The following day saw Thomas at Audrey’s house. He was there to begin the chores she had promised him. The only problem so far, was that he didn’t know where she was. He wandered around aimlessly for a bit and then spotted a handwritten note on the refrigerator. It read: “Thomas- I ran out for a bit to take care of some important business. I will be back in about an hour. Feel free to use the bathroom if you have to. –Ms. Green.” He felt a little guilty about that last part referring to the bathroom. He was thinking he might actually take her up on it though, when he suddenly heard voices coming through the open kitchen window. From his position, he could see clearly into the kitchen next door. He watched Isabella Fortune enter with Audrey Green and the ugly brute from the other day. He was completely naked and on all fours. Ms. Fortune was showing off a metal bucket to Ms. Green who was staring into it in apparent disbelief. He watched as Ms. Green turned suddenly on one high heel and began wagging her extended finger at the naked male, scolding him for something.

As the next hour unfolded, Thomas stared straight ahead with his exposed cock in his fist stroking it. He saw the women lead the male further into the kitchen and then, as Ms. Fortune removed her skirt to reveal her lovely stockings, saw Ms. Green taking a wooden spoon from a drawer. The clothed women looked especially pretty in contrast to the gross, hulking male who was naked and sweaty from his indignity.

In Ms. Fortune’s kitchen, Audrey was doing as Isabella instructed her. She stood at the rear of the pervert and used the flat of the wooden spoon to heft his balls and tease them. She rubbed the coarse wood back and forth over his bare scrotum and scolded him softly as she did it. She was slightly flushed herself. She had never seen such a big pair of balls on a man before. Despite their fascinatingly large appearance, she thought them quite ugly and told him so. Abandoning his testicles, she began spanking him with the spoon at Isabella’s urging. She found it quite fun and proper to discipline him like a child.

Beneath dickhead’s legs his mammoth cock was bobbing stiffly in the air. His boner was living testimony to his love of this peculiar form of degradation. He gasped as he felt Ms. Fortune’s silky gloved hand squeeze his dick at its base. She was wearing a pair of white lace gloves that teased the sensitive skin of his erection as she handled it knowingly. He felt her very slowly slide her little hand down from the base toward the head, where she paused torturously and then began rhythmically squeezing the spongy head like the atomizer on a perfume bottle. She chuckled wickedly as he bucked up and down from the intensity of the cloth pattern woven into the gloves, biting into his cockhead. There was a sharp smack as Audrey brought wooden spoon down onto his bare bottom.

Back in Ms. Green’s kitchen, Thomas was beating off with a vengeance. He was sweaty and dull-witted with lust. Legs spread wide apart and his penis in hand he surveyed the decadent scene with horrified curiosity. He watched the women berate and tease the naked wretch at their feet and jerked harder on his own penis. Ms. Green who squatted down demurely next to him brought the bucket under the man’s crotch. He watched as she almost shyly reached under his bare bottom from the rear to help Ms. Fortune masturbate the big penis. He now knew what was in the bucket that had so captivated the woman. He remembered the way Ms. Fortune had beamed with pride as she showed off the contents 3; like a farmer with a prized milking cow. He felt faint. His head had begun to spin with the labor of his frenzied jacking and his eyes were rolling back into his head. He closed them and concentrated on the profound ejaculation that was forthcoming. Time lost meaning to him and all that mattered was painting Ms. Greens kitchen sink with his steaming hot load. He would clean it up later. She would never know. Never know. Never know. Oh god. It was going to be huge. He began to tremble 3; and then 3; he felt a stinging hard slap to his bare fanny.

His eyes snapped open and he turned to face the fully dressed Ms. Audrey Green, holding the wooden spoon in hand and glaring at him with hard accusing eyes.

“Shame on you! What on earth are you doing in my house half naked and playing with yourself?”

She brought the wooden spoon down again on his bare ass. Once. Twice. He shuddered with the force of his embarrassment. There was clearly no explaining this other than to admit his guilt. He was masturbating in her kitchen and looking at the perversion taking place in the house next door. Not waiting for any explanation, Ms. Green seized him by the ear and marched him toward the rear door to the house. She shoved him hard out into the cool morning air with his penis still exposed and his pants at his ankles. He heard loud female laughter and looked up to see a group of young girls in cheerleader uniforms standing in the alley not ten feet away. They were looking right at him and pointing with big smiles on their pretty faces. Audrey delivered another harsh spank to his reddening ass with the spoon.

“March! Right this second, Thomas. I don’t want to have to tell you again.”

He slowly got to his feet and started to draw his underpants up when she smacked his hand away and told him to leave them down. The girls were in hysterics. They continued to point at him with their fingers and make embarrassing comments about his privates on full display. One of them, a cute blond in a ponytail, reached down to the hem of her short skirt and turned her back to him lifting it up and flashing her adorable little white cotton panties at him. His stiffening penis reared up at the sight and made them laugh all the more. Ms. Green once again took him by the ear and marched him over to the house next door 3; to Ms. Fortune’s. His face was beet red and his ears burned with the girlish laughter from the cheerleaders he had been exposed in front of. He was led into the kitchen wear Ms. Fortune and her milking slave were waiting. In no uncertain terms, Ms. Green told him to strip. He quickly complied and the two dominant women eyed his nude body up and down. Isabella Fortune sauntered over and proceeded to strap his hands behind his back. Then she whispered something in Audrey’s ear that made her eyes go wide and her hand cover her mouth in dismay. She nodded her understanding, however, and the two went to work on preparing the young man for further indignities.

A half hour later, Thomas found himself in cruel bondage. He had been laid on his back naked with his entire upper body encased in some kind of leather straight jacket. This of course left him exposed from the waist down. His head had been forced into a tight fitting leather helmet that covered him entirely except for his mouth and two small holes for his nostrils. There was more 3; they had fastened some kind of apparatus to his mouth opening but because he could no longer see, he could only guess what it was. The thing had a protrusion that led into his mouth and kept it forced open. It was hollow as he could breath through it.

With the large sturdy rubber funnel in place on the paperboy’s face, Audrey stepped back to admire her handiwork. She was shivering slightly with lust at the plans Isabella had revealed regarding this new acquisition. There on the floor next to his leather covered head was the bucket from the kitchen. The bucket full of cum. She wrinkled her cute little nose up slightly from the smell of the stuff. With a nod from Isabella, Audrey smiled and hefted the pail up over Thomas’ face. She slowly began to tip it causing the white sloppy contents to roll toward the rim. There was a pregnant pause right before the sperm began to plop down into the funnel opening in big heavy dollops. Thomas recoiled at first and began to wriggle about in his bindings. There was no way for him to gain control of his situation. He was at the mercy of the neighbor ladies. He gulped down the awful semen to avoid drowning in it. It was bitter and sticky and so very very thick. His mind filled with images of the big penis and balls which had produced it and fought to turn his head but was held fast when Isabella used her black stockinged foot on his forehead to pin him down. In his discipline helmet he heard muffled feminine giggles and comments being exchanged as his mouth continued to be filled repeatedly with cum. His cheeks began to expand from the amount he took in. Soon, he was forced to begin swallowing almost nonstop to keep the tube clear. It seemed that the supply of sperm was inexhaustible. There was so much and it just kept coming and coming! Audrey did not relent and she tipped up the bucket to the point of topping off the funnel and letting him drink it down before filling it full once again. All the while she scolded and chided him as she poured.

