In The Tutelage Of Ms. Kline

NOTE: To see original illustrations for this story, please contact me directly. Enjoy!

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The first time Kevin saw Ms. Kline was when she walked up to his parents after church and introduced herself. She was dressed more appropriately for a cocktail party than a Sunday sermon. All legs and black nylons, Ms. Kline wore a matching black skirt that went just barely past her knees. Her black flats seemed conservative enough, but the dark bustier visible through her sheer blouse brought the whole ensemble into question again. The giant wide brimmed hat was very churchy. The tight hair bun and deep red lipstick was more 'Addicted to Love' than 'Praise Jesus'.

Kevin guessed she was in her late forties, maybe even early fifties. She was so lean and well put together, it was hard to tell. Whatever the contradictions of her dress, she easily projected an air of importance.

Kevin's parents ate it up, almost bowing when she introduced herself. The pleasantries she exchanged were mild enough. She was matronly, knowledgeable and commanding. Eventually, the conversation turned to him. He groaned when his mother brought up the 'dilemma' of his unemployment. Certainly, Ms. Kline would have a cornucopia of opportunities perched at the tip of her lips.

"Why don't you have him come work for me?"

"Oh no, we couldn't. We don't want to put you out," his mother protested.

"Oh think nothing of it! I recently had to let some help go and I'm in need of a strong man to help out with some physical labor around the house. I'll warn you though, I have very exacting standards for anyone who works for me. Your son would be treated no differently."

His mother's eyes lit up. He was doomed. "Oh that sounds just like what our Kevin needs!"

Monday morning came and his mother was sure to get him out of bed early. He protested of course, but she would not be denied. After all, Ms. Kline was a lady of importance and it would reflect poorly if he didn't meet his obligations on time. He was ushered impatiently out the door to make his odyssey up towards the hillside estate of Ms. Kline.

He arrived at the gate and pressed the button.

"Kevin?" came the sharp, business-like voice of Ms. Kline.

"Yes ma'am," he replied promptly.

"You're on time. Come up to the house, let yourself in, climb the stairs, and enter the doorway directly across to your left. Understand?

"Yes ma'am," he replied again.

"Good." [click]

The gate clanked and rolled laboriously aside. Kevin huffed an exasperated breath and began his journey up to the house. He did as instructed; entered the mansion, ascended the stairs, and made his way to the doorway on the left.

Inside, Kevin found Ms. Kline, sitting on the bed dressed like she was preparing to go out for the night rather than oversee garden labor. She wore high heels and a mini skirt with a laced up bodice that accentuated her long, taut curves.

"Kevin. Thank you for coming. Please," she gestured to the couch across from the bed. "Sit."

She sounded polite enough, but he dared not disobey. He quickly made his way over, slipping past her crossed legs to sit upright on the couch.

"It's okay," she smiled, crossing her legs in front of him again. "You can relax."

Kevin tried his best, leaning back on the couch. It was deeper than he anticipated. He felt rather prone before her.

"I know your parents sent you here so I could work you on the property and perhaps... teach you some manners," she chuckled, leaning back a bit while slowly sliding her legs together. "...but I must admit I have my own reasons for summoning you." She arched her back, stretching the laces of the bodice that was attempting to contain her ample bosom.

She paused, her eyes appraising him and gauging his reaction. Consciously, he felt violated but physically his body was responding to her subtle, sensual movements. She smiled as they both witnessed the growing bulge in his pants. He was mortified, wanting to cover himself with his hands but knowing he would look even more foolish in doing so.

She addressed it directly. "Don't be ashamed about that," she said, eyeing his crotch. "That's exactly the reaction I was hoping for."

Kevin watched her intently as her eyes strayed up from his crotch slowly to make contact with his. "Take your shirt off."

"Whhaaa...?" he stuttered.

"Take it off," she commanded. "Now please."

Kevin wasn't sure what the hell he was getting into, but he immediately complied. He sat there, shirtless with a bulging crotch and watched as Ms. Kline leaned up onto her left arm and began pulling the laces free of her bodice.

"I see that I arouse you. That's good. I have fabulous tits. You'd love to see them, yes?"

