themariogamer

No Second Chance

Published: September 2nd 2024, 8:30:13 pm

Hey there dudes and dudettes!   

As promised the new caption with a bit of delay.
This time around it is a caption trade with Ugu-Deviant-2, who wanted a sequel to my "Last Chance" caption!  

I hope that you all enjoy this cap, and until next time stay happy and healthy!

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A week had passed since Gregory was thrown out of the house by Penelope, though if one would ask Gregory himself it felt more like a month, each minute filled with more humiliation.

Since he had no money or ID on him he was forced to sleep out on the street, reluctantly using the smelly and soiled mattress Penelope "gifted" him so he at least didn't sleep on the ground.

Sadly this was the only slight positive as Gregory had to deal with his slutty attire attracting all kinds of unwanted attention with guys always making advances on him that he luckily managed to evade.

Though while horny males wanted to be close to him many females and families just sneered at him in disgust, thinking he was a "woman of the night", and in turn avoided him at all costs.

So nobody was willing to help him out, and the males willing to help him out wanted something in return, forcing Gregory to fend for himself, making him go so far that he rummaged for food in the trash to at least have a tiny sliver of his dignity left in the end.

But after a week of this horrid experience, the feminized male was just not able to take it anymore, and so he found himself back at Penelope's house, knocking on the door in desperation.

After minutes, just as he was about to give up, the door opened and his former wife stood inside the frame, looking at his disheveled state in disdain as she wrinkled her nose.

"I am sorry, I think you have the wrong door" she said with a cold expression on her face, acting as if she didn't know who was in front of her. "The brothel is quite a few blocks away, you know?"

"Pleathe forgive me, Penelothy" Gregory begged, actually falling down on his knees. "Pleathe, I learned my lethson! I will never cheat on you again, alwight? Jutht pleathe take me back! "

The female in question just kept her impassive stare, looking down on her former husband, now nothing than a quivering and disheveled mess, and her heart was not moved at all by his words.

"I know you won't ever cheat on me again, Gregory" she said, and hope welled up inside the male. "Because I will never be with you again. I trusted you, and you betrayed me after all!" Penelope continued, her voice not betraying any emotions, making Gregory hang his head in despair.

"Though I am not totally heartless. Since I was forced to fire all the employees for sleeping with my husband I am out of a maid. So if you will become my maid I will at least let you sleep and eat here" Penelope offered with a small smirk as she looked down on the still kneeling Gregory.

The male in question meanwhile was still as a statue, not speaking a word as the shock of his ex-wife's words that shattered the last bits of hope he had to get back his masculinity ran rampant.

But when realized that she offered him a deal he reluctantly looked up, after all being a maid was better than sleeping on the streets. "A-Awight... I will be youw maid" he whispered, making Penelope's smirk widen, knowing just how much fun she was going to have with this.

"Excellent! Then come along, Gabrielle, I need to get you ready for your new job" she said with a small laugh before taking her feminized ex-husband's hand and dragging him to the bathroom.

Once inside she made him undress before ushering him the shower, and Gregory let out a sigh of contentment as he was able to wash away the filth of the last few days, staying for nearly an hour.

Once he felt sufficiently clean he stepped outside where Penelope was already waiting for him, and Gregory's eyes widened and his mouth hung open as he looked at the latex getup she carried.

"W-whaw is THWAT?" he nearly gasped out, seeing the shiny fabric, or more accurately the lack thereof. "Your uniform of course. Maids should be enticing after all, at least according to my ex-husband. But enough about him, this is all about you and your new job, Gabrielle, so come here!"

And before Gregory could protest Penelope was upon him, using the myriad of items she brought with her to once again transform him into a true beauty.

With his willy still tucked and the breastforms still glued on she began by taking what looked like a big syringe before plunging it into his chest, making the already large mounds grow even more. Next she grabbed a black lace corset, and remembering the last time Gregory could only whimper as she put it around his stomach and started pulling on it as hard as her body allowed.

