A Man Who Lost Confidence, to a Gentle Chastity-Reversed World

Chapter 101: A Second Union with Yukari-san ☆

“Ahh… haa… I’m so sorry… I can’t get up… my body feels so floaty…”

Lying on her side, Yukari-san spoke breathlessly, her gaze fixed on me. Her flushed cheeks and half-open mouth, an expression I hadn’t seen in a while, tempted me to think she was truly feeling it.

Her deep-breathing lover’s body, with her large peach-like hips pointed toward me and her sweet fluids seeping from her slit, captivated my gaze. Such an unguarded, erotic sight wasn’t something I deserved to witness.

“No, please don’t push yourself… It’s my fault you’re exhausted…”

I blurted this out as she tried to rise. I had no right to tell her not to strain herself.

She quickly denied, “N-No…!” and continued, flustered.

“You don’t need to think you tired me out! I’m the one who… received your penis, yet made you lick me for so long… I should be grateful, or rather, apologizing…!”

Her kind words prompted my hasty reply, “That’s not true… You licked me so much too…”

To me, our sixty-nine was a luxury I should pay a fortune for; her licking my penis was already extravagant.

Like Asagi-san, Maki-san, and Yuki, she didn’t recoil from my grotesque penis, eagerly taking it in. I could never get used to it, always succumbing to easy erections.

“…I willingly served your penis, Shun-sama. That’s my own selfishness…”

Staring at my half-erect post-climax penis, she murmured, “…Ah, Shun-sama’s…”

“Such a splendid penis, forgiving someone like me… Exciting it with my mouth is a miracle, yet… you even put your tongue in my vagina…”

Reaching toward her slit but pulling back, she looked at me.

“Even my shameless vagina… for you to be excited by it, Shun-sama… I’m so… happy…!”

Her softened expression and smile, warm yet lascivious with drooping eyes and flushed cheeks, overwhelmed me.

“N-No, Yukari-san, I’m…”

I wasn’t worthy of such a look. I should’ve denied it, but her eroticism consumed me.

Her breasts, prominent even clothed, and her shapely hips kept stirring my heart.

I couldn’t resist anymore. Despite her kindness and care, my lust was taking over, my penis regaining hardness.

“Ahh, your penis, Shun-sama… It’s getting big again… After releasing so much, it’s wonderful…♡”

My penis, hardening before her eyes, leaked a bit of semen despite her earlier efforts. Instead of judging, she called it wonderful.

My foolish erection reached full strength, craving release. I apologized, “Sorry, it won’t calm down…” but she shook her head.

“You’re excited, so there’s nothing to apologize for… But I’m the one who should apologize for expecting more…”

Sitting up on the bed, she continued.

“If you’re tired after ejaculating, I didn’t want to push you… But seeing your penis even harder now, um…”

Blushing but resolute, she confirmed with me.

“Of course, only if you’re okay with it… I want to serve you again. My vagina might be too wet and not feel good, but… I’ll try my best…!”

Her face lowered, her cute yet erotic demeanor undeniable. A mature beauty with girlish charm, I kept falling for her.

I wanted it too, trusting she’d forgive my boldness. I remained selfishly indulgent.

“Yes… I want to… put it in your vagina…!”

My request should’ve been laughable, but she exclaimed, “Oh, thank you…!” and slowly straddled my lower abdomen.

“Haa, Shun-sama… I’ll climb on, excuse me… I can’t make you strain…!”

Positioning her slit over my penis, she watched my face, lowering her hips.

“Y-Yukari-san, don’t push yourself, I can move…” I said, flustered, but she shook her head.

“It’s okay… I’ve rested… If you don’t mind, I want to serve you like this, is that alright…?”

Her vagina nearly touched my tip, pausing for my words. A slight lift of my hips would lead to insertion, my penis craving pleasure.

“…Yes, if you’re okay… together…” I replied, and she nodded. Our slit and tip kissed, my penis sinking in.

“Ahhh… Your penis, Shun-sama…♡”

Her drenched vagina enveloped my penis in pleasure. Without moving, just being inside her forced me to tense my lower body.

“Uuh, ah… it’s intense…” I groaned, easily grasping the pleasure-soaked sex beginning.

“Nn, haa… I’m so happy… It’s big, Shun-sama, so hard inside me… And you too…”

Looking down, her dreamy expression captivated me. A model-like beauty, my lover, shared such sweet sounds only with me.

“Looking down, receiving your penis… I shouldn’t, yet your erotic expression makes me selfishly excited…!”

She reached for her T-shirt’s hem but paused, gently touching my stomach to ask.

“Um… Shun-sama… Should I undress today…? If you don’t want to see, I can stay like this, but since you’re naked, it’s unfair if I’m clothed… I’m unsure…”

Even in pleasure, I felt guilty for her needless worry. Not wanting to see her body was impossible.

My blunt words might seem creepy, but with her accepting my penis, I couldn’t care about others’ judgments.

“…If you’re okay, I want to see all of you, Yukari-san…”

I feared she’d find my words cheesy, but I had no composure to refine them.

“…! Y-Yes… Thank you, excuse me…”

Her glossy eyes responded as she lifted her white T-shirt, revealing her large breasts in a white bra.

The slight cleavage enthralled me. Watching her undress during sex, my fluid-soaked penis hardened inside her.

“Ahh, Shun-sama… You’re looking… Uu, really, haa… it’s so hard…!”

Melting my penis, she unhooked her bra. “Haa, nn… it’s not coming off…” she muttered, struggling, but finally shed the last cloth.

“I’m not confident… but if you’re pleased, Shun-sama, I’ll do anything…”

With impossibly erotic words, she went fully nude atop my penis. Her plump breasts, pink tips erect as before, stood firm.

“…Look at me… Haa, my tips are hard… If you want to touch, if it’s not bad, you can, anytime…!”

Her breasts, offered forward, were within reach—an undeniable feast. I locked eyes with her lust-filled, unresisting expression.

“Shun… sama…” she moaned sweetly, not rejecting me.

I grabbed her trembling breasts, careful not to hurt, and began kneading.

“Haaa♡ Ah, yah, Shun-sama… It’s making my heart race…!”

Her exquisite feel melted my heart. Her reddening, refined face made me think she enjoyed my touch.

