When a Boy Loves a Depraved Valkyrie

When a Boy Loves a Depraved Valkyrie 1

By Harriet Marwood
harrietmarwood@protonmail.com

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This work is intended for ADULTS ONLY. It may contain depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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When a boy loves a depraved valkyrie part.1

By Harriet Marwood

Feedback at: harrietmarwood@protonmail.com

This work is intended for ADULTS ONLY. It may contain depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.

“And remember to give Benjamin his Puericil pill before bedtime!” Mrs.Worthington yelled from inside the kitchen, searching high and low for her car keys “Now where did I put those... there!” She picked up the keys and hurried into the living room, smiling down at her timid son, standing there in his jammies beside the new babysitter. “Actually I brought the creme solution variant, for rectal administration” Melissa said matter of factly “My mom says it’s the most efficient way, and with less side effects” Mrs. Worthington stopped to consider the validity of using such methods. She noticed that her son’s face had turned an even deeper shade of crimson - understandably.

“Well... your mother is a doctor after all. I guess she knows best. Besides, It would be nice to eliminate his bedwetting. He's been having bladder problems ever since I put him on that stuff”.

Melissa smiled broadly and, stifling a giggle, she replied “Well, he’s still just a little boy. It might not be a side effect of puericil” - it most certainly was.

Mrs. Worthington felt sorry for her son. Benjamin was so obviously infatuated with the neighbour girl. How often had she not caught him spying on Melissa, whenever she passed by on the street. And now his naive hopes of establishing something resembling a romantic relationship was being trembled by the sheer asymmetry of the situation. Well, he might as well realise this sooner than later, she thought. At 16, she was three years his senior. Hopefully Melissa would be delicate in her handling of Benjamin’s innocent passions.

Mrs. Worthington was indeed correct in her assesment of Benjamin’s boyish infatuation, but had she known the wicked thoughts racing through Melissas mind it is hardly doubtful that she would have chosen another sitter. In fact, unbeknownst to the singlemom, Melissa’s hand had snug down the back of Benjamin’s pyjama bottoms, and her long middle finger was circling around his tightly puckered anus.

Poor Benjamin. He had fallen in love with the most depraved teenager you ever could think of.

You see, Melissa was a bit unusual in her tastes. Unlike most teenage girls she didn’t find anything appealing about the astretics of the masculine. She liked her boys young and undeveloped, and she loved to humiliate and dominate the boys who were so unlucky to be trapped in her snare. Quite a few of the boys at school had had the taste of her strapon-dildo. To Melissa there was nothing more satisfying than taking a young boys virginity with her enormous rubber phallus. She was of the opinion that regular sex was a gross misunderstanding. A young boy’s bottom was meant to be fondled, penetrated and fucked. Why else would god have given them such irresistible, tender anuses?

She had preyed on Benjamin for a long time. He was one of the few boys in town who had been put on Puericil from an early age. In fact it was Melissa who had pleaded with her mother to convince Mrs.Worthington that Benjamin ought to be put on the drug for health reasons. This meant that, developmentally, Benjamin still looked like a prepubescent kid a couple of years younger than his actual age. To Melissa he was the most beautiful specimen she had ever laid her eyes upon. Delicate, boyishly feminine features, hazelnut hair, big brown eyes and most importantly; an adorable bubble butt.

His lack of development had made Benjamin even more timid and shy than his already inhibited disposition. He had become a loner, spending most of his time confined to his room. In school, his social considerations mostly consisted of trying to avoid being the victim of bullying.

Gradually she had lured him in. At first she sought out his eyes, sending him a blinding smile every now and then, which of course made him blush furiously. Then she began sitting next to him on the bus. This caused some confusion on the part of Benjamin. What exactly was the most beautiful girl in school doing sitting next to him, a notorious reject with hardly any friends?

To be sure, he was overwhelmed by the presence of this tall, extremely gorgeous woman. Melissa was the most stunning thing he had ever seen, and her fabulous, overtly sexy body left him swooning with desire. It was only with great difficulty that he was able to stop staring at the two mammoth melons straining her bra and the semi-sheer fabric of her filmy white blouse. Contrary to Benjamin, she was very well developed for her age, easily passing for a woman in her twenties.

She asked him questions, showing genuine interest in his passion for astronomy. She would even laugh at his geeky astronomy jokes, and compliment him on being such a “clever boy”.

Then soon after came the light touches - on his forearms, on the nape of his neck and the inside of his thighs. Melissa was an expert in the art of seemingly innocent strokes and caresses. Whenever they met or seperated she gave him a long, maternal hug, pressing his face against her soft chest.

Benjamin’s feelings of attraction and adoration soon became a spellbound devotion. Whenever he saw her the butterflies in his stomach spun around like mad. It was pure puppy love.

Then came the embarrassing questions. She never changed her warm and kind demeanor, yet her direct manner caused Benjamin quite a bit of embarrassment.

“My mother told me that you have been on puericil for two years. Is that true?”

Benjamin felt like crying as he told her about his predicament. Surely she couldn't possibly want to associate with someone who was technically still a child. He expected a reaction of disgust or disappointment but instead she had placed her hand on the small bulge in his shorts causing Benjamin to freeze.

“So you’re telling me that you are completely hairless down here, just like a little boy?”

Benjamin nodded his head, eyes downcast in shame.

Then the most wonderful thing had happened. Placing both her hands on his face, she closed her lips over his with a gracious tenderness. Moving her tongue slowly and sensuously between his parted lips, she kissed him deeply, feeling his young body tremble with emotion.

Benjamin was in heaven.

Breaking off the kiss she whispered into his ear; “You are just the cutest little thing ever. I can’t wait to get you undressed so I can have a good look at all your delicate boy charms”

Benjamin didn’t know what to say. He was much too innocent to fully process her vulgar desire.

From then on Melissa got more and more direct with him. Caressing and kissing him, she would ask him questions like:

“When was the last time someone saw you naked?” (Age 8) “Have you ever masturbated?” (No) “Have you ever had anything up your bum” (Most certainly not!)

Melissa enjoyed his embarrassment immensely. Finally one day, when she found that Benjamin had been sufficiently tenderized, she told him what was in store for him, and his taut behind, if he wished to be her boyfriend.

