Pairing: Brittany/Santana; side Kurt/Sam, Puck/Rachel; mentions of Will/Rachel
Rating: Nc-17/M
Disclaimer: I do not own (the train wreck that is) Glee.
Summary: She's famous, she's rich and she has hot-shot actor Sam Evans as her boyfriend. In short, Brittany Pierce's life appears to be perfect. Except most of it is a lie. How will the decision to let loose a little change her life? What will happen when high-class escort Santana Lopez unintentionally steals her heart?
Warning: smut, g!p Brittany, hooker!Santana
A/N: The idea for this story came from a prompt at the GKM. I saw it and just had to write a fill. This will be a multi-chapter fic, rotating between Brittany and Santana's POV. If things work out the way I want them to, there will be weekly or at least biweekly updates. So have fun reading! And don't forget, this is a GKM fill first and foremost, so later chapters will have lots of sexy times.

I want to say a quick thank you to the following people: The anonymous prompter, whose idea I'm allowed to use (really, it's golden); Howaboutno, who not only coaxed me into writing this story but is also cheering me on and helping me keep the plot in check; Theveiledfairy for beta-ing this story and making it sound so much better; my faithful readers, you guys are simply amazing.

Brittany Susan Pierce had it all. She was young, she was talented, and she was the most amazing performer this generation had ever seen. Some even deemed her the next Beyoncé. A rising star born to live on the stage, she had taken the US by storm. Her first single Duck in the Hat had been a real zinger, staying on top of the charts for eight weeks. She'd been nominated for several VMAs, including Best New Artist and Best Female Video, which she ended up winning.

Now, almost two years later, the barely twenty-one-year-old performer was planning her first US tour. She had just released her second album Unicorn, which, of course, had been a hit. The over nineteen million sold copies worldwide confirmed her success.

Yes, Brittany S. Pierce was definitely one of the biggest artists in the world right now.

Girls wanted to be like her while boys wanted to be with her. Fans stayed out in the cold for hours at the various locations she'd been reportedly spotted this past winter just to get a glimpse of her. Her fan-mail literally exploded with people telling her how much they loved her. It was insane.

To Brittany, the attention was flattering. She worked hard to stay on top and all the love she received gave her even more reason to improve. Not only did she work like a maniac, but she also made sure to show her fans just how much she appreciated their support. At least one twitter video a week was made and released to keep her fans updated. She did little Q&A's from time to time, signed as many autographs as she could, and took pictures with fans until her manager and best friend Quinn Fabray was forced to pull her away.

It also came as no big surprise when her PR team, after weeks of press speculations, confirmed the rumors of her dating hot shot actor Sam Evans. After all, they seemed to make the perfect couple. Young, successful and ambitious; a perfect match.

To most people, it certainly looked like Brittany was on top of the world. However, the truth was, she was far from the happy, carefree girl the public got to see. Only a few chosen ones knew about her true feelings and about the dark secret she was keeping from the world; a secret so shocking that it could destroy her whole career.

Brittany Susan Pierce was not your average girl next door, not when it came to her anatomy. While she had two very perky and well-shaped breasts, the lower part of her body, or more precisely her lady parts, were actually not very ladylike at all. Brittany had been born with a penis and testicles instead of a vagina, which made her, in her opinion, a total freak.

She and her team did their best to keep it under wraps. From specially designed underwear to the absolute ban of bikini or lingerie photo shoots, they did everything to make sure not a word was getting out. Contracts bound those who knew to absolute silence and a copious amount of money was paid to the only girl who had ever seen Brittany's addition.

Back in her junior year of high school, she had found a nice girl who seemed to reciprocate her feelings. Tina Cohen-Chang had been funny, considerate, and beautiful in every way, but when Brittany had told her about her secret and showed it to her, she'd learned that people weren't always the way they appeared to be. Under the surface, Tina wasn't any different from all the other students in high school longing for popularity. Under the surface, she was just as ugly as everybody else.

Tina had called her a freak, a sin against nature, and more cruel names Brittany didn't care to remember. It had only been the simple fact that no one would've believed her that Tina had never told anyone about what she had seen. When Brittany had gotten famous and let Quinn in on the whole story, her manager made sure that Tina would never go to the press.

But even Quinn couldn't turn back time. The damage had been done and Brittany rarely let people in anymore. Besides her family, a few chosen people of her team, Sam, Quinn, Kurt, and Noah "Puck" Puckerman, her bodyguard, were also aware of the fact that she had male genitalia.

