Her Best Friends Dad

Author's Note: This story could arguably belong in several categories, including First Time. It's got a sexy alpha male who is much older than the young woman whose virginity he takes, so it could have gone in the Mature category. Because they know each other outside of the situation and she balks a little at first it could be considered 'reluctant' and have gone in the Non-Con/Reluctance category. I decided to go with First Time because I felt that out of all three, that's what it was mostly about. Enjoy!

******

Peter's first thought was "What the hell?"

The website wasn't precisely legal, basically an online whore-house, one that he'd frequented ever since his marriage had broken up once the kids were in high school and old enough to have a bit of their own independence. It wasn't that he couldn't get a date if he wanted, but he didn't want. Too much work without an ensured reward. The website provided him to pick out exactly what he wanted for a night – brunette or blonde, kinky or vanilla, big boobs or little – and know that they'd be clean. There were different location branches and he was lucky enough to live an hour away from one of them.

The ex had the kids this week and he'd decided to check out the website and see if there was anything knew.

Boy was there.

He'd recognized her immediately of course – how could he not? She spent almost as many weekends at his house as his daughter had over the past year. Just turned eighteen last month if he remembered correctly; they'd been talking about her birthday party. Petite at 5'4", short blonde hair that brushed her shoulders, sparkling green eyes, high breasts that were probably somewhere between a B and a C cup, tiny waist, and the sunny smile that marked her as the cheerleader that she was.

Cyana Walters, his daughter's best friend since her freshman year of high school.

Selling her virginity on the internet.

The bidding was open till midnight.

If he'd been a different kind of man he might have bid in order to save her from herself. Save her from whatever she thought she was doing. But over the years he'd found that he didn't care what kind of stupid decisions other people made as long as it didn't affect him or his kids. Why should he? And at least he'd be a better option for her than a lot of the other guys that were on this site. He knew that he was good looking, that woman of all ages found him attractive even though he was on the wrong side of forty. Unlike his ex he'd kept himself in shape after their marriage ended, he went to the gym several times a week and ran regularly. Once or twice he'd even overheard his daughter's friends whisper that she had a hot dad.

And he wouldn't hurt Cyana, not more than he had to. He'd make it good for her.

Fortunately he had plenty of money since the divorce had been more or less amicable when it came to finances and they both had hefty salaries. They'd agreed to split everything up pretty much evenly and he'd never needed to pay alimony, although of course he'd be putting in his share for the kid's college but he's set up a fund for that a long time ago.

So he had plenty of money to blow if he so chose... and he chose to blow it on this.

Two hours and an almost absurd amount of money later he was the proud owner of a teenager's virginity. He put all the pertinent information of when / where to meet this upcoming weekend into the form that the website provided.

******

The Windham hotel, room number 415.

Cyana almost licked her lips out of nervousness before she remembered that she was wearing lipstick. Was she really going to do this?

Yes.

And not because of the money, although that ridiculously hefty sum was a nice bonus. This was something she'd been planning for a long time, ever since she'd heard about the website that she'd auctioned off her virginity. Almost exactly one year ago she'd heard her older sister talking to one of her friends about it; her friend used it kind of like a dating service but she'd said that the best money went to the virgins.

The guys who used the site were rich. Older. Mature.

She'd always had a thing for older men, crushing on her teachers throughout high school, her coaches, just about anyone older. Even if they weren't hot or in great shape, she just found them so much more intriguing than the boys her age. Which was how she'd become the last virgin on the cheerleading squad. Boys her age just didn't interest her.

But giving her virginity to an older man? A stranger? For some reason that got her jets going hot and ready. Maybe reality wouldn't live up to the fantasy, but at least she'd be well paid for the loss of her hymen. None of her friends were still in a relationship with the guy that popped their cherry, and they hadn't gotten anything out of the exchange like she would be.

Taking a deep breath, she adjusted the neck of the skimpy white sundress she was wearing and put the hotel key into the slot.

