Happy New Year! Let's all just pretend this was posted 3 days ago ;3

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“I can’t believe you talked me into this…” Ryan pulled at his dress’s straps in an attempt to keep what little modesty he could while he complained. Sitting across from him in the back of the limo, leaning forward with his arms resting on his lap, was Ryan’s old college friend Julian who stared smugly at him, face full of amusement as he leered at Ryan’s body.

“I didn’t talk you into anything.” Julian retorted. The corner of his lips curled upward with the same smug smirk he’d given Ryan many times already today as his gaze broke away from Ryan’s chest to meet his eyes. “You came to me, remember?”

“Hmmph!” Ryan puffed up his cheeks and crossed his arms over his chest as he turned away from Julian to stare out the limo’s window. “You didn’t have to make me wear such revealing clothes though.”

Julian was right, though. Ryan was the one who approached him, but he didn’t think it would turn out the way it did. Back in November, Ryan ran into a string of bad luck that quickly went from bad to worse. He lost his job due to layoffs, and without any income he fell behind on rent and was evicted, causing him to lose everything except what he had on his own back and whatever he could fit into his car. With no family on this side of the country, the only person he could reach out to for help was Julian, who seemed a bit too eager to help over the phone, but Ryan was desperate and needed somewhere to stay until he got back onto his own two feet. Ryan knew Julian came from a rather well-off family when they met in college, but as he turned down the street, passed through the front gate, and drove up the path to the multi-million-dollar luxury home, he realized just how wealthy Julian’s family truly was. After heading inside and catching up with his old college friend, Julian dropped all pretenses and laid out his offer. Ryan would get to live with Julian and have all of his needs taken care of, but in exchange he would have to become a woman and pretend to be Julian’s girlfriend the entire time. Julian explained that his parents had given him an ultimatum: either he got into a serious relationship with someone, or they wouldn’t let him inherit the family business. It was a difficult choice, but with nearly nothing left to his name, Ryan agreed, allowing Julian to inject him with the special serum he had acquired for just this occasion and to begin playing the role of Catherine, Julian Whitmore’s doting girlfriend.

The serum was rather fast-acting, turning Ryan from an average 5’10” man into a drop-dead gorgeous, 4’11” woman. Of course, that wasn’t the only thing to note about his transformation. He knew rich folk tended to have… strange and unique tastes, but it seemed like Julian had a particular fondness for breasts, as two perfect boobs, perky yet with enough sag to see that they were 100% natural despite being more than three times the size of Ryan’s own head, weighed down on his chest and pulled down on his shoulders. Ryan didn’t even get a chance to really get acquainted with his new body, as Julian already had a task for him as his new girlfriend. Being New Year’s Eve, Julian was expected to attend his parents’ yearly lavish party, celebrating a year of growth and profits while making business deals with their guests for the new year, and of course Julian just had to arrive with his new girlfriend. Julian had Ryan whisked away by one of his female house staff to get him ready for the party, where he’d be stripped down to his nude and dressed up in a gorgeous yet incredibly revealing red cocktail dress, its neckline drooped down to his navel, framing his completely exposed cleavage. Following the dress came the hairdressing, makeup, jewelry, and a crash course on proper etiquette for a party of this manner, and before Ryan knew it he was dolled up and out the door, riding in a limousine with Julian to the New Year’s Eve party.

“Looks like we’re here.” Julian announced as their limousine pulled up to an opulent hotel. “Do you remember how you’re supposed to act?”

Ryan rolled his eyes at Julian’s frankly patronizing question. “I do.” Julian sat across from Ryan, hand on the car door’s handle ready to get out yet he stayed where he was, obviously not happy with Ryan’s answer. “Yeah,” Ryan puffed out an annoyed sigh before counting the specific words Julian had given him previously on how he was to behave on his fingers, “Doting, touchy but not too touchy, reserved, and stay by your side.”

“Perfect. I’ll go grab the car door for you ‘Catherine’.” Julian shot a teasing wink Ryan's way as he opened the door and stepped out of the vehicle.

It wasn’t a long wait but Ryan still found it a bit awkward to simply sit in the limo waiting for Julian to be a ‘gentleman’ and open the door for him. After Julian opened the door he bent slightly over and offered his hand to Ryan to help him out of the car, which Ryan accepted. In one smooth motion Julian, with his hand never leaving Ryan’s hand, went from helping Ryan out of the car to holding his hand as they stood side by side one another and began making their way into the hotel. As they walked Ryan couldn’t help but look up at Julian. His college friend had always been taller than him but being well over a foot shorter than Julian made him look a bit more imposing while making Ryan feel a good bit more vulnerable. Once inside Julian led Ryan through the lobby and over to the elevators where a bellhop was stationed.

“Good day sir. Good day ma’am.” The hotel employee greeted them with a brief neck bow. “To which level shall I escort the both of you?”

