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Boy to Man

Prompt originally from AetherRoom.club
Created: 2021-08-08
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Description
A boy living in a sexually adventurous Japanese estate finally takes the plunge into adulthood with a woman he's had his eye on for quite a while.
Feel free to cut off and roll back the instant lewd starting point the prompt has to experience the slow burn. I'd recommend using OccultSage's Spicy Genroku module and Cross-Genre module found here: https://rentry.org/modules
Loosely based off the fabulous art made by Nakamura Regura.
https://gelbooru.com/index.php?page=post&s=view&id=6012033
Tags
japan, shota, femdom, smut, milf, japanese
Prompt
I've found myself so fearful of the — how'd you say — female attraction as of late. Naturally so, I find myself ridiculed by my peers whenever I let this fear come to light, as in all fairness, it is a rather silly aversion considering that I'm still a virgin. If I were to follow the standard codes of Ashina Estate, I would be encouraged to give away my virginity the moment my manhood could produce seed. There are some who think me a coward for not choosing to do so, and this I have grown comfortable with, but others have taken advantage of my inexperience. In particular, an older florist named Shippū, whose curvaceous and raven-haired beauty has admittedly transfixed my more innocent youth, has glanced at me in ways that can only be described as outright lascivious. Every morning she walks upon the jade paths that spiral across the estate, her face tranquil, and on first glance, rather unassuming, but the natural sashay of her boisterous hips, rolling seductively beneath the straining fabric of her kimono, reveals her true nature. Her every gesture and mannerism speaks of sexual desire, her gaze hungry, even predatory — as if the mere sight of me is enough to ignite her carnal fires. I am not without my charms, for better or for worse. I'm tall, despite my age, and appealingly slender, with soft features that most would simply describe as gentle, perhaps even too mild for the wilder side of Ashina culture. However, there is something about my demeanor that seems to invite the attention of those with darker appetites like Shippū. I feel compelled to walk carefully around her, to watch where I step, lest I tread upon the path of her temptations. I cannot help but wonder if her interest is purely intellectual, or if she is attracted to me in a way beyond the realm of reason. My heart pounds with excitement and trepidation as I imagine her eyes devouring me from head to toe, and I know I must make a decision soon, before my own passions overtake me. I am young, after all, and the time for such thoughts is yet to come. It's been a long week, and my patience is running thin. This evening, as I sit alone at the edge of the estate pond near my home, I have resolved to finally speak with Shippū. She has already given me ample opportunity to observe her behavior, and while I have tried to avoid her attentions as much as possible, I am growing tired of my shyness. It is a matter of time before she makes her move. Tonight, I will ask her out. My resolve solidifies as I see the shadowy silhouette of a familiarly voluptuous woman approaching along the winding pathway. Naturally, it was only a matter of time before Shippū caught wind of my presence. “Oh, you’re up so late, Sato,” she calls, stepping onto the stone path and coming to a stop beside me. Her voice is low, throaty, and warm, a mixture of sensuality and flirtation that does terrible things to my juvenile imagination. “Yes, well, I was just thinking of heading to bed early tonight,” I croak, hoping to mask my nervousness with an indifferent tone. “Unless, of course, you need something?” Shippū laughs, a deep, rich sound that makes the hair on the back of my neck stand up. “No, no, I was just passing by, and I thought we might talk. You don't mind, do you?” “Of course not,” I blurt out, “Please, join me.” I stand and turn, motioning to the small pavilion at the end of the path. The moonlight glints off the surface of the water, casting a silver sheen over the area, and the night breeze rustles through the trees that line the perimeter of the estate. It is quiet and serene, the perfect setting for our conversation. Shippū steps into the pavilion and takes a seat on one of the wooden benches that surround the center of the space. I take a place beside her, and then, unable to keep the excitement from my voice, I wonder aloud, “So, what did you want to talk about?” She gives a coy smile, one that I can only assume is meant to entice me. Her hand comes to rest on my knee, a simple gesture that sets my blood to boiling. “Nothing much, really. It's just that you're always so studious. I was wondering if you'd ever had a chance to explore your sexuality.” I blush, and try to cover my embarrassment with a cough. "Ah, I see. No, I have not. I mean, I've read many books about sexual practices and techniques, but I've never actually... ah, you know." Shippū's fingers squeeze my leg, making me stiffen in more ways than one. She leans forward, bringing her face closer to mine, and the novelties of her visage become increasingly clear. Her lips are soft, moist, and full, and the strong aroma of sweet cream and lilac is turning my gut to mush. Her dark, coquettish eyes bore into me as she offers, “Would you like to