A Momma's Boy

"My goodness, tommy! Such a fat little penis you have. I think it will just barely fit in the tube."

Tom's eyes were glued to his mommy's jacking fist... pumping up and down on his bloated cock. His legs were slightly spread and he was humping into it softly in an effort to spit out his horrible sperm. Roz noticed the movement and scolded him.

"Shame on you! Humping onto my hand like a dog does to a Woman's leg! Are you going to do that when you're in the tube?"

Tommy nodded dumbly, unable to lie any longer about his perversions.

"Is that so? And are you going to do it no matter who happens to be watching you do it?"

There was a knock at the door.

Tom was shocked. He stopped his humping instantly.

He watched as Roz got up and walked to the door. Everything seemed to be happening in slow motion... then... She opened it!

"Hi Tracy.", she said warmly.

"I'd shake your hand, but I'm a little greasy." When she said the word "greasy", her eyes gestured over towards the sofa.

Tracy looked down at her hand and saw the smears of lubricant on it. Then, her eyes wandered over to the sofa... where Tom stood. His panties were lowered just under his balls. His cock was a thick, greasy, obscenity bobbing stiffly up and down in front of him. He shuddered as he looked at the pretty mail-girl in the doorway.

"Hi tommy", she said in a long drawn out way that made him feel more childish.

And then, in a hushed voice with her face slightly lowered in a gesture that mocked decorum... her eyes locked on his and she whispered "I can see your pee-nis".

There was a moment of painful silence that followed. Tommy's mother in law and the mail girl looked at him scornfully.

The young man... obviously at his wits end... broke down and began to cry.

The two women tittered at his juvenile display, and with the ice nicely broken, Roz decided to resume her business.

"Come have a seat on the sofa, Tracy. I want you to be able to see everything I do to him."

"Thanks. I wouldn't miss this for anything!"

Tom watched in horrified silence as the two women sauntered over to him to take their places. As Tracy passed by him, his fattened cockhead brushed firmly against her muscular tan thigh. Tracy squealed and looked down at the greasy smear on her leg.

"Ewwwww....!! Shame on you!"

She swatted him hard on his tear-streaked face.

Roz folded her arms across her chest, emphasizing both her displeasure and her large bra- covered tits.

"Thomas... apologize."

It was clearly not a request.

Tom looked down at his bloated dick and mumbled out his embarrassed apology.

He had no idea that his wife's mother could be so cruel... so controlling. He watched as the women seated themselves smugly on the couch in front of him.

Roz explained in great detail what the young man was going to endure for the remainder of the afternoon... all the while her hand lazily jacked his fat greasy cock up and down, up and down. Tracy, her cheeks prettily flushed, couldn't tear her eyes away from the sight.

At last, Roz began to fit Tom's penis into the opening of the tube. For the first time both Tom and Tracy noticed the little leather strap on the bottom of the opening.

"Whats that for"? Tracy said, pointing at it.

"Oh that. That's for naughty little boys that can't keep still for a milking." Roz chuckled.

"His balls get strapped in and he can't pull away... but he feels it every time you pull forward, allowing his thing to straighten out again in the tube. When you push forward, his thing has to bend, but less pressure on his balls. Perverts should suffer during a milking, it keeps them humble."

Tracy laughed out loud. "Oh, that is priceless! I love it!"

Roz lowered her voice and enticingly offered her young friend a treat, "If you want to, you can fasten the strap around his balls".

Tracy was quick to take the leather in her pretty little hands. Thomas shuddered as her fingers came into play just under his heavy scrotum... and his naked anus tensed in apprehension.

"God, if my mom could see me now." Tracy gushed.

Approximately ten minutes later, Tommy was a sight to behold. He stood naked except for his panties, now lowered completely to his knees, in front of two fully dressed giggling women. Well, one giggling woman, and one very serious woman.

He was making horrible animal sounds and flexing his cock as it was thoroughly beaten into obedience by his Mother-in-law's milking tube.

The steady "schluck, schluck, schluck," sounds filled the living room.

Tom's mistreated penis was big and fat from the constant teasing that Tracy put him through. His balls were ripe with the stink of pervert sweat, and added their own wet slapping percussion to the obscene beat of his milking.

"OOOhhhh, Mommy! It hurts my cock when it has to bend like that!"

Roz' hand rocketed down with a hard spank on the boy's bare bottom.