I shouldn’t get carried away, but my pleasure-soaked penis was drenched in her fluids. My mind couldn’t stay clear.

“Y-Yukari-san… Inside feels so good… Your breasts are soft and erotic…!”

With honest words, I touched her erect pink nipples. I shouldn’t touch such a place, but I wanted to please her.

Pinching her soft yet firm nipples gently, she cried, “Hyauu♡” and straightened.

“Ah, haa… Your fingers… Nn, yah! I-I’m gonna… Haa, no…!”

Beyond her soft fluids, her rippling folds stimulated my penis, as if pulling my semen out.

Even in this slow sex, her vagina overwhelmed me. “Uuh, ah…” My creepy moans escaped despite restraint.

“Haa, Shun… sama… My nipples, sorry, yah… My breasts are weak…”

I gripped her breasts, supporting her body, like an erotic manga scene, yet undeniably real, drawing semen to my penis.

Moaning and breathing, she entrusted herself to me, subtly grinding.

But she murmured, “No, I can’t…” and slowly rose, hands on my stomach, breasts exposed, moaning sweetly, “Haa, ahh…”

“I’m so sorry… I can’t move well… Your touch feels too good, I’m weak… I should make you feel good, but… please, just wait a bit…”

Her apologetic words, head bowed, felt erotic. Her sincere pleasure overwhelmed me.

I had to ease her anxiety. This was her second time, likely uncertain, yet I’d only relied on her.

I needed to move for her.

“W-Wait! I’ll move! Just lie down, in a comfortable position…!”

To my sudden words, she said, “T-That’s… I’m sorry for you, Shun-sama…” but she shouldn’t feel that way. I wanted her to use me to feel good.

My penis, still in her melting vagina, felt her soft folds and fluids. My urge to ejaculate was high, likely obvious to her.

“I want you to feel good, Yukari-san… I want us to feel good together… as lovers, in your vagina…!”

Drowning in her kindness wasn’t allowed, nor was letting her strain. Calling us lovers was my selfishness.

Despite my bold declaration, she, still straddling, moaned, “…Uu, Shun-sama… Haa, saying that… Nn, ahhh…!” trembling.

“I’m sorry… Your words made my heart race… I came a little…”

Her glossy eyes reported erotically, then, “Thank you…” as she met my gaze.

“If you say that… Staying on top might be heavy, so I’ll indulge again, please…!”

“It’s not heavy… but I’ll take over…” I replied. Her moving for my pleasure was wrong; I was always a step late.

“Yes…” she said, exhaling, slowly lifting her hips.

Her fluid-soaked penis glistened, asserting her wetness. She looked away, embarrassed, but saw my rigid erection.

“Haa… I’ll lie down… I’m sorry…!”

Crawling, she adjusted the pillow and lay down, spreading her long legs toward me.

“Shun-sama… Again, but… I’d be happy if you felt good inside me… Please…!”

Watching me, she shyly spread her slit slightly with her right hand. Her anxious upward glance fueled my desire.

Her beautiful pink folds, their deepest sensation lingering in my penis, begged to be tasted again.

I knew not to hurt or rush her. Holding my penis, I approached.

“Shun… sama…♡”

Her sweet voice made me want to release instantly, but as her lover, I met her gaze, aligning my tip with her slit.

“Ahh, hauu… This might be too much… It’s still so wet… You’re entering again…!”

Her erotic voice risked my premature release, but I held back, sinking my penis into her drenched vagina again.

Chapter 102: The Sound of Fluids and Mutual Climax ☆

“Ahh, no… hauu! Shun-sama… hyau, nnn, I’m… coming…! It feels too good… ahn…♡”

In Yukari-san’s simple bedroom, she moaned on the bed. Despite the air conditioning, sweat glistened on her trembling breasts.

Her uninhibited state left me unable to suppress my excitement. Breathing heavily, I thrust my penis, careful not to hurt her, though her enveloping movements seemed to thwart my restraint.

“Ugh, ahh, Shun-sama… nn, ngu…” she said, occasionally tensing, her gaze on me. Pierced by her sharp, now dreamy eyes, I paused my hips.

Fearing I’d done something wrong, my penis trembled slightly. As if responding, Yukari-san’s body shuddered.

“Haa, ah… It’s rubbing the good spot… No, I’m sorry, it feels so good… auu…”

Her vagina, swallowing my tip and shaft, stimulated me with fluids and flesh, making me feel forgiven. Her half-open mouth and enraptured expression seemed to revel in my actions.

I was overrated, merely excited by her eroticism, with little room to consider if I was pleasing her. My penis, driven by sensation, resumed moving.

“Uuh, s-sorry…” I muttered, indulging in her allure—not just her drenched vagina, but her E-cup bowl-shaped breasts, their erect pink tips, the softness of her thighs I gripped, and her captivating expression, stealing my composure.

“Haa, Y-Yukari-san… It feels so good… uuh…”

My honest feelings spilled out. My expression was likely pathetic, my penis relentlessly pooling semen.

But I had to ensure she wasn’t in pain or that I wasn’t selfish, reading her face. It was late, but I couldn’t shake that thought.

Staring at a woman was hard, and believing she’d enjoy my gaze was arrogant. Yet, during my clumsy thrusts, I tried to meet her eyes.

“Ahh, haa, yah, hyauu…♡ Being… looked at like that makes my heart race… auu…”

Normally, my stare would be a punishment, but her vagina writhed, her high-pitched moans echoing.

Noticing something, she said, “Ah, Shun-sama…”

“I… I’m feeling too good… I must look awful… I’m afraid you’ll find me unpleasant…”

Covering her flushed cheeks, her action felt erotic, making my penis quiver inside her.

Far from finding her gaze unpleasant, her worry that I might was unnecessary—she was too kind a goddess.

I had to dispel that.

“No way your face could be awful… I’m happy you’re feeling good… So, Yukari-san…”

Pausing my thrusts, my emotions surged.

My words might be presumptuous, and their timing uncertain, but with no time or restraint left, I let them flow.

“Yukari-san… Haa… You’re so erotic and captivating, too much for someone like me… You’re always an irresistibly beautiful woman…!”

Believing I mustn’t look away, I gazed at her face.

Her sharp, glossy eyes, flawless skin, small lips I’d tasted and that had taken my penis—all proved her beauty, shaking my heart with her allowance of me.

