The Dana Files - The Boss

I work with a woman named Dana. Gorgeous! Close to six feet tall. Long blonde hair that ran down to the middle of her back and wrapped around a thin, friendly face. Piercing blue eyes and ruby red lips. Her curves would make a great road course. 36-24-34. Long, long legs. And every inch tanned to perfection. Her smile and laugh lit up any room when you were lucky enough to be there. She was also painfully shy. She was a wallflower. You could usually find her standing next to a wall unless she was in a very small group of very good friends. Once you cracked through that wall, you found the true Dana. She was also, for lack of a better term, a people pleaser. Not so much because she wanted to do whatever was asked of her, but because she didn't like conflict of any kind. I never saw her say no to anyone.

She also has the naivete and innocence of a child.

The other day the CEO of our company, Roger Atkins, called her into his office. Roger is in his late 50s, but you would never know it to look at him. With his square-jaw, trim and fit, he appeared at least 10 years younger than he actually was. The only thing that might give him away was his salt-and-pepper (mostly salt) hair and white goatee.

Roger waved her in when she entered his mahogany-walled office covered in photos of himself with various celebrities and dignitaries.

"Come in, Dana, come in." He came around his dark wooden desk with floor-to-ceiling glass windows behind it and motioned to a chair in front of it. "Please, have a seat." Dana sat down and Roger leaned back against his desk directly in front of her. His angle gave him a perfect view down her deep v-neck sweater and the long, tan sticks protruding from her short skirt. He already had a hard on before she walked in. The view only made it worse. "Thanks for coming, Dana."

"No problem, Mr. Atkins!" Dana said cheerily.

"Okay, look, first of all, please call me Roger. We've known each other how long? How long have you worked here?"

"Oh gosh! Eight years, I think."

"Eight years?! Wow, how time flies. Calling me "mister" makes me feel old, Dana," he chuckled.

"Oh my gosh! I...I'm so sorry, Mis...Roger! That's not what I meant!"

Roger smiled and chuckled again. He waved a calming hand. "I know, I know. Just, please, we've worked together long enough. Please call me Roger." Danna smiled and nodded her head. "So, listen Dana, I'd like to ask you a favor."

"A favor? Sure, anything!"

"Great." We're about to find out. "You're a team player, aren't you, Dana?" She nodded her head. "And you want to see the company thrive, don't you?"

"Oh, yes! I love working here!"

"Great. You're a really big part of this company's success." That body really boosts the moral around here!

"Really? You think so?"

Roger nodded. "Oh, absolutely. But now I need to ask you to do something for me. I wouldn't ask this of just anybody. And this is just between you and me. We don't want anyone to get jealous or think I'm giving you special treatment, okay?"

"You have my word!" She ran her finger across her lips as if she was closing a zipper. "My lips are sealed!"

Not for long if this works! "Okay, here it is. I'm going to be completely honest with you, okay?" She nodded. Her eyes were wide. She thought for sure he was going to reveal company secrets. "Okay. There are several things going on right now that have me super stressed out."

Dana gasped. She hated to see anyone in even mild discomfort. "Oh no! Why's that? What can I do?"

"Okay. Well, maybe you haven't noticed, but this whole Covid thing has really hurt the business" Not really! "Customers just aren't buying advertising like they were before." They're buying more!

"Oh no! What can I do? Do you, you know, want me to be, like, a sales person or something?"

Roger shook his head. "No, nothing like that. But, it's got me stressed out. And when I go home, my wife says I'm grumpy, which makes her grumpy. Which isn't conducive to, you know, being intimate, you know? She said she's sick and tired of me coming home grumpy. So, then, her attitude only makes me grumpier, stresses me out more. It's a vicious cycle. See what I mean?"

"Um, yeah, sure, I guess."

"So, all of that has me super stressed out. You don't want me to be stressed and grumpy, do you, Dana?"

Dana shook her head. "Oh no! Absolutely not! Is there anything I can do?"

"Well, actually there is." Dana was on the edge of her seat. "Remember, this is just between you and me. I can't even think of asking anybody else because you're such a team player. I can't think of anyone better suited for this task."

Dana nodded. "Absolutely! Anything, just name it."

"Well..." He paused for dramatic effect. "One of the best stress relievers I know of is, well, sex."

Dana's eyebrows nearly flew off her head. "(GASP!) You...you want me to have sex with you?!"

"No no, nothing that extreme." Not yet anyway. "But a good hand job sure would do wonders.

"You...you want me to give you a hand job?!"

"You're a team player, aren't you, Dana? You want the company to succeed, don't you?"

"Well, yeah, sure..." she said hesitantly.

"The company can't succeed if I'm all stressed out, right?"

