The Upper Hand

At several points in his story he refrained from being as graphic as he might have been with a male friend because of the look of shock and surprise on Lilly's face. He glossed over the more advanced lessons, summing them up by saying, "She really was a kinky old broad."

Lilly ignored the kinky comment and focused instead on the age reference of his "Mrs. Robinson" story. "How old was she?"

"That's the funny thing. She was probably your age," Jack said. He saw Lilly's wide-eyed look of surprise and quickly realized he had accidentally called her old. That wasn't what he meant. He pretended to think for a moment before adding, "Yeah, I'd guess she was around 27 or 28, at the time, just like you."

Several years had passed since Lilly had been 27 or 28. His mistake felt good, but not as good as what he said next.

"You're prettier." He said it with a dismissive shrug, as if it didn't mean anything to him, just a statement of fact. Before Lilly had a chance to bask in the glow of another unexpected compliment from her corporate rival, he pounced. "Okay, your turn," he grinned. "Seeing as we are BFF's and all."

Horrified, Lilly looked at her hands and fidgeted. She never expected him to share such an intimate story and now she felt trapped. She took a deep calming breath. "It was in the back of a car," she waved her hands around. "I've hated car sex ever since," she didn't really want to go into details and let her voice trail off.

"I bet I could change your mind about that" Jack thought to himself but outwardly stayed silent so she would have no choice but to continue.

"It was just so awkward and messy, like most girls first times I guess," she said quietly hating that she felt she had to disclose an episode on her life she would rather forget. "But like all things it gets better with practice and experience." She finally said straightening up and putting her tough, one of the boy's attitude back in place.

Jack had picked up on how Lilly fidgeted and waved her hands around as she told the barest bones of her deflowering story. In the conference room at work, surrounded by a nearly all male staff, Lilly was unflappable. She was the same way with lecherous male clients who spent more time staring at her tits than her face. Seeing her uncomfortable and squirming was fun. He pressed his advantage. Was there more to this ice queen than he had suspected? What would he find if he broke past her tough boys' club exterior? "You know, by comparison, your story was rather weak," he challenged.

"Fuck you," she grumbled, determined to keep up her defenses but her defenses cracked a little bit when Jack laughed. "What?" she demanded.

"Now you sound like me," he grinned. Another smile? She marveled, she liked seeing those on his face, it made him seem less of a rival and more of a friendly colleague as he had once been.

"Deal with it," she said. Disgusted with the lack of scenery and the long drive ahead she fished inside her purse for her phone. Sure, it was late, but maybe Olivia had replied to her email. She stared at the phone for a long moment before realizing they didn't have service, she tossed her phone back inside her purse.

"I don't think so," Jack said after her little show. "Quid pro quo, you know? I told you a good story and you wimped out. If we're going to make Gregory happy and become BFFs, I think I deserve something better."

"When did you start caring about Gregory?"

"I don't," Jack snorted. "But you still owe me."

"What else do you want to know? I gave my cherry to a bad boy who I thought loved me. We did it in the backseat of his car. It hurt like hell and he lasted less than a minute, okay?" Jack's prying was getting under skin. It was late, she was hungry and the scenery sucked even more in the dark.

"What's the kinkiest thing you've ever done?" Jack blurted out with his eyes on her instead of the road. He saw her flinch and started laughing. This was fun!

Lilly flipped him off for a second time. Who did he think he was asking her a question like that? What was worse was how he kept staring at her. Sure, the road was straight and flat, but shouldn't he at least glance at it from time to time? "Care to mind the road?" she grumbled.

"Not really," he said without turning his head forward again.

"Fine. I once peed on the side of the road in broad daylight, okay?" Lilly shot back, determined to satisfy his curiosity without revealing anything. It was none of his business what she liked to do in the bedroom.

"Amber-Marie liked it when I spanked her," he replied, finally turning his attention back to the road.

Lilly gasped before catching herself. Dammit! she instantly thought, regretting giving away anything to Jack. She tried playing off the sharp intake of breath as a yawn while her heart raced. She needed to climb in front of this game of his. She tried a technique she had never tried using before on Jack. If he wanted to be over-the-top with her, she could play that game, too. After finishing her fake yawn, she said with a sultry twist to her voice, "Now you're just trying to make me wet." She patted him on the knee as she said it and bit back a giggle when Jack nearly jumped at her invasion of his personal space.