"Last time we didn't tighten it enough" she grunted out as she continued to pull, making Gregory wheeze, before she put her foot into his back for more leverage. "We won't make that mistake again!". Gregory could say nothing, his breath growing more and more labored as the corset got tighter and tighter until Penelope was satisfied, leaving his chest and ass jutting out compared to his tiny waist.

"It took a bit of work" she said, a pleased smile on her face as Gregory tried to catch his breath. "But I think we can finally get you into that uniform of yours!" she continued, grabbing the get-up.

She then pulled some black lace panties up his legs until they nicely settled, followed by the dress being pulled over his head, the fabric barely reaching over his ass and leaving a lot of cleavage exposed as there was no bra and the dress was shoulderless.

Next came a pair of white fishnet stockings that Penelope rolled up his legs, followed by a pair of towering black plateau heels that Gregory found easy to walk in after his week of hell.

"Now you nearly make a presentable maid, just a few more adjustments" Penelope teased, and even though Gregory finally found his breath he had no strength to protest any of her words.

She then re-did his make-up, starting by covering his face in layers of foundation before adding some eyeliner alongside some mascara to his fake lashes, giving off a sultry and inviting look.

Next Penelope grabbed some tweezers, and once again started to pluck his eyebrows, thinning them out even more until they were the picture-perfect image of femininity.

Afterward she did his lips, injecting some more filler before painting them slightly red, after which she removed his previous wig, only to replace it with a mop of luscious dark golden locks.

Penelope then finished up the outfit by placing some black ribbons with frilly white edges on his wrists and around his neck before putting the usual white headpiece onto his new golden locks.

"And done! Now this is what I call a perfect maid. I bet my ex-husband would have LOVED you, don't you agree, Gabrielle?" Penelope sneered while she was holding out a mirror to Gregory.

The feminized male meanwhile could only stare in shock, not believing that he looked even sluttier than before, his chest and ass nearly on display with the tight and revealing set of clothes.

"But that is enough talking, you have a job to do after all. Now I want you to clean the bathroom, after which you can clean and wax the stairs. And then you can start with dinner, I expect it ready at 6pm."

"W-what? Now wait a miwute, twatt if too m-" Gregory started to say before a painful stinging sensation silenced him, and in shock he looked at the outstretched hand of his ex-wife.

"Silence! You don't get to talk unless you are ordered to do so! And if you address me I expect you to address me as mistress! Do you understand that, maid?" Penelope angrily said, making Gregory tear up."Y-yes..." he stammered before being silenced again. "Yes WHAT?!" "Y-Yes, miwwthewf".

"Good. Now as I said I expect you to clean the house top to bottom every day. You will also provide breakfast, lunch and dinner alongside snacks during the day. I expect you up at 4am, and you are free to do as you please after 8pm. Then you can make yourself at home inside the broom closet. And now shoo, you still have much work to do!"

And so Gregory's life as his ex-wife's maid began, where he was forced to pretty much take care of everything, from groceries to cooking, to cleaning, his only break being between 8pm and 4am.

At first he held out hope that this would just be temporary and that Penelope would forgive him and take him back still, but soon days turned into weeks, and weeks turned into months.

After nearly half a year Penelope one day came back with another guy that she introduced as Hans, her new boyfriend, and now Gregory had two people to care for as she refused to hire more maids.

At that point Gregory lost all hope that things would go back to normal, but with no other choice he continued being a maid, just this time under the lustful gaze of Hans and his grabby hands.

And as he thought things could not get any worse one day, when Penelope was out of the house on a business trip and he himself was cleaning the kitchen he felt Hans approach from behind.

Before he could ask him what he wanted Gregory was bent over, face pressed against the counter and his panties slid down. "Oh, you always teased me with that set-up, you little minx. Don't deny it, I know you want it!. And don't worry, Penelope is gone for a week, so we can have fun."

And as Gregory felt Hans hilt himself inside him before he started to hump away he could only hope that Penelope would return early, as maybe catching Hans cheating would give him a brake.