"Yeah, I guess. (GASP!) Oh my gosh!" Before she could finish the thought, Roger had his thick trouser snake out of its cage. It was pointed straight at her only inches from her face.

Roger gently waved it at her. "So, what'd ya say, Dana? Will you help me out? Help the company? Be a real team player?"

Her dimwitted and overly kind mind thought for a moment. She hated seeing people in discomfort, especially if there was something she could do to help.

"Well, I guess one little hand job won't hurt."

Roger smiled broadly. "That a girl." He watched intently as she raised her hand. She slowly, softly wrapped her long, thin fingers around his veiny shaft. "Mmmmm, that feels good," he moaned as she started to run her hand up and down his shaft. The tip was shiny with precum. She ran the palm of her hand over it and again slid it up and down.

"My goodness! It's so big! Does that feel good?" she asked innocently.

"Oh yeah, that feels great. It'd feel even better if, you know, it was lubed up a little bit."

"Oh! Of course!" She leaned her face over the swollen tip and dropped a string of a saliva across it. It ran down the meaty handle into her hand. "There. Is that better?"

"Oh yeah, that's great," he sighed. I can't believe she fell for it!

I can't believe I'm doing this! Dana thought to herself. It's so naughty! She could feel her body heat rise with every rise and fall of her hand.

A few moments later, Dana looked into Roger's face. "Is it working? Are you feeling relaxed?"

He nodded. "Oh yeah, it's definitely working. That feels great."

"Are you close?"

"Close? Close to...what?"

"You know...finishing."

"Oh! You mean cumming? Oh no, not really."

"Am I...am I doing something wrong?" she asked, truly concerned she wasn't pleasing him.

"Oh no! Absolutely not. You know what would help, though? If you took your shirt off."

"Took my shirt off?! Oh my goodness! What if...what if somebody walks in?"

Roger smiled. "Nobody's going to walk in."

"You really think it would help?"

A crooked grin crossed his nodding face. "Oh yeah, absolutely."

"Well...if you think it will help." She released him from her grip, then reached down, grabbed the base of her tight sweater, and lifted it up and over her head, revealing a lacy white bra. Her breasts were spilling out over the top. The fine lace did nothing to hide her pink areolas or restrain her thick, erect nipples. Roger's eyes widened at the sight. "The bra, too?"

Roger gulped hard. "Oh yeah, absolutely."

She shrugged her shoulders. "Okay," she said with the innocence of a child.

The straps slid down her arms and into her hands. She dropped it onto the sweater that was already on the floor.

"Whoa," Roger muttered under his breath.

Dana began to massage and knead her fleshy mounds. "Do you like them?"

Roger hypnotically nodded. "Oh yeah. They're incredible."

"Tee hee! That's what most men say. Wanna touch 'em?" He slowly reached out his beefy hand. "Mmmmmm," she purred when his hand touched her hot skin. "Do you like them?"

"Oh my God, yes," he panted. He got an evil grin. "Are you cold?'

"Oh!" she squealed when he pinched a nipple. "No. No, I'm not cold. Be...be careful with, you know, those. They're kind of sensitive. When a guy does, you know, that, it makes me crazy. Oh!"

"So, does this turn you on, Dana? Does the feeling of my cock in your hand make you excited?"

Her face turned red. "Well, maybe a little," she said with embarrassment.

"Just a little?" he asked with a hint of sarcasm.

Her face turned a brighter shade of red. "Well, maybe a little more. Do you...do you want me to go back to, you know, what...what we were doing?"

"Huh? Oh, right! Yes, absolutely."

He could sense her hand had grown warmer and clammier just in that brief pause. He groped at her exposed flesh while she went back to the task at hand.

My God! He's driving me crazy! All of this is driving me crazy! she thought to herself. A few more moments passed. She didn't feel the familiar throbbing of man's muscle before he's ready to explode. "Are...are you close?"

Roger shook his head. "No, not really," he said with a grin.

"Really? Most guys would have, you know, finished by now. Are you sure I'm doing it right?"

"Most guys? Do you jerk a lot of men off, Dana?" he asked with a slight hint of mocking.

"Oh! Oh no! Not at all! I...I'm not, you know, that kind of girl. It's just, you know, I've done, you know, enough to know that a man, uh, you know, usually does it by now."

"Well, I'm not most men, Dana."

"Oh! I know! It's just...I meant..."

"You know what would speed this up?"

"No, what?"

"If you sucked on it a little."

"Sucked on it?! You...you want me to, you know, give you a...a..."

"A blow job. Yes, I want you to suck my cock. Yes, exactly."

"Oh my goodness!" It looks so tasty! "But...but what if someone walks in?!"

