TheMarioGamer
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A Christmas Revenge (New Year's Eve)
🕑 Added 2025-01-01 00:51:44 +0000 UTCHey there dudes and dudettes!
I wish you all a happy new year! I hope this year will be better than the last one, and I hope to be more active now that my studies are over.
And as promised, here is the third and last part of my little "Christmas Revenge" tale. I hope you like it!
I wish you a happy celebration, and until next time, stay happy and healthy!
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"Please explain why I am doing this again, Penelope?" Jack whined from his position on the floor while trying his best to look seductive, just like his sister wanted him to look. "Because I want you to," she replied, not wanting to give any explanation as she just kept shooting pictures with her phone. "And now push your chest out more, Jaqueline!" "But I don't want to!" Jack nearly shouted, getting up from the floor and stomping over to his sister, or at least he tried, as the 7-inch heels forced him to mince over to her.
"I am sick and tired of this! Because of you, I now have a whole female wardrobe, this ridiculous chest, and everyone in the family thinks I want this. And now you want those pics for what?!" "Because I can!" Penelope just barked back. "And now you better get on the floor again and look like a wet dream, or else the whole world will know about you. Or do you believe anyone will think I am forcing you to do this at this point?" she continued, and reluctantly, Jack did as he was told.
After all, he knew that his sister was right. If she released the videos she had of him dressing up on the internet now, nobody would believe that he was far from a willing participant. Since the fateful day on Christmas, Jack was forced to spend every waking minute in tight dresses or skirts and tank tops while walking around in towering high heels, all approved by his sister.
To make matters worse, his parents, who forbade his sister from showing so much skin years before when she grew up, had no problem with Jack wearing them and showing off. Now, a week later, it was New Year's Eve, and Jack planned to come clean to his parents after midnight, thinking he could claim that this experience was not the right thing for him.
However, before that, Jack got one more surprise: a bit after lunch, his sister barged into his room, making him jump up from his bed, where he was wearing one of his sister's comfy hoodies.
"Well, well, well, what do we have here?" Penelope said with a smirk as she watched her brother. "Care to explain why you have my hoodie when you have a perfect wardrobe, sis?". Jack just grumbled as he refused to look at his sister, but inwardly, he was panicking. After all, his sister had made it clear after their little shopping trip that she wanted him to wear what they bought at all times.
"W-Why are you here?" he responded instead, trying to avoid the topic, making his sister smile widely. "Nothing much, I just came by to get you ready for the party later on." "Party? What party?" Jack asked in confusion, not knowing what his sister was talking about. "The New Year's Eve party? The one that is every year?" Penelope explained, raising an eyebrow.
"Oh yeah, our family get-together," Jack said, finally realizing what his sister meant. "I would not really call it a party, but whatever. Though I can get ready for it myself, you know?"
"Well, by the looks of it, you can't," Penelope said while looking straight at Jack's hoodie. This made the boy once again fill with dread, as he apparently was not able to avoid punishment. "I mean, a girl like yourself surely wants to look her slutty best and not walk around in this glorified potato sack, right?" she continued with a smirk, making Jack gulp as his sister got closer.
"And so, since you seem to have trouble making yourself presentable, it is my sisterly duty to help you get ready and make sure you look the best you can. Don't you think so, too?" "Y-Yeah," Jack just asked, pale as a ghost, as he looked at his sister's evil smirk. "I sure could use some help to make me look my best," he continued to stammer.
"Perfect! Good that we can agree on this!" was the only reply he got before Penelope grabbed him by the arm and hoisted him up, dragging him to the bathroom.
"Now, would you kindly give me back my hoodie?" she asked once they were inside the bath, holding out her hand expectingly. "I think it is time we get you into something much better!" With no other option, Jack did as he was told, and when he was done, Penelope could see he was not wearing anything underneath, making her frown deepen while Jack got nervous.
"Go get a shower, sis. I will get you something nice to wear, don't worry," Penelope said before leaving the room, hoodie in hand, leaving Jack to do as he was ordered. Shortly after he had toweled himself off, his sister returned, holding some clothes in her hand as she approached Jack, who could only hope she had nothing too extreme in mind. This hope was quickly dashed as she presented him with a corset, making Jack pale. "The dress I have picked is a bit on the tighter side, sis, so we gotta get you slimmed down a bit," Penelope said with a smirk as she got closer while Jack tried to back off but quickly hit a wall.