“What I want Benjamin, is your cute little bottom. If you want to be my boyfriend, that means your tight little boypussy belongs to me. I will be loving and gentle with you, but I want complete obedience at all times, no matter the circumstances.”

Even though Benjamin was shocked and frightened beyond belief by her rather unusual request, the choice was easy. The thought of not being near her, to no longer feel her embrace, was unbearable to Benjamin. So strong was her hold on him that without a second thought he whispered “Okay...”

Benjamin did not have the slightest clue as to the how and when of her deviant plans. There was no obvious place and time for a 16 year old cheerleader and a 13 year old geek to commence in such activities. For now, he was overjoyed that he could call himself her boyfriend. But soon enough Mrs. Worthington informed her son, that the neighbor girl had so graciously offered to babysit him while she visited her sister up north, for the whole weekend.

Normally Benjamin was allowed to look after himself but Melissa’s mother - the omniscient, all knowing doctor - had yet again convinced Mrs. Worthington that a thirteen year old boy on puericil was much too immature to look after himself.

And now Benjamin was getting his little bum fondled while his mother packed the last of her things.

“Al right. I think that was everything. Give me a kiss”

She bend down and gave her son a quick peck on the lips.

“Remember to do everything you are told - otherwise I have given her permission to spank you. Now be a good boy for her, okay?”

“Yes mommy” the boy answered obediently.

“Bye bye!”

They stood in the doorframe waving as she drove off into the evening sun. Steering Benjamin by the neck, Melissa took him inside and closed the door.

“Well, well... a whole weekend with you all to myself” Melissa said pulling Benjamin into her embrace. Her 5 th 9 dwarfed his 5 ft. 1. Quickly her hands found their prized target; his soft bottom. “We are going to have so much fun”

She gave him a quick kiss before releasing him. She grabbed the old physician's bag that she had brought along. “You will be familiar with all the contents of his bag by the end of my stay” she said obscurely and laughed. Taken his hand she lead him into the living room. She sat in the large armchair and placed the frightened boy between her knees. Even though she was seated, they were still on eye level.

Melissa hadn’t been this turned on in years, if ever. The prospect of having this beautiful creature under her control, for the entire weekend, made her dizzy with excitement. Her mind was racing with all the wicked things she had planned for him. One thing was sure: by sunday he would have great difficulties walking straight.

As she spoke she began unbuttoning his shirt. “Tell me Benjamin. How much do you love me?”

The boy was obviously terrified, yet he managed to utter, In a quite voice; “Very, very much Miss”

Melissa was amused that the boy had started to address her as “miss” on his own accord.

“Well, now is the time to prove it Benjamin. If you show me any disobedience, even in the slightest manner, I will blister your bottom with my wooden paddle and the two of us will be done for good. Do you understand?” Her tone of voice was much harsher than usual.

“Yes miss. I will be good boy. I promise”

“Very good.” Melissa said, returning to her more loving, warm demeanor.

She finished with the last botton and pulled the shirt from his shoulders, exposing his smooth torso. Melissa caressed his beautiful upper body.

“Now, there is a few more rules that you must adhere to at all times”

Benjamin nodded. His was being torn apart by powerful conflicting emotions. One part of him wanted nothing more than to feel her gentle touch upon his skin. The other part wanted to run away as fast as he could.

“First of all. When the two of us are alone you are to call me mommy. Got it?”

“Yes miss... I mean mommy”

“Very good. Second. You are not allowed to play with, or even touch your own genitals.”

As to accentuate her point, she cupped his small bulge on the outside of his pyjama pants.

“Yes mommy”. The boy could have died of shame.

“Third. And this rule follows logically from the second. You are to inform me whenever you have to use the bathroom. This way I can make sure that you do not touch yourself in inappropriate places. And ofcourse, from now on you will be sitting down while peeing. That goes without saying. Also, bathing yourself is obviously a thing of the past”

Yes mi...mommy”

“Fourth. Your butthole is to be referred to as your boypussy, understood?”

Yes... mommy”

“Very good Benjamin. Last and most importantly. You body is now my property. I can undress and dress you whenever and however i see fit. I can touch and play with your little body however I so desire. I can photograph and film you if it amuses me. And I can share you with whomever I like. In short: I own you”

There was a brief moment of hesitation. Melissa looked into his eyes with a disapproving, piercing gaze.

“Yes... mommy. Sorry mommy” he quickly answered.

“Excellent. You are being a very, very good boy Benjamin. Keep it up, and you might just prove to be the perfect boyfriend material”

By now Melissa had moved her hands together over the front of his pyjama bottoms. Delicately she took the cord and pulled the ends. She could feel the nervous jolt of shame run through his body as the bottoms slid down his legs to the floor, exposing a pair of batman undies. Melissa stifled a giggle and placed her hands upon his hips and spoke to him softly; “Aren’t you a little too old for such childish undergarments”

Benjamin had difficulty speaking. “I don’t like them either” he managed to squeak out.

“I’m only kidding Benjamin. I think they are just perfect for a little boy such as yourself. Although, starting from today, I will be dressing you in little girly panties. But we will get to that part soon enough sweety pie”.

“Now, I have been looking forward to seeing just exactly what you have been hiding under those tightly fitted school shorts.”

Digging her fingertips into the waistband on his undies, she traced her digits around the rim, postponing the inevitable baring of his naked form.

“Anything to declare?” She asked with a wicked smile before ever so slowly peeling the fabric down his slender legs. The fabric clung to the underside his small, hairless genitals as a last line of defence.

Finally the undies dropped to the floor. He now stood naked as the day he was born. Instinctively, his hands flew to cover his modest package but Melissa quickly grabbeded his wrists. “Hands on your head young man!” She commanded. With a sigh of defeat he complied, placing his hands on top of his head. He closed his eyes in humiliation, not able to meet her gaze.

Melissa felt a distinct warm and wet sensation between her legs as she admired his perfect physique. Below his eyebrows he was bereft of any hair. Not even a small crown of peach fuzz protected his modesty. His skin was fair and smooth without a single blemish. His small, pink scrotum hung tightly underneath his beautiful penis, which was about 2.5 inches flaccid.

Reaching out, Melissa grasped his miniscule package within her palm.

“Look at me Benjamin” she demanded in a soft, caring voice.