Isabella Fortune was delighted at the job the young man was doing at eating from the cum bucket. She left for a moment to go to her closet and brought out a leather collar with a small id tag dangling from it. She proudly showed it to Audrey who had just put down the now empty bucket. Audrey smiled wickedly, as she read aloud from the tag: “Funnel”.

As day turned to night Thomas reflected on the indignities he had suffered so far. He had downed sperm from a large bucket, had been spanked and masturbated by Ms. Audrey, he had even had to suckle and clean the sweaty stockinged toes of both Women while they gloated over him and prodded him along with riding crops. This latest intrusion, however, was the worst yet. He had been buckled into a bent over kneeling position with his naked ass in the air. His head low and fastened with a leash to a ring on the floor. Behind him stood dickhead with his huge stiff cock near his ass. Isabella Fortune approached him from the side with a big bottle of hand lotion. She unscrewed the lid and poured a generous amount over her palms. As she smeared the lotion into her pretty hands she spoke to the paperboy.

“Now you get milked like cow, eh?”

She grasped his swollen cock in one greasy fist and began a very slow pulling motion. His balls jiggled under the pulling and his cock head flared around her fingers as they traveled up and down.

“You like your new name, huh? Do you? Funnel? I call you funnel because you so good at drinking down the ball milk.”

She laughed at his shame and continued her slow masturbation. Audrey was watching with rapt attention, her arms folded across her bosom. She slowly walked around him to stand at his rear next to dickhead. “Funnel’s” asshole was almost rhythmically opening and closing in time to Isabella’s wicked milking. It made Audrey smile.

“Oh yeah. Beat him off, Isabella. I can see his butthole winking at me while you do it.”

They both laughed at that and Ms. Fortune increased her pace and gripped the slippery penis more firmly in her hand. Her bracelets jingled exotically as her fist worked his dick over in a parody of discreet juvenile masturbation. After a bit of this to arouse him, she slowed back down and took dickheads large penis in her other hand. She jacked it with slippery, lotion covered strokes. Each time she pulled it she brought the big head closer to Funnel’s asshole. She was now jacking off two perverts at the same time and smiling all the while. When Funnel felt the blunt cockhead butt up against his tight anus he gasped. Surely they wouldn’t degrade him so utterly by making him take a cock up his ass?! Then he felt a second pair of womanly hands on his bottom cheeks, spreading them far apart to further expose his tiny opening. Isabella began working the fat head into the young man’s asshole, perspiring slightly as she did. It was slow going but she was a very determined woman.

Audrey stared, fascinated by the sight of the small male anus being stretched around the fat cockhead. She watched Isabella in her pretty stockings and blouse, looking so pretty and dainty as she continued to jerk off her paperboy while he was being sodomized. She knew the big penis would stroke his prostate and produce an enormous amount of cream from the young man. Once again she fanned herself with her hand as she saw the cock slide deeply into her young masturbator’s asshole. For the next twenty minutes or so the little kitchen was quiet, mainly because both males had been gagged. The only noises were those of cocks sliding back and forth, punctuated by harsh female remarks.

“Fuck it dickhead. Yes, you fuck his ass. Deep. Funnel, you cum soon. You come for mama with big dick up your ass.”

Audrey joined in, inspired by the sight of Ms. Fortune’s masturbation.

“Yeah. Oh, do it to him with your hand, Isabella. I’ll bet he has a really big load he wants to shoot.”

The kitchen, which had been denied so much privacy in the past few days was again intruded upon when a gang of young female eyes peered into it from the window facing the alley. The pretty cheerleaders bore witness from their hiding place and their mouths were all agape as they saw the dirty activities being performed. They saw the attractive older Women, one holding the kneeling male’s ass cheeks spread and the other lazily stroking his stiff dick and they all blushed prettily.

“Omigod!” Shelly whispered to her friends. She was the pretty pony-tailed blonde who had flashed her cute little white panties at him in the alley. “Look what they’re doing in there!” There was silence as they could only stare and marvel at how controlled the men were. They seemed truly helpless to do anything but obey their Mistresses, bound as they were.

Thomas, now known as Funnel, was overwhelmed by the sensations of the perverted acts he was being made to endure. That cock was so big up his ass! He hissed through his funnel as he felt the big dickhead rub against his prostate. It slid back and forth through is asshole like a relentless engine. Ms. Fortune was milking him just like a cow in a barn. Her soft greasy hand slid up to the base of his penis and then she would pinch it hard with two fingers to draw downward to the head. Her pretty little fingers would pause to tickle the bloated dickhead before sliding wickedly back upward to the base. Thomas was oblivious to his audience of cheerleaders 3; only the stroking that he was enduring in both his asshole and on his stiff cock. Audrey chose that moment to release one of his asscheeks and run a manicured fingernail down across his hanging balls. She had a smile on her face as she watched him shudder from the sensation. She would squeeze them every so often using gentle rhythmic motions as she held his ball sac in the palm of her sweet feminine hand. She saw his penis was an agonized purple color from the lazy, cruel stroking of Ms. Fortune’s hand as she jacked him off.

Outside, the girls were starting to giggle nervously from the indecency of it all. They all looked so cute in their uniforms and knee socks and saddle shoes. The skirts were all so terribly short that their little panties were continually peaking out from underneath in a most fetching way. They popped their bubble gum and continued to make remarks about what they were seeing.

“Look at that big hairy one buttfucking the other one. I mean 3; my god 3; he has got to have the biggest dick I have ever seen.”

“Lori!” Shellie slapped her friend playfully on the ass in admonishment.

“Its true. And look 3; he’s getting a handjob at the same time. God, what a pervert. That is so totally gross.”

At last, at Isabella’s urging, Audrey put her hands on Dickhead’s hips to bring him to a halt. His big cock was about halfway up Funnel’s asshole. She wrapped her delicate fingers around the exposed swollen shaft and began to gently masturbate him into the paperboy’s ass. Funnel was bucking slightly to try and bring himself off into Ms. Fortune’s hand. She would have none of that and spanked him sharply across his bottom.

“You stay still! Mama milk you, but you no move for her! You want spanking?”

