Claiming His Virgin In the Ring: The Filthy Wrestling Club

by Cassandra Dee

  “Oooh,” I gasped, my face flushed, hardly able to breathe as my pussy stretched. “Ooh!”

  And slowly, oh so slowly, I began bumping my hips up and down the dildo, letting the hard rubber slide in and out, the glossy shaft running in and out of my cunt. It wasn’t easy that’s for sure, I had to go slow, my pussy had just been de-virginized and I was still unbearably tight, my twat so fresh, still taut and new.

  But I wanted to make sure I was doing it right, that the audience was getting a good performance. So as I worked my hips, I swiveled around to look at the big man, winking over my shoulder.

  “Tristan, Tristan, Tristan,” I whispered. “You like?”

  And the big man couldn’t answer, he was so turned on, eyes glued to my cunt as the dildo ran in and out, cream dripping wetly from my snatch.

  The view in the mirror must have been amazing, my little pink hole fucked so hard, penetrated so fully by the rubber, seen clearly in the mirror. And the harsh rasping sounds from Tristan’s chest, his hand flying on his cock, the fact that his balls were high and raised indicated that everything was going just as planned, that the big man was about to let fly at any moment.

  But I didn’t want him to shoot without performing the finale, playing out a little fantasy I’d just crafted in my mind. So lifting up again, I let the dildo slip out, inch after inch of slick rubber dropping out of my cunt. With a clever twist of my hand, I wrenched my panties to the side so that my asshole was exposed and backed up a few inches. Without further ado, I began sinking down again, letting the rubber probe my anus, the brown pucker tensing and winking as the hard shaft sought to make entrance.

  “Oh!” I squealed. “Oh oh oh!” Even though I’d been an ass virgin up until last night, I was so turned on that I was sure I could do it, I could impale myself on this huge rubber dong coated in pussy cream. And so I worked my hips, jiggled them a little, squealing and whining as the rubber probed again, shoving my butt down, forcing the toy up my ass. And after some twisting and turning, wriggling and humping, the dong finally made its way inside with a pop, my sphincter giving it up.

  With a sigh, I slid down all the way, burying the shaft in my behind, my anus on fire, achy and sore at once, the tight rim burning so good.

  “Oh god,” I moaned, on my knees leaning forward, pausing for a moment, boobs heavy and pendulous, swaying rhythmically as I caught my breath. “Oh god.”

  But there was no rest for the weary.

  “Move,” ground out the big man, his eyes fixed to my butt cheeks, eyeing the part where the rubber disappeared into my anus. “Assfuck yourself,” he commanded.

  And as if in a trance, I lifted my hips again, letting the pole slide out of my butt, burning like fire before dropping down again, humping it, the friction so delicious, so sexy. And soon enough I was going at it full-steam, banging the dong, gyrating, wheeling, twisting, fucking my rectum again and again, gasping, shrieking as it reached up into my GI tract, the fit so tight, so dry.

  “Shit!” I screamed, throwing my head back. “Shee-it!”

  Because I couldn’t take it anymore, the dirtiness of everything, the red crotchless panties mixed with the mirror-mounted dildo, the pussy-fucking, the ass-fucking, the fact that I was putting a show on for my guardian. Sensations overwhelmed me and I came hard. My body pulsed and shook, earthquakes running through my frame, all of it centering around my quivering clit, ass and pussy clenching and clamping with orgasm, shaking so hard that I thought I might yank the dildo right off the mirror altogether with my vibrations.

  And Tristan was having a field day too. The big man’s hand was a blur on his cock now, chest and abs tight, that massive form on fire, eyes gleaming as he stared at the ass slide. With a roar, he slipped one hand down to his balls and squeezed them tight as he came, penis erupting with lash after lash of semen, drenching my back, my butt, my skin splattered with splashes of hot cum. Holy shit, jizz was even running down into my buttcrack, dripping into my asshole.

  And I couldn’t take it. I wanted it so bad that I ran a finger to the site and scooped up some of the semen, tasting it first, licking my lips before reaching back down to massage it into my pussy, working the sweet jism into my tight space.

  “Mr. Marks,” I breathed, seizing his eyes. “I need more,” I whispered, and with a roar Tristan was on me again.

