Day 4
Oh man I love anal, how have I been missing out on this for so long.
Chunk, the lights flicker on, startling the slight woman from her slumber. She looks around with bleary eyes, searching for anything to signify that she was no longer in captivity. Her eyes finally came to rest on me; her head sagged as she determined nothing was any better for her. I stared at her toned body as she sighed and stood up. Her breasts rose and fell with each breath and I stood there staring for a good five minutes.
Finally realizing I was drooling, I began to walk towards her. She lowered her chin to her chest as I approached and avoided my gaze like the plague. I stepped in front of her and grabbed her small chin firmly between my fingers and lifted her head until her eyes could no longer avoid mine.
“I’m going to fuck you today” I whispered to her face.
“Yes Sir” she mumbled.
“What was that?’ I asked, raising my voice so it echoed throughout the room.
“Yes Sir!” she exclaimed, her voice slightly raspy from all her crying.
“Much better” I said, moving around behind her and placing my hand on her neck.
Her skin is so soft despite everything, my fingers brushed lightly against her neck as I gently guided her to a low table. She knew what to do and kneeled on the hard wood surface as I clamped her ankles onto the edge. The table is about knee height for me so her ass is about waist level when she’s shackled to it. I cuffed her wrists next to her feet so her face was pressed against the wood and her round ass was pointing towards the sky she would not be seeing anytime soon.
My fingers went straight to her pretty, pink pussy. They danced around her clit, dragged between her pussy lips and traced a circle around her tight ass hole. She gasped as my fingers teased her ass, lingering a little too long. With one smooth motion, I pushed my finger into her small asshole and she made a noise similar to that made by a dog when you step on their tail.
I wiggled my finger around a bit as I worked it deeper into her tight ass and she groaned in a mixture of pain and pleasure like nothing she had felt before. My finger made its way deeper into her pink asshole and my other hand began to stroke her firm ass cheeks.
Smack, I spanked her ass, leaving a bright pink hand mark. She yelped and lurched forward, my finger still lodged in her warm ass. She made a sort of groaning noise mixed with a noise like she was choking. I smacked her again for the erratic behavior and this time she stayed in place.
I pulled my finger of her tight asshole and unzipped my pants. I pulled out my already rock hard cock and began to stroke it, moving my other hand up and down along her pussy and over her winking asshole. I was so impossibly horny now; this was to be the first time I ever fucked a woman in the ass and my balls were aching beyond belief. My finger went back into her ass really quick and then pulled out and went into her dripping pussy.
“Ooh, someone’s excited!” I said as I slipped another finger into her tight cunt and began rub the head of my cock down her ass. I pulled my fingers out and pressed my throbbing cock against her little, pink asshole. She squirmed against the pressure on her tight asshole as I started sliding my cock inside her. She gasped as my cock slid in, all the way to the base, and gave her a surge of pleasure she had no idea was possible. I began to slowly move my hips away from her ass, pulling my rigid cock back out of her ass. As my cock pulled passed around half way out, I slammed it back home, eliciting a squeak of pleasure and shock. I pulled out again, this time coming back until just the head of my cock was still inside her. The feeling of her tight, warm ass around my cock was intense and I had to struggle not to cum right then and there. I slowly slid my cock back into her and fucked her like this until I was gasping for air against the need to shoot my hot cum deep into her ass.
I pushed my cock all the way in again and stayed there like that for second, letting myself settle down a bit. No longer fighting orgasm with every fiber of my being, I pulled out slowly. I pulled all the way out this time, her ass squeezing my trembling cock as it slid smoothly out. As the tip of my cock pulled out, I came very close to cumming as her pink asshole returned to its tight and unforgiving state. I took a deep breath and thrust my cock back into her, hard. It took some effort to force it in fast but I pushed with my weight and jammed my hard cock into her ass balls deep.
I grabbed her hips and slammed my cock in and out of her warm ass. In seconds I was cumming deep into her virgin asshole. She squealed like a stuck pig as the hot cum went up her ass, deeper than anything should go. I thrust one last time and left my cock in her ass as deep as it could go. I moaned loudly as the immense pleasure surge rushed through my body and filled me with wonderful warmth. This orgasm was better than any I’ve had recently; on par with the first time I had sex.
I pulled my sensitive cock out and wiped the tip off on her firm, pink ass cheeks. I walked around to her face and squatted so we were level.
“You are going to keep my cum in your ass all night tonight, doesn’t that make you happy?” I whispered to her face.
“Yes sir” She grumbled, still recovering from her first experience with anal sex.
“If I find that any has come out tomorrow when I get back…you’re going to be in some serious trouble. Painful trouble” I said forcefully, my words slamming into her face, forcing her to cringe and scrunch her forehead.