she was too cum-drunk to care…
Picking up her phone, Cynthia dialed her contact.
“…Hello… This is Cynthia Remington speaking … mmmm, oh yeah (her asshole dripped with warm, musky saliva)… yes…we talked over email…oooh…. yep, that’s the spot… I mean… email… (the tongue licked and kissed her ass hungrily)….
I’ve reviewed your business portfolio that your accountant sent me. I wasn’t aware of it. I’ve talked with my people to your people…OH FUCK… I’m CUMMING… I mean… sorry I was…ooohh… talking to someone (Penelope had started eating her swollen, puffy pussy like a starved minx)… uh yeh… I’ll be COMING to coffee with Shawn on Monday… and I think we’ve identified a loophole in your business plan… excuse me…”
Cynthia put the phone down and turned around. She spread her legs around Penelope’s head and pulled her head in… The Dominant Woman shuddered intensely as her pussy mound was devoured by the Subslut Lesbian Penelope… Cynthia silently cried in ecstasy as she squirted all over her assistant’s face and titless chest…
She breathed gratefully before turning around again… She lifted her dress again and invited her assistant to continue…
“…. sorry about that…. I spilled my drink and made a mess… ”
The End.
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