He groaned pitifully into the funnel apparatus attached to his discipline helmet and shook his head no. He was feeling like he was getting close to the biggest orgasm he had ever had. His sac was bouncing around in front of the women, making a foolish spectacle of himself. But of course, he WAS a pervert 3; a lowly jerkoff and now known only as “Funnel”. His purpose was clearly spelled out in his name. He was now the jackoff toy of two determined ladies both old enough to be his mother. He would swallow down the creamy sperm he and any other male cows made just to amuse the women. The dark notion swallowed him whole and he felt himself beginning the arduous journey toward a mammoth ejaculation. Each stroke of Ms. Fortune’s hand now brought him closer. When her hand suddenly left his penis he began to whimper like a frightened puppy. Audrey, who stood behind him jacking off Dickhead, was still smiling as the big penis began to fire wad after hot steaming wad of ballcream up his ass.

“Oooooh, Isabella. He’s cumming! I can feel it shooting out of his dick and up the other one’s ass.”

Isabella chuckled softly and returned a moment later with a condom package. She opened it with a fingernail and proceeded to draw it up the thick penis hanging down between his legs like a cow teat. Once in place, she began to masturbate him again but at a quicker pace.

The girls outside were very excited by the sight of his condom-covered cock being worked over by the female hand. They had a perfect view of the milking.

“Omigod now they’re jerking him off into a rubber! I cannot believe this.” Cheryl, a redhead with a big ass was giggling as she watched. The whole scene at this point reminded her of a barnyard animal being milked of his sperm. Funnel was bucking and making embarrassing noises that made Audrey and Isabella both grin. Her hand was really gripping him hard now and stroking him firmly up and down.

When he finally ejaculated it was indeed mammoth. The thick creamy goo blasted out of his tortured cockhead to fill the condom tip as Isabella pulled on him to empty his balls. Audrey pinched at his scrotum with her long fingernails a bit to encourage him along. His cock was throbbing in Isabella’s little hand and soon he was panting and exhausted from his ordeals. Ms. Fortune smiled down at him as she slowly drew the rubber down off his still fat dick. She pulled it down like a woman pulling off a stocking and began to scold him.

“Shame on you! You make big mess in here little boy. Should we tell his mama on him Audrey?”

Audrey seemed to be considering it as she tapped her finger against her pursed lips.

“Well, I think it may shock the poor woman to know that her grown up little boy here is such a pervert. Still 3; no perhaps another time.”

Isabella slowly removed one of her silky black stockings and began to unfasten the funnel from the young man’s helmet. Then she forced the odorous foot part into his mouth and told him she would be leaving for a while and when she returned she expected the stocking to be cleaned spotless. He nodded stupidly and the young girls outside all broke into laughter. Especially Cheryl.

“Hey, he should clean my dirty socks too. They’re pretty smelly and could use a good mouth washing.” They laughed even harder at that.

Lori said, “He should clean all of our dirty socks. The pervert would probably cum all over from that.” More laughter.

The women left Funnel in the room alone. They had Dickhead back on his ball leash as they led him to his little cage. Thomas was suckling the dirty stocking in his mouth in a frantic effort to clean it to Ms. Fortune’s satisfaction. His anus was sore and his cock was hanging heavily downward between his legs. His balls felt drained and very exposed as he knelt there in his straightjacket. The young girls in the alley watched a bit longer and then left to go to their cheerleading practice. They discussed what they had seen the whole way there.

He heard the sound of high heels striding across the linoleum floor and looked up to see both Women had returned. They ignored him and took seats at the kitchen table. Ms. Fortune lit a cigarette and blew a cloud of smoke.

“His mama will have to know, Audrey.” She said.

“I know.” She had a concerned look on her face.

“If you want to keep him she needs to know what is going on and what his future is, no? I help you if you like. I know a way to do it so his mama will want to have you take him for this.”

“Really? That would be nice, Isabella. You know so much and I want to learn it all.”

Ms. Fortune turned to look down at Funnel on her kitchen floor.

“Hey! You do good job on my stocking, boy. You make nice and clean or I spank.”

She pushed her chair out and got up to stand in front of him. She reached down and forced a finger into his mouth to remove the damp ladies hosiery. She uncoiled it and smoothed it out to examine the silk carefully.

“Is okay. You clean Ms. Green’s stockings this way now. You do as she say.” As she spoke she produced a thick leather collar and began to buckle it around his bare scrotum. She hooked a leash to it and handed it to Audrey.

“You take him home. I will call you before I go to visit his mama. You do what I say. This boy will be yours soon.”

Audrey rose from her chair and tugged smartly on the ball leash.

“Come along now you dirty little boy. You’re coming home with Mommy Audrey.”

Her sexy stockinged legs hissing as she moved, she went to the rear door that led into the alley. She led him out through this door as he stared at her beautiful large behind swaying in her skirt. His nostrils flared as he saw the cute panty lines that teased at him through the fabric. With leash in hand she pulled him along by his sac to her own home as Thomas followed along obediently on all fours, his balls swinging nakedly as he did.

Isabella Fortune had a drawer filled with condoms. These condoms, however, where not in the package. They were used and filled to bursting with thick creamy semen. The ends had been tied off into cute little knots and they sat in neat rows inside the drawer. She selected several of the filled rubber cylinders and put them into her purse. She took one more out and cradled it in her white-gloved hand as she examined the milky contents inside. She smiled at her clever plan to discredit the younger male.


Thomas’ mother was in the living room drinking coffee and watching the television when the doorbell rang. She got up and looked through the peephole to see Ms. Fortune standing outside looking very upset. She opened the door to greet her.

“Ms. Fortune. What can I do for 3;” the Italian Lady interrupted her.

“I am very angry for what he do to me! I have never had such a thing done before 3; I am a lady! He needs to be punished!”

“Ms. Fortune, I don’t understand. What’s wrong?”

Isabella reached into her purse and pulled out a sheer, pretty gray stocking 3; absolutely covered in sperm. The young man’s mother blushed and her eyes went wide at the sight before her.

“I 3;Is that 3;?”

“It is cum. Dirty boy cum from your dirty boy, yes!” She waved the fabric in front of her eyes accusingly.

“He go to bring me newspaper but he do this to my stocking! He make his disgusting bad boy mess from his penis all over my things!” She reached back into her purse and pulled out another garment. As she held it up in front of them, they unfolded to reveal themselves as a very pretty pair of silky full-cut pink panties 3; also covered in semen. Thomas’ mother didn’t think to question why the stains seemed so fresh, instead she was filled with revulsion and indignation. Ms. Fortune continued.

“I bet his bed 3; his underpants 3; his things are also very bad. Very soiled.”

The young man’s mother thought back to seeing the heavy creamy stains all over his bedroom window as she found him sleeping naked on the floor. Oh god, her own son was a pervert! At Ms. Fortune’s insistence, they climbed the stairs that led to his bedroom to conduct their inspection. When they opened the door, they saw a messy room with clothes on the floor and bed unmade but Ms. Fortune said they should begin with a search. Thomas’ mother went to the closet while Isabella picked up a pair of white briefs from the floor. She covertly dipped into her purse for a condom and split open the tight shiny white rubber with her fingernail. She then dumped out the gooey sperm into the young man’s underpants, making sure the cotton was quite saturated. She also took this moment to use another condom to squirt sperm all over his bed sheets. A few moments later she saw the boy’s mother come out of the closet with a black bag in her hands. She told her neighbor how sorry she was and that it was filled with dirty, filthy pornography. Isabella showed her the soiled underpants and the sticky bed sheet.

