Personal Assistant

Curled under his sheets, his hand instinctively reached for his shaft as he thought about that night's date. Just an hour before his face was planted deeply between the soft cheeks of Cheryl's ass licking away eagerly. He was shocked to discover how much happiness he had gotten from this one slight act. Just the touch of his lips to her soft crack brought him a rush of warmth he had never before felt. This act that a week ago he would have thought of as vile and humiliating now dominated his thoughts. Funny thing was, he didn't mind it at all. In fact, he couldn't wait until he saw her again and hopefully she allowed his head in her ass once more. Surely they would see each other,they both enjoyed the evening though she had said nothing about another date. As if on cue, the phone rang.

Breathing heavily, he picked it up to hear her voice, "Heath, I don't want you to masturbate."

How did she know? "I wasn't, I- I mean I won't," he lied, cursing himself for doing so.

She almost laughed on the other end. "Good. Just make sure you don't. I want you to be fresh for our date on Friday."

This time she did laugh when he was unable to hide his excitement by responding quickly, "Great! I was hoping to see you again."

"Oh you will. I wouldn't give up someone like you. You know how to make me happy and that's important."

Her voice was soft now and Heath found himself growing close to her as he remembered what they shared together.

"Remember," she continued, "hands off until Friday!" she laughed and before he could say goodbye he heard a dial tone.

After that sleep didn't come easily. Compounded by the sound of her voice playing over and over in his mind, keeping his hands off himself was more difficult than he'd expected. However, he stayed true to his word and by the time the weekend came it felt as if he'd not come for months. He maintained a state of almost constant arousal and usually managed to hide his obvious erection in the office.

They rarely spoke in that time. In fact, he hardly saw her at all while they were working. She was consumed with her job and he only saw the passing glimpse of her dressed in her power suit, heels and hose when they passed in the halls. Twice he tried to say something but was too shy and could not. Afraid to call attention to their new relationship he didn't push it any further.

She, of course, knew what he was doing. She saw him and knew he watched her whenever he could. His attempts to distract her with a series of childish pssts and whispers were laughable. She next expected him to toss notes on her desk when no one was looking. Let him sweat it out. Let it all build inside him. It's good for the constitution.

Friday night came and he was ready long before he was supposed to meet her. Freshly showered, dressed and prepared, he paced his apartment counting off the minutes. Stopping in front of the full length mirror by the door, he examined himself. Wearing the freshly pressed white button down and black pants just as she requested, he thought he looked like a waiter but knew better than to question her requests. She was out of his league and, though he knew better, he had grown more attached to her than he would have liked. Right now she could suggest a tattoo on his forehead and he'd camp outside the tattoo parlor to be the first one in.

Understandably he was a bit disappointed when he rang her doorbell and was greeted by the sight of her in only a slip talking on the phone as she silently ushered him in. He waited patiently in the corner of the room as she finished her conversation. With the phone nestled in her shoulder she walked to the bathroom and began brushing her hair. The door was left half open so he had a good view of all she did, though she seemed unaware.

Still ensconced in the conversation he watched as she sat on the edge of the tub and began to rub moisturizer up and down her bare thighs. The bathroom door was ajar, allowing him to watch her ever movement. When she bent to examine her lips in the mirror, he saw the bottom heft of her asscheeks. It was then he knew she had forgotten about him and left the door open, unaware of his presence. She made no attempt to get off the phone or even shorten the conversation. Instead she enjoyed herself, talked animatedly and laughing several times. Finally, after a spirited discussion, she walked into the living room. Heath couldn't stop staring at her bare legs, soft and smooth from the shower. The thin material of the slip flowed around her hips as she came to him.

"Am I early?"

Fists against her hips she looked him over, letting him see her gaze roam over his body. "Not at all, I'm just taking my time." Her planned delay in the bathroom worsened his condition, she saw. His erection strained against his black pants. "Is that ok with you?"

"Oh…uh…of course," he smiled, attempting to laugh off his nervousness.

Turning from him she commented, "I see you wore what I told you. Good boy." That's it, she thought, not only get him to follow your orders but make him admit to it.