"Little boys do not use that kind of language in this house. If you must, you can refer to it as your 'little thing', or your 'penis', but cock is a disgusting foul thing and I will not have it spoken from you. Am I clear?"

"Yes, Mommy. But it hurts."

"I know. It's supposed to hurt. That's the point, tommy. Your little thing is going to make a great big mess and it's going to hurt."

Tracy was working the tube up and down the pervert's swollen cock. The bend in the tube was fascinating to her. Each time her little hand pushed his dick deep into it's recesses, she was rewarded with another sticky slap of his sac against the plastic and a high pitched squeal from the dork.

"Do you always make him wear panties?" Tracy asked with a smile, while she pumped him.

"Tommy wears panties because he masturbates on women's underwear. This is to remind him that little boys are to keep their panties clean. He's going to be inspected regularly to see if he's keeping his stains off them. And he's going to get a good spanking if I find out he isn't."

Tracy looked up at the guy she was fisting... making vicious eye contact. "You big pervert. Jacking off on panties. Shame on you!"

Her tubing hands never showed any mercy on him as he was milked in horrible, repeated right angles that stretched the tight skin on his stiff boner.

Roz watched the action unfolding before her. She was seeing something taboo. Something that no young man should have done to him while his Mother-in-law watched.

"You know Tracy, he was humping my hand like a dog when I was putting the grease on him earlier."

"I can believe it. If it wasn't for that mean little ball strap, he'd be doing it right now, I'll bet."

Both women laughed again.

"Tommy. Would you like to show Tracy how you hump like a little doggie?"

The way they were speaking to him was getting deep into his head. He felt so ashamed. So inferior. At the same time, his big cock was pounding with lust as it ballooned up into a truly monstrous proportion. Tracy thought it was hilarious. The way the greasy penis had to bend each time she rammed her fist down on him. The big baby was wearing panties that his "mommy" had made him wear, and he was being jerked with a wicked bent milking tube. She was definitely going to tell her Mom all about it.

" Tommy, I asked you a question."

"L... like a dog, Mommy?"

"Tracy. Hold your hand still for a minute. I want him to hump himself into it. It's really quite comical. You'll get a good chuckle out of this."

Roz disappeared for a minute into the bedroom. When she returned she was holding another item in her hand. When she held it up in front of Tom's face, he gasped. It was a 7-inch long evil looking anal plug. Slim enough to work itself in deeply, but plenty thick enough for him to feel the stretch.

"It vibrates Tommy. Deep inside your ass. It's to help you along as you show Tracy how you hump things without Momma's permission."

Tracy laughed so hard at this she rolled backward on the sofa, her socked feet both kicking the pervert in his gigantic cum-filled balls.

"OOOOhhhhhh...", he grunted.

Roz went around behind him and took a firm hold of one of his bare asscheeks. Pulling hard on the cheek, she exposed his naked asshole to her derisive stare.

"Tommy, you really need to clean yourself better."

He was still focused on his tormented scrotum as he felt the hot, gelatinous sperm gurgling around each big testicle. He felt the head of the plug butt up against his bare anus and goad it with soft, knowing jabs. It teased at the entrance to his most private place, before slowly sliding in and up his ass.

"OOOhhhh... god", he whispered, embarrassed beyond belief. The thing had rubbery little ridges that teased his asshole as it sunk in deeply from his Mommy's pushing hand.

"Do you like my socks, Tommy?" Tracy was grinning right at his balls as she said it.

"I hope it didn't hurt too much when I kicked you in the nuts."

The pervert groaned as she dragged her socked foot back and forth between his legs... the complicated weave of the cableknit pattern in her socks teasing his sensitive ball sac. "Does your wife ever kick your icky, hairy balls?"

Roz peeked from behind Tom's ass. "Now there's and idea."

Tracy continued to rub her soft knee socks back and forth between his legs, dragging his scrotum along the fabric. His asshole sucked greedily at the buttplug his Mother-in-law was forcing up his ass, and his angry penis was begging for some kind of release from the indignity. Tracy bent forward and made and "O" shape with her forefinger and thumb that she slipped Tommy's cock into. The young man began to hump almost automatically into this little piece of girlish heaven. His hips pumped hard, forcing his greasy dick in and out... just like a dog fucking a bitch in heat. The room was quiet for a time, save for the sticky jacking sounds of pervert-sex, punctuated by the soft chuckles and giggles of two very amused women.

