Not A Saint

I pulled my cock from her throat, leaving it sitting heavily on her tongue as she ran over it as the second load of cum shot inside her virgin mouth. I felt her body shudder, betraying the fact that the whip had made her cum. I saw her gulping, trying not to drown as her mouth was rapidly filling with my hot, salty cum. A third and forth shot filled it again, some leaking out the corner of her mouth as she tried to swallow all of my spunk. Her body shuddered again, the whip still running over her clit, a few times I hit it sharply. My last load shot out, my balls now emptied again, this time in her virgin mouth. I let my deflating cock sit limply in her mouth, letting her tongue taste my juices. I finally pulled out, my cum leaking onto her lips, cum dripping down from the corner of her mouth, my cock temporarily satisfied again. I still had her asshole again and the thought of that already sparked a new fire in my cock again.

"You suck cock good, Jessica, for someone that never did that before, you sucked it like a pro. And you came again, this time from the whip. What am I to think of you when every time you cum, even when I whip your pussy?"

Her head hung in shame, her mouth still filled with the taste of my cum. Let her get use to it, I had so much more for her.

I untied her legs and arms again, this time giving her time to stretch and rub them. I then got the rope again and I ordered her, "on your knees, facing the top of the bed and place your hands on the headboard." I grabbed her wrists and tied them securing to the headboard before she had a chance to contemplate her predicament. I saw her eyes open wide as she realized what I was going to do to her. "Yes, Jessica, it is time to take your asshole. My cock is big and it is going to hurt, but I think you will cum for me. You always do," laughing as I spoke.

"Please, Michael, not in my ass, it's perverted," tears running down her face as she begged me. Her eyes looked down to my cock, already hard in anticipation, knowing that she was not going to persuade me differently, sobbing as she realized her fate.

I went to the foot of the bed, admiring the view she presented. On all fours, legs spread slightly, her pussy pouch red and swollen from our previous fucking, her asshole peeking out from between her cheeks, a dark pink from my previous fingering of her private hole. I crawled on the bed, her head turning back to plead with me. I grabbed my cock in my fist, stroking it with long strokes, bringing it to its maximum size and girth, wanting Jessica to feel all of the mastery of my cock. I pushed down on her back, "arch your ass up for me Jessica, I want you open for me." I saw her reluctantly comply with my wishes, pleased that she was finally accepting the power I had over her body. I saw her hands clenching as my fingers touched her naked asscheeks, rubbing sensuously over them. "Your ass was made for sex, Jessica and I will be the first," my cock jerking in anticipation of being sheathed tightly within her ass passage.

Her head shook from side to side in rejection of my plans for her, her fists clenched tightly. "Ask me to fuck your asshole, Jessica?" I ordered her in a loud voice. She turned back at me, a defiant look in her eyes. My hand shot out, slapping hard on her right cheek, my handprint showing a bright red on the alabaster flesh. She gave out a yelp, which I followed up with another quick slap to her other cheek. The slap of my hand hitting her naked flesh made my cock harder then I had ever felt it before. It took two more sharp slaps to her ass cheeks, both of them bright red in response to the punishing blows before I heard her whimper.

"Put your cock in my backside, Michael," she whispered quietly.

Another sharp slap and her voice boomed up, "fuck my asshole, please."

My fingers spread her ass cheeks out, her asshole exposed to my gaze. My fingers pulled on either side of the tiny opening, watching as it opened, slowing revealing the dark depths inside her. I heard her moan in pain as her asshole began to open, forced by my fingers. I took the bottle of baby oil and slowly poured it over her ass, allowing it to run freely all over. It would be such a good feeling to squirm all over her slippery ass all the while my cock was deeply embedded in her hot and tight asshole. My finger returned to the tiny dot and I felt her hesitation as it slowly began to twist and turn, seeking entry in her back passage, aided by the slippery baby oil. Her sphincter could do very little to stop my fingering and the tip of my finger quickly slid inside her asshole. I heard another whimper coming from her lips, feeling her sphincter clenching and unclenching on my digit as I twisted it around the tiny opening. I inhaled in the scent of her asshole, a slight repugnant smell offset by the smell of her sex already juicing up in response to the inevitable taking of her asshole.

