Slut-Box Challenge; Cougar town

A story inspired by the always amazing @Miss Evie Hyde

Jason knew all about the slut box challenge, everyone at his college did, and there was no doubt in his mind that it was the best thing ever. He was pretty sceptical about the idea that it was genuine magic but the way half the girls on campus had suddenly switched from jeans and trainers to fuck me pumps and miniskirts made it seem magical to him. The only problem, as far as he could see, was that none of the eager new hussies about town had chosen him to fulfil a challenge yet.

Sure, he’d heard plenty of stories about girls doing crazy things. His friend Mike claimed to have had a blowjob from a pair of twins last week. Then, his history professor had given her whole class buck naked, on the one day Jason had stayed home sick. The last straw was his nerdy roommate Mitch bragging about hooking up with an Asian girl he swore looked just like the lead from his favourite anime. 

All this made Jason even more determined to get some slut-box action, no matter what it took. That's when inspiration struck, he could sign up to the challenge himself. There was bound to be a way for a guy to get involved. Sure enough, there was nothing on the sign-up screen about the challenge only being for girls.

A few minutes later he was hitting send and sitting back in his chair. Smug in the certainty he'd soon be embarking on the sexual adventure of a lifetime.

The next morning that he received his reply.

NEIGHBOURHOOD COUGAR CHALLENGE.- You are Laura Daniels, recently divorced. Eager to prove you are still an attractive woman at 43. You have one hour to seduce a young buck and fill your pussy with his cum. If you win everything will be normal again. Lose and you will stay as you are.

Jason yelped as his phone shocked him. His whole body tingled and he watched in stunned disbelief as he transformed. His fingers grew long and delicate. His nails extending into well-manicured french tips. The changes spread up his arms. The muscles he'd been so proud of vanished leaving him feeling small and weak. Long blonde hair tumbled past his shoulder and a pair of large heavy tits sprouted on his chest. Even his clothing changed, a bra appearing to support his new breasts. His t-shirt turned into a halter top that left his shoulders and cleavage uncomfortably bare. He winced as his jeans pulled tight against his suddenly wider hips and swelling ass. For a long excruciating moment, shrinking boxers crushed his junk, turning into a sexy pink thong. The discomfort was mercifully brief. His cock and balls being sucked up into his body relieved the pressure. Grabbing his crotch he felt a vagina form in their place. 

Before he could react to his transformation it was done and he found himself occupying the body of an attractive woman in her early forties. 

“Holy Shit!” he cried grabbing at his new parts “I'm a fucking milf.”

As he groped his jugs he took in his surroundings. His cramped dorm room had vanished replaced by a clean spacious kitchen in a nice suburban house. 

He struggled to believe this was really happening but the way everything jiggled and swayed when he moved made it hard to deny. And if this was real then the rest of the message was probably true as well. If he ever wanted to piss standing up again he had under an hour to get a guy to cum inside him. His mind rebels at the idea, he was still a guy on the inside. Touching his curvaceous body might feel very nice but how could he even think of being with a dude? How would he even start?

A possible answer to that last question presented itself almost as soon as he had thought it. 

“All done Mrs D.” a young man about Jason’s real age peered around the corner. “I updated your anti-virus and cleared up some space on your hard drive it should run a lot faster now.”

As he spoke his face coloured and his eyes drifted to Jason’s chest. It’s only then that Jason realised that he was showing rather more cleavage than a woman should. It occurred to him that he should be embarrassed but he was not. In fact, he found the attention rather reassuring.

“This may not be my ideal body but it’s a damn sexy one.” he thought “and it looks like I’m not the only one who thinks so.”

“Ahem” the young man cleared his throat and made a desperate effort to maintain eye contact  “So, um yeah. That’s your laptop fixed and the WiFi connected and uh, you know I’m right next door if you need help with anything else. Not that you are helpless or anything, just, I know you are new to the neighbourhood and all that and I guess it must be tough moving to a new city and mom always says, God loves a good neighbour. So, yeah, welcome to the neighbourhood…”

Fiddling with his glasses the flustered young man trailed off caught between fleeing and wanting to stare at Jason’s body. His name was Alex and when his mother had insisted he help the new neighbour out he had expected the usual harried stressed-out soccer mom. The realisation that she was a stone cold milf had put him on the back foot to start with and now she appeared to be flirting with him!

“Oh my God” Jason thought “What a dork. I hope I’m never like that around a hot girl.” 

“I should give you something for your trouble…” he said out loud 

He made a show of bending over to retrieve a purse from the floor. He made sure to give his visitor a good long look at his big sexy ass.

He knew his pose was having the desired effect when he heard a strangled whimper from behind him. Peaking over his shoulder he saw his hapless victim struggling to cover up an impressive bulge in his jeans.

“Poor boy, he’ll do himself an injury if he’s not careful.” he thought a small thrill of wicked pleasure running through his body “Hehe, this is fun though…”

Pretending not to notice Alex’s distress he rifled through the purse. There were several letters in there from banks and lawyers, confirming bank details and payments to be made to Laura’s accounts. A notepad with passwords and numbers written in it. An assortment of high-end credit cards and a bundle of cash thick enough to make Jason’s eyes go wide. 

“Here you go sweetie,” he said peeling off a twenty and holding it out but when the younger man stepped forward to claim his reward he snatched to note back. “Unless… You’d rather I gave you a different kind of reward?”