  CHAPTER TWENTY-FIVE

  Daisy

  I wish I could say that everything was a happily ever after, but it didn’t turn out that way. Life isn’t a fairy tale, and things with my guardian didn’t work out, unfortunately.

  Oh sure, things were fine for the rest of the weekend. After I performed my little dildo show, I was floating on air, feeling nothing less than spectacular. The big man wouldn’t let me out of his arms, carrying me into the shower with him, making me bend over and take it, this time with his dick instead of the dildo all the while whispering raunchy promises in my ear.

  “You got that, baby girl?” he rasped into my ear. “Only Mr. Marks touches you, only Daddy’s cock goes in that sweet pussy. You belong to me.”

  And what could I do but gasp and nod breathlessly, my insides quivering, cunt fucked so good. Because there was nothing for me except Daddy, nothing for me except Tristan, my nights and days were filled with him, my thoughts complete, whirling with sensations, the power and glory that was being with this man.

  But once we got home, things ground to a halt. And I mean everything stopped - the sweet nights in bed, the dirty playtime, the intimate confessions, the emotional admissions. On the one hand, I hadn’t been completely sure that Tristan loved me because there were no words. But it sure as hell seemed like it. There was every indication that he wanted me, that it was more than just a one-time thing, that I meant more to him than a velvety, nubile body available for his desires. After all, there’d been the time in the chapel, the library, the multiple times he’d looked at me with emotion in his eyes, words on the tip of his tongue.

  But that’s the thing. Tristan never actually said, “I want to see where this goes,” “Let’s keep seeing each other after this weekend,” or even a measly, “I like you a lot.” I can’t say what I expected exactly but certainly not what happened next.

  Because when we got to the doorstep of his mansion, the big man drew me close to him, pulling me in for a deep kiss, gazing into my eyes, those blue eyes penetrating, so knowing, before swatting me on the butt.

  I’d giggled deliciously, figuring that this was the foreplay to another round of steamy sex, that we were just teasing, heating things up before taking them to the next level. And Tristan seemed to be in a good mood.

  “You’re cute, baby girl, so delicious,” he growled and I tittered, stepping into the foyer, our luggage a pile behind us. Oh, where was that sexy thong and the dildo? Packed in my bags and ready to be used again, pulled out in a flash.

  But oddly, I didn’t see Mr. Marks that night. I wasn’t sure where he was, maybe buried in work too busy to eat, and so I sat alone at the dinner table in my babydoll dress, feeling idiotic as I swung my heels like a child. Back down, I scolded myself. Tristan’s a busy man and took time out from his schedule to chauffeur me upstate, show me around his alma mater. He needs to catch up, to see to his empire. Besides, there’s tomorrow. There’s always tomorrow.

  But the big man was a no show the next day as well. Tristan didn’t come to dinner, didn’t knock on my bedroom door, didn’t intrude unexpectedly, didn’t even seem to eat anymore. In fact, it wasn’t clear he was in the house, it was so quiet, the mansion dim and gloomy, just my lonely steps echoing on the marbled stairs. Where was he? Where was my guardian? Why wasn’t he making an appearance? Didn’t we have a connection of some sort?

  But evidently Tristan could turn emotions on and off in the blink of an eye, his iron control and steely will making the impossible possible. And so I shook, shoulders heaving, my heart slowly folding in on itself, crumpling underneath the realization that I’d been nothing more than a fling. On the outside
I looked okay, going to class as always, smiling and laughing as part of the cool crowd at school, cooing at cute boys, pretending that I was interested in a million things. But it was a mirage. I was a ghost floating among tumbleweeds, hollow, soulless, eyes hot from crying myself to sleep each night.

  And even my last hope collapsed. I thought for sure Mr. Marks would show up to my high school graduation. As I sat there under the sun, mortarboard perched on my curls, my breast fluttered, heart leaping in my throat. Was Mr. Marks here somewhere? My eyes scanned the crowd reflexively, pulse jumping. Was he here? Had my guardian come to see me on this big day, to usher me into the next phase of life?

  But there was no sign of the alpha male among the proud parents, the smirking siblings. There was no dark, looming figure, no gleam of blue eyes, no raffishly ruffled hair. Among the chattering crowds, there was no huge, masculine frame, ready to catch me up into an embrace, or even to share an awkward hug. I was alone, just like always.