He jumped at this. "Yeah, I hope you like it" and playfully posed as if he was at a photo shoot. Staring at her ass beneath the silk, he could see she wore nothing underneath. It mesmerized him. Never has he had such a reaction to a woman just because of her ass. He knew he would follow it eagerly wherever it went.

Walking to the bedroom, he followed her as she knew he would. As she sat down at the foot of her bed, she held her arms out behind her, stretching like a cat. He saw the slightest view of light brown hair at the apex of thighs but looked away for fear of being caught. He made to sit across from her.

"Don't." She commanded. He jumped to stand in front of her. "Just let me look at you. Don't move."

His arms hung at his sides. He remained motionless, feeling awkward.

"Nice. Now turn."

Again he followed directions, facing the opposite wall, giving her a view of his backside.

"Remove your shirt."

Without a word of protest he did so. It fell to the floor and she studied the interlocking muscles of his back while he remained turned away, eyes towards the ground.

"Your pants. Take them down."

There was a moment of hesitation with this command and she heard him attempt to speak then quieted, thinking better of it. His hands remained at his belt buckle, pondering his next action. It was inevitable that he would obey and soon his pants fell to the ground. He stepped from them clad only in black cotton boxer briefs. They looked good on him, snug in all the right places to show his best features.

"Turn," she said. Barely a whisper.

He did so, looking down, still unable to meet her gaze.

"Are you nervous?"

He nodded.

"Why?"

He answered with a shrug of his shoulders.

"Heath look at me."

Slowly he raised his face to look.

"Pull them down."

He seemed to whiten slightly at this command but said nothing. As she watched he did as told, putting his fingers in the elastic waistband and slowly drawing them past his hips. He managed to shield his front while he did so, awkwardly covering himself.

She told him to move his hands. When he didn't she repeated the command louder. Meekly his hands moved to his sides, trembling slightly.

It was the first time she had the chance to view him and she took her time. He was long, but not more than she was used to. He was thicker than expected though, and she imagined coiling her hand around his shaft while he moaned in compliance. He looked mortally embarrassed to be so exposed in front of her. Staying still was difficult and he had to clasp his hands behind his back, forcing his member to jut out obscenely.

"Come to me." She barely spoke and he shuffled forward. Still unable to look her in the eyes, he watched his feet lead him to her. When he stood in front of her she reached forward and began stroking beneath his balls ever so slightly. He inhaled quickly and stood rigid. She looked up at him, allowing her breath to be heard. When she held her hand around the thick head of his cock she sighed warmly.

Unconsciously he began to leak. Feeling moisture on her hand she looked down, finding the small spot of pre come in her hand.

"Excited, aren't you?" He nodded quickly. "You didn't let yourself come since our date, did you?"

He shook his head. "Of course not."

"Good boy," she smiled, her hand entwining around his length. She squeezed gently and slid her hand over the knob centered in her fist. As she looked him in the eye, she licked the palm of her other hand and coated his cockhead with her saliva. His knees wobbled and she saw his balls begin to shake. "I know you need it and you really want to come but I don't want you to," she warned him. "If you feel like you can't help yourself I want you to tell me. I'll not have a boy that can't control himself." She placed the flat of her hand against the very tip of his length in a stop motion, eliciting a high pitched gasp from him. "Understand?"

Nodding quickly he gave his assent.

"Very good." She reached between his legs and began rubbing him softly behind his balls while her hand continued to grip his cockhead. With each movement he quaked that much more. Tiny sounds of desperation came from him without restraint, some small breaths of need, others moans of pleading or squeals of reluctant submission.

Holding his balls securely in her palm, she used the index finger of her other hands to slowly trace the ridge of his corona. This is a man's most sensitive spot, exceedingly so for an untrained boy such as he. His mouth dropped open and he cried out from the sensation of release stilled just before its peak. She left him that way to examine his reaction.

His body shook with need, unable to even open his eyes, he was in all ways available to her. One finger traced the underside of his shaft, along his bloated urethra, stretching to accommodate his seed. One hand curled around the base, holding him possessively while keeping his imminent burst at bay.

