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.