The skirt of her dress swirled around her thighs as she walked through the door. The hotel room was nearly spotless, but across the room there was a man sitting in a chair looking out the window. Since none of the lights were on she couldn't see any of his features, just his outline against the brightness of the window as he stood and turned towards her. He was tall, had a healthy crop of hair and looked to be in fairly decent shape, but that was all she could see.

Excitement and anticipatory lust tingled in her body as she pasted a smile on her face and stepped forward, closing the door behind her. Was it just her imagination or could she actually feel his eyes caressing her young body, lingering over the low cut of the front of her halter dress and the hem around her tanned thighs?

"Hi," she said, unnerved by his silence and doing her best to cover it. "I'm Cyana, you must be Peter." She flicked on the light switch and gasped. "Oh my god... Mr. Samuels?!"

The familiar handsome face of Mary's dad was the last thing that she'd expected to see. A rather rugged face, framed by dark hair with a dash of grey at the temples and little silvery highlights scattered throughout the bit of scruff on his face. Mr. Samuels was a DILF - Dad I'd Like to Fuck. That was the running joke among his daughter's friends. Sure she'd drooled over him wearing a swimsuit in the summer. Sighed over him when he'd done something particularly nice or caring for the girls. Masturbated to a fantasy of him in her head multiple times.

But not once in any of those fantasies had she been so utterly humiliated as she was right now.

The fantasy of being with an older, rich, mature man suddenly seemed dirty and weak as she stared at this man that she knew... that she HAD known for years, and knew that HE knew she'd sold her virginity on the internet. She felt dirty. Ashamed. And impossibly young and stupid. If she was lucky he would only lecture her himself and not tell her parents what she'd done. And she'd have to return the money to him of course. God... how was she going to cover the percentage that the website took?

Her cheeks bloomed red before paling to white several times as he stood there watching her. Assessing her. Tears of humiliation sparked in her eyes.

"I can't imagine what you must think of me," she muttered, dropping her gaze to the floor, not wanting to see the disgust and condemnation on his face.

"I think... that right now you look more beautiful than ever," he said quietly in that oh so sexy deep voice of his. "And that I have been looking forward to this all week."

Shock suffused her and her head flew back up as she heard him began to walk towards her. The look in his dark eyes something she'd never seen before and she felt a stirring sensation deep in her belly as her body responded to it. As some primitive instinct in her brain said that the man before her wanted her... desired her...

"Are you... are we..." He couldn't possibly be suggesting...

"What's the matter, Cyana?" he asked, his deep voice rumbling in a way that made her insides tighten, the hairs on the back of her neck prickling. He stopped moving towards her, standing at the foot of the bed, and she found that she couldn't stop looking from him to the piece of furniture that she'd assumed she'd be losing her virginity on. That she might very well be losing her virginity on if her instincts were correct. "Having second thoughts about selling your virginity?"

Yes. Except that now she was wondering if he was just trying to scare her. Twisting her hands in front of her she tried to figure out his intentions, tried to think of something to say, but it felt as though she was hurtling through space at top speed and in a moment she was going to crash and there was nothing she could do to slow herself or stop it and there was no air to breath to scream much less talk. Even worse, she could feel herself becoming aroused at the idea of losing her v-card to Mr. Samuels. Heck... he was hot. Older. The difference between him and the boys her age was laughable.

"You know what I think?" His voice was like a caress across her skin and he was moving towards her again. Slowly. Deliberately. Her muscles tensed, screaming at her to run, but she couldn't move right now if her life depended on it. "I think you wanted to do something a little dangerous. To lose your virginity to a man who knows what he's doing, who can make you feel things..." He was standing right in front of her and he lifted his finger to her jawline and began to run it down her neck, down the center of her collar bone and down to her cleavage. It felt like her nipples had hardened to diamonds and she felt her lungs constrict as his finger began to trace the low-cut neckline of her sundress. Mr. Samuels' eyes never left hers. "A man who can make sure that you enjoy it."

When he suddenly cupped her breast in his warm palm, Cyana moaned and nearly collapsed in front of him. That felt so... good. He wasn't the first male to touch her breast, but he was definitely the first MAN. Having Mr. Samuels feel her up was an entirely different experience. The suddenness of his grip on her soft flesh, the heat in his eyes, his utter confidence as he touched her was nothing like the panting, greedy boys that she'd made out with in the backseats of their cars. They groaned with excitement just from a feel of her breasts, they groped without finesse, and she hadn't felt one tenth as excited as she did right now.

