A Momma’s Boy


Some men are just born dickheads.

Tom was a 32 year old dickhead… or at least his wife certainly thought so. He had just lost his job of ten years and now he was having trouble pleasing his young better half. It wasn’t the sex… they didn’t do that anymore. It was just that Tom had a bad habit of getting into his wife’s things.

Basically timid in nature, he was a devout masturbator who had somehow wound up married to a gorgeous young woman. Stephanie was the typical “Jewish American Princess” you may have heard about. She was a sweet, perky young woman of 21, who was a born pricktease. She never really had to try… it came naturally.

She had long straight blond hair, and the biggest brown eyes he had ever seen. Small, but firm breasts, that gave her a youthful charm. Her legs were the muscular kind that looked incredible in any kind of hosiery. Her ass was womanly- magnificently sculpted and jutting far outward from her smaller frame. Her fat little ass teased Tom, something fierce. The way it stretched a pair of panties to the maximum. The way it always seemed to stick out prominently when she stood with her weight cocked on one leg… and the way it conspired to pull her panties deeply into the tight crack- teasing any poor fool who was unfortunate enough to look at it directly… like Tom.

Stephanie’s favorite way to lounge around was in her youthful little panties fully displayed to her perverted husband. Stephanie’s ass alone could make a fellow spurt in his pants like a little boy, if he wasn’t careful. It was all very, very wicked to Tom. The last straw occurred when his young wife had actually caught him masturbating himself into a pair of her good panties. The adorable pink ones with the little kitties all over them. He recalled how the little kittens had looked staring up at him from their pink cotton background… covered in a blanket of his hot sticky sperm.

“Please Stephanie, can’t we talk about this?”

“NO.” Was her only reply.

Their car sped along, through suburban neighborhoods with his wife at the wheel.

They were going to visit Stephanie’s mother. Tom had it explained to him the previous night. Stephanie and her mother shared everything… there were no secrets. She was her Mommy’s Angel, and the two would talk for hours nearly every night. Sometimes Tom would use the time as an opportunity to indulge in his favorite dirty habit: jacking off on his wife’s pretty panties. Stephanie had called her mother and told her all about her husband’s dirty habit, and loser lifestyle. She had called him to the phone, interrupting his awful stroking. He quickly pulled up his pants and made his way to the living room where his wife was. She had looked scornfully at his flushed face and his rapid breathing. He remembered how she was dressed- in an oversized T-shirt and a pair of pale peach panties that peeked out teasingly from the hem. She had held the phone receiver out to him, and said ‘momma wants to talk to you.’ Tom had nervously held the phone to his ear, and listened as his Mother-in-law’s proclamations fell on him like a ton of bricks. “Thomas, I am very,very disappointed in you. I think you have been behaving like a dirty, little child, and I think you need to spend some time here… with me, to learn a good lesson.” She had hung up after that.

The car pulled into the driveway and Stephanie turned off the engine. They both sat in silence as the motor cooled.

“Stephanie, honey… I will get a job…”

“Shut up! Tom… just shut up, okay? I am sick of your excuses, sick of your filthy habits. You’re a jackoff!” Tom was silent… she was really mad… and she had called him a jackoff! The word had sounded so dirty coming from her pretty, innocent mouth. Tom’s penis was a heavy club in his pants.

“Mom has a room for you, and your going to stay with her until I hear that you have cleaned up your act. I’ll check on you from time to time, but for now… you will treat her like she is your mother too. Understand?” He had no idea what she was talking about, but new he didn’t want to get himself in any more hot water with his beautiful wife. If this was how they would stay together as a married couple, then he would accommodate her.

“Yes, Stephanie, I understand, but how long…”

“Tom, go into the house, now.”

He nervously shuffled out of the car and up to the steps before casting a longing eye back to the car, his wife, and… as he would soon learn, his last claims to his manhood.

Roz Bernstein was a hard-looking older woman of 46. She carried herself with dignity and power. This was a Woman with whom you would not win an argument. But she was somehow attractive amidst all of her feminine strength. She possessed an almost indefinable sexual prowess that many older women seem to have. The graceful way she moved around, full of confidence and arrogance in the way she swiveled and shook her big ass. The way her dress molded to her incredible figure- emphasizing her womanly maturity instead istanbul escort of hiding it. Tom thought she was incredibly exciting to look at. She was not the stereotypical Jewish mother,however. She was addicted to controlling cock.