"So tight and hot, Jessica, you don't know how much your body pleases me," my finger pressing deeper and deeper, rotating as I plunged into the depths of her asshole. "Yes, Jessica, let your asshole fight me," feeling her body trying to expel the intruder that ruthlessly plunged up her backside. It was not used to having something push in, only out. No matter how much Jessica tried to overcome her body's defenses, she could not stop them from trying to force out the invader.

"No, no," her head shaking as she cried out from the degradation of the act I was inflicting on her body. Her asshole continued to push out, clamping onto my finger as it tried to push it out like it was designed to do.

My finger was now buried deep inside her asshole, my knuckle bumping against her anus, rubbing harshly over the sensitive mouth of her asshole. I felt her squirming beneath me, my finger twisting and turning deep inside, wanting her to feel the complete control I had over her body. I took a second finger, it smashing against the mouth of her asshole before it began to press in along side of the other, her anus now stretching wider to accept the two thick fingers forcing their way into her asshole.

"Please, no more, it hurts," her tear filled eyes pleading with me as I watched her asshole stretching open wider, her sphincter clutching tightly on my fingers as they gripped it like a giant rubber band stretched to its limit, ready to snap from the strain.

"Yes, Jessica, you are so tight, but you can take my fingers. There is so much more. My cock awaits the opportunity to feel the grip of your asshole as it fucks you. So much more stretching you will have to suffer to please me, Jessica, so much more," laughing as I finger fucked her asshole. I buried the second finger along side the first as she heaved and bucked beneath me, two inches wide of thick finger punishing her asshole, shoving aside the silky insides as she fought me every inch of the way. Finally I had both fingers buried deep inside her, the mouth of her asshole stretched wide, the pink color now turning white as it was forced to accommodate the thickness of my digits. I twisted them inside her, spread them open while deep inside her, all to hear her moan in pain. My cock was throbbing in expectation, the sound of her voice as my fingers violated her exciting it beyond anything that I had ever experienced before.

"Hurts too much," she cried out in pain as my fingertips spread deep inside of her, opening her insides as they moved around deep in her, forcing her clenching asshole to accommodate their thickness. "No more," she begged, her pleas falling on deaf ears, my cock now controlling my body, not caring about anything except the desire to fuck poor Jessica's pulsating asshole. I felt her body slump down as I pulled my fingers out of her asshole with a loud pop, her anguish and embarrassment overcoming her senses. Her relief was short-lived, my cock returned to where my fingers had been, ready to replace them. She shivered in fear as the hot head of my cock pushed against the slightly swollen asshole, still opened from the fingering.

I poured more baby oil on her ass, making sure it covered my steel-hard cock pushed against the tiny asshole. Although she had been speared by two of my thick fingers, it was nothing compared to the size of the crown of my cock. It had to be at least three inches wide, swollen to its present state by the excitement her asshole would bring to it. I pushed my hands down to the side of her hips, grabbing her tightly, ready to control the movements of her hips, ready to show her how to fuck my cock. I slowly crawled up her back with my body, wanting to be able to fuck her as deep as possible, wanting to her feel the mastery of my cock in her asshole.

"No, don't, please don't," her last attempt at persuading me causing my cock to twitch in anticipation. "GGGGGGRRRHHHH," she cried as I began to push down on my hips while my hands held her hips up, never letting her escape the cock that was slowly forcing itself into her back passage. "AAAAAHHH, God, take it out, don't," feeling my cock slowly stretching back the skin of her asshole, forcing it to almost tear as my head, now hard as a rock began to push inside. I could feel my piss slot sucked into the hot confines of her asshole, her sphincter clenching onto it. Another shove and half of the head was now inside, her sphincter trying to push it out, my cock twitching into even greater hardness as it slowly penetrated her asshole, aided by the liberal amount of baby oil.

I could not hold out any longer, my hips shooting out sharply, forcing the head of my cock to push inside her pulsating asshole, her sphincter grabbing it just under the ring, squeezing it like a pair of child's hands jerking me off. Her scream in pain thrilled my cock, as she bucked underneath me, my strong hands the only thing that kept her from pushing me off. She was like a bronco, intent on throwing me off, my grip on her hips allowing me to tame the beast within her. "Relax, Jessica, it's in, time to take daddy for a ride," feeling her body reacting to the intruder in her, her insides clenching on it, pushing out to expel it.

