Christmas Wishes

Christmas Wishes

by sammig82

Dressed in a long-sleeved knitted top and navy blue jeans, Ryan Hobart sat next to his crush and best friend, Blair Waldorf who looked her usual radiant self in a brown drop-shoulder-turtleneck-dress and a pair of fashionable above-knee high-heeled boots. He could see her breath from her luscious lips amid the cold even as they were an arm's reach from the heat of the fireplace.

Her parents were away on a crucial inheritance matter. Hence, the two college sophomores would be having the fancy Waldorf penthouse to themselves for the rest of the evening. Overlooking the East River, Blair’s family was affluent enough to afford the property in an Upper East Side neighborhood of Manhattan. Words were going around that they were about to become even more financially astute with the passing of her grandfather who owned more than half of the buildings in the city.

Ryan’s family was no slouch either. But the fortunes of the Waldorf Dynasty were unmatched. Blair could not care less about any of that when she had become friends with Ryan. The boy from Brooklyn had grown into a handsome man, but that still did him no favor when it came to turning their friendship into something more. Since she had rejected his approaches on multiple occasions, it came as a surprise when she had invited him to her place without any of the usual members of their Upper East Side Society in tow.

“So what gives?“ Ryan sitting like a Hugo Boss model, holding a knee to his chest as he stared at the flickering fire. The warmth it provided felt soothing against his golden skin.

“What do you mean?” Blair returned his question with another one.

“You and me. Alone. With your folks away,” Ryan said, still looking at the fireplace.

“Nathan was forced to attend some fundraiser organized by his parents. Serena had another family emergency with her brother. Jenny’s having a modeling gig at the NYFW,” Blair responded. She too was staring at the dancing flame. It was especially fascinating in the winter.

“Well, that’s disappointing,” the hunk said.

Blair had to turn and look at him before saying, “…that this wasn’t a date? Can’t say that I’m not flattered, Ryan.”

There was a momentary silence as Blair studied her best friend’s handsome features before finally asking, “Tell me Ryan… about your Christmas wish.”

“Haha… Playing Santa, are we?” Ryan chuckled as he shifted his gaze away from the warmth towards Blair before contemplating, “Hmm, let’s see. Other than having you to start taking ‘us’ seriously?”

“I know you, Ryan. Deep down, you’ve always wanted something… Something much more than Blair Waldorf,” the part-time socialite said while looking into his deep blue eyes.

It was not often to see the usually confident man looking away in embarrassment. Somehow, he felt compelled to spill his deepest and darkest secrets to whom he had always desired to be his soulmate.

“You know… I… I’ve always wanted to know what it’s like?” Ryan stammered a little.

“What do you mean, Ryan?” Blair inquired. There were some hints in her voice that she already had a pretty good idea.

“You know what I wanted, Blair,” the handsome young man said while avoiding her eyes.

That was when Blair started touching him. Her hand landed on his crotch as she leaned in to kiss him passionately. Instead of reciprocating, Ryan pushed her away.

“What’s wrong? I thought you wanted… this,” Blair said while confidently pointing at her own body.

“No, Blair. Not like this. Have you been drinking?” Ryan asked, but there were no signs or scent of her being intoxicated when he arrived. “Because you’re not acting like yourself right now,” he added before turning away and leaving.

“WAIT! Don’t go, Ryan!” Blair stood up with her arms crossed underneath her pert bosoms. “I know exactly what you’ve desired. I’ve always been able to tell, Ryan Hobart.”

The 21-year-old turned around to find a naughty grin on Blair’s pretty face. GOD, she’s so hot, he thought.

“You wanted to know what it’s like to be ME?” Blair said, once again giving the impression as if she had been drinking.

“What?” was all Ryan could come up with.

“To be more precise, you wanted to know what it’s like to be a WOMAN like me,” Blair said, the edge of her lips curving almost to her ears.

Ryan did not respond. He did not turn to leave. In fact, the good-looking chap did not even move a muscle. There were only two possible explanations: either Blair was hitting too close to home, or he was just speechless at how crazy she had sounded.