“Floor 56 please.” Julian answered as he slipped the bellhop a crisp $20 bill from his breast pocket.

“Ah yes, the Whitmore’s New Year Reception. May have your names please?”

“Julian Whitmore and,” Julian let go of Ryan’s hand and instead wrapped his arm around his back to grab his shoulder and pull him closer to his side, “this is my plus one.”

“The young Mr. Whitmore.” The bellhop repeated back to Julian. As he did he stood up just a bit more stiff than he already was and held the door to the elevator open for them. “Let me get you up to your parents' reception right away then.” He stepped inside after Julian and Ryan, inserted a key into the elevator’s panel, and pressed the button to take them up to the top floor. The door opened up, not to a hallway of identical rooms but to a large, bustling, party where everyone was walking around and mingling with one another. “Here we are. I hope you and the missus enjoy the reception. Please feel free to call the front desk if you need anything.”

As soon as the two of them stepped off of the elevator a woman off to their right excitedly called out to them. “There’s my boy!” A short, pudgy woman in a cream colored pantsuit who looked to be in her late forties hurried over to the elevator and threw her arms around Julian. “I’m so glad you could make it!”

“I am too Ma.” Julian returned the hug, albeit a bit hesitantly as his mother squeezed his torso with an iron grip. “I uh… have someone I’d like you to meet actually.” His mother immediately let go of her embrace as Julian said that, allowing him to step to the side and gesture towards Ryan. “This is my girlfriend, Catherine.”

“Oh! Oh my!” His mother’s eyes went wide, assessing ‘Catherine’ from her head to her toes but ultimately settling on the unabashed chest of the woman meekly waving at her. “You didn’t tell me you were bringing a guest Julian! I- Where did your father run off to? He’s not going to believe this- that you have a lady friend!”

“It’s fine Ma. I’m sure he’s busy with other guests.”

“You’re right, but-” Julian's mother took a step closer towards ‘Catherine’ and held out her hand. “Where’s my manners? It’s nice to meet you Catherine. I’m Julian’s mother, but you can call me Debby.”

“It’s nice to meet you Debby.” Ryan went in to shake her hand but as soon as his hand touched Debby’s he was instead pulled into a hug from the older woman. “I can’t believe a woman as gorgeous as you settled for someone like my little man!”

“Haha…” Ryan hesitantly returned the hug but his body language clearly showed how uncomfortable he was by this exchange. “He’s a surprisingly… sweet man.” He was finally released from the surprise hug when Julian’s mother again directed her attention towards her son.

“Well I won’t spoil the surprise for your father. Why don’t the both of you enjoy the party and get to mingling. You’re gonna want to get cozy with some of these fellas if you’re gonna inherit the family business you know.” She playfully nudged Julian with her elbow as she said that last part. “I’m gonna go find your father and tell him you’re here though. You know how he is, he’ll come say hi to ya eventually.”

The both of them watched Julian’s mother scurry off to look for her husband, leaving Julian and Ryan to themselves once again. “She’s a… colorful character.” Ryan blurted out as he adjusted the front of his dress.

“You can say that again.” Julian let out a soft laugh before wrapping his arm back around Ryan’s shoulder. “I guess we should go mingle and enjoy the party then.”

Julian led Ryan around the lounge, stopping occasionally to greet old acquaintances and show off his girlfriend to everyone. Ryan got a lot of looks of jealousy thrown his way from both men and women alike but nothing was as bad as the shameless perving stares from a lot of the older men who Julian had to unfortunately cozy up to, seeing as they were business partners of his parents. While they walked around they’d occasionally get interrupted by a waiter or waitress offering them an assortment of finger foods that Ryan had never had before in his life. Oysters, caviar toast, crab-stuffed mushrooms, mini quiches, and even beef wellington bites were just some of the many delicious foods that Ryan got to enjoy while he got paraded around. That wasn’t including the many glasses of wine and champagne that he had downed throughout the night, which might have been a mistake with his smaller body as the alcohol hit him hard. He wasn’t really aware of when it happened but at some point he went from just holding hands with Julian to practically leaning on him as he pressed her chest onto his arm and rested her head against him.

“Wow, would you look at the time!” Julian suddenly exclaimed as he checked the watch on his wrist. “It’s almost midnight.” He gently pulled his arm away from Ryan, out from the warmth of his cleavage as he continued. “I’m going to head to the bathroom real quick before it hits midnight. Mind grabbing us some champagne and waiting for me on the balcony?”

“Yeah! Sure thing.” Ryan answered. He watched Julian head off in the opposite direction from the mini-bar, disappearing into the crowd before heading over to grab the both of them a drink to cheer the new year with. After ordering the drinks and rejecting the bartender's advances he made his way out onto the balcony to wait for Julian to return.

“Here she is,” Ryan made out the familiar voice of Julian’s mother from behind him, “go and introduce yourself.”