His ploy left the two of them inches apart. Close enough that Jason could feel the heat of his body. Outwardly, he managed to maintain his composure but inside his chest, his heart was hammering.

“Oh god I’m actually doing this,” he thought “I’m seducing this poor sap, I’m going to let him fuck me and I don’t even know his name.”

The thought should have disgusted him but instead, he felt a heat kindling deep inside him.

“Mrs Daniels. I’m not sure…” Alex started to protest but Jason cut him off with a long deep kiss.
His nipples tightened and the fire in his belly became an inferno between his legs. It was strange to feel so aroused around another guy but Jason’s body didn't seem to care.

“Don’t pretend you don’t want this too,” Jason said coming up for air “I saw the way you were looking at me. You want me don’t you?”

Jason’s prey swallowed hard and nodded as Jason dragged his long nails over the taut fabric of his jeans, making the man’s cock pulse in response. 

Jason sank to his knees in front of Alex and freed his member taking a moment to admire it. He was no expert on the subject of other men’s cocks but this seemed like a pretty nice one to Jason. It felt thick and heavy in his hand, hard and smooth at the same time. Without pausing to second guess himself he wrapped his plump lips around it. It tasted of salt and the slickness of precum, so warm in his mouth. He wanted more, sucking it deeper until the head bumped against the back of his throat. He wondered if he should try and deep throat it. Could he manage that?  How would it feel to let this man fuck his face like a cheap slut? He moaned around  the cock at the thought 

“I’d make such a dirty oral slut but I need his cum in my cunt” he reminded himself

Satisfied that his boy toy was ready to do what he needed he broke off from the blow job and stood up. Keeping eye contact with Alex the whole time he stripped of jeans and panties and turned around. 

“Fuck me stud” he ordered bending over the kitchen counter “fill my dirty cunt.”

He shivered in anticipation as his buck took hold of his womanly hips and plunged into him. He moaned sounding like a porn star as his lover filled his needy pussy. It felt a little tight at first but the sensation of a thick cock stretching his new sex wide was so delicious he couldn't help pushing back onto it.

“Oh Mrs D” Alex gasped “you're so fucking hot. Your ass… your pussy… hunh!”
He began humping Jason hard enough to make his heavy tits bounce and swing underneath him. He went at it with more energy and enthusiasm than skill but Jason was still surprised by how much he was enjoying it. Alex's breathing came in ragged gasps and his thrust grew shallow and more frantic. 
He was getting close, Jason realised. Any second now he would lose his load and Jason's strange ordeal would be over. True, Jason wasn't anywhere close to cuming himself but that wasn't the point, right? 
No, he resolved, that wasn't enough. If he had to be this guy's cum bucket before he could go home he was going to make the most of it.

“Wait, wait,” he panted “Stop. I want to try something different”

Alex released his grip allowing him to ease himself off the man's cock. Once they were disentangled Jason guided them over to the sofa and told his partner to lay down. He then straddled Alex and began to slowly fuck the cock back into his cunt. 

“Mmm, much better.” he sighed reaching down to rub the tender nub of his clit  “Oh yeah Mama likes.”
He’d had never felt like this before. Never been so in control during sex or experienced anything so erotic. He felt so wanton, so desirable, so wild. Almost predatory as he focused on taking his pleasure from the younger man. 

Something was building inside, some force he didn't yet understand. It was like something was approaching, coming closer and closer. Almost there… 

Then it was crashing down on him. A wave of pure ecstasy that flooded his body beyond anything he'd ever imagined before.

“Oh god I'm coming!” he screamed his eyed rolling back in his head.

“Oh oh I'm close baby” Alex grunted, “I'm going to cum in your slutty cougar cunt.”

Still riding out the aftershocks of his orgasm a sudden mad impulse struck Jason. What if he didn’t go back? 

Laura’s life seems pretty great to him and his own life is average at best. No doubt there were a hundred excellent reasons why he should let Alex flood his pussy. He could forget about this escapade and go back to his life. But in the heat of the moment, all he could think about was how fantastic sex as a woman felt. In the throes of his climax, he didn’t care about anything except feeling that good again.

With an effort of will, he pulled himself off of his lover’s cock resolved not to let Alex finish inside him. Until he looked down at Alex and he looked so pathetic and frustrated Jason couldn’t bear to leave him hanging. Once again he took the man in his mouth relishing the taste of his own pussy on it. With a little more encouragement Alex finally had his reward. He groaned as thick ropes of cum pumped from his cock spilling from Jason’s mouth and coating his bare tits.

“Oh wow,” Jason sighed finally satisfied “We are doing that again sometime soon.”

“Yes ma’am” Alex grinned at the cum splattered woman “Whenever you want, just give me a call.”

The two of them got cleaned up and Alex went on his way with a dopey smile on his face. It wasn’t until Jason heard his phone beep that he even considered the consequences of his impulsive decision. His heart skipped a beat as he read the message from Slut-box challenge

You failed your challenge and so must remain as you are until you choose to play again. 

So that was it then. He was Laura Daniels now and Jason would live only in his memories. He was a little surprised to find he had no regrets. Being Laura felt right somehow, like an old coat fit exactly right. He thought about the loss of his youth and his manhood and they seemed like a small price to pay for what he had gained. New confidence filled him and if he ever did come to regret becoming Laura? 

Well, he was always up for a new challenge...