First Day
Jon woke up to the sound of his phone buzzing off the nightstand. Through blurry eyes, he could just make out a string of messages from his girlfriend.
Well, former girlfriend. He and Claire had changed the settings on their relationship to friends-with-benefits about a year ago, when it became painfully obvious to them both that they were on different tracks. She came from money. She had real friends. She had a good job at one of the big banks that was supposedly taking her places. He, on the other hand, was a loner who wanted nothing more than to brood in sad diners, scribbling in sad notebooks, dreaming of the Pulitzer that would never come. But the sex had been good -- great, even -- and it just made no sense to throw the baby out with the bathwater. So whenever she was bored she would call, and he would go to her doorman building and fuck her loud and hard, much to the annoyance of her roommates.
Given all that, Jon was expecting to read yet another hookup request, but he was wrong.
hey
where've u been?
hellooo?
Terry's having a party at his place in wburg sat. u shld cum
lol i mean come
i miss you
He stared long at his phone, wondering if he wasn't reading a sweetness into her words that wasn't there. He hadn't heard a sentiment like that since the break-up. Everything since had been so transactional. Jon kept rereading the texts, overthinking his response, when an incoming call put an end to all that. It was from an unknown number, but something told him to answer it anyway.
"Good morning, sleepy head," the voice said. It took him a moment to realize who it was. "I'm sending a car to pick you up in, oh, about twenty minutes. Can you be ready by then?"
"Um, sure," Jon replied. He asked her how to dress and instantly regretted doing so.
Barbara laughed. "Nothing at all, as far as I'm concerned. No. Just do you. You're going to the warehouse and there's no one to impress there."
Jon put down the phone and took a few moments to reflect on his so-called interview with Sean and Barb, replaying every thrust, every gyration. Without thinking, he reached down beneath the sheets to play with himself. He rubbed his cock in a daze until it was almost convinced he meant business, but something told him to keep his powder dry. He had a big day ahead of him and, given his employer, there was no telling what he would be asked to do.
The limousine pulled up to his run-down brownstone just as he hit the curb. A short, well-dressed slob stepped out of the driver's seat and nodded at Jon. It took forever for the driver to walk around the limousine and open a passenger door in the back. The first thing Jon saw were the unmistakably long legs of his boss. A fiendishly happy Barb leaned forward to reveal herself, as if he had just found her in a game of hide-and-seek.
"Hiiii," she sang as she patted the seat next to her. There was another woman in the car across from her on the rear-facing seat. Like Barb, she was dressed in what, to Jon, looked like very expensive business attire. She only briefly glanced up from typing messages on her phone as he slid past her to take his appointed place.
"This is Vera," Barb said. "She does all the work I'm supposed to do."
"Can't argue with that," Vera said. She had a British accent. Vera reminded Jon of a Rockette: she was tall and fair, with shiny black hair pulled tightly back into a bun. She was beautiful in a way that made it hard to distinguish her from other women of her type. He smiled at her but she was already back to her phone.
Jon watched his brownstone disappear from view as the limousine pulled away from his old life. "I thought you were just sending a car for me," he said.
"I did!" Barb protested. "I didn't tell you I wouldn't be in it." She crossed her legs in his direction. "I wanted to make sure your first day got off to a good start."
Vera looked up from her phone and shot Barb a miserable look. "You've fucked him already, haven't you."
"Why, whatever makes you say that?" Barb laughed as she leaned into Jon. She placed a hand on his crotch, rubbing it with her entire palm. Though he was taken aback, Jon could feel his cock already responding to her caress. He blushed every shade of red his body could muster.
Vera shook her head, unimpressed. "You're such a fucking slut, Barbara." Jon was struck by how she could talk to her boss. It was a good sign, he thought. "So what shall it be for him, then? Admin? Facilities? Third Floor?" That last option she pronounced in a suspiciously different tone.
"He's from Tom's group, so we'll start him with what he knows and work from there."
"Fine," Vera sighed. She took a stack of papers out of a leather bag at her feet and made a few notes on them in pen before handing them to him. "Here. Sign these."
"What is this?" he asked.
"It's a contract," Vera replied. "You're signing your life away, didn't you know?" He was sure she meant it as a joke, but it was hard to tell.
"It's all just boring stuff, really. You know, to make sure you get your new salary, benefits," Barb explained, "There's a non-disclosure agreement in there, too. You'll have a lot of secrets to keep from now on, but you knew that, right?" She was still massaging his crotch.
Jon pretended to read what he was signing, but it was no use. All the legalese just blurred together, and Barb's playfulness was too big a distraction. The cabin was quite roomy for a limousine, but it was still getting awfully hot in the confined space.
"Mmm. It's gotten so hard," his boss noted. "I can see its head through his pants! Ver, can you see that?" Vera just rolled her eyes. Barbara leaned in close, tickling his ear with the tip of her nose. "Why don't we give it some fresh air," she whispered.
"What? Now? Are you crazy?"
Barbara bit her lower lip and grinned.
"Uh, but I need to sign this contract!"
"You can still do that," Barb argued, "I won't get in your way." She started undoing his belt.
"Um, ok, this is happening," Jon reported. He lifted his pelvis to help her get his pants down. Out popped his throbbing staff, much to Barb's delight. She wrapped her fingers around it and started stroking. Jon shot a nervous look at Vera but she was answering texts again.
"Isn't it pretty?" Barb enthused.
Vera glanced up from her phone. "It's not exactly the biggest penis, is it," she replied.
"No, but it's just so nice. It's like, the picture of a penis. Like, the dictionary would have a picture of this penis in it." She kept stroking. "Mmm. I'd love to suck it off right now, Ver. Wouldn't you? Clarence wouldn't mind if we walked into our meeting covered in cum, would he?"
"I highly doubt it," Vera said.
Just then, Barbara's phone started vibrating. "Speak of the devil," she said. "Hi, Clarence. How are you? Yes, I got the PDF..." Barbara leaned away towards the car window to focus on her conversation, but her other hand was still working Jon's cock.
His breath was getting heavy. His pelvis started to rock, thrusting his shaft against the rhythm of her strokes. Jon had never felt so awkward as he did at this moment, what with Vera sitting right across from him. Not that she seemed the least bit bothered. He closed his eyes and dropped his head back, trying to escape the weirdness of the situation, while at the same time thoroughly enjoying the feeling down below.
"Are you done signing those papers?" Vera asked.
Jon looked at the unfortunate crumple of documents he was clutching in his left hand. He smiled sheepishly as he handed them over. She flattened them out, then put them back in her bag.
"Well, anything you missed, we can go over later," she said. She proceeded to stare out the car window, only occasionally stealing glances at his crotch and what Barbara was doing to it.
He did not want to cum. It just felt like the wrong time and place for it. But Barbara kept at it, all the while talking headcounts with her client, and Jon could feel the sensation welling up inside him. It was getting harder to control the tension in his body and he tried not to make a sound, but a faint "oh God" slipped out from under his breath.
Vera shot him a look. Perhaps she was annoyed that he couldn't keep it together while their boss was on a call, or maybe she was just curious to see the eruption that was surely coming. He couldn't tell. She glared at him and took a deep breath before gazing out the window again.
"We're there," she said.
"Clarence, I have to go. Yeah. I'll see you in a few." Barb put away her phone. "That man loves to hear himself talk, but don't they all." She looked down at the action between Jon's legs. "Hmmm. How's this pretty cock doing?"
"Just fine, by the looks of it," Vera remarked.
"My, it looks like it's about to explode! Are you really close?"