Controlling Young , Naughty Olivia

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Author’s Note: This is my first submission to Literotica. I would greatly appreciate any feedback, especially voting. Writing this story was very much arousing and I hope that reading it gives you the same pleasure.


At first, she was afraid he might be firing her for unprofessional conduct. But then he stepped closer and she realized she may finally be getting what she wanted.

Olivia Zerter sighed as she gathered up the day’s paperwork and put it in a stack. It was 10:30 on a Friday night and she was exhausted. She had been working at this job for a little over a month and 9pm was the earliest she had ever left the office. When she had first been hired, she was ecstatic. She was the executive assistant to the CEO of a large multinational company. She knew that this would be an excellent first step climbing the corporate ladder.

When she first met Ethan Rowe, she was in awe. He was in his early forties with dark brown hair and bright blue eyes. He was always immaculately dressed and had worked extremely hard to reach his position. She had been told at the beginning that the job required long hours. She figured that meant long hours with her gorgeous boss and maybe the odd steamy night. Unfortunately, she had been poorly misguided.

At first, she wore short skirts and blouses dangerously unbuttoned. Her boss hadn’t noticed at all. He barely spared her a glance as he asked her to grab him a coffee or bring him a file. It was very frustrating. She knew she was an attractive 22 year old with sexy auburn hair and hazel eyes. She was proud of her long, toned legs and flat stomach, courtesy of a 45-min run every morning before work. Her C-cup breasts were courtesy of good genes.

Today, she was wearing a short black skirt that barely made it past her firm butt. Her white blouse was slightly undone to reveal bits of the black lace bra that matched the tiny thong she was wearing. Although she had pretty much given up all hope that her boss would notice her, she pushed up her bra, straightened her hair and added a little lip gloss before she went to say goodnight. She knocked at his office door and opened it slowly. He was furiously typing at his computer, tie and blazer tossed on the couch, sleeves rolled up. He didn’t even look up as she walked in.

“I have some files for you, sir.”

He spared her a brief glance as he said, “Ah yes, Olivia. Thank you.”

She couldn’t help but notice how sexy his voice sounded and how the muscles of his forearm stood out as he typed. He had such manly hands and long fingers. For a second, she imagined those fingers inside her, bringing her pleasure. She felt a slight stirring between her legs and decided to leave before he made her any hotter.

“You’re welcome, sir. I’ll be leaving now. Is there anything else I can do for you?” She couldn’t help but feel hopeful that maybe, just maybe, tonight he’d ask her to stay.

He looked up at her, removing his reading glasses. He then pushed his chair back and got up, walking towards her. Her legs felt weak küçükçekmece escort and her panties were getting wet.

“I didn’t realize you were still here. It’s quite late. A young girl like you should be out on a Friday night.”

She couldn’t stand it anymore. She squeezed her knees together and thought of the least sexy thing she could imagine.

“Oh…Well…umm…Work comes first, of course.”

He smiled and nodded.

“That’s very admirable, Olivia. That’s precisely the attitude that will get you ahead in life. Your efforts don’t go unnoticed. I hope you realize that. I notice that you stay later than the others and are always prepared and alert. You have been working here for about a month now?”

“Yes, sir.” He chuckled.

“I think we can do without the ‘sir’. Please call me Ethan.”

“Yes, sir. I mean, Ethan.” She gave a nervous laugh. He nodded his approval.

“Please have a seat.” He walked over to where she sat and leaned back against the front of his desk, crossing his arms.

“Are you enjoying working here, Olivia?”


For the first time, his eyes swept over her body and lingered on her bare legs. She crossed them nervously, her skirt riding up even further. She couldn’t help but take a peek at his crotch and was surprised to see a very slight bulge.

“You’ve done quite well here. Quite well indeed.” He was so confident and self-assured. Her thong was thoroughly soaked at this point. He eyed her brazenly, taking in her slightly unbuttoned blouse, her short skirt and her incredibly high heels. She shifted nervously.

“Don’t think that I haven’t noticed you, Olivia. The way you toss your hair when I come near. The way you cross your legs to allow your skirt to ride up higher. The way you unbutton your blouse to give me a peak of that glorious cleavage.”

She couldn’t believe what she was hearing. At first, she was afraid he might be firing her for unprofessional conduct. But then he stepped closer and she realized she may finally be getting what she wanted.

“You have been causing me quite a bit of discomfort.” He ran a finger lightly along her bare thigh. She looked up at him, certain that her longing was clear in her eyes. Her legs parted out of their own accord and she leaned back in her chair. His fingers slowly made their way up her inner thigh, brushing against the wetness of her thong.

“I’ve wanted you for quite some time. But I had to be certain you were serious. Both about this job and about me.”

“Of course, Ethan.”

“Now that we’ve established you are, I think we need to issue some ground rules. There are a few basic clothing guidelines I need you to adhere to at all times. Firstly, you will always address me as sir. Secondly, no panties. Ever. Unless, of course, I ask you to wear some. If I catch you wearing a pair without permission, there will be consequences.”

Olivia gulped, unsure of what she was getting herself into.

