Boss's Rules

*****This is my first try at writing erotica. I would love constructive criticism and anything else I should change or improve. Also, let me know if you would like a continuation of the story. I think Anna and Brian haven't had a full scene yet. Thanks! And enjoy! *****

*****

"ANNA!!" barked the harsh voice from the door.

Anna jerked away from where she was bending over to retrieve some papers from the bottom drawer of her desk.

"Oh! Mr. Davenport. I...I didn't know you were coming in early today." she stuttered guiltily.

Instead of answering he stared at her with unnerving intensity causing her to shuffle her feet and fidget with her hands.

She knew she was in trouble now because she hadn't followed the rules. She tried to think of something to say, to explain.

"Maybe he won't be too displeased because my shift doesn't start for another 5 minutes." she thought to herself nervously. She looked at his face but was unable to meet his gaze. Her boss, Brian Davenport was a very attractive man with black hair and piercing blue eyes that could stare through you until you felt like he knew your every secret. She had been working for him just over a month and in that time she had gotten to know that he was very stern and hated it when his rules were broken. He made sure the mistake was never repeated.

Brian leaned against the doorjamb and stared at his secretary while she fidgeted in place and couldn't meet his gaze. He saw that she was wearing non-work issue clothing because she wore a black silk shirt and a tight black skirt reaching 2 inches above her knees. On her feet were black 4 inch high heels. He could see that she had black stockings on under her skirt.

Anna was an attractive young woman with brown hair and wide chocolate brown eyes who had been working for him around a month and in that time he thought he had taught her to heed his rules and not break them.

Truthfully he had hired her because she was so shy and he knew he could turn her into just the kind of secretary he needed. Not to mention she was a knockout with 34C tits and a gently curving figure. But her best feature by far was her bubble butt. Definitely perky. "Guess I'll have to teach her another lesson" he thought with amusement without letting any of it show on his face.

"What is the first rule of this office?" he asked coldly.

She visibly paled and stuttered "A...appropriate clothing must be worn at all times to make a good first impression."

"And are you wearing appropriate clothing Anna?"

"N...no sir."

"And what happens when Anna breaks the rules?" he asked as he stepped away from the door and stepped toward her.

"S..she gets a punishment sir?" she answered nervously while looking at the floor.

"Yes. Anna gets a punishment. But before we take care of that, let's get you into your work uniform. Take off these clothes please." Brian said coming to a stop behind her knowing full well he was crowding her.

"B...Bu...But sir... I can go into the rest room and change."

"No. that will take too long. And since you cant follow my simple office rules, it seems I'll have to help you. Now enough procrastinating. Clothes off. Now."

She raised trembling hands to the buttons of her shirt and started unbuttoning it. As she got to the last button, she hesitated taking off her shirt.

"Anna. We've gone over this a million times in the last month, if you don't want this job, you're free to leave. But if you stay, you must follow my rules or be punished. Now hurry up and make your choice. I have a meeting in my office in 45 minutes." he stepped away from her and went around the desk to sit in the guest chair in front of Anna's desk.

She bit her lip nervously and took off her shirt. Underneath she was wearing a harness of sorts. The leather bra supported her breasts and kept them in place but lacked cups so her baby pink nipples were completely visible through it. As the cold air of the room touched her nipples, they tightened becoming hard little berries.

"Ah, at least you are wearing your work shirt." he said as he leisurely crossed his legs. "now the skirt. Lets leave the stockings and the heels for today. I like the look of them."

Her skirt had a horizontal zipper near the top of her thigh. She grasped the tab and started unzipping. The bottom of the skirt came away from the band around her hips. The bottom of the skirt fell to the floor. Now it looked as though she had a tiny tube around her hips that barely covered her pussy and ass. And Anna knew, as soon as she sat down, her pussy would be completely visible because she wasn't allowed to wear any panties in the office.

"Good girl. I would have had to add another punishment if you were wearing panties. Now I want to make sure your pussy is perfectly smooth. Time for an inspection. Stand in front of me and put your leg on the back of my chair." he ordered.

She couldn't believe he was making her do that. An inspection? He had never done that before.

"I...I... But Brian.."she stuttered.

"Excuse me?" he straightened in his chair. "What is the second rule of this office, slut?" he barked.

"I'm sorry sir. Please forgive me. I didn't mean to call you by your name.." she answered quickly. She felt tears gathering in her eyes.

"What is the rule whore?" he asked coldly.

"I must always call you Sir or Master under all circumstances or suffer severe punishment." she whispered, a tear trailing down her cheek.

"You broke another rule bitch. You'll be punished for that. Get me the wooden ruler from your desk. Oh, and the tri-clamp chain." he ordered.

