Anything For A Fiver (Celebrity Story)


I have an interesting story to tell. A strange story, but interesting nonetheless. I’m friends with Katy Perry, hard to believe, but the truth. Most people find it more difficult to imagine that she even has friends, even less so that she would have friends like me. I was a childhood friend first, before the grandiose of fame came about and took her to higher places, whilst I remained below. But friends nonetheless. She and I have always been close and the boundless riches that she gained have resulted in no real change in our relationship other than in making one of our games have higher stakes. See, she and I have a constant running bet. Every now and again, we’ll challenge each other to do something. Started with us betting each other a fiver to do something ludicrous; flash ourselves in a crowded bar, steal something, and the such. Nothing big, but bold nonetheless. Whilst she offered to bet more money as she got richer, I refused, and it became more a playful thing than anything. We weren’t playing for money, rather attempting to make the other person embarrass themselves. Truth be told, the true reward was in the fact that I had the power to place her properly under pressure; orchestrate a nip-slip, say something obscene on camera, make a shitty music video (not that I had to prompt her to do that). Which leads us to the latest challenge… My challenge…            
            She was rather ceremonious about it all. She texted me, invited me over, saying that she wanted to tell me my challenge, which was rather odd. Usually, we tell each other whenever we see each other. We don’t make a point about it, so I was already on edge. Still, I went to hers. I wasn’t about to sacrifice my chance to keep this game going. Katy met me at the door, a silk bathrobe clasped around her body, hugging her curves. I may have been her friend, but I wasn’t an idiot. She had a gorgeous body, one that I had the joy of seeing more of than most people. I lusted after her. There have been several drunken nights where I hoped she’d throw caution to the wind, drop her panties and let me have a go at her. Lord knows I’ve stared at that fat juicy arse of her plenty of times, fantasised about spreading those legs of hers and spearing her on my cock. I’ve heard on the grapevine she’s rather good with her mouth. Little did I know I was about to get a crash-course in sex with Katy Perry. Not how I imagined it, yet… Can’t say I’m disappointed.
            I made my way to the living room, sinking into one of the sofas as she… prepared. I didn’t understand what she meant until she rounded the corner, drawing my attention as she dropped the silk robe she was wearing and revealed the true nature of my challenge. She was ostensibly naked. The bits of her that mattered. Her bountiful breasts were exposed, hanging unnaturally perfectly on her body, though I knew they were entirely real. They defied gravity and were capped with the most perfectly pert nipples. She had some lacy garments covering the rest of her body, with stockings covering her deliciously supple legs; long and unbelievably slender. However, that was not what drew my gaze. No. Nor was it what was supposed to. Her breasts were gorgeous, but it was what lay between her legs that was my ‘challenge’. Instead of an exposed, delicious quim, there was slung instead a thick and heavy strapon, thicker and heavier than any I had seen before (online that is). It was easily fifteen inches, maybe even eighteen, and about as thick as my wrist. It was made of black plastic, formed and shaped into a veiny cock; horse-cock. Of course, it was a horse-cock. There were no half measures when it came to these challenges. The smile on her face was devilish. A smirk that spoke no words but told me enough as to what she wanted.            “I bet you a fiver, you can’t take my strapon up your arse,” Katy smiled, wrapping her hand around the base of the shaft and gently shaking it back and forth. Even with such a strong grasp, she wasn’t able to hoist it upright, the weight being so immense, “What say you?”            What could I say? Well, I didn’t say anything. Rather, I slowly began to unbutton my shirt, slowly unfastening it. The smile on Katy’s face stretched a little wider as she walked to the window and pulled shut the curtains. Stripping down, I dropped my jeans and boxers to the ground, standing naked in front of her. Her eyes drifted down to my crotch, my cock standing hard and proud. Not that it was going to be used. Though, I do say rather proudly, she gave pause as she saw it, twitching in reaction to the promise of some form of pleasure. I dare say I saw surprise in her eyes; almost as if she had misjudged me in that regard. Offering me her hand, Katy led me towards the bedroom, walking me to the lavish plush bed that she had so lovingly prepared, beside which sat a large and copious bottle of lube. At