Roz opened the door after the second knock and motioned Tom inside after waving goodbye to her daughter. She was on the phone with someone so Tom just stood there in her living room feeling somewhat out of place. He took the opportunity to sneak furtive glances at her. She was dressed in a white blouse, navy skirt, with matching navy blue colored stockings and black pumps. Her short brunette hair was stylishly done, with just a few streaks of silver and gray to lend her a dignified feminine appearance. She was smoking a cigarette as she chatted with one of her many friends. Tom continued to stare at her as he noticed in one of her hands a wad of familiar looking fabric. My god… it was a pair of Stephanie’s panties! They were balled up in one of her hands, the little floral print vaguely crusty from several day’s worth of pathetic self-abuse. He actually felt himself blush fully from his forehead down to his toes. A small droplet of sweat slowly tickled its way down his cheek. Despite this revelation, however, he couldn’t help but notice his attractive Mother in law’s hosiery. Oh, those stockings looked fine, thought Tom. They were the kind he would have loved to jerk off into… if the opportunity ever presented itself. She looked dressed up to go out. Maybe… maybe she would leave him here to wait- with her stockings. He hoped they had a toe reinforcement… he loved to feel the reinforced nylon clutching at his swollen cockhead.

Tom’s self-indulgent thoughts of perversion where abruptly cut short when his mother-in-law spoke. “…well… at the moment he seems to be looking at my stockings.” The words made Tom blush bright red and he quickly looked down at the floor in embarrassment. His mother in law chuckled. “…yep. Just another little boy trying to hide his dirty thoughts. …okay Barb, you enjoy your time off. Gotta run. Bye.” She hung up the phone and walked over to stand in front of Tom.

“Thomas. What were you thinking about when you were looking at my hosiery?” The young man couldn’t meet the older woman’s gaze, for he somehow anticipated the knowing smirk he would find there. “I… I… I wasn’t thinking about anything. Just waiting for you to finish your call.”

She extended two finely lacquered fingernails to grasp him by the chin and raise his eyes to hers. The smirk was there, just as he had feared. “Thomas. Were you thinking dirty things about my stockings? Things involving your penis?” He shuddered at the way she spoke to him… down to him. And the way she called attention to his penis made him feel small. For some dark, unknown reason… he felt himself growing hard between his legs. As if tugged by some unseen force, Roz’ eyes were drawn down to the crotch of his trousers… and the little lump forming there. She cocked one eyebrow as she studied it with arch disdain. “Thomas… I want you to remove your pants for me.”

He froze for a moment then shyly undid his belt and zipper… fumbled with the clasp on his trousers… and then slid his pants down his hairy legs. His arousal was cut short by his mother-in-law’s genuine hearty laughter. “Ohh, Thomas! What an adorable pair of underpants! I just love those little boy white jockeys! Did my Stephanie pick those out for you… or was it your mother?” He had never thought of his underpants as being “little boy” before, but suddenly he felt very childish and ashamed as he stood there in front of his new governess, fully dressed as she was.

“Hurry up… remove your pants, and hand them to me.” Tom felt so foolish as he handed over his pants to his mother-in- law. She took them possessively into her hand and tossed them into a paper bag next to the sofa. “My, my, my… what a big boner.”, she crooned, her voice dripping with mock sympathy. Her elegant hand reached out and caressed his aching hardon through his white Hanes briefs. Tom shuddered at the contact and his mother-in-law chuckled at the display. Then the kindness left her and her hardness was back. “You should be ashamed of yourself, Thomas. I mean… a boy your age playing with himself.” He started to say something, but she shushed him. She brought the panties up from her other hand. The panties she had been clutching in her fist. Exhibit A. Her daughter’s pretty flowered panties, soiled from his juvenile masturbation. She held them up in both hands. Allowing the once pretty fabric to dangle accusingly before his terrified face. “Stephanie has told me that you masturbate into her panties.” He recoiled at her use of the word, as if she had just slapped him across the face. “I think that’s perfectly disgusting. A filthy, disgusting, childish habit. We’re going to train you to learn that.” Tom looked at the panties she held in front of him. He could see avcılar escort dried smears of his dork cream all over the pretty flowers. “From now on, when you are in my house, you are not allowed to wear pants. Is that clear?” “Please… Roz….” She cut him off by holding her hand up. “I don’t care much for perverts and I don’t know of any Women who do. If you are to spend time in my home, you will be subject to frequent underpants inspections.” She paused to let the words hang in the air. The effect was a thrilling wave of shame that seemed to wash over the young man. Roz took note that his penis was actually throbbing now in his briefs. “The second rule is that you will address me with respect. I know you think you are a big boy now that you are married to my daughter, but she has indicated to me that in addition to still leaving brown marks and other childish stains in your underpants, that your efforts as a husband are pitifully inadequate. As your caretaker now, and your disciplinarian, I will expect that you acknowledge my authority over your bad behavior, Thomas. So, you will call me Mommy… and I don’t care who happens to be around to hear it. Understand?” Tom stood there absorbing her words… his cock dancing in his little briefs. What had she said? His DISCIPLINARIAN?? He stared at her for a moment before realizing she was waiting for an answer.

