PROMPT:27 years, 3 Tonys and Rachel berry hasn't given IT to anyone yet. She's been single since college. She ditches the Tonys after the party to brood over her win and firmly intact virginity at a bar/ lounge/nightclub. She's fed up and vows to give it to the first person who approaches her. Enter Quinn Fabray, owner to personally welcome the hottest celebrity in NY to her place.

Hey guys, I got this prompt from iluvsarasidle a really long time ago and I finally decided to write it. I have no idea what the main story line will be, I have no idea how long I would like it to be, and I have no beta or co-writer.

Also, I have to apologize about my other story {Second Chance at a First Impression}. Due to some circumstances beyond the control my personal life, as well as that of my co-writer, this story is on hiatus. I have every intention of finishing it, but I refuse to do it without my co-writer so whenever we can both get our act together, I promise you we will post something.

For now, let me know what you think of this story thus far. Chapter 2 is already written. Based on feedback, I will know how to proceed with it.

Al mistakes are mine, as well as any inaccuracies/inconsistencies in the story.

Disclaimer: I don't own Glee.

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Chapter 1

Rachel checks the time on her wrist watch. Her manager is drunk on her most recent Tony for the category 'Best actress in a musical'. Or she may be drunk on the free champagne given out at the well stocked bar at the Ritz Plaza main ballroom. Either way, Rachel Berry has just achieved full EGOT status, a mere 4 hours ago. Her manager Kathryn has decided that for once, instead of working hard and being the professional she usually is, when representing Rachel Berry, she will celebrate this milestone achievement of her client.

The Broadway diva has already circled the room acknowledging her peers and accepting heartfelt congratulatory messages. The word "milestone" seems to be the word of the night, and for some strange reason it hits a little too close to home in a not so great way. Rachel is broken from her thoughts when Kathryn walks up to her.

"Rach, wheeere have you been?" she slurs. "This is soooo amazing. I'm totally proud of you. In fact I'm sooo proud of you; I think that we should both get laid tonight." Rachel arches an eyebrow. By this time her manager is slumped on Rachel, while the diva tries to support her weight. "Well... I mean, not together, like you and me, but like, we should find someone each tonight to sleep with." Her manager tries to wink at her in her drunken stupor, but instead ends up closing both her eyes for a good 5 seconds.

Rachel finally speaks, "Katy, I think its home time." She notions for one of her bodyguards to come to her and he gently escorts her manager outside to a waiting car to take her home.

"Will that be all Ms Berry?" her head of security bodyguard asks her.

"Tony, please, call me Rachel. I know you are still technically on probation but my team is my family. I clearly trust you with my life, so why won't I trust you with calling me by my first name?" Tony smiles at the warmth that is the personality of Rachel Berry. "And yes Tony that will be all."

"Ok well let's get you home then." He extends his bent elbow to her which she happily links her arms with his as they walk out the ballroom towards the elevator.

The elevator door dings and Rachel and Tony are now in the main lobby, making their way out on the street.

"On second thought, Tony, I think I'm not ready to go home yet. Are there any night spots in this area?"

"Umm, there is one place about 7 blocks down from here."

"Well can we check it out?"

"You are the boss Rachel. Come on. Hop in."

They drove to the night club called 'VIP Lounge'. There was a neon light just above the door. Rachel opened it and saw that it was an underground night club. She looked at Tony a little apprehensive. He smiled.

"Don't worry Rachel. It's a very classy place. If you want we can go in together and you can see if you like it and if not, we can find somewhere else to go."

"It's ok. I will go in."

"Ok, well you know the drill, we're right outside and you have your panic switch on you?" She held up her car alarm sized remote which had a single red button in Tony's view as confirmation. "Ok Great."

"Thanks Tony."

"Sure thing Rachel."

The petite diva descended the stairs, her body humming from the vibration of the music as she got closer to the entrance. She is stopped at the velvet rope by a tall, well built man.

"Name on the VIP list?"

The brunette begins to fumble with her words because it has been years since she has ever been ask such a question. Being a Broadway star allowed her access to the most elite places in New York City, but for some reason the VIP Lounge didn't make her feel much like a VIP. She was about to turn her back to the bouncer, when a shorter man tugged at his arm and whispered in his ear.

"I'm sorry Ms. Berry, you can pass."

She flashes both men her classic Rachel Berry smile as she crosses the rope. She timidly makes her way across the main room and heads to the bar on the opposite side of the entrance. The VIP Lounge was quaint. The interior d├ęcor was tastefully done and there was one wall made up entirely of a giant fish tank. While taking in her surroundings, she understood why there was a VIP list for anyone who entered. This place was just classy. The owner seemed to run a tight ship because everyone was calm, the music was upbeat but not to the point where the volume was able to drown out your thoughts. There was a spot to eat, a spot to dance and a bar with an oddly shaped counter top.

She pulls a stool at the bar (as close to the fish tank wall as possible) and settles herself in for a long night. Rachel Berry. How would others describe her? Superstar. Talented. Elegant. How would she describe herself? VIRGIN! The brunette ordered a dirty martini and took it in one gulp while tossing her head back.

"Can I have another, please?" the bartender pours her another as Rachel's head sinks lower. She felt like hiding to avoid being spotted so she tried to keep her head low and not face the crowd in the lounge. How did this all happen? She had it all planned out. Broadway star, fall in love, EGOT status, marriage and children, white picket fence, the works. Yet here she was sitting alone at a bar, unable to share her success with a companion, and more notably still a virgin. Most of the relationships she partook in were very short due to her drive for success putting her career before anything and more specifically anyone else. You would think that coming to terms with her sexuality and being open with the press about it ("Rachel Berry, Bisexual Broadway star extraordinaire", was once a headline in the newspaper), would make her have more choices from the lot. Yet it didn't.

Her virginal status meant that not only has she not had sex ever, but she never came close to it because she never felt like she could fully trust anyone she met on an intimate level. Apart from her ambition getting in the way of sex, there was also the fact that she was a girl who believed in being in love in the movie-type kinda way. Someone taking the time to know you and trying to be your everything. Finding someone as old fashioned as that in the fast paced life in Ney York city was just almost impossible and after a string of short, non-intense relationships, the diva decided to postpone the hunt for love and focus on her career. Here she was now, totally famous, totally accomplished and totally alone.

After emptying her 4th dirty martini, the diva decided to make a vow. She turned her back to the bar and faced the open floor scrutinizing the crowd. The place was a respectable establishment and the patrons were well dressed and classy in a non-douche bag type vibe. With that astute observation, Rachel decided that tonight was the night to get her v- card swiped. Since she knew she could have her pick of anyone, she decided to throw caution to the wind and let fate decide who the lucky person should be, (or unlucky person, since she had no idea how her performance in bed would be on her first time). She closed her eyes and cringed at the thought of bad sex with a stranger, but knew it had to be done.