Issei no longer hesitated.
He unzipped his trousers and freed his already rock-hard cock, the thick length springing out into the open air.
It was massive, far larger than any girl would expect from someone his age and already glistening with precum at the swollen tip.
"You asked for this, Rias-senpai. I'm going to fuck you so hard that you'll regret every second of trying to manipulate me into it."
He spun her around, pinned her against the nearest surface, and positioned himself behind her.
Without any further warning, he lined up the swollen head of his cock against her entrance and pushed in.
Rias gasped sharply as her hymen tore around his massive size.
The sudden stretch was overwhelming, a sharp flash of pain that made her whole body tense.
A thin trickle of crimson blood ran slowly down the inside of her pale thigh, marking the loss of her virginity.
"Issei-kun… this is too fast… We should have done proper foreplay first…" she breathed, her voice trembling with a mixture of pain and reluctant pleasure.
Issei only chuckled darkly, already buried halfway inside her tight, virgin heat.
Her inner walls clutched at him desperately, squeezing and fluttering around his invading length.
"Well, I'm not so sure about that. In all the porn I've watched, they always skip straight to the main event. What could possibly go wrong?"
He gave another slow, deliberate thrust, forcing more of his thick cock deeper into her clenching depths.
She moaned despite herself.
"Just relax, Princess. Since you're supposed to be much stronger than me and you have that fancy transformation ability, why don't you use it? Temporarily, of course. Just to make sure everything feels good for both of us."
Rias rolled her eyes even as another soft, breathy moan escaped her parted lips. "Pervert… Why don't you just be honest and admit that you want to see me in my devil form while you're fucking me?"
He didn't deny it.
Not even for a second.
Instead, he simply kept pushing deeper, stretching her tight, virgin walls around his thick cock with slow, steady, relentless thrusts.
Each movement sent shivers of pleasure and pain racing through her trembling body.
She moaned again, her voice already turning breathy.
"Ah… I think you're right, Issei… Let me transform. Then you can fuck me harder."
Dark, leathery wings suddenly burst from her bare back, the transformation flooding her body with demonic energy.
Her aura shifted, becoming darker and more powerful.
Her eyes glowed faintly crimson.
The moment the wings fully formed, Issei grabbed one of them tightly with his free hand, his fingers curling around the sensitive membrane, and grinned with pure, unadulterated lust.
"As you wish, Princess."
He slammed the rest of his thick cock into her in one powerful, brutal thrust, burying himself to the very hilt inside her newly transformed body.
"Ah...!"
Rias screamed, her voice echoing through the private room.
But it wasn't a scream of pain.
The transformation had flooded her entire body with heightened demonic sensitivity, making every nerve ending fire with electric intensity.
Every trace of discomfort vanished in an instant, replaced by overwhelming, mind-numbing pleasure.
Her newly awakened senses made every thick, pulsing inch of him feel good, so good that she could barely think straight.
Issei savored the sight of her bare devil form beneath him, the large, leathery wings spread wide, the subtle shift in her aura that made the air crackle with power, the way her full, soft breasts bounced and jiggled with every powerful impact.
He began pounding her hard from behind with merciless, unrelenting rhythm, his hips slamming against her round ass with enough force to make the desk shake.
The wet, lewd, obscene sound of his thick cock slamming in and out of her freshly claimed pussy filled the entire room, mixing with her breathless moans and his low, guttural groans.
He had wanted this for so long.
And now that he finally had her, the beautiful, proud, untouchable princess of the Kuoh Academy, he intended to enjoy every single second of it.
Of course, Issei had no intention of limiting himself to just her pussy.
Since Rias had offered him every virginity she had, he fully intended to claim all of them. After several deep thrusts into her cunt, he pulled his thick, glistening cock out with a wet sound and pressed the swollen head against her tight, untouched asshole.
The puckered ring of muscle twitched nervously at the contact.
He pushed forward without hesitation.
Thanks to her devil transformation still being active, Rias barely felt any real pain as his thick shaft slowly, insistently forced its way into her virgin ass.
The heightened demonic sensitivity that flooded her transformed body turned what should have been sharp, tearing discomfort into a strange, overwhelming sensation of fullness that made her toes curl and her breath catch in her throat.
Her inner walls stretched around him, accommodating his massive girth far more easily than any human girl could have managed.
That was absolutely perfect for him.
It meant he no longer needed to hold back or be gentle.
Issei began alternating between her two holes with practiced rhythm, slamming into her dripping pussy for a dozen hard, brutal strokes before pulling out and burying himself deep in her ass, then switching back again without missing a beat.
The wet, filthy, utterly shameless sounds of his thick cock plunging in and out of both of her holes filled the private room, echoing off the walls in a symphony of depravity.
"Gaagh…! I'm cumming…! Cumming again…!" Rias screamed, her voice breaking and cracking as yet another powerful orgasm crashed through her trembling body.
Her inner walls spasmed and clenched around him, milking his cock desperately.
"I'm close too, Princess." Issei licked his lips hungrily and delivered a sharp, stinging spank to her bouncing ass, watching with satisfaction as the soft, pale flesh jiggled under his palm. "Do you want it inside or outside? Your choice."
Her ass clenched rhythmically around his thrusting cock as she moaned loudly, her voice thick with desperate need. "Inside…! Please cum inside me, Issei…! Fill me up completely…! Don't leave anything for that good-for-nothing fiancé of mine!"
He smirked wickedly, his eyes dark with possessive hunger. "Good girl… That's exactly what I wanted to hear."
He grabbed her hips with both hands, fingers digging into her soft flesh, and pounded into her with brutal, unrestrained force.
Rias's eyes rolled back in her head as the rough, punishing thrusts pushed her over the edge yet again.
At the exact same moment, Issei buried himself to the absolute hilt and erupted with a guttural roar, flooding her insides with thick, hot, endless ropes of his potent cum.
Their orgasms crashed together like colliding waves, leaving both of them shaking and gasping for air.
Rias collapsed forward onto the desk, her chest heaving, her legs trembling so badly she could barely support herself.
When she finally mustered the strength to look back at him over her shoulder, her gaze immediately dropped to his cock, which was still rock-hard and glistening with the mixed evidence of their passionate encounter.
A slow, wicked smile spread across her swollen lips, and she licked them deliberately.
"Well… it seems you still have quite a bit of stamina left, Issei Hyoudou. I'm impressed." Her eyes gleamed with renewed hunger. "Do you want me to help you with that?"
Issei stroked his thick, slick length once, letting out a low groan at the sight of her thoroughly ruined, cum-filled holes. "Yes, Princess. Get on your knees. Lick it clean. Make it yours."
Rias smirked with pure, unadulterated wickedness as she pushed herself off the desk and gracefully dropped to her knees before him.
"As you wish… my prince charming."
She opened her mouth wide and took him between her soft lips without a moment's hesitation.
Her tongue immediately went to work, swirling around the sensitive head before sliding along the full length of his shaft, cleaning away every trace of their mixed fluids.
Issei grabbed a fistful of her crimson hair and began thrusting into her mouth with the same brutal intensity he had used on her other holes, treating her throat like just another tight, wet pussy to be conquered.
Wet, choking, gagging sounds filled the room as he fucked her face without mercy.
Her eyes watered.
Her mascara ran.
But she never pulled away, she simply looked up at him with those adoring eyes, submitting completely to his dominance.
It didn't take long before he groaned deeply and unloaded again, flooding her throat with another thick, hot load of his seed.
Rias swallowed greedily and eagerly, her throat working to take every last drop, not letting a single bit escape past her lips.
Life was pretty damn good when you were Issei Hyoudou.