Alana had always been happy with the way things were. She worked at a corporation where hardly anyone knew her name. She dated Pete a nice man about ten years older than her. He worked as a lawyer and so she lived comfortably. Then there was Brendan.  

He was new to the building. He was the cliche started in the mail room and was getting noticed fast. He was twenty-four, young and fit. He had dark hair brown eyes and if she was being perfectly honest an ass that just wouldn’t quit. She shouldn’t be ogling him. She was thirty-four and in a semi-happy relationship, but every time the mail came she watched him with hungry eyes. She as losing her mind. 

Late one Friday evening it was her turn to lock up. Almost all of the employees had left papers strewn about their desks. It was quiet. Brendan came in with an envelope. He set it on a desk. She couldn’t help but stare at him.

“Hello, are you the only one here?” 

“Yes, I’m locking up tonight. What are you still doing here?” she asked a little more breathless than she’d like to admit. Her C cup tits heaved every time her eyes met his. “What are you still doing here?” He walked towards her until she was flush against her cubicle wall.

He bent down. “I’ve seen you staring at me.” She blushed. “I would like to fuck you for real like you’ve been doing to me with you’re eyes.”

She couldn’t believe her ears. She pushed a strand of blonde hair behind her ears.

“That’s hardly appropriate.” 

“Listen, to me very carefully. I could have reported you that day you accidentally brushed your hand over my ass. Or the day you touched my actual package and I still could. I know you want this. Go unlock Sebastian’s office door, get on your knees and wait for me.”

She reached for her keys. She’d get a slap on the wrist and maybe have to watch a training video if he turned her in, but sex with Brendan she’d been thinking about it for a while. She went to the office and waited. 

He walked into the office and stopped in front of her. “I want to be perfectly clear. You are to call me sir. I will call you slut or whore or anything that pleases me. You are not to ask questions and you are to do as your told. If you displease me, you will be punished. Do you understand?” 

“Yes sir,” she found the words coming out before she could stop them. 

“Good, come here.” She crawled over to him wrapped her lips around his fat cock. He pulled away and slapped her in the face. “You don’t deserve my cock. Not yet my little slut. Just look at it admire it.” She pulled back looking at his nine inch thick cock. She didn’t know if she’d be able to take it all if he ever let her that is. “Good girl, now give it a kiss.” He slapped her again. “Look me in the eyes while you do it. Good girl.” She kissed his cock and balls all over. She was a bit embarrassed by how much control he had over her. “That’s enough for now slut. Strip and bend over the desk,” he said putting his cock away zipping up his pants.

“But why sir?” she asked. It was a mistake. He ripped open her blouse reached inside her bra twisting her nipples cruelly. 

“Don’t ever question me. Whores like you do as they’re told.” She quickly stripped out of her work attire and bent over the desk. 

“I was going to start with fifty swats but you had to be a disobedient little bitch. I’ll make it seventy-five, on each cheek of course." He smiled cheekily. He started spanking her lightly at first building as each smack landed more powerful than the next.

Alana was squirming by the end her cheeks were nice and rosy. She had tears in her eyes, but her pussy was surprisingly wet. She couldn’t believe she was letting this happen. He reached his hand down to play with her pussy rubbing her clit. “You are so wet,” he whispered in her ear sending shivers down her spine.

“Do you want more slut?” She moaned loudly. It was not the response he was looking for because he took his hand away and spanked her ass for a good minute. “I asked you a question. Do you want more slut?”

"Yes sir.” 

“Good girl,” he continued to rub her clit, before grabbing her hair and pushing her to the floor. He put his foot out in front of her. “Polish my boot with your pussy. Get yourself off. Go on hump my boot.”

Surely this was too much. He couldn’t actually expect her to do something so depraved. “Sir, please. I can’t.”

He grabbed her hair yanking her off the floor. He grabbed a ruler from the desk drawer. “Push your tits out so I can properly punish them.”

She complied because she really had brought this upon herself. He told her the rules. Whores listen and don’t ask questions. He spanked her breasts all over before hitting her square in the nipple twenty times. He did the same to her other breast before placing binder clips on her sore nipples. She screamed at that tears prickling her eyes. He wiped them away gently.

“I’m sorry, I don’t like to punish you. I want the pain to feel good. Are you gonna be a good whore and hump my boot?” She nodded sliding to the floor and rubbing her pussy along his shoe. “Faster slut. Get into it. Look at me.” She was so embarrassed and her nipples ached with every move she made, but then an orgasm began to build. “Don’t cum unless I say so.”

She was so fucking close. “Sir, sir please.”

He kicked her off of him with a resounding no. She cried again this time out of frustration. He helped her up off of the floor. He removed the binder clips rubbed and pinched her nipples before picking up the ruler and giving each nipple five hits. This time it felt good and she wanted to take more for him. Alana decided that she just didn’t like being in trouble. He bent her over the desk again.

“This ass needs to be much redder for what’s about to come.” He gave her over hundred smacks with the ruler. She remained in position like a good bitch. When he finished he stepped back to admire his handy work. He then ordered her to her knees. “You have finally earned my cock. Come kiss it. Worship it.” She did rubbing it all over her face careful not to use her hands. He turned around and bent over. “Get that tongue in my ass.” She blushed but complied. He spread open his cheeks and she hungryily ate his ass. The humiliation was not lost on her, but she craved it. He turned back around gesturing for her to open her mouth. She obeyed.

His dick was huge. It seemed to have grown another inch in size. “I suggest you get it very wet, because it is going in your ass.”

She’d had anal sex before with Pete, but only on special occasions like his birthday and the occasional holiday. One of her boyfriends in college was into anal but his dick was about half the size.

“Don’t worry, I am not going to hurt you, that much.” Then he shoved his dick in her mouth and fucked her face furiously. She chocked and gagged, but the fucking continued. He laid her on the desk her head draped over to better open her throat. He deapthroated her holding her head in place. Her eyes watered from the size and hearth of him. 

He picked her up and kissed her sliding his tongue along hers. It felt so intimate. She felt so owned and she knew she would never be able to settle with Pete. He bent her over the desk fingered and smacked her already red ass until she was ready for him. He had some lube with him as though he had been preparing for this and used a small amount as to make the fucking painful yet pleasurable. He worked himself in slowly at first, before ramming up to the hilt. She screamed out. He picked up his pace ramming into her again and again. 

“Where’s my cock?” 

“It’s in my ah ah... Ow. It’s in my ass, SIR!” she cried out. The door creaked open.

“Good job slave boy. You may have what it takes to be a top at this company yet.” Alana would recognize that voice anywhere it was her boss Sebastian Blade.