Truth or Dare

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She was also straight as an arrow, so having a woman down there would do nothing for her.

"Are you close?" Sam gasped in frustration, coming up for air again.

"Hmm, not really? It feels really good though!" Kat replied honestly.

"Fuck!" Sam cursed, and dived back in again, this time grabbing Kat's breasts and roughly caressing her nipples to provide extra stimulation.

"Time is almost up" Jin spoke.

"No, wait! She's almost there!" Sam insisted.

"Ummm, not really..." Kat replied.

Desperate, Sam tried using her fingers. She bent her index and forefinger in a "come hither" motion, and inserted them a little too forcefully into Kat's pussy.

"Ooh! That feels... Nice!" Kat said.

"Yes! Come for me babe!" Sam begged.

Now it was Kat who was slightly worried. Sam was slowly but surely bringing her to an orgasm.

She bit her lip and thought of the game. Her gorgeous breasts were at stake! They were small now, if she lost again, she'd be flat! She loved the attention guys gave her when she went out, she loved never having to pay for drinks, she loved making other girls jealous with her huge assets.

That fear was enough to buy her just a few minutes, and then...

"Times up" Jin saved her.

"No! Just a few more seconds!" Sam wailed.

"Rules are rules" Jin replied, but the changes had already begun.

Sam's boobs, ass, and belly grew, and her bingo wings drooped even further. Her amazonian muscles were now just a memory. Fat now protruded around her labia, completely hiding her womanhood. Her thighs almost rubbed together as she waddled back to her seat and flopped down upon it. Even the wooden legs creaked upon the floor with her weight.

Her tattoos were now just blobs of coloured ink, unrecognisable splotches mostly hidden beneath rolls of flab.

Sam wept as she grasped her now huge breasts. She pulled apart her thick labia, trying to find her clit, and rubbed it roughly.

"You bastard! I can't even masturbate properly anymore" she wailed, blaming Ash for her predicament.

"Hey! You were the one who shrunk my dick!" Ash responded indignantly.

"Quit acting like I'm the bad guy here!".

The gemstone glowed, this time, indicating Anna's turn.

Her eyes flickered in the firelight. Her newfound confidence seemed to be fighting an inner battle with her fear. It won.

"Bet you can't squirt further than me". She spit her words quickly, as if afraid that she would change her mind otherwise.

"Further than her?" Ash wondered what she meant, exactly.

He had heard of girls "squirting" but surely she couldn't squirt as far as he could cum?

At any rate, he had no choice.

Slightly put off by Sam's wailing and futile attempts to masturbate in her chair, Ash grasped his now above average cock.

He coaxed himself to erection, and began to masturbate.

Beside him, Anna sat on the floor and spread her legs. Her pussy glistened with her arousal, and her clit still stood noticeably proud of her labia.

She began rubbing furiously. Her eyes were fixed on the flagstone some distance in front of her as her legs shook with her ministrations.

Ash realised he might be in trouble. He had just regained some semblance of a cock, and even grew a bit, he didn't want to go back to a nub!

He pumped harder, but noticed his erection diminish slightly.

Out of the corner of his eye, he saw Sam's grin return, despite her anguish.

She had given up trying to masturbate, and was watching the show. She shot Ash a look that burned like a dagger through him, but then in an instant, it turned into a smile.

"Whatsa matter hun?" She cackled. "Little ash not up to the task? Afraid a girl can squirt more cum than you can?"

Even her voice sounded different now, almost muffled?

Ash said nothing, and got back to work.

Anna was by now rubbing her sex like a woman possessed, her mouth wide open, not in pleasure, but in sheer effort.

Allowing himself to relax, Ash used Anna's display of pure sexuality to easily get himself hard again.

This time, he concentrated on rubbing just the glans of his penis using his foreskin, this technique always brought him off quickly.

Anna was masturbating so vigorously that even her small breasts shook violently. He pumped himself harder, and harder, imagining himself thrusting into her tight pussy.

Anna groaned, feeling her orgasm approach, and Ash was right behind her.

"Agh!" She shouted and her whole body went rigid. Fluid gushed from her pussy, three feet or more, at least. She squirted twice, then one more little one, before collapsing on the flagstones, exhausted.

"Now that is what you call an orgasm" She moaned.

"You go girl!" Sam shouted, but was soon silenced by a look from Jin.

Ash, thoroughly turned on by Anna's display, prepared for his own performance.

His dick erupted, jets of cum shooting forth from his rod, splashing onto the cold ground below.

He ejaculated four, maybe five good squirts, more than Anna, but quantity wasn't what mattered, it was distance.

Ash couldn't see what the distance was. He waited for Jin to get up to check, but instead, she just looked at the gemstone in front of her.