The boy forced himself to look into her eyes. She tightened her grip for a moment, eliciting a sharp intake of breath from the boy.

“Not much to brag about down here, is there Benjamin?”

“No mommy... sorry mommy” tears were welling up in his big puppy eyes.

“It’s okay baby. Don’t cry. There is another part of your body that I am much more interested in” She emphasized her intentions by sliding her fingers underneath his perineum, tickling his tightly contracted anus.

“Turn around so that I can get a good look at your precious little boypussy”

Clumsily he turned around, his feet constricted by the pyjama bottoms.

Benjamin’s humiliation was now accompanied by another unpleasant emotion, one of evaluative anxiousness. Would she approve of his bottom and “boypussy”? The poor boy had not the slightest clue, as to what features pleased this stunning valkyrie.

Melissa caught herself actually licking her lips as the boy’s perfect buttucks came into view.

“Bend over and touch your toes so that I can get a real good look at you” she said, in no way betraying her feelings of excitement.

The boy hurried to comply with her demand, grasping his feet with both hands.

This was a sight to behold, Melissa thought. His undeveloped testies and penies dangled between his legs. His soft yet firm asscheeks were spread open, and the tender little orifice inside his deep cleft came into view.

Melissa placed both hands upon his buttocks and stretched them even further apart. She reveled in the feel of his taut flesh. With her thumbs on either side of his anus, she stretched the skin as wide as possible, causing the tiny pink opening to gape open slightly. As the cool air of the room came into contact with his puckered rosebud it contracted in small spasms, winking seductively at Melissa. The fact that Benjamin, like all boys that age, was so self-conscious about his bum made the thrill all for the greater. The poor boy wanted nothing more than to cover his pale little fanny, yet he sought so desperately to please her, that he only mustered a weak whimper as she fondled and exposed him with complete disregard for his modesty.

“Mmmm. You’ve got the sweetest little boypussy I have ever seen Benjamin. And such a cute bottom too. I am very pleased with you”

Melissa was absolutely thrilled. His boyhole was so exquisite that she even felt the impulse to lick it. It took all of her willpower not to violate him right then and there, with one of the many toys from her bag.

Benjamin would have liked for the earth to swallow him. To have his most intimate place on his body exposed, at place that he had not even seen himself, was beyond humiliating. Yet the boy felt a peculiar sense of joy, that his bottom had pleased her.

“Alright. Stand up straight, and step out of your undergarments”

Melissa placed her hands on his hips to stabilise him while he clumsily lifted one foot, then the other. Melissa reached into her bag and took out a small dispenser labeled “anal lube” which she placed on the wooden table next to the armchair.

“You have been a very good boy so far Benjamin. I am so very proud of you. Now come sit on my lap”

Once seated, Melissa gave him a deep, loving kiss, invading his mouth with her tongue. The boy sighed with partial relief, knowing now that even though there was a future of degradation ahead, at least he had qualified on an anatomical level.

Placing her underarm beneath the back of his knees Melissa gently repositioned him, so that his back now reasted flatly against her thighs. Grasping both his ankles within her left hand she bend him over backwards with his knees on either side of his angelic face. He looked up at her with a confused, innocent expression. How adorable, Melissa thought.

In this sideways diaper position Benjamin’s bottom was raised, pointing skyward at the ceiling. Melissa picked up the lube and squeezed a small dollop of lube onto his quivering rosebud.

“Now Benjamin. I am going to tell you what our relationship is going to be like” She began, setting the dispenser back on the table. With her index finger she started to work the lube around his anus in tiny circles, eliciting pathetic moans from the frightened boy.

“You see Benjamin. You are not like most other boys. You are what we call a sissyboy. Do you know what that means?” she asked him in the softest, velvet like tone.

“No mommy” the boy whimpered in response.

“Well, most boys develop into grown muscular men, with big hairy penises, with which they can satisfy a woman. But some boys, like you Benjamin, will never reach puberty. They will forever have the body of a prepubescent girl with small hairless pee pees that will never satisfy any woman”

Tears were starting to well up in Benjamin’s eyes again upon hearing his doomed fate.

“Awww, don’t cry sweetie. There is a plus side to being a sissyboy. You see, instead of having an impressive manhood, you have a soft, tender little boypussy, that can satisfy those few women who like sissyboys, like me” She smiled benevolently down at him, while ever so gently applying pressure on his tightly shut orifice.

The boy sniffled quietly, taking some comfort in her words.

“But in order to satisfy a woman with your boypussy there is a few things that you need to learn. Boys your age are so focused on their little willys, but that focus needs to be shifted to your boypussy. There will be no handjobs, no blowjobs, no intercourse - ever! Just your tight little boyhole, my toys and lots of lube”

The tip of her index finger was slowly starting to penetrate his anus.

“Also, It is of the utmost importance that your bottom is always squeaky clean inside and out. But don’t worry too much about that. I’m going to help you out with a couple of daily enemas, and a thorough scrubbing, to make sure that your bum is always clean and flowery scented - ready to be used.”

She felt the tightness of his greased anus engulfing the first knuckle of her probing finger. A perverted thrill tingled up her spine - he was unbelievably tight!

“The key to satisfying a woman with your boypussy, Benjamin, is to relax your hole and give her complete access. I know it can be very difficult, especially with a tight virgin pussy like yours. Be a good boy and try to relax for me sweetie”

Benjamin drew a deep breath and tried to unclench his anus. He wanted so desperately to please Melissa. His efforts were awarded when suddenly his sphincter gave away.

Melissa smiled reassuringly down at him as she deftly sank the full length of her long and slender finger up into the boy's quivering hole.

“Oooops, there we go! Good boy!” Melissa cooed.

The inside of his bottom felt hot as his reflex action caused the velvety anal canal to clamp down around her embedded finger. "Uhhhhhh" the boy whimpered, his mouth agape, almost beside himself from the intense sensation as her finger roamed freely inside his sensitive insides.

“I guess this is the first time you have had anything up here, huh sweetie? You will get use to it soon enough. In fact, in time you will happily accepts whatever object I decide to introduce into your tight little bum”

She illustrated her point by slipping her finger deep into his quivering bottom. Her voice was rich and fruity with excitement as she gently stroked her cold-creamed finger in and out of the tight ring of his sphincter.