“As the saying goes, it takes one to know one. I know exactly the feeling Ryan,” Blair said, sitting back down in front of the fireplace before crossing her white-pantyhose-encased legs.

“You’re not making any sense, Blair. How could you possibly know what it’s like? You’re already YOU, Blair. Privileged and beautiful. A lot of men would do anything to be with you,” Ryan finally said what’s been cooped up all this while.

“You’re not too bad yourself, Ryan. A long line of girls would be dying to go out with you as well. But, that just doesn’t cut it for you,” Blair said, staring at the fire.

She was right. It felt as if his best friend was peering into his soul. Still, there were things that even the best of friends should not have known. Something deep… and dark.

“You’re not Blair. Who are you?” Ryan had asked that question before as a joke, plenty of times, whenever Blair was being kind and thoughtful because that was never her character. This time though, he felt as if he was asking it for real.

“Finally. You’re asking the right question,” Blair uncrossed her legs and stood in front of him once more.

Her deep blue eyes did not stray away from his as she began to undress. The warmth from the fire was comforting enough for her to strip down to her lingerie and white pantyhose. The latter would then be rolled down her toned long legs before she proceeded to drop her lacy black brassiere. Her breasts, exposed and gravity-defying, were every bit as wonderful as he had imagined them to be.

Blair kept the matching thong on as her svelte pair of hands reached around to the back of her neck. It appeared as if she was scratching an itch, but it turned out that she was doing much more. The features of her well-known face became grossly deformed as she yanked the separated layers of skin forward. The balding head of an elderly African American emerged from the floppy mask of Blair. He had seen the man before. He was the homeless old chap Ryan had been feeling sorry for and had regularly been dropping greenbacks into his hat.

Right now, he felt repulsed. And horrified.

“Alfred?” Ryan even knew his first name.

“We meet again, Mr Hobart,” his voice was deep and raspy voice due to countless years of smoking.

“What… what have you done to her?” Ryan asked, almost lost for words.

“The correct question should be; is Blair Waldorf alive and well?” Alfred said before answering, “Of course, she is! Why not? The only difference is that she’s also helping a poor old man having the time of his life - with hers.”

Realizing how turned-off Ryan had been, the former homeless man decided to pull Blair’s face back over his own.

“This is WRONG, Alfred! You need to…” Ryan was interrupted by a sinister thought.

“What, Ryan? Get out of her body? I can do that, sure. But, she’ll remember every single thing after I’ve put her on. She’ll know your deepest and darkest secret, Ryan. And you know what’s worse? This skin-suiting power will never work again,” the replaced-Blair said, crossing her arms under her breasts.

“Skin-suiting power? This is fucking crazy,” the young man said, pacing the room as he cracked his head with all the possibilities. The fact that he did not immediately turn down Alfred’s offer could only mean one thing.

And that gave the twisted Blair a reason to smile. The scantily dressed young lady sat back down on the bench – legs and arms crossed as she waited hopefully for her good friend’s answer. When he finally walked up to her and pulled her into a deep passionate kiss, the homeless man within was triumphant. He took an unnecessary risk by revealing his newfound powers to Ryan. But he just could not help it after witnessing the young man struggle with his feelings – his true feelings, almost daily whenever he saw him on the street. When he had dropped a dollar into his beat-down hat for the very first time, the former Alfred knew that he and Ryan were alike. Besides, the lady who gave him the power had mentioned that he would have to help someone ‘overcome their fear’ if he was to keep holding on to Blair’s life.

Never in his old life, had he kissed another man. But Blair’s desire and memories were guiding him and rewarding him with the most wonderful feelings. Ryan was a great kisser as ‘she’ had found out when he scooped her up with his strong arms before carrying her onto her bed. Her breasts bounced lightly as she was placed down onto her satin crib. The silky fabric felt amazing against her bare skin as she watched Ryan stripped. While he was doing so, Blair rolled her thong down her long legs before flinging them over at her lover. He caught it with his mouth as his 8-inch erection was jutting out from between his legs by now.