His eyes locked on hers, Mr. Samuels brought his other hand up so that he could gently squeeze both of her breasts and she panted as she felt the fabric of her dress rubbing against her nipples. The sundress didn't really allow for a bra so she hadn't worn one.

The expression on his face didn't change although she could swear that his eyes were looking hungrier and hungrier. Then, suddenly, his hands were gone and she was left standing trembling as he turned his back and walked away.

Sudden panic assailed her. What had she done wrong?

Mr. Samuel's turned and sat on the bed, facing her. "Take off your dress Cyana, I want to see what I paid for."

A flush heated her entire body, along with a healthy dose of anger. He was talking to her like she was a... her cheeks paled. Like she was a whore, like she had sold her body for money. Which is exactly what she had done. He waited patiently, watching her with that blank expression as she lifted shaking hands behind her back to undo the zipper. Her mouth felt incredibly dry and she realized that she was nervous. Because she wanted him to find her desirable. How strange that she suddenly felt so incredibly unsure of herself, but he'd put her off balance talking to her the way that he had.

So her hands trembled even more as she tugged down the straps of her dress and revealed her almost entirely naked body to her best friend's dad. The man who had paid for her virginity.

"The panties," he murmured, his eyes sweeping over her curves and she found herself wanting to curse at him. Wanting more of a reaction from him. And yet her nipples kept throbbing, her pussy was creaming her panties as if she actually liked being treated like this.

Almost defiantly Cyana pushed her panties off of her hips and let them drop along with her dress, revealing her neatly trimmed mound. It only had a small triangle of blonde pubic hair covering it and she'd completely shaved her pussy lips beneath them. Unable to meet Mr. Samuels' gaze in her naked and vulnerable state, Cyana lowered her eyes as gasped as she realized she was looking at a very sizable erection at the front of his pants.

Not embarrassed at all, Mr. Samuels' only laughed when he realized where she was looking.

"Don't worry sweetheart, I'll be gentle."

It should have been cliché. It should have sounded silly. Instead she just felt herself shiver with anticipation. With heat.

"Come here."

Closing her eyes for a moment, Cyana gathered her courage. When she opened them again Mr. Samuels was still sitting on the bed staring at her, a small and somehow intimidating smile decorating his lips. Her legs quivered as she took a step forward. Mr. Samuels' smile broadened and she felt her breath stutter. Feeling as though she was walking towards a cliff, readying herself for freefall, Cyana kept walking until she was standing right in front of Mr. Samuels. The sound of her heart beating filled her ears.

She gasped as he thrust his hand between her legs, his eyes on her face as he stroked his fingers between her plump, virginal pussy lips. Unable to bear the look of triumph on his face as he found her soaking wet, Cyana closed her eyes and shuddered as his fingers found the entrance to her body.

"Please..."

"Please what?" he asked, one long finger pushing inside of her and making her gasp.

She covered her face with her hands, unable to stop a low moan from falling from her lips. "Please... this is so embarrassing... can't you just do it?"

Mr. Samuels' laughed, the sound so dark and rich that it made her shiver as she peeked through her fingers at him. She didn't realize that her reluctance, her modesty, the very innocence of her request was turning him on even more. All she knew was that she had never expected her best friend's DAD to be the one waiting for her in this room, to put his hand between her thighs and penetrate her chaste body with his finger, preparing her for a much more intimate penetration.

"Oh sweetheart... I'm not just going to DO anything. That's what a boy with no control over his hormones does, and you wanted a man."

Although he realized that he was perilously close to losing his own control. After all, he wanted to make this good for her but right now his body was yearning to just lay her out on the bed, spread her creamy white thighs, and plunge into the sopping wet orifice that his finger was currently occupying.

There was really only one solution and it made him grin with anticipation. Pulling his finger out from between her sweet thighs with a sloppy wet noise, he put it in his mouth, watching the heat rise in her face as he sucked her juices from his finger.

