A Momma's Boy

Tom sat in a highchair at the kitchen table dressed only in a T-shirt that had the words "mommy's little helper" scrawled across the front in pink cursive. Roz had made sure he had a clean pair of white cotton panties to wear, and a pair of white gym socks. She had bibbed him, and was feeding him his morning gruel when the phone rang.

"Hello?"

"Oh! Hi Barbara!"

There was a pause in conversation as Barbara blabbed for a good while and then Roz popped a question.

"Listen, I'm having the Ladies from church over today for bridge. Would you like to come?"

"Really?"

"That would be wonderful!"

"Oh, and Barbara... could you do me a little favor?"

"Wear the stockings you wore yesterday."

Her eyes locked directly with Tom's as she said her next words... as if she was speaking entirely to him alone.

"Yes, I know they smell."

"Bye, Barbara."

This was to be the day that Tom was introduced to a form of public milking that he would never forget. The horrible bent jackoff tube was no picnic, but Roz had planned on showing her little son-in-law a new contraption of her design. She called it a Sperm Strangler. It was a fairly simple mechanism composed of metal and steel wires. A metal ring fit securely around the base of both the penis and testicles. Two smooth wires traveled the sides of the penis and ended just under the head in another much tighter ring. The purpose was to actually allow ejaculation to occur, but also to pinch it off just shy of the opening. This would, of course clog the entire penis with hot sperm having nowhere to go. In time, she would remove this retainer and he would actually pee his semen from his penis without the emotional benefit of an orgasm to soften the agony of whatever humiliation Roz intended to impose. She truly looked forward to this afternoon.

Around one o'clock the first guest arrived.

It was Barbara.

She looked beautiful in a high-powered business suit and her lovely gray stockings with the wide dark bands at the top. They were the reinforced toe variety that she favored. She wore smart little white gloves and a matching wide brimmed hat that made her look both fashionable, and in charge.

Barbara Galino was a 48-year-old former trial attorney who had married a rich schmuck who liked to chase after younger women. She had done well in the divorce and stank of money.

She didn't abide perverts well, and believed strongly in the benefits of humiliation to keep them under heel. She was a member of the Ladies Temperance Society of the area, and also believed, like Roz, that some men should be kept shamed and milked.

When She had settled herself and gotten comfortable, Roz called Tom into the room.

He shuffled into the living room, his face beet red. He tugged nervously at the hem of his embarrassing T-shirt to hide the fact that he was wearing panties.

"Over here, Thomas. Right in front of Ms Galino. I want her to meet you."

He stood in front of the attractive Italian woman, who regarded him with amused interest.

She crossed her shapely legs, sliding one gray stockinged leg over the other which caused them to make an audible hissing sound.

"Thomas! Stop pulling on your shirt. You look ridiculous."

He instantly halted his tugging and dropped his head down sheepishly.

Barbara lit a cigarette and looked the younger man over for a bit before she spoke.

"Mommy's little helper... is that who this is in front of me?"

Roz spoke up.

"He's my daughter's husband, Tom. I don't think you two have ever met before."

"A bit of a panty waist, isn't he? I would have thought Stephanie would have married some big handsome man."

She leaned back and exhaled a plume of smoke towards his face. For the first time since he had stood before her, she addressed him directly.

"Are you, Tom?"

"I beg your pardon, Ms. Galino?"

"Are you mommy's little helper?"

He looked slowly from Ms Galino's face over to his mother-in-law's. Barbara followed his eyes and glanced over at her friend.

Roz answered her friend's questioning look.

"He is my little helper... by keeping his panties clean, and by being an obedient little man."

Barbara laughed.

"You mean by keeping his underpants clean?"

Roz reached out and took hold of the hem of Tom's shirt. She lifted it clear up to his chest to expose the girlish white panties he wore.

"My, my, my... such precious little panties tommy. Did Momma pick those out for you to wear? Tom blushed deeper as the doorbell rang again.

Roz went to go answer it and Tom was left staring down at Ms Galino's gray stockinged legs. He thought he could detect a slight odor coming up from her black shoes. His penis began to uncoil in his panties.