Jack quickly regained his composure, surprised she would touch his leg so intimately. It was just a pat, a dismissive pat at that, like the kind one might offer a friendly dog begging for attention. Was that how she saw him, as just another man trying to get into her panties? "It's not quite that long," he quipped, hoping to turn the tables back on her. Her self-satisfied smirk told him he was still playing catch-up. On the horizon were the lights of a truck stop promising fuel and an all-night diner. Without asking, Jack switched lanes and put on his turn signal.

Lilly slipped on her heels eagerly anticipating the opportunity to stretch her legs and eat. While Jack refueled, she walked into the diner and felt the eyes of the few long haul truck drivers as they worked over her body. Lilly hesitated and considered going back to the car and waiting for Jack to finish filling the tank. Unwilling to back down, she caught the eye of the waitress and mouthed the single word, "Bathroom."

"Around the corner, honey," the gum chewing older woman said.

Returning to the diner, Lilly found Jack standing in the foyer waiting for her. She was glad to see him. "Hungry?" he asked. She nodded, feeling very out of her element. He led her to a booth and positioned her back to the staring eyes of the truck drivers before sliding across from her. Jack ordered for both of them and never left the booth until they were done eating. He kept the conversation light and distracting, left a twenty dollar bill behind on the table for an eleven dollar check and escorted her back to the car. He opened her door, waited until she climbed inside and pressed the door lock down before closing the door. "Be right back," he said, locking her inside.

He jogged back to the diner. Lilly watched him move towards the bathroom with similar urgency. Had Jack been resisting his urge to go through-out dinner? That was the only explanation and Lilly was both impressed and touched that he would look out for her in a place like this.

"Think you can manage a couple more hours before we stop for the night?" he asked as he pulled the car back on the freeway.

"I can if you can," she said with a genuine smile as she marveled at Jack's natural sense of chivalry. Once he had dropped the gruff work persona, he was quite charming. They rode in silence for a few miles before Lilly remember her responsibility to keep him company. "Did you really spank Amber-Marie?" she asked. It wasn't a great opening line but his smirk said she had his attention.

"I did," he said, shooting her a sideways glance. "Not at first, but she taught me how to do it. She said women loved it."

"What do you think?" curiosity laced the question as she asked it.

His smirk turned into a big grin. "I think nearly every woman enjoys being treated like a naughty little slut from time to time."

"You would," she rolled her eyes in the dark of the car but her good humor remained in her voice. She realized she had lost her edge from earlier and decided to pull out the moves that had put him on the back foot before they had stopped. Lilly reached across to lightly stroke the suit coat that hung over the back of his seat, her fingers lightly grazing his neck as they moved past it, "I don't often get to see you without your suit coat. Do you always wear Armani?" she asked trying to get the image of him spanking her for some perceived misdemeanor from her mind.

Feeling a shiver run down his spine at the tickling feel of her fingers he decided to give as good as he got. His hand moved from the stick shift to caress the skirt that half covered her thigh enjoying the contrast between fabric and skin as much as the gasp his touch elicited.

"Probably about as often as you wear Chanel and Prada," noting that she hadn't flinch from his touch or tensed up, he left his hand where it was as the car continued on in cruise control. He noted that Lilly looked down at his hand but didn't remove it from her leg. Interesting he thought and the arrogant smirk reappeared on his face.

"Well a girl has got to compete with Armani and Hugo Boss," she laughed being on safe ground in this topic at least. His hand felt huge on her thigh and covered most of the exposed skin of her thigh above the knee.

"I would bet even your underwear is designer label, probably left a lot of money on the road back there," he grinned and he felt the muscles in her thigh moved as she curled her toes. He squeezed her thigh embolden by the fact that she had not asked him to move it and quipped, "I would go further and say it was part of a matching set and when you get home you will throw the bra away too."

