Maggie Flynn was one of the first modern women. She was what was commonly termed a “flapper” back in 1920’s New York City. She didn’t want to be like those “bluenoses” uptown. She wore her blonde hair short, her skirts above the knees and she was known to dance the Lindy Hop until the early hours of the morning.
Her real name was Margaret, but she had been dubbed Maggie by the wealthy men she regularly cavorted with. She was their baby vamp and they all became quickly transfixed by her petite frame as she moved it around wildly in front of them on the dance floor. Afterwards they would pull her sweaty body into their arms and plant kisses on her cherubic face as she laughed and threw her arms in the air.
“Yowser! Yowser! Yowser!” she’d scream out.
She was a blithe spirit and completely in line with the times. She played with these men mostly, and had sex with a few when she was tipsy enough. During those occasions they would bring her back to their Park Avenue frolic pads and pull the same old ass-grabbing moves on her. But she would surprise them at that point by slapping them across the face.
“Fresh guy, ay!” she would charge.
The men were usually taken aback momentarily until she reached down and started unbuckling their pants. After this she’d take down their zippers and pull their trousers to the floor. Then she would walk away and take a seat on the bed. After bouncing on it for a while she’d call them over with her finger.
“No, no! Leave them on.” she’d tell them when they tried to take their pants all the way off, “You can do it! Just shuffle.”
And as they walked to her with their drawers around their ankles she would know she had them. Then when they arrived she’d order them to lay across her knees like bad school boys.
“Now let me show you what happens to men who grab women’s behinds!” she’d say before delivering the first hard smack to their posteriors.
She found they all loved this treatment as she turned their high society, pale white asses, bright red. It was the perfect foreplay for what was to come next because soon she’d have them on the bed with their faces down as she rubbed her silk underwear encased tits along their backs.
“Just a sec!” she’d tell them before getting up and returning with some items from her purse.
The next thing they felt was oil being rubbed onto their butt cheeks.
“This’ll make it feel better.” she’d assure them.
But then she would rub it further down until her fingers were moving over their anal parts. After this she’d push a finger inside of them and get a moan of excitement.
“You like that?!” she’d ask.
She understood the decadent tastes of these rich men, but even they were surprised izmir escort when, after a few minutes passed, they felt the pressure of a cylinder-like object being planted into their rectums. She loved this part as she watched their eyes open wide. They never suspected a thing as she attached the big dildo to her body and then layed down on top of them. She moved into their asses with mastery and always felt she was claiming something from them that she wanted; a feeling of ownership. She would slow fuck them like this for half an hour until their cocks were swollen purple. Then she would turn them on their sides while still inside them and reach around and finish them with her hand. After this experience these men didn’t want sex any other way and she got lots of favors from them.
But one night she met this Wall Street big shot by the name of Bill Maddux who was sure he was the monkey’s eyebrows, and he proceeded to get her drunker than she had ever been before. Or had he put something in her drink? She didn’t even remember the ride back to his place, but she did remember what he did to her after that. He ripped off her clothes at his door and forced his cock into her mouth.
“I’ve heard about you!” he told her as he held her head in place with both hands.
Maggie gagged and did her best not to taste his thick, salty dick as it grew big quickly inside her mouth. When it had reached its full length he grabbed her by the hair and threw her across the room. Dizzily she picked up a figurine from the coffee table and flung it at him, but finally he got her down on the floor and pushed himself into her. She dug her fingers into his face, but that only seemed to excite him all the more.
“I like it rough, too!” he said before pulling his dick out of her and spewing his load all over her stomach. Maggie had to fight the urge to vomit.
Afterwards he tossed several hundred dollar bills in her lap as she sat in a chair rubbing her head.
“Thanks, Sweets! Let’s do this again sometime!” he quipped.
This experience brought all the pain of Maggie’s childhood on the Lower East Side back to her. But she decided then that she wasn’t going to let any man take her down again. Not even Bill Maddux. She would find a way to ruin him, one way or another.
A week later she saw him at a different speakeasy and walked right up to him with a big smile.
“Hi Billy boy! Funny meeting you at this blind pig.” she blustered.
Maddux was stunned for a moment. Then he recovered his arrogance.
“Hey Toots!” he replied, “You back for more?!”
“You bet! Can’t keep me away from this coffin varnish!” Maggie said as she held up her glass of antalya escort booze.
He didn’t try to get her drunk that evening. He got her out the door as quickly as he could to bring her back to his high rent raping ground. But Maggie had some knockout tablets with her that she put in his champagne just before he drank it. Soon he was stumbling and slurring his words. Then he fell back on the couch and reeled.
