TheMarioGamer
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Last Chance
🕑 Added 2024-11-25 19:37:59 +0000 UTCHey there dudes and dudettes!
I am back again, with an upload that before was on DeviantArt before my account got deleted.
It is a caption trade with Li3L4, who wanted to see a guy getting his last chance.
I hope that you all enjoy this cap, and until next time stay happy and healthy!
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Gregory had everything a person could ask for, ranging from his handsome boyish looks to a massive mansion with a pool and enough money that he did not know what to spend it on.
At least he could enjoy all those things, as they actually belonged to his loving wife, Penelope, who owns the largest chain for female beauty products, offering everything the modern woman needs.
And while Gregory did enjoy the perks that came with being married there was one glaring downside – at least in his eyes – to this all, and that was his wife Penelope herself.
Because while Gregory just reached his late twenties, Penelope was already in her late forties, something that the not-so-happily married man quickly found to be a very big issue.
As they started dating he never held much affection, being more in love with her wealth than anything, though as the years came and went even those small levels of love went out the window.
With every graying hair on Penelope's head, with every wrinkle that appeared on her face, with every sag of her chest and every bump on her ass he grew more and more disgusted and distant.
Luckily for Gregory with his wife's money it was not hard for him to not only get a few young bunnies as housekeepers, but to also have them keep his bed warm while his wife was at work.
Unluckily for him this also came with some problems when said wife decided to once again get home early from the office, only to find her husband cheating on her once again.
"God dammit Gregory!" Penelope shouted, having just opened the door to her bedroom while wearing her lingerie, hoping to surprise her husband with an intimate afternoon.
But instead of getting frisky with him herself she yet again saw some young 20-year-old busty blonde bouncing on her husband's lap, only to jump off shrieking in surprise as the angry wife emerged.
"Oh, honey" she continued, sounding more tender as she looked at the frightened young blonde.
"There is nothing to be afraid of. You did not know, after all. Just... Just get your clothes."
The blonde girl in question looked relieved, quickly gathering her stuff and hurrying out the door.
Once she was gone though Penelope's fury returned tenfold, and as she glared down at her still naked husband said husband could only gulp in fear, fearing like the worst was about to come.
"This is the third fucking time, you cheating pig!" she started to scream in pure rage, yet she had to hold back sobs as tears started to form and roll down her eyes as she just stared at Gregory.
"D-Darling" the male in question stammered. "P-Please, you have to un-understand. This is not w-"
"Oh no mister! I heard that spiel already, and I am DONE understanding. Get out, immediately!"
Those words made a pit form in Gregory's stomach, not because of how broken his wife sounded, no, instead it was because he did not want to lose this life of luxury that he was living right now.
"H-Hey now" he continued to stammer. "L-Look, Pen, I am v-very sorry, and this won't happen ag-"
"You said this the last time already!" Penelope replied, openly crying right now. "And the time before! And I was foolish enough to believe you, but no more! We are DONE!"
"PLEASE HONEY!" Gregory tried one last time, hoping to convince his cash-cow to keep him.
"I swear this will never happen again!" he continued, even throwing himself down on his knees.
Penelope wanted to give a scathing remark to her cheating husband, though just before she was about to give him the biggest verbal lashing in his life she got a devious idea for the cheating pig.
"Well, alright" she icily said, making Gregory look up in surprise, not thinking it would be that easy.
"I will give you one last chance. But you have to make it up to me and prove your loyalty, alright?!"
"O-of course honey, everything for you!" he happily replied, inwardly cheering at his success.
"Now come to bed, then I can start to show you how much I want to make it up to you!"
"No thanks" Penelope just coldly said. "I don't want to be anywhere near that bed right now, not after all you have done in it. I will happily take the couch" she finished before going away.
The next day Gergory was eagerly preparing his wife's return, having bought some nice bouquets with her credit card and ordering some nice food, hellbent on pleasing her enough to be able to stay.
However when Penelope returned from the office carrying a big burly bag she barely glanced at the food, and instead of being happy about the flowers she took them and threw them in the trash.
"Come" she just ordered, going up the stairs to their bedroom, and Gregory simply followed, not knowing what was going on but also not wanting to make her any more upset than she already was.
"So you think some food and cheap flowers will make it up to me?" she roughly asked with a scoff while shaking her head before emptying the bag on the bed, showing all kinds of feminine products.
"Oh no, that won't be enough this time. I want you to feel as humiliated as I felt yesterday!" she said in slight anger, before throwing a shaver and cream at Gregory. "Now shower and shave!"
The cheating husband, not pleased about the turn of events but also unable to do anything about it, just did as he was told, and a few minutes later returned, now hairless from neck to feet.
"Good!" Penelope said with a smile that looked wrong on her as she inspected Gregory's work.
"And now for the fun part!" she continued, and before her husband could do anything she grabbed massive breast- and hipforms and slathered them with glue before attaching them to his chest and ass.
And before he could recover Penelope continued her work by grabbing his willy before also covering it in glue and pulling it in between his legs, safely tucking it away so nobody would see it.
