I have enjoyed writing the stories in this series and thank you all for the feedback, positive or otherwise. Feedback, as so many other authors have said, is what makes it so fun to write and post stories. So please keep it comming. All characters in this story are fictionalized and are intended to be of legal age. Please enjoy and tell me what you think.
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… 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… 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… 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… 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… oh god… my clit you little bitch… oh… oh…. Uh… 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 diyarbakır escort 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… you know… 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… 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… 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… 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… 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… 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… 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 düzce escort 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… 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… 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… 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… 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… 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… 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… 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… 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.
“Yes… yes, I see.”
“Do you see how hard it’s gotten just from having you touch his ass?”
“Yes. His penis…um…his cock… its very hard.”
“You know… 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… all soft and silky in there.”
Just edirne escort 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… 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… 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.”