explore them with me?” "I-I'm not sure," I stammer, "that I am quite ready for such a thing. I have so much to learn, and . . ." “And you are afraid of being inadequate?” she interrupts, her voice low and sultry. “No, not exactly, but I do think that I am too inexperienced to be trusted with such a delicate matter. Besides, it would seem that you have your own needs that I'm not sure I could meet.” Shippū nods, her gaze steady and unnervingly confident. “How amiable of you, Sato. But, I have confidence in your abilities still. You are young, intellectual, and deserving of my attention. So, perhaps we could go somewhere else and delve into this matter further?” I swallow hard, trying to ignore the sudden throbbing between my legs as I consider Shippū's suggestion. “Well, if you insist, I suppose it would not hurt to see what you can teach me.” Her smile widens, and she rises from the bench, taking my hand in hers and leading me off the path. I am too distracted to notice the slight tremble that has taken hold of her fingers, or how her breath is coming in quick, shallow pants. We pass by the ponds that dot the estate, and I feel a strange yearning in my stomach as Shippū draws me close, her arm around my waist and her body pressed against mine. In a similar, mindless act of boldness, my hand finds its way to the swell of her buttocks, sinking into the soft flesh as if it were butter. When we come across her abode, Shippū pulls me inside and closes the sliding door behind us, and like a dog let out of its kennel, I eagerly follow her lead. She leads me to her bedroom — sparsely furnished with only a tatami mat, a dresser, and a few vases — and guides me onto the flat surface. As soon as I am supine, she climbs atop me, her large frame straddling my hips and her soft hands reaching down to cup my face.... [Click to expand]
I've found myself so fearful of the — how'd you say — female attraction as of late. Naturally so, I find myself ridiculed by my peers whenever I let this fear come to light, as in all fairness, it is a rather silly aversion considering that I'm still a virgin. If I were to follow the standard codes of Ashina Estate, I would be encouraged to give away my virginity the moment my manhood could produce seed. There are some who think me a coward for not choosing to do so, and this I have grown comfortable with, but others have taken advantage of my inexperience. In particular, an older florist named Shippū, whose curvaceous and raven-haired beauty has admittedly transfixed my more innocent youth, has glanced at me in ways that can only be described as outright lascivious.
Every morning she walks upon the jade paths that spiral across the estate, her face tranquil, and on first glance, rather unassuming, but the natural sashay of her boisterous hips, rolling seductively beneath the straining fabric of her kimono, reveals her true nature. Her every gesture and mannerism speaks of sexual desire, her gaze hungry, even predatory — as if the mere sight of me is enough to ignite her carnal fires.
I am not without my charms, for better or for worse. I'm tall, despite my age, and appealingly slender, with soft features that most would simply describe as gentle, perhaps even too mild for the wilder side of Ashina culture. However, there is something about my demeanor that seems to invite the attention of those with darker appetites like Shippū.
I feel compelled to walk carefully around her, to watch where I step, lest I tread upon the path of her temptations. I cannot help but wonder if her interest is purely intellectual, or if she is attracted to me in a way beyond the realm of reason. My heart pounds with excitement and trepidation as I imagine her eyes devouring me from head to toe, and I know I must make a decision soon, before my own passions overtake me. I am young, after all, and the time for such thoughts is yet to come.
It's been a long week, and my patience is running thin. This evening, as I sit alone at the edge of the estate pond near my home, I have resolved to finally speak with Shippū. She has already given me ample opportunity to observe her behavior, and while I have tried to avoid her attentions as much as possible, I am growing tired of my shyness. It is a matter of time before she makes her move. Tonight, I will ask her out.
My resolve solidifies as I see the shadowy silhouette of a familiarly voluptuous woman approaching along the winding pathway. Naturally, it was only a matter of time before Shippū caught wind of my presence.
“Oh, you’re up so late, Sato,” she calls, stepping onto the stone path and coming to a stop beside me. Her voice is low, throaty, and warm, a mixture of sensuality and flirtation that does terrible things to my juvenile imagination.
“Yes, well, I was just thinking of heading to bed early tonight,” I croak, hoping to mask my nervousness with an indifferent tone. “Unless, of course, you need something?”
Shippū laughs, a deep, rich sound that makes the hair on the back of my neck stand up. “No, no, I was just passing by, and I thought we might talk. You don't mind, do you?”
“Of course not,” I blurt out, “Please, join me.”
I stand and turn, motioning to the small pavilion at the end of the path. The moonlight glints off the surface of the water, casting a silver sheen over the area, and the night breeze rustles through the trees that line the perimeter of the estate. It is quiet and serene, the perfect setting for our conversation.
