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

Chapter 82: My Sister’s First Time, Our Lust ☆

Yuki, face flushed, leans against my chest. Her softness and light weight overwhelm me with doki-doki.

I’ll never get used to being close to a beautiful girl. Like the others, Yuki’s a cute, unattainable girl from a different world.

“Thanks, Shun-nii… but don’t push yourself,” she says. Her slightly damp fingers on my back feel like a luxury I don’t deserve.

Her glossy, side-tailed black hair and soft scent stir my heart. Regulating her breathing, she seems to suppress her earlier arousal, looking up at me anxiously.

“So… should I be on top? I heard it’s normal for the girl to be on top, but I might be heavy and tire you out…”

Her thinking about our first position feels deeply immoral and surreal, but my feelings don’t matter.

She’s smaller than Asagi-san or Maki-san, so a tough position might hurt her. Since I’m taking her first time, I must avoid that.

“D-Don’t worry about me… it’s your first time, so we have to make sure it doesn’t hurt…” I say, maybe too late, but I need her to know. Even if I’m excited for sex with her, if she dislikes it, I should discard my lust like trash.

“…Thanks, Shun-nii. Then, maybe I want you to guide me,” she says, catching my hesitation.

“You’ve… done it with Asagi-san and them, right? If so, I want it the same way… is that okay?”

She understands I’m with other girls, yet she’s ready—eager—for me to take her first time.

“N-No, it’s not bad… I-I’ll make sure it doesn’t hurt…” I stammer.

With my experience, I should lead, and despite my lack of confidence, I must do what I can for her.

“F-Facing each other, I’ll move… so, please lie down…” I say vaguely. She responds, “Then I want that too!” kissing my cheek lightly. Her close, repeated smiles make my heart race.

“Ehehe, I’m becoming one with you, like the others. I don’t mind pain, so do it how you want, okay?”

Despite my intimacy with other women, she doesn’t judge and follows my words. Pulling a pillow under her head, she lies back.

“But… I’m a bit nervous,” she says, slowly spreading her legs toward me, exposing her private place.

I touched it in the bath, but seeing it directly is new. I know it’s wrong, but I can’t resist wanting to see her slit.

“…Your cock’s twitching again… so naughty…!” she says, not mocking but accepting my lustful gaze. As I unconsciously move closer, she gently touches her slit.

“You’re looking at me… I might touch it… nn,” she says, stroking her modest clitoris, flinching with a “Fua!” Her loud moan echoes, her melting eyes on me.

“Shun-nii… I-I’m probably super sensitive… I might make noises…” she says, using two fingers to hesitantly spread her slit. Her pristine, pink pussy asserts its purity.

Yet its slight movements and fleshy folds, the fact it’s where my cock will enter, make me uncontrollably excited, my shaft twitching.

“If you’re excited… I want you to take my first time… ♡” she pleads lasciviously, drawing me to her lower body. In the silence of our breaths, I gently bend her legs, positioning her pussy for missionary.

“Y-Yuki… I’ll be gentle… i-if it hurts, push me away…” I say, my words clumsy, desperate not to hurt her.

She shakes her head slightly.

“…I’m okay, Shun-nii. You’re making me happy…!”

She might be scared, but her smile is steadfast. I realize no more confirmation is needed.

Her pussy is right before me. I want to stare at its small, cute allure, but gawking only excites me.

“I-I’m putting it in…!” I declare, guiding my glans to her tiny slit. I feel some slickness, but I have no room to think beyond that.

Given our size difference, I must focus on her reaction to avoid pain. Breathing out, I try to slide in.

As she gasps, “Nn, ah,” a “guchuri” sound accompanies my cock’s slow entry. I keep watching her.

“Aa, nn, ha, S-Shun-nii…!” Her voice sounds tense. Her small slit and tight insides reflect her youth.

“Nn! Y-Your cock’s… inside… ah!” she says. A small “kotsun” sensation hits my glans, and she makes a soft noise.