“You see, inside your bottom is this little sensitive lump called a prostate, and when I rub it like this...”

Melissa applied pressure his smooth prostate with expert dexterity. A skill she had acquired from her mother.

“Uhhhhhhhh!”

The poor boy was besides himself in a mixture of completely humiliation and ecstatic bodily sensation. His small penis had begun to engorge rapidly, now pulsating against the soft skin of his belly. Whenever she pressed down upon his sensitive organ, his member jumped in response. A shiny, thin thread of preejaculate fluid had formed between his urethra and pelvis.

Melissa felt a shiver of delight between her legs as she deftly pulled her finger out of the young boy's bottom, leaving it glistering and begging for more.

“I guess you liked that huh?” She ascertained padding his rigid member.

“Yes mommy. Thank you mommy” the boy answered obediently, now breathing heavily.

“You are very welcome baby boy. There will be much more of that, I can assure you” In her mind Melissa pictured mounting the boy from behind with her giant 9 inch strapon. She wondered if it would even be possible to fit her enormous cock inside his tiny ass. We will know soon enough, she thought to herself, smirking at her own deviancy.

Melissa was surprised at just how submissive the boy was. She was going to keep him, there was no doubts about it. He was the perfect playtoy in every manner. Although it would have been enjoyable with just a feeble show of resistance, so that she could have had an opportunity to spank him. Melissa decided on giving him a mild spanking, just to colour his cheeks a bit.

Without explaining herself Melissa flipped the boy onto his stomach. Trapping his stiff member between her tights, she positioned him to her liking.

"I think I better give you a taste of discipline to put you in the right state for mind for the evening”

“Yes mommy” Benjamin whimpered in a scared voice. He had never received a spanking before but he knew there was certainly a great deal of pain involved.

"Such a cute little behind - it’s just asking for a spanking" Melissa murmured to herself as her hands traveled all over his young bum. She smiled at the thought that his bottom would soon match the shade of his blushing face. Benjamin pushed out his bottom for her while keeping his eyes tightly shut in anticipation - what a darling!

Melissa took hold of his wrists and held them on the small of his back, rendering the boy completely helpless while she stroked and squeezed his naked backside.

She enjoyed the silence before the storm. Once in a while she would stop her fondling and lightly pat his upturned rump, feeling the boy stiffen in fear. Then suddenly, as if like thunder from a clear sky, her hand descended sharply on the upturned cheeks of his bottom, causing Benjamin to yelp out in pain. " Smack! smack! smack!" It sounded, as hard slaps rained down upon the woundable target before her. "Please mommy!" Benjamin wailed in desperation. "Smack! Smack! Smack! Smack!" The poor boy wriggled his bottom pathetically in an attempt to lessen the impact of her flat palm against his skin. "Smack! Smack! Smack!" For the next five minutes, all that could be heard in the large house was the sound of flesh against flesh as her hand unrelentingly roasted his poor backside. When Melissa was satisfied with the rosy-red color upon his burning cheeks, she suddenly stopped and ran her hands soothingly over his inflamed skin. "Shhhhh all done now sweetie," she said reassuringly, feeling a rush of sympathy as she saw the tears streaming down his blushing face.

Sitting him upright on her lap, Melissa pressed her lips to his, invading his mouth with her tongue. Benjamin sighed, his mouth open in rapture as she gave him a long, slobbery kiss. She broke of the kiss looked deeply into his eyes. The look of adoration and supplication was innocently displayed on his tearstained face.

Giving him another quick kiss on the forehead, she pressed his face against her maternal bossom.

“Such a good little boy you are. I am so very pleased with you”

Benjamin was led by hand upstairs towards the large bathroom at the end of the hall. His semi erect penis bobbed embarrassingly in front of him as they walked.

The cool porcelain tiles send shivers up through Benjamin's spine as he stepped into the bathroom. He was met by a feminine perfumed scent that for some reason made him feel even more vulnerable. This was his mother's bathroom. The sound of Melissa's footsteps echoed in the large room as her high heels trod across the shiny white tiled floor. She marched Benjamin into the middle of the bathroom. "Hands on your head Benjamin" Melissa said sternly, watching the boy obey immediately.

Scoring her nails gently across his back, she stepped around him towards the large brass tub and turned on the water. Turning back to look at him, Melissa found herself once again deeply stirred by the beauty of his slim body. Her eyes passed appreciatively from point to point, dwelling with the art of a connoisseur, first upon his slender torso and then down onto the straight smooth legs. His skin was so delicate, his frame so fragile.

Benjamin could not bring himself to meet her gaze as he stood naked with his hands placed upon his head. Melissa stepped towards him slowly, her hips moving sensually. Taking hold of the boy's chin she tilted his head backwards, noting his visibly blushing cheeks. Melissa looked down into his innocent eyes, savouring the moment. Benjamin felt so docile and feeble in her hands, like a puppet on a string. As she let go of him, his gaze immediately returned to his feet. Taking hold of a fluffy towel Melissa spread it down on the tiled floor. "On your back sweetie, arms over your head" Melissa told him nonchalantly as she busied herself at the sink. With a timid whimper Benjamin reluctantly lay down on the towel, feeling the soft fabric against his naked skin. The boy pressed his legs tightly together in a futile attempt at modesty, as he watched Melissa fill up a large, bright red enema bag. He could smell the strong rosy aroma coming from the soapy solution. Melissa ran her fingers over a variety of syringes, contemplating, while glancing over at the boy. She made sure the enema was very soapy and decided on using a rather large syringe.

Benjamin's face was a true picture of horror as he saw Melissa approach him, her hand smearing lubricant down the length of the nozzle as if it was a phallus.

"Please mommy" Benjamin pleaded with her in a inaudible voice, almost a whisper.

“Don’t you want to please mommy?” Melissa asked as she kneeled down at took hold of his slender ankles. Her face was that of an unrelenting and implacable queen as she towered over him.

“Yes, I do mommy” The boy whispered, as he felt his legs being lifted up into the air, elevating his bottom from the soft fluffy towel.

