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Good Girl Carly And Her Boss

"Carly is a good girl, but when she accidentally seduces her boss, she finds out being bad is fun"

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Carly straightened her plain, grey skirt that hung loose from her hips. She buttoned the top button of her white silk blouse and pinned a stray curl back into the bun on top of her head. She looked in the mirror. “I look ridiculous,” she murmured to herself. Carly needed money, and now she needed a job. Her parents stopped sending her allowance when her GPA dropped her first semester in college. Carly’s roommate, Blair, offered to get her a job at The Spur, the local dive-bar. But that involved immature frat boys and that wasn’t Carly’s scene. She turned away from the mirror, grabbed her keys, and drove to her first job interview. 

Michael stared at the prim girl sitting in front of him. She sat nervously, perched on the edge of her chair, fiddling with the hem of her skirt. He needed a new assistant after his last one quit. Well his last one didn’t quit; he had to let her go after his wife caught him fucking the girl in the ass. It didn’t help that he was fucking her at home. On his wife’s newly reupholstered antique sofa. Michael needed to hire someone, and he needed to not think about fucking the girl he hired 24/7. Michael stared at the plain girl in front of him, she didn’t wear any makeup, her shirt was button up to her neck and her skirt was practically a tent.

“You’re hired,” he said and watched as her face lit up in joy.

“Wow, thank you so much! I really appreciate—” 

“You can start tomorrow, I’ll be out until around 1:30, so come in at 2pm.” As he shook her hand and watched as she left he was confident he made a safe choice.

“What do you mean you need me to cover your shift? I can’t, I start work tomorrow. Isn’t there anyone else?” Carly threw her hands up in frustration. Blair had a fever and chills and needed someone to cover her shift at The Spur.

“Everyone else has a class or something else going on. Please! It’s just from 9am to noon, and no one ever goes in at that time, you can just chill and do homework. Seriously, the place will be empty, you just have to babysit the register, and maybe serve coffee if some dumb tourist wanders in.”

“Darn it. Fine. But you totally owe me,” Carly was about to leave Blair’s room but twirled back around, “Wait… do I still have to wear that stupid uniform?”

“Yes! And it’s not so bad. I actually think you’d look hot as fuck in it. And you have to wear full makeup. Doesn’t matter if no one comes in, Pervy Sam likes to sneak peaks at his waitresses.” 

Carly spent all morning avoiding Pervy Sam’s come-ons and finally when she did leave The Spur she couldn’t get her car to start. “Shoot!” she kicked the tire, “Now I have to take the bus, which leaves me no time to go home and get changed for the office.” She looked down at what she was wearing… “I hope I don’t get fired...”

“Take off your coat, and let’s—” Michael nearly dropped his coffee when Carly walked into his office and awkwardly took off her knee-length pea coat. He scanned her from head to toe. Her long blonde hair hung in loose waves down her back, her eyes shone bright blue with the outline of eyeliner and mascara, and her lips were bright red. She wore a tight, nearly see-through pink shirt that was cropped, showing off her trim waist. Michael swallowed hard. She clearly wasn’t wearing a bra. He could almost see the hue of her nipples. She wore tight black shorts cut so high they exposed her round ass. And to top it all off she had three inch black strappy heels on. When Michael finally looked up he saw her awkwardly crossing her arms, trying to use her coat to cover her exposed waist.

“Come on in,” he waved her inside and before shutting the door he checked to make sure no one saw what Carly was wearing. He quickly turned the blinds. “Well…” He forgot what he was going to say as he watched her large breasts bounce as she walked further inside the office. “I think it’s best if you work in my office today. Don’t want to distract any of those young bucks. That would be an HR nightmare. You understand.”

“Yes, I’m so sorry for showing up like this, I was covering a shift for my—”

“It doesn’t matter. Really. I think you’ll come to realize that I can be a very flexible boss… And very generous.”

Carly didn’t understand what he meant but she blushed profusely anyways. Michael took note of her innocent blush and knew better than to push her to far today. Instead he spent the rest of the day behind his desk hiding his massive erection. Carly stayed in his office the entirety of the day, focusing on editing and organizing files. She was extremely grateful Michael turned a blind eye to her slutty attire. She counted herself lucky to have such a laidback boss.

At the end of the day Michael helped her into her pea coat, and as she put her hand on the doorknob he pressed his palm against the door. Carly looked up at him in confusion.

“This is for you.” He held out a $100 bill. Carly looked at the bill and then looked up at him in confusion.

“I don’t understand? Am I getting paid early?” Her tongue darted out to moisten her dry lips.

“No. You’ll still get paid on the 1 st. This,” he held the bill up, “is extra. Let’s just say I like your...” his eyes raked her from head to toe, “your sense of style.”

Carly stared at him with shock and indignation. Her mouth was slightly open, she waited for the right words to come but she just stared at him. Michael gave her a boyish grin, folded the $100 bill, placed it in her hand, and opened the door for her. He chuckled as she nearly ran out the door.

Carly’s heart was pounding as she drove home. She read stories about weird bosses but she never expected it to happen to her. She felt a warmth in her pussy and she rubbed her legs together. She couldn’t believe she got wet from that interaction. Michael was an older man, but he wasn’t old. He was probably in his fifties. He had a full head of hair that was sprinkled with grey. He wasn’t out of shape. Carly knit her eyebrows together… “In fact, he’s actually sort of good looking,” Carly was shocked by her own train of thought. Carly grew up in a very conservative family and came from a very religious background, and although college had helped her loosen up, she had only ever touched one cock before, and it wasn’t a good experience, the guy stayed limp the whole time, leaving Carly to question her own sex appeal.