Ms. Fortune was very pleased with her performance so far and she actually shook her finger at the woman as she spoke.

“I am not so surprised. He is very dirty to do this to my things. He makes dirty mess in his room with his dirty magazines and should be very ashamed.”

His mother nodded gravely. “I could not agree more, Isabella.”

Audrey was very comfortable on her new chair. She was glad to have gotten the loan of it from Isabella Fortune. It was a large piece of furniture that was referred to as a Lady’s Throne. It was made of comfortable white leather that allowed for long hours of seated bliss 3; but that was not its most delightful feature. It also sported a carefully recessed opening in the seat. An opening through which a male face now protruded, held fast by leather straps that wound under his head and held him immobile for his duties. She had thoughtfully pulled her pretty panties down to her ankles before sitting to allow for her full bare bottom the play of his tongue. It was very busy in her anus at the moment. The lower half of him was naked and exposed as it protruded from the bottom of the throne and between her legs. She teased him with the feel of her panties against his cockhead and occasionally tugged hard on his ball leash to encourage his efforts.

“Deeper, please Thomas. I want to feel that tongue of yours all the way up my ass.”

He would have answered but his only reply was to burrow more deeply into the woman’s asshole with his tongue and to suckle hungrily with his lips against the opening. His penis throbbed against the teasing feel of her baby blue panties.

Ms. Green was allowing her asshole to throb pleasantly open and shut around his eager tongue as it worked in and out. She smiled as she thought of the dirty things that she would make the young man do for her entertainment. His tonguing and burrowing of her asshole was just a temporary diversion until she heard from Ms. Fortune. She was going to let the pervert's own mother know how dirty he was. It was a plan to free the boy up for his permanent duties of asslicker and jackoffboy. She wiggled her full behind upon his face and giggled at the feel of his face wedged deeply into her asscrack... where it belonged.

"Oh my, that's lovely sweetie. You are a little assboy aren't you? Mamas little asslicker hmm?"

He was showing her that he was exactly that. His face was pressed absolutely flush with her womanly asscheeks and her butt in his face gave him a tremendous boner. Audrey reached a dainty hand down and grasped the head firmly between two fingernails. She slowly pinched and squeezed it as her bottom received its due. When the phone rang, she released his penis and pulled hard on his ball leash.

"I have to get that call Thomas. You be a good boy while mama is on the phone. Lick my asshole deeply, please."

He grunted underneath her like a pig in a sty and continued to grind his face against her butthole while suckling hungrily. He had so far managed to cram his entire tongue deeply into the muscular anal ring of her tight asshole.

"Yes? Oh really? That shouldn't be a problem. How was she? Oh how lovely... give me about ten minutes. What? Oh... yes... the chair is wonderful. He has his tongue all the way up my butt right this minute. Mm hmm...Really. Okay... bye." She set the phone back into its cradle and addressed the young man under her seat. "Thomas... we have an appointment to keep. Please take your tongue out of my asshole."

When he opened the door to his house he wasn't sure what to expect. Ms. Green had told him that his mother wanted to speak to him and that she would accompany him. The blood rose to his face in humiliation when he saw his mother and Ms. Fortune sitting on the sofa along with a pair of his underpants and an unsettling familiar black bag sitting on the coffee table. He didn't think things could be worse for him just then. That was until he saw Dawn from the Adult Bookstore waltz out of the kitchen with a tray of Oreo's and a big grin on her cute face. She plopped herself down into a chair and put her feet up on the coffee table right next to the black bag. Despite his horrendous shock at the sight of her, he took the time to notice her young shapely legs in a very fetching pair of white cableknit tights. Dawn caught him staring and gave a little-girl giggle.

"Hiii Tommy." She cooed and gave him a little wave with her hand.

He was lightheaded and he turned to face his mother and Ms. Fortune. They were not smiling.

"Here he is Emily." Audrey said, addressing his mother.

"Yes. Thank you Audrey."

He fumbled for something to say. "What is it, Mom?"

His mother picked up his white cotton briefs with two fingers like they were contaminated and held them up disdainfully. Dawn giggled again and wolfed down another Oreo.

"What have you to say for yourself, Thomas?"

He didn't understand what his mother meant, but if Dawn was here, that couldn't be a good sign. He only knew her from his frequent visits to the sex shop near the college. He glanced over at Ms. Fortune who was glaring at him and offering no explanation.

"I... I don't know what you mean."

His mother laid the soiled garment back on the coffee table and proceeded to dump the contents of his black bag out onto the table. A bottle of masturbation lubricant tumbled out noisily and rolled onto the floor along with several dirty magazines, and lastly, his new jackoff pump. Dawn's eyes grew wide when she saw it.

"I remember that. Have you been using it, Tommy?" She was teasing him and loving every minute.

His face was completely crimson now. He stammered but could find no words to suit the magnitude of his shame. Ms. Fortune broke the silence.

"He is very dirty! He play with his penis and make nasty mess in his little room. My mama would spank such a dirty boy."

His mother spoke next.

"You remember Dawn? She certainly remembers you. She's told me you spend a lot of time at her store near campus. She's also told me you play with yourself in the little booths they have in there... for dirty men. Shame on you, Thomas!"

He felt as if he were going to cry at any moment. Then, as planned, Audrey volunteered a solution.

"Emily. Why doesn't he stay with me for a good while? You know that I don't tolerate that kind of behavior. He's been shaming your good name for some time, and I think the firm hand of his neighbor lady might be a good influence on him. And it would give you some time to get yourself back in order... I'm sure this has been a terrible ordeal for you."

His mother sighed and nodded. "Perhaps your right, Audrey. Perhaps it would be what he needs. However, there is still the matter of preserving my motherly honor, to say nothing of the punishment he has coming to him."

Tom gulped and looked to Ms. Green for support. She offered none as his mother continued.

"Thomas. Take your pants off."

He knew it was useless to argue with his mother when she had that determined look. He slumped his shoulders in defeat and began to unzip and undress himself in front of the four women. He pulled his pants off completely and stood there in his shirt and briefs and socks as Dawn smiled at the sight of his bulging underpants. Despite his mortification, he had somehow managed to pop a very rigid boner. Then, his own mother took him in front of her and Ms. Fortune, and began to lower his briefs for what appeared to be an old fashioned spanking. He almost began to whimper when his stiff cock was revealed to the cool appraising stares of the women. As Ms. Fortune stared at the swollen head, it throbbed and a blob of sperm appeared at the slit. His mother sniffed angrily and proceeded to scold him, as he stood there ashamed and fully aroused.