Cyana had never seen something so simultaneously disgusting and erotic in her life. His finger had been shiny with her juices and yet he was slurping on the digit like it was coated in something delicious. Then he popped the finger out of his mouth and reached down to unbutton his pants.

She swallowed convulsively, realizing that she was going to be getting her first look at the penis that was going to take her virginity.

"Oh god..." She couldn't stop the exclamation as his erection thrust out of his pants, long and thick, impossibly hard with a purplish head that was already oozing pre-cum. And THAT was supposed to fit inside of her?! Maybe it was just because of the circumstances, but she felt sure that it must be larger than any other dick she'd seen before.

"On your knees Cyana."

Part of her screamed that she should protest, that this wasn't part of what he'd paid for, but with Mr. Samuels' dark gaze boring into her she found herself falling to a kneeling position in front of him. With her shaky legs it was surprisingly easy.

"I don't want to hurt you, I'm going to make this good for you," he said, threading his fingers in her hair and pulling her reluctant mouth towards the tip of his cock. "But I need you to take the edge off first, otherwise I'm liable to take you too fast and too hard."

The young beauty moaned at his words, allowing him to thrust of the head of his cock between her pretty pink lips. Cyana looked up at him with wide blue eyes, half anxious and half sexually excited, the mushroom of his cock already in her mouth. Instinctively she flicked her tongue against it, tasting the salty pre-cum, licking the velvety soft head as though it was a scoop of ice cream.

He tasted like salt and musk and male, and she only had a moment to adjust to what was happening before his hands were pulling her inexorably downwards, sliding more of his cock into her mouth. This was not her first time giving head, but it was definitely the first time that she'd felt out of control while doing it. Normally performing oral sex made her feel both feminine and powerful. Right now she felt feminine and exquisitely vulnerable in a way that she'd never experienced before.

Mr. Samuels had a firm hold on her head and was thrusting his hips upwards every time he forced her mouth down on him. She grasped the base of his cock to keep herself from gagging as he fucked her mouth. Because that's exactly what he was doing, fucking her mouth. It was rough, it was hard, it was humiliation piled on top of humiliation...

And it was making her hotter and wetter than a rainforest.

Her body was throbbing, aching, wishing that he would just touch her anywhere but her head. The space between her legs felt empty without that long finger inside of her, the tops of her thighs were becoming slick with her juices as she rubbed them together in an effort to relieve the needy compulsion. As her head bobbed her breasts bounced, hard nipples wanting to rub against something. She desperately wanted to touch herself but she couldn't even imagine how much more degraded that would be to her pride.

The spurt of creamy froth in her mouth took her off guard as he forced her head down so far that her lips met her fingers, his cock pulsing against the back of her throat. She whimpered and squirmed, trying to pull away as hot fluid poured into her mouth and she swallowed desperately. Something else she'd never done before, but it was swallow or choke. The head of his dick was too far back in her mouth for her to be able to spit it out, it was spraying the back of her throat and sliding right down into her belly.

When he finally released her head she came up sputtering, furious.

"That wasn't part of the agreement!" She glared at him. "I'm done here!"

He just laughed. "Not if you want the money you're not." He chuckled, putting one finger under her chin and tipping her head up to look directly into his eyes. The hot flame in his gaze made her shiver. "Besides, if you really didn't want to do this you wouldn't still be here on your knees in front of me. You like this. You could have walked out of this room at any time, I know you don't actually need the money, but you're still here on your knees with my cum in your belly and a sopping wet pussy that's just aching for its first cock. Isn't it?"

Red and white splotches covered her face as she flushed and paled, wanting to deny his words but knowing that all he would need to do is look at the evidence coating her thighs to know the truth. The taste of him was filling her mouth and even though it made her slightly nauseous it also turned her on.

Studying her expression, Mr. Samuels smiled. "You can leave if you want to, Cyana. No one's forcing you to stay. You can go back to your regular life, go out with some nice guy and eventually let him pop your cherry after a safe number of dates. Or you can get your sweet ass up on the bed and let me find out what a virgin's pussy tastes like before I fuck it."