Did You Know That a Playboy Can Change His Job to a Sage? – 19

The Playboy and Tentacle Play

TN Note: Don’t read this chapter at work.

Immediately after entering the forest, we encountered a monster.

Nyannyan told us to “Stop, stay low” as she raised her hand.

Then, she turned around and whispered.

“…Look at that tree, nya.”

I nodded, replying with a whisper.

“Mmm… Oh, a man-eating tree, huh? You saw it straight away, as expected.”

The tree-like monster was to the right of the path we were taking, it was mimicking the fauna so well that it would be difficult to tell at a mere glance.

Tina’s eyebrows raised in admiration.

“Amazing… I couldn’t tell at all!”

“Look at the tree roots. They’re wiggling a little bit, just like a tentacle, see?”

Tina squinted her eyes as she looked.

“Wow, it’s true! That’s gross!”

“You’ll get caught by that thing if you don’t keep an eye out, so pay attention.”

“Eh, really!?”

“Men and women both.”

“Ehhh!? …Dylan-san, by any chance are you into that kind of tentacle play?”

“Are you an idiot?”

As I laughed through my nose, I began to imagine what it would be like if Tina and Nyannyan got caught by that man-eating tree.

Hanging upside down in the air, their clothes and armour peeled off, the tentacles writhing all around them…

playboy 11

“…Dylan-san? Why did you suddenly go silent? No way, are you…?”

“M-master? Is that one of your hobbies, nya…?”

As their faces went red, I smiled.

“Not bad at all.”

“Not bad he saysー!Jeez, Dylan-san, you perv!”

“Nyaa! Being fantasized about is even more embarrassing than I thought, nyaa!”

“I’m just kidding. In gratitude for that pleasant little day dream, I’ll defeat that thing for the lovely young ladies☆”

I gave them a signature playboy smile. That should knock ’em dead.

But, their faces just got more flustered.

“Not apologizing for his delusions, just thanking us, Dylan-san is really the lowest of the low…”

“He really is a playboy, nya… How did we fall in love with a man like this, nya…?”


They’ve become kindred spirits.

“True friendship really is a beautiful thing to behold. Now then, I’ll be back in a second.”

“It’s just that we have a common enemy.”

“Good luck out there, master. I’m expecting some tentacle play, nya.”

Don’t get your hopes up.

I got up and slowly walked down the path, pretending that I hadn’t noticed the man-eating tree.

“Funfufu~n ♪ Ahh, there’s nothing better than a peaceful walk in the forest.”

I raised up both my arms, stretching out my back.

As soon as I did, the ground near me began to shift like snakes were slithering through it.


The roots of the tree burst through the ground. Yep, tentacles.

From the trunk of the tree, a large vertical eye opened up. It finally revealed itself.

I jumped away to avoid it easily, then as I held my hat in place I stuck out my right index finger.

Time for that really basic magic again――


Even if it’s the lowest class of magic, it can still produce a fireball as big as a person.

But, this is a tenth-floor monster. It seems like it has a counter for it.

Shashashasha, the tree roots came together to form a wall in front of the man-eating tree. There’s no way I can get a hit in like that.

The tree’s eye seemed to be laughing at me. When I saw it, I laughed as well.

Just as I thought.

The tree root wall began to fall down. It really didn’t have any means of escape.

And then, the wall collapsed. A thunderous thud echoed through the ground and a cloud of dust was chucked up. As the tree was focused on me in the sky, it had been hit by a very powerful attack from below.

When I had raised both hands before, I’d dropped a whole deck of playing cards.

Using a magic trick, I swapped my position with those of the cards that had sliced through the tree, pointing my index finger right at its eye.



The man-eating tree had no idea what had happened. As it got hit directly with my magic, it burned to ash, fading away and leaving only a manastone behind.

I could have defeated it without using magic, but it was more fun this way.

“As expected of Dylan-san!”

“Master really is strong after all, nya!”

As I bent over to pick up the manastone, the two of them emerged from the bushes with a cheer.

Whisking the manastone in my hands away to storage with a trick, I noticed that the two of them were staring at me bashfully, melting a hole in me with their eyes. Eh, what is it?

“Umm… So long as Dylan-san saves us and no one else sees… If you really want to, maybe doing a bit of tentacle play isn’t so bad…?”

“Nya… Me too… So long as Tina is fine with it, it should be okay, nya…?”


For a moment, I seriously considered it. The manliest part inside of me was considerably stirred by the idea.

“Don’t be stupid. I can’t put my lovely companions in such danger, can I? ☆”

I somehow managed to hide my true feelings by flashing them another playboy smile.

Tina and Nyannyan nodded, I thought they would be relieved but they actually looked a little disappointed. Eh, did I make a mistake…?

“…..Let’s keep going. Be ready for anything.”


“Nya, l-let’s go!”

What is this atmosphere?

After that, we encountered another man-eating tree.

Tina, in her role as tank, stood in front of us and took on all the attention of the tentacles.

They gripped around her shield, stomach, thighs and left arm, but Tina didn’t budge. She made sure to keep her neck and sword arm protected, so she was fine. The man-eating tree tried to lift her into the air, but her poise was too strong.

Then, Tina looked at me. It must have been because of the mood from before, but my imagination had been sparked when I saw that. ‘Should I stop resisting?’ she seemed to ask me with her eyes, but I’m sure I was mistaken.

As Tina took the monster’s attack head-on, Nyannyan darted at the base of the tree with her knives and plunged them into its eye.

The man-eating tree flailed its tentacles wildly in a painful panic.

Nyannyan glanced at me quickly. The look she sent me seemed to say ‘What kind of perverted attack are you hoping for, nya? Armour break?’, I want to believe it was just my imagination running wild. I really want to believe that.

Before long, we’d already cut down our fifth man-eating tree, obtaining a large number of manastones.

“Things are going great!”

“Yes! It’s great! …..Things are going really smoothly.”

“Really smoothly, nya! ……….Nothing happened.”

As those girls muttered with disappointed voices, I pretended I didn’t hear anything.



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    1. Agreed. After seeing the illustration in the illustration page i thought they would be captured but nope, what a trap. Also really funny that the girls are disappointed at the end.
      Thx for the chapter.

    1. I feel it’s more like jester cause Dylan to have erotic screw loose and then he trained this two well in a few days… What a monster. Tina was pure and innocent. Well pure types easily to taint.

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