A Christmas Revenge (Christmas Eve)

Hey there dudes and dudettes!

I wish you all a very X-mas, and hope you have a great time by yourself or with family!

And as promised here is the first part of a three-part series!
The series is about a brother doing his sister wrong, and paying the ultimate price for it on Christmas.

I hope you all enjoy it still, and until next time stay happy and healthy!

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„Come on sis, can't you give me something a bit more... covering?“ Jack timidly asked as he teetered in his heels, trying his best to not fall with the unfamiliar footwear. „Hey, no getting cold feet now, Jaqueline“ Penelope said, using a feminine name for her brother, much to his chagrin. „I am paying you good money to be my friend's replacement!“

„I know, and I am not getting cold feet!“ Jack snarked back. „I just didn't think it would be something that revealing...“ he admitted, pointing at the leotard that left nothing to the imagination. „Well, it is not my fault that you never asked what you would have to wear for the photoshoot. And now stop complaining and get down to the living room for the pictures!“

And just as his sister pointed Jack could blame no one but himself for his current situation and getup as it simply was his greed that led him down this road of feminine clothes. It all started when his sister came running to his room on Christmas. She looked rather disheveled as she barged in without knocking, making Jack frown at her as he looked up from his phone. „Can you at least kn-“ he started to admonish her, but was quickly interrupted by his sister who looked like she was in a hurry „Jack, I really need your help! Right about now!“ she shouted.

This made Jake frown even further, not thinking that his sister would ever ask, let alone beg, him for anything ever since the falling out they had a few months ago, souring their relationship. „W-What do you need, Pen?“ he asked, a bit unsure what his sister could need that she even went to him for it. „I need you to model for one of my photoshoots!“ Penelope answered immediately.

„Ehhh... Come again?“ was the only thing that he could say in return, thinking he had misheard as his photographer sister never did a shoot with him, let alone male models at all, only doing females. „I need you to be my model“ Penelope slowly repeated, looking her brother directly in the eye. „You see, Jenny bailed on me last minute as she had a family emergency, so I called the others, but no one has time on Christmas“ she began to explain her dire situation to Jack.

„But I really need that shot done today, and since our family is out at the market right now I can only ask you to be my replacement model. There is no one else after all!“ she continued. „W-Well, I am not sure what to say exactly, but yeah, I can be your model if you need it“ Jack said with a smile, thinking this was a way to rekindle their relationship, but Penelope now looked away.

„T-That is great, really. But you should know that you would need....“ Penelope started to say before going to incoherent mumbling towards the end. „I would need to... what?“  „I... I would need to dress you up like a girl“ Jack's sister finally said, and suddenly it clicked inside Jack's head.

Her timid demeanor, her going to him, Jenny not being available all came together. „Absolutely not“ he immediately said, crossing his arms while shaking his head. „I am sorry sis, but there is no way I am gonna let you dress me up for your little photoshoot.“ „PLEASE JACK!“ Penelope pleaded, sounding desperate.

„I really need to do the photoshoot today, the client counts on it!“ „Sorry sis, but I am NOT doing this, not even for you!“

„Come one! Just... Just count it as your Christmas gift for me! You would want to gift your sister something after all, right?“ „Sorry, but I already have a gift for you, Penelope.“

„Probably just some cheap make-up like the last years, right?“ she said with a deadpan stare, and Jack had the decency to blush at being called out like that as his sister hit the nail on the head. „Okay, then... Then I am gonna pay you! Does that sound better? This is a good-paying gig, so how does 400$ sound? Or would you rather have more? How about 600$?“

This made Jack's eyes widen, after all he could always use the money, and getting offered 600 bucks for a little bit of dress-up seemed like quite a nice deal in his ears. „I... Okay. 600 bucks, and I am going to be your model. Deal?“ „Are you sure about it? There is no going back after this“ Penelope asked, wanting to make sure as she gave him a serious look.

„Yeah, I am sure about it. Can't pass up 600$“ Jake said with a shrug. „Then we have a deal!“ Penelope shouted eagerly before she grabbed Jack and dragged him to the bathroom. Inside she handed him a razor and shaving cream before pointing at the shower.

„We have no time to lose, so you shave yourself from neck to toe while I get everything prepared, ok?“ Once he emerged from the shower and dried Penelope returned with a big heavy-looking box, and when she saw her brother she looked him up and down before frowning.

„I am sorry Jack, but the eyebrows have to go" she said, making Jack's eyes go wide once again. "But don't worry, eyebrows regrow very quickly" she continued before he could object, and with a heavy heart he also shaved off his eyebrows.