"You're behaving like a beast. I simply cannot believe that you would expose yourself so... so shamefully in front of guests. You certainly aren't impressing Ms. Green or Ms. Fortune. Poor little Dawn is probably going to tell all of her girlfriends about the pervert son of mine. And Thomas... I am most certainly not impressed in the least."

With that, she brought her hand up to his throbbing penis and closed her fingers around it tightly. He gasped at the maternal touch and his balls raised and lowered in the throes of his decadent need. His mother proceeded to pull downward in an agonizing slow movement that slid her feminine hand to the slick taught head. She paused to examine the spongy head and squeezed a few times rhythmically. Dawn was holding her breath; she was so transfixed by the sight of the mother prickteasing her own son.

"Just shameful." She hissed as she stared at his penis. She seemed to be addressing his cock and completely ignoring him.

"A wicked display. Just wicked." She actually stroked his hard shaft a few times between comments. Ms. Fortune also spoke to his penis.

"Very dirty. It is big and fat from dirty thoughts. Make a big mess soon."

Thomas was trembling with the lust that was boiling in his fat ballsac. His own mother had his penis in her hand and was pulling on the boner he had so embarrassingly revealed to her. She had never seen him like this... with an erection... and she seemed transfixed by the sight of it. She brought her other small hand up to cup his tender scrotum and Thomas could feel the cool steel of the rings that encircled her fingers as they touched his balls. She stroked his hard cock very very slowly while slowly squeezing his balls. The room was very quiet. Then, abruptly she stopped her teasing caresses and ordered him across her lap. He obeyed nervously and soon found his penis treated to the subtle rub of her nylon dress pants. With his naked rear end now in the line of fire, his mother proceeded to slap him smartly while scolding him.

"You are a very naughty young man, Thomas!" SMACK!

"You deserve this." SMACK!

"I wont..." SMACK!

"tolerate this nastiness!" SMACK! SMACK! SMACK! SMACK!

The spanking went on for a while with Thomas sobbing on his mother's lap. The women watched with silent interest while he bucked and whimpered and accepted his punishment. Eventually, despite the burning in his fanny, he began to buck harder against the fabric of his mother's nylon pants. The teasing feel against his naked cockhead was driving him toward a very embarrassing accident. When he came, it was with a resounding spank against his bare ass and a curdled yelp. Emily instantly felt the hot thick ropes spurting against her thigh and flipped him over to avoid further soiling. The move caused her son's exposed cock to stand straight up in front of the wide-eyed women while he lay on his back on her lap. His cock gave a terrible throb and then spit a long white rope of jism that landed in a spiraling plop all over his shirt and part of his mother's blouse.

When the spectacle had reached its conclusion, his mother dumped him to the floor and reached down to take a firm grip of his ear. She marched him into another room while the women all looked at each other in astonishment.

Dawn let out a breath. "My gosh. That has got to be the biggest cum load I have ever seen. Did you see how much he squirted?"

Isabella was smiling smugly. "It is his mama's touch. Such a dirty boy. Such a big mess from him from that."

The women continued to discuss him in hushed tones, afraid they would miss any further punitive dialogue from Emily to her son. Then, they returned to the living room with Emily leading the way. She had taken the time to remove her semen-soiled blouse, revealing her full bosom in a modest white old-fashioned bra. When she came in and resumed her seat, Thomas was still outside... apparently too embarrassed to enter.

"Thomas!" His mother barked. "You will come back into this room this instant!"

The women now all had their eyes fastened on the doorway that led from the kitchen into the living room. Slowly the giggles started as they beheld the young man and what his mother had done to him. He was wearing a diaper.

Audrey was grinning from ear to ear and clapped her hands together as he slowly shuffled into the room.

"Ohhh, Emily! That is so adorable!"

Dawn couldn't stop laughing and Isabella was characteristically smug.

"Is good for him. Diaper for little baby who make mess on mama's lap."

His mother looked at him and wagged a scolding finger. "This is what happens to boys who don't behave like men. Take a good look ladies. Thomas should be very ashamed of himself. Now you may go to Ms. Green's house where she will look after you for a while."

He looked around for his pants.

"No pants, Thomas. Those are for big boys. You will go as you are... in your diaper."

That was it. His fragile masculinity shattered, he began to sob with shame in front of the pretty women. Audrey took him by the hand.

"Come along, you sad little baby boy. Lets get you home now."

He unquestioningly followed her out the door and back to her house... clad only in the humiliating baby garment. Once back at Audrey's house, he was put back under the Lady's Throne where he spent the remainder of the afternoon... making her asshole feel loved.

Days and weeks passed until one day Thomas' mother decided on a visit to see how her dirty son was coming along under Ms. Green's care. She had chosen her clothing very carefully, as she didn't want to entice him to another disgusting erection. She was the picture of a prim lady. Her blouse was a white high-collared affair complete with long sleeves that ended in a pair of white silk gloves. She had chosen to wear her brunette hair pulled back into a bun to give her a more dignified appearance. Her skirt was down to her ankles and her feet were in a pair of sensible black heels. Her only concession to womanly vanity was a pair of beige silk stockings with a reinforced toe. These were held up by thick white straps that attached to her matronly white girdle. The stockings had been a gift from Ms. Fortune over the holidays. She had been spending much time with the young male's mother in an effort to subtly groom her into a more suburban version of herself.

In Isabella's company, Emily had been treated to the sight of a naked male masturbating himself in front of her. It had been arranged to look like an accidental viewing, but it had all been cleverly planned with dickhead jacking off in a bathroom with the door open. In the days following, Emily had slowly begun to hone her beliefs into razor sharp clarity concerning her son.

Emily watched as Audrey's car left the driveway and she pulled out behind her. Following at a distance to avoid notice, she wound through streets to arrive at a small building in the warehouse district. She watched as her son's new governess descended steps that led down to a door into the lower level of the building. She left her own car and briskly walked over to the same steps when a noise startled her. There was a single broken window next to the door. It was small and the thick glass had been shattered enough to allow her to peer in. As she did, her mouth dropped open in utter shock.

Emily stared at the sight of her son. He was naked and bound wrist to ankle on his back. His ass was raised up to allow a very pretty, young blonde girl on a stool, access to his privates. She was smiling sweetly as she petted his boner and lightly tickled his exposed balls with her pink fingernails. At his head, four other males were standing on tiptoes with their heads encased in black leather hoods. They were bound to the ceiling by their wrists and their hard penises were all being solidly gripped by more pretty, young girls. They were masturbating them over her son's head. He had a shiny black funnel wedged into his mouth and it was kept there with stout leather straps. My god, thought Emily. What has my son become?

