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It was a simple problem. Big Mac wanted to extend the apple family farm, but that meant buying it from the town. The Mayor, meanwhile, had her own plans for the land. He'd gone to the office to discuss the issue, see if he could talk the stubborn older woman into just letting him do as he wanted, but she had shut him down. She was the mayor of Ponyville, after all, and whatever arguments he could make for why she SHOULD just grant him more land, the fact remained that it was up to her whether or not she would. Sooner or later, he would need her signature on the papers, and she seemed determined not to give it to him, at least at first.

Then she had made him an offer. Or perhaps the better word was "challenge". She had every legal right to block his expansion if she wanted, and right now, she wanted. He didn't have a leg to stand on... So she gave him the chance to take a stand with a different part of his body. She wasn't going to just roll over and give him what he wanted, but she was happy to give him the chance to try to take it from her. His arguments meant nothing, so she would have to dismiss him. Or give him the chance to, as she liked to call it, 'table the issue.' In other words, drop the discussion, get on her back on the table, and let him try with all he had to make her acquiesce.

She didn't give him much time to think, either, as she stripped down, and revealed her gorgeous body, lined with impressive muscles. Inside and out, in fact, as she demonstrated by reaching down and spreading her pussy lips, showing him the lovely tunnel of clutching muscles inside, and slowly rolling them, displaying to the handsome stud exactly what she could do when she wanted to.

"Come on, now, Mac," she taunted him, fluttering her lower lips, "We can do it my way, or... Well, we can do it my way. Just a matter of what type of 'My way' we're going with," she chuckled, "I don't like to lose, Mac, and turning that over without a fight is losing. You're going to have to 'cum' to the table sooner or later."

It was an offer no red-blooded (or red-coated) stallion could turn down, but she sealed the deal as she pulled her fingers from her lower lips, and let them spread wide, certainly wide enough to accommodate his cock, "Are you ready to..." She chuckled, and the motion was reflected in her inner tunnel, "Negotiate~?"

He let his own clothes fall to the floor, scarcely able to remember stripping them down, and stepped forward, driving himself deep inside her in one thrust. Damn, tight was hardly even the right word for it. Not that he had much time to think about what the right word was, he was too busy grabbing her and pounding her, his hips mashing up against hers, pumping and grinding like a wild beast into her body. She gave low gasps with every thrust of his shaft through the tight and textured tunnel of her pussy, and she started to thrust back, her hips mashing to his, turning his blitz attack into a battle of attrition against her pussy.

He had thought he was ready for these 'negotiations.' He had been wrong. It wasn't the sort of thing one could easily be ready for. She may have been older than him, but age had not loosened her lower muscles. She kept in shape, and soon, the war of attrition turned against him. Her counter-thrusts started to take their toll on his stamina, her mighty inner muscles wearing down his assault. He was a mighty stud, always has been, always the envy of men and a top prize for women. Every mare in Ponyville had been eager to just feel him inside her, worship his mighty cock with her mouth and pussy.

Not this mare, though. Not this time. For the first time in his life, he was finding himself locked tight in a pussy that didn't want to honor his cock, but overwhelm it. His breath started to come faster, and yet weaker. His thrusts came with less power, while hers continued at full force. Soon he was simply trying to fight off her hip-thrusts, even while his shaft cock twitched every time he forced himself in to the hilt. His opponent - Or, as he was starting to realize, his superior - Just continued to look up at him with the same confident smile on her face. He hated to admit it, but he was going to need to get out of her, before she pulled his cum out and humiliated him in sex as well as negotiations. It would be bad enough to have to go back and admit to his sister he failed... He didn't want to have to tell her he simply hadn't been man enough to succeed.

Mac tried to withdraw his cock from her clenching tunnel... Only to feel the Mayor's calf wrap around his hips, and draw him back in. In an instant, he fell forward, hands on her desk, groaning and gasping as her pussy squeezed and pulsed along his cock. His breath caught in his chest, and he felt his heart simply pounding. She was a clutching, pleasurable vortex over his shaft, and he wasn't going to be able to make it at this rate. With every muscle shaking, sweat dripping off his body, eyes screwed shut tight, he let out a low whimper as he fought to keep his cum... He could lose the land negotiation, but to lose his cum as well, be milked like this... He gasped, muscles locked too tight in the battle against orgasm to try to pull out. "P-please" he groaned.

