Annie Night 01 - Initiation

"Mmm! That one hurt!" She exclaims.

"Shut your mouth and take what you deserve. These last few are going to hurt, but it will be worth it. Good subs are thankful, even during their punishments."

She nods and buries her face and mouth into the comforter. Her arms fully extended forward in front of her.

*clap*

Same strength as the last. My hand begins to sting. A yelp followed by a deep grunt from Annie is voiced into the bedding.

*clap*

Slightly harder. I do not take my punishments lightly. This time, her yelp loudly makes it out of her mouth and only some of it is stopped by the comforter.

"One more." I tell her. I can hear Annie's breathing again, she's slightly struggling with the pain but doing her absolute best to be good for me.

*CLAP*

The hardest of them all, of course.

"Mmmmm! My fucking god! Please fuck me. Please, Sir!" She screams, begging and writhing in front of me while still bent over as I demanded. I gently caress Annie's now bright red ass cheek as if to apologize just before I begin making things up to her for what she just endured.

The height of her bent over hips line up perfectly with the height of mine as I stand, which lines my cock up perfectly where it needs to be. I take my shaft in my right hand and guide it to her pussy. I gently slide it up and down in her lips to get the tip wet for entrance as Annie lets out a deep sigh.

I place my hands on their respective sides of her lean hips and slowly push every inch of myself into my newly-found sub's wet pussy. A sudden quiver comes over her body as her lips reach the base of my cock for the first time. As she requested, I slowly begin to pull every inch out to the tip and push myself back in again. Long stroke after long stroke, Annie's dream of being fucked good is slowly becoming her reality.

"Oh.. my fucking.. god.." she mumbles to the beat of my thrusts.

*clap*

I spank Annie's unpunished cheek as I continue fucking her. She moans loudly as it registers in her mind.

My mind issues a reminder: Hard. She likes it hard and rough.

My pace picks up. My strength picks up. My strong arms and upper body begin pulling Annie's hips and ass into my lap with more power every few thrusts. Her loud helpless moans and the subtle smacking of her ass against my skin makes a symphony of beautiful agony in this otherwise mundane room. My stamina holds and will hold for as long as I need to in order to make my sub lose all control.

After a long few minutes of me gradually fucking Annie harder and harder, I wipe the sweat from my forehead as I continue. I glance down and see her grool all over my cock as I stroke myself in and out of her soft pink lips.

"Sir... may I... cu-cum?" She asks loudly, with the rhythm of me fucking her heard in her voice.

"Yes, you may cum." I answer, not missing a beat.

Annie's hands extend even further out forward and grip the comforter. With her face straight down into the bedding, Annie begins cumming all over my hard cock as I fuck her over and over again. I can feel her hips quiver in my hands but I refuse to slow down. I have a job to do.

"Please Sir, don't stop! Please keep.. fucking me!" She screams into the bedding.

Focused on keeping my orgasm down, I don't respond. Instead, I push Annie's back downward as if to get her to arch it more. My right hand grabs a bunch of her curly hair and pushes her face hard into the mattress, my left hand grabs her hip to hold it in place as I begin fucking her with all I've got.

"Ohhhhh fuck, I'm going to cum again! Please Sir let me cum again!" She screams frantically, muffled by the bedding I'm forcefully pushing her into.

"Cum again, my good girl. NOW." I demand, getting extremely close myself with how turned on I am at her succession of orgasms.

I pull Annie's hair back hard towards me which lifts her head out of the comforter.

"OHHHH! FUCK!" She screams as she finishes yet again.

As the ending of her orgasm nears, I quickly pull my cock out of her as I begin reaching cumming myself. Annie lifts herself up off the bed and gets on her knees on the ground in front of me. She opens her mouth wide open, awaiting my load of hot cum like the good sub she was destined to be. She takes my cock in her hand and begins stroking me just outside of her mouth. I groan, looking down at her as she focuses on making me finish. My jaw clenches. My first shot comes, landing on her bottom lip. My second shot comes out more powerful as it forms one long line of cum from her upper lip trailing up near her eye. Before my remaining pulses have a chance to begin, Annie takes me in her mouth and pushes my cock to the back of her throat. Her mouth was drooling as she awaited this moment, and I can feel some of it dripping down to my balls.

"Oh FUCK." I groan, as I begin emptying every drop of cum I have in my body down her hot wet throat. Annie coughs due to her gag reflex and tears begin forming in her eyes, but she refuses to let me down and keeps me right there as I finish cumming. I open my eyes again and glance down to see her staring up at me. She sucks my tip softly as I finish, ensuring she drains me completely. I start to soften as she releases me from her lips, and Annie looks up at me. I reach a hand down to help her up and as she stands up she smiles.

"Well? How did I do?" I ask, out of genuine curiosity.

Annie looks at me with that adorable smile on her face.

"Absolutely incredible. The best orgasms I think I've ever had. I'm barely standing up right now, my legs are shaking so much. I really hope this isn't a one-time thing, Sir." She says with a grin, as if to say she likes the new name she gets to call me. Even with drool on her chin and the taste of my cum in her mouth, she holds strong with her confidence as she awaits my answer.

I can't help but smile back at her.

"Well, we still have one more night on this business trip. Perhaps if you begged me enough, I could find a way to make tomorrow even more interesting." I respond, with my own smirk forming on my face.