Sharon Winters allowed Richard another shower but remained silent in the doorway as he washed himself. Time was running short and she didn't have the opportunity to take as much a part in it as she'd have liked. She noticed his erection had subsided almost completely which either meant he had ejaculated (not likely) or he was growing accustomed to being naked around a house full of women, neither of which was a good sign.

His body was glistening with sweat as he entered the shower room and seemed to react to the soothing effect of the warm water. His skin was flushed from the run. As he finished she handed him a towel. He dried himself quickly. Lingering between his legs he playfully juggled his balls against the thick plush towel. Ah, boys and their toys.

"Come on then, you'll be late for lunch."

Used to the routine, he made no attempt for any covering and instead walked proudly by her side. One of the maids watched him and he winked at her playfully. Looking over at his guide she made the smile drop from his face when she stated; "That one could do with a good whipping."

Sharon only smiled in response. In truth she was feeling very close to the boy and had grown protective of him. She'll decide if he needs a whipping. She only hoped it would be her that gave it to him.

As always, lunch was wonderful. The cook was ready with a BLT, French fries, milk and a bag of potato chips. Though his coach would not approve, she thought he could use the extra food. It had been a long morning.

When he finished she took him to the bathroom at his request. He had not needed to go since he arrived the day before and could barely hold it in when she guided him to her personal bathroom. She stood facing his side, eyes directed towards his penis and he stood silent staring into the bowl.

"I can't go with you watching me like that," he whispered.

Sharon jumped. "Excuse me?"

Sighing, "I just can't. I never could with someone in the same room with me." Then, even more quietly, "sorry."

She didn't want to poke fun at his obvious moment of weakness but she couldn't resist, "Lots of boys are shy. You'll just have to get used to it. It's something you're going to be living with from now on."

"Do I haveta?" He was nearly pouting now, quickly falling into his role as the whining child.

"Yes mister, you do. You better learn quickly or it will only make it harder on yourself. She added, "And your bottom."

He resisted, twisting his body so his member was pulled from her hand. She knew it was late but she expected something along these lines. It's rare to take a boy in so easily without a tantrum his first few days of training. She knew there was only one way to remedy this. It had to be stopped immediately.

Grabbing his earlobe, she pulled him from his place in front of the commode and into her bedroom. He had never been in this room before and looked about in awe at the soft down bedspread, pink wallpaper and frilly curtains. A scent of jasmine filled the air and he felt very at home in this place, the room where the woman he was learning to love spent her most intimate moments.

Without a word she held his wrist and, sitting on the edge of her bed, directed him to her waiting lap. He stubbornly resisted and in that moment, his limp penis swinging beside his loose balls, Sharon thought he looked incredibly childlike. Biting his lower lip he could only pull away mumbling, "No.please. I hate that.I don't need it."

Sharon grew more and more aggravated, "When was your last spanking Richard?"

His eyes widened, "Never!" Realizing his lie he caught himself, "Not since I was very young."

She knew it. She seemed to have a natural instinct to sniff them out. "And who spanked you?"

"My mother, Miss," he added the last word on at the last moment. It seemed more appropriate.

"She was a wise woman. Boys need to be spanked. Hard and often." She looked up at him with soft eyes. "When I have boys of my own you can be sure they will be lovingly spanked as any good mother would."

"Please don't, I'll be good," he begged, cursing himself for sounding like such a child.

This was working out just as she'd hoped. "I know you will. I'll make certain of that." Taking his hands in hers, she had him kneel beside her and looked into his eyes. "When was the last time you were spanked, honey?"

He stammered, "Fifteen.no, sixteen. When I was sixteen."

She laughed gently. "Hardly very young, wouldn't you say?"

He nodded.

"You were most likely a very disobedient boy and like any good woman, your mother knew how to correct you. She spanked you as is the right of any woman over her boy."

He sighed, lost in remembrance.