Shippū steps into the pavilion and takes a seat on one of the wooden benches that surround the center of the space. I take a place beside her, and then, unable to keep the excitement from my voice, I wonder aloud, “So, what did you want to talk about?”
She gives a coy smile, one that I can only assume is meant to entice me. Her hand comes to rest on my knee, a simple gesture that sets my blood to boiling.
“Nothing much, really. It's just that you're always so studious. I was wondering if you'd ever had a chance to explore your sexuality.”
I blush, and try to cover my embarrassment with a cough. "Ah, I see. No, I have not. I mean, I've read many books about sexual practices and techniques, but I've never actually... ah, you know."
Shippū's fingers squeeze my leg, making me stiffen in more ways than one. She leans forward, bringing her face closer to mine, and the novelties of her visage become increasingly clear. Her lips are soft, moist, and full, and the strong aroma of sweet cream and lilac is turning my gut to mush. Her dark, coquettish eyes bore into me as she offers, “Would you like to explore them with me?”
"I-I'm not sure," I stammer, "that I am quite ready for such a thing. I have so much to learn, and . . ."
“And you are afraid of being inadequate?” she interrupts, her voice low and sultry.
“No, not exactly, but I do think that I am too inexperienced to be trusted with such a delicate matter. Besides, it would seem that you have your own needs that I'm not sure I could meet.”
Shippū nods, her gaze steady and unnervingly confident. “How amiable of you, Sato. But, I have confidence in your abilities still. You are young, intellectual, and deserving of my attention. So, perhaps we could go somewhere else and delve into this matter further?”
I swallow hard, trying to ignore the sudden throbbing between my legs as I consider Shippū's suggestion. “Well, if you insist, I suppose it would not hurt to see what you can teach me.”
Her smile widens, and she rises from the bench, taking my hand in hers and leading me off the path. I am too distracted to notice the slight tremble that has taken hold of her fingers, or how her breath is coming in quick, shallow pants. We pass by the ponds that dot the estate, and I feel a strange yearning in my stomach as Shippū draws me close, her arm around my waist and her body pressed against mine. In a similar, mindless act of boldness, my hand finds its way to the swell of her buttocks, sinking into the soft flesh as if it were butter.
When we come across her abode, Shippū pulls me inside and closes the sliding door behind us, and like a dog let out of its kennel, I eagerly follow her lead. She leads me to her bedroom — sparsely furnished with only a tatami mat, a dresser, and a few vases — and guides me onto the flat surface. As soon as I am supine, she climbs atop me, her large frame straddling my hips and her soft hands reaching down to cup my face.
Memory
I am Sato, an admittedly self-conscious and nervous boy who has spent many of his days tempering his mind through education. Due to my servile and timid demeanor, the forward and sexually open environment of Ashina Estate under Lady Tōfufushi's rule makes my day-to-day life uncomfortable and filled with anxieties.
Despite being urged by my society, I am reluctant to give away my virginity and become an adult.
World Info
View World Info
  • Ashina, estate, Ashina Estate, Lady Tōfufushi

    The Ashina Estate, formerly plagued by great wars of conquest among its liege lords and their feuding sons, was now the stronghold for an entirely different kind of struggle. The men began to ail; their vigor sapped by constant battles with one another over land or power. It was then a certain woman came to power. A daimyo — one known for her beauty, wit, courage, and most bizarre tastes — turned the estate into a place of exotic, and in modern times, taboo pleasures.
  • Lady Tōfufushi, Sato, Shippū

    Lady Tōfufushi, using her noble prestige and courtesan-like diplomacy, forged the war-town Ashina Estate into a place of heretical love: where, for a fee, pleasure could be obtained without risk of harm or judgement. In her odd mind, war would not prosper in a realm where people had peace of mind and the sacred privilege to satiate their inner desires. She hired dozens of women as concubines, geisha, maids — from forlorn widows to fresh young peasant girls, they were all forced to provide sexual services, which Lady Tōfufushi viewed like a physician’s prescription. It was a necessary medicine to keep society healthy.
  • Sato, Shippū

    While it was a woman's duty to please, no matter their age or marital status, men followed a different protocol. The matured would spend their years naturally, doing their best to provide for their families and estate through humble business and farming. Young boys on the tender cusp of maturity, however, were cajoled, and sometimes forced, to make use of their fresh loins and spread their virile seed. It was Lady Tōfufushi's belief that that the youth's indulgence in the cloying pleasures of the flesh would raise them into tempered adults, and to make sure this vision was success, women who guided the adolescent from the virginal ways of childhood into the sensual bliss of adulthood were paid handsomely.
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