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

Chapter 21: Post-Coital Anxiety and the Next Day’s Thrill

In a dreamy state, I face Asagi-san. Still lying on the bed, both of us naked, my penis and her pussy are close, still wet from earlier.

The act just moments ago—my penis fully inside her pussy, rubbing repeatedly—was undeniably pleasurable and strange. That was sex.

I lost my virginity to the girl in front of me. Not forced, but a natural, mutual first time, or so it feels to me.

“I think I really like this position… Fufu.”

Asagi-san laughs happily. Today, I’ve seen so many of her expressions, an honor I don’t deserve.

First, I must thank her. For not rejecting my lust-driven self, I bow my head.

“…Asagi-san, today… for being my first, um, thank you so much…”

My words are clumsy, but sincere. If she hadn’t invited me to study, this wouldn’t have happened.

But I can’t help wondering her intentions. Even if I was just a convenient partner for her to lose her virginity, I’d still be happy.

“But… you giving your first to me, it feels like a mistake. I’m just an ordinary guy with no good qualities, yet a cute girl like you chose me… I think you’re misunderstanding something about me…”

I’m not someone she’d like. If she expects something from me, I need to tell her I can’t meet those expectations.

Yet, she looks troubled. With a “Fuu,” she sighs and speaks slowly, not angrily, but more deliberately than usual.

“Sato-kun, if you think too lowly of yourself… it makes me a bit sad. It’s very you, but… hmm…”

Making her sad is the last thing I want. But I won’t understand her intentions without hearing more.

“I want to be close to you, Sato-kun, and there’s no mistake in that. You’re the first boy who accepts me when I talk to you.”

“I’ve had close girl friends, but with boys… probably not since elementary school. I tried talking to boys before, but it never went well.”

If a cute girl like Asagi-san spoke to them, even shy middle school boys would fantasize. It’s unthinkable she’d struggle.

“So, someone like you, Sato-kun, feels really rare. You listen to anything I say, don’t dislike us, and… even go along with naughty things.”

She talks of our encounter as unique. Even in this reversed world, she’s too positive about a guy like me with no redeeming traits.

“Being able to give my virginity to you, who’s so proactive… I’m thrilled. So… I want to keep being close. Maybe walk home together, hang out somewhere… and, sometimes, do what we did today, if that’s okay…”

“If you don’t mind,” she adds, looking down but watching me. For a bottom-dweller like me, her unbelievable request is too cute, and she’s still naked.

Her trembling breasts are right before me. This girl who moaned so much earlier has me completely captivated.

I think I have feelings for her. I want to be friends, ideally lovers, and do this anytime.

But I don’t want to betray her feelings. She’s giving me sweet praise, positioning herself as a friend. Maybe she thinks there’s some benefit to being close to me.

I don’t want to think she’s calculating, but I’m protecting my heart by assuming so.

I’m a cowardly person, after all.

“I-I’d love to hang out with you anytime, if you invite me… and, uh, doing stuff like today… is fine with me…”

I manage to express my feelings. Even if it’s calculated, I want to spend time with her.

“Really…? I’m so happy… then, wanna exchange contacts…?”

She stands to grab her phone, getting off the bed. Then, she says, “Ah,” holding her crotch.

“It’s… dripping out again… Sato-kun’s…”

Her thighs show my semen leaking from her slit. It reminds me I came inside her.

There’s no doubt now. Still, I bow to her as she holds her phone by the bed.

“S-sorry… I… came inside you…”

Though she asked for it, I’m the one who came inside. Did I ruin her life with my pleasure-driven act? Anxiety floods me.

There’s no hint she’d demand compensation, but if she did, I couldn’t refuse.

“Eh? It’s fine! Today’s a safe day, and I’m the one who stopped you from pulling out.”

She reassures me there’s no pregnancy risk.

“I wanted it… you’re too kind…”

Muttering, she grabs her phone from the desk. I rummage through my bag, fumbling with my barely-familiar phone. The chat app’s basics are the same, despite a different name.

My mom and Yuki’s contacts were pre-entered, but this is my first classmate’s. Even in my old world, I never had a female classmate’s contact, so Asagi-san took another first.

