Spanking Sydney

by Paige Tyler

  Or she could have if Erika hadn’t brought up the subject of Max Daniels the minute they got to the bar and grill where the other girl was meeting her boyfriend for dinner.

  “Every woman in the building is completely jealous of you, you know,” Erika said as she sipped her drink.

  Sydney’s brow furrowed. “Why?”

  Her friend grinned. “Isn’t it obvious? Because you work for the hottest guy most of us have ever seen, of course.”

  Sydney toyed with her straw as she stirred her drink. Now that Erika had brought it up, there had been a steady stream of women going in and out of Max’s office. They’d ostensibly come by to welcome him to the company, or drop off some paperwork, but the real reasons behind their visits were obvious. They’d been trying to come onto him. Though Max had been polite to the women, Sydney was secretly pleased he hadn’t shown any interest in them.

  “So,” Erika was saying. “What’s it like working for him?”

  Sydney shrugged. “He’s more demanding than Ted was, that’s for sure.”

  The other girl smiled. “Yeah, I kind of figured that since you’ve been getting to work before I do now.”

  Sydney blushed as she thought of the spanking she’d get for coming in late. For one crazy moment, she had this incredible urge to tell her friend about the spanking her boss had given her, and only caught herself just in time. Not because Erika was a prude, but because she was afraid her friend would go running to the HR department to report her boss for sexual harassment. Sydney definitely didn’t want that. She didn’t see what he’d done as sexual harassment. The spanking had simply been an effective way for Max to deal with her poor performance. While she was fine with it, she knew Erika wouldn’t be.

  A few minutes later, Erika’s boyfriend came in, and though they asked Sydney to join them, she declined, sure the two lovebirds would rather be alone. On the way home, she decided to stop by the video store to pick up a movie, but ended up being too distracted to watch it. For some reason, her thoughts kept straying to Max and the spanking he’d given her.

  What exactly was it about the spanking that turned her on so much? Was it the physical act of getting spanked, or the fact that an incredibly gorgeous guy had been the one administering that spanking? Then again, did it really matter what the reason was? The bottom line was that she’d liked it.

  Wow. That was quite an admission. It was one thing to say it hadn’t bothered her, but now here she was saying she’d actually enjoyed it. That begged the next question. Did she want it to happen again?

  Sydney chewed on her lip as she thought about that. Just because she’d liked the first one didn’t mean she’d like the next one. She supposed the only true way to know for sure would be to get Max to spank her again. But how could she do that? It wasn’t as if she could simply walk into his office, tell him she had an unresolved issue and ask him to spank her so she could figure it out. She was bold, but not that bold. No, but she could do the exact same thing that had gotten her spanked in the first place.

  And if her little plan backfired and Max decided to have her transferred to another department this time? She dismissed the thought with a shake of her head. Max was obviously the type of man who thought a good spanking was just the thing to straighten out a misbehaving secretary, so why wouldn’t he do it again? Especially if she dropped the proper hints at the required time.

  Sydney came up with her plan while she was lying in bed later that evening. Which, not surprisingly, got her extremely turned on. Before she even realized it, she found herself tumbling into an erotic spanking fantasy about her hunky boss.

  As usual, she came into late work again and Max was less than pleased. She’d act as if she hadn’t done anything wrong, all the while ignoring the scowl on his face. Then, to make up for being tardy, she’d bring him a fresh cup of coffee, only to “accidentally” knock over the mug, spilling the hot brew all over his desk calendar.

  Sydney leaned back against the pillows, smiling to herself as she imagined the scene unfolding.

  Max would be absolutely furious with her, while she would be oh-so-apologetic, even offering to get some paper towels to clean up the mess. But her boss would have none of it. Instead, he’d take her by the arm and bend her over the desk, telling her she was going to get a very hard spanking for being so clumsy.

