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Chapter 40
by Vanilla91
Does Jack beg to be his worst enemy's ?
No
"Fuck you, you smelly old slut I will never submit!" Jack roared. He then bit into her arm. Tanya screamed in pain and released her hold . Jack began to scrab at her with his nails and pull Tanya's hair. It wasn't pretty, he was fighting dirty like he was in a cat fight but he had to win, no matter what it took.
They rolled on the floor like this for some time until they were both exhausted. Jack was still scrabbing and pulling hair, until eventually Tanya begged for mercy. Jack could see they were close to her mansion. He placed Tanya in a sleeperhold and knocked her out. He tried to pick her up, but wasn't strong enough so he dragged her the rest of the way.
Jack entered the mansion with his prisoner. He felt so good, finally he had won and now he was going to enjoy his victory and humiliate Tanya. Jack turned his back on Tanya and began victory posing. Tanya slowly awakened. Jack ordered her to kneel before him. He then held out his bicep and told her to worship the arm that beat her. He told her if she did a good job he would use plenty of lube when she becomes his anal slut. Tanya obliged and began licking and worshipping his bicep.
Tanya began squeezing the bicep. Jack was still trash talking her. Tanya kept squeezing and it began to hurt. Jack raised his other arm to stop her, quickly realising he should have tied her up. Tanya grabbed his other arm, and she was now holding both of Jack's wrists.
"Let go bitch or I'll hurt you", protested Jack. It was no use. He held his arms out wide, but Tanya pulled his wrists down together. With amazing speed, Tanya roared, released his wrists, and scooped him up in a bearhug. His feet were off the floor as Tanya leaned backwards, her tits pushing into Jack's chest.
Jack knew he was in trouble and began to beg, "Tanya I'm sorry, you win please, please no more arghhh" Tanya didn't reply she kept squeezing, bucking him up and down like a rag doll. Jack felt a rib crack. Tanya let out an evil laugh and gave Jack a lecture that will haunt him forever. "Welcome to slavery bitch, I gave you chance after chance to submit, but you couldn't accept that I am the boss, you scrabbed me and fought dirty, hahaha. You could have made good money as one of my jobbers, but now you'll be my personal escort, my ****!" She released her grip and Jack dropped to the floor at her feet.
Tanya dragged the injured Jack kicking and screaming along the floor in what was an embarrassing sight. Tanya changed into a purple maxi dress with diamonds stitched onto it. Tanya let out an exhausted sigh, she had just ran 5 miles and delivered a total beatdown. A 46 year old woman with a 26 year old man broken at her feet. She felt so powerful as she held aloft her clenched fist, adorned with expensive jewellery. The diamonds on her dress spelt The Boss and she wore knee high leather boots. She stripped Jack naked then **** him into her sweaty jogging tshirt.
Jack was still struggling. She wrestled him down easily and began rubbing her hands over his torso. Jack felt violated. He never could have dreamed he would be dominated in this way by an older woman. He began to feel weaker. She stuck her tongue into his mouth and dominated his tongue with hers. Then she placed Jack on his hands and knees. Jack could see his predicament in a mirror. She was crouching behind him with his hair in her hand. She pointed out the video cameras that would record this event. She violently slapped Jack's ass.
Jack was filled with regret and face turned bright red with embarrassment. He knew what was coming. He struggled feebly, but she was able to keep him place, and she began to pout her lips and flex her biceps. This really rubbed salt in Jack's wounds. Tanya mocked him that she was a mother of four and she didn't even have to use handcuffs this time. She fixed her huge strap on to her waist . It was encrusted with diamonds and had the female symbol design on it. Jack winced when he saw it.
"Please Ms. McVan, be gentle You've owned me, ....I surrender" Jack grovelled in front of her on his knees, kissing and stroking her dildo.
"It's about time you accepted it. But it's too late honey. I'll be honest, I was scared the way you came into my office, nobody has ever challenged me like that and been so disrespectful. You've done me a huge favour tonight Jack. Nothing can stop me now. I've been looking forward to this, you asked for it bitch!" Tanya sounded so dominant in this victory speech, she was loving every second of this.
Tanya took Jack, she didn't use lube this time. He came over himself multiple times until he was a complete mess. He was then made to suck the dildo that fucked him. She was surprised he didn't protest this part, then she realised some men would never even have survived this long. Tanya felt so good, she felt so powerful. She had destroyed him, just as she said she would from the beginning.
Tanya let Jack stop sucking her filthy dildo. He immediately fell to her feet and began worshipping her boots frantically. Jack was shaking with fear. Tanya was pleased at this as she relaxed on the sofa with a glass of wine. Jack was thanking her for mercy and promising to do whatever she wanted.
Tanya smirked and laughed her evil laugh, "I always win, I'm the great Tanya McVan,.... The BOSS!"
"Yes Ms. McVan I wish I had bowed down before you and sucked your pussy when you gave me the chance in your office. But I chose to fight you and trash talked you. I even did a deal with your daughter to try and bring you down. Now you've beaten me twice and I'm your bitch" said Jack in a pathetic speech, trying to impress her. He knelt down in front of her as she sat on the sofa. She wasn't wearing any underwear. He slowly climbed under her dress so he could rub her ass. Tanya was pleased. She admired the resistance he had put up against her, she was exhausted at this stage. But she had conquered her foe and now he was about to eat her ass without being ordered. He was so afraid but still ashamed as he hated her more than ever and it was disgusting. "Thank you, Ms. McVan........ The.....Boss", Jack whispered. Tanya began laughing she was getting a rush from this powertrip. Jacks tongue was beginning to make her orgasm, adding to her hysteria.
Jack's great plan for **** over his nemesis had ended in the worst way possible. He handed her the ultimate victory and was enslaved. Jack kept licking as Tanya cackled an evil laugh. She was on top of the world.
No one messes with Ms. McVan
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Create a Wrestler
Sex match additon
Create a female or play a male well and fight made up or WWE stars.
Updated on Jan 24, 2025
by Dustyaurora
Created on Jul 3, 2004
by fanficnut
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