The next two women who entered were Marge Sheldon, and Beatrice Green. They were both around Barbara's age and sported attractive outfits similar to what Barbara wore. Roz had them come into the living room to meet her son-in-law. Tom was still standing there foolishly with his panties on full display as the Woman, both rather stern in appearance, took in the sight. He felt mortified beyond belief. The way they looked at him, with his dignity slowly leaving him made the young man shudder slightly.

"Ladies, this is my son-in-law, Tommy. I know he looks silly, but he is being retrained by myself at the insistence of my daughter. Tommy, tell the Ladies why you are being made to wear girls panties today."

"I...I have to wear them because..."

"Panties, Thomas. I have to wear panties. Say it."

"I, um... have to wear panties because Mommy says its punishment for doing bad stuff."

"Thomas, tell the Ladies what kind of bad stuff."

He lowered his eyes to the carpeted floor and his breathing increased with his shame. The women watched him haughtily, not making a sound during his humiliating little confession. His next words were barely a whisper.

"I play with myself and make a mess on my wife's panties."

Roz finished it for him. She spoke loudly, and with authority, ignoring him completely for the moment. "He jacks himself all over my daughters good panties. She was becoming irate. She tried scolding him, lecturing him, even straight out reprimands... finally she brought him to stay with me for awhile."

Marge Sheldon spoke first.

"Have you tried milking him, Roz? That's the only way to teach him a measure of respect while supervising his nastiness."

"Oh, yes. Tommy has been milked. I will milk him continually until he learns that ejaculation for a pervert is without dignity. Decency isn't an option for some men."

All of the women exchanged knowing glances and small chuckles of agreement. Beatrice regarded the young man for a moment and then said "I certainly don't want to seem like a worrywart Roz, but I'm a little uncomfortable with the way he seems to keep looking at my stockings."

"Tommy. Are you getting a boner from looking at Ms Green's stockings?"

Barbara Galino reached out daintily with one white-gloved hand and smoothed it over the front of Tom's panties. She looked up at him and spoke.

"Dirty thoughts, young man?"

Tom couldn't help himself. He began to think he must truly be a pervert. Here he was getting a stiffy in front of a room full of respectfully clothed women. And they all could see the effects of his fetish on his penis.

"So it's hosiery, then, is it?" It was Marge's turn to comment again. "Honestly, some men belong in cages... peeing on newspapers like the dogs they are. It's just shameful the way they behave. Lady's underthings are not tools to help you to soil yourself, young man."

Tom stood there with his hard-on making an embarrassing tent in his panties as the women scolded him.

Roz left the room only to return with her new device.

"I think Thomas needs a good milking to help him remember his place."

Barbara stopped her.

"Wait, Roz. My feet are sore... I could use a foot massage before he's milked."

Her eyes never left his. Dark and brooding they were... with a hint of mirth.

"Tommy. I want you to kneel down in front of me and pull down your panties so I can see your penis. Pull them just under your balls."

He sank to his knees, grateful to be closer to her shoes. Soon his hard dick was exposed for all the women to see.

"Good boy, Tommy. Now, I want you to remove my shoes and I want you to give me a good foot massage..." she paused for effect. "...with your mouth."

He wasn't sure at first if he had heard her right, but the expression on her face told him he had.

He looked down uneasily at the jet black closed toe pumps she wore. They were old things... scuffed from daily use. He was sure they would smell. Slowly he unfastened the strap that covered her foot and held the shoe secured. He grasped the heel and pulled and was rewarded with a slick "schlucking" sound as Barbara Galino's gray stockinged foot slid out of the hot confines of her shoe. The air around him was immediately tainted by the powerful smell of her foot. He stared down at the thick toe reinforcement of her stocking and saw that it actually looked wet. The odor of her stocking foot was almost hypnotic to him, filling his sinuses with its presence. His cock was so hard it was beginning to slap rhythmically up against his stomach.

"Awww... that's sweet, Tommy. Is doggy wagging his little tail for a treat?"

Barbara drew her gray stockinged foot forward and gently slid it back and forth over his hypersensitive balls.

Ms. Green was clearly offended by the sight.

"God, what a pig. His scrotum is so fat it's disgusting."

Barbara chuckled and quickly withdrew her pretty foot.

"Time for dinner, Tommy. Hot and stinky, just for you. I want you to do a very good job. I want my stockings to be clean and spotless after you have licked them."