"Good, now we can move on to your body!" Penelope happily exclaimed before taking some heavy-looking breast- and hipforms from the box and showing them to her brother. „W-What are those for?!“ he exclaimed in shock, making his sister roll her eyes. „To make you look female of course. Or did you think we can just pull you off as a female looking like this?“ Begrudgingly Jack had to admit the point, and so he soon found the forms glued to his body, giving him curves that no male should have, though his sister was far from done.

„Looking good, Jaqeuline“ she teased, making Jack glare at her. „Though there is still one thing out of place“ she continued, and before Jack knew it she glued his manhood between his legs. „Now you really look like a female model“ Penelope continued to tease, and Jack blushed brightly at the comment. „J-Just get this over with, alright?“

His sister was happy to oblige, and so she continued the transformation by grabbing a tight Santa-themed leotard that was a bright red with some white fur-trimmings and pulled it onto his body. It was a tight fit, especially around the crotch and chest are, and it left most of Jack's new boobs on display with its large cleavage, but after some pulling Penelope managed to get it all in place.

Next came a pair of white knee-high 6-inch heeled boots that she forced onto his feet, struggling as they were 2 sizes too small, before she placed a blonde wig on his head. „Now we are only missing the make-up, Jaqueline, and then you are ready for the camera!“ Penelope exclaimed, and before Jack could say anything his was was assaulted by brushes.

She started to apply multiple layers of waterproof foundation to his face, giving him a shiny and smooth complexion, before she added some blush and moved on to his eyes. For those Penelope glued on some fake lashes and covered them in black mascara before adding pink eyeshadow and black eyeliner before finishing by drawing on some fake eyebrows. Afterward she did his lips, adding multiple layers of lip-plumper before coloring them nude, after which she finished the transformation by adding a Santa hat, a necklace and some bracelets.

„And we are done, Jaqueline!“ Penelope said, handing Jack a mirror so he could see the results, and what he saw made his eyes go wide. „I- What? Is that- How- Is that really me...“ he mumbled.

„Yes, this is you. But don't worry, this can easily be reversed. But now we gotta hurry, don't have much time before the deadline“ Penelope assured before grabbing Jack and pulling him downstairs. „Yeah, let's better hurry, Mom and Dad should be back soon, and I don't want to explain this.“ he said, being seen all dolled up by his parents and extended family was the last thing he wanted.

„Oh, no worries. Mom and Dad wrote me that they would be back in an hour or so“ Penelope just said with a shrug as they arrived to stand before the living room where she suddenly stopped. „Shit. I forgot my camera upstairs! Just go ahead, Jaqueline, I will be with you shortly!“ Penelope said before hurrying back upstairs, and Jack, just shrugging to himself, went into the living room.

What he did not expect when he entered was for his parents, his uncles, aunts and cousins to all be present, staring at him with wide eyes as he entered, and all he could do was freeze up in shock. „Jack? Jack, is that really you?“ his mother asked, looking at him with wide eyes, and Jack could only nod dumbly as a reflex, his throat still refusing to make any sounds. „Oh my...“ she said before his father continued „So Penelope was right“ his father said, though he looked far from angry or disappointed. „And we did not believe her. God, we really did not believe.“

Confusion was now added to the shock Jack felt, and it only got worse when suddenly his parents came over to him, pulling him into a deep hug, tears in their eyes.

„Oh my god, we are so sorry“ his mother said. „We really did not believe Penelope that you want to dress like a woman so badly! God, we really are some rotten parents, aren't we?“ „But don't worry, we will make sure to make it up to you, we promise!“ his father continued for his mother, sharing tears with her. „Wha- But- I- No, I don't- Penelope paid me to dress up-“ Jack began to say, finding his voice as he wanted to put things straight, but suddenly another pair of arms joined the hug.

„Oh Jaqueline, don't be like that!“ he heard his sister say as she hugged him too. „There is no need to hide and no need for excuses! We are all on your side, alright?“ „YEAH!“ „Of course!“ His whole family chimed in in support, making Jack want to dispute the claims more, when he suddenly heard his sister whisper into his ear.

„I have the whole dress-up part on camera. You look all willing and not putting up a fight. So you better play along if you don't want the video making its way around the internet, alright?“ she threatened, making Jack gulp.

„Oh, Jaqueline“ his mother said, breaking the hug with a big smile. „I hope you can forgive us. We really did not believe your sister when she told us you would want dresses and make-up for Christmas. Instead we got you all those games and consoles you surely don't want. But no worries, we will go to the mall tomorrow, return everything and then we can go on a nice shopping trip!“