As she continued to watch, she became aware of her silky white panties becoming slippery in the gusset. She was in heat from the level of perversion she was being exposed to. Never had she witnessed such filth as she now saw... four stiff cocks ejaculating from the teasing hands that masturbated them expertly. The girls pointed the rigid boners downward; bringing winces and groans from their male cows, as they continued to beat them off. The thick, copious discharges all landed with surprisingly loud splats into the funnel strapped to her son's mouth. The girls giggled as they emptied the balls of all four men with firm milking motions.

Then, with a deep breath, she entered the building to visit her son.

Upon entering, Emily noticed for the first time that both Ms. Green and Ms. Fortune were seated there with a perfect view of the scene in front of them. They were in comfortable chairs and flanked on either side by ten other women whom she didn't recognize. Immediately, Isabella got up from her chair to greet the woman.

"Emily! Is so wonderful to see you here."

"Isabella. What's going on? What's happening to my son?"

Isabella smiled to show her shiny, perfect teeth.

"He is being fed his dinner." Emily cast a baleful glance over at her naked son on the floor.

“You mean you feed him semen, Isabella?”

Ms. Fortune chuckled. “Yes. Crackers and fruit and milk 3; but mostly semen.”

His mother looked down at her son’s bobbing erection being slowly pulled on by the young girl as she carelessly popped her bubble gum. For a moment their two eyes met and the girl gave a bright friendly smile and giggled as she used his penis to wave at her in greeting.

The young man’s mother blushed and she stared at the big naked cockhead swaying at her as the girl moved it.

“Is he any better in this situation? And who are all these women who are watching?”

Ms. Fortune raised a gloved hand. “I will answer all. Now, you sit. Watch your dirty boy make his mess.”

Emily was still working through the scene she was witnessing. Too dumbfounded to do anything else, she took a seat between Audrey and Isabella.

Ms. Fortune strode over to the girl masturbating Funnel’s penis and whispered something in her ear. The girl nodded and left the room for a bit. More girls entered and in a short time had put him into a milking harness. It was composed of leather straps that wound around his upper torso and arms pinning them behind his upper back. Two sturdy straps wound around his thighs, spreading them immodestly. The whole affair was suspended from the ceiling and supported him while leaving just his tiptoes on the floor. His bare ass faced the female spectators who had a superb view of his naked ass, hanging balls and cock. Then, the lights were lowered with just one bare bulb above the nude young man who was to be milked. Two cockteasers removed his helmet and funnel, revealing his red sweaty face 3; and cum smeared mouth. Snickering at the sight, the girls sharply turned their heads as Ms. Fortune summoned them over with an authoritative snap of her fingers.

“Mia. You and the girls attend to Ladies needs now.”

Mia blushed prettily and nodded her head, her short red hair beautiful in the way the light caught it.

“Yes, Ma’am. At once.”

The pretty cockteasers who had been so masterful in the way they had dealt with those rigid penises now walked to one of the older women seated comfortably for the show. Each girl then knelt down before them. Only Emily was left unattended and could only watch as each woman smiled smugly and raised her skirts before lowering them again over the heads of the young girls. With a tingle in the crotch of her panties, she realized the girls were eating their pussies beneath their conservative skirts. She glanced to her right and left and saw the round pantied bottoms of the girls as they wiggled contentedly and the skirts bobbed over their heads. Ms. Fortune gave a luxurious moan and then a sharp gasp.

“Ohh 3; she’s found my clit with her tongue.”

She reached down and delivered a harsh smack to Mia’s panty covered ass.

“Harder you little bitch. Harder. Yesss.”

Emily fanned herself from all of the female heat she was experiencing. It was all so very wild and naughty to her. Ms. Fortune looked over to her with a dreamy smile on her red lips.

“These women 3; are patrons of the arts. They come to see dirty things like your boy and what I make him do. They like very much. They pay money 3; oh god 3; my clit you little bitch 3; oh 3; oh 3;. Uh 3; and so they come and watch and I let them see what he do for me. Is good for him. Keeps him humble.”

Emily watched the way the little cockteaser was moving her head under Ms. Fortune’s dress as she reflected on the explanation. My god, she thought. This is all so wicked. But she could not dismiss the importance of, if not breaking her son from his filthy ways, at least keeping him absolutely humble to the point of easy handling.

Moments later his masturbatrix entered. She couldn’t have been a day over eighteen years old. She stood only 5'2” and was wearing a white T-shirt with the word “cockteaser” written in bold feminine pink cursive. She came out and slipped off her little black mary janes, then shyly removed her plaid skirt. Her sweet little pink panties were visible under the hem of her T-shirt and had little flowers all over them. Her feet were in white ribbed cotton knee socks and she had her short blond hair in adorable pigtails tied with pink ribbons. She was chewing bubble gum and grinning from ear to ear now. Despite her girlish appearance, Thomas noticed there was something hard about her. As if he could easily see her with a cigarette dangling out of her lipsticked mouth as she used words like ‘cock’ and ‘jerkoff’ to describe the male sex-act. She stood next to the bound young man for a moment with her socked feet together almost shyly turning one ankle and looking out at her audience from under her blond bangs.

“Hi everyone. I’m Kelly. If its okay, I’m going to 3; you know 3; do it to him now.” She giggled as she finished and lowered her eyes. Her cheeks blushed prettily at her own words.

Ms. Fortune raised her head and responded.

“Is good Kelly. Begin now. Milk him good 3; his Mama is watching.”

Kelly grinned and smiled at his mom. She gave a little wave at her before she turned to face the male called Funnel and leaned up on tiptoe to whisper something in his ear. The posture caused her little T-shirt to ride up high, and Emily noticed it exposed all of her cute, pantied rear end. Her ass was round and a bit chubby in contrast to her small-boned appearance. She is a born cockteaser, thought the older woman. At such distance, Emily couldn’t hear what she had whispered to her son, but all the women could hear his tortured groan in response. Kelly giggled harder and covered her mouth in a gesture of modesty. Then, she reached down and gingerly cupped his full scrotum in her tiny hand.

“Oh my.” She said in low tones. “Such big balls. Big balls full of cum.” Then she squeezed them gently and released them with another giggle.

“Naughty, naughty, naughty. Shame on you. Shame, shame, shame.” She wagged one finger at him while scolding; even as her other hand gently recaptured his sac and squeezed his swollen nuts.

She slowly strode around to stand at his rear and leaned over to tickle his balls with one of her pigtails. As he felt the girl’s baby-soft hair prickling his bare sac he gave a mighty groan of sexual agony. The ladies in the audience broke into hushed whispers of approval at his treatment. Kelly was having fun. She reached further between his spread legs to take his rigid cock in her fingers and pull it sharply downward. Then, she wrapped the blond hair of her adorable pigtail around and around his shaft up to the swollen head. Slowly she worked her fist up and down his hair-encased boner 3; teasing him with the wicked new sensation. On his tiptoes he tried to hump his ass slightly, mimicking fucking.