"Don't move," she begged. The pain of withdrawal the same as entry, willing to allow its presence to prevent any further pain.

I began to move her hips slowly from side to side, her asshole forced to massage my cock head as it moved around inside her clutching asshole. "Relax, Jessica, " I whispered into her ear, "get used to my cock inside your asshole." I was in heaven, this lovely little girl, naked and spread before me, my cock grabbed tightly by her asshole as she fucked me so lovingly. She was mine to do as I pleased and I wanted to fuck her. "I want you to take my cock deep inside you, Jessica. Please me with your asshole." I pushed down on her body, feeling my cockhead begin to slowly sink further into her body. I jerked forward, then pulled back, then forward again. Each time I was forcing her asshole to take more of my cock. I entered her rectum with my cock, the hot confines sucking me deeper into her body. Her clenching asshole forced me to use greater force each time. I began to rabbit fuck her, using short, hard thrusts into her asshole each time. I would enter her a 1/2 inch deeper every time, pull out and then plunge in again, each time reaching new uncharted territory, places where no other cock had ever plundered.

Jessica was screaming in pain as I fucked her. It was music to my ears. Each scream of pain brought about another rabbit fuck into her asshole, my cock tearing into her body, plundering her virgin asshole. She might have fucked Reilly, but her asshole was only mine. And I wanted her to remember this night forever. The night that my cock took her asshole for the first time. My hands held her hips tightly, forcing them right to left, massaging my cock as I pumped my cock deeper into her asshole. I had over half of it in her now, her asshole looking like it would tear and bleed if it stretched any longer. I did not care, my cock was intent on fucking her as deep as possible. I no longer controlled my body.

"OOOOWWWW, t-take it out, to bigggg," she screamed in pain, her hands grabbing the headboard tightly, her face clenched in pain as I tore into her asshole with my steely dick.

"More, Jessica, you have to take more," rabbit fucking over 3/4 of it inside her, over six inches of hard cock being massaged by her clenching asshole. I jerked forward again, this time wanting to bury all of my cock in her asshole. I shoved hard down on my hips, pulling up on her hips as all eight inches of my cock slowly slid along the slippery baby oil and plunged deep into her colon. I felt her body jerking in pain, as her colon was forced to straighten out to accept my cock.

Her scream rang in the room. Good thing the building was empty, I'm sure it would have been heard on the sixteenth floor. It must have felt like a steel bar was being forced up her ass as my cock achieved its goal of being tightly sheathed in her asshole. I stayed still, my cock jerking around inside her as it was massaged by her clenching asshole. I did not know how long I could remain motionless, my desire to fill her colon with my hot cum superseding all others. My hand reached over and pulled the wet hair from her face, her tears running down her face in a continuous stream now. "You have all of my cock now, Jessica, how does it feel?" making my cock jerk inside of her, wanting her to feel how I now controlled her. Again I jerked my cock, feeling her jump in pain as I did.

"Take it out, finish with me quickly, it hurt so much, OOOWW," she cried, my throbbing cock inside her jolting her body in pain.

"Soon, but first you will have to make me cum, take my cum deep in your asshole." She moaned in pain as I bent over her body, one hand reaching under to grab her crotch with my big hand, my fingers slipping deeply between her slippery slit. "It may hurt to have my big cock in your asshole, but your pussy is wet with desire." My other hand reached one of her dangling tits and began to pinch the nipple hard, twisting and turning the hard nub, feeling her body squirming beneath me. I began to abuse her body with my hands, tearing at her pussy and nipple with my fingers. I gripped her clit between two fingers, twisting and turning it in rhythm with the one on her nipple. She arched her body up, forcing my cock in deeper into her asshole, the pain forcing her to pull back down, allowing my cock to slip sensuously from her asshole as it clutched it. She began to fuck my cock, the pain of my fingers forcing her actions, my cock forcing the reaction.

"Cum in me, hurry," her hips becoming a blur as she fucked me harder and harder. I know she must have been in extreme pain, her face contorted, sobbing loudly, but her asshole continued to fuck my cock in and out. It pulled back until only her sphincter trapped the head, then she fucked her hips back, forcing her asshole to suck my cock back into the depths that could only being painful.