It’s time. Trembling, I ask, “Yuki… i-it might hurt…!”

At my umpteenth check, she nods. Holding her thighs, I slowly, so slowly, push deeper.

I feel her hymen break with a slight resistance and hear her stifled “!” but she doesn’t push me away.

“I-I’m going all the way…” I say, continuing. Stopping midway might hurt her more, though that’s my assumption.

If she pushes me away, I’ll stop. But as she stares at our union, accepting my cock, I respond to her.

“Nn, aa, yaa… nnn!” she moans. Her tight vagina resists my modest cock, likely feeling foreign due to her small frame.

Yet she nods each time I glance anxiously, her strength and kindness letting me indulge. I finally hit a wall, reaching her deepest point.

In her constricting depths, pulling out seems tough, but I don’t want to see her in pain. I check her expression.

“Ha, ha, S-Shun-nii’s cock… i-it’s in…!” she says, mouth half-open, eyes fixed on me. Her accepting my full length shows her strength.

“Yuki… i-it’s all in… a-are you okay…?” I ask before drowning in pleasure.

Breathing heavily, she answers, “Y-Yeah… I’m okay… nn, ha, b-but my body’s all tingly… ha, nn!”

Gripping the sheets, she endures my cock. She doesn’t seem to dislike it, but it’s not pure pleasure. Her pussy resists movement, a natural reaction to a foreign object, despite her intentions.

Panicking, unsure what to do, she reaches out.

“Shun-nii… just a bit… kiss me…!” she pleads, wrapping her arms around my shoulders. I lean in, kissing her, moving from lip-pressing to tongue-entwining.

“Fu, nn, Shun-nii, fua, nhaa,” she moans, pouring her feelings into my mouth. Her loving act hardens my cock, but her vagina gradually relaxes.

Maybe kissing eased her tension. Amid such convenient delusions, her pussy slowly allows my cock to move.

“…Phaa, S-Shun-nii…!” she gasps as our lips part, eyes teary but free of pain. I feel slight relief.

But now, pleasure creeps into my cock. Though tight, her slick, melting pussy is undeniably a girl’s erotic place.

Realizing I’m inside her, feeling her cuteness and eroticism, my lust grows despite needing restraint. Inserting my filthy cock into a youthful beauty inflates my brain with desire.

“Nn, I-I’m… connected with you… ha, d-does it hurt…?” she asks, worrying about me when I should be concerned for her, always a step ahead.

“I-I’m… feeling good… but you, doesn’t it hurt…?” I ask, maybe late. Her loosening pussy and erotic expression only excite me.

She reaches for my face, cupping my cheeks with trembling, warm hands, heating my body.

“Ha, I’m fine… it hurt a bit at first, but… your kiss made it go away… ehehe ♡,” she says, her flushed smile fueling my lust. My face shows it, my cock twitching inside her.

“Nn, and… your face is so close, giving me such naughty looks… don’t worry, it’s okay… nn,” Yuki says, trying to move but quickly returning to lying down. Looking at me with breathy words, she continues.

“…B-But, I might not move much… nn, so I wanna ask you, sorry for making you… nn,” she says, despite me being the one pushing her.

“Nn, I want you to… feel good inside me… and it’s a safe day, I-I have the morning-after pill… so I want to take all your semen…!”

The mention of the pill startles me. If I’m not presumptuous, she prepared it for me. Despite my cowardice, she’s been waiting for me.

Cumming inside is risky, and a brother making his sister take a pill is scum. Yet, she wants me, and I selfishly crave her pussy.

I have no right to reject her feelings. If she desires this, I can’t be too weak to take responsibility.

“T-Thanks, Yuki… I-I’ll make you feel good too…” I say. Staying still, her pussy feels amazing, and I’d cum soon, but I want us to feel good together.

