The Manager

Jessie's manager was not attractive. At least that's what Jessie thought, when she first saw him, though she didn't quite understand herself why that was her first thought — whether she'd fuck him or not. Not that she'd had sex before ... she just hadn't met the right person. Sex was something that was meaningful. You should do it with someone you loved.

The other waitresses thought he was sexy, though. Jessie couldn't figure it out. Ryan was his name. He had a big dark beard and he was about her age, which was 26 (well, maybe he was a little older — it was hard to tell these days, with the beard) and people reacted like you were a leper if you told them you were still a virgin at 26.

Not that she hadn't had offers. Jessie was gorgeous, everybody said; big pouty lips and big eyes and a thin fragile neck and big boobs for her frame. A tiny waist too, and legs up to here. Curvy and thin, which was something that everybody wanted.

But Jessie was too afraid. Her friends had shown her pictures of dicks, big thick dicks and animated gifs on Tumblr of dicks penetrating willing, tight pussies, tiny little pussies that Jessie couldn't imagine accepting these huge ... appendages. She had no brothers and no sisters, nobody to teach her about human anatomy.

She knew the mechanics, of course. She wasn't a complete moron.

So it was strange being around Ryan, with his beard and his tattoos, and his hands always wandering around her waist and grabbing her wrist at weird times. He knew she was a virgin. It was a big joke around their workplace. But until now she had never been curious about somebody.

And what a somebody! The other waitresses loved Ryan. He was tall and lean and one of the girls said he reminded her of a jackhammer, like he could pull her hair and fuck her senseless. It was his hands and the way he moved, they said.

And the gossip went that he'd already worked his way through some of them.

Jessie didn't want to know. What happened during those nights when she went home, and they all stayed after to drink themselves silly? The way he looked at her sometimes, like she was a rabbit and he was a wolf. Did he fuck them all? Did he fuck them all senseless? She could feel him closing in on her, cornering her sometimes.

Jessie was scheduled to work the closing shift one day, a shift she didn't normally work. She wasn't happy about it. She had agreed to a date that night, with a nice man from the lawyer's office down the street: a paralegal or something, she wasn't sure of the actual profession. He wasn't a lawyer, but he worked in the office and he had brought her flowers every day and told her she was pretty. Jessie had at first thought that he reminded her of a rodent, but the other girls thought that if he brought her flowers, then he was at least worth a date. And so she had agreed, but she had to cancel it because of her schedule — the schedule that Ryan devised.

Ryan couldn't believe that someone as hot as Jessie was a virgin. When they'd hired him, he'd met all the girls — one of the criteria for hiring the waitresses was that they all be hot — but Jessie was the hottest. The waitresses were all required to wear these tiny dresses that hit just above the inner curve of their thighs, so that whenever they bent over — and they bent over a lot — you could see the edge of their panties, the slick outline of their pussies. It was intentional, of course, and they knew it — hotter waitresses got better tips.

But Jessie — Jessie didn't know it. She knew that men liked her, but she didn't know that the reason why — other than her big, eager tits and her long curvy legs — was that she had never known a man. A girl who looked like that should know a real dick. And Ryan was the one to give it to her.

Ryan knew he had a big dick. All of the girls he'd fucked had told him. One girl told him that his dick was the exact circumference of her wrist, it was that big. And their cries when he penetrated them told him too. You couldn't fake that many girls. And his dick really, really wanted to be Jessie's first. So he scheduled her to close one day, with him.

It was good to be a manager.

*

On the day that Jessie was scheduled to close, Ryan could hardly wait to get the last customer out of the bar. He finished as much paperwork as he could while he watched Jessie wipe down the bar through the security cameras. He'd been half hard for half the night and he could barely restrain himself every time she bent over to pick something up or reach over to grab something. It was all he could do to not pull down her panties and bury himself into that sweet virgin pussy.

When it looked like she was almost done, he left the office and went downstairs to talk to her.

"Want a shot of whiskey?" he said to her, pouring one for himself.

Jessie looked at him. She liked to drink as much as the next girl, but she'd already had a few with some of the customers and she thought that maybe it was too much. "I don't know ..."

"Come on, live a little," Ryan said, pouring one for her too. "Please?"

"Okay." Jessie came over and picked up her shot, looking at him.

"Come over here," Ryan said, and Jessie came around behind the bar so that she was next to him. His hand snaked around her waist and he pulled her closer. "Salud," he said, and they tapped their shot glasses onto the surface of the bar and downed them quickly.

"Whoo!" Jessie said. "That might have been one too much."

"Come on, one more," Ryan said, busily pouring them another. "It's been a long-ass day."