There was no hesitation for the former elderly African American as he crawled towards Ryan’s magnificent member. Having to jerk off in the hidden corners of the streets, this would be an unbelievable blessing in comparison as he utilized Blair’s mouth to pleasure the handsome hunk. His coo’s and ahhs served as motivation as ‘she’ started bobbing ‘her’ head over his meat with enthusiasm.

Ryan stopped her halfway. And she knew exactly why. Their passion did not have to end prematurely – not before she had her share of the ecstasy. The thoughtful man lifted her up and off the bed as she rested her arms over his broad shoulders as they kissed deeply once more.

Blair could feel his erection rubbing against her sex as if it were the only thing holding her up in mid-air. The sensation was overwhelming - to be frail and lifted so effortlessly as every part of her body was being aroused. She was eventually lowered onto the bed as Ryan proceeded to bury his head between her legs. His skillful cunnilingus had her fill the penthouse with lewd moans as she tried to stifle herself by covering her mouth with her small hand.

When Ryan knew she was ready, he lined his impressive meat up against her cunt before pushing its glan passed her adequately lubricated entrance. The rhythmic pounding followed naturally – slow and gentle at first before increasing in pace and intensity.

Blair squealed uncontrollably as she came first, followed by a few more mini ‘explosions’ – before Ryan lifted her once more into the air. He gave her a few more thrusts before erupting within her womb, stuffing her full with his seeds.

“I hope this magic or whatever you call it comes with birth control,” Ryan said, panting after throwing himself next to the equally out-of-breath brunette on the bed.

“Don’t be silly! This is not how this thing works… But of course, if that worries you, a gorgeous young lady such as myself always takes her pills,” Blair said.

Any hint that there was a 68-year-old homeless man hidden within that sexy body had seemed to be gone. After a pregnant pause, Blair could tell the uncertainty from her lover’s expression.

“If you’re still uncertain about this…” Blair had not completed her sentence before she was interrupted.

“Did you… wash up before you put her on?” Ryan finally got it off his chest.

Blair giggled before saying, “The skin made by this… ‘magic’, may not be able to keep me from getting knocked up, but it does have some healing powers. It got rid of all the foul odor – lice, fleas, and ticks included. Despite all that, I still soaked myself in the tub with deep-cleansing properties, for hours, before climbing into her,” Blair said before giving him a curious look which was followed by a question, “Why do you ask? Do you wanna see if I can pull my dick out from this lil’ cunt so that you can suck on it or something?”

“Can you?” Ryan asked matter-of-factly.

Blair bursted out laughing. After seeing how disgusted the man had been when she took her face off, it was the last thing she had expected from him. Nevertheless, this had also been a night of discovery. New pleasures were bound to be found. At this point, the new ‘woman’ was up for anything.

Less than a quarter of an hour had passed and the sounds of bodies coming together dominated the lavish residential space once more. If Blair’s parents were to walk in on them right now, they would have passed out from the shocking spectacle of their daughter sodomizing a good-looking man her age, all without the need for a strap-on.

From his facial expression, Ryan was in pure bliss as he was enjoying getting his cherry popped. Despite his age and condition, the former homeless man packed quite the punch where it mattered. He was easily as impressive as Ryan himself with a healthy asset at an easy 8 inches as it slid in and out of his pucker like a well-oiled locomotive. The contrasting complexion against Blair’s snowy white skin somehow turned him on even more as he clenched against her intrusion. Though he was happy to be her ‘sheath’, Ryan was thankful for the lube Blair had dug out from her dresser.

“Are you… ready… to be my… sperm bank?” Blair grunted.

“Ye…yesss… GOD, YOU’RE SO FUCKING HOT!!” Ryan moaned right before the lovely brunette erupted within him and pumped his rectum full of her baby-batter.

**

“Now that we know about Ryan Hobart’s Christmas wish, there’s only one question left to be answered: Who does Ryan Hobart want to become?” Blair mused with a glass of wine between her delicate fingers as she sat in her fancy night dress next to her friend.

She turned her attention from the flickering fire to Ryan’s face in anticipation of his final decision. When she saw the look in his eyes, her heart sank. Despite the wonderful times which they had. Despite the many possibilities with the power, they now possessed. The young man had found it impossible to agree with Alfred’s scheme.

