James's Favorite Plaything

"Agh! James! St- AH!" He did it again. I can feel the painful tingling sensation that his hand left, but I like it. I never thought I would, but I do.

He smirks and chuckles. "You like that, huh?" He smacks me again and I grip the pillow tighter with a whimper. "Y-yeah..." I murmur.

My body shakes with anticipation, waiting for him to hit me again, but all he does is rub my ass with his hand.

He bends over me and nips and kisses the back of my neck. Everything he does makes me crave more. How the hell is this bastard so good at what he does? I don't care, as long as he keeps doing it.

"Y'know..." He murmurs against my skin. "I think..." He trails off again to kiss my shoulder. "I wanna fuck you in the ass."

I don't process his words until I feel his fingers probe at my hole.

"Whoa, James, wai-"

"Be quiet." He growls, landing another hard smack on my already red bum. Goosebumps rise on my skin, both from pleasure and from nerves.

I bite down on my bottom lip in anticipation. I had never had anal before, and never even really thought of it, but the idea is exciting and nerve-wracking at the same time.

James continues to kiss my neck, using his free hand to tilt my head. "Relax, Matty." He whispers. "Trust me. It's gonna feel reeaal good."

He spits into his fingers and begins to rub it along my tight hole. I suck in a sharp breath and squirm beneath him, but he keeps me firmly held down. Before I know it, I can feel the tip of his cock rubbing along my asshole.

"J-James-"

"Bite the pillow." He tells me.

I hesitate for a moment, but I do as I'm told, and before I even realize it, he begins to ram his cock into my ass. I bite down hard on the pillow while his throbbing member stretched out my tight hole. Muffled whimpers of pain escaped my mouth as my hands clawed the sheets.

I let go of the pillow with a gasp. "James, p-please...it hurts." I whimper.

His hand rubs my back to get me to calm down. "I said relax." He whispers.

Slowly, I take in a deep breath and relax my body beneath him, nodding for him to keep going.

He starts slow at first, but his pace quickly picks up. As he fucks me, he reaches up and pins my arms again. His cock stretches me more than I thought I could take, and after I finally adjust to his size, it starts to feel really, really good.

"Oh fuck...aaahhh~ haahhh~ James..." I moan loudly.

"Well, well, look who likes to take it up the ass." He smirks. He keeps both of my arms pinned with one hand while his other snakes down my body until it reaches my pussy. I feel two of his fingers slide into my soaking cunt and curl to rub my g-spot.

I gasp and tense. "Fuck...James...you're- mmph...you're gonna make me cum..."

"So soon?" He asks as he leans down close to my ear. He slips in a third finger and rubs on my sweet spot harder. "Good." He hisses.

He fingers me hard and his thrusts begin to speed up. My grip on the sheets tightens when I feel that pressure suddenly begin to build.

"Fuck, J-James, I-I'm- Aahh~ Oh fucckk~" I groan loudly as I bury my face into the pillow. My orgasm hits me harder than I expect it to, my walls tightening around his fingers. He pulls them out and licks my juices off them, but his thrusting doesn't stop.

He fucks me hard all throughout my orgasm, leaving me to lie here, completely helpless as his cock ravages my ass.

"That's it. Now it's my turn." He speeds up, his thrusts becoming faster and harder. He reaches and tightly grips my hair, pulling it hard and forcing my head back.

"Fuck! James...Aahh~ Haahhh~ Oohh~" I whimper and moan, my head becoming cloudy with the pleasure.

Soon, I feel his hot, sticky cum filling my ass. I grip the pillow while he rides out his own climax, and when he's finally done, he pulls out.

"Fuck...James..." I whimper quietly, gasping to catch my breath.

He smirks and watches as cum drips from my stretched hole. "Look at that. You like having your ass filled with cum, don't you?"

All I can do is not.

He flips me back over onto my back and presses his lips to mine. I sigh against his mouth and pull him closer to me.

We spend the rest of the night like that; exhausted, sweaty, and satisfied.

The next morning, I find Gael on my couch. "You seem like you had a lot of fun last night, Mr. Hickey." She muttered.

"Oh...yeah...that...Uh...did you have any luck with Helen?"

"No! Turns out she's straight! AND married! Ugh." She sinks into the couch and continues to munch on the potato chips she stole from my cabinet.

That was how my night went. I must admit, I do spend the next few nights touching myself to the thought of getting fucked in the ass again.