"All right," Jessie said, not moving away. The thing was, even though she wasn't attracted to him, not in a long-term way, there was something about his hand on her waist that made her want to stay, something about the way his hand was creeping down towards her ass, the way his hand seemed to own her.

They did another shot, and then another. Jessie was having a hard time figuring out where her cell phone was.

"Hey," Ryan said, "I heard you're a virgin."

"So what if I am?" Jessie said, grinning at him. She'd heard this before.

"So ... why is that?"

"I don't know. I just never met the right man."

Ryan poured them another shot. "What constitutes the right man?"

"I don't know ... someone tall and strong and sensitive I guess."

"There's no such thing," Ryan said, unbuttoning one of her buttons.

"Um, of course there is," Jessie said. She didn't really want him to unbutton her dress, but she kind of liked it at the same time.

"No, there really isn't," Ryan said, unbuttoning two more. "Being sensitive is just another lie people tell themselves. Sensitive is a stupid quality."

"No it isn't," Jessie said, feeling her own sensitive nipples harden as he brushed his hands over them, unbuttoning another two so that her lacy white bra was showing.

"Well," Ryan said, unbuttoning the last button and letting her waitress uniform fall open at her waist, "sensitive is definitely overrated. It's been my experience — and excuse me — that women just sort of want to be fucked."

Jessie felt a sort of pressure in her pussy as he pulled her closer, his big hands taking ownership of her slender waist, sliding down towards her ass and gripping it.

"Wait," she said, "I don't ..."

"You don't want to what?" Ryan said, his lips already on her neck, warm and hot and sucking.

"I don't want ..."

"It seems to me that you want plenty." He pulled her even closer, and Jessie could feel the hardness in his pants. Not knowing what was in there — not knowing what to do — she stayed, hoping that he would let her go and that the pressure in her pussy would go away.

This seemed like the wrong move because he pulled her skirt up and started pulling down her panties.

"Wait — no —"

"Shhh," he said, nibbling her earlobe and sending her eyes upward, "It's going to be good."

When she didn't lift her legs so he could pull her panties off, he tore them off. Jessie could hear the tear of the delicate fabric.

Then his fingers were rubbing her, rubbing her where she'd never been rubbed; he sucked his own fingers and rubbed her some more, and she'd never experienced anything like this before, it was like explosions and ice cream and her eyes were rolling back into her head and she was making noises.

*

Ryan couldn't believe it. Give a girl some whiskey and rub her ass and rub her clit and she was yours. He felt her tight pussy with his fingers, felt her eager wetness, felt her tits against his chest — he couldn't help it, he pulled the sleeves off her arms and undid her bra as fast as he could, grabbing those full, perky breasts in his hands and trying to grab her ass at the same time, trying to penetrate her pussy with his fingers, her wet, wet pussy. God, she was a virgin — she was all his. He could feel the tightness, feel the barrier.

Holding her tight to him, ignoring her slight protests, he undid his pants. His dick sprang free, ready to enter her. That's when he picked her up and put her on the counter, her legs already open and waiting, her body betraying her. She was open and ready — he could feel her wetness.

He felt her again, made sure of her wet, hot opening. It was going to be tight, but he didn't care — he had to fuck her now. He guided his cock to her soft, warm entrance, and when he found it — hearing her gasp one last "No!" — he thrust with all his might into her tight pussy.

They stood together for a second, locked, Jessie not believing that her first cock was penetrating her to the hilt, Ryan not believing how tight she was, how wet, how unbelievably hot it was to know that he was the first, the one that she'd always remember when people asked her what it was like the first time. He started to fuck her, hard, not caring if it felt good for her, feeling her cunt muscles grab his dick and pull him in, fucking her so hard that their bodies slammed together, holding her in place with his big hands. Her tiny body couldn't do anything about it while he used it. Her cries were music, spurring him on. Penetrating her and penetrating her and penetrating her, feeling her pussy give way to his manhood, his hard rhythm. This was what women were for.

Jessie took it, all of it, feeling him enter her again and again, feeling his big dick take control of her, her legs lifting of their own accord and wrapping themselves around him, her voice calling higher and higher. She began to shake in his arms as he fucked her.

Ryan heard her cries and quickened his pace, no stopping now, her high, loud gasps in his ears. Her thighs were wrapped around him, her tits and her heels bouncing as he thrust. He caught a glimpse of the two of them in the mirror, and seeing her being fucked by him triggered it. All at once, he felt his balls tighten and he came, emptying himself into her, slowing down for a few last strong thrusts before finishing, firmly inside her.

They stood for a few moments, breathing hard.

Then Ryan withdrew, buttoned up his pants, told her, "Clean this up," and walked back up to the office.