Then, daintily, almost like a virgin would, she teased the shiny bulb of his cock with a series of touches, squeezes and light, almost nonexistent kisses. As she hoped he shook but she only continued her ministrations.

"Please…please…please…," he begged.

"What is it sweetie?" She stroked the underside of his balls lovingly. "Are you going come?"

"No…yes…please, I need to come."

"You need to come? I don't think you need to do anything but stand still and follow orders," her tone rising a little. "I think you've come way too much for a boy."

As she spoke she pinched his cockhead between her thumb and index finger. With her fingernail she penetrated him slowly in his opened peehole. There was a sound like he had begun to cry and she looked up slowly.

"Does that hurt, sweetie?" He bit his lower lip as if in anguish. "What is it, baby?"

"It tickles. Feels strange…feels good."

Her hand traveled slowly up the length of his shaft until it clasped his head from below. The pad of her thumb stroked the cleft of his crown, teasing him gently. "Can you take it for me?"

As he nodded, eyes closed in a tight squeeze she began to explaining. "I spoke with the top level execs and they all agreed that you're doing fine work. They'd like to increase your duties if the program allowed it but they know you'll be returning to school at the month's end." She squeezed and stroked his length, keeping him at his peak while teasing the tip of his head and rubbing the precome that oozed relentlessly into his warm skin.

At that moment she realized just how much power she had over him. His cock, a man's livelihood, was in her hands at her mercy. He was completely naked and unable to think straight while she enjoyed his state and pushed him further than he'd ever be able to handle. If there was ever a time, this was it.

"So," she continued, squeezing and releasing his dripping cockhead, "I suggested something that would best benefit both of us. You do good work," she tugged on his balls as she said this, "and I could use someone to help me out now and then when I don't have time to do everything I need to."

Shocked by the slow squeezing of his balls, his mind became clear. "What would I do?" Unconsciously he pumped into her hand. "What kind of jobs?"

She seemed intrigued by the motion of her hand on his balls and studied it for a while before answering. "Helping me out, doing things I don't have the patience and time for." Her fingers played along his thickened shaft and he sighed happily as she continued, "Filing at work, keeping my schedule, things around the house, cooking, cleaning, running errands. That type of thing."

He seemed in a spell, his body swaying with the motion of her hand. She repeated her offer of the position and he nodded mindlessly. Seeing this, she released his cock from her grasp. It bounded helplessly, begging for attention and his eyes popped open immediately.

He knew better to question why she let him go but she could see it in his eyes. He had gotten to the state where he would do anything just to continue the pleasure she was giving him. To stop these selfish thoughts and bring his attention back where she thought it belonged she held the thickness of his cockhead between her thumb and index finger, clamping down on it like a vise.

"You'll have a slight pay raise, which is better than just the class credit you're making now. Of course you'll have to take some time off from school, as this is a full time job. Your room and board will be paid for, as will your other needs."

Still she awaited his response. A sharp pinch of his sensitive head encouraged him. "Yes," he choked out breathily, "I'll do it. I'd love to work for you."

She hadn't expected this last part and smiled to herself. "Very well then. We just have to make it official."

She turned and placed her hands on the back of the sofa. Her slip rode up, exposing the swell of her bottom, as well as a wide strip of bare skin. Reaching back, she ceremoniously folded it back to expose her bare ass completely. "You know what to do," she taunted. "Give it a big kiss to show your sincerity. Let me know how much you want to be my personal asskisser."

Dropping to his knees, he felt his breath quicken. He hadn't been able to get their last date out of his head and the time he spent with his lips planted against her ass had been constantly on his mind since they parted. He gazed adoringly at her bare end, thankful to be in such a position again.

With the utmost respect, he leaned forward and placed a kiss reverently on each cheek. Before she directed him, he planted another one on the center of her crack, his tongue sliding past his lips to tickle her sensitive skin. She swooned from his tongue and bent down further to give him better access.

Emboldened by her actions, he focused on the swell of her pussy, covered in a soft puff of hair. The tiny slit of her pussy opened slightly, exposing a dab of moisture. Closing his eyes, his lips touched her dampened sex, showing the respect she demanded.

