His Mistress was his Master

As he approached his office, with his beautiful assistant, Penny on the phone and scribbling notes, he loosened his tie. She brightened at the sight of him, and held up a finger as she finished her phone call. "Congratulations Mister Dean," she said when she had finally hung up. "I heard about the success of the meeting with the Fassbender's went today. I'm excited for you and your success."

James looked stern, "Thank you, Penny. Did you get everything I asked you to get done?"

She rolled her eyes, "Yes, but only cuz' you haven't asked me to do anything for two days. Where have you been?"

"I was working."

"Bullshit, sir. You look like you were sleep the whole time."

"Are you calling me a liar?"

Penny became immobile and silent.

James looked around, but knew no one would be here this late, "In my office."

James walked into his office with Penny in tow, ready to spank her for her insolence, but the tub of ice and bottle on his desk distracted him. A quick glance told him it was the same bottle Slade was currently drinking while plowing Susan. A scribbled note said, "Kid, you rise to the top like cream. Keep it up. Slade"

"You gonna cry now?" Penny asked behind him as she wrapped her arms around his muscley frame.

He laughed, "No, I was gonna spank you, but the old man softened my heart. Close the door if you don't mind, and put up your hair, that's a mandate." She grinned as she hopped towards the door.

Penny was a light-skinned black girl, of about twenty five with natural tiny breasts, and a nice ass and sandy brown hair. She had been Slade's assistant until he had passed her off to James, later telling him that he couldn't even get her to blow him. This surprised James, as the afternoon Slade had introduced them, James had ass-fucked Penny over his desk. That was in the old building, where James was even more tucked away, and could bone in his office no problem. He had also fucked Slade's new assistant Susan, but he doubted Slade cared very much.

Penny was tying her shoulder length hair into a bun and was sauntering back to James sitting in his comfortable chair. She sat on his lap and the two tongue kissed a little while he grabbed her tight ass. "You gonna loosen up now?"

James had been rough on Penny over the last few weeks with the then impending meeting putting heavy stress on him. She had taken it all in stride, and James had to remember to give her a bit of a bonus. "I'll try." She kissed him and grabbed his hardening cock through his pants. "You should," she said taking off her sports coat. She had a calf-length skirt which showed off her amazing shape and a white low-cut shirt which showed her small natural breasts well. "You've just made Slade a lot of money, and yourself as well. So. Just. Relax. A. Little." She kissed him all over in between each word. He pulled her in and started kissing her chest, to which she responded with a moan.

Soon, he had her topless and was working her soft yellow nipples into his mouth. She groaned at this and jerked his hard cock through his pants. "Can I suck you, Mr Dean?"

She took his grin as a yes and began to kiss down his chest. "Relax," she said, "Have a drink."

James finally did relax as she fished his thick cock from his trousers and began to plant little kisses. He swiveled in his chair and threw a couple ice cubes into a glass, before opening the decades old bottle of liquor. He sniffed it a little before pouring himself a healthy amount into the glass. This entire time Penny planted little pecks on his cock. But when he returned his concentration to her, she started gulping his cock like she was suffocating and it was air. James let out a guttural moan. He was getting into it when his phone rang on the desk. He answered without looking and answered, "Dean."

He was greeted by the shrill voice of his mistress, "Who are you talking to like that?"

James stood up immediately knocking Penny backwards. He covered his mouth piece and shouted, "Out, get out!" she looked hurt and confused, but this wasn't the first time he had hurt her, so she gathered her clothes and left.

When she had gone, he said back into the phone, "I'm sorry my queen, I rushed out of a meeting."

"You sacrifice your career over some sex? Pathetic, you'll never get anywhere, don't know why I bother."

"No, mistress!" he pleaded, "The meeting was already over. Just wrapping up." He cleared his throat. "And I think it went rather well."

"Whatever," his mistress said boredly, "Two hours be here with some wine. Don't touch that filthy cock of yours, I want a huge load in this pussy. And shower my dirty boy. And don't wear a gray suit."

James stammered a 'yes, mistress' after every sentence, and was cut off by the dial tone.

He sighed before he capped the whiskey bottle before putting it in the cupboard with his other fine bottles. He then dressed and, jacket in hand, shuffled out of his huge office. He knew she wouldn't be, but would have liked to see Penny sitting at her desk so he could have a chance to apologize. He would have to send candy and jewelry to her home as well as writing her a bonus.

***

James was wrapping up telling his mistress about his meeting, and she was looking rather impressed. She was a short-haired blond woman of about 55. Her breasts were huge, and she was wearing a partially see-through teddy and sat cross legged eating salmon as she listened to her pupil give her his doings.

"Wow, James, you certainly have come far from when I took you under my wing at 19."

"Yes, mistress."

"You started so slowly, but once you got the hang of it," she shook her head. "Along with other things. She grabbed his smooth chin tightly and looked him in his eyes. She let go and downed her glass of vintage red wine, and his as well. She unfolded her legs to expose a beautiful pussy with a patch of hair above the clitoris. It was beautiful, and James couldn't wait for it to use it's tricks on him.

"You know what to do," she said, pouring herself another glass.

James wasted no time, slipping from his chair and crawling to hers. He took one of her perfectly pedicured feet, beautiful red nail polish, and he began to softly kiss her feet and then up her legs. "You want to eat your mistress' pussy don't you?"