Kevin nodded, dumbly.

"Mmmm, good," she murmured as she pulled a flap free, exposing her firm, shapely right breast. She switched arms and similarly freed her left breast. Ms. Kline then leaned forward and cupped them both before rubbing each nipple between her thumb and forefinger.

"Fabulous indeed, yes?"

Kevin in total awe and consternation at the scene unfolding before him, again nodded dumbly.

"Yes, ma'am." she corrected.

"Y... yes, uh... Yes ma'am!"

"Good." She made a show of rubbing her long legs together before kicking off each of her high heels. She then slid off the bed and onto her knees before him. Her hands quickly ran up his legs, sending a shiver up his spine and reverberating goose pimples along his flesh.

"You see, I was hoping to use you for quite a different purpose." Her hand moved abruptly to rubbing his crotch. "I think you have some... assets, and some potential that I could shape into a very lucrative summer job for you."

Her touch was electric. Kevin felt himself immediately go from mostly erect to the hardest he's ever been.

"You're interested in learning how you can easily earn lots of money this summer, yes? Say, enough to pay for college?"

Kevin stuttered again. He was excited and petrified at the same time. He knew he wanted to say yes to her but was deathly afraid of what she had in mind.

"Yes ma'am," he replied.

"Mmmm... I see we have an understanding. Good. First things first. Let's get these pants off."

She leaned back and waited for him to comply. She offered no assistance. Kevin stood up and quickly fumbled his jeans and boxers down before returning to his prone position on the couch. His manhood flopped around like an enraged, frothy bull.

Ms. Kline smiled as she looked it over before quickly taking it up in her right hand. "Ah, this will do nicely."

Kevin tried to contain his squirming as she listed off a litany analytical terms regarding his phallus.

"Good length. Nice and thick. Very hard - always good. Ample lubrication. Not monstrous, which is good. That leaves anal as an option." She squeezed it rather hard before loosening her grip and jerking it forcefully several times.

"You have a lovely cock Kevin. I'm impressed. So, let's give you a little audition so I know how much work I'll have to do to prepare you for my clients."

"Clients, ma'am?" Kevin asked, momentarily pulling himself from his blissful stupor.

Ms. Kline continued to manhandle him, applying various pressures and tugging him in all directions. "Indeed. A person of your talents, if properly trained, can be a very valuable asset in certain... important negotiations. If things went well, I would reward you handsomely for assisting me."

Kevin tried to imagine what scenarios she could be talking about. It was exciting and terrifying at the same time. She began jerking him furiously almost daring him to cum. He wanted to resist, but his body was entirely enthralled by her possessive touch. His hips bucked as his penis convulsed, spitting his seed lazily over her still pumping fist.

"Mmmm...." he murmured quiety, trying to stifle an outright moan.

She smiled knowingly, as if the outcome had been inevitable. "Aww baby... Did I excite you too much? I wasn't certain, but this really is your first time isn't it?"

Kevin nodded meekly before remembering to add a faint, "Yes ma'am."

Ms. Kline reached behind a couch pillow and produced a towel which was apparently staged for just such an occasion. She made a hasty effort of wiping him down; just enough to sop up the biggest globules before tossing it aside. The last little bit on her fingers went nonchalantly into her mouth as if it was a rivulet of chocolate. Once she had licked them clean, her wet fingers quickly wrapped around his girth again and began stroking.

"Don't worry. We can work on that, but first I need you to stay hard for me for a little bit longer, okay?"

Kevin didn't think he'd have much trouble complying with this request. He was still as physically excited as he'd ever been.

"Yes, ma'am."

"Good. Now here," she said wagging his own cock at him. "Stroke this for me while I finish getting undressed."

She let go of him, rocked back up off her knees and stood. As she began pulling down the rest of her bodice, she eyed him intently. It was only when her stare turned slightly disapproving that Kevin realized his slip-up and quickly grabbed his penis.

"Good. Show me how you stroke it when you really want to cum."

Kevin obeyed, gripping himself firmly and quickly pumping the full length of it. He rocked it at the base slightly on each downstroke waving his slick head like a flag; spittles of precum flitting through the air.