“Well then, mommy wants a nice clean boypussy” Melissa said in the most patronising, yet loving tone, as she exposed his body rudely, spreading the milky thighs wide apart. With her eyes fixed on the firm and trembling roundness of the boy's buttocks, she forced his knees down to his chest, then said:

"Now hug your knees tightly sweetie, and don't let go unless I tell you so,"

Melissa uttered a sigh of pleasure, at the boy was made to assume the ultimate of degrading positions for a young boy. She relished in the sight of this beautiful boy so submissively on display. With his handsome face blushing deeply and his eyes closed tightly, he looked absolutely adorable. Benjamin was hugging his knees as if his life depended on it, elevating the cheeks of his bottom, which were a nice shade of pink from the spanking she had just administered. His stiff member looked delicious as it rested on his pelvis. The smooth marbles beneath were drawn up tightly in his little pink scrotum.

Benjamin could feel the cool air around his smooth genitals and bumhole. With his stiff penis resting on the soft flesh of his stomach and his bottom pointing straight up towards her gaze, he could not think of a more humiliating position. Neither could Melissa - she was thrilled at the idea of his helplessness and her own power: her cleft had begun to grow deliciously moist.

In his 'knee to chest' position with his feet dangling in the air, Benjamin's rosebud sphincter seemed to be cringing as it peered up at Melissa. Melissa ran her hands over his exposed flesh, taking pleasure in the smooth feel of his pubescent body. "That's a good boy, now try and relax your little bum. This nozzle is alot bigger than my finger " She said with a smile and playful slap on his bum. She knelt down alongside the boy and brought the nozzle tip up to his quivering sphincter. Benjamin flinched and pulled back for a second. Melissa giggled and placed a hand on his shoulder.

"Where do you think you're going?" Melissa said with a wicked smile. Then she pressed the nozzle against his greased hole and pushed it in.

Benjamin whimpered as he felt it enter him. She slowly penetrated him as far as she could, his little anus being reluctantly forced to dilate around the shaft.

As Melissa released the water, Benjamin felt the hot soapy liquid gushing up inside him, invading his very core. Melissa laid the palm of her hand flat on his tummy and began to stroke in a circular motion. She made sure that her wrist smoothed over the tip of his penis as she caressed his flesh.

Pleasure fused through the boy's body, blending with the discomfort in his guts. Melissa could feel the hot fluid gathering in his stomach as she worked the nozzle stem to stimulate his prostate. A large drop of clear viscous liquid had again formed in the eye of his urethra. It descended in a gooey silver strand as it dropped onto his stomach. Melissa noted that half the content of the enema bag was already inside the boy.

"Please, It hurts!" the boy exclaimed.

"Shhh... just a little while longer.... be a good boy, you can take it all," she comforted him. Her fingers kneaded his stomach. His penis throbbed against the back of her hand. His balls were drawn up tightly against the root of his penis. The muscles around his anus were contracting frantically as he fought to stop his body from disgracing him.

As the bag finally emptied, she slipped the nozzle out and quickly replaced it with a pink Vaseline coated butt plug, that she stuffed unceremoniously inside his hole

“Uhhhhhh” the boy moaned at yet another invader stretched his poor anus.

"This is to prevent any leakage. You have to wait while it cleanses you. Just 5 minutes. Then you can let it out."

The minutes passed very slowly. Benjamin squirmed uncomfortably on the floor. It was like having to go in the worst way and not being able to. After what seemed an eternity, Melissa finally spoke.

"Alright Benjamin, I'm going to help you sit on the toilet so you can empty your little bottom”

Tottering to his feet Benjamin stood up with his belly visually distended. Opening the toilet lid carefully, Melissa positioned Benjamin's bottom on the cool seat.

Gripping the base of the the plug, she ever so slowly eased in out, pausing at the widest part of the toy, and then quickly withdrawing her arm.

The pressure was so overwhelming that Benjamin immediately expelled the contents of his tummy, feeling a great flood of soapy, flowery scented liquid gush out underneath him. Embarrassing farting noises echoed into the toilet as he helplessly evacuated his bowels. Benjamin shivered involuntarily and hung his head in shame. Melissa was enjoying herself immensely as she towered over the boy, arms crossed, with a superior smug on her face. She had him sit a few minutes, waiting for further spurts or dribbles.

The boy sat there hunched forward on his knees, a pure picture of shame. Placing her hand gently on his cheek, Melissa bent over slightly, looking into his blushing face, and said in a caring voice: "Now turn around and sit backwards on the toilet so I can wipe your little bottom"

Blushing a deep shade a red, Benjamin slowly got into position, barely able to believe how utterly humiliating this was. Melissa pressed down on his shoulders making him lean forward, resting his head on the cistern.

“Arch your back a bit more. That’s it. Stick out that little fanny of yours” Melissa instructed him, while meticulously folding four pieces of toilet paper.

Melissa smiled wickedly at her invention. All the flowery scented soap and water had left everything clean but she loved how it embarrassed the poor boy to have his bottom wiped like a small child.

“I purchased this ultra soft toilet paper for the occasion, see?” She waved the padded tissue in front of his face. “I’m going to take very good care of you delicate little boypussy” Melissa whispered into his ear before kissing his neck, sending goosebumps down his spine.

She brought her hand down between his cheeks and ever so gently pressed the soft material against his cleft, splitting his buttocks as she wiped it over his sensitive anus. Melissa examined the tissue and found nothing but wet soapy residue Melissa lovingly stroked his back as she repeated the procedure, again making Benjamin whimper as the tissue came into contact with his puckered opening.

“Do you like it when mommy wipes your little boypussy?” She asked tenderly, bringing her lips right next to his ear.

“Yes mommy. Thank you mommy” he answered weakly.

“That’s it. Just relax your little bottom while mommy wipes you. Nice and soft” she whispered into his ear "Only two more enemas to go now sweetie." Benjamin looked back at her in disbelief and horror, his lower lip trembling slightly. "Please mommy."

But nothing could bend the will of this valkyrie. It was a mere ten minutes later that the boy stood naked in the bathtub, feeling completely exhausted and literally drained after receiving three large enemas.

Melissa placed a stool next to the bathtub and sat down, uttering a satisfied sigh.

"Now doesn't it feel nice to know that you are sparkling clean inside your little bottom?"

The boy gave a weary, reluctant nod. Melissa took hold of his hips and spun him around, able to admire his body at her leisure. Benjamin was like a rag doll in her hands, too tired to protest as she proceeded to lather up his body with soap.