Ryan felt a rough tap on his bare shoulder and turned around to an older man who was taller than even Julian was and looked unamused. “I was told you were Julian’s girl?”

Ryan had to strain his neck as he looked up at the older gentleman. “Yeah,” Ryan gave a half nod, “I’m Catherine. You must be Julian’s father?”

“Mmm hmm.”

“Oh! Well it’s a pleasure to meet you I uh…” Ryan looked at the two glasses occupying both of his hands. “I’d offer you a handshake but my hands are full.”

“That’s fine.” Julian held a hand up. “So what do you do? Insurance? Automotive? Oil? Or do you come from one of them new tech industries?”

“Well I uh… you see…” Ryan stammered. Julian never told him what to say if he was asked something like this. Maybe he planned on being present so he could jump in and speak on Ryan’s behalf but-

“David!” Julian’s mother turned and looked up at her husband as she began to scold him. “We shouldn’t be asking that sort of stuff already.” She then turned to ‘Catherine’ and spoke to her directly. “I’m sorry about that. Let’s change the subject like… How did you and Julian meet?”

“We met in college actually. We both had the same finance class and we just really hit it off with one another.” Ryan’s answer wasn’t necessarily not true. He did meet Julian in college in their finance class and they did get along quite well. It was just… Ryan wasn’t a woman back then and their relationship was much more platonic than his parents assumed.

“Aw! That’s such a cute way to fall in love!” Debby gushed. She then grabbed David’s hand and pulled him closer to herself as she continued. “Davey and I met when our parents arranged for us to be together. I’m sure lucky I got a sweetheart like him and didn’t get stuck with that Harvey fellow.”

“Oh!… That’s uh… that’s…” Ryan was struggling to find an appropriate way to respond to what Debby just said. As he stammered and tripped over himself a sudden pair of hands reached around from behind him and pulled him close, looping one arm over his dress while the other arm snuck its way under his dress.

“I see you met Catherine dad.” Julian rested his chin on top of Ryan’s head who, from both being a bit drunk and suddenly being held so intimately, was red in the cheeks, flustered and embarrassed as he stared down at the ground. “What did I miss while I was gone?”

“Catherine was just telling us how you two met!” Debby again took it upon herself to answer. “You didn’t ever mention meeting a girl in college.”

“We just wanted to keep things between the two of us before we were sure we were serious. Isn’t that right Catherine?” Julian looked down at Ryan who was still staring down at the ground.

“Y-yeah…”

“So…” Debby silently counted on her hands, “you’ve been with each other for… 5 years now?”

“That sounds right.” Julian nodded.

“Oh ho!” Debby practically chortled with excitement. “So does that mean we’re gonna have grandbabies soon?”

“Mom!” Julian furrowed his brow at his mother while Ryan’s face became even more flushed and red.

“I’m kidding. I’m kidding. But your father and I do want to be grandparents someday. Isn’t that right David?” Debby looked up at her husband who just gave her a shrug for an answer. “Anyways, if you both are serious about this relationship I think I can arrange something for you Catherine. Do you currently have a job?”

“I uh… no.” Ryan shook his head.

“Splendid!” Debby let go of Dave’s arm and clapped her hands together. “I know a lady who has been looking for a model and I think you would be just perfect! And being a lingerie model for a designer brand like hers, whoo let me tell ya you will be making quite a lot of money with how popular you’ll be.”

“I don’t know, that’s…” Ryan’s head was spinning at this point. This whole arrangement he had with Julian was already getting so out of hand and he had no idea how to respond.

“I think that’d be great!” Julian answered for Ryan, giving her a quick squeeze as he did so. “It would give you something to do rather than sit at home all day.”

“I… guess so?”

“Great!” Debby exclaimed. “I’ll send Julian her number so you can get in contact with her.”

“Oh! Uh… Thank you.”

“Anyways,” Debby continued on, swapping the conversation elsewhere, “We’ve probably bothered you both enough already. Dave and I still have quite a few guests to talk to tonight so we’ll leave you be. It was a pleasure meeting you Catherine.”

“It was a pleasure meeting the both of you as well.” Still being held by Julian and still having his hands full with their drinks Ryan could only give a weak smile and nod his head as Debby and Dave went back inside.

“Seems like my parents like you. Well… at least my mother does.” Julian chuckled, squeezing Ryan even tighter, lifting his arms and Ryan’s breasts up as he did so. Just then it turned to midnight as people around them cheered and fireworks blasted off into the sky.

Ryan didn’t know how to answer. Maybe it was the alcohol or maybe he just needed time to comprehend what the hell had happened today but his head felt like it was spinning. Worse than that he felt an odd, thrumming heat pulsing in his lower gut. If it wasn’t for Julian’s warm body wrapped around his he wouldn’t have felt grounded in this situation, his sense of scent was overwhelmed by Julian’s pleasant cologne, and the exploding fireworks rattled him back to a stable point. What the hell did he get himself into?