Firsts [Open for 1M!]

Hi there! I've been gone from literotica for a few years so I just created a new account to get back into role-playing! I thought I'd start by reviving an old story that I never really got off the ground.

It's the story of Annie Merlyn, a brilliant but inexperienced recent college grad. She's decided to lose her virginity, but her big brother's best friend has some thoughts on the matter.

Character Descriptions:

Annie Merlyn
19, 5'5, 110 lbs
Very petite, delicate features
Fair skin, long blonde hair, big blue eyes, freckles
Brilliant (recently graduated college 3 years ahead of schedule), sweet, has a tendency to babble when nervous

Oliver Weston
26, 6'1, 190 lbs
Lightly tanned skin, sandy blonde hair, blue eyes, strong jaw always covered in stubble
Her brother Derek's best friend, practically part of the family, a good guy, very protective of Annie. Avoids commitment, has never had a relationship, just a lot of hookups with women who "know the score" and would never expect more from him, has been fighting/denying his feelings for Annie for years


Summary:

Annie, his best friend’s little sister, has decided the time has come to lose her virginity. Oliver is so screwed.

Annie has been in love with Oliver West for as long as she can remember. As her big brother’s best friend, she’d known him all her life. He is practically a member of the family. In some ways, she’s closer to him than she is to Derek.

Now 19 years old and recently graduated from MIT, Annie's returned home with a mission. She wants to lose her virginity. It was no secret at school that she was three years younger than the rest of her class, and was underage for the majority of her college experience. No guys would touch her. Those in her class were either afraid of getting in trouble or just thought she was too young, and when she was a senior and guys her age finally started matriculating, they were intimidated that she was so far ahead. Annie has the same hormones as anyone her age, and she’s tired of being treated like a little girl. She can no longer ignore the repressed passion built up inside her. Sure, she’d always imagined her first time would be with someone she loved and had been with for a long time (and if he had gorgeous blue eyes and a grin she’d loved since she can remember, she’d never admit it) but desperate times called for desperate measures. A one night stand would suffice. At least that way if she embarrassed herself she’d never have to see the guy again. And with the promise of sex, chances are good he wouldn’t run off if she stuck her foot in her mouth.

One night, while out at a club (she’s 19 but most bouncers are suckers for a pretty face) Oliver spots Annie and notices the change in her. Wrapped in a short dress with some idiot hanging all over her, she’s never looked more beautiful... or grown up. Noticing the discomfort on her face that anyone else would miss, he chases the sleazy guy off and prepares to give her one hell of a lecture. Before he can open his mouth though, she rips him a new one for treating her like a kid and inadvertently blurts out her naughty plans. Shock is quickly replaced by worry and anger. Her unabashed curiosity and unfaltering boldness set off all of his protective instincts and make it impossible for him to ignore the feelings for her he’s been fighting for years. Feeling protective and possessive, he decides to do whatever he has to to keep her from going to bed with another man. Unable to deter her from her course, he decides that if anyone is going to take her virginity, it’s going to be him.

He makes her a deal. If she doesn’t jump into bed with some random guy, he’ll be her first. But it’ll be on his terms. They’ll start slowly, one step at a time. One day it’s kissing, the next some petting, and only when she’s fully comfortable will they sleep together. Oliver thinks he can handle it, that he can keep his feelings in check and he’s just doing her a favor--maybe even that sleeping with her once will get her out of his system. But it doesn’t work out like he planned and lines become blurred.





Firsts:


Annie sighed as she looked at herself in mirror that made up the wall behind the bar. She let her eyes travel from her mass of lightly curled blonde hair to the faint freckles scattered across her cheeks to the red cocktail dress that clung to her curves like nothing else she had ever worn. Her cheeks burned as she thought of people looking at her in the dress. She bit her lip and cast her eyes around the room, wishing she had worn something a little less daring.


Correction, she thought to herself, The dress is perfect. You’ve just been a prude for so long you can’t handle it.


That was going to change tonight. She’d decided to lose her virginity, and she wanted it to happen immediately.


She drew in a deep breath, the air feeling heavy in her lungs, and took a seat at the bar. She’d been told by friends–all of whom were more experienced than she–that all she’d have to do is sit alone and guys would approach her. The process seemed a bit artificial to her–forced, even–and a knot formed in her stomach. Was this really how she wanted this to happen?


No. But she DID want it to happen. Desperately. And this was the only way.


Suddenly feeling uncomfortable and exposed at the bar, Annie darted another nervous glance around the room, only to find that someone was watching her. He was about her age and extremely attractive, and everything about the way he held himself screamed that he knew it. Seeing her opportunity and knowing she should take it, she met his eyes and sent him a tentative smile.


At that small gesture, he rose from his seat and left his group of friends behind, gracefully sliding into place beside her.


“Hi, Gorgeous,” he said in a deep, smooth voice, accompanied by a confident smile. Inexperienced and distracted by her nerves as she was, she didn’t recognize the intense, predatory nature of his approach and wasn’t prepared to protect herself from creeps. His green eyes captured hers and she couldn’t look away, sensing the impending decision she would have to make.


Summoning calm, she let a slow, knowing–albeit artificially so–smile grace her features and said hello.


With few words, he drew her onto the dance floor with him and let his hands slide low on her hips, pulling them tight against his. Forcing down her discomfort, she let her body rest flush against his and swayed to the music. Every cell in her body objected to this man’s touch but she refused to acknowledge her feelings as legitimate. She would get used to it, she was sure.


