Chapter 53: Chapter 53

The strong scent of soap rose from the groin area, must’ve washed up a lot.

Spreading the anus seemed embarrassing, kept fluttering, and juices dripped drop by drop from the pussy.

Maybe because of the enema, the hole that had been tightly closed was slightly open.

It looked like it needed to be loosened before inserting.

My 20cm thing could tear it if I just shoved it in.

I dipped my fingers in the pussy to coat them with fluids, then slowly applied it along the anal folds.

「Aah…eek…feels weird there..」

Despite the gentle touches, the folds gathered inwards, blocking the intrusion of foreign matter.

Seeing no signs of it loosening up, I decided to stimulate both holes at once.

Lifted my resting left hand, inserted my ring and middle finger into the pussy.

Although sticky and melted, it felt harder than usual as if tensed up.

I gently rotated the pussy folds 360 degrees while rubbing.

「Aaah..♡ Hnn… ♡ Hoo..! Aah♡」

The anus twitched more frequently.

Not yet used to being penetrated, but it seemed to feel it more towards the upper part.

I slyly pushed my finger deeper to penetrate.

There was resistance, but I managed to get two knuckles in.

Applied more pussy juice from the fingers around the anus to reduce friction.

The goal this time was to get the whole finger in.

Applied more pressure with my hand.

「Aah..♡♡ Hnn… Is the whole finger in..? More bearable than I thought.」

The insides rapidly contracted and relaxed, adapting.

I positioned the anal fingers downward, the pussy fingers upward.

The sensations from both felt through the dividing wall.

Moving both hands in unison felt like I was holding onto Shin Ah-young’s flesh.

「That…feels weird. Inside meeting…rubbing. Hnn…♡」

It was the first time feeling this, but the moans that began to escape suggested it wasn’t bad.

Increased the rubbing speed of the sticky, clinging walls.

「Ah..♡ Slow down a bit..♡ Kyahh♡ Hnn..♡」

Her voice sweetened.

Now the finger alone seemed fine, moving without any trouble.

Drops of fluid began to fall onto the bed sheet, and a naughty sound emitted from the anus.

Pushing the momentum, I moved faster and both holes tightened.

As I struggled to move my hands, I ended up stimulating the walls in place.

「Aah…♡ Hnn… ♡ Hoo…eek..! Aah..♡」

Fwooosh…Fwooosh..

It didn’t take long before climaxing in a gush.

The arms spread wide on the hips relaxed and crashed onto the bed.

Noticing something while watching her abdomen rise and fall.

The oil applied during the enema had washed off.

That meant she had cummed without the slight help of the the oil.

Indeed, there was talent here too.

Looking at the still twitching hole, it seemed inadequate for my cock still.

I got up from the bed and wrote on a piece of paper, showing it to Shin Ah-young.

[Bring out the anal plug we bought last time.]

「Yes… It should be in the second drawer where I took out the enema kit earlier.」

Catching her breath, she sluggishly got up to open it first.

Stored alongside adult toys were dildos, anal plugs, and even a cat tail among other items.

I took them all out at once and placed them on the desk, she hurried over.

「Oh, no. Why take all these out? So embarrassing..」

Then, she put everything back except for the anal plug.

Already having had sex, didn’t see what was so embarrassing.

「And I haven’t used these things in a while. Mr.Ghost’s cock feels the best..」

She whispered softly as I looked on, then she turned her head quickly.

If that was true, then my cock was the only thing that had been in her pussy recently.

Might be an overinterpretation, but does that mean she hasn’t even masturbated?

Regardless, good to hear that my cock feels the best.

Tapped on a chair to indicate her to sit there.

As she approached, turned her body around to sit backward.

Pressed her chest against the backrest and pushed her hips back, exposing two holes perfectly outside the chair.

I massaged her ass cheeks while applying oil to the anus.

The folds relaxed a bit and slightly opened up.

I seized the moment to insert a finger inside and apply the oil.

「Haah..♡ There it goes… Hee♡ Inside too.. Hoo♡」

While intensely rubbing every nook and cranny, the pussy hole fluttered but I ignored it.

The purpose was to let her know the anus was becoming sensitively pleasant.

「Hnn…♡ Feels good there♡ The ass hole is getting more sensitive..haah♡」

Once I could easily insert and remove the index finger, I added the middle finger.

「Aah…! Wait..two is..♡ still..」

Despite her words, it didn’t seem painful.

Instead, she pushed her hips further back to welcome me more.

Squishing sounds followed.

It wasn’t long before erotic sounds began emanating from the anus.

I looked up at her.

She was tightly pressed against the chair, her breasts crushed.