He swallowed nervously, and spoke.


“Yes what, Thomas?”

“Yes, Mommy.”

“Good boy.”

He shuddered at her words. He felt so stupid and embarrassed to be standing there with a hardon. And she could clearly see it throbbing with everything that she said to him. Roz took a seat on a straight backed chair in her living room and beckoned her son-in-law to come over to her. He shuffled over and she took him by the wrist forcing him to take a seat on her maternal lap.

“Now, Thomas. I want you to answer some questions for me, and I expect complete honesty when you answer, or I will pull down your underpants and give you a spanking, do you understand?” His face grew bright red.

“Yes, Mommy. I understand.”

“Good. Now, how often do you play with yourself?”

“well… I… um…”

“Thomas. You will answer me, or I will spank your bare bottom until you can’t sit down for a week! Answer the question!”

“e…every day.”

“What? Speak up Thomas, and speak in complete sentences.”

“I play with myself about three times a day, Mommy.”

“Filthy! Shame on you!” Her rebuke was harsh and full of venom. “You pull on your dirty little penis and make your little messes for my daughter to find, and then you expect to be treated like a man?”

Tom turned a much darker shade of crimson and he thought he might faint from the indignity of it all. She knew! His wife had told her mother EVERYTHING!

“Don’t you, tommy!” She was demanding an answer.

“Y…yes, mommy… I play with myself and leave my messes for Stephanie to find.”

“Thomas. You should be ashamed of yourself. From now on, I want you to refer to my daughter as Ms. Stephanie. I am not comfortable with a masturbating young man referring to a woman in such an informal way. You are already a disgrace… I expect at least some level of manners. We will be working quite a bit on your manners, in fact.

“Come on, little boy. Off momma’s lap.” She was laying it on thick. The condescension was dripping in her voice.

Tom slipped off the warm comfort of his “mommy’s” lap as she got up and took him firmly by the ear. He blushed as much from the humiliation as from the pain of her grip. She led him through the hallway to the rear of the house and opened a door.

“This was my Stephanie’s room when she was a little girl. It will be your room now.”

The room was typical of a little girl’s room. Pink was the primary color theme here. The requisite stuffed animals adorned a floral print bedspread and there were cute animal print panties peaking from a white dresser drawer in the corner.

“Tommy. I want you to be dressed properly for me and any guests that I choose to have.”

“G…guests, Mommy?”

“Yes. I like to entertain my ladies bridge group at my house on Thursdays and I don’t expect to have a dirty little boy running around and getting underfoot… unless he is at least respectfully attired.”

Again, his eyes were drawn to the pretty little panties sticking out of the dresser drawer. Little girl’s panties… surely she didn’t mean…

“You’re looking at my daughter’s panties. I’ll bet you’re thinking about masturbating on them, aren’t you?” He swallowed his dignity with a gulp and nodded silently. Roz shook her head in disbelief. This was too much! She fully intended on breaking this pervert of his filthy habits.

“Put them on.”


SMACK! Her hand left a red print on the side of his cheek.

“You heard me well enough. Don’t make me have to repeat myself. Put those panties on yourself and then stand in şirinevler escort front of me and let me have a look at you.”

