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A Filthy Raffle

By Mark Cannon Jr.

By Mark Cannon Jr.Published 3 years ago 14 min read
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A Filthy Raffle

I had won Kerry Louise’s raffle that saw me get the opportunity to engage in a night of filth with the sexiest woman on Earth, Kerry Louise. I had fantasized about her so many times, my mind racing with things I’d do to her if ever given the opportunity. Now that the moment was here, I was overwhelmed with desires and already had a raging hard-on in my white slacks. I wanted to look my best for the British beauty, so I wore a white suit, red dress shirt with a white and red striped tie and black loafers. Kerry had really gone all out as I was picked up at my house by a long white stretch limousine and driven to the hotel where she was staying. As we inched closer to the hotel, I felt my dick growing, even more, it was now very noticeable. The driver pulled up to the hotel and let me out.

I took a deep breath, trying to remain calm despite the fact I was about to fulfill my greatest sexual fantasy. I walked in and got in the elevator, a usual minute ride felt like a lifetime, my heart began beating faster the closer I got to her door, I knocked and eagerly awaited her answer. It took a few moments, it might as well have been a lifetime, but she answered. There she stood, the sexiest woman I had ever seen standing before me, her long black hair, beautiful blue eyes, perfect lips, huge breasts, her slim waist, long legs, cute feet, and her perfect tan. I stood there, unable to speak, completely mesmerized by her beauty. “Hi, There!” She said, her sexy British voice sending a jolt of excitement…and life back into me. “Hi, Kerry! Such an honor to meet you!” I said captivated by her incredible body.

I stared at her up and down and couldn’t believe she was actually sexier in person. This woman had been driving me wild since the first time I saw her in a scene, she was a psychic detective and after brief dialogue, she gave one of the filthiest performances I’d ever seen. I watched her as she had incredibly rough sex with her co-star and I lost myself as I jerked off, imagining myself banging her like that. “So, are you as nasty in real life as you are in your scenes?” I blurted out, immediately horrified that I had blown any shot at getting the Kerry Louise experience. To my surprise, she smiled widely and began playing with my tie. “I am! You want a firsthand experience?” She asked, now grabbing me by my tie. “Yes!” Was all I could get out, as I felt my body heat up, a hot rush flowing through me. She told me to follow her as if I had a choice? She had me by my tie. She brought me to the bedroom, and I stared at her perfect ass the entire walk.

She pushes me against the wall of the room and grabs my crotch. “Mmm, you are a BIG fan mate!” She says with a grin as she rubbed the entire length of my shaft. “Oh, Kerry, you have no idea how many times I have jerked off to you!” I moaned. She dropped to her knees and easily removed my pants and black boxers, letting my aching dick free. “Hmm, my turn to jerk this cock now!” She says, her hand wrapping around it and slowly stroking the entire length of it. I rested my head against the wall and watched as the stunning, Kerry Louise began jerking my cock. “That’s it! Stroke that dick baby!” I groan as pleasure jolted through my body it was so hard not to explode right there, somehow I managed to keep myself under control as I did not want to disappoint my ultimate fantasy.

Kerry expertly worked my cock, her hand gliding with ease up and down my dick. She made sure to make eye contact the entire time, I knew, that she knew, she was driving me wild. “Want me to suck your dick?” She asked with a grin. “Oh yeah!” I moaned, in awe of what I had just heard. I felt the warmth of her mouth engulf my cock, followed by the wetness of her lips as they slid up and down the length of my prick. She wasted no time either, she was sucking me hard! Making those awesome sucking sounds I had heard so many times in her scenes but now not only was I watching her suck a dick, but I was also watching and feeling her sucking my dick! “That’s it, suck my cock!” I grunted. “I want you to gag me with it!” She instructed. I grabbed her by the back of her head and shoved my cock down her throat until I felt the tip hit her tonsils. I grabbed the base of my dick with my free hand and shook my cock, adding to the gag factor.

I slowly slid my cock out of her mouth and watched as her saliva dripped off onto the floor. She looked up at me, her eyes watery and a huge smile on her face. I shoved my cock back down her throat, this time holding her down on it a little longer as, her, gagged moans filled the room. I began thrusting my dick in and out of her mouth, shoving it all in every three thrusts to gag her some more. Her spit was now covering my balls and dripping all over the floor! So far, this was better than anything I’d ever imagined. “Thoo!” She again spits on my cock and rubbed it in, making it glisten with precum and saliva. “You want to eat this pornstar pussy mate?” She asked as she got to her feet and sat on the bed, rubbing her panty clad crotch. I made my way over to her, sliding my hand down into her wet panties and kissing her, tasting my dick on her tongue.