  So heart heavy, I turned within myself. Slowly but surely, my mind shuttered as I consciously tried to block out thoughts of Tristan and our wild weekend, to focus on the life ahead. There was no sense in mooning over the impossible. I’m an eighteen year-old girl with the world at my feet, a ton of opportunities, about to enter the most exciting phase of my life. So why wasn’t I more excited?

  Because despite the happy smiles, the perfect clothes and sassy figure, life has gone dim. The fact is that I still crave Tristan, miss Mr. Marks so much that my bones ache, and every night alone in my dorm bed is a painful reminder of what we had, his big frame loving me, owning me completely. Those blue eyes saw deep into my soul, and I really thought we had a connection. But clearly, that’s not true. I was nothing more than a dust mite to the big man, a fun weekend fling with a nubile female body, and although reality hurts, life has to move on. There’s no other way.

  CHAPTER TWENTY-SIX

  Tristan

  A year later …

  “Sir, good to see you again,” bowed Bowles, my butler.

  “Thanks, it’s been a while,” I rumbled, stepping into the foyer of the New Jersey mansion. It was quiet, but then I expected it to be.

  I haven’t been back in a year. I took off after my illicit weekend with Daisy, realizing that I was playing with fire, that we were both going to get burned to cinders, going up in flames. Because Daisy was gorgeous, funny, smart, and ambitious. She was everything I needed, everything I’d ever wanted. But the fucking problem was me, an older man cum lech who used that nubile body every which way when the sweet teen didn’t know better.

  Because sure, she was eighteen but that hardly excused things. I’d been ordained by her mom to take care of her, make sure the girl didn’t get into trouble. But instead, I’d been the cause of the trouble, popping her daughter’s cherries, violating all my promises. For one illicit weekend, one incredible, once-in-a-lifetime occasion, I let myself revel in the taboo, take what I’d wanted, however I wanted.

  And it had gotten out of hand. True, Daisy and I had been careful – to the outside world we were just a guardian and ward on a college tour, visiting my alma mater, nothing special. But holy shit, it was so much more than a simple tour of the campus. I showed Daisy the Labyrinth, the down and dirty nook in the library where couples got it on, taking her cunt, her ass, her virginity, her everything.

  And after it was done, she was so good, so tasty that I needed more. I fucking went ape-shit, putting it in her ass, making her cry out and scream, forcing her to fuck a dildo for crying out loud. Who does that to a virgin? Who the fuck? Me, that’s who, and I hated myself for it. I’m so depraved, such a fucking user, and I’d taken that girl for all she was worth, sating myself, watching that pink pussy pulse around my cock again and again.

  But I couldn’t live with it. I’d violated my sacred oath to Carolyn, I was the monster in the closet, I’d made promises and instead, taken from the vulnerable, the needy. And fuck, but as CEO of Marks Holdings, I’m responsible for a vast portfolio of publications including publications like Sixteen, a teen rag for adolescent girls. What would the subscriber base say if it got out that I was banging my ward? That the guy who literally founded Everyday Dads and put Rachel Lewis Living, Healthful Life!, and Moms and Tots on newsstands was now drilling an eighteen year-old night after night, parting those cunt lips for countless sperm deposits? It was fucking bad business and there are shareholders to keep happy, a business to run.

  So I took off, leaving for Europe, managing my conglomerate long-distance. My staff was aghast at first, stuttering and grasping.

  “Mr. Marks, we need you in New York. Who’s going to preside over the board meeting?”

  “Mr. Marks, we’re looking at three executive hires, we need your input at the senior level.”

  “Mr. Marks, we need you for the quarterly earnings call. It can’t happen without you.”

  We need, we need, we need. I ignored it and as expected, the problems magically resolved themselves. Or maybe the problems had never been problems to begin with, they’d merely been the nervous blabberings of annoying underlings.

  So yeah, things worked out business-wise, I’ve still got Marks Holdings under control, our shit is selling like hotcakes, money’s pouring in in waves, making me a very rich man.