“Then… I might message you for no reason, but you don’t have to reply… okay?”

Her saying she’ll chat with me is already a blessing. I vow to reply carefully and sincerely.

Exchanging contacts with a girl is a huge event for me, nearly overshadowed by our pleasure.

She glances at the clock, hesitating before looking at me.

“I’d love to talk more, but… it’s getting late, so maybe you should head home.”

The clock nears 6 p.m., a bit later than my usual return time. I should go, and lingering might make me lust for her again. I need to control my excess desire.

She changes into casual clothes, and I put on my uniform. I didn’t wash my underwear, so I stuff it in a plastic bag, wearing my pants commando.

She offers, “I can wash it if you leave it…?” but I decline. Letting a girl wash my semen-soaked boxers feels like a scumbag move. I can’t burden her.

Still, I accept her offer to walk me home since it’s dark. We walk through the residential area, just a five-minute distance, but she insists I shouldn’t go alone.

“…”

An awkward silence hangs as we walk with little conversation. Unless she speaks, I can’t start one. I feel pathetic for not changing.

We reach my house quickly. “Th-then… this is fine…” I say shakily. She turns, bows, and says.

“Th-thanks for today… see you tomorrow…!”

She runs off, back the way we came. I don’t know her emotions, nor can I ask.

When her figure disappears, I take a deep breath and unlock the door. Mom isn’t home yet; only Yuki and Yukari-san’s shoes are in the entryway.

To calm myself, I align my shoes more carefully than usual before heading to the living room. Yuki, in casual clothes, is on her phone but runs to me when she sees me.

“Welcome back, Shun-nii! How… was today?”

I feel seen through, but I can’t say I had sex with a classmate. Even for family, I can’t admit it.

“W-well… we were studying…”

I try to act calm. Looking back, Yuki encouraged my closeness with Asagi-san, showing foresight.

“I see,” Yuki says, her lips curling slightly, leaning close to my ear.

“I could see you talking at the gate from my room.”

It hits me after a moment—she saw me with Asagi-san. Her second-floor room has a clear view of the entrance.

I don’t know how to respond, stammering, “Uh, w-well…” unable to hide anything, flustered.

Yuki says, “Ah, sorry, Shun-nii, calm down…?” soothing me, letting the talk continue. I’m a useless brother, led by my sister.

“I’m not mad at all. I’m happy it went as I said… you’re already walking home together.”

She darkens slightly.

“But… I hope you haven’t forgotten you said you’d walk home with me too. If I’m ‘done with,’ that’s fine, but…”

I might’ve made her feel lonely. Even as a bad brother, I know I need to clear that up.

“…Yuki, you’re my precious sister… I’d never say you’re ‘done with.’ I’m not promised to Asagi-san, so I was planning to go with you tomorrow… sorry if I made you worry.”

My words stumble, ending in apology. They’re honest, but they might hurt her.

“S-sorry, Shun-nii… I didn’t mean it like that…!”

As I bow, Yuki shakes her head frantically.

“I’m happy you said that… I still want you to be close with Asagi-san. I was just being greedy.”

She smiles, forgiving me. To my wonderful sister, I say we’ll go together tomorrow, and she happily agrees.

I’m probably at the “getting close” stage with Asagi-san. But having sex goes beyond that, something I can’t tell others.

Yuki said it’s fine to get as close as I want. But I don’t know what that includes or how much to tell her, still unsure.

While wrestling with my thoughts, daily life continues. After dinner and a bath, I prepare for tomorrow, the last day of my trial club period.

I plan to visit the literature club, but there’s a concern. How should I face Asagi-san at school?

Will she greet me as usual? I don’t know, and my mind’s limit is to respond normally if she does.

I’ll be more awkward than ever, I’m sure, resigned to it. Closing my eyes in bed, I avoid recalling Asagi-san to prevent masturbating.

Waking up, I check my lower body. No wet dream, so I’m relieved, but my mood is heavy.

What if she won’t look at me? What if she regrets yesterday? What if it never happened?

Various anxieties linger, unpopped.

Honestly, I don’t want to leave my room. It’s my first time feeling this since coming to this world, a realization of how hard it is to connect with women.