  Naturally, she’d protest. But Max would ignore it, holding her firmly in place with a strong hand while he gave her a hard smack on the ass. That smack would be followed by another, and another, and another, until she was squirming so much that her already extremely short skirt would ride up even higher, revealing the barest glimpse of the stockings and garters she was wearing underneath. Okay, so it wasn’t exactly traditional business attire, but this was a fantasy.

  One that had her pussy dripping with excitement. Wetting her fingertips, Sydney slid her hand down the front of her panties and found her throbbing clit. Letting out a little sigh of pleasure, she made slow circles round and round the sensitive nub.

  In her fantasy, Max pushed her skirt up over her hips to reveal the skimpy black panties and garter belt. Would he be surprised to find her wearing such sexy lingerie? Maybe. But he’d only grunt in satisfaction as she caressed her panty-covered bottom. The image was so vivid, she could almost feel his strong hand squeezing her ass.

  The fingers on her clit quickened of their own accord, and Sydney forced herself to slow down. She had a whole lot of spanking to fantasize about yet. There was no need to rush.

  In her mind, Max was spanking her again, his hand coming down hard on the seat of her panties. Would a spanking over her panties feel much different than it had over her skirt? She didn’t think a pair of panties would offer much protection. Or at least they didn’t in her fantasy. In her mind, her bottom stung quite nicely.

  She closed her eyes and pictured Max moving back and forth, alternating from one cheek to the other, his hand connecting with the tender area of her sit-spots. Abruptly, Max stopped spanking her, but only long enough for him to pull down her panties so that he could spank her on the bare ass.

  Picturing her handsome boss spanking her bare bottom was enough to make her tremble, and she slid her hand down to thrust a finger deep inside her wetness as she imagined him smacking her ass over and over again.

  Her fantasy didn’t end there, but instead continued until Max went from spanking her ass to caressing it. He rubbed her stinging skin gently at first, then with a little more force, squeezing her freshly spanked cheeks until she gasped. Then he slid his hand between her legs to thrust his finger into her sopping wet pussy.

  Sydney slid a second finger inside, thrusting deeper as she imagined Max doing the same. All at once, the scene in her mind changed. Clearing the desk with a swipe of his arm, Max spun her around and pushed her back onto the desk, his hands going to his belt.

  Breath quickening, Sydney used her free hand to touch her clit, her fingers circling wildly around the plump nub as she imagined Max thrusting his hard cock deep into her pussy.

  When it came, her orgasm was so intense it took her a little by surprise, and after it was over, she lie back on the bed, breathing hard and staring up at the ceiling. Damn. If she could come that hard just from fantasizing about making love with her boss, she couldn’t imagine what the real thing would be like.

  * * *

  Sydney got to work early on Monday morning simply so she could make sure she walked into the office ten minutes late.

  It was all part of her plan to get Max to spank her again. She didn’t want to do anything to make her boss rethink his decision to keep her as his assistant—just enough to earn herself another spanking. And showing up late for work was a good start.

  Her tardiness didn’t go unnoticed. Max was pouring himself a cup of coffee when she walked into the office, and he looked up with a frown.

  “You’re late,” he pointed out as he set down the coffee pot.

  “Am I?” She gave him her sweetest smile. “I didn’t noti
ce.”

  He lifted a brow at that. “Come into my office.”

  She quickly shoved her purse into the drawer, her pulse fluttering. He was going to spank her during work hours?

  “And bring your notebook,” he added as he started for the door. “I need you to take down a letter.”

  She stared at his retreating back, flustered and a little frustrated. Dammit. She’d been so sure her plan would work. Then again, she reminded herself as she took a seat in one of the chairs in front of Max’s desk, her boss hadn’t spanked her for just that one infraction the first time, so it would take a few things to get him to give her one this time. The anticipation was half the fun.

  She didn’t want to make what she was doing seem obvious, so she was on her best behavior for the rest of the day, making sure all her work was perfect. She even came in on time the next morning, though she made sure she got back from lunch a few minutes late. That earned her another frown from her boss, but no spanking, so by midweek, she decided to up the ante.