Tracy was watching Tommy's dickhead with rapt interest, a smile on her face as she stared at it. For the most part, the momma's boy was trying to ignore his two masturbatrixes that had so evilly brought him to this state. It was a hard thing to do. They were handling him so intimately. He knew for sure that he would obey his wife's wishes from now on. He would no longer selfishly jerk himself into her pretty panties. He was a new man... Or so he thought. "Man" didn't quite seem the appropriate word here. "Men" did not wear little girl panties. "Men" didn't have to submit to underpants inspections from their Mother-in-law's. And "Men" most certainly didn't have to suffer the embarrassment of being jacked and milked for the amusement of Ladies. No, only a jackoff boy should be familiar with these torments. This was for the Women... not him. He was merely a toy for their entertainment. His Mommy had worked the entire rubber ass probe into his bottom, and was now activating the vibrating switch. The big stupid thing wedged firmly up his ass began to seethe to life with prostate-punishing rhythms. It was like a second cock up his ass being beat off even as his sweet faced Tracy continued to break down his dignity with her dainty little jacking fingers. His humping slowed, in favor of longer, more embarrassing strokes that he might have saved for more private moments. The way his ass pushed out and his knees bent, and the way he slowly slid his big dong back through Tracy's greased fingers made the women laugh.

"Good lord, that's nasty!" Squealed Tracy.

Roz was watching, truly fascinated. "Hump Thomas. Hump those pretty fingers."

She reached out with both hands and daintily grasped his bare asscheeks firmly.

She looked down and saw the bottom of the black buttplug just peeking out of his widely dilated asshole. His cheeks red with shame, Tommy continued to hump himself into humiliating ejaculation. Roz would simply have none of that.

"Tracy, hon. Fix his penis back into the tube. If he's going to squirt, it should hurt."

"Yes, Ma'am.."

Tracy immediately forced Tommy's bloated cock back into its hellish, bent prison cell. He groaned in agonized frustration as he was so very close to unleashing the burning load in his hairy balls.

Tracy scolded him like a schoolteacher.

"Oh, now you! Let's have none of that whining. Your dirty penis belongs in the tube if you're going to squirt. I know it hurts a little, but just think how good its going to feel when you make your yucky mess."

His cock resumed its terrible bending and greasy sucking sounds in the tight confines of the milking tube. His fat plug up his butt continued its tormenting vibrations deep inside as he was jacked off by the pretty mail girl and his Mommy's tube.

"Oh, Mommy, Ohhhh...!!"

"What's the matter Tommy, are you getting close?"

"Yes, Mommy... I... I'm going to cum soon!"

"No, Tommy. Not 'cum'. You're going to make a mess, soon. Say it."

"Yes, Mommy... I'm going to... going to make a mess soon!"

Tracy laughed at him and he actually felt it. Her genuine laughter was loud and mocking and traveled on the air to assault him against his naked sweating body. He felt it ripple down his nudity to tickle sweetly all around his big greasy ballsac. It was an outrageous affront to what little masculine dignity he might have been retaining.

"Don't hold back a drop, pervert", Roz admonished.

"You need this very badly. You've needed this from the moment I first met you. The audacity of calling yourself a man. The very idea! Shame on you!" Her hand delivered a loud and smarting spank to his right bare asscheek. Will see what kind of a 'man' you are when my ladies bridge group sees you parading around the house in your little panties." She delivered several more loud, punished spanks to his bare bottom. Tracy couldn't help but think he deserved each and every one of them. This was, after all, how mothers punished their naughty little boys.

The torturous load that had been building up inside of his bloated scrotum had long since become hazardous waste. It had reached critical mass and had backed up into his colon to be stirred into a froth by the buzzing demon deep in his butt. His grotesquely stretched penis was being beaten into further submission by the horrible tube and now he was going to make his mess. In front of the two women who were watching and could see everything. Privacy had taken a holiday. This was going to take him to the underside of humiliation... and leave him there. He hated and loved every shameful, tearful moment of it. And then he began to cum.

The first gigantic squirt rocketed forward through his urethra only to meet the temporary resistance of the mocking tube. He screamed like a girl. Then, on the downstroke his penis straightened and unblocked the awful torrent of white-hot semen, which spattered noisily inside the wall of the tube. It slopped down in a massive clot of gelatinous white pudding to land in a burning wad on Tracy's prim kneesock.

"My uniform!", She bellowed.

