Ursula's Companions (5) Libera

Holy Knight Libera. At our first meeting, she'd treated me politely as Ursula's secretary, but when I'd been disrespectful toward Ursula, she'd glared and bristled with anger.

By Garumon standards, she had a relatively level-headed disposition.

So while she still treated me politely as Ursula's secretary, she seemed to draw a line and avoided growing any closer to me than necessary.

… Or rather, the other companions who'd grown close to me beyond what was necessary were the strange ones; she was the normal one, I thought.

Still, since a rotation had been set up where each of Ursula's companions spent a night with me in turn, I ended up with a quiet night to spend with Libera too.

"… Now then, Naoto-sama. If you have any questions or concerns, please ask.

"So long as Ursula-sama has deemed you worth raising and intends to do so, I shall cooperate as well."

Libera offered, polite as ever.

"Yeah, thanks."

That said, as for things I specifically wanted to ask Libera myself…

"Um, I guess I'd like to hear an explanation of secretaries again."

"About secretaries, is it… Understood. I shall explain anew."

"Let me see… Among the NPCs in this world, there are two kinds: those who are born as ordinary Garumon and then become NPCs, and those who are born as NPCs from the start.

"We secretaries are largely born as NPCs from the start, in order to assist B-Class-and-above Masters in running their corner of the world.

"Of course, there are also some Garumon who became enchanted with secretarial work, fervently wished to become secretaries, turned NPC, and took up the role.

"In my case, I'm the former.

"In general, those born as NPCs bear a role close to that of the system, and so they possess special talents.

"Specifically, talents of SSR rarity or higher.

"In other words, even among secretaries and mages, if you can recruit one who was born an NPC as a PC, you'll reliably obtain an SSR-class Garumon or better.

"You'll also have a higher chance of obtaining a UR-class one than from a general search.

"That naturally depends on the Master's eye, of course.

"Lining up all secretary candidates…

"The system screen won't show you, so you have to rely on the Master's eye.

"There's a saying that the first thing a Master promoted to B-Class should do is woo a secretary… but that's largely dated advice now.

"In recent years Knight Garumon have been popular and many Masters already own one, and Masters who promote to B-Class almost always already hold an SSR-class Garumon, so wooing a secretary is no longer strictly required.

"Secretaries and mages have one of their skill slots filled by a class skill, after all.

"Even so, plenty of Masters still feel that more than makes up for it, and even at A-Class and S-Class, the Masters who count their secretary as part of their fighting strength are far from few."

So Libera explained.

… It was much more practical advice for a Master than information about secretarial work itself.

"Well, in our case, Colette has been a great help."

"Yes, Colette-san is very promising. I'm truly looking forward to her growth."

It seemed Libera unexpectedly thought highly of Colette.

"Oh, so you think Colette has talent too, Libera."

"Ah… no, I overstepped. My apologies. Commenting on other NPCs is, in principle, forbidden.

"Of course, I'm no longer an NPC at present, so the rule doesn't actually bind me, but…"

Ah, so telling someone "that one's UR-class, that one's SSR-class" was off-limits.

You could tell just by looking at them, I'd think. But there were probably clueless Masters out there with no eye for it.

… The reason my UR-class hit-rate had stayed at 100% so far was thanks to having gazed at Setsuna's beauty from childhood and trained my aesthetic eye.

"… Recruiting an NPC is, by nature, difficult.

"Securing the NPC's own consent is an absolute requirement; it isn't simply a matter of fulfilling some condition.

"Princesses, who join you when certain conditions are met, are actually the easiest NPCs to recruit."

Libera added.

"Really? I'd heard a lot of Masters recruit secretaries, though…"

I was pretty sure Stein was one of those. And what about Yamagata's place?

"A secretary is always close at hand, after all. If a Master has a certain level of ability and talent, in many cases the secretary will agree to join.

"The moment I met Ursula-sama, I saw a crown above her head. I knelt and begged to be allowed to join her.

"So when I was invited from NPC to PC, I accepted feeling as if I'd ascended to heaven.

"Perhaps Colette-san looks up to you in that same way."

Libera smiled at me.

I hoped that was the case. When I'd recruited her, it had felt like I'd more or less railroaded the request through to get her to join.

Though there was no doubt she felt respect, or longing, toward me.

In any case, I had to remain a good Master who didn't betray Colette's admiration.

"Thanks, Libera. I learned a lot.

"Oh, this is a forward request, but… could you give Colette training as a secretary, or in combat?

"I think learning from you would be the best study Colette could get.

"… I'll pay any reward I can manage."