  Her opportunity came that afternoon when Max asked her to type up several letters to various people. On each one, she inadvertently spelled his wrong, leaving off the “s” on Daniels.

  Putting the stack of letters on his desk for him to sign, Sydney gave him a smile, then went back to her desk. She figured it could be a while before he took her to task for misspelling his name, but he came out of his office almost immediately.

  “You misspelled my name on every one of these.” He held them out to her “Make the corrections and bring them back in for signature.”

  Sydney frowned as she watched him disappear into his office. That was it? Please make the corrections and bring them back into me for signature? Swearing under her breath, she turned back to her computer, banging on the keys as she made the corrections. What the heck was it going to take to get that man to spank her again?

  Determined to making him warm her bottom or get fired trying, Sydney not only showed up late for work the next day, but made several obvious typos on another stack of letters, including spelling Max’s last name wrong. When that got her called into his office that afternoon, she was sure he was finally going to spank her, but all he did was point out her mistakes. He was clearly pissed she’d spelled his name wrong again, but not enough to spank her.

  By the time Friday rolled around, she was ready to scream. Not only did she show up late for work again that morning, but she also came back from lunch late, too. Both earned her a scowl from Max, but that was it.

  She clenched her jaw as she pushed the intercom button. “It’s Jonathan Kriss from the Dallas office on line two.”

  “Tell him I’ll be with him in a minute,” Max said.

  She pushed the button for line one to let the big deal from Dallas know, but then hesitated. Max would be mad as hell if she “accidentally” disconnected Kriss instead of putting him on hold. The other exec probably wouldn’t be too happy, either. But a girl had to do what a girl had to do.

  A moment later, the intercom beeped. “Jon’s not on the line,” Max said. “Did he hang up?”

  “Shoot! I must have disconnected him by mistake. I’ll get him back on the phone for you.”

  She did, then “inadvertently” disconnected the man a second time.

  “Sydney, you did it again.”

  She had to fight to keep from smiling at the annoyance in Max’s voice. “I did? Sorry. I’ll try again.”

  She didn’t dare disconnect Kriss a third time. She didn’t want him thinking she was incompetent, too.

  Sydney waited impatiently for Max to finish up on the phone, figuring he’d come out to reprimand her as soon as he hung up, but he didn’t. That did it. She gave up. Beyond bummed, she turned off her computer and reached for her purse. No need to hang around late on a Friday afternoon if she wasn’t going to get a spanking out of it.

  Max appeared in the doorway connecting their two offices. “Sydney, could I please see you before you leave?”

  Something about the way he said the words made her pulse skip a beat. “Of course.”

  She put her purse back in the drawer and walked into his office. Her knees suddenly went weak as he closed the door behind her. This was what she’d wanted all week, so why was her heart practically pounding out of her chest?

  “You’ve been slipping, Sydney.” Max folded his arms and fixed her with a stern look. “Not only have you been late several times, but your work’s gotten sloppy again.”

  Sydney swallowed hard. “I know what you’re going to say.”

  He lifted a brow. “Really?”

  She nodded. She wiped her hands done the front of her skirt to stop them from trembling. “Yes. You’re going to say I need another spanking, and you’re absolutely right.”

  Sydney didn’t who was more shocked by the words, her or Max. He stood there, speechless.

  She couldn’t believe she was going to do this, but…

  Sydney walked over to the desk, flipped up her short skirt and bent over, revealing the skimpiest pair of black bikini panties she had in her wardrobe. Little more than a tiny triangle back and front, they barely covered her bottom, which was exactly why she’d worn them. And since she didn’t wear pantyhose in the summer months, he not only had a perfect view of her ass, but of her long, bare legs as well.

