Chapter 22

Riley

The sound of a drawer opening was enough to rattle my senses. I couldn't help myself as I turned to look and saw that he was grabbing a bottle of lubricant out of the nightstand next to the bed.

The fact that my ass was already sore from the spanking he had given me wasn't lost on me, and my heart thudded in the back of my throat as I obeyed him and rolled over. As my belly pressed against the bed, a sudden burst of nerves rolled through me, and it was hard to breathe for a long moment.

"This is going to hurt, little girl. I know my cock is too big for that tight little hole, but you're going to come very, very hard for me by the time I'm through with you," he said darkly, and my hands fisted tightly in the blankets beneath me.

"You don't have to fuck me there," I attempted one more time to negotiate, but his soft answering chuckle was enough to send a shiver of anxious need rocketing straight down my spine. My pussy clenched hard as I pleaded. I knew that I was about to get my ass fucked no matter what I said.

"Daddy is going to take that virgin hole whether you like it or not, sweet girl, but I have a feeling you're going to like it very much," he said, his words reassuring at the same time as terrifying.

As if he knew I was panicking a little, his fingers grazed lightly up and down my spine.

"Lift your hips, baby girl," he dictated, and I hesitantly obeyed him. He slipped something smooth underneath me and then I saw a small remote in his hands. He flicked it on and suddenly the object roared to life.

The vibrations nearly tipped me over the edge, but then they tempered down to a slower, more teasing rhythm.

Maxim ran his hand down the length of my spine and cupped one of my cheeks in his palm, squeezing roughly and I groaned, the pain mixing with the pleasure. Then he roughly parted my cheeks and squirted a dollop of lube directly on top of my asshole.

It was cold, but I didn't dare move.

The vibrator between my thighs continued its slow relentless rhythm. It wasn't enough to make me come all on its own, but when his fingertip pressed against my asshole, the anticipation of being taken there was enough to send a visceral surge of pleasure straight to my clit.

I didn't want it to feel as good as it did.

His fingertip circled my tight rim, spreading the lube across my already punished hole before he gently started pushing a single digit inside me. I balked at first, but his firm hand on my back held me in place.

It didn't hurt, not really, but the burn was still there, and the sensation was strange and different.

But then, the vibration between my legs changed pace, the tempo increasing slightly, and I groaned. He pushed his finger deeper inside of me and I bit my lip, trying to keep calm while also burning up from the inside out.

Soon enough, the vibration between my legs slowed, and I found myself relaxing just a little, but then Maxim added a second finger, and it was enough to stretch my asshole enough to burn.

I tensed, which only made it hurt worse. As much as I tried to relax, it was infinitely difficult. Gently, he pumped his two thick fingers in and out of my reluctant hole and very slowly, the stinging pinch started to fade.

The vibrations started up again once more, gradually, but persistently until I was on the edge of orgasm.

"Not yet, little girl. I want to feel you come with my cock deep inside this tight ass and not a second before," he demanded, and a flash of ecstasy rolled through me before the vibrations lessened once again, but they didn't stop.

He kept fucking me with his fingers, slowly and methodically stretching my virgin ass. When he eventually added a third finger, the pain began all over again.

And then something occurred to me.

His cock was so much bigger than just his fingers, which meant that it was going to hurt that much more.

All at once, I clenched tight and pushed against the bed, but he easily overpowered me and pinned me to the bed. As punishment, his gentle fingering turned a whole lot rougher.

I keened, the burning pinch almost more than I could bear. The vibrations rose to a fever pitch, and I was on the edge of orgasm before I realized what was happening.

"I'm sorry, Daddy! Please!"

"You're going to be a good girl and take Daddy's cock in this tight little hole, or I'm going to tie you up and put you to bed wet and needy without letting you come at all," he scolded, all while he roughly fucked my asshole with his fingers.

With a sharp desperate cry, I begged him to do the thing I never thought I'd do.

"Please, Daddy! Please let me be your good girl. Please fuck my ass," I pleaded. He chuckled, but his fingers didn't slow.

Then his voice came, dark and foreboding, and it sent a shiver of anxious need spiraling straight through me.

"I'm not sure you're quite ready for Daddy's cock, little girl, but since you've begged so very prettily for me, who am I to deny you," he replied and the warning in his tone made my bottom clench hard around his fingers.

Gently, he pulled his thick digits free from my ass.

