Emily's First Job Ch. 04

Once they arrived back at Ms. Sinclair's house, Joan quickly exited the car and snapped her fingers for Emily to do the same. Eager to please, Emily opened the door, got on all fours, and quickly tried to keep pace with Joan. The plug in her ass was driving her crazy, and she was starting to get sore. She would both moan and wince each time she moved.

Smirking down at her, Joan ordered Emily to open her mouth. Emily did as she was instructed, and the handles from the bag from the lingerie store was put in her mouth. Joan turned and began to walk toward the door to the house. Emily tried to keep up and not stumble over the bag.

Joan did not turn to look at Emily as she strolled through the house. Emily did her best to keep up. Joan sat in a high wing backed chair in the den of the home. Emily sat back on her heels with her legs spread as wide as she could make them and winced as the plug nestled itself inside her.

"Get in proper attire."

Slowly, Emily peeled the tiny dress from her body. She folded it neatly and tucked it under the coffee table with the bag from the store. She resumed her strained pose and whined as the plug moved again.

"Present your bottom to me."

Turning crimson, Emily got on all fours, turned and put her chest to the carpeted floor. She turned her head, arched her back, spread her thighs, and pushed her ass high in the air. The plug moved within her and Emily ached.

Joan's fingers traced Emily's tight anal ring that was holding the plug inside her. Joan tugged slightly at the plug pulling it a few centimeters out and Emily groaned. She felt her pussy lips begin to swell and become slick with arousal.

"Such a wet little whore. Any time I touch you and your cunt drips."

Using one hand to tug the plug half way out and then force it back into Emily's sore rosebud, Joan used the other hand to stroke Emily's quickly slickening sex. Emily groaned and moaned the pain from the plug stretching her anal ring and the pleasure from her sensitive sex was conflicting and Emily's body could barely keep up. The heat she felt started in her sex and radiated throughout her body.

With a pop, and a loud grunt from Emily, she felt the plug pulled entirely from her ass. Joan giggled and soon a cool gel was squirted into her. Emily moaned and she felt Joan slip two fingers into her. Joan pumped them in and out and the feeling was similar to that of having to move her bowels however, Emily felt every muscle in her body respond and her head began to swim.

Emily's pussy twitched as two fingers slide into her channel, and the fingers in her asshole slipped out. As the fingers inside her pussy slipped out two fingers buried themselves deep within her asshole. Emily groaned each time and felt her body tremble. She was so turned on.

"This is going to be our first focus of your training. You are going to surrender your ass to my will. Do you understand?"

In a trembling voice Emily responded: "Yes Ms. Sinclair."

Joan laughed, and Emily felt her entire body blush. She had never had her ass fucked or filled before Ms. Sinclair. The feeling was so humbling. Emily felt that it both aroused her and embarrassed her. She felt dirty as Joan worked a third finger into each of her holes.

Emily's groans began to get louder and her pussy clenched harder around the fingers. She was Joan's whore, no matter what she had to do what Joan said. No matter how dirty or embarrassed she felt. Joan had bought her.

"We are going to make this gape. So there will be no denying that you are a whore Emily."

Emily whined, both in arousal and in a pang of humiliation. Her body blushed again. This was becoming a common thing with Joan. It was like every time she said something to Emily, or told Emily what she was going to do, Emily got both aroused and humiliated.

Her ass felt full and sore as Joan worked her pinkie inside Emily. Emily couldn't help but push back against Joan's fingers. She was a whore; she was going to be the best whore she could be. It would make Joan, her boss happy. She had to do it.

"You are a natural. You are opening already. It is really lovely. You're going to be a good whore and learn to take a fist. Do you understand Emily?"

Again, her voice trembled in response: "Yes Ms. Sinclair."

Emily whimpered in pain as Joan forcefully shoved four of her fingers inside Emily. Her thumb pressed into her pussy. Keeping the four fingers in her asshole, Joan tried to open them while simultaneously working three fingers and a thumb into Emily's pussy.

The feeling of absolutely fullness overcame Emily. She clawed and grabbed at the carpet. Her body trembled. Her clit pulsed. She whined and whimpered while Joan continued to work her body.