She reached out with her white-gloved hand and took a firm hold on the back of his head... and pushed down. She pressed his nose to the gray toe reinforcement and wiggled her toes. He groaned pathetically. The women were silent as they watched the spectacle in front of them.

"Stick out your tongue Tommy. I want you to lick my toes through my stockings." Her hosiery was clearly quite worn and the complicated aromas played with his penis like invisible fingers...poking and prodding.

Barbara kept him at it for a full thirty minutes, pausing every now and then to let him swallow whatever filth he managed to suckle off her feet. Throughout the foot worship, his penis got increasingly hard until finally Barbara allowed him to stop. His humiliation, of course, was by no means complete. Roz came forward to take Tom firmly by the ear and drag him to the dining room table.

"Up. Come on. Up onto the table... I want the Ladies to have a clear view of your penis and balls."

When he had mounted the table and positioned himself on hands and knees, Roz pulled down his little panties until they were gathered at his knees. Carefully, she fitted Tom with the awful penis retainer that would choke off all sperm flow, but would leave him vulnerable to intense stimulation.

Once the Women were all seated around the table and served their afternoon tea, Roz began to offer up the milking chores.

"We need a wanker for him. Any volunteers?"

Marge Sheldon spoke first.

"I wouldn't touch his dirty penis if you paid me money."

Next was Beatrice.

"I'll take balls, but I don't want to have to touch his dick."

Barbara had a broad grin on her face.

"Aww, poor Tommy. You're sooo backed up with sperm. Don't worry... I'll play with your little dick until you make a squirty."

Roz seemed satisfied with the arrangements.

"Fine. Barbara, I'll want to give you some grease to help you masturbate him and Beatrice will need some gloves so she won't actually have to touch his balls."

Barbara still had an evil grin on her face. "Wait, Roz... what about stockings? He obviously loves them. How about you get some of your pretty stockings out of the hamper and Bea can roll them up her hands to play with his balls?"

"I suppose that's a good idea." Roz returned in a moment with some rank smelling taupe stockings that she handed to Beatrice. She was a good sport and said nothing as she rolled them up her small hands.

Approximately fifteen minutes later the doorbell rang again. Roz went to answer it. When she opened the door she was somewhat surprised to see Tracy standing there with several of her girlfriends.

"Hi Roz. Is it okay if I introduce Tommy to some of my friends?"

Roz paused for a moment as if to consider it before she spoke.

"Well... he is sort of busy at the moment."

Two of the girls in the group giggled at that.

Shelly, a cute redhead bashfully asked, "can we see?"

Roz relented when she found out all the girls were of legal age, and invited the four of them into her home.

As they rounded the corner they stopped in their tracks. There on the dining room table was Tommy. He was bucking his ass up and down like some kind of pig in heat. Each asscheek was bright red from repeated spanks delivered by Beatrice. His captured penis was bloated to a terrible degree and shined from the grease that layered it. Between his spread legs, the older Italian lady was doing nasty things to his cock, jacking it hard. She forced the fat head to pop abruptly through her tight fist on each upstroke. She was doing it so hard, that audible popping sounds filled the room. His ball sac had been pinched and pulled on repeatedly to the point of looking as cherry red as his bottom. He wasn't talking so much as making perverted animal sounds. When the girls got closer to the table, Jennifer Connelly saw why.

Someone had packed his mouth full of gray stockings.

Tracy took in the full picture and gave her assesment of things so far.

"Ewww... gross!! Don't get too close or he'll mess your clothes."

The girls all laughed but kept their distance.

Marge addressed the girls and explained the situation. "This, young ladies, is what a pervert looks like when he's getting a milking. Tommy needs this. This is for his own good."

Kelly Swanson, the shortest and blondest of the group seemed puzzled. She actually raised her hand to ask a question.

"Yes?"

"Why is he getting a spanking?"

"That's a fair question. Some men, my dear, are mature and responsible lovers. Some, like Tommy here, are selfish and perverted masturbators. Now... boys will be boys... but when they jackoff as a result of their dirty imaginations... it is up to responsible Ladies to do the work their mothers obviously failed to do. And since we are not actually the boy's mother, we are free of taboos to get to the root of the problem."

Barb snickered as she fisted the young man's stiff penis in her greasy hand. "Yeah... ROOT."

Tom let out an agonized groan through his mouthful of stinky hosiery and spread his legs farther apart to allow the woman greater jacking-room.