Ms. Kline watched him as she reached around her waist and unzipped her skirt.

"Good. Now look me in the eye. Pretend the slick wet embrace of my pussy is the only thing that will release your seed. You need my pussy. You want to cum in it so badly, yes?"

"Yes ma'am" Kevin replied immediately through labored breath.

"Show me. Look at me. Stroke it harder!" she instructed, a hint of anger in her voice.

Kevin did his best to comply as he watched Ms. Kline tug her dress over her hips and drop it to the floor. She stood before him with nothing on but her jewelry and a sheer white thong. Kevin could feel himself getting a little raw as he continued to beat himself under her watchful eye. For her part, Ms. Kline seemed to very much enjoy the sight of him. She swiveled her hips and ran her hands up and down her thighs, across her gusset and tracing up the taut lines of her stomach.

"Good. Keep going," she said as she began peeling down her thong. "Don't take your eyes off me."

As her panties hit the floor, she stepped out of them and stood there, legs slightly apart. She was completely shorn with not a wisp of hair evident anywhere on her lower torso. The mound of her sex was engorged and slightly red. Kevin could just barely make out the sheen of residue seeping from the lips of her crevice.

Ms. Kline bent forward, breasts dangling over him and slowly leaned in by his ear as he continued to abuse himself at a furious pace.

"You're not going to cum yet, are you?" she whispered.

"No..." Kevin stuttered breathlessly "No, ma'am."

She continued to loom over him watching him go at it. He could feel her hair brush his chest as she turned to admire his effort.

"Does it hurt?"

"Ah... a little. Yes."

"Good," she replied with a bemused chuckle. "Pleasure isn't as good without the offset of a little pain."

Kevin felt Ms. Kline's hands settle onto each of his shoulders. She stepped her legs further apart and moved them in until they were straddling his knees. He felt her hair brushing his shoulders, neck, and back as she moved her head around and wiggled her hips. Her thighs occasionally touched him as she danced, sending jolts of electricity up his legs and to his spine.

"You may stop now."

Kevin was actually relieved to obey. She reached down and took his hand away.

"How are we doing there?" she inquired, playfully slapping his dick. "Feeling a little sore?"

"A little..." Kevin moaned, half in pain, half in pleasure.

"Good. Maybe you'll last." She stood up and moved forward lifting her knees onto the couch and straddling him. With no further fanfare, she grabbed him and fed him inside her. She quickly sat all the way down on him with a contented "Omph."

She began gently grinding him in a fashion that bent him the wrong way inside her. He moaned again, this time entirely out of discomfort.

"Not what you expected for your first time?" she laughed. "Don't worry. I'll take good care of you."

Ms. Kline went quiet, suddenly focused on her task. The painful grinding continued but she seemed more purposeful in administering it. Kevin felt almost as if she was tuning him like some complex instrument. She would sit for a while, grind one way, and then start riding up and down quickly before going still again. Once he got past the awe of such a lovely woman taking his virginity, he started to realize what she was doing. Ms. Kline was flirting with the limit of his next climax. He didn't know how but it seemed she knew his body better than he did. There was no way he could have delayed gratification as well on his own. Once he understood the situation, he gave himself over to it and began to relax.

"Good. Now you're getting it. Eyes on me. Grab my butt."

Kevin complied, tenderly reaching behind Ms. Kline and placing his hands on her backside.

"I said grab," she commanded while adjusting his hand to grab more forcefully on her cheek. "Like this."

Satisfied, Ms. Kline started riding up and down on him again.

"Mmmm..." Kevin moaned. He was getting into it.

More painful grinding pulled him out of his bliss.

"Focus!" Ms. Kline admonished him, "Eyes on me. Remember: it's always about her pleasure, not yours."

"O, okay..." Kevin stuttered.

"Yes ma'am!" Ms. Kline commanded.

"Yes ma'am."

She murmured contentedly at his response and continued to work him. For his part Kevin tried to stay quiet, focused on attending to her with touches and eye contact, while maintaining a detached interest in the skill she was demonstrating by holding him at the precipice of cumming.