“You’re always with me… Kind, yet so erotic… I… I love you so much…!”

My emotions overflowed like a broken dam. Loving her despite my other relationships, with no certainty she’d welcome it, my circuits burned with her pleasure and my affection.

She blinked repeatedly.

Fearing I’d troubled her, her words followed.

“Eh, ahh… Saying you love me… No…!”

Her vagina tightened, gripping my penis. The sudden sensation forced me to tense, holding back ejaculation.

“I can’t… hold back… nn, ah, ngu, fuu, nnn…!”

Her body shook, her lips pursed as if enduring something. With a soft, “Nn, uu, fuu…” she looked at me, teary-eyed, pleading.

“…Shun-sama, I’m sorry… Like before… I’m so happy, I feel that same sensation… I might squirt again… I can’t hold back, so please, pull out… It’s dirty…!”

Recalling her first time, when she, a virgin, squirted clear fluid for me, I knew I’d never find it dirty. My lust remained unchanged.

“…Don’t hold back, Yukari-san…”

Making her apologize for feeling good was unthinkable. As she began, “N-No, I…” I pressed on.

“There’s nothing dirty about your body… If you’re okay, I want you to let go and feel good…!”

My excitement at her squirting might be selfish, and if she disliked it, that was an issue. But if it was for my sake, I wanted her to cast that aside.

My hips moved slightly, advancing in her vagina. Unable to hold back, she moaned, “Hyau…♡” and gazed at me.

“Haa… I’d never dislike it… Really, if you forgive me… I’m going to feel good again…!”

Caught between anxiety and pleasure, her expression, gripping the sheets, was captivating.

“…If you forgive me, I want to feel good too…!”

Pushing my selfish desire, something I shouldn’t be allowed, she murmured, “Ah, your penis is moving…” and spoke.

“Uu… Your words overwrite my common sense… I’m scared you’ll hate me, but if you want it…!”

“If you think it’s dirty, you can pull out… But if you thrust deep again… I’d be happy…!”

Her lustful expression, tinged with a smile, accepted my proposal. Her eroticism and kindness made my hips forget to stop.

The slap-slap of flesh, the sensation of stirring her vagina, made our sex vivid.

Her moans excited my ears further.

“Hya, hyau, ah, ahh…! It feels good… No, I’m coming… I can’t… Haa, ah, uu, ahhh…♡”

With her loudest cry, her body convulsed, a splash echoing as warm, clear fluid sprayed my stomach repeatedly.

“Sorry, Shun-sama… I can’t hold back, it’s all coming out… hauu…! Your penis… moving…♡ Yah…♡ Inside’s twitching… My head’s breaking… Haa, ahh…♡”

Her, an older beauty, squirting for my penis fueled my desire. Drowning in her fluids, my penis was at its breaking point.

“Uuh, Yukari-san… I’m gonna come, I’m close…!”

Thrusting clumsily, I groaned. She turned her glossy eyes to me.

“Haa, y-yes…♡ Anytime’s okay… Yah, still coming… Like this… Haa, nn…!”

Squirting slightly, trembling, she spoke breathlessly, encouraging me.

Without pretense, her kindness and eroticism left my penis unable to hold back a second longer.

Truly, not a second. I should’ve asked to come inside, but my restraint failed, my tip opening.

A single spurt came, and unable to resist, I released all my semen.

“I’m coming… Inside, sorry… Uuh…!”

I shouldn’t carelessly come inside such a captivating older lover, yet I poured thick white fluid into her depths. Forgetting to pull out mid-ejaculation, her drenched vagina made me utterly foolish.

“Ahhh…! It’s coming, Shun-sama… I’m… coming again… hyauu…♡”

Instead of rejecting me, she accepted it, spraying clear fluid over our joined parts.

Climaxing together, my mind couldn’t keep up. My penis, endlessly producing semen, occupied her vagina too long.

“Shun… sama… Ah, uu, I’m… done… It feels too good… ahh…♡”

As my ejaculation ended, she released a final, longer spray. Her erotic fluids soaked my abdomen as she stretched her legs, collapsing.

Her vagina, indulging my penis, gently milked my semen, not forcefully but kindly.

As my penis slipped out, she gasped, “Ah, your… semen…” Her twitching slit oozed white, proof of my reckless climax—a luxurious sight.

“…Ah, so much inside, Shun-sama… In my vagina… ahh…”

Stroking her groin, her words made my penis twitch, my gaze turning lustful toward her naked body.

※

For a while, Yukari-san lay catching her breath, while I sat on the bed. Exhausted from ejaculation, my fatigue paled compared to hers.

Recovering somewhat, she sat up, immediately apologizing with hands on the bed.

“…I’m so sorry… I was forceful and even… squirted on you again…!”

A naked woman nearly prostrating on the bed felt surreal.

“No, don’t worry! It was my fault…!”

She shouldn’t apologize; I was the forceful one.

“…I got excited and wanted you to feel good…”

I could no longer hide my dirty lust from her.

“…I wanted you to feel good, and… I wanted to see your erotic side. If it wasn’t the sex you wanted, I’m sorry…”

I should’ve made it perfect for her, but my pleasure often took priority, despite her choosing my penis.

“…! Shun-sama… With you, any sex feels heavenly… I know it’s wrong, but when you thrust while I squirted, it felt insanely good… You don’t need to apologize…!”

Her words were reassuring. Normally, my forcing her to squirt would be criminal, even in this reversed world, and I couldn’t shed that sense.

But her feelings didn’t lean that way.

“Uu… But choosing me, yet always making a mess… Even if you forgive me, I should hold back. As the older one, am I really okay with these mistakes…?”

I had to answer her doubt repeatedly.

“I… I shouldn’t say, but seeing your erotic side excites me so much… I’m the one who should ask if it’s okay, since you chose me…!”

She was far too captivating for me. Her devoted service was something only high-spec men in my old world could receive.

Wanting sweet sex with her, to make her feel good, I was already too indulgent.

“I could never choose anyone but you, Shun-sama… A kind man who talks a lot and enjoys sexual things doesn’t exist elsewhere…!”

Choosing her words, she continued.

“…It may be rude, but you underestimate yourself, or worry too much… But at least to me, as long as you allow it, I adore you always…!”

Finishing, she pressed three fingers to the bed.