It glowed purple.

"Damn it! That's not fair, he was standing, that gave him a few feet extra!" Sam cursed.

"Rules are rules" Jin replied tersely.

"What does that mean?" Anna said. "Did I... I mean... Did I lose?"

Ashes dick grew in response, another inch, then still more.

Anna's eyes suddenly widened in fear. "Oh my god I'm naked!" she panicked, and frantically grabbed her clothes and ran behind her chair, trying to cover herself while she dressed.

Ashes dick continued to grow, reaching seven, then eight inches, and finally maxed out at eight and a half.

Ash couldn't believe his luck. It was a monster!

Even as it softened after his orgasm, he could feel the weight of his new member, it was like having an iron rod in his pants.

He turned around to show Kat, and she gasped, in admiration and fear. Could she even handle him now?

Even Jin seemed to raise an eyebrow in appreciation.

Sam fumed, obviously furious.

Once again, the gemstone signaled the next turn. It was Sam.

This was it! This was her chance to win her body back! But... How...

She needed to pick a challenge that she couldn't lose, something noone could best her at...

Better yet, she needed to take that bastard down a size or two...

"I bet you can't give me multiples" she said to Ash.

By now, she hated him.

Even with his monster dick, there is no way he could bring her off once, never mind twice.

She felt the apprehension leave her body, even as he approached her, holding his eight and a half inches in his hands almost like a trophy.

He was a guy. He'd pump and dump into her in five minutes, she wouldn't feel a thing, she told herself.

Ash positioned himself on top of her, and lined up his cock with her sex.

He gently spread the protruding fat in front of her pussy, and slid himself in.

Conscious of his new size, he entered her slowly. He didn't want to hurt Sam, just win this damn game.

"Ugh!" Sam grunted as his first four inches invaded her sex.

Then more, and more of his dick thrust into her.

"Fuck, aren't you in yet?" She said.

"Not yet, nearly there..." He said, and inserted his rod the remaining inch. His full eight and a half inch mast now impaled Sam's most sensitive place, and he slowly began to thrust.

He started gently, teasing her with his size.

Sam responded by grunting in restrained pleasure.

Ash held one of her breasts and caressed it as he slid into her, and then he got serious. He was, after all, on the clock.

He began to piston into her harder, and harder. Her curvy body rolled and her breasts bounced in ways they never had before as Ash's massive cock did its work.

She tried to squeeze her vaginal muscles to bring him off, but she had no strength left within them.

Then she felt it. The unmistakable spark of arousal.

Sam did whatever she could to suppress it.

She thought about her job, she thought about taxes, she thought about old people fucking, but most of all she thought about getting fatter.

None of it was any use.

Ash's dick was big enough now to touch her in places she had never been touched, even with her toys, and unlike a toy, he could respond to her pleasure, move in time with her, and give her more, and more.

Even as she tried to quench the fire in her loins, she knew it was futile.

Her first orgasm bore down on her and she erupted in barely muffled grunts of pleasure.

"Mmmmph. Fuck". She cursed.

"I think that's one". Ash replied.

Sam thought of lying, but a quick glance at the gemstone made her think twice. It would never work, she realised.

"Turn around" Ash said.

With some difficulty, Sam rolled over, and lay on her wrists, her huge ass in the air.

"Good" She thought. "He will never be able to make me cum like this".

Ash reinserted himself, grasped her generous hips, then began to fuck like a jackhammer.

In this position, he could pump harder and longer than any other, and bring her to that elusive second orgasm.

"Fuck!" Sam realised what he was doing, and knew that she only had one chance to save herself: She had to make him cum before she did.

She tried clenching her vaginal muscles again, but every part of her was soft and flabby, and she lacked the strength to clench around Ash's dick.

Then she tried thrusting back into him, matching his movements, but this had the opposite effect, and she felt her arousal build even further.

Finally, she tried all that she could: Vocal encouragement.

"Fuck me!" She called through clenched teeth.

"I'm so close, give it to me!" She yelled.

"Don't hold back, cum inside me!" She roared.

She was trying every last cliched porn phrase she had ever heard in a desperate attempt to get Ash to blow his load.

But unfortunately for her, Ash's stamina had grown along with his cock.

He had never lasted this long before, even after two orgasms. It was true that Sam wasn't as attractive to him as she used to be, but he should still have cum by now.

It was almost like he could control his orgasm, like turning on a tap.

He kept thrusting.

"Oh, oh, I'm so close, cum with me!" Sam lied.

Ash adjusted himself slightly, so that his iron rod was now pistoning against her g-spot.

Soon, her fake moans turned to genuine pants of pleasure.