With a hand on his shoulder she continued. "She is no longer here but I am. For all purposes, I am your mother. Just as your place is to obey me, it is my job to punish you when you require it."

With tiny shudders, he dropped his face, unable to meet her gaze. She was right, he couldn't deny that, but he was so afraid. Ashamed and afraid of this beautiful woman seeing him bared and spanked as he was just a few short years ago. He could never take a spanking, always whining before ending up fussing and crying over his mother's lap. This was a side he didn't want her to see. A tear formed in the corner of his eye and began its descent down his cheek.

"What are you thinking about, young man?"

A breath choked in his throat and he couldn't answer. He seemed such a sad sight, her heart truly broke to look at him. It took all her willpower not to gather him into her arms and rock him until he calmed but she could not. It was her duty as a woman to give this boy what he needs, a hot, stinging spanking the likes of which he hasn't felt in years. It's what he needs and the only thing that will put him on the right path. She steeled herself and, with a finger beneath his chin, raised his eyes to hers.

"Richard, in just a moment you will go over my lap to be spanked. It will hurt and it will sting like the blazes. You'll be very embarrassed and I promise you you'll cry until you're all out of tears. You'll do anything you can to stop it but know it won't be over until you've gotten spanked properly and I think you've learned your lesson." His lower lip was trembling uncontrollably. "You can take comfort in the fact that though I am a strict woman and will spank you beyond what you think you can handle, I won't hurt you. You're a good boy and I do love you. That's why this has to happen."

Her words stunned him. He realized that she'd been feeling exactly what he was and for a moment he felt euphoric. He attempted to stand but his anxiety froze his muscles and he relied on her help to lay across her lap. Once there he felt slightly relieved. He was fully aware of how he looked- a grown man across the legs of an older, beautiful woman- but he put it out of his mind. He felt her eyes on him and hung his head.

His backside must be the most attractive part of him, she thought to herself. His perfectly muscled, tight ass seemed cut from the pages of an underwear ad. His skin spotless and, newly shaven, sensitive to her touch. Tiny goosebumps appeared as her fingers brushed over him. His cheeks lined up proudly against his deep cleft. Carefully she pried them apart to look in the smooth hollow of his bottom. The tiny vortex of his anus looked back at her innocently.

Sitting up, she stroked his back lovingly. "Are you ready Richard?"

He nodded, managing a weak "Yes, maam."

She flexed her fingers and slapped the heft of his cheek quickly. As she pulled back she watched it spring back almost instantly. The fair color of his body turned the faintest pink. Three more blows landed rapid fire across his cheeks and he stiffened. She noticed he was holding his breath and caressed his backside tenderly until he regained his breathing.

She continued her assault on his backside. Stinging slaps landed from his upper thighs to the very top of his smooth cheeks. She became one with the motion, concentrating only on his rear and applying her spanks accurately. Soon she heard a slight whimper come from her side and she was saddened. He needed this and would most likely receive much worse during his time here but seeing him in pain affected her deeply.

The spanking continued and the slight sting in her hand grew to an aching. His butt had turned a blotchy red and he had begun crying. As the crying turned to uncontrollable weeping he began kicking his legs. This always upset Sharon and with a stern scolding peppered with extra hard spanks against his most tender areas, she got him to drop his feet and remain still over her knees.

The skin of his bottom was hot to the touch. Though she always found this image intensely arousing, she regretted the warmth that began in the crotch of her panties. Clenching her teeth, she continued. He was taking his punishment very well and Sharon hoped it would be over soon.

Repeating her warning of staying still, she launched another fusillade of strikes against his hindquarters. His weeping had turned to pitiful wailing and in between sniffles he pleaded with her, his words coming out unintelligibly.

The last strikes landed and Sharon breathed a relief. Her hand had the proper effect on him and she now used it to stroke his swollen backside lovingly. His gulps of air subsided and as his tears decreased, she sat him on her lap rocking him in her arms. The last of his tears stained her collar and he felt calmed by the warmth of her body. Her scent flooded him and despite his stinging rear he felt himself swell in response. She noticed this as well but ignored it and concentrated on rocking him gently and humming to him.