“Yet I keep pushing myself on you… If you’re willing, can I remain your lover…?”

She treated being my lover like a precious right, slowly bowing.

“Of course…!”

My shout surprised even me.

“You don’t need to bow, Yukari-san! I’m the one who needs to work to stay your lover… You even said we’d spend your birthday together…!”

Her early September birthday, where we’d promised to spend time together, was a miracle. A birthday date with her would’ve seemed like a prank in my old world.

But the promise was real, and she affirmed, “Ah, y-yes…!” straightening.

“I still think a birthday date with you is a dream… But hearing you say that makes me so happy…!”

Blushing and fidgeting, she seemed adorably youthful despite being older. I was the one who should think it a dream, needing her forgiveness.

“That you’d give me such an important day makes me happy… So, once again, please…!”

I might’ve repeated myself, my communication far from smooth.

Her body tensed slightly, arms crossing her stomach, emphasizing her full breasts and stunning figure unintentionally.

I found her erotic, but I knew I should meet her gaze, despite my cowardice.

“Yes…!” she said, voice high, reaching for me.

“As your lover, I’ll do my best… Uu…”

Her soft left hand, slightly sweaty, overlapped mine, conveying her warmth.

※

Our hands stayed joined, her dreamy gaze fixed on them.

Her beautiful yet naked form left me unsure where to look. My semen spent, my penis retained a half-hard state.

“…Ah! I’m sorry, leaving you naked… And wet…!”

Minutes later, she panicked, nearly bowing again. Perhaps noticing my gaze, she grabbed tissues from the desk.

“You should shower, but first, let me wipe you a bit…”

I offered to clean myself, but she insisted, “No, I made the mess, let me…!” and I nodded.

I should’ve insisted, as letting her clean was arrogant, like a king.

Yet she gently wiped my lower abdomen, making me feel guilty. She even eyed my fluid-soaked penis.

“Uuu…”

Her stare sparked shallow, lustful hopes. Shaking her head, she asked, “…Can I wipe this too…?”

Nodding, she took more tissues, carefully cleaning my tip, shaft, and balls. I worried it was humiliating, but she did it earnestly.

Though not sex, the faintly erotic moment ended our encounter. An hour had passed since Yuki left.

“…Shun-sama, I should wash it off, but… I don’t want to tire you again…”

Her urging me to shower made my heart race. She’d use it after, so I quickly washed, her warmth lingering.

Her breasts’ feel, her vagina’s sensation—vivid post-sex excitement filled this world.

※

After showering, I sat on the living room sofa while Yukari-san prepared dinner.

I offered to help, feeling I’d overworked her, but she insisted, “You need to rest, Shun-sama!” bustling about.

Her occasional thigh-rubbing or glances at me tempted wishful thinking, but I shouldn’t indulge or stare.

Soon, Yuki and Mom returned, joining us in the living room after changing.

Yuki’s whispered, “…Yukari-neechan looks happy…” startled me, and Yukari-san seemed aware of her gaze.

But aside from that, the warm, familiar atmosphere of our four-person dinner began as usual.

Chapter 103: As a Housekeeper, As a Lover

Yukari-san’s Perspective

※

Shun-sama informed me he’d finished showering and headed to the living room alone. I slowly walked toward the bathroom.

Or rather, I had no choice but to walk slowly. The intense sensation of Shun-sama’s penis lingered in my lower abdomen, and I feared his semen might drip out.

Walking was difficult, but it was a deeply comforting reality. That Shun-sama reached endless climax inside my vagina—how could I possibly complain of exhaustion?

Beyond this hallway, in the living room, is Shun-sama, who shared a second time of sex with someone like me. Just thinking of it makes my vagina ache; my body is already dependent on him.

※

Taking a quick shower, I sat and picked up the body soap, rubbing my arms as usual. But my heart was far from calm, my mind filled with memories of our recent sex.

“…Shun-sama…”

My faint murmur echoed in the bathroom. I nearly reached for my semen-filled womanhood, but touching it might lead to self-indulgence, which I must avoid.

The womanhood I thought I’d never use now wets just thinking of Shun-sama and his splendid penis, transformed into an insatiable vagina.

But that’s an overwhelmingly happy truth. To be in such a situation feels like a miracle.

※

“…Haa…”

With a small sigh, I stopped rubbing my arms, my thoughts drifting to the past.

Three years ago, after earning my housekeeper certification and graduating university, I contracted with Kaori-sama and this household. Kaori-sama chose me from a housekeeper information site.

“I talked with a few girls, but you seemed the most honest and kind,” she said. Kaori-sama is nothing less than my benefactor. Not all registered housekeepers are hired consistently, and I’d considered other jobs.

A household with a man would have astronomical competition if publicly posted.

But I only learned of Shun-sama, a young man, when I met Kaori-sama. I didn’t become a housekeeper to get close to men; I simply loved cooking and housework, wanting to do it for others.

So, being hired was thrilling but also daunting. I’d barely spoken to men, let alone dated. I wasn’t uninterested in erotic matters, but…

Even at university, few girls interacted frequently with men. Lacking assertiveness, I never imagined working in a house with a young man.

※

Kaori-sama, the mother, treated me like family, with few of the strict rules typical for housekeepers. Yuki-sama, the eldest daughter, was bright and charming, accepting me openly.

But Shun-sama, as Kaori-sama noted, was distant with women.

He was less so with Kaori-sama, but he rarely spoke with Yuki-sama, who actively approached him, or with me, a sudden presence.

Minimal conversation, an air of constant worry—he seemed typical of young men who shun women’s gazes, retreating to male-only spaces.

Yet, he showed no clear hostility toward women. So, I hoped we might eventually talk a little, though I hadn’t thought of how to make that happen.

※

Everything changed when Shun-sama entered high school. I still remember that spring day when I went to wake him in his room.

Until then, his replies were brief—“Yes” or “Understood”—and I was grateful for even those. But he began communicating with me, Kaori-sama, and Yuki-sama, albeit nervously.

Perhaps a change of heart? He seemed like a different person, and I was a bit confused, though undeniably delighted.

But Shun-sama became very unguarded. He’d start changing in my presence or blush when our eyes met—actions that could easily be misinterpreted.

For a lifelong virgin like me, it was a flurry of excitement. I knew I had to restrain myself, but various emotions began swirling.