  Hands on the desk, she looked over her shoulder to see Max regarding her with what could only be called amazement in his dark eyes. So, her usually self-assured boss was put off-balance, was he? Good. Giving him a saucy look, she let her lips curve into a smile.

  “I’m ready, Mr. Daniels.”

  Without waiting for a reply, Sydney turned around and arched her back to lift her bottom a little higher in the air, then held her breath and waited. A few seconds went by. Then a few more. She slanted him a covert look over her shoulder to see Max standing beside her. She jumped when she felt him place his hand on the small of her back.

  “Since you seem to agree you need a spanking, why don’t you tell me what you’ve done over this past week to earn one.”

  His voice was soft and sexy, and deliciously authoritative. Sydney kept her eyes trained on the expensive wood desk. She hadn’t expected this. Now who was the one off-balance? “It’s like you said. My work’s been slipping.”

  “I’d like specifics, Sydney.”

  She wet her lips. There was something so exciting about listing her misdeeds for him. “I came in late a couple times.”

  “Three times to be exact. What else?”

  She thought a moment. “I came back late from lunch.”

  “Twice. What else?”

  She hesitated. Which should she own up to next— the typos or misspelling his name? They fell into the same category. “I made quite a few errors on several documents I typed up for you.”

  “Including spelling my name wrong just about every time you brought something into me for signature,” he pointed out. “There’s one more thing, though.”

  She had to resist the urge to fidget as she tried to remember what it was. She turned her head to look at him over her shoulder. Her pulse skipped a beat at the glint in his eyes. “I can’t recall anything else.”

  He lifted a brow. “What about the call you hung up on this afternoon?”

  Blushing, Sydney looked away. But not before she saw his mouth quirk. “I guess I forgot about that.”

  “I guess so.”

  Was there a slight trace of amusement in his voice? Had Max known what she was up to all along?

  Max brought his hand down hard on her ass, startling her.

  Sydney gasped. She’d forgotten the first spanking had been over her skirt. That one had stung, but this one burned even more. It didn’t help that her panties were practically nonexistent. With most of her ass cheeks exposed, the scrap of material might as well have been down around her thighs. The thought brought a rush of color to her cheeks just in time for another smack.

  “Owwww!”

  “You might want to keep the nois
e down,” Max said softly. “We wouldn’t want anyone to come walking in.”

  “Yes, sir,” she murmured. And bit her lip.

  Max went back to spanking her, even harder than before. That was fine with her. She wanted him to thoroughly warm her bottom this time so she could see if she liked it as much as she thought.

  That didn’t mean she didn’t protest anyway. Every time Max’s strong hand came down on her derriere, Sydney let out a quiet, little yelp through her clenched teeth. He alternated from one cheek to the other until her entire bottom was stinging. Then he concentrated the smacks on the tender area of her sit-spots. She danced on her high heels. As much as she wanted him to keep spanking her, she almost sagged with relief when he finally stopped. Her ass felt as if it was on fire.

  Sydney pushed herself upright and reached around to cup her poor ass. She gasped at how hot it felt. She wiggled her hips as she massaged her bottom. That’s when she realized her pussy was wet. She was practically dripping she was so turned on.

  She tried to hide her blush as she smoothed her short skirt over her hips. Her gaze strayed to her boss, and her eyes widened as she saw the huge erection tenting his dress pants. Obviously, Max was as turned on as she was.

  Tearing her gaze away from his crotch, she met his eyes. “Thank you, Mr. Daniels. I’m sure my work will be much better.”

  Max regarded her in silence for a moment, his dark eyes intense. “See that it is.”

  As she walked from the room, Sydney couldn’t resist putting a little more wiggle into her hips. She glanced over her shoulder to see what effect it had on her boss, and was quite pleased to see his gaze transfixed on her ass.

  * * *

  Max let his gaze follow Sydney until she disappeared into the outer office. His cock was so hard it was almost painful. What he wouldn’t give to bend his beautiful executive assistant over the desk and take her from behind.