She worked over his arms, back and stomach before skipping down along his slender calves and up the inside of his thighs, occasionally scraping the sensitive flesh with her long manicured nails.

When she reached his mid-region, she pretended to only then notice the violent erection standing proudly a few inches from her face.

"Little boys never seem able to control themselves," she said while shaking her head in disbelief. Resting her left hand on his buttock for stabilization, she gently touched her index finger to the receptive slit of his helmet, making the boy's knees buckle slightly in response. Benjamin moaned softly as Melissa moved her foamy palm over the corona, sliding back his foreskin.

"No fuss now Benjamin,"

Melissa spun him around in the tub. "Such a silly boy you are. I Haven't even gotten to your little tush yet" Melissa punctuated her words by clutching one of his soft globes in each hand, digging in her long nails. Soaping up her hands generously, she commenced to deeply fondle every crack and cranny of his boyishly perky behind, while constantly whispering into his ear, purring to him how adorable she found his little bum to be.

Her fingers delved shamelessly into the deep crease of his bottom, locating his tiny spasming orifice. Benjamin closed his eyes tightly, as he felt the prying lioness behind him line up a long soapy finger.

"Now, be a good boy for me Benjamin... I want you to try and relax your little hiney - ooops there we go! That was easy" Melissa cooed triumphantly as her index finger slipped up into him with little resistance. An asphyxiated gasp escaped Benjamin's lips as she buried her finger to the knuckle, making the boy jump onto his toes.

"Stand still, Benjamin, or you will be going over my knees with that wet bottom of yours raised in the air... would you like that, mmm?"

"No, mommy" he replied, terrified, forcing himself to remain still while her fingers worked his tight pliant channel. Locating the sensitive flesh of his prostate, Melissa quickly withdrew her finger before adding a second digit, stretching his tight anus.

Benjamin moaned loudly, besides himself from the adept and unrelenting stimulation of his young body. With utmost dexterity Melissa teased the boy to fever pitch by rubbing her fingertip across his prostate in a zigzag motion.

She suddenly felt his prostate begin to harden. Sensing he was close to an orgasm she extracte her fingers in one smooth motion. "Clean as a whistle!" She ascertained with a sharp slap across his buttocks "Now sit down and soak in the water. I'll be back to wash your hair".

Melissa left to ready things in the bedroom and Benjamin eagerly hid his nakedness in the foamy water, savoring the feeling as his young body was enveloped into the temperate chasm. During the next few minutes in which she let him soak quietly, Benjamin almost forgot the shame of being reduced to a mere child in the hands of this goddess whom he called mommy.

Melissa soon returned to the bathroom. She poured a generous amount of shampoo into Benjamin's hair and spend a considerable amount of time lathering up his scalp with her long slender fingers. Her hands were caring as they traced through his hair, playing havoc with his feelings. His eyes were peacefully closed, his lips slightly parted.

Melissa smiled and gave him a kiss on the cheek as she manipulated his naive senses. "Such a good boy," she whispered as she massaged the back of his head. She could feel Benjamin start to relax in her gentle hands. Softly grasping his delicate neck, she placed her lips next to his ear, whispering: "Okay now, get onto your knees, bend over, and rinse your hair out in the tub. Be sure to keep your eyes closed."

Benjamin quickly obeyed her command, all too well aware that his bum was nicely on display as he did so.

"Get your head down in the water sweetie. Arch you back," Melissa said as she gently pushed down on the back of his neck, while admiring his wet and glistering behind. Benjamin descended his head fully into the water, giving her a perfect view of his bare bottom and the stiff member dangling between his thighs. Melissa had to stifle a giggle at the sight.

When Benjamin's hair had been rinsed properly, she raised the boy to his feet "Now for the cold rinse" Melissa announced while carefully helping Benjamin get out of the tub.

Placing him in the shower stall she quickly sprayed him down with icy water. The boy whined miserably as the freezing needles broke upon his skin. He desperately turned around as instructed, even bending over so that Melissa could spray directly unto his sensitive anus and the tight little sack beneath.

"Please mommy" the boy begged, tears starting to form in his eyes again. When she finally turned off the water, Benjamin looked like a sad wet puppy with his teeth chattering heavily. His erection had subsided and had curled up, looking even less impressive than usual and yet to Melissa, very cute. "Awww you poor thing," Melissa said as she hurriedly got him out of the stall and wrapped him in a soft fluffy towel. Melissa held Benjamin close as she rubbed his body through the towel.

"You have been a very good boy," she said, smiling down at him. Taking his head between her hands, she pressed her lips to Benjamin's, kissing him long and leisurely.

Melissa closed the toilet lid and sat down, pulling the boy in between her knees. "let's get you dried off" she said as she pulled the towel from Benjamin's shoulders, once again exposing his naked body to the cool air of the room. Benjamin felt utterly embarrassed and helpless as he stood before her like this, being dried off like a small child. Melissa carefully worked over his slender body with the towel, paying special attention to his genitals and the deep crease between his bubble cheeks.

When he was sufficiently dry, Melissa walked over to the sink and returned with a tube of body lotion. She smiled into his blushing face while squeezing a good amount of lotion into her hand.

"Hands on your head" she instructed Benjamin before bringing her creamy palms onto the soft skin of his pubis. Meticulously she coated his body in lotion, making sure to spread it evenly - although there was one particular part of his autonomy which received special attention. Having the boy turn around and grasp his ankles, Melissa generously applied the lotion onto his recently spanked behind which was still fairly pink in color. She even slipped a creamy finger inside his vulnerable bottom, making the boy whelp in response.

Needless to say, Melissa was enjoying herself immensely. The sheer control she was asserting over the boy had her pulse racing with excitement. When all the cream had been absorbed, she took Benjamin by the hand and led him into his mother’s bedroom. On the bed she had laid out the puericil creme solution in a wide jared container, the pink buttplug used previously, a large can of anal lube and a strap-on harness with a fat, realistic looking 9 inch rubber cock attached.

Melissa stepped out of her heels and began unbuttoning her jeans. Looking Benjamin straight in the eyes with a determined expression, she quickly pulled down her jeans and picked up the elaborate leather harness. In matter of seconds she was tugging the straps snug and tight around her hips.