least she had that courtesy in her. Leading me towards the bed, she gave her orders, commanding me like a puppet. Or sex-doll. No, not sex-doll. Somewhat emasculating if entirely and utterly true. I must remember to take that out…            Laying on the bed, I rolled onto my hands and knees, presenting my ass to Katy. I expected her to take the lube and begin work, yet I was instead offered a rather delectable alternative. I don’t know what sway Katy, yet I could tell this was no longer a challenge. She sidled onto the bed behind me, her hands pressing into my ass cheeks, spreading them wide to revealing my puckered, untouched asshole, completely at her mercy and entirely for her to play with and devour as she saw fit. And boy did she devour it. I didn’t see it, but rather felt it. Her lips leant forwards and pressed against my asshole, gently and tenderly kissing my entrance, her tongue briefly flicking against my entrance, sharply and suddenly enough to elicit a moan from my lips and a wayward glance over my shoulder; a glance that was met with the luscious, lustful stare of Katy Perry, her eyes framed above the curve of my ass as she moved to lap and lick at my asshole. Moaning, I relaxed myself, letting her tongue trace back and forth, darting up and down, across my ass, layering and lathering saliva on my rosebud. She let my cheeks fall back into place, her hands dropping down to my cock. I had assumed it would go untouched, yet she lovingly and tenderly grasped my cock, gently stroking it back and forth, massaging and squeezing it, milking me as she licked my asshole. Her other hand grasped my balls, massaging and squeezing them, adding to the pile of pleasure, building more and more of an intense orgasm. Swiftly, everything began to spiral out from the original purpose. Sure, I was going to get fucked hard, but not before I had my ass eaten out by Katy Perry.            Her tongue curled inwards, finding my entrance, gently sliding back and forth. Slowly hooking inside the dip of my asshole, she went about trying to loosen me up; allow her tongue deeper. Little by little, the pleasure of her tongue relaxed my muscles, prepping me. Eventually, she made her tongue rigid and pressed it against my hole and began to apply pressure. Slow and steady. I was comforted by the patience she moved with. My ass gave away with ease, her tongue sinking deeper and deeper inside me, wriggling back and forth, exploring my depths with a certain eagerness. The moans that came from my lips were unlike any I’ve ever made. They were deep and powered by pleasure. As intense and as deep as any I’ve ever made. That spoke to the pleasure. I couldn’t begin to describe the way my ass reacted, spreading and loosening, her tongue curling and inching throughout my hole, dousing me in saliva. Pulling her tongue back, her hands abandoned by cock, spreading my cheeks once more, spreading my asshole, gaping me. A dribble of saliva ran down across my ass, a dribble that was quickly massaged into place by Katy’s finger, smearing the substance liberally, rendering my ass a gleaming glow. Breathing steadily, I felt pleasure once more… an intrusion. And the first promise of what was to come; pleasure and all.            A single finger, pressed against my loosened hole. Easing it slowly forwards, she let it sink inside of me, curling upwards to find my sweet spot. Running it across my prostate, I began to shudder, twitch and moan. My cock throbbed as she drove it back and forth, my body thrumming with the pleasure of it all. Moans escaped my lips as she bounced the finger back and forth, finger-fucking my arsehole. The first few pushes were slow and tentative, yet as I gave away, the slickness of her previous oral ministrations were enough to make my ass like butter in her grasp. She let more saliva roll down my ass, lubricant for her finger. Bit by bit, I allowed her to push me to new lengths. A second finger curved into place, pushing into my ass. My hole clutched to each finger, pinning them in place. Gasping, I pulled away, only to have her grab my thigh forcing me to stay in place as she continued to push, sinking right up to the hilt. Her two fingers danced inside, twisting and shifting, probing my asshole. I was loose enough by her measure. I’m not sure whether I would have preferred her to continue adding fingers or what came next. Actually, I do know which I would have preferred. Frankly… Frankly I would have liked her to continue adding fingers and then did what she did next.            