She had to.


She focused on the beat and tried to ignore her nerves, not sensing the gaze–slowly shifting from vaguely concerned to enraged–that had been locked on her since she’d walked in the door.


-------------------


Ok, I think I've babbled long enough. If you have any interest in the part of Oliver, let me know! I obviously want plot and romance to be a big part, but also plenty of *adult play time*. I imagine that after they sleep together for the first time, Oliver won't be able to keep himself from offering to show her more. Different positions, different kinks, all kinds of fun things.

Let me know if you're interested!

Oliver had been hanging out with some of his friends for the night. They ended up going to the club. There was no doubt that he had a reputation and he was planning on expanding on that reputation a little bit more tonight.

So far the talent had been only descent. There wasn't too much to be impressed about. Over the course of the next hour, the crowd had started to pick up some. His friend Derek had already bailed, probably trying to hook up with one of his ex's he though as he continued to look.

It took a while but he managed to see someone sitting at the bar alone. Usually that was a sign that he was familiar with. He watched as someone else was familiar with it as well. He moved a bit closer as he saw a guy talk to the girl in the tight red dress.

Oliver took a sip of his drink, finishing it off. As he looked back at the girl in the red dress he noticed something about her. He saw right past her blonde hair, the same spot of freckles that he had seen before. It couldn't be, he thought to himself. He started to make his way closer, seeing the girl come into full view, clearer than before.

Oliver pushed the guy out of the way, catching Annie as she fell back a little bit from losing her balance. "What the fuck do you think you're doing?" Oliver asked the guy sternly. "What, you think you can just dance with her and think she'll get lucky with you?" He looked over at Annie as the guy blew him off and wandered away.

"Annie," he said, "what the fuck are you doing here?" He looked at how she was dressed. This wasn't typical of her at all. "Who are you with? Does Derek know you're out here by yourself?" he looked at her as he waited for her response, hoping she had a good answer to his questions.

The shots Annie had taken earlier to calm her nerves were finally kicking in and she could feel the tension leaving her body. She was still nervous, but the feeling had changed from one of fear to anxious excitement. Her dance partner--Rick or Rich, she wasn't quite sure--had pulled her body flush against his and with every move she made she could feel his leg slipping further between her own and his hard chest teasing her nipples. She'd been dying to be touched for so long that even the smallest graze made her stomach clench and her breath catch in her throat.

Look at yourself her conscience shouted at her How did you become so desperate?

She squashed down the doubt that had been clawing at her--the knowledge that she wasn't the kind of person who could treat sex casually, especially her first time--and focused on mimicking the moves of a far more experienced woman.

She felt like a kid playing dress up--a little girl in her mother's lipstick, pretending to be all grown up.

You're not ready. You don't want to do this.

Or is it that you just don't want to do this with him?

Stubborn as ever, though, she ignored the taunting voice and deliberately rolled her hips against the man in her arms, pushing aside the mental image of her brother's best friend. She'd made her decision and she was sticking to it.

Her partner--Rick, she finally decided--responded by groaning and dropping his head to press his lips into her neck, kissing and sucking lightly before scraping his teeth over the tender area at the base of her throat.

It was then that she felt him being yanked away from her and dragged out of reach. The second she felt arms close around her and heard Oliver's voice she felt her fantasy slip out of reach and the walls of the bar begin to close in. "What the fuck do you think you're doing? What, you think you can just dance with her and think she'll get lucky with you?"

This is not happening, she thought to herself.

She was so surprised to see Oliver there--as if she'd somehow conjured him by wishing he'd been the one she was dancing with--that she didn't even notice Rick wandering off in a huff. Unable to find words, she could only follow dumbly as Oliver wrapped an arm around her and pulled her off the dance floor.

"Annie, what the fuck are you doing here? Who are you with? Does Derek know you're out here by yourself?"

Indignation finally managed to push aside her surprise. That was much better. At least she could work with that.

She planted her heels and refused to follow Oliver any further. "Does Derek know I'm here? Are you kidding me?" she demanded, using her loud voice. She wasn't really one for making a scene, or conflict at all for that matter, but Oliver's high handed behavior set her off, and she couldn't keep the anger out of her voice or wait to talk to him somewhere more private.

"I don't need my big brother's permission to go dancing Oliver!"

"Hey, don't use that tone with me," he said back in a firm tone. "Why are you at a club, underage, with no one else? What if something happened to you?" He continued to hold her arm and walked her back to a quieter part of the club with him. He sat her down in a booth and joined her. "Now, don't try to make a scene, alright?"

He looked her over, a bit surprised that she looked so good in her dress. He thought for a moment before speaking. "So, if Derek or your parents, found out that you were here by yourself and I knew about it, they would fucking kill me after they kill you, right?" he asked. He knew that he was right. Oliver was practically part of their family as it was. "I'm not saying don't go out and have a good time, I'm just saying don't do it alone," he told her in a reasonable tone. "What would've happened if you went home with that guy and he was some sick fuck with some messed up fetish that hurt you?" he asked.

He started to scratch his stubble a little bit before speaking again. "Now, I know I'm not Mr. Upstanding, but I do know that a pretty girl, like yourself," he said as he pointed to her, "doesn't go out dancing alone unless they want to do something stupid. So what kind of stupid are you trying to be tonight?" he asked. He waited for her response as he leaned back a little bit.