While observing her reactions and rubbing various parts, most moans were soft, but she especially enjoyed it when I touched the side that was connected to her pussy.

I wondered how sensitive the pussy walls could be to react like that.

Gradually, two fingers also became an easy insertion.

I pulled out my hand and picked up a spade-shaped anal plug.

The hole, emitting a naughty scent, stayed open.

After applying oil to the plug, I positioned it against the opening.

As she felt the cold metal, she looked back with a slightly anxious gaze.

Looking at her face once, I started to push with force.

「Hnn… ♡ Hoo…eek..♡ It’s cold..!!」

Once the thickest part was in, the rest followed swiftly.

With a pop, the plug settled in.

Instead of the reddened hole, a pretty heart-shaped decoration was now visible.

As the plug went all the way in, Shin Ah-young swayed her hips, enjoying the sensation of the plug.

Seeing that, I couldn’t hold back.

Even after taking the vigor pill and only having foreplayed up till now, I was ready to pull out.

I saw her pussy dripping juices on the floor.

Inserted my cock straight into the dripping, honey-filled opening.

「Aaaah♡ The cock…you should’ve said before inserting♡ I was focusing on the ass hole..♡」

It went in all the way in one go since it was already thoroughly wet.

It felt hot and sticky like usual, but the sensation was different because of the anal plug.

The inner pussy tightened, touching the top of my cock providing a novel stimulation.

「Both holes at once..♡ Go harder…fuck my pussy♡ Touch the plug too…quickly♡」

The excitement of having both holes filled made her fondle her breasts and beg intensely.

I thrust against the entrance of the uterus, turning the plug counterclockwise with my right hand.

「Aah…♡ I like that♡ More…don’t stop♡」

Her voice grew more desperate.

I too wanted to climax, so I increased the pace.

「Here I go♡ Getting fucked in both holes♡ Here…here it goes..♡♡」

I timed my climax with hers, gripping the anal plug tightly.

And as the pussy began to squeeze my cock, I pulled out the plug.

Pop!

「Aah..♡♡ Kyahh♡♡ Aah…♡ Hoo…」

A tremendous moan escaped her as she climaxed grandly.

I had only been stimulating the anus and clitoris, so the built-up pleasure burst out all at once.

I inserted my finger into the gaping ass hole.

The moment I touched it, it twitched and clenched but didn’t stop me.

Seeming ready to climax again, I quickly started piston her anus with my finger.

Pressing my finger down hard, I could feel my cock.

Continuing to stimulate it brought desperate moans from the front.

「I’m…♡ there…gone! Doing that…cumming again♡ The pussy is cumming too..♡」

Her convulsions intensified, and she clamped down with her pussy painfully.

The pussy that had just climaxed squeezed tightly, milking my cock.

Brrrrt…

With the tremendous constriction, I climaxed together with her.

She, seemingly in the throes of continuous orgasms, squirted pussy juice on the floor, forming a puddle.

I wondered if this would leave a scent on the wooden floor.

「Heh…heh…♡ The ass hole…doing it together feels twice as nice♡」

She clung to the backrest, calming her body down.

Having recovered, she sat up straight again, leaning forward and putting her face near my cock.

「It’s still hard♡ But my ass hole has only been fingered so far…now slowly.」

She sucked off the semen at the tip of the urethra, a hopeful expression on her face.

Seems she realized the anus felt good.

After cleaning up diligently, she headed back to the bed and lay down, staring at the ceiling.

Pushing her asss as far forward as possible to make the holes visible, she grabbed her thighs and spread them.

This position was erotic, but it seemed less painful to do it in a doggy style, so I wrote on a piece of paper and showed it to her.

[It might hurt less from behind.]

「I want to see it directly when you break my anal virginity… Please, go ahead.」

Her firm determination showed, so without further words, I climbed onto the bed.

I positioned myself and aligned my cock at the entrance of her hole.

「Please… slowly insert it.」

Even with slight pressure, it repeatedly slipped out.

Realizing it might not work without more force, I steeled myself and decided to thrust harder.

Just the tip, not too much.

I gripped her thighs tightly and pushed in all at once.

「Aaah…! Hoo… Ahh…」

Screams of real pain echoed.

Looking at her face, tears welled up and she bit her lip, enduring the pain.

Given the thickness of my cock compared to a finger or an anal plug, it was inevitable.

I waited patiently, and she sobbed softly.

「It’s hot…and hard…and painful..」

Seeing her in pain, but knowing the thickest part was in, the rest should be more manageable.

I massaged the clitoris to help ease her tension while giving her time to adjust.

After a while, her face improved as the pain subsided.

She spread her thighs wider and said,

「It’s okay to put in more now. Since it’s my first time… don’t stop midway, go all the way.」