I watched her hand reach past me, her fingers leaving my ass as she grabbed the lube. Breathing deeply, I kept my gaze forwards as she squeezed several drizzles of lube onto my ass, letting it sink into my hole as she then began to lubricate her cock, lathering her cock. It took a minute at least for her to coat the entirety of her shaft. At the end, she set the lube back on the nightstand, allowing me to catch a single glimpse of her hand, doused in the substance. And then I felt the cockhead rest against my asshole, quite unlike anything I expected. I suppose the unusual shape was to blame. Moaning, I braced myself as she slowly applied pressure, inching and easing forwards. I was surprised by how easily my arse gave away to her demands. Before I could even consider clenching my asshole, the head of the strapon had disappeared inside of me, my asshole fitted snugly around the plastic strapon. My breath was stolen from my body, as pain and pleasure became one, each fighting the other to take hold. As to which one took hold in the end, that would be pleasure. Katy’s free hand went to my cock, still rigid and thick beneath me. Massaging and squeezing it, she jerked me off until the pleasure of my ass being mutilated was all that I felt.            I couldn’t rightly tell you exactly how I did it. Yet, over the next few minutes, Katy continued to push forwards, jerking my cock until my ass relented. Inch after inch of solid, thick plastic pushed into my asshole. Eventually, it rested against my prostate. The next inch crushed it, squashing every last ounce of pleasure from my body. Moans and groans escaped my lips. Breathing heavily, my asshole stretched and warped until finally, Katy’s crotch rested against my ass cheeks. My eyes widened as I felt it. I had taken every single inch inside of me. Every single inch. And I felt… felt pleasure. Intense pleasure. I cannot believe it even now. Finally, she gave me a chance to breath, to relax, to adjust. I can only imagine how my asshole looked at that moment, stretched tightly around the thickness of her monster cock. Her hand continued to move along my cock, my shaft twitching, spraying several long strands of cum out onto the sheets below. Yet… Yet, my cock didn’t even begin to soften. My prostate was massaged and squeezed in every respect, keeping my cock completely hard, refilling my balls with more cum, more arousal from the pleasure. I wanted it. I needed it. It filled me to the brim, filled me with pleasure and purpose. I loved it. No longer did my fantasies concern fucking Katy, turning her into my bitch, my sex-doll, but instead with me becoming hers. All I can remember from that moment is how much I wanted her to start moving, to start fucking me. To show me true pleasure. In all its glory. And she did just that. From the beginning, she had no intention of simply challenging me to take her strapon, but instead, to be fucked mercilessly; as a filthy cum-rag. A cum-rag for her pleasure. That’s all I wanted to be in that moment.            Drawing her hips back, she eased half of her cock out of my ass, all before thrusting forwards, driving herself into me with such power that had been missing from her initial push. I gasped, letting out a moan that followed as I felt the suddenness of it all. Before I could adjust, she had moved again, pulling even more out of my ass and sliding it back In. She wasn’t pounding me; at least not by her measure of the word. No, she was yet to unleash the full temperament of sexual prowess. Lazily dragging her hips back and forth, she added to lubricant with her saliva, her hands pawing and groping at my ass cheeks, grabbing my flesh and hauling me backwards to meet her cock. When she figured out that I was feeling pleasure; that I was enjoying it, she began to increase in power, drawing herself in long and languid thrusts. My cock continued to dribble pre-cum and cum like a faucet, down onto the sheets below. I wanted to touch myself, yet I knew that it would add nothing to the pleasure I was feeling. My prostate hummed in ways that couldn’t describe.
            The best part was that I had cum, yet I was not finished. I was not finished. Nor was Katy. She felt no pleasure aside from the satisfaction of fucking me good and proper. She was going to fuck me until that satisfaction dried out. Pounding away at my ass, she continued for an hour. Maybe two. My cock continued to leak, drenching the sheets below me. Moaning deeply, I was fucked hard and mercilessly for several hours, all in that same position. Bent over on all fours, driven into like a hound takes a bitch. Again, and again. Finally, when I was weak and unable to support myself, I collapsed forwards, gleaming and dripping with sweat, a sordid mess of weariness and pleasure. Breathless, I lay, trying to garner some strength to turn and face Katy. She drew the strapon out of my ass, grinning as my hole gaped, wider than anything she had seen before. It would take several days for my ass to look somewhat normal. Suddenly, a slice of paper entered my vision and turned to look to my side. A five-pound note. With a giggle, Katy purred, "For your troubles... The cheapest whore I've had..."

Credits:
Image Creator: celebrityfakecocks (Tumblr deleted and unable to find elsewhere)

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