Feeling this way is progress from my old self, but I’m not used to facing such struggles.

As I grapple with anxiety, a knock sounds, followed by, “Excuse me.” Yukari-san enters in her usual apron.

“Good morning, Shun-sama… it’s almost time for breakfast…”

It’s been since my first day here that she’s said that. I usually go downstairs myself, so this shows how lost in thought I am.

“S-sorry… I’ll be right there.”

I jump out of bed, still in pajamas, unprepared. I start unbuttoning to change into my uniform.

“Sh-Shun-sama! W-wait a moment…!”

Her voice stops me. In my rush, I forgot she was here. Today, I’m worse than usual.

Blushing, Yukari-san says, “…E-excuse me…” and leaves. I clearly showed her something bad.

Dressed, I eat breakfast in the living room. Yukari-san acts as if nothing happened, Yuki seems normal, and Mom watches us with a smile.

“Then, Shun-nii, let’s go?”

Yuki says, and we leave, walking the usual path. I wonder if she’ll bring up yesterday, but she talks about her class as usual.

Maybe yesterday is just yesterday. Then, she stops, her face serious.

“Um, Shun-nii, if something progresses… I’d like you to tell me, okay…?”

I nod, lacking the wit for a clever reply. Seeing me, she smiles again.

Her bright mood lasts until we part. She says, “See ya, Shun-nii… good luck with everything!” with a meaningful tone.

Her usual smile carries a hint of depth. I worry I’m messing up our communication, anxious as ever.

Still, facing Asagi-san in class is thrilling. I head to the classroom, but it feels like it takes longer than usual.

Entering, Asagi-san isn’t there yet. I get the usual glances from girls, but I don’t dare check, assuming they see me as foreign, and sit down.

Fidgeting, I see Asagi-san enter with Yamamoto-san. She greets friends as usual, but spotting me, she clearly averts her gaze.

Not ignored, but it feels like a vague blow. Caught in selfish emotions, she strides toward me alone.

“M-morning, Sato-kun! Let’s… do our best today!”

Her tense words aren’t typical classmate talk. It’s obvious she’s thinking of yesterday.

“M-morning… yeah, let’s do our best…?”

I try to stay calm, but I don’t know how I seem. Avoiding her eyes probably made it more awkward.

She mumbles, “Y-yeah, right… let’s do it…” and stays put. Unsure what to do, Yamamoto-san approaches.

“Asagi…? You okay?”

Yamamoto-san checks on her worriedly. Snapping back, Asagi-san blushes.

“S-sorry, Sato-kun… later…!”

She leaves the classroom, not returning until just before class, sitting quickly with her head down.

During lessons, she doesn’t turn around, and I’m at a loss. Unable to speak first, morning classes end as usual.

At lunch, unlike usual, she goes straight to Yamamoto-san, leaving together. For the first time, I spend lunch alone.

She must feel super awkward. Certain of it, I eat my bento alone. In my old world, I was always alone, so it shouldn’t feel odd, but it’s lonelier than expected—probably because I’ve tasted luxury.

I finish eating quicker than usual. With extra lunch time, a rare feeling, Yamamoto-san returns alone, whispering to me.

“Um, Sato-kun… Asagi says she wants you to come to the rooftop…?”

Her quiet message puzzles me. Why choose a confession-like spot? My tension is just my overthinking.

I climb the rooftop stairs, opening the heavy door. I heard it’s open during breaks but less popular due to the long climb.

Only Asagi-san is there. Seeing me, she bows deeply, almost bending over.

“S-sorry! This morning, I got embarrassed and didn’t know how to act with you… so it felt like I ignored you, but I didn’t mean to…!”

She apologizes without looking up. I didn’t think she ignored me, and I clumsily convey my feelings. She doesn’t need to apologize.

“It might be awkward… but if you still want to be close with someone like me… I’d be really grateful.”

She looks relieved, so I ask.

“I thought maybe you regretted yesterday… if you do, please tell me…”

She gestures broadly, denying it.

“Regret? No way! I was worried you regretted it… thinking about it, I couldn’t talk properly… sorry.”