My Harem Academy

Midnight put her legs on Takashi's chest, who, in the meantime, generously lubricated his cock with secretions from her pussy, and put the tip against her anal-hole entrance.

"Wait!" she said, causing Mitarai to freeze.

Blushing so much that her skin was almost the same color as a tomato, Midnight continued; "This my first time doing anal!! Please be gentle…"

Such a cute blush on Nemuri Kayama's beautiful face made Mitarai get even more excited.

Barely holding back the impulse of lust, he carefully moved forward, and after a few moments, he was able to penetrate past the ring of Midnight's asshole with a ~PLUNG~, causing her to moan loudly.

He immediately continued to push his cock inside Midnight's ass, strongly stretching her virgin anal passage.

"Ahhh, Mitarai! You're so big, so thick! You're stretching my virgin asshole so much!" Nemuri was moaning all this time, her eyes wide open, watching her lover take her butthole for the first time.

"Mmm, Nemuri-sensei!" Mitarai moaned when his cock was completely dipped in the milf's ass.

"This is incredible! Your ass is squeezing me so hard!" he added.

Feeling a superbad pleasure and pride from depriving the R-rated hero of the heroes community as he took her anal virginity, Mitarai blushed slightly and added:

"I-I love you so much, Nemuri… Especially the depraved side of you!!!"

"I love you too, Mitarai-kun!! You make me so happy, you make me feel so good" she replied, meeting his gaze and giving him a smile full of happiness, which after a few moments turned into a wide, lustful grin.

"Now, how about fucking your lustful sensei's ass and make her feel good from behind? Mark my last hole as your property," she practically demanded with a seductive grin that no man would reject.

Finding Midnight's demanding tone extremely sexy, Mitarai hastened to comply with the order.

He slowly pulled back, leaving only the tip inside Midnight's anal, and then abruptly pushed his cock back inside.

SMACKK!!

The way Nemuri moaned in pleasure and her body trembled made the high school boy continue his thrusts pushing even deeper.

Grabbing her voluptuous hips with his hands, Mitarai began to fuck the Hero-Milf in the ass.

Again and again, Takashi pushed his dick inside her ass, causing her to moan and scream loudly.

SQUIRTTT!!!!

Meanwhile, her neglected pussy was oozing with love juice with all its might, which then flowed down to her anus, and made penetration easier, allowing him to move even faster and harder.

"So good!!! Ahhh! Yes!" the seductive sensei moaned lewdly, rolling her eyes and blushing.

"Fuck me, Mitarai-kun! Fuck my ass with your huge thick cock! You're so deep inside my virgin asshole! Don't stop! Don't you dare fucking stop! Fill my bitchy ass with your semen! Cum inside my ass as much as you want!" she roared lustfully saying naughty words she normally wouldn't say.

But now, hell she was at the highest kingdom of ecstasy.

The depraved moans and Nemuri's anal ring squeezing his shaft hard made Mitarai groan.

The incredible excitement and unimaginable pleasure he felt while fucking her tight ass brought the boy closer to eruption.

With each thrust, each minute, he grew closer and closer…

Feeling this, Mitarai directed his hand to Midnight's smooth pussy and began to viciously rub her engorged clitoris.

"Ahhh, Mitarai-kun such a big boy you are!!! Having your way with your own senseiii… ahhh fuck~~~!" Nemuri immediately screamed.

"You're driving me crazy! Fuck my virgin butthole! Caress my wet leaking pussy! Don't stop! Keep fucking me~~…"

With each penetration of Mitarai's penis into her hole, and with each touch of his fingers to the pea of ​​her clitoris, the woman was more and more lost in pleasure.

His huge fuck meat was destroying her tight asshole just like with her pussy before, leaving no chance that anyone except him could ever satisfy her.

And she was delighted by this. Her eyes rolled back, and her tongue left her mouth, open in a scream of ecstasy.

After some time, the heat building up in her lower abdomen became unbearable, and she could not stand it.

"Ahhh, Mitarai! I can't take it anymore! I'm going to cum now! Your huge cock in my ass is going to make this old woman cum now!" She moaned feebly.

SQUIRTTT!!

SQUIRTTTT!

SPULUSHHH!!!

The next moment the girl was convulsing in a powerful orgasm. The ring of her anal squeezed hard around Mitarai's shaft, and this was the last straw for him.

"Sen--sei! I'm cumming!" He screamed loudly, and thrusting his cock deep into Nemuri's asshole, he began to fill her up with his thick, hot sperm.

SLURTTTTTTTT

SPURTTTTTTT

SPLRRRRTTTTT

SPPPPURRRRRRRRRRTT

'Inside my ass! Ahhh so gooooooooood!' flashed through the head of Nemuri, writhing in pleasure.

While Nemuri was enjoying the waves of ecstasy, Mitarai finished pouring his thick juice inside her, and for a while, he simply watched the expression of bliss on her beautiful face.

When Midnight had completely calmed down, he slowly pulled his cock out of her asshole, allowing the cum that was there to gush out with ~SPLURTT!~.

"Mmm, no, noo, I don't wanna, no!! I want that warmth inside not outside" Midnight moaned grumpily, having lost the source of pleasure, to which Mitarai only grinned.

"That was amazing, Mitarai-kun" she whispered and kissed him tenderly.

"Yeah way too good," Mitarai replied, and then added, "Seeing you disheveled, half-naked, and with my cum flowing out of both of your holes is absolutely unforgettable," the Highschool boy said with a smirk.

"I'll be happy to appear before you like this many… many more times," Nemuri purred seductively.

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