Sam, who had a secret himself, was picked as Brittany's beard once her career really took off. He's gay, as is Brittany, so they really were perfect for each other as far as faking a relationship went. Naturally, hiding their respective secrets together made them grow closer. They became friends over the course of their arrangement, which was verging on its one year anniversary, so at least something good had come out of this lie they were living.

However, while Brittany was still wary about finding someone to love, Sam had actually gotten his happily ever after when he met Brittany's personal shopper, Kurt Hummel. It was something of a modern fairy tale come true. Even though it was a secret romance, it was the most beautiful thing Brittany had ever seen in her life and she wished that someday, she would experience something similar.

Sam didn't seem to mind that Brittany was different one bit. If anything, he treated her like one of his "bros", subtly checking out women with her and commenting on them. It gave Brittany a sense of normality, which she desperately needed. After all, being a superstar was exhausting and even more so for someone who had so much to lose.

Because of all this, it was no surprise that Brittany was still a virgin. Don't get her wrong, she was very frustrated about this fact, but what was she supposed to do? Listen to Quinn and start dating a woman, only to have her flee the room as soon as she came clean about her anatomy? That didn't sound like a good plan.

Puck, on the other hand, suggested a different approach to solve this problem.

"Why don't you pay someone to...you know, blow off some steam? I know a lot of famous people who are doing exactly that." Puck jumped on the counter in Brittany's kitchen, then grabbed for a beer and uncapped it. "You have the money, so why not?"

"Why not?" Quinn asked sarcastically before Brittany could so as much think about his suggestion. "If this leaks to the media, then she's done. A celebrity who enjoys the company of prostitutes? It's like a death sentence to her career, trust me."

"I agree," Kurt chimed in from his position in front of the stove, where he was stirring self-made tomato sauce to go with some pasta. "It would be social suicide."

Puck took a long swig of his beer and then replied, "No one has to find out, though. I've been working for other stars in the past and I have plenty of friends who also work for famous people. All I have to say is, if Brittany wants some action without anyone getting wind of it, I know where to go."

While Quinn started to argue with him, Brittany took a moment to let the idea sink in. Sure, it sounded potentially dangerous and could damage her career beyond repair, but Puck kept talking about this supposedly very discreet arrangement. He was really convincing, Brittany had to admit. The only thing that bothered her was that she thought no one should have to pay for the first time they had sex. But with every passing day, Brittany was becoming more and more aware that channeling her sexual frustration into her dancing and singing wouldn't work forever.

Like any other person, she, of course, resorted to taking care of herself from time to time, especially after a long working day. It helped her relax, but it was never fully satisfying, as if something was missing. And sometimes, no matter what she tried, she just couldn't get herself off.

"I think it's a good idea," Brittany suddenly heard Sam interjecting. "I mean, come on, Brittany needs to relieve some tension. So I'm with Puck on this one. Why the hell not?" At that, Kurt raised an eyebrow at him to which Sam simply shrugged.

Sighing, Quinn walked over to the kitchen cupboard to retrieve five plates. "I still think it's risky," she reasoned. "But I guess it's not my decision to make."

A second later, Brittany found herself being stared at by four pairs of curious eyes. Her face took on a deep shade of red and she quickly busied herself by opening the fridge to get a bottle of apple juice. However, she knew that she couldn't escape the discussion for much longer.

"I-" she finally stuttered. "I don't know, okay?"

"Of course you do." Puck smirked. "You just don't want to say it out loud."

Brittany turned to him, her shoulders slumping. "Fine, I-" she paused, putting down the bottle in her hands in order to bring them to her face. Stroking her hands over her closed eyes and cheeks, she cautiously admitted, "I think I want to try it."

"That's my girl." Puck jumped down from the counter to pat her on the back. "Trust me, you're going to love it. I will arrange everything for you. Don't worry. All you have to do is be there when the time comes and pay the bill, of course."

"I can't believe this is actually happening right now." Kurt shook his head as he put the pasta on a few plates before pouring sauce over them.

"Me either," Quinn sighed, taking a plate and a fork. Together with Kurt, she made her way to the living room, leaving the others alone to further discuss the matter. She knew that eventually she would have to get involved to make sure Puck wouldn't mess this up, but tonight was a work free evening, one she didn't want to spend worrying.

"I just know this will end in a catastrophe of epic proportions." Kurt took a seat next to her on the big sofa, practically stabbing his fork into his dinner in a gesture of frustration. "And I can't believe my boyfriend is encouraging this."

"Well," Quinn said around a mouthful of pasta. "I can see why he does it. Brittany could really use a distraction. I mean, have you seen her dance lately? Every time she so as much thinks she missed a step, she freaks out and gets angry at herself. It's not healthy." Then, after taking a moment to sort her thoughts, she added, "All I have to do is keep an eye on Puck's planning and I'm sure everything is going to work out just fine. Brittany deserves some happiness."