James nodded feverishly. She glared at him. "How many young whores did you fuck this week."

He flinched and lied, "Just one mistress."

She scoffed, "Yea, yea. How'd you get her?"

"I made her feel like she couldn't say no," James said.

His mistress smiled, "Just how I taught you. But you used this girl didn't you?"

"Yes, mistress."

"You used your superior intellect to prey on her didn't you?"

"Yes mistress"

"I know you did, you little asshole." She grabbed his chin again and face to face they were again. "I have something for you."

James groaned. "What?" she said? "Nothing mistress."

She looked at him, still massaging and kissing her feet and kicked at him before bustling from the room. She quickly returned with a four inch butt plug, it was slick with something. "Raise your ass," she instructed, and James lifted his ass in the air. She sat the plug down and lowered James back onto it slowly. It burned very uncomfortably for James, though this wasn't the first time she had used this on him. "Because you're an asshole, I'm taking your asshole. Okay?"

"Yes, mistress," he groaned. She then turned and put her asshole right in his face. He furiously ate it for a few minutes before she let him breathe. "This isn't even a punishment for you is it my dirty boy? You love your mistress' ass."

He just nodded as she looked down at him, "Pathetic. Sitting on a butt plug, eating ass, I bet you couldn't even please a woman-"

She was cut off by James swift movement. He had hopped off the butt plug, spit onto his cock tip, and slipped it into his mistress' tight pussy. She groaned when he put it in, and moaned as he started to move in and out. she moaned faint "how dare you"s and the like but she was obviously enjoying it. He then pushed her onto her stomach on the kitchen floor and started probing her guts with his entire length as she groaned under him. Just as he felt he was beginning to come, she hopped from under him.

She turned to face him and slapped him in the face. Although her faint smile and still dripping pussy would say otherwise, she was acting indignant. "Who told you you could fuck your mistress?!"

James hung his head. "Come with me, asshole, and bring your friend." James reluctantly grabbed the butt plug as he followed his mistress into her bedroom, where she had candles lit throughout the room. "Give me this," she said taking the plug and putting it on the center of the bed. "Sit" she said simply, and James did sitting his ass right on the plug. Less burning this time.

"You think you fuck good, asshole?"

"No, mistress."

"You damn, right you don't. There's more to love making than brute force."

"Yes, mistress."

She grabbed his softening cock and started jacking it, before she started gobbling it to his moans of delight. It was hard again almost immediately.

"Did you make her come?"

James thought to himself that he made both Lena and Jasmine come in eerily similar ways an hour apart, but he said, "Yes, mistress."

"She made you use a condom didn't she?"

"Yes, mistress."

"Of course she did. What type of player can't even hit a barmaid raw? Good thing I guess since you're burying your dirty dick in my womb without asking. You know how many people beg to eat my ass? Beg to fuck this pussy? You're lucky I even let you kiss my feet let alone get near my pussy."

"Yes, mistress."

"Was that little skank as hot as me?"

"No, mistress, not even close," he said truthfully. Lena was hot, and so was Jasmine, but his mistress was his type of woman, and plus, they were amateurs."

She seemed to genuinely like his response and started to gag on his dick.

"You know you ain't shit don't you?"

"Yes, mistress?"

"You know that if you didn't fuck her, some better looking man with a huger dick would have, and he still might and it'll make her forget about you!"

"Yes, mistress."

She then climbed his face, and placed her pussy upon it, he hungrily lapped it up, but her added weight pushed him down onto the butt plug, upping the burning sensation. "Eat my pussy, dirty boy. Eat it all night until I'm ready to fuck you."

"Yes, mistress" he moaned, as the plug found a different angle and started scraping his prostate.

The lovers banged their bodies against each other, with James pushing up against the plug, and his mistress pushing onto his face. She finally got up and pulled off her teddy. He began kneading and sucking her huge mature titties with the large brown nipples. She moaned and jerked his cock and noticed the plug. "I forgot i even put this here. Are you enjoying it?" he didn't answer, just kept slurping titties. "Yea you like it. I hope you have a big load for me." She removed her tit from his hand, and spit onto his cock head, and slowly lowered her pussy onto his giant cock. The weight on his lap caused him to sink deeper onto the plug, and they both moaned as they adjusted for the foreign objects filling their bodies.

James sucked his mistress' fat titties as she hopped up and down on his giant cock, tight pussy clamping the shaft. He smacked her giant ass, and tried to match her thrusts, noticing as he did that he was fucking the plug as well. Soon he was bouncing more on the plug than actually fucking his mistress, and his mouth began to salivate. He was fucking the plug, which pressed against his prostate with every down thrust with abandon. He was in a trance when his mistress called out, "YES RIGHT THERE DON'T STOP!"

He had quite literally forgotten she was on his cock, as he was completely concerned with the warmth in his ass. But apparently he was stabbing her pussy in the right way because she came hard, and for the second time that week, James felt like his cock was stuck in a cement mixer. As his mistress moaned her orgasm, James bounced once more on the plug, hitting the spot, and that along with the pussy tightness caused him to shoot rope after rope into his mistress' waiting womb. They both moaned as their orgasms subsided and they fall over fall asleep.

James woke up at 5 AM the next morning alone in his mistress' bed. She had sent him a text. "Have to keep moving my dirty boy, we both know it. Mama's proud of you."

James rather embarrassed, took the plug from his ass, dressed, and drove across town to his apartment.