The mayor just shook her head. "Sorry, big guy. Can't let you do that."

He whimpered "Wh-why..."

"Like I said, I hate to lose~" She laughed. Her pussy went into what seemed like total overdrive, and his cock simply blasted in her. Seed began to pump out of him, his balls clutching up and forcing more out than he had thought possible... That cunt was chewing him up and eating him (metaphorically) alive. Her inner muscles were hell on his shaft, and tears and sweat dripped off his body as her pussy crushed his cock and his spirit alike. A long gasping groan came from his throat as she drew the seed out with deft twitches and squeezes, pulling the cum out of the helpless stud atop her.

"Ahhhnngggghhhhhh~" He moaned as he felt his shaft continue to surrender, spurting out seed, giving it freely to the gorgeous woman beneath him. Powerful stud that he was, he hadn't been as powerful as her pussy, not even close. In the face of her clutching, clenching cunny, he had been emptied like a foal. Not that she had even an ounce of mercy for the outmatched man as she pushed her hips back against him, and slowly twisted and grinded against him. He could barely support himself on his arms as the mighty mare drew out his seed, seemingly unwilling to allow him to stop until she had completely crushed his pride.

"Oh fuck, please, I can't take it." He moaned.

"I know you can't," she laughed, as her calf tensed and she forced him even deeper in, "Mmm, you're just not man enough for the mighty mayor." She laughed, and clutched tighter with her mighty marehood, bringing his orgasm to a stop, but not how he wanted... Instead ending it by simply squeezing too tight for the cum to continue to shoot. "I love luring guys into these contests... Nothing like crushing your sense of self-worth and pride as well as your manhoods. So much more fun than just turning you down." She laughed, and the vibrations squeezed down on his cock, making both it and him shake.

"I bet I could get you to turn the whole farm over to my like this, couldn't I?" She asked, but the moaning man couldn't answer.

"Couldn't I?" She repeated, and pulsed her pussy again, the mighty muscles suddenly squeezing along his cock, driving him mad with excitement. His cock burst, his back arched, and he immediately began spraying his creamy seed into her again.

The pleasure was mind-shattering, and he gasped out "Y-yes Mayor! Yes Mayor!"

She clamped her cunt down on him again, putting a stop to the orgasm. The helpless man groaned, doubled over her, tears and sweat staining his cheeks.

"Guess you're lucky I only want to knock you out, aren't you?" She laughed. Mac didn't want to risk being subjected to that torment again.

"Yes mayor..."

"Say thank you..."

"Th-thank you..." He groaned, just wishing she'd get on with it.

"Oh no," she laughed, "Not me. Thank my pussy for what it's going to do to you~"

He moaned, but did as she asked. "Th-thank you... Pussy..."

"For?"

"F-for what you're going to do..." He groaned.

"Which is?"

"Kn-knock me out."

"Whyyyy?"

"B-because..." He started, "Because I'm... Not worthy?"

"Good thinking." She patted his cheek "Now say it all together."

Whatever pride he had had to resist her completely vanished, and he moaned it all out "Aghhh... Th-thank you pussy for knocking me out I was never worthy of being in you in the first plaaaaaaaace~" He groaned, and his cock blasted into her... Blast after blast of thick cream poured into her cunt, filling her up and then starting to overflow out of her, back the other way. He simply shook as he came, as his shaft poured out complete submission to the mighty woman beneath him. His eyes rolled back, and he could no longer think of anything. Not the negotiation, not the contest, nothing... Nothing but the awesome pleasure of pumping his balls out, until the whole world went white.

He woke up on the floor of the mayor's office, his hips sticky with his own seed. His shaft, despite all it had been through, still swelled at the thought of what the gorgeous woman had put him through. He outright moaned at the thought, and his shaft stiffened at the memory of how her pussy had seemingly suckled and slurped at his cock until it took all he had - Including his pride. Blinking dried sweat and tears from his eyes, he saw a note on the floor next to him.

"Macintosh,

I think I have made my point rather effectively, but there is more I wish to discuss. We will resume negotiations tomorrow at 8 AM. Bring a friend.

Kindly,

Mayor Mare"

He shuddered to read it, and two things hit home. One, that he could never keep up with her. And two: That he would DEFINITELY be there.