Yes Mistress

Four

It was the next day and Ruby was currently at her apartment. She lived in a tall building and loved the fearing view. When she got dressed and made her way to her office , she noticed how everyone was looking at her. Meaning something was wrong. "What did you do Blake?!"

"It wasn't me this time I swear , just go look in your office ma'am!" Blake defended as he leaned his head down.

She clutched her fist before smiling and walking inside her office. When she stepped in she smirked as she shook her head. "Alex f*****g Vixens. What is this , your second home or something? What , do you want me to f**k you?"

"f**k no. I'm here because I'm suppose to be here Ruby." Alex says as he stood up and walked over to her desk. "Did you do something weird to Michael? Why is he acting weird? Did you f**k him?"

Ruby blinked a couple of times before laughing and shaking her head. "Oh.. oh my god! Haha! Wait are you serious? And if I did what does it matter to you puppy?" She clutched her stomach as more laughter and tears erupted.

Alex bit his lips before he walked up to her and firmly placing a hand on her desk. "I don't want you touching Michael." He mumbled.

"I'll do what I want. You should really mind what you say , I might do something bad." She said as the door opened , it was Jessie. "Jessie you need to learn to knock."

"I-I'm sorry." Jessie whispered as he rushed his way behind her chair.

"And Alex please leave , you're bothering me." She waved off tiredly as she looked through the documents in front.

Alex smirked before he proceeded out. Ruby clasped her hands together before sighing. As much as she hated Alex and Michael, she never was serious with her words. Besides she liked to have fun. "W-What was that about?" Jessie says as he looked down to her.

"Business." She mumbled as she pulled some documents out. "Tell me my plans for today."

Jessie clears his throat before beginning to speak. "You only have a meeting with your father and some work at night to compete. Should I stay to drive you home?"

"No that's fine thank you , you can leave early today." She smiled as she waved her hand. Jessie frowned as he thought. Was something wrong? She seemed upset.

He clears his throat before holding the top of her chair. "Is everything okay? Can I help you with a-anything?" He asked as he leaned to her side. She looked down to him before smirking. 

She wanted to take things slow but in the end , tease the hell out of him. She gripped his hair and smiled. "Nope! You can leave Jessie." She says as she let's go.

Jessie titled his head , he was confused. "Oh.. okay..." He mumbled as he left the room. She laughed softly as she shook her head. 

He was more needy than her last assistant.

-

It was around the time she had to meet her father and she groaned when she saw Marina. Marina was submissive who normally came because of money but her father was blinded by her beauty. "Ruby dear! It's been too long."

"Marina yes it has. How are you?" She said  as she sat down , she didn't see her father anywhere.

"I'm okay. Your father and I have a surprise for you." She smiled sweetly. Oh she was such a fake.

Ruby smirked. "Okay." She said as she saw her father enter the office. "It's not right for you to be late dad." She narrows her eyes as she crossed her arms on her chest.

"Love you too Ruby. Where's Alex?" He asked as he sat down and placed his hand on Marina's leg.

"I told you , he's not my puppy anymore so I called it quits." She brushed off as she downed the drink in her hand.

Before Alex became a CEO of his company , he use to be Ruby's submissive. Since their high school days were filled with crazy ness , Alex could never leave her be. 

"Well that's just sad. I was too drunk that I didn't even notice." He joked as he downed the whiskey drink.

Ruby sighed as she looked up. "So what is this about?"

"Ah right. I wanted to let you know that me and Marina are... getting married." He cheered as he smiled.

Ruby looked at him in confusion. "Dad you can't get married to Marina, you have a wife who is my mother." She said as she shook her head.

Her father simply laughed as he shook his head. "Actually , I wanted another submissive and I'm in love with Marina. You're mother was actually the one who wanted this to happen my my , you should have seen her reaction." He teased as he thought about yesterday's events.

"Well as long as everyone's happy , I couldn't give two shits. I'm leaving." She waved off as she left the room.

She didn't mind them because this wasn't the first time her mother and father wanted to be experimental. 

When she got to her office she nearly yelled as she saw Jessie. But she blushed whenever she saw how he was.

He was sitting on the floor with his legs crossed and a nice black collar on his neck. Ruby inhaled before walking past him. "Jessie what's this? Acting so pretty in front of me."

"W-well the last assistant told me that whenever you were having a bad day that I was to please you until you were satisfied." He mumbled as he gripped the end of the collar. He placed it in his hands and handed it to her. "Please?"

She softly chuckled as she gripped the end of the collar tightly and brought it to her. "Let's go out for a walk again ? I think I need a break." She whispered as she brought him up. She flipped him over until he was laid on the desk and she hummed. She brought his personal vibrater  (she kept it with her all the time) and placed it near him. She made sure his clothing was fully off and she grabbed lube to moist his area.

He was shaking with anticipation, wanting to do the extreme. "M-mistress , what if someone..."

"Then that would be no fun my puppy , you're just gonna have to endure it." She whispered as she grabbed a long jacketed that covered his whole body. She placed the toy in his hole making him whimper softly. "Shall we go for a walk now?" She teased.

He looked down at himself. He was praying that she wouldn't do  this again because he was weak to this. "B-But I'm completely naked."

"No one can see you. Come on it's dark , let's go." She winked as gripped the collar.

-

It was around midnight in a park and Ruby was calmly texting on her phone. Meanwhile Jessie was a mess. His trembling body , his soft moans and his messy body. He was cute. "Mrs.Hastings , I really can't a-anymore." He stuttered as he clings to her arm for support.

Ruby simply laughed as she shook her head. "I understand. Hold it for me a little bit longer." She whispered as she turned the volume up. He immediately yelped in pure agony. "Oh my."

Jessie tried to cover his legs up the best he could but it was obvious something was up. Jessie heard soft voices and he looked up , his eyes becoming horrified. "There's people!" He whispered.

Ruby licked her lips as she pulled him down on the bench. She sat on his lap , wrapping her arms around his neck and bring him in close. Jessie didn't know what was happening but he couldn't handle the contact. His breathing became more hoarse and heavy. "I-it's gonna come out Mistress."

Ruby watched as the people left and she got off his lap. She brought the volume down just as soon as he was going to release making him whine in defeat. She smiled softly as she brought her hand to his cheek. He looked up at her , his sweat trickling down his skin. "I should help you ... look how needy it's becoming." She coos as she grabbed his hand and began walking to her car.

When she got to her car , she laid him in the back and hovered over him. His eyes shifted to her lips and he had the urge to kiss her but she only shook her head. "No kissing." She mumbled as lifted her hands to his erection.

His held his mouth as he started to pant whenever she shifted his shaft. His eyes traveled to her as she licked his neck. "My... you're the second sub who has ever made me this happy." She mumbled as she went faster.

"T-thank y- Ah!" He moaned out at his release. He shivered as his eyes  went to the side. 

Ruby licked her lips as she brought all of his c*m on his bare chest. "Good boy."