Emily was riveted by the sight. She was caught in some dark, erotic place between maternal outrage and thick heady lust. Her nipples were stone hard and were completely visible despite her puritanical undergarments and dress. Isabella noticed them though, and leaned over to her to whisper softly in her ear.

“Do you see how hard his penis is, Emily? Like bone. Kelly will make it spit. She is good 3; you see.”

Emily never took her eyes away. She watched as the young girl played with her son’s penis in a familiar way, without any reservations that this was her privilege and his sentence to be carried out.

Kelly was whispering to him again. Her little hands were gently slapping his stiff cock back and forth between his legs as he made little whimpering sounds 3; as much from her words as her actions.

“I’m going to make you squirt your nasty stuff in front of Your mom and all of those ladies who are watching you, you dirty, dirty boy.”

He hissed through clenched teeth as she suddenly pinched his fat dickhead between two fingers and tickled the underside of his shaft with pink fingernails. She traced her nails up and down the bloated surface under his penis where the concentration of nerves and vessels were hot to the touch. His cock would have been leaking precum already if not for her tight grip on his mushroom head. The cheeks of his bare bottom were tensing and releasing in full view of the women who watched his obscene display with wide eyes and reverent silence. The girls between their legs licked and sucked their pussies oblivious to anything but pleasing their Mistresses.

Kelly then pulled his very stiff boner back through his legs from behind so all the women had an unobstructed view and began to lightly pull on it as if she were milking a cow. The unnatural angle she had forced his cock into caused him to wince even as he enjoyed the masturbation that formed a wicked counterpoint to his suffering. The taught skin of his boner was drum tight, every nerve was alive and her little hand was so lovely on him. It was strong and firm as it beat him up and down in long deliberate strokes. She did it to him for quite some time 3; cooing and teasing him all the while with her dirty baby-talk.

“Your mommy can see how hard your penis is. It sure is a big one 3; your pee-pee I mean.” She giggled.

“I’ll bet if she were closer she could see how full your balls are too. Full of all of that nasty, dirty boy-cream. If she held them, I’ll even bet she would be grossed out by how full they are.”

Funnel gasped at the thought and was grateful that he had his back to her and the rest of his female audience. His embarrassment was as mammoth as the teased sex organ in her pumping fist. For the first time, he noticed several of the other women under Isabella’s employ were peeking at him through the doorway that led to the other room. He could clearly make out Tiffany and Elise 3; two girls who often prickteased him before putting him to bed in his dog cage. Laughing as they fed him their dirty stockinged feet and probed his anus with their greased fingers and then diapering him for a night of celibacy in his shameful prison. They were staring wide-eyed at Kelly’s expert handling of his penis, with big grins on their pretty faces. When Elise caught his eye, she slowly raised her little green skirt and loosely stroked her closed fist in front of her white panties as if she were mimicking a boy jacking off. He shuddered at the way she mocked him and robbed him of any dignity.

Suddenly, Kelly’s lovely hand slowed to a torturous stop. She turned to face the Women again.

“Um, would it be okay to have some help? I mean 3; I want to stick something up his bottom and if someone could help me spread his cheeks?”

Isabella stared hard at the stiff nipples that were angrily pushing at Emily’s blouse. She leaned into her again and whispered close to her ear.

“Oh Emily 3; Your nipples. So hard, dear. Go on. Help Kelly with your dirty boy. She needs help. You help her. Go on. We are all so busy and you are free to help.”

Emily, as if in a trance slowly rose to her feet. She was intoxicated by the sight of her naked son and what his masturbatrix’ fist had done to his penis. She walked closer to the harness he hung from and reached out with shaking hands to take his bare bottom in her gloved hands. She squeezed them for a moment in an unconscious gesture of female lust 3; before spreading them wide open to expose his private opening.

“Thanks a lot!” Kelly chirped. “That’s perfect.”

The cute pigtailed girl then retrieved a sizeable buttplug from a nearby table and brought it over to his face. She inserted it into his mouth and told him to suck on it like a pacifier. Then, she leaned up to whisper into his ear.

“You know 3; that’s your mom who’s holding your butt open. And everyone can see your asshole. I’m going to have her put that plug right up your butt. Do you think she’ll do that for me?”

With his mouth occupied by the cruel buttplug he could only moan. He looked over at Tiffany and Elise again and saw they were making faces at him and stifling laughter. His mother’s hands were on his bare ass and his heavy ball sac was hanging below 3; inches from her gloved fingers. He shuddered and it caught his mother’s attention.

“Is he okay? Why is he shaking like that?”

Kelly came around to where Emily was standing, holding his ass open.

“Oh 3; I think he’s just very excited by your touch. I think he likes the way your gloves feel on his bottom. I even think you made his cock harder.”

Emily was already blushing but she flinched by her use of the word ‘cock’. To her, it seemed somehow especially dirty being issued out of the sweet face of the cute little Kelly 3; and she said it so casually! She glanced down between her son’s legs and saw no sign of his penis. Kelly reached down and with a single finger pushed the hard erection downward and back to show his mother.

“See?”

“Yes 3; yes, I see.”

“Do you see how hard it’s gotten just from having you touch his ass?”

“Yes. His penis 3;um 3;his cock 3; its very hard.”

“You know 3; you can touch it if you want. I mean your wearing gloves and all, so it wouldn’t be that bad. Why don’t you touch it? Touch his cock.”

Emily stared at the big head and the shaft. It was throbbing against the girl’s finger, but it was no match as it tried to rear up into a normal position. Kelly had mastered her son’s stiff erection with a single finger. Taking one of her hands from his ass, Emily reached down as if in slow motion to wrap her gloved fingers around the bulging shaft and gave it a long, very hard squeeze. It brought a gasp from her son. She squeezed harder. His cock didn’t give a centimeter. It was like iron in her fist and she soon found herself slowly sliding her gloved hand up and down the length. Her grip remained solid as she did it. She rested her other hand on her hip and found herself milking the big cock in a vice-like grip using agonizingly slow strokes. Kelly craftily stole around to Funnel’s front and whispered in his ear again.

“You know what? That’s your mom who’s stroking your cock.”

His face red with embarrassment, he stared straight ahead, afraid to look over to Tiffany and Elise and see their reactions to his mother masturbating him. Kelly was continuing her teasing talk in his ear.

“She’s wearing such pretty stockings. I can just see them below her dress when she moves. I bet her feet are hot in those high-heeled little boots she has on. The stockings would be sticking to her feet 3; all soft and silky in there.”

Just then, Kelly stumbled upon a wicked idea. Taking the plug from his mouth she sauntered around to his bottom again.

“Emily, do you mind pulling one of his asscheeks apart so I can see his asshole? I want to push this up inside it.”

Never stopping her almost punitive stroking, the older woman reached out to pull sharply at her son’s bare ass. The tiny opening was clenching and opening as if hungry. Kelly hacked a loogie onto the round rubber surface and began forcing the plug up his asshole. When he tried to escape the buggery on tiptoe, his mother abandoned his penis to deliver a series of sharp spanks to his cheeks. He relented and the plug slid home. Then, Kelly revealed her idea to his mother.