※

“…That time, right?”

I only held back for a few days. My swirling emotions exploded in the worst way.

I tripped and fell with Shun-sama, pressing my body against his. I blurted out that I’d handle his erect penis. Ultimately, in my excitement, I took his precious penis in my mouth.

Normally, I’d be arrested. Yet, Shun-sama, as if he were at fault, forgave my selfish actions entirely.

At that moment, my senses began to crumble, and I started seeing him as a sexual object.

Of course, I’d never initiate, but I likely cast lustful glances at him. I was an utterly failed housekeeper.

However, as a housekeeper, I began to realize the need to support Shun-sama’s heart. It was presumptuous of me, but I couldn’t bear his unnecessary self-deprecation.

“I’m boring to talk to,” he’d worry. That’s nonsense—his conversations with Sasai-san and Yamamoto-san bring smiles, so he has no need for humility.

Clumsily, I hugged him to convey that. I was desperate then, but looking back, it wasn’t something a non-lover should do.

Yet, Shun-sama accepted me, showering me with gratitude.

※

“…Overstepping.”

Yes, my actions were overstepping, but that moment, I might have developed strong feelings for him.

Lacking the assertiveness to talk to men, believing I’d never have such a connection, Shun-sama overturned all that, even trusting me.

Still, I knew our age gap made a romantic relationship a fantasy. So, I resolved to work as a housekeeper, helping him as long as needed.

Hearing he’d become lovers with Sasai-san and Yamamoto-san, I was genuinely happy for his joy. His lack of loneliness was paramount, always.

※

However, Kaori-sama and Yuki-sama saw through my feelings. Through Yuki-sama’s suggestion, Shun-sama and I went on a date, leading to a whirlwind of events.

Kaori-sama and Yuki-sama understood his changes and supported us—an indescribable kindness. Normally, I’d be cast out of this house.

On the date, we rode attractions, held hands unconsciously, took photos together, and I absorbed his overflowing emotions.

A dreamlike, precious day passed, and I was constantly flustered by him listening to my trivial talk. I worried my emotions showed, but I held on until night.

※

Yes, until night. At the last moment, I made an overly blunt, shameful confession to him.

Despite my lustful nature and impermissible feelings, he accepted everything. I’m amazed I didn’t crash on the way home; my mind was in chaos.

The miracle of being his lover, the tension of what I’d do, the fear of messing up—all swirled together.

※

In the end, I squirted from his penis—an utterly shameless act. The brief pain of losing my virginity gave way to drowning in pleasure, my lust running wild.

“…Squirting’s become a habit, hasn’t it…”

Not just the first time, but today, my second time, I squirted profusely, soiling him. Warning him beforehand was slightly better, but two consecutive “leaks” prove my vagina’s hopelessness.

Yet, he called my body erotic, thrusting repeatedly for someone like me.

He kneaded my breasts, teased my hardened nipples—services I don’t deserve.

Unable to resist his penis, he allowed me to lick it, like an ideal man from a manga.

As the older one, I’ve never led him, only drowning in his penis hitting my sweet spots. His servicing my breasts, hips, and vagina leaves me no composure.

How do Sasai-san and Yamamoto-san, who’ve had sex with him repeatedly, endure this pleasure? Or do they excite him further? I wish they’d guide me via messages.

※

Shun-sama is kind, which makes him worry about making others happy. But his kindness makes me, at least, insanely happy. Every conversation is a treasure.

Sex with him surpasses any masturbation; my vagina might break someday. If he desires, I want him to thrust endlessly, even roughly—it doesn’t matter.

But he likely considers me, avoiding roughness. His lustful thrusts carry a kindness I feel within the pleasure.

※

Shun-sama has relationships with Sasai-san, Yamamoto-san, and Yuki-sama. He seems friendly with several girls from his club or class.

Whether it’s his or their assertiveness, his fulfilled heart is what matters most.

But if a woman forces herself on him against his will, I must intervene. If he chooses sex, I’d never interfere out of possessiveness—that’s unthinkable.

※

As long as he doesn’t abandon me, I’ll devote everything to him. To betray the man who gives me endless excitement and peace, who I thought I’d never connect with, is impossible, even in death.

…Saying “in death” might burden him. Since he accepts me as a lover, I mustn’t be a weight.

Will I ever lead him as an older lover? But with him likely having sex with many women, my weak vagina will keep climaxing from his penis.

※

“…Such indulgent thoughts.”

I’m indulging in wanting to experience his penis repeatedly—something I shouldn’t easily desire.

But he said we’d date, sparking expectations. A birthday with erotic moments—how happy that would be.

No, just being with him makes me happy. That’s absolutely certain.

If he desires my body, I must respond fully, no matter what. My oversensitive breasts, fleshy hips, and shamelessly dripping vagina—all are for him.

But most importantly, his heart must be fulfilled. If I can be one piece of that, I’d feel boundless joy.

※

“…I adore you.”

Murmuring what I told him, I turned off the shower and left the bathroom. For Kaori-sama and Yuki-sama, I should focus on the housework I’ve neglected today.

Still, the lingering sensation in my lower abdomen recalls his captivating form. I love him so much, uncontrollably.

Feelings I shouldn’t have had are affirmed by him, melting my heart. Kaori-sama and Yuki-sama’s acceptance envelops me.

※

Shun-sama, Kaori-sama, Yuki-sama.

I, Yukari Nishikawa, am happy.

If I’m allowed to savor this happiness, that’s what I wish.

Chapter 104: Planning a Family Trip

“So, there was something delivered today, wasn’t there?”

After Yukari-san’s delicious dinner, Mom brought it up. As the three of us looked at her, she went to the living room to fetch something.

The envelope she brought back looked like airmail, likely from overseas, if it matched my old world’s image.

“Oh, could it be from Grandma?!” Yuki exclaimed gleefully.

Mom nodded, confirming Yuki’s guess. Seeing Yuki’s sparkling eyes, I realized this was my first time learning about my grandmother.

※

Until now, I’d lived without any information about relatives, including grandparents. Asking might raise suspicions about why I didn’t know, so I waited for Mom to bring it up. My lack of initiative played a part, too.

“Where’s it from this time?” Yuki said, pulling a letter and photos from the opened envelope.

She must have a friendly relationship with Grandma. Mom sighed softly, watching her.