Benjamin gulped hard, paralysed with fear as he looked at the massive battering ram protruding obscenely from her pelvis. It really did look like a real cock, with veins running down it’s shaft and a pair of rubber balls attached underneath.

“Wha... what are you going to do with that, mommy?” he quaked nervously, his voice cracking.

“I’m going to pop your cherry, Benjamin” she said nonchalantly in a soft tone, while arranging a pair of pillows on the edge of the bed.

“I want you to lay face down over these two pillows. Now”

Her words broke off his paralysis, and he quickly stumbled onto the bed and assumed the required position. He arched his back as much as possible, pressing his face and chest onto the bed. Melissa thought he looked adorable with his pink bottom pointing skyward and his legs spread apart.

While Benjamin struggled to adjust to her liking, Melissa placed a video recorder on the dresser right behind him.

“Now with both hands spread your cheeks as wide as you can”

With great pains Benjamin managed to hold the position while reaching behind himself and spreading his soft globes. Meanwhile Melissa made sure the camera had the perfect ankle and distance. This was diffidently a moment that needed to be captured on film: a prepubescent sissyboy loosing his virginity to a mostercock wielding amazon.

Leisurely Melissa strode up behind him, taking in the magnificent view of his widely spread boy ass. She undid the lid on the Puericil contained. Squeezing the rubber balls that were attached to the base, she buried the head into the jar and let go. A loud slurping sound could be heard as the dildo sucked up the white creamy substance, filling the rubber balls.

She pressed her hand in between the pillows and his pelvis and drew back his stiff member and delicate marbles out from between his legs, letting them rest on the pillow. Melissa drew a deep breath. She could hear the boy sobbing quietly in anxious anticipation.

"Shhhhhhhh. It's okay sweetie," she cooed while soothing her hands over his smooth pink flesh. "Now, be a good little boy and tell me; who does this adorable little boypussy belong to?" She gently scored her fingernail around the rim of his defenceless anus.

"You, mommy," the boy whimpered, still spreading his ass wide open for her pleasure. "Good boy." She grabbed the lubricant can next to her, and proceeded to pour generous amounts of clear thick liquid down the crease of his bottom.

Benjamin gasped as the cool substance trickled down his burning flesh. Likewise she thoroughly coated the huge veiny strap-on, making sure he would be able to take the entire length. Then she started to work in the lubricant around his sphincter, watching with fascination as the tiny pink star puckered up at her touch. "Uhhhhhhh" the boy gasped as Melissa popped first one, then two long fingers up inside him, overcoming his anus’ resistance with little effort required.

Fully embedded, she twisted her digits around a couple of times before retracting abruptly. Quickly she pressed the tip of the can against his anus and began squeezing its cool content directly inside the young boy's bowels.

"Uhhhhhhh, Ahhhh" the boy gasped helplessly at the invasion as Melissa emptied the entire lubricant container deep inside of him. Throwing the can aside, she positioned the dildo along the crease of his bottom, moving the bulbous head up and down between his firm young buttocks. The sweet pink opening of his anus puckered in anticipation and fear. The great strap-on dildo looked even bigger as it rested between the cheeks of his thirteen year old bum.

She leant over him and kissed his cheek while patting the underside of his small and sensitive genitals, which lay straining against the pillowcase.

"My, my, judging by your little friend here, I'd say you love being my little play-toy" She whispered teasingly into his ear before getting back into position.

Benjamin was sobbing uncontrollably by now but otherwise made no real attempt to try to escape. He fully recognized the complete superiority of his new babysitter and he knew he was going to get violated whether he liked it or not.

Having a vast amount of experience using a strap-on dildo, Melissa knew just where to position it and what angle to use. Lining up the dildo with his quivering virgin rosebud she pressed forward, watching closely as the little pink opening began to give away to the wide rubbery head.

"Uhhhhhhhh... please.... Ohhhh..." Benjamin moaned, beside himself, as his tiny orifice was stretched around the veiny impaler. Gradually his glistering hole began opening up more, almost nearing the edge of the strap-on helmet.

“Such a tight little boypussy you have” Melissa said throatily, her voice having become consumed with lust “Just relax baby. Let mommy inside”. Her clitoris ached from having been aroused for so long and his cries of vulnerability only excited her more

Keeping up a steady pressure, the rosy ring of muscle finally gave in, and with a rush of ecstasy, Melissa watched the blunt helmet pop up inside his velvety warm rectum.

“Uhhhhhhh... ohhhhh!” Benjamin cried out in anguish, as the fat, bulbous head of Melissa’s cock pushed past his defeated sphincter.

“Oooops! There we go sweetie pie” Melissa exclaimed triumphantly. She could not deny the delicious thrill she experienced, as she quickly followed up the phallus tip with a couple of thick greasy inches, feeding his poor little fanny unrelentingly.

“Uhhhh.. uhhh.. I’ts too big mommy!” the boy howled pathetically.

Pushing his hands aside, Melissa dug her nails into the warm soft mounds of his backside and spread his cheeks wide apart. She continued pressing forward, easing another couple of slippery inches inside him

Benjamin could do nothing but accept whatever length and size Melissa advanced on him. He felt his small penis throb violently against the pillow leaving thick droplets of pre-cum.

Slowly, Melissa pushed the massive shaft in deeper, inch by inch, taking her time with the helpless, squirming sissyboy. His little hole had never been stretched like this before, and he beat his fists on the bed as he cried out plaintively.

“Just a few inches more baby. Be a good boy and take all of mommy’s cock”

Melissa was both amazed and thrilled that she had been able to fit this much of her gargantuan tool inside of his slender frame. Her mom her once told her, that people differ quite a bit in regards to how straight their colon is, which is why some boys can take longer cocks than others. Melissa suspected that Benjamin’s had such a “prime colon”.

Determined to fit the entire length of her toy inside his prepubescent ass, she kept pushing down on him firmly, plunging it in deeper untill, at long last, she bottomed out.

“Uhhhhhh.... awwwwww” Benjamin cried out in defeat, as the monstrous schlong was buried to the hilt in his bowels. He felt impossibly full, like he was on the verge of being split in half.

"That's it, such a good little boy you are for mommy, and how perfect your sweet little boypussy looks wrapped around mommy's toy," Melissa purred. She spread his cheeks even more widely apart with both hands, crudely exposing the sight of his young bottom and the thick shaft penetrating its tight opening, and then began fucking him with slow rhythmic thrusts of her pelvis.