"You belong to me Emily. This body of yours, its mine. I can do what I want with it, to it, and I can fill it with whatever I want."

Emily nodded and a tear slid down her face. Her asshole was on fire and the pain was increasing. Emily was afraid she was going to tear right there. If her body could not do what Joan wanted, then what would happen?

"We will work your ass nightly little dumb whore. We will stretch it wider and wider each night. You will wear plugs every day. I will fist you by the end of the week you little whore. Then we will work to make it bigger and bigger!"

Joan's laugh cut through Emily. She whined as Emily spread her fingers against Emily's tight anal walls. Emily could feel her body straining to obey. The tears falling down her face continued. There was nothing she could do but obey.

Suddenly, a sloppy squish noise filled Emily's ears and she felt empty. Her anus felt stretched and her pussy clenched at nothing. There was a slime feeling being wiped on each of her ass cheeks. Joan was wiping her fingers off on Emily.

To Emily's dismay, she found that she was torn between being relieved that her ass was empty and disappointed that her ass was empty. She fought the urge to wiggle her ass and entice Joan into filling her again.

The fiery sting and cracking noise caused Emily to howl and jump. Instinctively, Emily brought her hand to her right ass cheek, where the sting oriented and another sting landed on her left, harsher, deeper, and Emily screamed again.

"You embarrassed me you stupid worthless cunt. You are being punished. Do not cover that ass I own. It is mine to discipline. It is mine to whip."

Emily cried as each welt formed instantly. She felt a slight bit of blood trickling down her thighs as the pain was excruciating. She was being whipped with a single tail harshly. Every time the whip kissed her ass, Emily fought the urge to cover and run.

"You will do what I say without question slut. Do you hear me?"

"Yes Ms. Sinclair." Emily cried.

Another crack of the whip sent pain rippling through Emily's body.

"You are to be my obedient little fuck toy."

Her skin split and Emily screamed louder than she had before with that lashing.

"Tell me what you are."

"Your obedient fuck toy, Ms. Sinclair."

"You are so fucking stupid, is this the only way to get through to you?"

The crack of the whip, the pain rocketing through her, Emily didn't know the answer. She just screamed and cried.

"Answer me you useless fucking cunt."

"I don't know Ms. Sinclair. Please. I will be obedient. I promise Ms. Sinclair. I promise."

Twenty. She was given twenty total lashes with the whip. Ten lashes for each ass cheek.

Joan snapped her fingers "Up on all fours."

Trembling, Emily raised her chest, sobbing her wobbling arms held her up. Her ass felt like hamburger meat.

Through blurred vision, Emily saw the blunted woven leather end of the whip in front of her face. It was held in Joan's hand.

"Kiss the whip and thank it for punishing you."

Emily whined it was so embarrassing to address an inanimate object. Slowly, she pursed her lips; afraid to feel the pain again she pressed her lips against the whip.

"Thank you whip for punishing me."

Joan pointed her stiletto'ed heel under Emily's chin. "Now kiss my foot and thank me for the honor of feeling my whip across that worthless ass of yours."

Emily lowered her body gain and kissed the leather tip of Joan's heel. Whispering she did as she was instructed: "Thank you Ms. Sinclair for the honor of feeling your whip across my ass."

"What kind of ass?"

Joan cracked the whip but not against Emily's skin. Just the sound caused Emily to recoil and wince.

"I'm sorry Ms. Sinclair, I'm sorry. Thank you for the honor of feeling your whip across my worthless ass Ms. Sinclair."

"It truly is an honor to be punished by me Emily. I do this to make you the best whore you can be. It seems you are too dumb to listen at times, so I have to resort to pain to ensure you don't do things again."

Emily whimpered in response. The tears were beginning to slow but the pain radiating from her ass was continuing.

Joan disappeared from in front of her and Emily heard her take a seat behind her in the chair again. Emily was trembling and yelped when the salve was applied to her striped ass. Joan worked a cool healing gel into her new wounds. Then Joan told Emily that it was time for bed.

Once on her pillow, Joan gave Emily a list of explicit instructions that she was to do in the morning. Emily was to gently wake Joan in the morning. Emily was so tired she could barely focus on what Joan was telling her. She hoped she got everything before she drifted off to sleep. She didn't want to be punished again.