Refusing to be the first one to cry "Uncle," Lilly turned slightly in her seat and ran a finger around the collar of his silk shirt. "You're one to talk, is this pure silk? And don't bother telling me you don't know or that it came with the suit because I won't believe you." Turning her body further towards him, had made her skirt rise higher on her thigh. Jack's hand followed her skirt's hem and in a caressing movement also rose higher up her thigh. Lilly gasped.

"Something wrong?" Jack asked belatedly stifling the small laugh that crept into his voice.

Lilly had considered ending their little game of chicken until she caught that laughter in his voice. Upping the stakes, she ignored his hand and stroked her own from the collar of shirt down over his chest, finding herself surprised at how muscular his chest felt. While many women spoke about being attracted to men based on their eyes or ass, broad shoulders and a well-defined chest was what did it for her. She let her hand linger over the silk shirt covering his chest as she spoke. "Nothing feels as good as pure silk, does it?" she suggested, purposely using a soft husky voice. Though she admitted it wasn't much of a stretch at this point.

"You have a very bad habit of avoiding my questions," he gave her thigh a quick smack before curling his fingers around the soft flesh of her inner thigh and giving her leg a squeeze.

"I do not," she feigned innocence while letting her hand trail down his body, satisfied with the fact that his breathing had begun to increase. Her eyes glanced quickly at his groin and she smirked. After seeing his large bulge she knew she was winning this little war, despite how aroused she herself felt.

He smacked her thigh again, "Liar," he growled. "Be careful," Jack said his voice ominously low, "If you act like a naughty little slut I will treat you like one."

"You wouldn't dare," she challenged caught up in the scene they were creating and aroused enough to wish he would.

Jack braked hard and pulled off to the side of the lonely highway.

Lilly snapped back to reality stunned with the speed at which the little game she had been playing went pear shaped and knew if she backed down now she risked being called a tease or ice queen forever. She froze in her indecision.

There was no indecision in Jack, she had pushed him far enough, it was time to put up or shut up. He undid her seat belt, pulled her awkwardly across the center console and across his lap. Opening his door widely to accommodate her head and shoulders he lifted the skirt and spanked her bottom hard. Surprised that his hand spanked flesh he looked appreciatively at the lace thong before spanking her again eliciting a tirade of curse words from the sexy woman.

"Stop!" she screamed flailing her legs around as his free arm tried to hold them in place.

"I'll stop when you admit you like it. All that fucking teasing, touching my neck and shirt, you're a slut at heart and need someone to take charge and treat you like the naughty slut you are." He punctuated his words with more spanks to her increasingly rosier cheeks.

Her mind rebelled, What the fuck did he know? but the fact was, it was true. She hated the way he seemed to be able to read her mind. She had been aroused since his story about Amber-Marie, his sweetness at the restaurant and his large hands on her thigh had only increased her need, no matter how much she had treated their bantering like a game, she realized she wanted this, wanted Jack. Finally, with tears making her perfect make-up run she cried out, telling him what he wanted to hear.

"Okay I admit it, I like it. I wanted you to spank me," she hung her head feeling her precarious position as her muscles relaxed and he gently caressed her sore ass. As she fully relaxed over his lap she could feel his hard on pressing into her belly which only served to arouse her even more. If he was hard, could she be winning by losing? Her head extended well past the car door. She clung to the armrest while staring at the road. Any traffic had dissipated along with the heat of the day but she knew someone might drive by at any time. Would a passing car slow enough to notice her half hanging from the car with her bare ass exposed and reddened?

Jack could smell her arousal. He never would have guessed such a submissive slut hid behind the confident professional woman he competed against at work. His cock was hard and throbbing as he looked down on the beautiful woman in such a vulnerable position. Opening the door had triggered the dome light and both map reading lights, filling the car with bright light. He caressed the bright, rosy pink of her bare ass before his hand slid between her thighs his fingers rubbing over the lacy thong feeling just how wet she was. Her heated whimpers rose up to his ears and he continued to tease at the folds pulling her thong up to add further sensation. He pushed her panties to the side as his fingers entered her and he felt her moist heat.

"Once again you haven't answered me properly," his free hand smacked her ass again making her squeal and buck. "You're a naughty slut aren't you?"