The next spurt was truly enormous. Tom had never seen anything like it. The force of the pressure was so great that his ass muscles and thigh muscles tensed up like shock treatment patient. It blew the tube off the end of his cock to send a long stream of gooey sperm into the air. It landed in a tangle in Tracy's pretty red hair.

Roz was in a state of extreme excitement as she stared at the perverted spectacle in front of her. All she could do was simply chant. "Dirty... dirty... dirty...dirty", as she watched "her boy" unload before her.

"EEEWWW!!!!" Tracy was beside herself with outrage. She didn't know were to turn next, for each time she moved she was met with a fresh coating of hot, thick pervert-sperm.

Tom stared glassy-eyed as he watched his mess fling itself over table tops and sofa fabric... smearing the curtains and landing in clumps and plump little wads on the carpet... and most of all... soiling Tracy.

When the final pathetic spurts had oozed from his dickhead, Tommy had to be held up by his Mother-in-law. Roz was quite satisfied with the size of the boy's load.

"Good lord, Thomas... what a big sticky mess you made!"

Tracy was livid.

"But he got his fucking gunk all over me! You son of a bitch! I should pound your balls for you, you damn pig!"

"Now, now, Tracy. Tommy isn't exactly a brain surgeon here. He's a jackoff. These boys make their messes indiscriminately, and he just got a little on you is all."

"A little?!! I'm a mess, and... oh gross! I can feel it in my hair!"

The milking tube hung mockingly from Tommy's balls by the leather ball strap. Roz patted him on his bare behind as she unbuckled it from his scrotum. When she did this, one last big disgusting wad of spooge belched out of his penis.

Roz consoled him, like a mother with a newborn who had just wet himself.

"There, there." She cooed.

"Momma will make it all better now."

Tom stared blankly at his fat penis hanging down dumbly between his legs. It was bloated and red like it had been through an old-fashioned clothes wringer. It had a beaten look to it.

Roz went to the bedrooms again and returned with a dog collar and leash. She eased the young man's panties off of his feet and began to fasten her collar to his neck. Once this was done and she was satisfied, she locked her leash to the collar and produced a black leather paddle from her purse.

"Now, Tommy. Dirty little boys who make yucky messes, clean them up."

His eyes shifted from her stern face, to her right hip where she held the paddle.

"Don't make me have to spank you in front of company."

She gave a sharp pull on his leash and he stumbled forward in an undignified heap in front of Tracy. Roz' arm shot out and she pointed sharply with one red painted fingernail at Tracy's semen covered kneesocks.

"Lick."

Apparently he hadn't moved fast enough. A loud stinging spank echoed through the living room as Roz swung her paddle down onto his bare asscheeks.

"Don't make me repeat myself. Lick it up!"

Tracy smiled down at him mockingly for the first time in many minutes.

"Yeah, dickhead. Lick up your gross ball slime!"

She slipped out of her shoes and pushed him down with her hand on the back of his head. His face was smeared in a generous helping of white pervert-cum that had splattered all over her pretty navy blue sock.

There was another spank to his ass... it sounded like a gunshot.

Tom began to lick and swallow in a steady rhythm to avoid his Mother-in-law's stern spanking. He continued to endure her punishment, however until he had finally gotten the last glob clinging to the bottom of the curtains.

Later that evening, with Tracy gone, Roz explained the sleeping arrangements to her new charge.

"Responsible grown-up men sleep in big beds with their wives snuggled up next to them. Perverted little boys don't get to sleep in a real bed."

Tom stared stupidly at the baby's crib in front of him. It had obviously been made in a feminine motif. Pink ribbons adorned the edges and fluffy little stuffed animals could be seen peeking out from under the cute little pink sheets.

Roz went over to the changing pad in the corner and came back with a diaper.

"Its time to get you ready for bed, young man."

Tom started to shift nervously from foot to foot. It was a dance of infantile helplessness.

Approximately twenty-five bare-bottom spanks later, Tom was finally to sleep in his baby crib... diapered and tucked in for the night. His Mother-in-law stood in the doorway, a satisfied smirk on her face as she smoked a cigarette. She watched him sucking on the smelly toe reinforcement of the stocking she had so thoughtfully placed in his crib. She turned out the light and headed off to her bed.

The following day took Tom so deeply into a pit of such sexual shame, that I hesitate about documenting here. However, I am of the opinion that jackoff-boys most certainly do not deserve the benefits of modesty and dignity that decent members of society enjoy. I am sure the more temperate Ladies who might read this would agree.