“But those are for little girls… I…”

Roz fixed a mean glare at Tom, pointed one lacqured fingernail at the white dresser and tapped a high heel against the floor.

“Those… are for little girls, and perverts!


Tom could see that he really didn’t have much choice at this point. “Y… yes, Mommy.”

He dutifully retrieved the humiliating garment. Once, an agonizing fetish artifact, now the instrument of his emasculation, he held the little panties in front of this older Woman.

He removed his underpants and handed them over to his new governess. His penis was horribly stiff and the cords and veins stuck out in stark relief against the drum-tight skin. He was terribly aware of his bare scrotum and the heaviness he felt in his balls… the way they swayed and shifted with his every movement. Roz stared directly at his penis, a horrified expression on her dignified face.

“tommy… step into your little panties now… for Momma.”

Her words rippled down his spine and tickled his naked anus. He could actually feel it pulsing, forcing more of his thick lust into his bloated penis. It was a shameful display for a grown man to make in front of a Lady.

He stepped into the girl’s panties and pulled them up his legs.

“That’s right.” Roz cooed at him. At the last minute she seized his penis. Her fingers actually pulled slightly at the bare skin along the underside of it. She took the waistband in her other fingers and forcing his aching cock downward, she let the waistband go with a little snap.

“Charming.” She said, sarcastically.

“Tommy, I want you to understand that I really have no intention of putting a halt to your dirty habit. I just want you to understand fully, that you will suffer because of it.”


His throat was dry and he was acutely aware of the soft cotton fabric of the panties on his balls.

“Yes, little boy. You will be taking a ride on the “L” in a moment. I created it myself, you know.” Roz was obviously a little smug about her invention. It made Tom croak softly in his throat.

She left the room only to return a moment later with something in her hand. She held it up for him to see… relishing his reaction.

The “L” was a clear plastic tube shaped just like the letter for which it was named. The plastic was thick and unforgiving… but allowed an unobstructed view of the interior.

“Your penis goes in there”, she pointed to the round opening.

“It slides up and down on you after you are greased properly, and the bend in the middle forces your thing to bend in half with each stroke. It ought to be very painful to be milked this way, thomas. And I hope it does…. Very much.”

Tom couldn’t tear his eyes away from it.

“You were looking at my stockings earlier… do you need to be milked now?”

“n…no, Ma’am. I don’t think so.” He sounded pitiful, and the lump in his panties betrayed his words.

“I don’t think your telling Mommy the truth, now are you?”

Tom blushed and looked down at her gorgeous stockinged legs. She abruptly took him again by the ear and led him into the living room. Roz took a seat on the sofa near the big picture window and instructed him to stand in front of her.

From a drawer nearby she produced a leather strap. Tracy would be coming by soon to deliver her mail, and she didn’t want her charge trying to cover up.

With his hands securely bound, tom felt like a class A wimp. Standing in front of his fully dressed Mother in law, wearing only his panties, hands bound behind his back, about to be milked by her with that awful thing.

Roz paused to savor the moment. The power she felt over his penis was increasing and making her perspire slightly. She removed her shoes from her feet to allow them to air.

Tom’s nose twitched as he involuntarily inhaled the rich aroma of shoe leather and stockinged feet. His cock throbbed between his legs making an obscene tent in the front of his panties.

“Well, well, well. For the little boy that doesn’t want a milking… I believe you need one.”

Tom gulped and nodded, embarrassed. He couldn’t take anymore. He had to cum very badly now.

Tracy Hoffman was a bright-eyed redhead with a killer smile. She had been delivering mail to this neighborhood for about two years now. At 23 years of age, she was in excellent shape from the hours of walking she did. Her uniform looked liked something out of a Japanese fetish movie. The tight fitting navy shorts that put her tan legs on display… and the matching navy blue knee socks were pervert killers to the right man. Her hair, was pulled back in a pony tail and her little postal cap gave her a look of girlish authority. Many men up and down Maple Street silently jerked themselves… hidden behind their curtains as they watched her walk sexily up to their houses and deliver their mail. Roz had formed a lovely friendship with Tracy. The older woman had sensed a delightful playfulness in the girl that she planned to introduce to her little son in law.

In the house, tommy’s penis was being slathered with a heavy layer of greasy lubricant to prepare him for his “ride on the L”.

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