"N-now, wait a minute, I have never worn a corset before!" he pleaded with his sister, but she was unyielding. "Well, then, this is your first! And now bend over so I can get to work on you!"
And with that, Jack soon found himself bending over as Penelope wrapped the corset around his torso before pulling it as tight as possible, going so far as to put her knee on his back to make his waist as small as possible, robbing him of his breath in the process. "T-Too... ti.. ght..." Jack rasped out, but his sister just ignored his pleas. "Nonsense! We can still get an inch or two from your waist, so we are not nearly straight enough!" she just responded in glee.
In the end, Jack now had an hourglass figure, his now tiny waist putting his ass on display. At the same time, the cups of the corset made sure to push his chest up, making them appear much more prominent and perkier. With that done, Penelope grabbed a red silk thong she put onto Jack, making sure to pull the fabric as far up as possible to make it dig into his ass and give him a wedgie before continuing.
For the next step, Jack's sister grabbed a red latex dress that she pulled over his ass, the fabric clinging tightly onto his body even with the corset, showing off every single curve he had, the tiny dress just barely reaching over his cheeks while leaving most of his cleavage on display.
"Wow, you look so gorgeous in this dress, Jaqueline!" Penelope praised, making Jakc blush. "Now we just need to do your make-up, and you are ready for the party of your life!" she continued. With that, she caked her brother's face in foundation, making the skin appear smooth and shiny before adding a bit of blush, after which she moved on to her brother's eyes.
For those, she added a bit of mascara to the lashes and added some eyeliner, giving Jack the best smoky bedroom eyes she could before retracing his new tattooed eyebrows. Next, Penelope paid attention to his lips by using multiple layers of lip plumper, making them appear big and puffy, before painting them with some light red lipstick. Lastly, she grabbed an iron and straightened Jack's long blonde hair, sweeping it mostly to one side while making the ends curl slightly before forcing her feet into 7-inch silver platform heels.
"And done! So tell me, sis, do you like the look?" Penelope asked with a smirk as she presented Jack with a mirror, and the feminized guy could only look gobsmacked at the beauty staring back. "Well, I take that silence for a yes," Penelope said with a giggle as Jack stared at the mirror, still in disbelief despite his experience. "How about we take some nice pictures for the album?"
So Jack was forced to do a photoshoot with his sister, who made him pose in increasingly sexy and seductive poses. All the while, Jack could not figure out why she wanted all those pictures. "Wow, these are looking great!" Penelope exclaimed after the photo shoot, gleefully looking at the pictures on her phone. "I just hope your date likes them just as much as I do!"
"Yeah, yeah, I hope so t—Wait, date?!" Jack started to say absentmindedly before the reality of his sister's words hit him. "What date?! We are just having our family get-together!" "That is what YOU said, dear sis. I meant the local NYE-Party," his sister explained. "Because after seeing how good you look, Mom and Grandma thought it would be a good idea to set you up with a date, and I convinced them that you would love to, but only if you could go to this party, so..."
"Oh, HELL NO!" Jack screamed at his sister. "There is no way in HELL that I will go on some date with some random guy that I don't even know, especially not looking like this!" "But you look great! And besides, you know the guy. After all, you broke us up," Penelope said with a glare, making Jack's eyes bulge out of his head as he realized she was talking about her ex, Tom.
Before Jack could retort, he could hear the doorbell ring, making his sister smile. "Oh, that must be him! It's right on time, too—perfect!" she continued as she pushed Jack out of the bedroom. "Now remember, Jacqueline. I want you to be the perfect date for Tom. And if you decide to weasel your way out of this, remember all the videos and pictures I have of you. And what would Tom do if he found out he was stood up by some guy dressing as a girl?" Penelope threatened.
There was nothing Jack could do as he was led to the front door, and when he opened it, he was face to face with Tom, the former quarterback, who was two heads taller and thrice as broad. "Yo, you Jaqueline?" he asked in a deep voice, and Jack could only nod timidly. "Great, then let's go," he continued, wrapping one of his muscular arms around Jacks's waist, his big hand on his ass.
"I got your pics, and I have to say you look even sexier in person," Tom said as he led Jack to his car. "And about the messages... Don't worry; I will make you see nice fireworks! As Jack was led away, Penelope waved at the departing duo. "I just hope you used the toys I bought for you, Jaqueline; otherwise, your night will be a real stretch!" she thought as she closed the door.