“My mother… Grandma still only sends the bare minimum in reply to our emails, but she makes up for it with these handwritten letters,” Mom said.

Grandma might be living abroad long-term, I imagined. Yuki, nodding along, read the handwritten letter.

“Wow, Grandma’s living in Egypt now? Back in February, she was in South America, farming near a jungle village, right?”

I thought I misheard, but Yuki showed me the photos. A woman in her sixties, resembling Mom, smiled happily with locals.

“Didn’t she write before about nearly crossing Russia by train?” Mom said, sounding exasperated but not upset. “She never comes back. She seems happy, so I guess that’s fine.”

“Yukari-chan came around the time Grandma left on her travels… three years ago?” Mom added.

“Y-Yes,” Yukari-san replied. “I met Shiomi-sama for about a week when I started working here, but that was it.”

The name Shiomi, written in kanji, came from the letter’s signature. It mentioned her enjoying Egypt, reading Mom’s emails, and even asking about me.

“When I told her you’ve changed because of girls, she said she might come back to see for herself,” Mom said. “You used to talk with her a bit, didn’t you, Shun-kun?”

So, Grandma’s traveling but could return if she wanted, and our relationship wasn’t bad. Still, knowing little about her, I could only muster a vague, “Y-Yeah, I guess.”

Mom gave a nostalgic smile. “Grandma’s whimsical… or maybe just active. She lived with us until you and Yuki grew up, which was a huge help. But once Yukari-chan was hired, she said, ‘I’ll leave the rest to you,’ and started traveling everywhere.”

She sounded like an energetic, free-spirited woman.

She must have helped raise Yuki and me. Mom raising two kids alone would’ve been tough, especially with our ages overlapping during demanding years.

“If Grandma saw you now, she’d be surprised,” Mom said, laughing happily.

Her smile relieved me. It showed her good relationship with Grandma and implied I wasn’t someone Grandma would disapprove of—at least, I hoped so.

Still, meeting Grandma felt both intriguing and daunting. Mom and Yuki accepted my relationships with multiple girls, but I wasn’t sure about Grandma. Even if she was free-spirited, her view of my situation was unclear.

“I wanna go abroad too… fancy cafés, clothes…” Yuki sighed, slumping with the letter.

“You’d need to master English first,” Mom teased.

Yuki groaned cutely, “Ugh.” Her studies were going well, but English remained a slight weak spot.

※

“How about this? If I master English, we’ll go abroad together. But for now, maybe a domestic hot spring inn this year?” Yuki suggested, smirking.

Mom, catching something, said, “Yuki, you need to listen properly,” her tone unusually serious.

The phrase “hot spring inn” tugged at my memory. As I pieced it together, Yuki turned to me.

“Hey, Shun-nii, about that family trip we talked about… Mom found some options, and there’s a great hot spring inn among them.”

The four of us had settled on a one-night, two-day trip by month’s end, with hot springs mentioned briefly before.

A trip with Mom, Yukari-san, and Yuki felt warm and inviting. In my old world, I vaguely recalled family trips until elementary school, but those memories were hazy. As a middle schooler, I’d shut myself off, rarely going out with anyone. The recent camp was my first real group outing.

An introvert like me couldn’t imagine livening things up. But with people talking to me, inviting me, I had to respond properly. I wasn’t sure if I was fun, but so far, no one dismissed my words.

Being in a warm circle with charming women was happiness enough for me.

“The inn has separate men’s and women’s baths, but also a family bath! So, how about we all go in together?” Yuki said.

“Together?!” I parroted, sounding foolish.

It wasn’t a proposal I could easily process. A family bath meant all of us together, likely nearly naked despite towels. I glanced at Mom and Yukari-san.

Yukari-san stammered, “Ah, I-I…” It was unclear if she’d known beforehand.

Mom sighed, then explained, “Among the options, Yuki found one with a family bath. She said, ‘I want to bathe with Shun-nii!’ I didn’t mind since I want you two to bond, but…”

Mom had always encouraged Yuki and me to get closer, even allowing us to bathe together before. I still hadn’t adjusted to that as grown siblings.

Yuki chimed in, “But since we’re all going, it’d be more fun together, not just two of us! The old Shun-nii would’ve hated it, but I thought you might be okay with it now. Is that selfish?”

Her expectant, sparkling eyes made my heart race.

Mom sighed again. “Yuki’s set on this. You and Yukari-chan together is one thing, but including me… you’d have to be considerate, Shun-kun. I told her to check with you. Maybe you’d prefer soaking alone.”

She was explaining it clearly. A family bath meant seeing not just Yuki and Yukari-san’s skin but Mom’s too.

Mom was at least fifteen years older, always watching over me. Seeing her lustfully was wrong.

Yet, from the start, her see-through bra had flustered me. She was still an attractive woman to me. Bathing with her, Yuki, and Yukari-san made me anxious about how I’d handle it.

Yuki added, “If you’re even a little uncomfortable, we won’t push it. Your feelings come first. Don’t worry about me, but… if it’s okay, what do you think?”

Mom nodded, placing her arms on the table. “If you like Yuki’s plan, that’s fine with me. I’m not against it. I might be a bit embarrassed being older, but we need your opinion, Shun-kun.”

Both looked at me.

I felt pressed to make a huge decision. Saying no to the family bath might sadden Yuki or imply I was okay with Yuki and Yukari-san but not Mom.

But if Mom secretly disliked exposing herself, it’d be like harassment from me. I couldn’t force her, an attractive mother, into anything.

“If you’re unsure, just say how you feel,” Mom said. “It’s normal to not want your mom included, even if Yuki and Yukari-chan are fine.”

Reflexively, I blurted, “It’s not that I don’t want it! I think… everyone together, like Yuki said…”

It was impulsive but true. Unless Mom truly objected, being together as four was unshakable.

“Really, Shun-nii?!” Yuki leaned forward excitedly.

Mom, eyes widening slightly, waited for me to continue.

“Y-Yeah, unless Mom really minds… Since we’re traveling together, I’m more worried I’ll ruin it. If it’s okay, that inn sounds good.”

My words set up a family bath for the four of us.

Yuki beamed, “Hehe, you don’t need to worry, Shun-nii!”

Mom murmured, “…I see,” then smiled. “You’ve really changed, Shun-kun. My face feels a bit warm, haha.”