“I’m sorry, Alfred. I… I just can’t,” Ryan finally spoke about what the homeless man had been afraid of.

“So, this is it, huh… Guess it’s time for me to give up the life of Blair Waldorf,” she said.

“I afraid so, Alfred.”

*

**

**A week later**

Blair was too distraught to join the New Year’s party. Being her best friend, Serena was beating herself up for not being there with her when a homeless man ‘invaded’ the Waldorf property. Worst of all, Ryan had been complicit in the crime at first. They were grateful in the end when their once-good friend had decided to come to his senses and turned against the pervert.

While the man named Alfred was in police custody, Ryan was nowhere to be found. There was no reason for him to stick around despite doing the right thing in the end and turning over the home intruder to the cops. He was just too ashamed to face any of his friends right now. Chuck had even threatened to beat him good if he saw him.

“Have you taken the meds from the therapist?” Serena asked, sitting by Blair’s bedside while holding onto her hand.

The noises of the crowds nearby counting down to the turn of the year could still be heard faintly even with the thick curtain drawn.

“What good will the pills do, Serena? I’m calm,” Blair said, smiling at her friend.

“So, you said,” Serena said.

“I AM calmed. Especially now that you’re here with me,” Blair said.

Instead of looking at Serena, she was staring over her friend’s shoulder. There was a sense of malice in the way Blair smiled as if she had just become another person. When the blonde beauty tried to turn around to see what had just been so amusing to her friend, it was too late.

Serena felt the warmth on her pretty face as the glare of the beams shot out of a watch worn by an elderly African American and hit her in the head. The brightness was brief for the Upper East Side socialite before darkness consumed her.

**

Blair had been revitalized by the sight of her best friend’s blonde head caving in as its foundation was evaporating through the orifices. White steam billowed from the unfortunate 21-year-old’s eyes, ears, nostrils, and mouth as her head deflated. The rest of her body followed as the Serena van der Woodsen many teens had admired, collapsed upon the chair where she sat before turning into a lifeless skinsuit along with her trendy attire.

Sitting up on the bed, the supposedly traumatized brunette, was far from it. She was seemingly excited as she greeted Alfred by removing her own face. The visage of Ryan emerged from the split-opened back of Blair’s deformed head as he swung his Blair-legs off from her bed so that he could give the old man a relieved hug.

“Thanks to Ernie, everyone was not aware that the cops had arrested the wrong guy,” Alfred said as he picked up ‘Serena’ and began to separate her clothes from her hollowed skin. “Everyone except us, of course.”

“We’ll have to make it up to him once he’s released, won’t we,” Ryan said, without much of a guilt for his betrayal.

Blair and Serena along with the rest of the Upper East Side’s camaraderie had never recognized his existence despite him having known Blair the longest. With new friends popping up as they moved on, Ryan had been continually fading away into the background. Now that he had become one with Blair Waldorf, she could never ignore him. At the same time, Ryan could live out his dream of turning into a beautiful woman.

Two birds with one stone.

“I’ve promised to keep Jenny, un-skinned and un-worn, just for him. He seems to only have eyes for that young blonde,” Alfred said before climbing into Serena’s highly elastic husk. He had earlier separated her dress and underwear from her skin.

Even though he was malnourished and skinny, to begin with, the discrepancy could not be discounted, especially in terms of their heights. Nevertheless, it was still not much harder than having to wear Blair not too long ago. The flexibility of Serena’s skin rendered by the device made things easier for Alfred as he saw his bony legs toned up to the blonde’s sculpted ones. His hips widened while his boner flattened almost effortlessly as he pulled the lifeless suit further up his body. He could feel his ass swelled up to mimic the young woman’s curves. Speaking of which, the transition from his new hips to his new waist became that much smoother as Serena’s 24-inch returned when Alfred started inserting his arms into the skin’s ‘sleeves’.

At the same time as the rheumatism over his fingers vanished as they transformed into Serena’s dainty ones, the initially deflated sacs puffed up upon his chest and turned into Serena’s perky breasts. The hairy mess over the proximity was no longer visible as they were being masked by Serena’s smooth delicate skin.