With a kiss to his tear stained cheek she led him to the bathroom and took up where they left off.

"Let's try this again. Put your hands behind your head. This is how we're going to do this until you grow up." She held his soft penis in her warm hand and aimed it towards the waiting bowl.

He gulped and with a look to the ceiling, let out a frustrated breath of air. True to his word, his pipes seemed to stop up. Despite his urgent need just moments ago he couldn't let go. She continued holding him, certain to wear him out.

"Come now, you are making us late."

He winced and a small droplet appeared on the tip.

"There's a good boy. I knew you could do it. Just relax and let it out."

He knew he could, knew it was physically possible, he was just shocked at the thought of such an act in front of a woman and a beautiful woman, one that he was growing fond of.

As expected, nature won out. His flow increased from a trickle to a steady stream. He held his breath the entire time and shut his eyes tight. The act was too much for him and he forced his body to run on autopilot this one time. He finished and attempted to shake the last few drops from himself.

Sharon chided him and told him to stand still as her small hands shook him vigorously. It pained him slightly but he managed to bury it under the more potent emotional stress he was going through. With a smile she tapped the head with the index finger of her opposite hand to finish him off. Though it was a small act, she took pride in what had transpired between them. The men in the family must understand their position as subservient to the women. Taking away a basic male standard- peeing in private- pushed him further in that direction. It shamed him and made him realize his lack of power, something most men are regrettably never taught. From birth they believe they are the ones in control, while all the time oblivious to that which makes them weakest- the love and power of a woman that knows how to wield it.

On their walk across the estate he could not look her in the eyes. In fact, it looked like he did all he could to avoid her gaze. She did not mind, she had made a major step in his progress and wanted to allow him some time. The next step could break him if he wasn't treated with kindness and she never wanted him to think of herself as anything but someone to look to for guidance. She took his hand and he didn't fight. All those that saw them admired the sight of a beautiful, proud woman, leading a sad looking naked boy with a well spanked bottom behind her.

Diana Donnelly lived in a villa on the edge of the property overlooking the beach. She was the first employee of the Burkes and a daughter of Theresa's best friend. When her mother passed on she moved to live with the family where she busied herself doing everything from the family's finances to cooking and tending her personal garden. Years ago she was selected as the teacher of the males' most important subject, husbandry. Working closely with Theresa, they decided what traits they most preferred in a husband and what they expected of the men that would marry the Burke daughters. Together they planned a regimen of sexual technique, servitude and sensitivity. The men must learn how to please their women, for that is their most important job, but they also must learn how to accept a woman's domination and know how to follow orders. Though few are born with the sexual skill, she has never met a one that knows his place. Over time she had become expert in teaching them and thought of that fact with pride.

They waited side by side in her living room. Richard sat bent over his closed legs. His elbows were folded on his thighs, effectively giving him the look of a nervous child awaiting the principal. Sharon fed off this image, reclining beside him on the sofa. Her hand stroked his back possessively as the top of his cleft drew her attention.

Diana was aware they were there and viewed the scene unnoticed from her spot on the porch. The boy was a fine catch, easily the best choice any of the daughters had selected. He seemed afraid, though she couldn't be sure if that was due to his nudity or what he had already been through. She hadn't been informed if he'd been punished yet though he may have well been. Some of the women in the household were quick with the hairbrush and leather strap. All the males on the estate can attest to that.

Fixing her hair, she opened the screen door and entered the room. Sharon stood on her arrival and when the boy didn't she jerked him by the elbow. She spoke to him quickly, most likely admonishing him for his forgetfulness, and he looked sullen. The two women shook hands and, when he offered his, she pulled the boy into a close hug.

"You must be Richard?"

He nodded. "Richard, it's very good to meet you. My name is Ms. Donnelly. For the rest of the day we will be together."

He remained silent.