Fanning her cheek, she continued, “I didn’t expect this, but I’m not against it—just a bit shy. I’ll take you up on it, then.”

My words, potentially sounding lustful, were met with kindness. I didn’t want to exclude Mom, and their acceptance of me, who’d normally be left out, filled me with gratitude.

“The inn’s available for the 27th, one night, no changes. Yukari-chan, your schedule’s still fine?” Mom asked.

“Y-Yes!” Yukari-san replied, voice high. “R-Really, all four of us, with Shun-sama, in a bath… Haa…”

Seemingly lost in thought, Yukari-san had apparently heard from Yuki before, saying, “If Shun-sama’s okay, it’s obviously fine!” Her stance hadn’t changed.

“…What’ll happen? A bit scary, but… I’m looking forward to it,” Mom concluded, finalizing the plan.

The summer’s end promised a warm, slightly thrilling family trip with kind, captivating women.

“Hehe, I’m super excited too!” Yuki said, her adorable smile captivating me. Just being near her was endlessly joyful.

※

Filling my summer with plans was a luxury.

Summer breaks used to be aimless, but now, daily calls with lovers, a camp with erotic mishaps, and sweet home sex softened my heart.

At night, alone in my room, I reflected on this environment.

Except for yesterday’s camp, Asagi-san and Maki-san messaged me daily, with Asagi-san even calling. My phone was filled with their history.

Interacting with such cute, kind girls felt undeserved, but they stayed connected beyond school.

A ping sounded—Asagi-san’s message: “Shun-kun, can I call now?”

Like recent days, yet never taken for granted, I replied, “Yeah.” The screen switched, showing the luxurious call button.

※

“So, there’s a place where families can bathe together? I didn’t know,” Asagi-san said over the phone.

I shared my summer plans, including the hot spring inn. Worried my impure thoughts might show, I was relieved she didn’t judge me.

I shouldn’t get used to this. Proposing to bathe with women, even family, might upset a lover.

“I’ve thought before, but going to a hot spring with you would be thrilling,” she said. “Though, a nice place might need savings.”

She spoke cheerfully, while I imagined a hot spring trip with her alone, doubting my restraint given her constant assertiveness.

Shaking off indulgent fantasies, I focused.

“So, your plans are around the end of the month?” she asked.

“Yeah,” I confirmed.

After a pause, she said, “My club’s been busy, but I get a two-day break next Monday and Tuesday.”

I realized her intent. Despite daily calls, I hadn’t invited her, and she might be frustrated.

“S-Sorry, I haven’t invited you at all…” I stammered, fearing I’d seem inconsiderate.

I worried about bothering her, but she, my lover, spent precious time on me, even hinting at her free days. I’d been too dense.

Had I disappointed her with my passivity? As dark clouds loomed, she said, “Oh, no, Shun-kun, that’s not it!”

“You can invite me whenever you want. I just thought, if you’re free, maybe I’d invite you this time,” she continued. “Maybe you felt bad for not giving me attention, but it was my phrasing. You’re not upset, right?”

Her anxious tone made me feel worse. I couldn’t respond well, always needing women to cover for me.

“You don’t need to think that, Asagi-san… I worry I’ll bother you if I invite you, but you’re so kind, never minding…”

I spoke honestly. My cowardice and passivity were the issue. She wasn’t at fault—she was overflowing with kindness, inviting me.

“If you invite me, I’m always happy. I’d skip club for you. Your schedule and energy come first, but I’m okay being called every day,” she said sweetly.

Before I could protest, she added, “Just don’t worry. I’m always okay! Hehe! ♡”

Her voice soothed me. My overthinking could’ve seemed distrustful, but she forgave it all.

“Thanks, Asagi-san,” I said, belatedly.

She giggled shyly. She didn’t demand I read her mind, always offering straightforward affection. Yet my weak heart sometimes got in the way.

I had to change, or I’d have no future. As I resolved to focus, her bright voice rang out.

“But now, I’m inviting you! Or rather, proposing something!”

I’d made her conversation circuitous with my overthinking.

“How about going to a hotel pool with Maki, too?”

Her proposal straightened my spine. This priceless, exciting event, aimed at me, sparked countless thoughts.

Chapter 105: The Second Promise with Asagi-san

“You remember when we talked about wanting to go to a pool but wondering about crowds? I mentioned it to my mom, and she suggested a hotel pool a bit far out. You can use it without staying overnight, so I thought it might be nice,” Asagi-san explained carefully over the phone.

Her sensational proposal was about using the pool at a high-end hotel near the sea, like a visitor pass for a golf course.

“But it’s a bit far for just a train, and it’s pricey for us alone. Including your share, it’d eat up a lot of allowance,” she added.

Her assumption that she’d cover my share made me blurt, “N-No, I’ll pay for myself!”

Like Maki-san, she seemed ready to cover my costs. I couldn’t let myself be that kind of guy. As I panicked, Asagi-san giggled, “It’s fine, but thanks,” and continued.

“So, my mom offered to drive us and cover most of the cost! She hasn’t been to a pool in ages and wants to swim, so she asked if it’s okay.”

Her next words straightened my spine again. Asagi-san’s mom, Kurumi-san, would not only drive us but join us at the pool.

The distance made a car ideal, and the cost wasn’t something we could easily manage alone. Kurumi-san’s offer was genuinely helpful.

“My mom said at a regular pool, a guy like you, Shun-kun, might draw attention. A pricier place like this is better. I agreed, so I went with her idea,” she explained.

In this world, a guy my age at a public pool wasn’t typical, even for someone like me, not just high-spec guys. Their effort to choose such a place for me was something to be grateful for, not reject.

“I’ve never been to a hotel pool, and with you there, having an adult like my mom might be reassuring. But if you’re not okay with it, please say so,” she added.

In summary, it’d be me, Asagi-san, Maki-san, and Kurumi-san at the pool, with her wanting to swim too. The image of her slender, beautiful figure in a swimsuit crept into my mind.

I could easily picture Asagi-san and Maki-san in swimsuits. Having been intimate with them, I knew their bodies—underwear, breast shapes, everything.

Asagi-san would likely wear a cute swimsuit, showing off her healthy charm, while Maki-san, perhaps shy, would look like a gravure idol. I shouldn’t take their willingness to let me see them for granted, even after our intimacy. And Kurumi-san swimming casually? That could shatter my worldview.