"You like them busty, right? So I think it deserving if you end up just like them!" she teased, her voice dripping with restrained anger as she went back to the pile and retrieved a corset.
"N-Now hold on a min-" Gregory started to say, but just as he did Penelope wrapped the corset around his stomach and put her knee in his back before pulling as much as possible.
The corset went tight, making the soon-to-be feminized guy groan and huff as he was robbed of air, and once his wife was done and tied the strings he was left with a nice hourglass figure.
"If only you could see yourself" Penelope said while Gregory struggled to catch a breath, the corset forcing him to take small huffs. "You would surely screw a girl that has a figure like you have now."
The guy in question, unable to reply, just tried to gale, not amused with the joke, but unluckily for him Penelope was far from done, so once again he was put through the wringer of feminization.
The process continued with Penelope grabbing a black shiny latex catsuit and pulling it up Gregory's enhanced body, struggling to close the zipper in the front thanks to his massive chest.
So she just left it open, keeping a nice amount of cleavage for the world to see, before she moved on to make Gregory's face look just as slutty as the rest of his body did right now.
She started by covering him in layers of foundation before gluing on some fake lashes and adding some black eyeliner alongside some mascara to give his eyes a sultry and inviting look.
Next Penelope grabbed some tweezers, and not so kindly began to pluck his eyebrows, pulling as slowly as possible with each hair, until he was left with thin feminine arches and aching skin.
Afterwards she moved on to the lips, for which she grabbed a needle and began to inject them with some filler, making them puff out immediately before covering them in a soft pink lipstick.
Lastly she grabbed a bleach blonde wig that she glued on top of Gregory's head before finishing the transformation with some 5-inch black boots and a broad belt that she wrapped around his waist.
"Hmmm, looks like that the corset is not tight enough" Penelope mused, looking on in disappointment as she could not get the belt to its tightest setting, leaving 2 holes left to fill.
The comment made Gregory sweat, his insides already protesting their current confinement. "But it would be too much work to undress you and redo it now" she continued, making Greg sigh in relief.
"Gweat, so we awe done, wight? I feew totawwy humiwiated, tho..." Greg started to say, wincing at the lisp of his lips, but Penelope just sent him a glare that immediately made him shut up.
"No, we are not done, not by a long shot! So here is what is going to happen. I am going to eat out, ALONE, while you stay here" she began, grabbing herself some formal clothes to change into.
"Meanwhile YOU, Gabrielle, will stay here. I hired some new housekeepers so you can show me how loyal you are and how much you want to make it up to me. So don't mess up your last chance!"
With that Penelope left the house, leaving Gregory alone, anxiously waiting for the new bunnies to arrive, already feeling humiliated at the thought of young sexy woman seeing him like this.
But to his shock and horror a few minutes later he found out the new housekeepers were not sexy woman, but strapping you bucks, each over 6 feet tall with muscles that could replace steel cables.
Greg, knowing what surely is expected of him to prove his loyalty to Penelope with his new tits, thick lips and catsuit that had a zipper at his ass, just gulped, thinking about the money as he made his way to greet the new housekeepers and to "thank" them for their hard work.
A few hours later Penelope returned to her home in happier spirits than before, having enjoyed her time out with her friends, and once she was through the front door she immediately went upstairs.
When she opened the bedroom door Gregory greeted her, his hair disheveled, lipstick smudged and the once shiny black latex now matted and partly white, with his cleavage forming a big white pool.
"H-Hey Penelope"
Gregory weakly let out as his wife just watched him with a face like stone.
"I-I did it. You can't be angwy at me anymowe" he rasped out, his throat burning as much as his ass at the moment. "Th-this has to make it all up to you, wight? So we can go back to nomaw agwain?"
For a few moments nothing was said, but then Penelope started to smile, making Gregory brighten up a bit as he thought he was finally done, but then his wife started talking, and he went slackjawed.
"What are you talking about?" she started, her smile turning to a devious smirk. "I mean I just told you to prove your loyalty, and what do you do when I tell you that? Cheat while I am away. Again!"
Penelope wished she had a camera, because the look on her soon-to-be ex-husband was priceless.
"There is no going back to normal. You fucked it up. I gave you one chance, one LAST chance to prove your loyalty to me, and you screwed it up. You really blew it" she continued, eyeing Gregory.
"Though that doesn't seem to be the only thing you blew and screwed by the looks of it. That has to be what? 30 times cheating? 40 times? I can hardly count all those times, only that it is a lot!"
With that said she grabbed Gregory by the shoulders, making sure to grab one of the few clean spots, before she pushed the still shellshocked guy towards the front door and out said door.
Once he was outside the door closed behind him, and even through the haze he could hear it being locked from the inside, and he was still unmoving until he heard a shout from the window above.
"Hey, Gabrielle!" Penelope shouted, disappearing from the window shortly before the soiled mattress was thrown out of it. "You can keep it! I don't want it anyway after all the things you did on it!"
With that the window closed, and the cheating Gregory was left with only the mattress and the clothes on his body.