"A reward, is it… Anything would do?"

"Anything? No, there's what I can do, and what I can't…"

I started to say. Then I reconsidered. Saying "I'll do anything" depended on trust in the other party.

You shouldn't say "I'll do anything" to someone who'd reply, the moment you did, "Then go hang yourself and die."

But to someone you could trust not to actually demand anything awful, surely it was fine to say.

Libera… well, our acquaintance was short, but she was a companion of the trusted Ursula, and I felt sure she was someone of trustworthy character.

"No, I'll do anything."

I rephrased.

"… To be trusted that much. In that case, swallowing my pride, I'd like to make a request."

And then…

"Mn, hamu, nchu, juru, jupu…"

"Ah, ahh… Libera…"

Libera, now stark naked, was slurping on my penis.

"Well… how is it? My service with my mouth… is there anything you're dissatisfied with?"

"N-No… it feels really good. Nothing dissatisfying at all.

"Just, lately I've come to think of fellatio as nothing more than foreplay before insertion, so I don't place much weight on it."

"I see… is that so. That's instructive."

Libera jotted something down in a memo.

Uh, ummm…

"Then, may I take it that preparations are fully in order?"

"Yeah. They're all set."

"… Then, please look after me."

With that, Libera lifted both knees up and spread her legs.

Beautiful Libera's beautiful, sparkling pink omanko parted faintly, inviting me.

"… The truth is, in my secretarial duties, there's one part I'm not so good at…"

"Oh? And what's that?"

It was surprising that the seemingly perfect secretary Libera had a weak spot.

"… My night service… to Ursula-sama… my Goshujin-sama."

"… Pfff."

If I'd been drinking something, I'd have spat it out.

"I'm a little… no, quite a lot more sensitive than most people, so when I attend Ursula-sama at night, I feel intense pleasure and lose consciousness before long. I find it very hard to satisfy Ursula-sama through to the end.

"Even after I've fainted, Ursula-sama still ejaculates, but there's a clear difference in the volume of semen between when I stay awake to the end and when I faint and leave Ursula-sama to finish alone.

"I want to become someone who can hold her consciousness firmly to the end and complete her service to Ursula-sama.

"Also, sometimes the climax is so overwhelming that I lose control of my bladder… I've even gone so far as to splash urine on her, a blunder I ought to atone for by cutting open my belly.

"Ursula-sama always laughs and forgives me, but truly, I'm too unworthy…

"I want to improve on this point as well…

"So, regarding improving my night service, I'd like to ask for your cooperation, Naoto-sama."

Libera bowed her head deeply.

"Wha… Ah, no, cooperation like that's more than I could ask for. I'd be the one wanting to ask, if anything…"

"N-No. However, my body—body and soul—is wholly given over to Ursula-sama.

"Without Ursula-sama's permission, I cannot engage in vaginal intercourse."

At this point we were still before the A-Class promotion, so I hadn't received that permission.

"Therefore, I'd like to ask you to teach me by other methods, within whatever range is possible. I know it's a difficult request, but…"

"Ah, no… well, if that's the case, I'll cooperate to the best of my ability."

"… Thank you very much!"

Libera smiled radiantly.

Hmm, what a diligent person.

"Ah… I'm so glad I swallowed my pride and consulted with you, Naoto-sama…!"

Libera smiled. To be relied on by such a beautiful woman… any man who couldn't answer that wasn't a man.

"All right, leave it to me! Let's train hard so you can satisfy Ursula properly!"

"Yes! Please look after me!

"… I'll report your consent to Ursula-sama."

Ah, so it wasn't a secret training session. Of course not. Practicing sex behind your Master's back with another Master would be unthinkable.

So, then—what I was going to put in this time was not the sparkling, inviting omanko, but…

"Then, let's practice with Libera's butthole. Do you have experience with anal?"

"Y-Yes! … However, even with anal intercourse, I can't withstand the pleasure and end up fainting… a-and… when I faint, well, t-truly to my shame… I-I… defecate… I've had that happen, and Ursula-sama has, um, had me hold off on it…"

"Ah, I see…"

That had to be deeply embarrassing. For such a wonderful, modern-career-woman type of beautiful woman as Libera, sensual as she was, to do something like that… well.

"Well, with me you don't have to put on airs. If it comes out, just let it out."

"I-It won't come out! I've prepared properly!"

I scooped up Libera's love-juice with my finger and slid it into her butthole…

"Hyu, n, nhaa…"

Twitch, twitch.

Just one finger's brush, just the tip slipped in, and she was already feeling it… yeah, she really did seem extremely sensitive.