I yanked off her orange panties, exposing her perfectly shaved twat, and admired just how perfect it indeed was. “That pussy is so perfect, Kerry! But none of those boys eat it right!” I said, now feeling a bit full of myself. “Oh yeah? You think you have what it takes to eat this pussy as it deserves?” She asked while smacking and rubbing it. I knelt down between her legs and slowly licked the length of her perfectly tanned thighs; I then turned my attention to her sweet pussy, taking a long, slow lick of her slit. She tasted better than I’d ever imagined, and I wanted more of her! I spread the folds of her twat apart, exposing her clit, I flicked my tongue on it rapidly and she moaned her approval. I looked up at her as she watched me work her over and I could tell she was enjoying it. I began sucking on her clit while sliding a finger inside of her, she was so warm and wet! “Oh yes! Just like that baby!” She moaned as I sucked and fingered her cunt.

I swirled my tongue up, down and all-around her salty clit, she was so tasty, I could eat her out forever! “Stick a finger in my bum!” She demanded. I did as I was told, sliding a finger in her butt while slipping two more in her pussy. I sucked on her clit some more as my fingers began working in rhythm, stimulating her tight, perfect holes. She was moaning so loud, it made me want her even more! Staying focused, I continued pleasuring her until I just had to have her. “You ready to be fucked, babe?” I asked, my dick aching for Kerry Louise. “Give it to me hard!” She demanded. I drove my rock-hard cock all the way inside her wet pussy and gave her several hard thrusts right away. My cock stretched her tight pussy wider with each thrust inside, and she encouraged me the entire time.

I squeezed her huge breasts as I thrust deep inside of her, giving her a good, stiff pounding. I slid my hand between her tits and gripped her throat, choking her. “Ugh! Oh! That what you like, Kerry?” I asked, my cock going balls deep in her pussy. “Fuck me fanboy!” She demanded. I gave her several hard thrusts, watching her smile with ecstasy as she felt my dick plow her twat. I leaned down so I was on top of her, continuing to slam my cock deep inside of her, keeping my hand on her throat as I swirled my tongue in her mouth. “Ugh, Oh, yes!” I grunted as gave her a hard pounding. She reached up, grabbing my throat after shoving her fingers in my mouth, making me suck on them. It was all I could do to keep from Cumming right there, I closed my eyes and slowed down my thrusts, regaining my composure.

I released my grip on her throat and gave her perfect tits a hard squeeze while thrusting her a few more times for good measure. “Let’s really test this bed out! I want you to ride my cock!” I said, pulling my wet dick from her dripping pussy. As I laid on the bed, Kerry spat on my cock again before lowering her amazing body down onto me. I felt my prick penetrate her again and she wasted no time, riding me roughly. She leaned down so her tits were in my face, so I sucked her nipples and reached around, grabbing her incredible butt. Kerry slammed her body onto mine and I slammed up into hers, our bodies meeting and smacking together passionately. We were both beginning to sweat as we were giving each other our all. I began spanking her bum while she rode my cock, giving her what she deserved.

My moans were muffled by her big breasts that dangled in my face and I felt the flesh of her butt jiggle each time she crashed down onto me. Kerry felt more amazing than I’d ever imagined she would’ her pussy, tight and wet, her butt fleshy and toned, her black hair bounced happily as she pounded her body onto my prick. The aroma of sweat and sex filled the room as we breathed heavily as we slammed into one another. I continued spanking her, turning her buns a nice reddish color and she groaned loudly with each smack. “You’re such a bad girl, Kerry!” I moaned with a smile. “No, I’m the baddest girl!” she corrected me. I was in no position to argue, so I just continued thrusting my dick into her. “Fuck me!” She ordered, slapping my face lightly. “I said, fuck me!” She says again, this time smacking me harder. I thrust harder into her, but she wasn’t impressed. “FUCK ME!” She screamed, this time slapping my face hard enough to leave a handprint on my cheek. I grabbed a handful of her butt cheeks and pounded my dick into her as hard as I could. Kerry licked her lips and screamed my name; I took this as a sign I was doing what she wanted.