"I know you may have had a difficult two days. Your report says that you are so far excelling in all that is asked of you. It looks like Sharon and the other ladies are doing a fine job." She smiled at her peer, who took that as he cue to go. When they were alone she bade him to sit cross-legged on the ground while she took a seat on the easy chair. He seemed very uncomfortable in this position though he did as she told. He hung his head and covered his genitals. He had not said a word the entire time he had been inside.

She paused and stretched, allowing him to get a good look at her body. She was by far the most beautiful woman he had seen on the estate, perhaps the most beautiful woman he had ever seen. She was a natural redhead that, along with her fair, flawless skin, betrayed her Irish heritage. She was not athletic like Nancy or sculpted like Sharon, rather she was buxom and rounded. Her breasts were heavy and perfectly shaped, drawing attention away from her firm, wide hips. She was the classical feminine form; not obese or muscled. She was more womanly. Her curves seemed formed to appeal to men's most base nature. Wherever she went she was sure to draw stares from men that would lose themselves to spend one evening between her smooth thighs.

She was having exactly the affect on him that she hoped for. Leaning forward she placed one elbow on her knee and began.

"You'll learn to enjoy your time here with me though it won't always be easy. I'll teach you how to be a man and how to be the perfect husband. The most important thing you can ever do is serve your wife faithfully and I intend to show you just how to do that."

He nodded, unable to look away from the cleavage swelling from her unbuttoned blouse.

"Most likely a man with your looks has bedded many a woman. It is not difficult to find a woman willing to open her legs to a man though I would suspect you have not learned how to use your equipment in any way but for your own pleasure."

She leaned forward, caressing his cheek with a silken finger.

"You'll forgo your own pleasure to learn how to please a woman- your wife. You'll learn about a woman's body, something I doubt you've taken the time to have little more than a passing knowledge of. Beyond that, I'll teach you the finer points of being a man- listening to your woman, setting a good image for her, making her home and bed a place where she will thrive."

He looked like he was to speak but she continued before he could. "I'm sure you're very nervous, unsure of what you've gotten yourself into and most likely scared. That's natural and you shouldn't ignore those feelings. All I can tell you is, like the other ladies caring for you, I'm a sweet woman. I know men very well and find them to be dear creatures. I love them and understand their needs. When you place yourself in my care you're completely safe and though I may do things to you that will hurt, I will never harm you." With a hand on the back of his neck she pulled him towards her. "You have my word on that." Her lips touched his and she planted a deep kiss on him. Her tongue slid along his lips gently, causing his mouth to open. With a soft urge, she pressed her tongue into his, possessing him. His body reacted to her and, cock swelling, he leaned into her. As he did she broke away, smacking her lips together.

"A good start. You obviously have some talent in that area. Still, you have some areas that could use work. I'll make a note of that."

He rose on his haunches, his penis pointing towards her. As she stood he turned to face her.

Noticing his state she commented, "I'm glad you find me attractive. That will make this easier for the both of us." She began undoing the buttons on her blouse and slipped it off her shoulders, displaying a black satin bra full to bursting. She turned her back and he noticed the creamy texture of her skin, complementing her lush red hair perfectly. As her jeans dropped to the ground he noticed a thin band of black separating the heavy cheeks of her perfectly toned ass. He reacted with her, following her every move, studying the tiniest detail of her beautiful body. When she turned his eyes followed, resting on her firm, heavy breasts. She had tiny nipples that swelled as he watched. All he wanted at the moment was to rise and suckle her. He knew he dared not, not without her permission. He was so entranced with her perfect curves and smooth texture of her skin that he did not notice the shiny black phallus that tilted from her hips, incongruous on this perfect female body.

She held it possessively in her hand and squatted to face him. As she ran her hand through his hair playfully she said, "If you're going to learn how to make love to a woman, you must first learn how it feels to be a woman."