When he finished she stood up and pulled the thin material up over her head and to the ground beside him. On his knees, he looked up at her naked body, the first time he'd ever been allowed to see it. She was beautiful, better than any fantasy he'd ever conjured up. Her skin was alabaster and bare of any imperfections, smooth as ivory, it went well with the auburn of her pubes. Her hips were round and womanly, not heavy as would be expected at her age, but strong and muscular. He could see she spent a lot of time keeping herself in shape.

She didn't face him but turned to the bedroom and walked away without a word. When she reached the doorway, she slapped her hand on her thigh in a ‘come here' gesture. Instinctively he followed, first on all fours, then caught himself and rose slowly. His knees were sore and legs cramped from spending too much time in that position. Finding it easy to shuffle behind her on his knees he did so, scurrying behind each step she took.

Folding back the coverlet of her king sized bed, her nude body seemed to meld perfectly into her bed. She turned the lights out, leaving him in blackness. Hearing him in the dark she advised him to lay down and sleep. There was a big day ahead for them, she said. He made his way to the other side but she scolded him, telling him to lay at the foot of the bed where he belongs. Weary after the long day, and not wanting to upset her further, he did as instructed and rested below the end of the bed, naked and curled into the fetal position.

The next morning he was awakened by the sound of her shower. Stiff from the floor, he slowly sat up and made his way to the bathroom. Her naked profile was visible through the clouded curtain, making his morning erection even harder. His hand reached out to pull back the curtain, excited to see her naked body once again, but was instead met with a stinging slap across the cheek, spraying droplets of water around the room.

"If I can't be afforded even the most expected privacy then I have to question your ability for this job," she chastised him. He kept his eyes to the ground after feeling the impact of her hand. When she stepped out he was gazing at her feet.

Handing him a towel she insisted her dry her off and bent forward, spreading her legs just so. He worked his way up her legs, softly patting down her freshly shaven skin. She was soon dried and Heath stood up, running the towel between the tight crack of her bottom as a finish. Pulling the towel from his hands, she patted at the spots he missed and began choosing clothes for the day ahead.

"I have an interview with a law firm today. You will be coming with me."

He agreed, explaining that he had to return home and put on a suit, as his clothes, now in a pile by the front door, weren't suitable for what she had planned.

"That won't be necessary," she insisted, pointing at the suit of clothes that lay on the bed. Looking at the boxer briefs and tight t shirt that lay there, he asked about the rest but she only chuckled. "That's it. That's all you'll need."

Knowing better than to argue, he slipped into the boxers, finding them uncomfortably tight. His erection, present since the night before, was obvious beneath the white cotton and he blushed when he realized what she had in mind.

She drove shotgun, comfortable as she easily sped through the intersection, her hand on the stick shifting gears intermittently. Easing the car into the only available spot, she quickly stepped out, expecting him to follow. He hustled to catch up with her, his attention captured by the sway of her ass beneath the tight business skirt she wore for the occasion.

When he passed through the revolving door and through the marbled lobby she was already speaking to the front desk. Feeling out of place in his revealing attire, he did his best to look inconspicuous. The austere woman at the front desk looked him up and down, letting her glance linger on the slowly receding bulge of his crotch.

Cheryl turned to face him, her arms crossed. "Ready to put on a good image for Ms. Sims?"

He replied he was ready and would follow her instructions without argument.

"Good," she smiled. "Because this is a very important meeting for me and I want to make a good impression. I'd really like this position so do me a favor and be seen but not heard.

Heath smiled meekly.

"She'll see you now." The front receptionist said. "Eighth floor, room 220."

Thanking her, Cheryl took his hand and pulled him behind her. He felt like a truant child being lead helplessly along. As they stood waiting he could feel the woman's eyes on his butt and caught her wink when he stepped between the doors of the elevator.

The office they were directed to was large but comfortable. Situated on the corner of the floor, it looked out onto a wide view of the city skyline at noon. People scurried between food carts and hamburger stands eight floors below. Cheryl watched him excitedly looking out and smiled at his excitement. It would not do to have him in such a position when the interviewer joined them and she snapped her fingers quickly, commanding him to return to her side. He jumped at the sound and quickly did as told.