Milf Hunter in Another World

My cockhead was halfway in when it hit a wall…

It was as if her most secret hole was resisting being conquered.

“Relax.”

“Easier said than done…”

I waited for Fiona to be ready.

It’s not like she’s used to having things shoved up her ass.

Even if she practiced with tools, that’s just practice.

If you’re actually going to put a hard, erect dick in her ass, it’s normal to be tense.

It’s the same for Madam.

Especially Fiona, who was a virgin until recently, would be even more nervous.

“I won’t just shove it in.”

“Promise…?”

Relaxing Fiona was the priority.

The preparations were perfect. A clean, pretty ass, diligently expanded with the right tools, was waiting for me.

Seeing her lying face down on the bed, her firm ass lifted high for my viewing pleasure, I couldn’t resist the urge to just shove it in.

Into that tight, pretty asshole…

I wanted to just ram my hard dick in there.

Gulp.

‘I have to hold back.’

Even I, who always thinks about thrusting, understand the difference between an anus and a vagina.

The biggest difference is durability.

The vagina is strong, stretchy, and heals quickly. That’s why you can insert deeper than its actual size.

But the anus doesn’t produce lubrication, so expansion and lube are essential.

Right now, Fiona’s ass was expanded enough to handle the thickness of my dick.

And thanks to the anal beads, her insides were slick with lube…

She had made enemas a part of her routine, so Fiona’s anus was before my eyes for the sole purpose of clenching around my dick…

I felt my dick harden involuntarily.

“Okay. You can put it in now.”

Madam watched intently, as if she had forgotten to breathe, her eyes fixed on our point of connection.

Rubbing my erect dick against Fiona’s anus.

“I’ll go slowly.”

“Uh, uh-huh…”

This was a tense moment.

I gently massaged Fiona’s ass as I slowly pushed my hips forward.

“Fiona.”

“Yes…?”

“Use the same pushing force as when you’re pooping. That’s how you expand your sphincter.”

Fiona gripped the bedsheet tightly.

“This is embarrassing… Can’t we just stop…?”

“What are you saying, sounding just like Madam?”

“Hmph…”

Fiona seemed to be battling an overwhelming sense of shame, her shoulders trembling.

I forgot about Madam’s presence and focused entirely on Fiona’s pretty asshole.

The knight who used to treat me like a bug…

Not only did she become my girlfriend, but she was actively cooperating with anal sex…

It felt as ecstatic as if I was already cumming.

Fiona followed my instructions and focused on ‘pushing’ to expand her ass.

Slowly… It opened…

“Hng…”

Even though she had prepared, imagined, and practiced…

Fiona still seemed unable to believe this was happening to her.

“Fiona. I love you.”

“…Eut.”

“I’m so happy you’re offering your ass.”

“…Ah… Hng… You can put it in now…”

I aligned my cockhead with Fiona’s pretty anus.

Slurp!

“Oh!”

I couldn’t help but gasp.

It’s incredibly good to have a pussy wrapped tightly around your dick, leaving no gaps, but…

This tightness!

In terms of tightness, the anus wins hands down.

So I could just shove it in now?

No, not yet.

The sphincter has two layers.

The external sphincter is the part that tightens when you consciously clench, and the internal sphincter…

You can’t consciously control it, but it automatically opens when a foreign object enters.

I calmly proceeded until Fiona’s internal sphincter was ready to accept my dick.

“Fiona, does it hurt?”

Madam, who had been watching with rapt attention, spoke.

“Hng… Ugh…”

Fiona flinched and replied in a heated voice.

“It’s strange… It doesn’t hurt… but something… Haah… Hng…”

It seemed like she was already feeling something building up.

This was a very good sign.

The anus is an erogenous zone with a high concentration of nerves. Everyone knows you can feel pleasure there…

Or maybe not?

Anyway, it’s common knowledge to me.

But not to these two.

Fiona shuddered, experiencing an unknown sensation, and stuck out her tongue.

“Hak… Hak… It’s… inside my ass?”

“Just the tip.”

“Ugh… Hng… It’s strange… I feel like a pervert.”

“If you feel it from the start with your ass, you’re definitely a pervert.”

Slap, slap.

I spanked Fiona’s ass playfully.

Fiona blushed and accepted the spanking.

“It’s your fault…”

“I’ll go a little deeper.”

Squeeze, squeeze♥

Fiona’s anus tightened around the base of my cockhead.

Ah, this…!

The ass of a knight who trains every day…!

“It hurts a little…”

“More lube?”

“Yes…”

I rummaged through the black hole kit with one hand.

Lube…

Anal lube with the brand mark of Ostega, the anal trainer.

‘He put his brand on it, so it must be good.’

The optimal lube for anal sex is one with a thick consistency.

Of course, it shouldn’t smell, and it shouldn’t dry out quickly.

You need a slippery gel that’s sufficient for anal sex.

In that regard, Ostega’s lube was top-notch, boasting excellent viscosity even with a light touch.

‘What is this viscosity…?’

Did he melt slime or something?