Richard gaped. This was more than he expected, more than he ever thought he would take. On any other day, with any other woman he'd have demanded his clothes and left without a thought but something compelled him to stay, his knees remained rooted to the floor and his cock continued to rise.

Placing a hand on his shoulder she bade him to stand. Her member hung inches from his upturned face and for a moment he feared she would command him to mouth it as he'd so often done to his lovers. He feared that would be the final straw and he would fail. He would not be able to; just the thought turned his stomach.

Instead she merely helped him stand and took him in her arms. He showed no reaction and allowed himself to be pulled to her though her stiff phallus prodded him, challenging. She stroked his cheeks lovingly and with a finger beneath his chin, placed a soft kiss on his closed lips. Barely speaking the words, she mouthed; "Relax, give in to me." He knew he could do nothing else.

This time he kissed her more passionately. His lust drove him and his licked her full lips, gently taking one between his and sucking it. The point of his tongue dabbed at the corners of her mouth and she allowed him to hold her chin in his palm. He was frenzied but controlled which, in his state, surprised Diana.

She allowed him his turn then guided him, sliding her lips over his to demonstrate the proper technique of how a man should kiss a woman. Her fingers caressed his cheek, which caused him to flow into her. This woman understood how a man feels and played him expertly. With only a few kisses and tender caresses he felt himself taken in her grasp.

The dildo strapped over her wide hips poked him in the scrotum, causing him to clench his jaw. He feared it but knew in the hands of a woman like Diana, it would be used with only the utmost care.

She led him to her bedroom where she positioned him by the side of her bed and, with a gentle press on his shoulder, bent him over. His weight rested on the palms of his hands and with gentle encouragement, she had him press his cheek to her fluffy bedspread. His arms reached out to either side prone on her bed.

In this position she discovered the state of his ass. It was swollen from his recent spanking, with bright red spots surrounding slight bruising. She pitied the male and knew how hard it can be for the men in this family. He had just begun his training, however, and it wasn't out of the ordinary.

She traced the outlines of his welts slowly. "You've just been spanked," she said, almost a question.

"Yes, Ms. Donnelly."

She wanted to make him feel better. "You probably deserved it, Sharon's a good woman but she can have a heavy hand when she needs to. I'd watch my tongue around her from now on if I were you, cutie."

Her hand wrapped comfortably around her shaft. She always enjoyed this side of herself; the primal urge she felt when taking a man anally, and she adored the feel of a strap on hanging almost magically below her navel.

Taking a tube of lube from her night table she squirted a generous amount into her palm. Lovingly she slathered her toy with it until its surface was coated in layer of gel. On her command he reached back and spread his asscheeks as wide as he could. Inside he was smooth and shaven, Diana noticed. Before she covered his back passage with the lube, she stroked his crack with one outstretched finger until it rested on his hole. When her hands touched his worn skin he cried out.

"Easy, boy," she cautioned.

Slowly she dripped the gel onto the softness of his bottom. Knowing too much is not enough, she spread it from the beginning of his crack to the very back of his balls. A great amount was spread along each cheek and down the sides. This was for her own pleasure, as she loved to feel the slick wetness of a boy's ass when she was inside him.

Steadying herself with one hand on the back of his neck, she directed her cock against his passage. He tensed and made a groan of discomfort.

"This is going to happen. Don't fight me or it will just be uncomfortable. Relax and give in and you will enjoy it." With a slow, practiced movement, the tip of the featureless rod penetrated him. He whined.

"I know, I know, sweetheart. I know it hurts. It's supposed to. Just let Ms. Donnelly take care of you now. I know what boys need."

He looked delicious like this. Face pressed into the mattress, one hand clenched into a fist, the other spreading himself for her, she watched his sphincter slowly dilate to allow for her member.

Grasping the meat of his buttocks in each hand, she pressed ever more slowly into him. His voice came out in a deep moan into the bedsheet. He was having difficulty but remained docile. More than likely his spanking was the reason.