My cock had never felt anything as tight and hot as her asshole. While her pussy was good, it could not compare. Knowing that she was submitting to my cock, knowing the pain I was inflicting on her, yet she continued to fuck me, trying to make me cum. Her love for me was real, her love for my cock. My fingers on her clit became more tender, rubbing over the swollen nub, feeling her surrendering to me, her hips now rotating onto my cock up her backside. "Tighten your asshole on my cock as it pulls out from your body, make me cum, Jessica. I will reward you with my hot cum." I slapped her ass cheek, feeling her asshole clench in pain on my cock. "Like that, do that again, Jessica," my hand slapping her again.

"Ok, just don't slap me again," grabbing my cock with her asshole as I dragged it from her body.

It was hard to pull from her body, her asshole so tight, grabbing at my cock as I pulled out. When only her sphincter trapped the crown of my cock would she relax her asshole, allowing my cock to plunge all eight inches of hard cock into her in one forceful stroke that knocked the wind from her lungs. I could not last much longer, I needed to blow my wad in her asshole. The first of many times I would. My fingers continued their ministration of her clit, feeling her body betraying herself. I was going to force her to cum. Cum when she was being fucked up her ass. "Can you cum for me, Jessica? I am going to fuck you until you cum first. I can go all day, can you?"

"Yes, make me cum, make the pain stop, pllllleeease," she shouted in pain, her clit pushing deeper into my fingers, hoping to make herself cum.

I felt her body shudder, recognizing the signs that my love made when she came. Gurgling sounds came from her mouth, unrecognizable noises from the combination of pain and pleasure that she was enduring. Her body clenched onto my cock, her orgasm rippling through her asshole, massaging my cock. "Take my cum, take it deep inside you," pushing my cock deep inside her, feeling her body jerk in pain as it tore up her asshole. I began to shoot inside her, the hot salty sperm coating her abused asshole.

"GGGGODDD, h-hurts, ccccuuummming," her body confused, unable to contain all of the conflicting emotions within her. It felt like gasoline was poured into her asshole, the salty cum reacting harshly to the abraded tissue in her asshole from the pounding his cock had inflicted on her virgin asshole. Repeatedly he poured her full of his cum. Her stomach gurgled as her asshole began to fill with the copious amount of sperm, a literal sperm enema being inflicted on her body. Her pussy dripped her cum all over his hand as he continued to masturbate her to multiple orgasms.

Finally we both slumped over into sexual exhaustion. The multiple orgasms, the bondage and the pain were too much. Jessica slipped in and out of consciousness, the heavy weight of me still on her back. Our heavy breathing filled the room, the smell of sex permeating throughout.

My cock began to soften within the confines of her asshole. I had been fucking her for a long time, the need to piss becoming strong. I was ready to pull out of her when a thought came to him. I always had a desire to give a woman a piss enema. My cock began to harden with the thought of it. I would have to hurry if he were going to succeed. "Stay still, don't fight my cock with your asshole. Just take what I am going to give you."

Jessica's head popped up, the confusion on her face showing. She felt the cock inside her straining, not able to comprehend the results. Suddenly she felt a hot liquid filling her colon, knowing that he could not be cumming again. It dawned on her, he was pissing up her asshole. I was giving her a piss enema. "No," she shouted back in anger, "No, NO, NNOOO" as I continued. The hot piss burned her back passage, the pain igniting the abraded flesh. She felt her stomach begin to swell, the large amount of piss filling her. Her stomach began to cramp, the piss mixing with the sperm I had deposited in her. She began to cry loudly, her degradation complete. She hung limply as I used her as my personal toilet.

I pulled my cock out leaving my piss inside my lovely girl. I let her body fall on the bed as she had all my cum and piss up her asshole. It was so fuckin' hot. I started to get dressed feeling totally spent. It'd been the best fuck I'd ever had. I wasn't going to let go of Jessica so easily. She was going to become my own little fuck slave whether she liked it or not.

I moved over to her pulling her hair and her head tilted back. Her eyes were red and puffy from crying and screaming so much. "Now Jessica did you like that?"

Her eyes searched mine. Those pretty brown eyes didn't have the same glow or innocence they used to have. "Y-yes master. I loved it all." She responded quickly.

I took Jessica with me that night. I wrapped little body in a big towel and carried her to my car. I got the keys to her car and drove us to my house. We drove in silence as her hands were tied with a rope as she sat in the back seat.