  Except that I’ve been miserable here in Europe, missing my little girl. I’ve tried my best to keep my mind off her, taking out a bunch of highly eligible women, supermodels, PR chicks, marketing babes, all of them six feet tall in stilettos and cocktail dresses, glossy hair swinging over their shoulders, stick thin with calculating smiles.

  But I’ve felt absolutely nothing. I smile, flashing a grin for the cameras, my arm around their waists, but I literally can’t focus. The women jabber on, their voices running like water through my head.

  “Tristan,” the latest one purred, hanging off my arm.

  “Hmm?” I replied, turning distractedly to her. What was her name again? Oh right, Jenny. I’d agreed to be seen with Jenny because she had brown hair, the waves rippling under the light, reminding me of another woman, a sweet, sassy girl.

  But just as she was about to speak, a photographer ran up and snapped a pic, the flash bright in our faces. As if on cue, Jenny struck a pose, jutting her hip out, throwing herself into my arms, and I reflexively caught the woman as her body pressed tight to mine, not an inch of daylight between us. But as soon as it was over, I pushed away, disgusted. The female was so thin, so frail, all skin and bones, like I’d been hugging a skeleton and not a ripe, curvy female. What I wouldn’t have given at that moment to feel Daisy’s huge tits against me, those pillows molded against my chest, that sassy ass wiggling and jiggling. Fuck my life, dreaming about my ward even while on date with an international supermodel. I was so fucked.

  But work has brought me back to New York now. Marks Holdings is in talks to buy PrettyGirl, a “gentleman’s magazine” of the best sort, the kind where girls go at it triple-X style, baring everything, pushing everything and anything into their cunnies. Naw, this wasn’t soft-core stuff, not like Playboy where you see breasts but no ass. This was no-holds-barred real shit, skimming the line of vulgarity, dicks out, tits out, cocks in cunny.

  And fuck, but sex sells, bringing in shitloads of moolah, far more than Sixteen or Moms and Tots, our current cash cows. It’s not PrettyGirl, the magazine itself, but rather the on-line website. People purchase subscriptions to PrettyGirl.com for fifty bucks a month and there were currently twenty million subscribers. That’s one hundred million in cash per month. Count it, folks. One hundred million dollars. Per month. And that didn’t even include the live streams, the on-air talk show, the “talent” that circled the world dancing at various clubs. We were talking some serious bucks, my empire would expand dramatically with the acquisition of this beauty.

  But PrettyGirl’s an odd one. It’s still owned by the original founder, Jerry Echo, a sleazy douchebag of a dude, seventy and constantly wandering around Hollywood with three blonde
starlets on his arm. He’s fucking disgusting, there’s no way that guy can get it up without Viagra, but hey, to each his own and he’s built an empire on his image, living the life in a silk bathrobe and wheelchair.

  And Jerry wants to make sure his baby is sold to the right buyer. Old fuck Echo wants to make sure that Marks Holdings has a niche for the magazine, that we’re going to market it well, that we’re going to keep feeding his pet project, max out its value even after he hands over the reins. And so I’ve got to change my image. Gone are the days of Tristan Marks, alpha billionaire, model-dater, serial womanizer, the man with the Midas touch. Hell, that was the old shit, way too tame for Jerry’s tastes. He wants someone in his image, someone who’s just as nasty, dating girls decades younger, sweet and nubile, sassy and fun, and I know just how to get it. I’m re-branding myself as Tristan Marks, billionaire alpha … and the asshole who seduced his innocent ward.

  CHAPTER TWENTY-SEVEN

  Daisy

  Life at school has been fun. Browning is in downtown Manhattan and there’s no campus per se. Instead, the administration refers to the city as our campus, all of New York at our fingertips, Lincoln Center, countless museums, heck even the High Line and Freedom Tower as outstanding examples of art and architecture, intellectual stimulation for the mind.

  And it’s been fun so far. I’m enrolled in a bunch of writing classes, I figure I’ll need them if I become a lawyer, and I’ve started volunteering with Legal Aid at the Courthouse. It’s not much, I do intake for prospective clients, taking down names, scanning IDs, making sure that all the folders are organized, all the forms where they need to be. And I like it, it’s nice to work with folks who appreciate you, the clients happy to have someone to listen, a sympathetic ear even if I can’t do much else.