This made the girls all laugh at him, and some of them pointed and called him dirty names.

His cock and balls felt so handled and subjugated as he was used like a cow in a stable.

His face was as red as his ass... but the worst was yet to come.

As Barbara continued wanking his cock he felt soft, stocking clad fingers tickling his scrotum. His dick flexed angrily in the Woman's hand and he was reward with a slap to his bare butt.

Slowly, the stockinged fingers crept their way back up along his ass crack to his asshole... and tickled him there. He felt like an animal. He was being horribly jacked off in front of all of these women who were watching him so intently. He, of course, could say nothing to defend his dignity, gagged as he was with Ms Galino's dirty stockings. He was already so close to cumming!

Barbara continued to pump him forcefully. She was a tough, no-nonsense masturbator. There was no teasing, no fooling around. Just straightforward cockwanking.

Allison Parker looked thoughtfully at the guy's penis in front of her.

"I never knew that they could be stroked so hard."

Barbara looked over at her little friend.

"He needs to be stroked this hard. It reminds him with every stroke who's in charge here."

Marge Sheldon had been staring hard at the pervert in front of her, as if trying to determine the degree of her own revulsion at his antics. Finally, she abruptly stood and removed her skirt. Tommy stared at the sight, a slight trickle of drool dribbling down his chin. The damnable thing between his legs was being squeezed in the most obscene ways to produce loud dick-slapping noises that echoed throughout the entire room. Barbara had a way of pausing every so often to pinch the spongy head of his penis, and make him groan pitifully.

Marge stepped up onto the table without her skirt on. Her sensible tan stockings had wide opaque tops that hooked onto a utilitarian white garter belt. Tommy couldn't look away. He watched her step carefully over to stand directly in front of his face... and then she slowly turned around until her bottom was in front of him. She had large, womanly hips that caused her big ass to swell outward from her smaller waist. Her peach colored panties were pulled taut by the large cheeks of her butt, and Tommy quickly memorized every subtle detail as he was reminded of his similarly endowed wife.

Behind him, Beatrice chuckled and forced a stocking covered finger up his asshole. He bucked and grunted and made a fool of himself before the women watching him. Up in front, Marge Sheldon had begun to tug slowly at the waistband of her pretty panties... pulling them down an inch at a time. She looked over her shoulder at the young man and smiled smugly at him as her ass came into his view.

"Thomas. I'm going to want you to lick my asshole. I'm going to want you to do a very good job. I may not let you stop for quite a while. I want you to become very accustomed to having your face up a woman's behind. Trust me... in the short time I've known you...I can honestly say that's where it belongs."

All of the girls laughed at him as she said this, and Tommy blushed an even deeper shade of crimson. His face was almost as red as his cock.

As her panties gathered down around her ankles, she gracefully arched her back and reached around with both hands to take a cheek. Spreading them in front of his face, Tommy was treated to the slightly spicy sent of Ms. Sheldon's little brown asshole. The finger up his bottom wiggled in the most tormenting ways as his penis was lathered up in more grease by Barbara's wicked hands.

"mmoooooppphhh...!!" He croaked through his hosiery muzzle. His butt was treated to a sharp spank.

Concerned, Marge looked over to her host.

"Roz, dear? Please take those dirty stockings out of his mouth. He has work to do."

Roz pulled the stockings out of his mouth, and paused to examine them. They were moist with his saliva, but they did seem a good deal cleaner then when they had gone in.

"Are you ready Marge?" She asked.

"Yes. Plug his face in."

Now it was Roz' turn to smirk at the jackoff as she took a firm hold of his hair and forced his face to turn upward... toward it's destination.

"Stick out your tongue!"

He did as told, and was soon sealed against the older woman's big ass. His face was completely engulfed on either side by her large asscheeks and his tongue had burrowed deeply up into her musky anus. Marge savored the moment and then addressed him.

"I hope you realize how stupid you look, Tom. These girls all think so. I think so, too.

Now slide your tongue in and out a bit to make sure I'm nice and clean back there."

The women all shared a nice laugh at that. However, Tommy was near the end of his tether. His angry penis had swollen up as much as his evil retainer would allow, and his big balls were about to blow. Barbara could clearly see it, and she increased her brutal milking strokes.