Kurt had to snort at that. "But what kind of happiness would that be? She's going to have to pay someone to make her happy. And I don't know about you, but to me, that doesn't sound like true happiness."

"It's easy for you to say," Quinn retorted, suddenly feeling the need to defend her best friend. Sure, this wasn't the ideal way of dealing with the situation, but Brittany had the right to decide for herself how she wanted to live her life.

"You've been together with Sam for nine months now. Not to mention that you don't have to deal with a condition like Brittany's. She's doing her very best, so how about you show some compassion instead of judging her."

Heaving a sigh, Kurt put his plate down on the coffee table. "I know, I'm sorry," he glanced at Quinn, his voice sounding genuine. "I guess I just don't like the idea of Sam getting involved in this. He better not cheat on me with an escort."

"He wouldn't," Quinn chuckled. "But if you ever get suspicious, we'll find a way to check his bank accounts," she added nonchalantly, earning herself a surprised look from Kurt.

Meanwhile in the kitchen, Puck was telling Brittany everything he knew.

"So there's this dude. His name is William Schuester. Basically he's the boss of an escort agency that specializes in catering to the...specific needs of celebrities. Like, the men and women working for him have to sign contracts and all that stuff. Also, you have to have your doctor run tests on you first before you get accepted as a client. It's to prove that you don't have any STDs."

"Um," Brittany replied, dumb-founded. "Okay...but what about my condition? Isn't that, like, the perfect reason to get rejected or something?"

"Nah..." Puck shook his head. He stuffed some pasta into his mouth and washed it down with a gulp of his beer. "I know Schuester. He wouldn't do that, at least not if I talked to him. My friend Finn Hudson is working for him as a bodyguard. One time he gave both Finn and I a free night with two of his girls. It was awesome. Lots of champagne, expensive lingerie, and the best thing: no condoms."

"As if you ever use a condom," Sam fake-coughed.

"What, man? I just don't like the feeling of it. It's as if someone is gagging my wiener," Puck replied defensively.

Brittany furrowed her brows in confusion. "Is that true? Does it really feel that way?" she queried. "Because then I don't want to use condoms either."

"Oh this is just great," Sam muttered. "Please don't listen to him, Britt. He's talking complete bull."

"Hey, why you gotta hate?"

The next few minutes were spent discussing the pros and cons of various contraceptives. Puck explained that every woman working for Will Schuester was on the pill. The guy knew what his clients wanted, so he gave it to them. After all, those people were paying a lot of money for the sex.

"Ten grand a night?" Sam almost spit out his beer. "Ten freaking grand for one night?"

"Yeah," Puck shrugged. "It's really exclusive. Schuester has this huge building with about twenty apartments. Each one of them is furnished with all kinds of expensive designer stuff or whatever. They also have special cupboards with sex toys, but nothing too kinky. Mostly stuff like blindfolds, silk bonds, strap-ons, and some small butt plugs. That's about it."

"And you are sure you've only spent one night there?" Sam asked with a hint of sarcasm.

Puck shrugged again, then searched the fridge for another beer. "I just made good use of my free ride, that's all."

"Yeah, I bet you did."

"And you are really sure they won't reject me?" Brittany finally mustered up the courage to speak again.

"The only reason they could possibly reject you is if none of the girls would want to sleep with you." Upon seeing the hurt look on Brittany's face, Puck hastily added, "But don't worry, that's not gonna happen."

Brittany managed to smile at him, but it was a weak one. What if all the women rejected her? She couldn't possibly think of something more degrading. Brittany suddenly started having second thoughts about the whole thing. There was just so much that could go wrong. She could embarrass herself in so many ways, not to mention that her secret could get out.

"Stop overthinking this." It was Sam who snapped her out of her trance. "We're going to do this. You are going to do this. Tomorrow, we're gonna make you an appointment with doctor Abrams. Then Puck will talk to Schuester."

Still feeling a little conflicted, Brittany rubbed the palm of her left hand against her forehead. "Okay, fine. I'll do it." She knew the situation she was in wouldn't get any better any time soon. So why not try something new? Even if it was risky, even if it was probably not going to end well. At least she could say that she had tried.

"It's settled then." Puck grinned from ear to ear. "You're going to get laid." He wriggled his eyebrows suggestively, making Brittany blush while Sam started to laugh. "Now, tell me more about your perfect image of a woman. I pretty much already figured you prefer brunettes. What else?"