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The next morning, as she was getting dressed, she thought about raiding her roommate’s closet for something scandalous, but she decided against it, instead opting for a demure beige dress. That day Michael was surprisingly polite. He didn’t address Carly’s attire yesterday or their little interaction. And at the end of the day Carly said goodbye and Michael smiled politely. A part of Carly wanted to go back into his office and demand… demand… something, but she didn’t know what. She was frustrated. She really needed that $100 to make rent, and yesterday was the first time in her life she felt sexy. She left the office and made up her mind. Tomorrow would be different. Tomorrow she would be different.

Carly woke up early and curled her hair, painstakingly applied her makeup perfectly, and then raided Blair’s closet. She finally decided upon a tight black miniskirt and a nearly see-through pink crop top. And to accent the see-throughness of the miniskirt she wore a tiny gold G-string thong. To complete the look she wore her strappy black heels. She twirled in front of her mirror, appreciating her long blonde hair and how her breasts bounced uncontrollably. Carly wasn’t planning on fucking Michael, in fact, she made up her mind she wasn’t going to do anything with him at all. “Well, maybe an innocent kiss, that’s it though,” she thought to herself. She prized her purity and wasn’t going to compromise herself. She just wanted to tease him a bit. And she wanted another $100.

Michael glanced up from his computer when Carly strutted into his office. He was about to mumble some nonsense polite greeting when she slowly peeled off her coat. If he thought she was sexy two days ago, that was nothing compared to what stood in front of him now. Michael was one step away from throwing her down on the desk and fucking her. Instead he cleared his throat, closed the door behind her, shut the blinds and then went back to his chair. Carly stood there watching him, a smug smile played across her lips. 

Michael thought to himself, “Let’s see if I can fuck that smug smile off her mouth.”

He grabbed a pencil off his desk and threw it in the middle of the room. “Pick that up.”

Carly watched him in confusion, and then quickly picked up the pencil and brought it back to him.

He frowned slightly, “You’re going to need some more training. Let’s try that again…”

Carly’s mouth made an ‘o’. Understanding slowly dawned on her. This time she walked over to the pencil, turned around so her round ass faced him, and slowly bent down for the pencil. Michael watched her every movement. His mouth got dry when she bent over and he saw that tiny sliver of gold material covering her pussy lips. She paused and Michael leaned forward in his chair, slowly she stood back up and sashayed over to him.

“Good girl,” Michael licked his lips and took the pencil from her. He stared at her pert nipples and imagined filling his hands with her large breasts. He continued to stare, enjoying watching Carly become uncomfortable under his gaze. My little seductress is far more innocent than she knows, he thought as he leaned back in his chair. Michael beckoned her closer and as she bent down to him he reached forward, touching the tip of his finger to her red lips. Slowly he pushed his finger into her mouth. Her eyes widened and she pulled her head away. Michael chuckled to himself and was pleased she didn’t step back from him. She knows how to follow directions.

Michael touched her lips again and traced his finger down her neck, down the valley between her large breasts, smiling as he watched her nipples become impossibly hard. He skimmed his finger down her taut belly and hooked his finger in the band of her skimpy miniskirt and pulled her closer to him. Carly ungracefully stumbled forward towards him. Michael picked up the pencil and twirled it in his fingers. Carly watched the pencil spin around. She didn’t want things to get out of control with Michael, but she was curious. Michael traced the eraser on the pencil around her belly button, very slowly and very gently.
Then he skimmed the eraser up her belly. He used the eraser to slowly push her pink crop top up higher and higher. Soon he could see the soft skin right under her breast. He pushed her top up higher until her nipple threatened to be released from its see-through confines. As the flimsy material was pushed away and her nipple hardened to the cold air, Carly gasped.

Her breasts were so large and perky, Michael wanted to yank her forward and suck her nipples until she was wet and begging for his cock. Instead, he moved the eraser to the other breast and exposed it to his hungry gaze. Carly looked down at her naked breasts. No one other than herself had ever seen her breasts before.

Carly didn’t know what to do. Part of her wanted to slap him and run out of the office. Another part of her was curious where this would go. Michael watched the emotions play across her face. He knew she was fighting a mental battle. And he knew he would win.

“Take the skirt off.” His voice was firm and left no room for discussion.

Carly chewed her lip and slowly peeled her skirt off. Leaving her standing in front of Michael with her tits hanging out of her top, in a skimpy thong and her high heels.

“Perfection,” Michael said under his breath. When the skirt was removed he sat forward in his chair and brought the pencil up to her breasts. He traced the tip of the eraser under one breast and then circled her nipple. Carly inhaled sharply. Michael smiled and traced the eraser down her belly and over her gold thong. “Spread your legs,” he said in an authoritative voice.

Carly complied and stepped her feet about sixteen inches apart. Michael traced the eraser down her gold thong and stopped when he heard a soft whimper escape Carly’s mouth. He'd found her clit. Carly didn’t know what to do, her thoughts became fuzzy and the feeling between her thighs was becoming stronger and almost urgent. She couldn’t believe Michael touched her in that spot. Not even she touched that spot! She couldn’t let him do this, she wouldn’t! Right as she decided she would stop this she felt his finger ram into her tight, dripping wet pussy.

Published 
Written by luckyalbreque
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