“I-I’ll move… i-if it hurts, stop me…” I say weakly, slowly moving my cock inside her. Her tight, rippling insides undeniably pleasure me.

“Faa, i-it’s moving… your cock’s rubbing…!” she gasps, her “nn” and “ahn” turning sultry, becoming a woman’s moans.

Though I aim not to hurt her, my hips move, driven by her slickness and stimulation, my lust for her growing.

“Yuki… d-does it hurt…?” I ask, pointlessly, my cock drowning in pleasure. She replies, face flushed, “N-No… i-it feels good… faa, s-so big…!”

Her increasing moans fuel my semen production. Her trembling breasts and hardening pink nipples paint my mind pink.

“Shun-nii… my head’s fuzzy… nn, y-your warmth’s amazing… ha, I wanna kiss…!” she pleads as my cock hits deep. Kissing brings her soft breasts, girlish scent, and erotic saliva.

“Nn, uu, Shun-nii… nn! I-It’s moving, nhaa! Y-Yan! My pussy’s so wet, Shun-nii, i-it feels good… ♡,” she moans. Her saliva fries my brain, I thrust harder, rationality fading. As our lips part, her moans grow.

Hovering over her, I’m at my limit. One more push, and I’ll burst.

But wanting her to feel good, she touches my cheek.

“Shun-nii… ha, your face is so naughty… nn, I’m feeling good with you… ehehe,” she says, smiling repeatedly, cute, kind, dear. The joy of sex with her turns to semen rushing up my cock.

“Ugh, Y-Yuki…” I groan, pausing. She speaks.

“…Shun-nii… ha, cum inside me anytime… I love you… ♡,” she says, her tight pussy, loving expression, and direct affection shattering my restraint.

“Ugh, s-sorry…!” I cry, my cock exploding, semen flooding her depths despite her precious first time.

“Nhaa, S-Shun-nii’s… cumming inside… ah, s-so much… fa, nn, y-your cock’s moving…!” she gasps, watching my expression, her pussy squeezing, accepting my semen.

“Shun-nii… your semen’s inside me… ha, ah, it’s filling me… ♡,” she says, pulling my head for another kiss. Amid countless kisses, I finish inside her.

As my ejaculation stops, our long kiss ends. Staring, we share a final light kiss, and I slowly pull out, “zuruzuru.”

“…Ha, t-that was amazing… ah, your semen’s coming out…” she murmurs. Her twitching slit leaks white fluid, some spilling onto the sheets.

“Nn, it’s so thick… inside me… fufu,” she says, touching her slit, stroking from her clitoris, smiling as she feels it.

“It’s a waste to let it spill… ahn, but it means you gave me so much… it’s so doki-doki… ♡,” she says, gazing at me lovingly, caressing her pussy. Her stimulating sight excites me despite just cumming.

But it’s her first time, and the sheets show blood mixed with her fluids. Breaking her hymen must’ve hurt.

“Yuki… a-are you really not in pain?” I ask.

“No, I’m fine! It hurt just a moment… but your cock and warm kisses made my heart all warm…” she says, sitting up, snuggling like a puppy. An unworthy naked beauty.

Yet she gave me her virginity and says she loves me. Hesitantly, I stroke her hair.

“Ehehe, Shun-nii… I’m so happy… I really love you ♡,” she says, accepting my selfish act, giving me a mischievous, upward glance.

“Hey, Shun-nii… one last request, okay?” My heart jumps, but I nod, “Y-Yeah.” I can’t imagine her post-sex request, but I can’t refuse.

“Let’s… take a bath together,” she says, recalling her “someday” promise. She wants intimacy now, and a bath with a girl is my ideal.

“…It’s my birthday, so I wanna monopolize you today. Wanna go together?”

Another bath with the sister who gave me her first time. She wants communication, and I can’t expect more. I mustn’t act forcefully with selfish hopes.

“Y-Yeah, t-together…” I reply, nervous. Even after sex, I can’t treat a shared bath casually.