"Ohhhh uhhhhh." Benjamin moaned piteously and his young limbs went into small fits of spasms at the overwhelming stimulation. Gradually she began increasing the length of her thrusts, pulling out until only the fat, bulbous head remained, before slowly plunging back in again. Soon she was piling down on him with long, full plunges, working the entire dildo through his poor defenceless anus, forcing him to take every inch of the slippery silicone phallus.

Gripping his small ass tightly, Melissa pushed even harder, reveling in the wonderful sensation being transmitted to her dripping wet pussy. Melissa's clit throbbed with the sound of his squealing, Desperately gripping the blankets of the bed, Benjamin sobbed, grimacing with the dull pain of his back passage being so thoroughly violated.

Picking up the pace, Melissa gradually went faster and faster, plunging the massive shaft in and out as Benjamin wailed helplessly.

The sight of his pink rosebud wrapped tightly around the girth of her shaft had her going mad with lust "Such a good little boy you are" Melissa kept murmuring as she lovingly abused his round taut bottom. She had worked up a steady rhythm now, With each thrust she withdrew right until the head of the strap-on, before plummeting back in with a solid push, pressing her pelvis firmly against his sore behind and grinding the rubbery invader hard into his sensitive bowels.

“Uhhhhhhhh.... please mommy” The poor sissy squealed.

Back and forth. Again and again the glistering phallus slid along his pliant velvety canal. With each push the base of the dildo pressed on Melissa's clitoris, the sensitive organ stiff and aching. She angled her hips, altering the thrust to make the most of his delicious rectum, rocking her body to heighten her pleasure. Harder, and deeper Melissa used him, her hands squeezing tightly the soft flesh of his bottom.

For almost 30 minutes, the sharp sound of flesh against flesh filled the house, until finally, Melissa felt that familiar feeling building between her legs, and beginning to spread out through her body. Melissa threw her head back, and pushed hard forward, deeply in to Benjamin’s submissive body. She groaned in pure ecstasy, her clit throbbing, body clenching as she squeezed the the full rubber balls, filling his rectum with a large load of white creamy substance. .

The boy whimpered pathetically as he felt the cool puericil solution fill his insides, ensuring his perpetual prepubescent state.

As Melissa’s orgasm began to subside, she continued to stroke the dildo slowly in and out of Benjamin's sweet little opening. Benjamin lay completely motionless beneath her, sobbing quietly, desperately wanting to be free of her gargantuan, emasculating cock.

Tracing her index finger down the rim of his dilated anus, Melissa incased his testes in a firm possessive clutch.

"What do you say when mommy fills out your little bottom?" She asked, pulling gently on his tight sack

“Thank you mommy” the boy managed to whimper. Melissa had to contain herself not to laugh at his tireless devotion “You are very welcome sweetheart”.

Still spreading his cheeks wide apart, Melissa slowly eased the slippery battering ram out of his aching pink hole.

"PLOP!" it said, as the dildo left his slippery insides.

The boy was left with an odd sense of emptiness as his anus stood gaping up towards the ceiling. Melissa stood silently for a few seconds, admiring his obscenely gaping boyhole, glistening with lubricant. A mixture of lube and creamy goo was softly oozing out of his abused anus, dripling down onto his underdeveloped boycock.

She went over to the dresser and picked up the video recorder. Standing right behind the boy, she filmed his abused hole as it gradually began to regain it’s usual dot size. It was a truly mesmerising sight, Melissa thought.

Picking up the pink butt-plug, she positioned it against his open rosebud.

“You are to wear this buttplug all night. We don’t want any accidents, do we?”

“No mommy, uhhhhhh!” Benjamin moaned piteously as she slowly but forcefully pushed the fat, rubbery plug deep inside of him. His wellused sphincter offered little resistance and embraced the emasculating invader, quickly closing up around the narrow base and leaving him unable to expel it.

Removing her harness she lifted up the boy and sat him on her lap. "Such a good boy you were. You made mommy very proud" she purred while cradling him in her arms. She could feel his arousal pulsating against her body.

“From now on, you will be taking my cock everyday. Once in the morning, and once in the evening. That’s what a little sissyboy like you needs”

Benjamin’s body tensed in horror at her announcement and instinctively, his sphincter tightened protectively around the big rubbery butt plug stuffed inside of him. He began sobbing again, burrowing his face in her great bosom.

“Shhhhh... don’t cry sweetie. Soon having you bottom fucked will feel like the most natural thing in the world. Trust me” Melissa comforted him, softly rocking his small body. She sat with him like this for some time, cooeing and caressing his naked skin. Soon his crying subsided into sporatical sniffles. Despite having been so thoroughly violated, Benjamin felt safe and loved in her embrace. He thought about all the things she had said: the terms of their relationship and the nature of his constitution as a sissyboy. I his naive mind, it sort of made sense. And at that moment, as he pressed his tearstained face against her voluptuous breasts, he surrendered completely to her will. Whatever degrading, humiliating and even painful thing Melissa did to him, he would be a good boy for her.

Finally came his last humiliation of the evening: the diapering.

Laying him down on his back, Melissa grasped his ankles within her left hand and swung them unceremoniously up over his head, putting him in the most humiliating position. Smiling lovingly down at him, she placed a soft cloth diaper under his tilted rump.

“But I don’t need a diaper” Benjamin moaned in protest as she proceeded to liberally sprinkle his privates with talcum powder.

“You’re still a little boy who wets his bed Benjamin. In the daytime you can wear panties, but during the night you will be sleeping in diapers. And I don’t care if you manage to stay dry all night. Once a bedwetter, always a bedwetter.” She told him in a resolute manner, taking great pleasure in his embarrassment.

She let his legs down and pinned the sides snug around his hips with a couple safety pins.

“There we go. Plugged, powdered and diapered. Now my little prince is ready for bed” Melissa said pulling the durvet aside.

As Benjamin lay his head on the pillow, he was almost instantly drifting out of consciousness. Tugging him in, Melissa gave him a deep, loving kiss. “Sweet dreams my little sissyboy. We are going to have such a lovely weekend, you and I”

To be continued....

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