"Am I really in a position to choose?" When both Sam and Puck gave her their come on, now look, she surrendered. "Yeah, definitely dark hair and she should also be a bit smaller than me, but that's all."

"Noted." Puck finished his second beer and placed the empty bottle back on the counter. "Let's go and tell the others about it. I bet Quinn is already itching to boss me around."

And so it was decided. The following day, Brittany paid a visit to Artie Abrams, her doctor, for a thorough checkup. As soon as she got the results back, she made Abrams write her a letter to testify that she was healthy. Then she handed it, together with some copies of bank statements, to Puck and Quinn, who contacted Schuester.

Before she knew it, Brittany found herself sitting in a limousine outside a beautiful building. She had to admit that she was impressed. William Schuester's agency was located in the Upper East Side of Manhattan, actually not that far away from her own apartment. A bellboy was standing in front of the entrance, ready to open the massive glass door to visitors.

Puck almost pushed her out of the limousine. She barely had enough time to put on her sunglasses before she was being dragged toward the entrance. Nodding at the bellboy, they headed inside with Quinn in tow. Down at the reception, a young woman with the name tag 'Rachel Berry' greeted them and said that Mr. Schuester was already awaiting their arrival.

Entering the elevator, they made their way to the 10th floor and not two minutes later, found themselves standing in front of Schuester's office.

"Ahh, Miss Pierce," Schuester opened his arms in a gesture of greeting. "It's a pleasure to meet you in person. I am such a huge fan of your work. Your new single Acceptance gave me chills." He shook Brittany's hand enthusiastically, then moved on to Quinn and Puck.

"Come on in and take a seat." Leading them towards his desk, he sat down on his office chair while the other three moved to sit across from him.

"Thank you for your kind words, Mr. Schuester." Brittany did her best to appear reputable, showing her best manners.

"Feel free to call me Will."

An awkward silence was about to settle in, but luckily Quinn knew how to handle the situation. "So Will, I know we talked about this on the phone a few times, but I wanted Brittany to hear the good news from you in person."

"Ahh, yes," Schuester smiled. "Well Brittany. I hope I'm allowed to call you by your first name?" When Brittany nodded, he continued, "I am very pleased to tell you that you can now consider yourself a client of Schuester & Rhodes."

"Really?" Brittany asked in disbelief. Sure, she had guessed from Quinn and Puck's expressions that she had probably been accepted, but it still sounded too good to be true.

"Yes," he confirmed once again. "I have to admit that when Puck first told me about your..." he trailed off, obviously searching for the right way to put his sentence. "Well, when he first told me about your problem, I wasn't so sure if any of my girls would agree to entertain you. However, after a brief talk with the one girl that fit your criteria best, she appeared to be okay with your condition and is willing to meet you whenever you want. Actually," he opened the top drawer of his desk to retrieve some papers. "She's already signed the contract your manager, Quinn, sent to me. So did I."

Schuester handed both contracts to Quinn, who flipped them over to check the signatures.

"That was fast," she said, a little in awe.

"Here at Schuester & Rhodes we do anything to please our clientele...literally." His laughter echoed through the office, Puck's soon joining in. "All I need now is for Brittany to sign a contract in return, where she commits herself to the payment arrangement and accepts the general rules while also agreeing to never waste any words on this agency's nature to others."

Quinn took the contract from him, reading it through twice before giving it to Brittany so she could do the same. While Puck and Schuester engaged in some small talk, Brittany signed the paper and pushed it back across the table.

"Great, I will have Rachel make you a copy of this and then you are good to go," he addressed first Quinn, then Brittany.

"Rachel will also be the one to schedule your meetings, so it's best you talk to her right away and make your first appointment." Standing up, Will walked around his desk to shake Brittany's hand again. "A pleasure doing business with you, Brittany."

After bidding their goodbyes, the three of them left Schuester's office again. When they had made their way back to the first floor, Rachel printed out a copy of the contract for Quinn before opening up the calendar on her computer to arrange an appointment.

"The first available date would be next Friday at six o'clock, apartment twenty-two on the 8th floor," Rachel told her.

"She'll be there," Puck spoke up before Brittany, who was looking even paler than usual, had a chance to backtrack.

This was actually going to happen. Brittany was still pretty much in shock. She was basically running on auto-pilot right now, since her brain had taken its leave a good fifteen minutes ago. She was excited, but she was nervous. To sum it up, she was a hot damn mess.

However, before Quinn and Puck could lead her out of the building, she had to know one last thing.

"What's her name?" she asked Rachel.

With an understanding smile, Rachel replied, "Santana. Santana Lopez."