“Third, küçükyalı escort you are to wear tight skirts that are a minimum of 6 inches above the knee. They should also ride low on your hips. You are also to wear stockings at all times. And lastly, you are to have a minimum of three buttons undone on your blouses at all times. Do I make myself clear?”

“Yes, sir.”

“You are to also make any changes I request to your outfit. I’d like you to fix yourself right now to adhere to these rules. Except of course, the stockings.”

Olivia paused for a second, realizing what he was asking her to do. She got up and reached between her legs, slowly pushing down her tiny black thong with both hands. She stepped out of it and set it on her boss’ desk. He picked it up, brought it to his nose and inhaled deeply, closing his eyes. Next, she pushed her skirt down so it exposed some of her midriff and proceeded to roll it so that it became even shorter than it already was. And lastly, she unbuttoned one more button on her blouse, giving him a nice view of her lacy bra and plenty of cleavage.

“Excellent. You may leave now. Have a nice weekend. I will see you Monday.” Ethan sat back down behind his desk.

“But…,” Olivia stuttered.


“Nothing, sir. Have a good weekend.” Olivia turned away, disheartened at the thought that her only companion tonight would be her toy sitting in her bedside drawer.

“I sense you were expecting more, Olivia? Come here.”

Olivia turned around and walked over to him. He pulled her onto his lap. He slowly traced his finger along her exposed cleavage, giving her goosebumps. His other hand traced small circles on her inner thigh, making Olivia moan.

She spread her legs, needing release. He squeezed her breast in one hand and kissed her, biting her lower lip teasingly.

“Now, I really think you should be getting home, Olivia. Since your apartment is on my way, why don’t I drop you off?”

At first Olivia protested, wanting to stay, but after a semi-stern look from Ethan, she relented.

She grabbed her bag and followed her boss. He stood 2 feet away from her in the elevator, arms crossed, just looking at her with his intense gaze. She looked away nervously but was drawn back to his bright blue eyes. She was accustomed to men being unable to keep their hands off her. And now, this man, her boss, barely touched her but had her pussy leaking down her thighs.

Ethan’s private car was awaiting them at the entrance. He gave his driver Olivia’s address, pressed a button to close the dark window between them and settled in comfortably beside her.

He began stroking her bare leg again, massaging her inner thigh in small circles. She reached out tentatively and started rubbing between his legs, noting with pleasure how well he responded to her touch. She then got up so that she was straddling him and leaned in to kiss him. His hands explored her bare legs while his skillful tongue explored her sexy maltepe escort mouth. He squeezed her firm ass in both hands, pulling her close so that her pelvis was now grinding into his. He groaned against her lips as his hands explored under her skirt, feeling for her bare wetness with his fingers.

He began to unbutton the rest of her blouse and ran his hands along her flat stomach and back up to her full breasts. She reached down and unzipped his pants, slowly pulling out his thick erection. She stroked it slowly, lazily and began to guide it into her when the car came to an abrupt stop.

She looked out the window and groaned when she saw her apartment building.

“Come up,” She practically begged.

“Not tonight. Have a good weekend Olivia.” Ethan zipped up his pants and gave her a small kiss.

Olivia walked up the steps to her building, incredibly frustrated, hurt and slightly humiliated. She had handed herself over to him and he hadn’t even wanted to come inside to finish what they had started.

The second Olivia walked through her door she ripped off the rest of her clothes and started a warm bath. She grabbed her latest edition of Cosmopolitan, a glass of red wine and of course, her reliable bedside toy.

Unbeknownst to her, someone was waiting in the dark in the building next door. He had a clear view into both her bedroom and bathroom and had on more than one occasion watched her. She hardly ever closed the blinds, giving him plenty of opportunities to watch her change, shower and of course, masturbate. He watched as she slipped off her bathrobe and admired herself in the mirror. She squeezed both nipples until they were hard as rock. Satisfied with herself for the time being, she stepped into the bathtub and allowed herself to relax. She closed her eyes and let her hands roam her young body, remembering how Ethan had done so just moments before. Why wouldn’t he come up? He was clearly aroused.

She squeezed both breasts in her hands; squeezing until they started to hurt. She dangled one leg over the edge of the tub, making the water trickle down her painted-red toes onto the tile below. One hand reached down to rub her smooth, hard pearl while the other reached for her thick, 8-inch dildo.

Olivia licked the tip, imagining it was Ethan’s dick instead. She then started to suck on it, taking it as deep as she could. Since she bought the toy a few weeks ago, she had been practicing deep throating it in the hopes that she would get the opportunity to do the same to Ethan’s cock. She then slid it down her torso to the juicy folds of her pussy. She closed her eyes and began to insert her toy back and forth, slowly at first and then faster. Her breathing escalated and her moans became louder and louder. She squeezed her left breast hard as she came. As her orgasm subsided, she pulled out her smooth black friend and licked her juices off it, smiling to herself.

She was drying herself off with a towel when she felt a light breeze. She realized that she had forgotten to close the window and blinds which had a direct view into her shower and bathtub. She walked naked to the window to close it. Olivia looked out and didn’t see anyone, so she shrugged to herself and decided to leave the blinds open. She didn’t see the man watching her closely, camera next to him, seeming as though he had been pleasuring himself while watching her.

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