She felt his ring open and her length easily slid into him. He froze from the pain and she rested to allow him time to process the feeling. Her hair rested on his bare back and she swayed it over his skin to soothe him.

Slowly he started to breathe again and Diane pulled out just as carefully. He seemed relieved by this and his entire body seemed to react. His tight anus clung to the invader as she withdrew. She reentered him and found his passage slick with moisture. It didn't hurt him as much as it did and with each successive thrust it hurt even less.

Face still pressed to the mattress he refused to admit to himself that he found it enjoyable. This was not how men were supposed to feel. A woman is made for such things. Men were the penetrators. He remembered the times he'd entered a woman's ass, feel her clench and think of how good it felt.

Diana grew more insistent as she watched the dildo slide effortlessly into his ass. With the pace she was going, she was able to free a hand to stroke her nipples as she fucked the boy. He had a beautiful ass, and watching him split and opened excited her more than she thought. Cream formed beneath the dildo harness and she wished for room to slide her finger between it to massage her sex.

His cries turned from pained whimpers to bursts of excited pleasure. To Diana it seemed he hadn't expected to enjoy it the way he did. This brought her an unexpected sense of pleasure. Not many males accept this role so soon or so easily but some take to it as if they were born for it. Emily may have found a stud with a latent bitch inside.

"That's it boy. Sit there and let yourself get fucked. Take it like a good little bitch," she taunted.

This seemed to both aggravate and excite him as he reeled up to protest only to squeal happily when her dildo brushed his g spot. Reaching under his armpits, she pulled him up so he was on his knees away from her. She whispered in his ear;

"Good boy, you know how to take it so well." Holding her hand to his back entrance to feel the slippery shaft stroke his canal she teased, "Your ass knows just how to open for me. Do you like that?"

He nodded eagerly and when she reached around to feel his cock it was throbbing and swollen. She continued pumping into him as she wrapped one arm around his chest while the other held his head and pushed his ear towards her lips. She bit his lobe, tugging it hungrily.

"Lie down. I want you on your back."

Without a show of resistance he complied. She was able to maneuver him onto his back so just the tip of her shaft remained inside his asshole. Leaving it there for a moment, she examined him.

His balls were drawn tight against his body, partly from fear and partly from a need to orgasm. His hands wanted to fist his length but remained clasped at the sheet above his head. His mouth was opened slightly, his head turned back. The expression on his face was a combination of fear, nervousness, shame and outright lust.

He was unable to understand all he felt. He knew he shouldn't give in to what he felt so easily but it was a pleasure completely foreign to him. It stung him and brought him right to the edge, holding him back from taking the plunge he knew must happen. It teased and stroked him. It felt as if someone had reached inside himself and masturbated him. It was an agonizing feeling, not being able to go any farther and, as she watched, tears started to appear in his eyes.

Her hand was on his balls now, squeezing playfully with each thrust into him. He felt like a puppet, his arms shaking on their own commands.

He reached toward her, feeling for her breasts with his eyes closed and she allowed him this pleasure. With a clumsy grasp he located one and gripped it almost tightly. This drove her to greater heights and soon she was pumping into him with a frenzy, her wide hips making loud slapping sounds in the room. He squealed with each thrust and she tugged on his balls, playfully slapping them. Tears spilled from the tightened cracks of his eyes and, before either of them were aware, he peaked.

He did not climax, at least not fully. It was more of a dull sensation turning to a pleasurable tickling before dissipating at the tip of his thickened shaft. Heavy blobs of jism shot from the head to land in patterns on his chest. Each burst was following by a high pitched wailing that lasted long after his balls had drained.

Diana held his body steady, allowing him to feel this special moment. She had not yet reached her orgasm but knew there was time for that. The lesson had just begun and there was time for her later. For now she allowed him to curl into her as she pulled her cock from his ass with a loud 'pop'.

Like a wounded animal, he breathed deeply and hid his face between her breasts. She breathed with him as she felt his tears on her dampened skin. This was a special moment in a boy's life and she was honored to share it with him