“Wow Bill, you’re a bit of a lightweight when it comes to the bubbly!” she waxed sardonically.
In a few minutes she had his clothes off and his body rolled over into position.
“That’s my boy! Put that face right down in the cushion!” she instructed.
Then she stripped her dress off and then her underwear. It didn’t take her long to tightened the straps and connect the large black phallus to the pubic plate of her ass weapon. She stood over him when she was done, her round backside projected out strongly as was the nine inch dildo.
“I know you’ve heard about me, Mr. Maddux, but now you’re going to get the full experience!” she announced before moving back behind him to his propped up ass.
She took the phallus into her palm and looked down into his nether region.
“Phew! Doesn’t smell too good down there, Bill!”
Her entry into him was rough and she sneered as she pushed it in down to the hilt. Such was the suddenness of the entry that even in his drugged condition Maddux let out a cry of pain.
“Ahhhh!” he gasped.
“Complaining already, Billy?! The party is just beginning!”
She pulled it out halfway, and then plumbed deeper. She was even able to watch herself in a large wall mirror as her small, graceful body worked over this big, disgusting man.
“Uhhhhh! What is this?” he muttered groggily.
“This is Billy’s comeuppance! Yowser!” she cried out blissfully as she pushed it in again.
Seeing Maddux grimace made the blood rush to her head suddenly. Her breathing became loud as her clit grew bigger with each thrust. One of the takers of this city was this time being taken! Now she knew how he felt when he made all his killings on Wall Street! She pumped harder as her mind expanded. Her father had been a taker, too. All the nights he’d come home drunk and climbed into her bed…
This memory spurred her on. She went at him with savage intent now.
“How does that feel, Billy?!” she hissed as her pretty features twisted.
She could see the lights of much of the city from his 20th floor window. And they were all shining for her now! Little Maggie Flynn was a top dog!
Her mind purred with satisfaction as she began to come back to earth. After this she withdrew kayseri escort her fuck toy from him and left a note thanking him for a good time.
But she wasn’t done with Bill Maddux yet. She searched him out days later and convinced him she’d give him the best orgasm of his life if he let her have her way with him one more time.
“What’s the matter, Billy? You’re not SCARED?” she challenged.
That night she put her big, evil penetrator in his ass again and took him to paradise with her hand afterwards. He groaned for ten or fifteen minutes as cum continued to be pumped from his testicles in short dribbles.
“Jesus! I never… knew it could be… this good!” he whimpered.
This was when Maggie knew she had indoctrinated another ass slave, but she wasn’t done yet. Over the next few weeks she delayed Maddux’s orgasms longer and longer until finally she didn’t allow him to cum at all. The next step was to train him to have orgasms only by having his prostate stimulated. This was a harder thing to do, but crucial to her plan. However, after one failed attempt, Maddux became impatient.
“Come on! Just jerk me off with your hand for god’s sake!” he protested.
“No Billy, don’t you remember, you can’t cum like that anymore. Keep concentrating!”
And after two more tries on separate nights and a lot of labor on Maggie’s part, it happened. She was able to find his spot and talk him through it.
“Does momma have little Billy’s ass now?” she teased as she saw Maddux’s body was beginning to shutter.
She drove it in a few more times in the same direction. After that he started to quake violently and a long, quivering moan rose up from deep in his body. Maggie held her womanizer firmly in place and craned her neck, watching victoriously as clear fluid spurted out of his limp dick followed by a short ejaculation of semen. Maggie knew he was changed forever now because these anal climaxes were the most intense a man could have since they affected the entire body just like vaginal orgasms.
“Ohhh!” he cried out in a voice that sounded like a weakened hospice patient.
And so Maggie succeeded in turned Maddux into an ass fuck squirter. This meant he would never want a dick climax again since they were grossly inferior. And he would no longer be able to have straight sex as a man. As a consequence of this he would father no more children and the world would be saved from his ugly genes. His days as a flapper raper were done as well. He wouldn’t even be able to masturbate like a man anymore. Maddux, from this point on, for all intents and purposes, would be a woman.
Maddux was not the last man Maggie virtually castrated and feminized, but he was the one she took the most satisfaction in. She ended up having quite a pen of fem boys whom she made shave their bodies clean below the waist and go around wearing women’s underwear. And every time they signed another piece of their estates over to her, she would thank them and say,
“Is my little ass whore ready for her man wrecker?”