I pressed the tip of my penis against her butthole and gently slid it in.

Her anus stretched wide, ggh… and swallowed the tip of my penis.

… Whoa, this was… tight. It felt good…!

The pleasure was almost enough to melt me on the spot.

"Ah, haaaaaa…!"

But Libera looked even more pleasure-stricken.

Deeper.

It was tight and tough going, but I shoved my penis in, zubu zubu.

"Hig, nha, agu, hia…!"

Bikun, bikun, bikun!

With every little movement, Libera's butt clenched, kyuuuu!, and love-juice gushed, bushu, bushu, out of her omanko.

"… Libera, you've already… lightly come? Let's pause for a bit."

"Y-yes, hyaa, hyii, s-sorry…"

Twitch, twitch… her whole body looked to be in that hypersensitive post-climax state. If I touched her breasts right now, she'd probably come from that alone…

Hmm, she was going to wear out fast at this rate.

Libera came way too easily. If she was coming at this pace just from me slipping it in slowly, then if I thrust at a normal pace her climaxes would pile on top of each other and she'd surely faint from it.

… Then the only option was to go slow. But ah, that was impossible.

Libera's butt felt too good.

When such a delicious hole was squeezing me tight, I couldn't help but thrust hard.

Even staying still was taking enormous willpower.

What to do… would it work itself out once she got used to it? But if so, she'd been with Ursula for about five years now, so they should have shared a body more than enough times. If even that hadn't yielded progress, what else was there…

In any case, I marshalled every shred of reason I had and worked, desperately, to push in bit by bit so as to minimize Libera's burden.

Finally, I'd seated myself to the base.

"Haa, haa, haa…"

Libera, who'd come at least ten times lightly by then, was already exhausted.

I wanted to come too, but… the moment I came I knew the pleasure would set her off again, so I had no choice but to hold on with all I had.

"It's all in… Libera, your butt feels really good."

"… G-Glad to hear it… t-then… please move…"

"… You sure?"

"… I-I'll do my best."

… Let her do her best, I supposed. I was past my limit too.

… All right, time to get a little creative with how I moved.

Zu, zu, zu…

Short, fast strokes at high tempo. Matching Libera's climax interval, moving rhythmically, so that the timing of her butt's contractions and the timing of my piston-strokes synced. With that, the pleasure maxed out, and in just a few seconds I was at my peak.

"I'm going, Libera…!"

"…!"

Doku, doku, doku!

"Ha, ahhhhh…!"

Since I'd held back so much, I let out a lot.

"…!"

At the very end, Libera squeezed her butt, gyuuuu, tightening and pushing my ejaculation's pleasure even higher. It was an exquisite bit of butt-work, draining me to the last drop and not letting any escape.

"Ah, ahhhhh…!"

This was… amazing. From the bottom of my heart, completely satisfying…! Perfect…!

The moment I shot the last drop, Libera's butt relaxed almost simultaneously.

Slump…

Libera had completely fainted.

Zururi…

The penis, slightly softened from ejaculation, slipped out of the loosened anus.

Pupyu, tororo…

Semen flowed out of Libera's butthole.

… Yeah, she really had prepped properly. If she hadn't, defecation at this point would've been unavoidable.

"… Ha… H-how was it?"

"… It was perfect. The timing just now was flawless.

"Libera, your tendency to come easily isn't a flaw at all. Each climax cinches the squeeze tighter, so if you match your hip movement to that timing, your partner gets tightly, efficiently squeezed at exactly the right moment, and it feels incredibly good.

"… So you can make a partner ejaculate quickly.

"If Ursula's ejaculation timing comes earlier, then even if you faint when you come, she should be able to ejaculate at the same instant."

"…! That such a method… existed!"

"Well, the fact that it worked this time was largely luck. Libera's climax timing and my hip motion happened to line up nicely…

"Plus, the gap between Libera's last climax and her fainting happened to be on the longer side this time.

"If you faint too quickly at the end, the squeeze loosens during the act, and the final ejaculation won't reach its most pleasurable peak.

"That would leave the final dotting-of-the-eye undone.

"The only way to extend that is mental fortitude. From here we just have to practice over and over."

"… Yes! Thank you so much, Naoto-sama! Please continue to guide me!"

And so, with Libera I came to do training sessions of this sort.

The only time it went this smoothly was the first one; after that we failed many, many times. Either I'd make her faint too early, or, conversely, I'd come at some weirdly early timing and throw off the rhythm Libera had been carefully building…

It actually started me wondering how I'd been able to come so perfectly in sync with everyone else up till now. It wasn't that the others had low sensitivity; rather, their threshold-to-climax sat far deeper.