"So, let me get this straight. You're okay with someone walking while you're topless and have my cock in your hand, but you draw the line at having my cock in your mouth. Is that it?"

"No! That...that's not what I meant. It's just..."

"Nobody's going to walk in, Dana."

"Well...I guess so. If you think it will help."

Roger nodded with a fiendish grin. "I know it will help." Two seconds later his body shivered. "Guh!" he croaked when he slipped past her lips. Her head quickly began to slide on his pole. His hands went to the back of her head. "Oh yeah, that's it. Suck it good, Dana. Suck my cock good and hard," he hissed.

"Mmmmmmm. Mmmmhmmm!" she moaned. My goodness he smells good!

He began to push harder on her head and pump his hips. "Come on, you cock sucking bitch. Take it all. Take it down your throat! Come on, take it all!" Her dives paused with each crash of his manhood against the back of her mouth. Then his head snapped back. "Ughah! Oh fuck yeah!" Her face landed in his lap. "I knew you could do it! Ha! This isn't the first cock you've swallowed, is it, you bitch?"

She slightly shook her head. "Mmmmhmmm! Mmmmhmmm!" My gosh! He tastes so good! I wonder what his stuff tastes like?

He had a handful of her long, blonde hair in one hand while the other groped her large, round globes. He filled her throat with every pump of his hips. Sweat began to roll off his face. The fire between Dana's legs was almost unbearable.

The buzz of the intercom speaker on his desk broke through the gurgles and groans. Roger removed his hand from her breast and pressed the button.

"What is it?" he growled.

"Mr. James is here to see you." Matt James was one of the firm's biggest clients. Dana's ears perked up. A slight panic coursed through her at the thought of someone being here to see the man who's cock was in her throat.

"Matt's here? What the...do I have a meeting scheduled with him?"

"No, sir."

"Goddammit," Roger grumbled. "Tell him to come back..." The corners of his lips curled up. "No, wait. Go ahead and send him in."

Dana's heart stopped. Her head shot out of his lap. She looked at Roger with a horrified look on her face. "But...but he'll see!"

"Who told you to fucking stop?!" Roger slammed her face back into his groin. She coughed at the sudden rough intrusion into her throat.

The door opened and Matt James walked through the door. Some would refer to him as an elder statesman. He'd been in the game for years. He'd even run for Senator twice, barely losing to the incumbent both times. A tall, handsome man with finely manicured hair of white parted and combed to the side, he walked in wearing a pair a dress slacks and a freshly pressed white dress shirt.

He thought nothing of the bare-backed woman sitting directly in front of Roger. Women dress so casually these days! Probably wearing a halter top or something. However, he was so distracted by the long blonde hair cascading down the deeply tanned back, he didn't even notice the slight bobbing of her head. He closed the door behind him and walked into the room.

"Hey, Roger! I just happened to be in the neighborhood so I..." Then he saw what was going on. "Christ almighty! What the fuck?!"

Dana froze at the words. That didn't stop Roger from thrusting into her throat.

Roger winked at his friend. "Hey, Matt, how goes it," he said as nonchalantly as possible.

Matt's eyes bounced from the face being impaled to Roger's broad smile. "What...what...what the fuck?"

"What? Oh, this?" He nodded down. "Oh, this is just Dana performing a relaxation exercise. Isn't that right, Dana?"

"Mmmmhmmm! Mmmmhmmm!"

"No shit?"

"No shit. Say, Matt, you've been looking a little stressed lately."

"Huh?"

"I sa-a-a-aid..." He nodded down towards Dana again. "You've been looking a little stressed lately.

Then it hit Matt. "Oh! Right! Uh, yeah, oh yeah. Really stressed."

"Why don't you have a seat here and see if Dana can help you relax," Roger said, trying not to chuckle.

Dana's heart stopped. Huh?!

Roger grabbed her by her long hair and yanked her out of his crotch. "Matt here is a little stressed, too. Maybe you can help him out?"

"But...but I..."

"Come on, Dana," Roger said in a very sympathetic tone. "Matt's one our biggest customers. You don't want to lose that business, do you?"

"Well, no."

"You heard him. He's really stressed out. He needs your help. We need your help. The company needs you, Dana."

"Really?"

"Absolutely! You're vital to this company, Dana. The services you provide are invaluable!"

"Gee. I had no idea!" The company needs me! Roger needs me! Mr. James needs me! "I certainly don't want to let you down." She turned to Matt. "I'll be glad to help you!"

That was the first time Matt had gotten a full frontal. "Sweet Jesus, look at those tits!" Roger burst out in laughter.

Dana cupped and caressed her fleshy mounds. "Tee hee! You like 'em?"