Ryan had never considered that the spectacle of Alfred’s head atop a young white woman’s body would arouse him as much as his black cock emerging from a youthful Caucasian lady’s cunt – but it did. Perhaps more so than he cared to admit. He would not feel conflicted for long though, as the fellow body stealer was quick to stretch Serena’s floppy crown over his own balding head. Manual adjustments with his stolen fingers were minimal as the skin would mostly snap into position on its own.

A few seconds later, all there was left for Alfred to do was to lift Serena’s eyelids, and the ‘Princess’ of Constance Billard School for Girls would be revived, amid under a completely revamped ‘management’. Flashes of Serena’s memories, especially her most cherished life events as well as some tragic ones, were recorded into the former elderly man’s mind even before the first ray of light hit his metamorphosed retina.

“So, how does her body feel compared to mine?” Blair asked as if the person wearing her never existed.

“Different, but similar. Kinda hard to put into words,” the new Serena said while swaying her naked hips towards her best friend.

“Guess we’ll have to find out ourselves, won’t we?” The former Ryan said before pulling the newly replaced blonde into a deep kiss.

The passionate make-out session proceeded with Blair’s hand slithering down to paw at her friend’s pussy. She could feel her getting wetter and wetter as Serena reached around to squeeze at the brunette’s derrière in return. It did not take long before she would help her out of her dress and lingerie. Soon, Queen B and Queen S would be eating each other's cunt in the famed ‘69’ position on the same bed where the former had been lying down ‘unwell’ earlier.

The noises of soaking wet slurping sounds occupied the room before it was replaced with feminine cries of explosive orgasms experienced by both girls. Despite having reached the heights of their stolen pleasures, the lesbian lovers determined to go on, until Ryan’s throbbing erection squeezed itself out from between Blair’s pink folds.

Serena promptly improvised from performing the act of cunnilingus to her more familiar skill set of fellatio – at least according to the muscle memories that came with the skin.

“Oh yes! Oh YES! The mouth of Serena van der Woodsen… feels so fucking good!” Ryan grunted using Blair’s voice.

The blonde merely looked up before taking Blair’s cock down her throat without choking. With the process repeated a couple more times, Queen B would eventually cum, shooting a massive volume of jizz down Serena’s gullet. They barely had any time for a breather before it was S’s turn to pitch. And boy, what a pitch it was – shoving her very own hard-on into Blair’s ass in doggy style even when her balls and dick were still dangling between her legs.

While the ‘girls’ were having fun with their dicks out, the door to Blair’s bedroom burst open. Both Eleanor Waldorf and Lily van der Woodsen tumbled into the room. Apparently, the mothers were in the midst of eavesdropping on their daughters before the latch on the door gave way.

“We… were having a conversation when we thought we heard some… peculiar noise from in here,” Eleanor was having a hard time trying to explain the intrusion, especially as she found her daughter in the most compromising position.

“Yea… we thought you girls might need something,” Lily stammered embarrassingly. Her eyes, though, were locked onto the imperious black meat jutting out from her daughter’s crotch.

“How about a couple of well-seasoned pussies to start with… Mom?” Blair said after grinning knowingly at Serena.

Their mothers had just been taken over by two more of Alfred’s pals and fellow derelicts when Serena had been all too concerned sitting by her friend’s bedside. Now that everyone appeared to be in position, the lesbian fling had evolved into a foursome – starting with the daughters giving their lovely mothers a good pounding in a variety of positions. As the night went on, it would be the mothers’ turn to give their daughters’ snatches a good workout by conjuring cocks of their own from their stolen womanhood. The curious abilities seemed to be running in the family after all.

Inconspicuous to these delirious participants, the clone of Professor Eugene Phillips - tucked away within the skin of Vanessa Abrams - smirked up at the window of the Waldorf’s residence. As the snow began falling onto the paths of Manhattan outside, the woman who had gifted Alfred his skinsuiting ‘power’, resumed her chilly evening walk with a camcorder in hand. Even though the turn of the year had come to pass, the former elderly inventor was happy with the outcome of his little ‘experiment. Many Christmas wishes appeared to have been granted along the way.

The End.