The two lowered Funnel to a kneeling position and quickly tethered him to the spot via several chains shackled to the floor. His legs were spread very wide and Kelly got a small wooden stool to place on the floor right below his raised rear end. His cock and balls hung just over the wooden seat and his plugged ass was quite visible as well. The crowning touch was a long mirror, which was placed directly in front of him.

He stared at his mother’s reflection as she began to undo the intricate buttons and laces that sealed her boot to her foot. When it was undone, she carefully removed it with a sexy hissing sound to reveal her dark stocking with its reinforced heel and toe. Kelly once again forced his very rigid penis backward to lie on the surface of the stool with the underside completely exposed and his balls resting on the base. His mother paused to wiggle her toes with a wicked flourish before setting the damp silk down on just the head of his cock, pinning it to the seat. He groaned and stared at the arrogant look on her face 3; his mother looked beautiful to him at that moment. Risking his small bit of dignity, he cast a wary glance over toward the doorway and saw both Tiffany and Elise were watching with rapt attention. They were no longer smiling but he saw both girls had their hands busy in their little panties as they watched his mother working him over.

The soft silky stocking was rubbing against his sensitive boner as she wiggled her toes and kneaded it with her skillful foot. She began the slow journey down toward his balls, dragging the silk fabric along the drum-tight surface of his penis, enjoying the heat that warmed her through her stocking. She patted the exposed underside of his shaft with her stockinged foot and chuckled deeply in her throat at the sight of her son’s asshole sucking greedily at his butt plug. Kelly softly encouraged her as she stared with wide eyes at his cock-torture.

“Oh my god, you’re doing it so slow! Emily your going to make him squirt all over your pretty stocking. He’s going to cum buckets from that.”

She moved closer to the woman’s foot to see the damage it was doing to him. She could see his penis flexing angrily under the teasing fabric as it rubbed and petted his big boner.

As she did it to him and Kelly stared, she began to speak to her son for the first time in weeks.

“Is this what you like, Thomas? Hmm? Do you like to feel a Lady’s stocking foot rubbing your cock for you? Rubbing it up and down and up and down until you make one of your disgusting messes? Until you squirt you jizz all over her fine hosiery?”

He just groaned loudly like the male cow that he was, as his mother continued her verbal assault.

“Do you like that? Such a big boner you have for my stockings. Perhaps you can jack off on my stockings when we get home. Give me a little show each night. Or perhaps, I can just do this.”

The damp silky foot was just under his balls, flipping them up with little pumps of her toes. He stared up at her face unable to take his eyes away. He was whimpering with the desperate need that made his sac feel so full. His mother saw him looking at her and she looked right back at his reflection, pursing her lips in mock sympathy as she rubbed her foot clad in its hosiery the length of him. The large toe reinforcement had a ridged quality that kept catching on the rim of his cockhead as she pulled her foot forward. Then she would drag the fabric back up until her toes rested under his balls, her reinforced heel resting heavily on his throbbing dickhead.

“Aww, you poor poor baby.” She said mockingly. She was full of false sympathies as she goaded his awful erection toward a numbing ejaculation.

She mashed at his swollen cockhead with her reinforced stockinged toes as if she was stubbing out a cigarette on the pavement. The itchy fabric there teased at the sensitive underside of his dick right at the concentration of nerves that were calculated to produce ejaculation. She twisted her toes in a tight circular motion, putting her full weight into it as he bit his lip and perspiration made his bare skin shine.

“Does Mommy’s little man need to make a mess? Hmm? Is that what this is all about? Go on 3; the ladies would like to see you squirt on Mommy’s stockings. Don’t disappoint them. Make a big mess for me and Ms. Kelly, Thomas. Squirt for me. Do it on my stockings. I don’t want to see a drop go anywhere other than my stockings.”

The slick fabric of her hosiery and the words she was using was having the desired effect. His anus suckled frantically at the buttplug. His stiff, rock-hard penis was quivering under all of that silk and hot foot perspiration. He was bucking his hips slightly like a bitch mare in heat. Stopping her movements on his cock, she paused to decide on the way she would make him ejaculate. The long pause made him wiggle and squirm hoping for more maternal contact despite its cruel and humiliating nature. Then, his mother’s soft foot pushed fully down letting him feel the complicated weave that ran the entire length of her stocking before raising it up again. She used this peddle-pumping motion as if she were trying to start a car. No further encouragement was offered other than the wicked force of her stockinged foot pumping up and down. It was a wicked, teasing sensation and a cruel way for a mother to treat a son’s penis.

With their eyes locked on one another, and her arrogant expression filling his whole world, he came, calling her name.

“ohhh god, mommmm 3;!”

The first squirt was an ugly white smear that coated the bottom of her brown stockinged foot. She smiled in smug satisfaction.

He grunted as his mother’s foot came back down, temporarily damming his flow, then released. Another huge spurt poured out of his cock to land in thick clumps on the floor directly in front of the stool. Kelly began to scold him.

“Oh, you bad, bad boy! Shame on you!” She gave his rump a spank that made his balls jiggle from the impact.

His mother continued her cruel pumping, up and down, letting him release just a little bit of his sperm at each interval. The excersise prolonged his ejaculation into a long drawn out affair that provided a rich spectacle indeed to the women who watched it, as girl-tongues busily lapped their clits. They too were cumming just then. Her son’s ejaculation on her stockinged foot went on for minutes. At its conclusion, she withdrew her foot slowly and held it up to examine the stocking. The brown sole was covered in thick semen and wads of it dripped to the floor. She spread her toes in the hosiery and saw her son’s sperm hung in big slimy webs in between. Then, with an air of smug satisfaction, she slid her spunk covered silk foot back into the high-heeled boot and laced it back up tight.

Isabella came forward with Audrey and the three women hugged.

“Oh, Emily 3; so perfect. You do that to him now. Do that all the time 3; with your stockings.”

Emily smiled like the cat that ate the canary.

“Oh, I think I can keep my son busy for quite some time 3; now that I know what he needs to keep him in line.”

Audrey smiled at Emily and offered her services.

"You know, I would be more than happy to put him to use from time to time. I have lots of hosiery that could use a good sperm bath."

His mother chuckled. Deep in the confines of her sexy little boot, she was wiggling her toes in her semen soaked stockings. It felt positively wonderful.

The three women glanced back toward her poor excuse for a son and watched as Kelly idly pinched at his sack and examined his peehole to see if there was anything left in him. She was scolding him while he did it.

"I cannot believe you would squirt your gross cum all over your mom's stockings like that. My god, you are sooo nasty."

Kelly began spanking his bare bottom, reddening it with open-handed swats.

Emily continued. “And if he has been especially naughty, I can always have Kelly come baby-sit.”

They all had a good laugh at that.