It was comparable to the lubes meticulously crafted by modern scholars.

I thoroughly lubricated my dick with Ostega’s lube and slowly pushed it into Fiona’s ass…

My erect dick… slid in…

“Fiona…!”

“Ugh… Hng…”

My dick was so slippery…

But the tightness of her asshole was so strong that I could feel every bit of friction…!

This contradiction! Slippery yet tightly clenched!

“A knight’s ass pussy… is the best…!”

“Ah, hng…!”

Fiona’s S-shaped colon, here I come…!

I slowly pushed forward, one thrust spanning five minutes, expanding Fiona’s anus as I went.

Squeeze, squeeze♥

Fiona’s ass…

It was squeezing my dick as if trying to wring it out…!

Finally, when my cockhead reached Fiona’s buttocks, I let out a deep breath and felt her ass with my whole dick.

“Haa… Hng… Hu-ang…♥”

Fiona rubbed her forehead against the bed, writhing.

“I really… had sex with my ass…”

“You’re disqualified as a knight, Fiona.”

Fiona’s asshole tightened reflexively as if to protest…!

A trained knight’s anus… So fucking hot…!

I didn’t move, savoring the feeling of being encased in Fiona’s ass, and gently sucked on the back of her neck.

“Hak… Hak… Don’t say I’m disqualified…”

“You’re a perfect girlfriend.”

I subtly praised her, conscious of Verdia.

“It feels like true love, offering your ass like this… I’m so happy, Fiona.”

“R-Really…?”

“I’m touched.”

I placed my hand on top of Fiona’s.

“…”

“…”

Verdia’s eyelashes fluttered.

‘I can do it too.’

Her expression seemed to say that.

She was so resistant before…

After watching Fiona getting delightfully penetrated, Madam’s heart seemed to have been moved as well.

This situation was driving me crazy.

“Haah… Hot…”

The fact that Fiona, who was once hostile towards me…♥ is now actively cooperating with anal sex, slowly receiving my thrusts, was hitting me hard.

It felt like my already fully erect dick was expanding even further.

So fucking hot…

Fiona gently swayed her hips, encouraging me even more.

“I love you… Taeyang, I love you… You can do whatever you want with my ass and pussy♥”

“Your actions speak louder than words, Fiona…”

“Hehehe…”

The corners of Fiona’s lips curled up.

Even though her eyes were glazed over from receiving my dick in her ass, she couldn’t hide her happy smile.

“But if I feel it with my ass, I’m disqualified as a knight. You know what I mean, right?”

It meant she was that embarrassed and ashamed.

Fiona’s ass tightened.

“Disqualified… I don’t care if I’m disqualified as a knight… I want to be loved by my boyfriend with my asshole.”

I kissed Fiona’s lower back and glanced at Verdia.

“…”

“…”

The way she shifted her sitting position, blatantly drawing attention to her own ass, was quite a sight.

I could see a future where I could freely use not only the pussies of these two attractive women, but also their anuses.

Truly the best…

Now…

Should I make the knight disqualified, turning her asshole into my personal playground…?

“I’m going to move.”

“Hee…”

“Ready?”

Squeeze, squeeze♥

“Ready… I’m ready.”

“Doesn’t sound like it. Use your pushing force. Open your asshole.”

“…Hng…”

“Answer me.”

“I’ll open it…”

“Like you’re pooping. Got it?”

“Yes…!”

We had plenty of time.

Time for Fiona’s anus… to get used to my dick.

The sphincter can actually expand beyond the thickness of a man’s dick – even my thicker-than-average dick – so once she’s adapted this far, there’s no risk of tearing even if I move.

In other words, it was time for enjoyable anal sex.

Squish♥

“Hee? Ugh!?”

It reminded me of the first time I had sex with Fiona.

Fiona, writhing at the unexpected pleasure!

“Wh-What is this…!”

My dick is invincible.

Even an anus can’t resist my thrusting!

Squish, squish, squish, squish.

I grabbed Fiona’s waist and delightfully pounded her ass.

Ha, this lube is amazing!

The viscosity is insane. Not a single drop is leaking, perfectly filling the space between my dick and… Fiona’s inner walls.

‘I have to buy this.’

My desire to purchase it solidified.

To think it could make Fiona’s asshole this slick and smooth…!

And this tightness…!

Squish squish squish squish!

“Fiona! Fiona!”

I was already mindlessly pounding Fiona’s ass.

Enjoying the ultimate delicacy, anal.

With all my might!

“Hoot♥ Oh, oh, oh…! Disqualified as a knight… Disqualified as a knight, my ass feels good…”

“Don’t worry. You’re a perfect girlfriend.”

“Ah… Ah… I’m happy… Hmph! I love you… I love you…!”

“I love you too, Fiona…!”

Anal sex! It fundamentally denies the fact that sex is for reproduction, purely for mutual pleasure!

Fiona, who seemed awkward at first due to the unfamiliar sensation… started enjoying the king-dick in her ass, and our movements synchronized perfectly as if we had planned it.