Kerry’s hands roamed my sweaty body as she grated her nails down my chest, scratching me lightly. “Take me, doggy baby!” She instructed before getting off me. As she got onto all fours, I took a moment to admire the view before slapping her ass then inserting my throbbing pole into her again. I grabbed her by her damp black hair, slamming my dick into her roughly. “Yes! Like that you, lucky boy!” Kerry moaned as she thrust her body back against my pelvis. I pulled her hair hard enough, so she arched upwards and I turned her face so she facing me. “You feel so good, Kerry!” I grunted as my cock continued assaulting her pussy. I reached down to feel her tits again as we both moaned loudly, our warm breath brushing against each other’s faces. “Oh, Kerry!” I kept moaning, as I drove my dick deep inside of her twat.

Kerry leaned down and told me to stick a thumb in her butt, so I did. I began fingering her rump as I thrust deep in her pussy. “You feel so good, baby!” I panted, my breathing becoming rapid as I was giving Kerry every ounce of energy I had. “Fuck me!” She ordered, so I pounded her rapidly, sweat flying off of our bodies. As I watched her butthole pucker from me stimulating it, I became fixated on it, wanting to feel my prick stretch out her super tight hole. “Oh, I’m going to cum!” Kerry groaned. I focused on pleasuring her pussy, and soon I felt her pussy tighten and her juices flooded down my rod. I kept focused, not wanting to cum just yet, I needed to take, Kerry in her bum. “Can I stick it in your ass babe?” I asked, not wanting to give her something she didn’t want. “Okay, but you have to cum in it and suck it out!” She said, looking back at me with the naughtiest smirk I’d ever seen. “You, filthy girl!” I said smiling at her. Kerry rolled her tongue across her lips and smiled.

I pulled my cock out of her pussy and watched as her wet hole contracted back to normal size. I spit in her ass, lubing it so my cock could enter. I pushed the wet head of my dick in her tight hole slowly, but she wasn’t having that! “I want it, hard mate!” She instructs. So, again, I held her tightly and began thrusting hard inside her asshole, stretching it out. “Oh yeah, fuck my tight ass!” She demanded. I held her hips while my dick drove into her hole, stretching it further each time. I move my hands to her cheeks, spreading them and spatting down on my dick, providing more lubrication to slide into her bum.

I watched happily as my cock inched its way inside Kerry’s beautiful ass, pushing deeper and deeper into her tight hole. My balls smacked her cunt as I was slamming my rod into her. “You’re so tight!” I grunt, feeling her butt choke my cock. “Yeah, stretch me, babe!” She moaned, I push her down onto the bed, holding her head down as I slammed into her. “Yeahhhh, fuck meeeeee!” Kerry screamed. I pounded her like this for a minute before pulling her back up, so our bodies were together. “Ugh! This my ass now!” I whisper in her ear. “Okay, daddy! Fuck it good!” She moaned. I plowed my cock in her, harder as she screamed in my face. This was all I could take. “I’m going to cum!” I grunted. Kerry leaned down and I gave her the hardest thrusts possible as I felt my cock beginning to pulsate. “Ugh, fuck, Kerry Louise!” I shouted as a massive load ejected from my cock. I gave her a few sudden thrusts until my dick went totally limp. “Go on now mate, eat my asshole!” Kerry panted. I knelt down behind her and looked at my, cum dripping from her tight hole. “You want to taste it, babe?” I asked. “Yes, suck it out of my ass and spit it in my mouth!”

I stuck my tongue deep in her hole, tasting both her ass and my, cum, I swirled my tongue around for a minute before sucking my load from her asshole, I went over to her as she knelt up and opened her mouth. “Give me that filthy fucking load!” She ordered. I leaned my head down and spat my, cum into her mouth and took it and loved it. “Mmmm, Mmmm” she moaned while swishing my load in her mouth, she opened her mouth, showing off she still had it, she then gulped it down and opened her mouth again showing me it was all gone. “You are the filthiest, Kerry!” I said in awe of the filth I had just witnessed and experienced. “Was there ever a doubt mate?” She asked proudly. “We should do this again some time babe!” She said as I got dressed. “Any time you want it, Kerry, I’ll be your fuck toy!” I said happily.

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