"Like 'em?! Sweetheart, the hand of God has touched you in all the right places."

"Gee, thanks," she cooed. "Now let's see if I can help you relax." She slid off her chair onto her knees and scooted the short distance until she was between Matt's legs. He watched her hands fall into his lap with bated breath. The sound of his zipper broke the silence. "Now, let's see what you've brought me."

Matt grunted when she reached into his slacks and gripped his python. She subconsciously licked her lips when she pulled it out of hiding.

"Mmmmmm, look at you," she said as she began to stroke and study it. He wasn't nearly as large or thick as Roger, but he would certainly please any woman.

"Why don't you skip all the preliminaries and just shove it down your throat, Dana?" Roger suggested as he stroked himself.

She turned his head to him. "Really? You think so?"

"Absolutely. Show him what a great cock gobbler you are."

"Oh! Tee hee. Okay!"

"Ga-Christ!" Matt barked when Dana took him into her mouth. After one-two-three bobs of her head, "Holy Mother Mary! Fuck! She...she...fuck! She swallowed the whole goddamn thing!"

Roger gave a loud laugh while Dana had a muffled giggle. Matt's hands went straight to the back of her head.

It wasn't long before Roger slid off his desk and bent over. He grabbed Dana by her ample hips and lifted her.

"Hmmm?" Dana hummed. "Hmmmm?!" she squeaked when she felt a cold rush of air across her heart-shaped ass when Roger threw her skirt onto her back.

"Look at you with your sexy little thong," Roger jeered. "Why even wear anything?" Dana yelped when Roger in one smooth motion tugged and snapped the thin material off her body. She raised onto the balls of her feet and chirped when Roger ran his finger along her swollen slit. "Dana, look at you. You're soaked!"

"Mmmmmm! Mmmmmhmmmm!"

"All of this cock has you wanting more, doesn't it, Dana?" he mocked as he continued to tease her gash.

"Mmmmmmhmmmm! Mmmmmhmmmm!" He's driving me crazy! She gasped when he replaced his finger with the tip she'd been sucking on only minutes ago.

"You want me to fuck you, don't you, Dana? You want me to fuck you like a little slut while you suck on that cock, don't you?"

"Mmmmhmmm! Mmmmmhmmmm!" Please! Please fuck me with that fat cock! Oh my God, I'm going crazy! "GGGGGFFFFFFKKKKKK!" she barked when Roger landed balls deep.

"Holy fuck! That's one tight cunt!" Roger announced.

The room quickly filled with the sounds of moans, groans, cursing, and slurping. The two men used Dana like a $2 whore. Each drive of Roger's body buried Dana's nose into Matt's stomach harder and his tool down her throat deeper.

Matt looked across Dana's back. "Jesus, Roger, where'd you find this one at? She must've cost you a pretty penny!"

"Ha! She works for me! Ha ha!"

"No shit?! You lucky bastard!"

He thinks Roger's lucky to have me working for him! Isn't that sweet?!

Dana had herself worked into a frenzy before Roger had begun to pound her honey hole. He could feel her muscles begin to twitch around his post.

"Ha ha! She's about to cum like a little whore! You're about to cum, aren't you, Dana?!"

"Mmmmhmmmm! Mmmmmmhmmmm!" CRACK! SQUEAL! Roger left a red hand print on her backside. Her body temperature continued to rise. She felt like she was going to explode.

The buzz of the intercom sliced through the thick air.

Roger slapped the button. "What?!" he barked.

"Eric Brooks is on line one," came the calm reply. Eric was a supplier for Roger who was always looking to get more business from him. He was constantly offering Roger different perks.

"Fuck!" Roger thought for a moment. This might be fun! "Put him through!" Matt's eyebrows raised.

Huh?! He's going to talk to someone on the phone while he's having sex with me?!

"Hey...hey, uh, Eric? How...how are you?" Roger stammered.

"Hey, you old bastard!" crackled the response. "Whatcha up to? Am I interrupting anything?"

"No...no. Just...mmmmm...just fuck...fucking one of the cunts in...in the office."

"Ha ha ha! You wish! Ha ha ha! It wouldn't happen to be that tall blonde? Tell me it's that tall blonde! No, wait, don't tell. If you say it's her I might cream my jeans right here just a the thought of it! What was her name? Dana, I think?"

Dana gasped around Matt's rod in her throat. Is...is he talking about me?! The fire between her legs was almost unbearable. Her legs started to tremble.

"Yup...yup. That's the one! Tight...tight little...mmmmm...cunt!"

"Ha ha ha! Yeah, okay, whatever. I wouldn't mind having her drink my hose! Man, she's got a tight little body! You think you might be able to hook me up with her?"