She turned quickly and got the items from her desk drawer knowing she would be punished more severely if she didn't hurry.

"Now put your leg on the back of my chair. And hurry up. I don't have time for your shit today." he ordered impatiently.

She stood in front of him between his spread legs and hesitantly lifted her right leg and raised it over his shoulder to place it on the chair at his back. She could feel her face heating as she was completely opened to his view.

Brain looked directly at the pussy in front of him and saw that Anna wobbled on her lone heel as she tried to maintain her balance. He loved it when she tried to please him like this. He knew she was extremely submissive. And wouldn't leave him no matter how much he humiliated her.

"That's a pretty pink pussy slut. And looks like you're loving this because you're already wet." he smirked raising his hand and running 2 fingers lightly over her pussy lips to feel if she kept herself smooth like he ordered and to gather the juices accumulating there. He lifted his wet fingers to her lips

"Clean them off." he said. She parted her lips and accepted his fingers into her mouth and licked them clean.

"Feels like you shaved slut. You like pleasing me don't you? You can't help but want this can you?" he cooed to her condescendingly.

"Yes, sir." she mumbled around his fingers.

He pulled out his fingers from her mouth and reached over to grab the ruler from the desk where she had placed it earlier.

"Too bad you didn't follow the rules slut. Now i have to beat your pussy to make sure you don't forget them again." he said.

He used two fingers on his left hand to spread her pussy lips further and lifted the ruler in his right hand. He could feel her wobbling on her heel.

"Stand still slut. Or we'll have to start all over again." he said, taking aim at her clit and pink pussy below. "I think 30 hits today for your transgressions will be enough for you to remember to address me properly and be in your office uniform as soon as you get to the office no matter what time your shift starts or if I am in or not. Any time you are here, your tits and pussy must be naked. Remember that. Now, you will count each strike and thank me for each one."

He felt her tense and waited until she relaxed a little and snapped the ruler forward hitting her directly on her clit.

"Ahhhh... Master." she squeaked.

"Don't forget to count and thank me or that one doesn't count." he said.

"One. Thank you sir. May I have another." she snuffled.

"Good slut." he smirked and snapped the ruler forward again.

"Ahhhhh." she cried. "Two sir. Thank you. May I have another?"

Snap. "EEEEEEEEeeee. Three. Sir. May I have another, thank you?"

Snap... " Four sir...Thank you... May I have another." At this point she began crying as the pain in her clit and pussy increased.

Snap.

Snap.

...

"Thirty. Sir. Thank. You." She cried helplessly now. Her tears wetting her cheeks before falling on her tits. Her sobs causing her tits to jiggle with each forceful breath. Brian quite enjoyed the show and by now had a hard on in his pants just waiting for her to suck.

Her pussy was now quite red and swollen, her clit standing up straight and engorged peeking out of its hood. Her thighs were wet with her juices.

"I knew you were such a whore. Look at you. Enjoying your punishment like a slut." he tsked snidely. "Now slut, quit your whining and hand me the clover clamp chain." he ordered.

She sniffled and leaned over to retrieve the chain from the desk. She hesitantly handed it over to him knowing her punishment was not yet over.

"These clamps are going on your nipples and your clit slut. Your clit is sufficiently hard, get your nipples ready for it. I want you to pinch both your nipples as hard as you can. And if you don't do it hard enough, I will do it for you, and trust me, I'll do it much more painfully so I suggest you pinch them as hard as possible." he ordered as her opened the clit end of the chain and brought it up to her engorged clit.

He brought his thumb to her clit and began to rub it slowly at first, then faster as her breathing picked up. He saw her bring up her hander and begin to pinch her nipples.

"Harder bitch. Much harder than that." he said as he continued rubbing her clit to engorge her clit further.

She pinched her nipples until her fingertips turned white and winced. "Yes like that. Again." He ordered. "Keep going."

He kept rubbing her clit and saw her hips start to rock forward. She kept pinching her nipples hard. Her lips parted, she tipped her head back and closed her eyes.

"Don't you dare sum, bitch. You don't have permission." he barked as he continued to rub her clit viciously.

Her head tipped forward and through hazy eyes she asked desperately, "Please, sir. Please, may I cum?"

"Are you close?" he asked continuing to rub.

"Yes." she panted. "Please. Master." rocking her hips forward faster now.

He continued to rub, just as her orgasm approached, he stopped rubbing and snapped the clover clamp on her clit.