"Yes, damn it!"

"You need a man who can treat you the way you deserve to be treated, don't you?" He pressed as his fingers moved in and out of her tight wet cunt.

"Yes," Lilly whimpered feeling humiliated at being made to admit her private desires to Jack. She felt herself bend to his will, "I need a man who can take control!" She admitted the deepest part of her desires.

Jack was surprised by the admission but beyond pleased. His fingers continued to work on her as the thin material of her thong stretched and rubbed at her swollen clit. He felt her thighs tremble moments before she cried out and arched up, her muscles stiffening in the moment before she came over his hand. He withdrew his hand and wiped it over the back of her skirt, the dress would be ruined now, he smirked at the tirade that would probably ensue later and give him another excuse to punish her.

As a final humiliation, he gripped the waistband of her panties, tugged and pulled them down her thighs and over her calves until they came free of her feet. Lilly bucked and kicked her legs trying to stop him but couldn't defeat his leverage. He tossed her panties on the floorboard near her heels before lifting her from his lap. Lilly was mostly dead weight as she moved her back to her seat like a rag doll. "I need those," she whimpered with a glance at her panties. "I'll stain my dress."

"Good," he said, swinging the door shut, putting the car in drive and speeding away before she had a chance to work her seatbelt.

They rode in silence for several miles as Lilly tried working through what had happened. Jack was hard. She could see the magnificent lump inside his design pants and wondered if he wore boxers or went commando. She pulled her eyes away from temptation and stared at the dark beyond the headlights as the heat of her spanking slowly eased. She remained wet and in need. She squirmed, knowing Jack would notice. Jack's bright, intelligent eyes noticed everything. Lilly pondered breaking the silence, but how? What would she say? She stole another glance at his cock.

Wordlessly, Jack pulled her tiny hand and positioned it over his hard-on. Instinctively, she rubbed the long bulge and tried wrapping her fingers around it through his pants. She was glad he was hard, glad she wasn't the only one in need. She worked the flap covering his zipper. "Stop," he commanded. "You have to earn that, slut."

She went back to rubbing and caressing him. Give it time, she thought.Sooner or later, you'll want more. More miles passed beneath them as she explored and worked him over. She felt his large balls and experimented with different ways of caressing his shaft. She felt his hard cock throbbing while his face remained passive. He stared at the road and nothing more. At one point, he took a sip of his coffee from a cup in the console. His nonchalant sipping of coffee was maddening. Did he care she was sitting without panties while wearing a dress? Did her hand not matter to him? She squirmed again, knowing her weeping, needful pussy would be creating a wet spot on her dress. She could smell her arousal and knew he could, too. She lost track of how many more miles passed as she suffered. Her mind filled with images of his cock created by her own need.

"What's the kinkiest thing a nasty little slut like you has ever done?" Jack asked, finally breaking their silence as the horizon brightened with the distant glow of another town or truck stop. Lilly hadn't noticed a sign, but had learned enough of the desert to know it would take a long time before they reached that glow.

"I-I don't know," she hedged as she sorted through a mental highlight reel of times when she had thrown caution to the wind.

"Take your hand off my cock," he growled. Lilly felt rebuked as she slowly pulled her hand back to her lap but Jack wasn't done with her. He grabbed the front of her dress. His big fingers found the solid point of a hard nipple. His pinching finger and thumb startled her with his unerring accuracy and the firmness of his pinching. Lilly wasn't a masochist, but she did like it rough. That was something Olivia never understood whenever her sister set her up with another weak man more interested in gentle, soft play than understanding how sometimes a woman wants to be taken and lose all control. Sometimes, a woman wanted to be ravished by a real man who knew she wouldn't break. Lilly spent her days brushing off the advances of little men. If a man wanted her attention, he would have to command it. Somehow, Jack understood that. Or at least he did now.

She gasped as she felt another flood of passionate need tingling between her legs. But somewhere in the back of her mind, the professional version of Lilly Anderson refused to remain silent. As good as Jack's finger and thumb felt pinching and twisting her nipple, he was still Jack Cooper, co-worker and chief rival for the coveted corner office. "Fuck you," she hissed between clenched teeth.