“It’s for visitors, but hotel guests use it too. It’s less crowded than a public pool, but it might still bother you, Shun-kun. I don’t want you to force yourself, so what do you think?” she asked.

She worried about the attention I’d get as a guy. But I couldn’t let her worry so much, and with Kurumi-san considering me, refusing wasn’t an option.

Swimming with my lovers’ mother was unthinkable in my old world. Was this normal for extroverts there?

I took a deep breath and replied clearly, “Y-Yeah, I’m okay with it. If you and the others are fine, can we… go together?”

Asagi-san laughed happily, “Hehe, I’m the one inviting you, so of course it’s fine! Monday it is! I’m glad… I need to find a cute swimsuit with Maki, one that’ll make you think I’m cute or get your heart racing.”

Her desire to excite me with her swimsuit was unbearably adorable, her voice already overwhelming me with sweetness.

The night we finalized the family trip, a pool date with my lovers was set. With Kurumi-san there, it might not fully count as a date, but it was a luxurious, dreamlike plan for me.

“I’ll tell my mom! I’m looking forward to swimming with you, Shun-kun!” she said.

Her excitement hit me directly. “Y-Yeah, I’m looking forward to it too,” I replied, slipping into polite speech.

My brain, piling up promises, felt like it was boiling.

※

The next morning, after breakfast, I sought Mom’s permission. It was a busy Tuesday for her, so I aimed to be brief.

But I wasn’t skilled at concise, important requests. I spoke too fast, possibly stealing time from Yuki and Yukari-san nearby.

Still, they listened patiently, and Mom said, “Got it,” affirming me.

“I’ve heard of that hotel. It’s new and upscale. I’d take you myself, but Monday’s tough for me. I know Kurumi-san through Mai-san,” Mom said.

She didn’t know Kurumi-san directly but was friends with Maki-san’s mom, Mai-san, likely hearing about Kurumi-san through my ties with Asagi-san.

“With Maki-chan, Asagi-chan, and her mom at a hotel pool, I think it’s fine. Most importantly, you want to go, Shun-kun, so what kind of mom would stop you?” she added.

Hotel pools, she noted, had good security, making them suitable for guys. Wealthy men might even rent them out.

“A pool, huh? The old you would’ve refused hot springs and pools outright. Make sure you prepare a swimsuit. Your school one might work, but if you need a new one, we’ll order online,” Mom said.

I hadn’t considered swimsuits. Men’s swimsuits here probably covered more than just the lower body. Did I still have my school one? Would it suit a hotel pool? So many things to think about.

Yuki, beside me, groaned, “Ugh, I wanna go too!” slumping on the table. She’d skipped beach trips with friends to focus on studies.

“Don’t be rude, Yuki,” Mom said. “If you want to go with Shun-kun, save it for next year. We have the trip this year, and you’ll have time with him.”

Yuki gasped, “Right!” and sat up. “Shun-nii, will you go to the beach with me next year?”

Her sparkling, earnest eyes were undeniable. “Y-Yeah, if you want, I’d love to,” I said.

I wasn’t confident it’d be fun, but her joyful “Yay!” felt genuine.

“Then this year, we’ll relax at the hot spring, and you’ll study hard,” Mom said, wrapping up.

She left for work in her suit, and Yuki declared she’d study in her room.

Promises were shared warmly as a family. It was precious, but I needed to act more proactively.

※

In my room, I checked my pool bag and washed school swimsuit. It was a competitive style, covering my chest too.

This confirmed middle school had separate-gender pool classes. High school hadn’t had them in the past five months, so they weren’t mandatory.

The swimsuit had only my name and class, so it seemed usable. Still, I searched for men’s swimsuits on my laptop, using my April health check measurements.

Options were limited, likely due to low demand, but some were affordable and deliverable in a few days. I bookmarked the page to discuss with Mom later.

Lying on my bed, I stared at the ceiling, replaying yesterday’s talk with Asagi-san.

She seemed to want me to invite her proactively, yet always covered for my passivity, saving my heart.

Glancing at the calendar, I noted it was Tuesday. With the pool on Monday, six days were empty.

I felt that wasn’t good.

I didn’t understand “normal” lovers. Even if we wanted to meet daily, long breaks didn’t mean constant meetups. Asagi-san had club and friends.

But she was always happy with me, laughing, wanting me. A cute, kind, sexually assertive girl like her was any guy’s ideal.

She might have other plans besides Monday, likely choosing it for her free days. If I pushed for more, I’d seem clueless.

Still, she held no malice toward me. I wanted to take her words literally, trusting her kindness.

Clenching my fist alone on the bed, I muttered, “I’ll invite her.”

I grabbed my phone and started drafting a message, taking an hour to send.

※

I chose a message over a call, thinking she might be busy with club or sleeping. I was also nervous about speaking.

I asked if she had time in the six days before Monday, stressing no pressure. The location was tricky. Her preferences came first, but I needed to suggest something.

I leaned toward a familiar place I understood. That meant places I’d been with other girls, which worried me about her reaction. I’d have to explain honestly.

Avoiding a long message, I finalized:

“If you’re free before Monday, want to go out? I thought maybe the zoo, but anywhere you like is fine. Don’t push yourself if you’re busy with club.”

It felt dull, and I considered emojis but gave up. I sent it as is.

The weather wouldn’t be too hot, milder than my old world’s summer. The zoo, where I went with Maki-san, was accessible by train and seemed nice.

I shook off fears of being creepy. Asagi-san wouldn’t think that—I hoped my trust and wish showed in the message.

No immediate read. She might be at club or sleeping. My impulsive message left me anxious.

Was it too forward? Was the wording off? Doubts crept in.

In my old world, fear of failure trapped me. I thought everything I did was wrong, that I shouldn’t act.

That negative loop consumed me, draining confidence and drive, preventing relationships.

But now, those fearful moments were filled with kindness.

A ping vibrated my phone on my stomach. Heart racing, I checked Asagi-san’s reply:

“Sorry for the late reply! Of course, it’s okay! The place you went with Maki?”

She’d preempted my unsaid worry about reusing a date spot. Nervous, I replied:

“Yeah, from the holiday. I wanted to go with you. Is that okay?”