Her eyes snapped wide at the vicious pain and her lips parted. For a moment no sound emerged. Then a pain filled screech filled the air. She automatically jerked her hands from her nipples and tried to move them to take off the clamp on her clit. Brain caught her hands in his. "Don't you dare touch that clit bitch. Get your fingers back on your nipples. They better be fucking hard for these clamps." he ordered as he pushed her leg back to the ground. Anna's fingers immediately returned to her nipples and pinched them very hard. She winced again and began to cry again from the pain in her nipples as well as her clit. After a few moments of this, he pushed his chair back and stood up.

"You're not doing it hard enough slut." he said as he knocked her hands aside. "This is a punishment, not you trying to turn yourself on."

She sniffled, looked at the floor and said "I'm sorry sir."

"Hm.. " he said as he grasped her nipples between his index finger and thumb and pinched as hard as possible and pulled her nipples away from her tit. "There we go. We want these babies to be hard little cherries." he said as he pinched and pulled on her nipples.

"Ahhhhhhh." She winced and stood on her tip-toes to try stop him from pulling her nipples too hard.

"Get those heels back on the ground!" he barked as he grabbed her nipples between his nails and pinched hard.

"EEEEEEEeeeeee. Oh sir. That hurts!" she cried.

"There. They're ready for the clamps." he said ignoring her tears. He reached down and grabbed the chain from where it was dangling from her clit.

In the pain from from her nipples, she had forgotten about the pain in her clit but it burst forth again when he jerked the chain up and tightened the clamp on her clit.

He found the other 2 clamps on the chain and brought them up to her nipples. He opened the clamps and put them over her nipples.

"Look at me." he ordered. "And don't you make a sound." he said as he snapped the clamps shut.

She kept looking up at his eyes and didn't make a sound as the pain in her nipples made her want to scream. More tears flooded her eyes. She looked down at her nipples crushed int he clover clamps and saw that the chain was just slightly too short. It tugged her nipples down and her clit up. Just as Brian had planned.

"Oh, almost forgot." He said as he moved away from her to walk to her desk drawer and pull out a 6 inch butt plug. "Lets not forget about this." he said as he walked back and stood behind her.

"I dont think you deserve lube but I'm not cruel so i will allow you to suck on it for 10 seconds so I suggest you stop crying and get this as wet as possible or its going into your asshole dry." he said as he brought the red buttplug to her mouth.

Anna knew he was serious and immediately parted her lips and swallowed the plug. She began to suck on it as he moved it in and out of her mouth. He pushed it to the back of her mouth and caused her to choke on it as it entered her throat. He chuckled as he pulled it back out only to push it back into her throat, causing her to choke again. "Learn to swallow around it slut." he said. "Anyway. your 10 seconds are up. Turn around and bend over your desk. And make sure those nipples touch the desk." he said.

She slowly turned and winced as the movement pulled on the clamps. She stepped towards the desk and bent over it, resting first her nipples then her tits on the desk. She winced in pain because the cold desk caused her nipples to tighten and the weight of her tits caused the clamps to crush her nipples.

"Such a pretty butt slut." he murmured as he smacked her ass once. Twice. Taking a hand he placed it on her asscheek and roughly pulled, parting her asscheeks to reveal her pink little hole. "Look at this shy little star." he cooed as he brushed her asshole with the dildo. The large red dildo looked obscene against the innocent looking star and her alabaster skin.

"Clench that ass bitch. I want this dildo to hurt going in." he ordered.

Anna hung her head knowing this would be painful but knowing there wasn't anything she could do. This was the selected punishment for her transgressions.

When he felt her clench her butt, Brain rested the dildo at her asshole and began to push against her star. The resistance held the dildo back but her little asshole was nothing compared to the brute force of Brian's push. At last, the little ring gave up, and with a screech of pain from Anna, the dildo entered her asshole and swiftly pushed into her rectum earning a grunt from Anna.

When all 6 inches of the dildo were seated inside her ass, Brian stood back and admired how the red looked against her skin. He saw the juices spilling from her wet pussy below as well.

"Looks like you are enjoying this too much slut. Way too much. Now it's my turn." he said as he smacked her ass hard. He grasped her arm and pulled her up and turned her toward him.

"Now slut, get on your knees and open up my pants. You're going to suck my cock before I get to the rest of your punishment." he ordered as he put his hands to her shoulders, turned her around and pushed her to the ground.

She fell to her knees and winced as the sudden movement pulled on her nipples and clit and further inflamed the pain.

She looked up at him and saw he was impatiently waiting for her to get his cock out. She blushed and looked down at his zipper to see his hard cock pushing insistently at the zipper. She hesitantly reached up and pulled down his zipper causing his 8-incher to pop out and almost smack he in her face. She jerked back a bit but felt his hand come to the back of her head and push her face insistently toward his cock.

To be continued...