I breathed a sigh of relief, but then he pressed the blunt tip of his cock against my well-prepared hole, and I tensed.

My hands fisted in the sheets, and I bit the inside of my cheek as the head of his cock pushed through my tight rim of muscle.

Oh, my god.

His cock was pushing inside of my ass. In just a few moments, he would be all the way inside of me and then I would be getting my ass fucked for the very first time in my life.

I moaned.

I panicked.

I fought against him, but he held me down and pressed one thick inch after another inside of me. He stretched me so much wider than his fingers had, and the burn was unlike anything I'd ever experienced before. I felt it deep in my core and it pinched so hard that my entire world became a black void of pain.

And then he thrust all the way inside me in one hard stroke.

I screamed, and then the vibrations ramped up again. I was on the cusp of orgasm before I could really think about it.

"Daddy!"

"That's it, little girl. You're taking Daddy's cock in this tight hole so very well. I'm so proud of you," he praised and just like that, the pain seemed to lessen, and pleasure billowed through me like a sandstorm.

His hand wrapped around the back of my neck and pressed my face down against the bed. With a moan, he drew his cock out and then shoved it back inside of me and the pleasure and pain combined was so intense, it was almost more than I could take.

Then he started to fuck me.

Not like any of the times before.

He fucked me.

Punishingly hard.

Then the vibrator turned up between my thighs.

My clit pulsed, and then I was falling with no end in sight.

I couldn't stop myself. My orgasm tore through me.

It was the most intense thing I had ever felt. Every single nerve ending between my legs was ablaze and as Maxim fucked me harder and faster, the vibrator on my clit kept going and going and going and then my head soared up into the clouds, higher and higher until I lost all control.

I came so hard that my moans morphed into screams and then I knew nothing but pain and pleasure and everything in between.

A whirlwind of sensation swept me off my feet and then my orgasm was cresting and there was another one waiting in the wings.

I feared it, but there was no way to stop it from coming. It was unlike anything I had ever experienced.

I screamed and thrashed and moaned, my entire body shaking and trembling as one orgasm after the other slammed into me.

Somewhere along the way, the vibrator turned off and his fingers replaced it. They were rougher than they had ever been, forcing my orgasm to come to a head as he drove into me, over and over.

"It hurts," I whined.

"It's supposed to, little girl. Daddy's too big for this virgin hole, but you're going to be a good girl and take it. You're going to be so good for Daddy, aren't you?"

"Yes, Daddy," I wailed.

He fucked my bottom so hard that tears edged the corners of my eyes. I didn't want to cry again, but I had a feeling that I wasn't going to have a choice.

With each heavy thrust, he drove into my ass as he toyed with my clit, playing my body like a violin as he forced one devastating release after another through me.

I quickly lost count. They came one after the other. It was a never-ending relentless assault.

I couldn't catch my breath.

I couldn't think.

My world was an ocean of pleasure and pain, and I wanted it to end at the same time that I didn't. I begged and pleaded, but soon enough, the sounds leaving my lips became nonsensical. All I could focus on was his thick cock, the soreness in my asshole, and his fingers on my clit.

I came.

I screamed.

I lost all sense of reason.

"I want you to remember this moment, little girl. I want you to think about my thick cock punishing this naughty ass any time you even consider lying to me again. I want you to remember how much it hurts, and how every orgasm is more painful than pleasurable and how sore your beautiful body is going to be by the time I'm through with you."

I realized something just then.

My punishment hadn't ended with the ginger.

I whimpered as he thrust into me impossibly hard, so hard that the tears in my eyes began to fall and then I was sobbing. One tear after another flowed down my cheeks and before I knew what was happening, another orgasm ripped through me like a hurricane.

I came so hard my vision whited out.

Then I collapsed on the bed, utterly spent, but he wasn't done with me. He fucked me until I couldn't breathe, until my entire body was racked with sobs and then he fucked me some more.

"I want you to remember that Daddy loves you no matter what and he won't hesitate to remind you of that as many times as you need," he continued.

Each orgasm after that wrecked me.

By the time he was finally through fucking me, I was an oversensitive weeping mess, and then with his cock fully inside me, he forced me to come one last time.

I was vaguely aware of his seed spurting inside of my asshole, but as I detonated, I found my mind suddenly wiped clean.

I came so hard I blacked out.

I woke up sometime later with his arms wrapped tight around me.