While the others reached orgasm at a pleasure level of 10, Libera reached orgasm at 5, roughly speaking.

When she hit 10, she couldn't endure the pleasure and fainted.

That was why she'd been worrying about not being able to satisfy Ursula. But in reality, Ursula thought Libera coming over and over was utterly adorable, and had no dissatisfaction at all.

Since Ursula had no dissatisfaction, Libera couldn't even consult anyone about not satisfying Ursula, and that was where she'd been stuck.

… Difficult things.

And so, a month later…

"Naoto-sama!"

Libera came rushing into my bedroom. Stark naked.

"… Look at this, please…!"

With that, kupaa, she spread her omanko open to show me.

Thick, white liquid trickled out, dorori. Very dense, and a generous amount.

"Ahh, that's…"

"… Yes! With Ursula-sama, at last, without fainting, I was able to receive this much ejaculate from her…!

"Conversely, Ursula-sama climaxed and lost consciousness herself…!

"Ah, at last, at last I too got to witness, with my own eyes, the thing everyone had been talking about,

"'When Ursula comes, sometimes she faints, it's so cute'… and now I've finally seen it firsthand…!

"Her sleeping face was so cute, so cute…!

"It's all, all thanks to you, Naoto-sama…!"

Libera was overjoyed.

"… Heheh, I'm glad you're happy, but… if you come bursting in dressed like that, I'm the one who's going to lose it."

"Ah, ah… I-I'm sorry, in my joy I forgot myself, how embarrassing…"

Libera grew bashful, but…

"B-But… ever since Ursula-sama gave me permission for intercourse with you, Naoto-sama…

"I had been desperately hoping that, once I'd satisfied Ursula-sama, I could let you taste my omanko, Naoto-sama, and I just couldn't sit still…"

She confessed.

… I-I see. Libera, too, had been wanting to be with me so badly she'd flown over…

"My, my, Libera-chan, congratulations…!"

In truth, today was Saria's turn, so I'd been right in the middle of being with Saria…

"I-I'm sorry, Saria… I'll yield my next turn, so today, please…"

"Fufufu, if it's Libera-chan's commemoration, I'll happily yield Naoto-chan to you.

"Now, I'll clean you up… mn, mn… There, all clean. Now go and let Naoto-chan dote on you."

With that, Saria sucked and cleaned up Libera's groin for her.

It didn't look like I'd get to see Saria's daughter mode today, which was a bit of a shame.

But just thinking that I was finally going to be with Libera made me stand up even more.

"Then… here I come, Naoto-sama…"

And then Libera, with her omanko, swallowed up my penis…

"Nha, ah, ahhhh…"

The way Libera had improved was this.

She still came easily, that hadn't changed. But she'd learned to speed up the tempo of her hip movements and adjust so that she came once per thrust.

When she moved her own hips, she could pretty much execute it perfectly. The remaining task was learning to match it when her partner was thrusting, but that was a future challenge.

Jupo, jupo, jupo.

"Nho, aha, higi, ngu!"

Coming with every thrust had to be quite the strain on Libera, but with each climax she'd squeeze, gyuu, gyuu, and that was rough on me too.

I mean, it felt incredible. But rough!

"Gua, ah, Libera, Libera…!"

"Nha, ah, ahhh, ah, ahhh, ahhhhhh!"

Coming over and over, she tasted deeper pleasure each time, and the squeeze grew tighter each time.

I, too, was forced to climb whether I wanted to or not. No, I didn't mind at all. And then…

Zun, gyuuuuuuu!

The instant I drove deep, she clamped down with brutal squeezing-strength.

Ah, no good, my own dam was bursting too…

"Ahhhhhhh!"

Doku, doku, doku!

I ejaculated like an explosion.

"Nha, ahh, ahhhhh ahooooo…!"

Byuku, byiku, byikuu!

Libera, eyes rolled back, twitching all over.

Slammed with semen at brutal pressure the instant she climaxed, she was on the brink of fainting. But she did her best to hold the squeeze right to the end.

And then…

Once she'd wrung out the last drop, she fainted in apparent satisfaction.

"Haa, haa, haa…"

Libera, whole body limp, eyes rolled back, collapsed forward. But her face wore a satisfied smile.

"Haa… It really, really felt good, Libera… I'm completely satisfied. You did great."

I gave Libera a soft kiss.

I'd grown… fully close to Libera too, hadn't I.