As he continued his role, he could sense that Ms. Kline was getting closer to orgasm herself. She became more vocal with sighs, grunts, and suppressed moans. Her riding him became palpably more urgent. There was less grinding and more humping. His suspicions were soon confirmed.

"Mmmm... you're doing very good," she moaned pulling up so that only the tip of his manhood was still inside her. She paused there, adjusting her knees slightly to more comfortably maintain her position above him.

"There's a good boy..." she sighed, "Now fuck me!"

She was relinquishing some of her control back to Kevin. It excited him greatly. She reached back with her right hand and spread herself wide open as Kevin began to buck his hips, jackhammering himself in and out of her swollen wet sex.

"Fuck me!" she screamed! "Fill me with your hot cum!"

She knew it wouldn't take him long but it didn't matter. She was already going over the edge, whining with pleasure, pushing back hungrily against his thrusting.

"Oh God baby! Your cock feels so good!"

"Yes ma'am!" Kevin erupted, pegging his thrusts as his seed pumped deep inside her. He felt simultaneously exhilarated and sheepish. The euphoria of his first sexual encounter and the strength of his orgasm mixed with the confused feelings about being dominated by an older, strange woman.

She sat down on him as he continued to throb, enjoying the sensation of his thick cock pulsing deep inside her. She smiled.

"Oh baby boy... You and I are going to have so much fun together. There's so much you need to learn," she said in a friendly tone, patting him on the chest. "But I think I'm going to really enjoy teaching you."

She sat there quietly, slowly milking him with her hips and smiling at him. Kevin remembered his eye contact, despite wanting to roll his eyes up and moan. When his throbbing finally subsided, Ms. Kline gently braced against his chest and lifted herself off him. His manhood, slick with his cum and her juices plopped free and continued to dribble on his stomach.

Ms. Kline carefully slid from the couch and stood before him. She looked him over and licked her lips as if she was pondering some additional fun. Apparently deciding against it, she turned and stepped away.

"Get dressed. Your payment for today is on the table in the hallway. There is also a list of chores. Please complete them before leaving. Be back here again tomorrow at 9am sharp."

Kevin was slightly confused. He was still expected to do manual labor?

"Ma'am?"

As if reading his thoughts, she replied. "Yes. I still expect you to do some work around the house. You could use some more sun and some more... definition. Don't worry honey. So long as you do what I ask, I'll make sure it's worth your while."

She smiled and disappeared into the master bath. Kevin sat alone in the sudden quiet, staring at his recently abused penis as it slowly resumed its normal shape and size. He couldn't quite believe what had happened to him but was more than eager to experience it again. He decided rather quickly that anything she asked of him would indeed be worth his while.

He dressed quickly and slipped from the bedroom. On the table by the door were two crisp one-hundred dollar bills and a handwritten note on fancy stationary. It contained detailed instructions on where to find her hedge of oleanders, how she wanted them pruned, and where to haul the trimmings. Manual labor indeed. At least he had been paid upfront... in more ways than one.

Kevin didn't see Ms. Kline, or anyone else that day as he went about the property and carried out her instructions. The oleanders were huge, reaching over 15 feet tall. There were twenty of them walling off the main garden on the property. Kevin was no professional gardener, but it was easy to tell how overgrown they were and how much trimback Ms. Kline would deem sufficient. It took him the entire rest of the day of hard labor to get them cut back and all the rubbage cleared. Normally Kevin would've found some way to slack off or cut corners, but he sincerely feared the displeasure of his benefactor. It would be one thing to get fired and sent moping back to his parents, but the thought of never again being invited to her bedroom worried him more. Besides, Kevin would be hard-pressed to find any other job that paid $200 a day, so he made an earnest go of it.

When he was done, Kevin was filthy and drenched in sweat from head to toe. He bore red marks on his face and arms from where the branches had scratched and irritated his skin. He smiled to himself. So this is all it took to get him to lift a finger and do something useful. His parents would be proud. Little did they know how motivated he was to return. He decided not to tell them how much he was getting paid. They would be aghast and demand he return most of it. It dawned on him that he would be keeping a lot of secrets for Ms. Kline. The prospect excited him as he briskly made his way from her property in the fading daylight.