Slurp slurp slurp slurp slurp slurp!

“Ah, ah, ah…! Hmph…! Oh, oh…!”

“Fiona. Tell Madam how you feel.”

“Ah-hng, eut, oh…! It’s really embarrassing to feel it with my asshole… but… Hng… Ah… Ah… My ass feels good…!”

“Fiona… Are you really feeling it with your ass?”

I spanked Fiona’s ass playfully as I pushed my dick deep inside.

Slurp slurp slurp slurp slurp slurp!

“Ah, ah, that… Hook… It’s… It’s amazing… Your king-dick is the best…!”

Fiona’s lewd face, already addicted to anal sex, was her answer.

It was worth the effort.

Squeeze, squeeze. Fiona’s anus tightened around my dick!

“Fiona! Point your asshole properly!”

“Ah… Ah… Hmph… Ah… I don’t want to, it feels so good… This, this is ass pounding♥”

Fiona was so engrossed in anal sex that she couldn’t keep her tongue in her mouth, panting with glazed eyes.

A knight’s firm ass, so fucking hot…!

It felt like I was finally tasting the delicious flesh after cracking open a crab shell and diligently removing the meat.

Squish squish squish squish squish squish!

“Hup! Hup! Eurgh! Ass pussy! Become corrupted by the ass pussy!”

“Oh-ho♥ Oh… Ohh… Oh! No, no… It’s embarrassing… but it feels good…”

Embarrassing but good.

Such sweet words.

Fiona’s alluring ass swayed delightfully with every thrust.

Her pussy was soaked. The juices flowed down her thighs, staining the bedsheets.

“Hng! Oh… Oh… Oh-ugh…! It feels good… My ass feels good♥”

“Want me to go harder?”

“Harder… Thrust harder…!”

“Fiona. Has anal sex completely won you over?”

Oh!

Fiona wiggled her ass from side to side, urging me on.

“Don’t rush me and wait.”

“Hak… Hak… Hurry… Thrust into my ass… squish squish… Do it with your magnificent king-dick.”

I generously applied Ostega’s lube to my dick and climbed onto the bed.

I hadn’t pulled out even once.

I straddled Fiona, my legs slightly wider than her shoulders, and pounded her ass from above.

Thrust thrust thrust thrust thrust thrust thrust thrust!

“Ohhh! Ohh…! Hoot…!”

Squirt!

Even though we weren’t having vaginal sex, Fiona squirted like a fountain, her bladder muscles loosening as she reached climax.

Squish squish squish squish…!

“Do you like anal that much?”

“I like it… My ass feels good♥ Ah… Ah… I love you… Taeyang, I love you…”

“I love you too, Fiona…!”

Anal sex! A purely pleasurable act, defying the notion that sex is for reproduction!

Fiona, who seemed awkward at first, was now enjoying the king-dick in her ass, her head thrown back and her ass lifted high.

Slurp slurp slurp slurp slurp slurp!

“Ah… Ah-ho♥ Ohh… Oh… Oh-ugh…! It feels good… My ass feels good♥”

“Fiona’s anus is amazing too. As expected of someone who trains regularly, the tightness is different.”

“Ah… Ah… Hmph… I never thought I’d train that hole…!”

I relentlessly pounded Fiona’s ass with my cockhead.

Thrust thrust thrust thrust thrust thrust!

Squirtsquirtsquirtsquirtsquirtsquirtsquirtsquirtsquirt!

“Ah… Ah-hak. Hu-ang… Thank you… Thank you for showing me something this amazing…♥”

She had reached a point where she was thanking me for showing her anal sex.

How could I hold back when she was clenching her ass around my dick and saying such things!

“Eurgh!”

Squish squish squish squish squish squish!

“Oh-hook…!”

“I’m going to cum in Fiona’s ass…!”

Fiona stuck out her tongue and twitched, completely exposed to my thrusting.

“Ah.”

Oh right, the magic stone was still on!

I realized it just as I was about to cum.

“Fiona!”

Thrust thrust thrust thrust thrust thrust!

“Oh-hook… Yes, yes…!”

“I’m filming you getting your asshole pounded while rolling your eyes, is that okay?”

Squeeze, squeeze♥ Oh! Look at this naughty ass clenching around my dick!

I spanked Fiona’s buttocks playfully as I vigorously pounded her ass.

Squish squish squish squish squish squish!

“No… Don’t film… Ung-hoot…!”

Squirt!

Fiona’s squirting sounds, the best!

“Your face and asshole are being perfectly captured! Now, point it properly!”

“Oh… Ohhh…! Ohh, ohh, ohh…!”

Now’s the time!

I relentlessly pounded Fiona’s ass with my pre-cumming dick.

Thrust thrust thrust thrust thrust thrust!

“I’m cumming! Cumming in Fiona’s ass!”

“Master… Don’t like it with my ass… if you’re going to film it♥”

“Reach climax with your ass pussy!”

Finishing move!

Slam!

I pressed my cockhead against Fiona’s buttocks and released my semen!

Splurt Splurt Splurt! Splurt!