"Mmmph, no, not again!" Sam grunted.

"Are you close?" She pleaded.

"Mm, a little?" Ash told her the truth.

"Fuck!" Sam replied, feeling her second orgasm approach her like the crest of a wave.

"Oh, Oh fuck... I'm coming again... Unggh!" Sam grunted, and her rotund body shook. Her breasts wobbled like great big bags of jelly as she came, and the sight brought Ash to the precipice of orgasm, but he stopped himself, just in time, and with all the willpower he could muster, he withdrew his dick before he could cum.

The changes this time were more modest. He was over the nine inch mark, certainly, but not by a lot. It was thicker too.

Sam wailed as she felt her own changes. She was now closer to "obese" than she was to "curvy". She tried to cover herself, but her robe no longer fit, so she draped it over her body as best she could.

The gemstone gleamed once more, but Ash already knew it was his turn. This game, like all others, had rules, and he had figured them out.

Ash made his way back to his seat.

"Candidate Ash, your turn once more" Jin spoke.

For a few brief moments, Ash said nothing. He scanned the room. All eyes were on him.

His dick, still huge, still erect, throbbed in anticipation of a pleasure denied.

"I dare you to fuck me". He finally spoke.

He was looking right at Jin.

Her eyes widened slightly, as the other players stared.

"You... You can't do that..." Kat spoke, breathlessly.

Jin remained silent, her gaze consulting the gemstone.

"Do you forfeit?" Ash continued, with a tone reminiscent of Jin's monotony.

"N.. No. I do not forfeit." Jin replied, her voice cracking ever so slightly, like a chink being exposed in her armour.

For the first time that evening, Jin stood from her chair and walked to the center of the floor.

With one fluid movement, she unclasped her robe, letting the thick fabric and gilded lace fall to the floor.

She never took her eyes off of Ash as she undressed.

Even naked, she emanated power, poise, and elegance.

Her body was white as the driven snow, save for the makeup that coated her face. She was thin, but athletic, tall, but not excessively so.

Her features bore an Asian countenance, but Ash couldn't tell for sure. It was as if she was a spectre, not quite real.

She eyed his manhood with well-concealed desire. Wasting no time, or words, she straddled him, one elegant leg on either side of him, standing above his cock as he sat, her glistening sex just inches from his manhood.

Then she lowered himself onto him.

Her lips curled just slightly in pleasure, or pain, Ash couldn't tell, but her eyes remained locked onto him.

Then, when he was fully inside her, she began to move her hips, and then her whole body, impaling herself on his nine inch shaft.

Her sex was the tightest he had ever felt, and she was in complete control.

He wasn't fucking her, she was fucking him.

Ash quickly felt his orgasm build once again, faster this time.

She seemed to smirk triumphantly as Ash began to lose himself within her.

He began to thrust a little, but Jin tightened her legs around him, immobilising him. She was the only one moving now, fucking him, milking him, extracting his seed, and Ash could only enjoy the pleasurable feelings she was granting to him.

He felt his orgasm build, but knew that he didn't need to speak. His eyes told his lover all she needed to know.

She smiled, more obviously now, and clenched her sex tightly around Ash's monster cock.

His eyes closed, and he emptied himself completely into her.

He heard himself moan, but felt as if he was outside of his body, lost in pleasure.

Ash had no idea how many ropes of cum he shot into her, but she took every one. She never broke the connection, or even finished thrusting her pussy onto his dick, until he finally slipped out, completely flaccid and spent, then she unclasped her legs and allowed him to sink back onto the couch.

She was almost like a black widow, claiming a victim.

She picked up her robe, and dressed herself slowly, as she walked back to her chair.

Noone dared to look at her in her nakedness. If they had, they might have seen thin rivulets of Ash's seed streaming down her leg, but even then, it wouldn't have undermined the fear they had of her.

Ash waited for the inevitable.

He had tried to beat the system, he had tried to break the game, and he had failed.

How much would he lose? An inch? Two? Three?

But the changes never happened.

Even while soft, it was obvious that his dick was still a monster.

Jin didn't look any different either, but with her, it was impossible to tell.

"The game has concluded". Jin spoke.

"Some of you have won. Some of you have lost. But the rules are the rules".

""I look forward to seeing you all again next year. If you dare."

"Finally". Jin turned toward the still naked Ash, breathing heavily on the couch, still recovering from his orgasm.

"Welcome to the Order of Persephone Brother Ash".

-

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AnonymousAnonymousabout 1 month ago

Love your writing! Hope we get a follow up to Milked by Matilda as well.

H_RoarkH_Roarkabout 1 month ago

So the real secret to the game is pick an activity where both sides win.

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