Prison Fling

by Cassandra Dee

  “Up?” came my weak gasp. “What do you mean, up?”

  By now, Mason, Kane and Tyler had lined up, three massive forms standing, their dicks protruding outwards, the tips so wet that they dripped onto the floor.

  “Honey,” rasped Kane. “You’re gonna ride the dick wall. We need you to do it because this is your first time. We need you to push yourself back on us, breaking that pretty pussy on your own.”

  My mouth dropped. No way could I do it. Most girls hold still the first time, flat on their backs, while the guy does the honors right? It’s easier that way because there’s pain and straining, blood that’s gonna run.

  And yet, I was in a completely different situation. I was gonna have to push myself backwards onto three huge shafts, impaling myself onto monster dick times three. No way. No way could it happen. I’d melt into a puddle, or give up after the first one, collapsing into a mess on the floor.

  But three pairs of blue eyes bored into mine, electrifying in their intensity.

  “You can do it,” growled Kane. “You can absolutely do it.”

  “Just try,” added Mason, gesturing to his shaft. “Try it pretty girl, it’s not so bad.”

  “We need you to,” finished Tyler. “Because virgins don’t do three guys at once, not usually. So we need to be sure you want it. And by pushing yourself back on us, you’re telling us yes.”

  I couldn’t move for a moment, trembling like a deer in the headlights. But suddenly it all made sense. These guys wanted me to be in control. They wanted me to feel like I was the woman in charge, that it wasn’t three alphas pushing themselves into on a virgin. So this was how they did it. I was going to break my hymen of my own free will, driving backwards of my own accord until that special tissue was gone.

  And suddenly I wanted it. I wanted to be the new Katie, the one who owns three men, billionaire alphas kneeling at her feet. I wanted to show them that I was adventurous, wild, and hot as sin, able to perform with the best.

  Because I am that woman now. I’m the girl who took them three on one in a public space, at a wedding reception no less. I’m the one in their hotel suite now, who just had her pussy and ass sampled. And I wanted to be the girl who enjoyed this encounter to the max, letting herself get dicked times three.

  So on wobbly legs, I walked to them, huge tits jouncing, before bending over in front of Tyler. My brown curls almost brushed the floor, fingertips trailing the ground. And slowly, my head turned so that I could catch his eyes with my own.

  “Like this?” came my slight murmur. “Like this, big boy?”

  Tyler growled possessively then, blue eyes flaring, big hands on either side of my waist.

  “Just like that,” he grunted, letting his dick tip brush my hole. “Just like that sweet thing. Now back up onto me. Show me how much you want it, baby girl. Push.”

  And with that, it began. His glans nudged my sweet spot once more, and closing my eyes, I went with it. My hips moved backwards, catching that purple helmet in my small hole. But I stopped for a moment, pausing.

  Because it felt heavenly. My pussy was drenched, and the big man’s cock pried me open, lodging just within my channel before slowly moving upwards, stroking my sweetest spot.

  “Ahhh!” came my involuntary cry, eyes falling closed. “Ahhh, ahhh!”

  But again, the men wanted me to assume the driver’s seat.

  So Kane growled from his position by us.

  “Push yourself back, baby girl. Don’t let him do the work. Shove backwards honey, take that dick into yourself.”

  And gripping my ankles tighter, I did it. At first, it was more of a lean as that thick shaft tunneled into my sopping cunt. But then it happened. His tip brushed against something deep inside, sending a twinge through my pussy, making me shiver.

  Tyler grabbed my hips again, whispering hoarsely.

  “That’s right, baby girl. We’re there. Do it, honey, do it.”

  And with a scream, I obeyed. I pushed back forcefully, impaling myself onto that monster cock, breaking my hymen in one sure stroke. And a growl rose up from the men then, melodic and uniform, as my pussy tasted cock for the first time.

  “Ahhhh,” they roared. “Aw fuck!”

  But I’m a slut now, and once wasn’t enough. So I rocked forwards again, letting Tyler slip out, before pushing back once more, fucking him sinuously, my big boobs swaying this way and that.

  “Oh oh oh!” came my desperate cries. “Oh!”

  I was ready to burst right now. And sensing the rising waves, Tyler pulled out then, his dick dripping and glossy with pussy nectar.

  “Not yet, sweet thing,” he rasped. “Not yet. Kane,” came that deep command.

  And the second billionaire took his place behind me, that thick dickshaft tickling my hole once more.

  “Back up,” the deep voice coaxed. “Just like the first time.”

  And again, the stretch was incredible. Kane was just as big, and my pussy is small. Never mind that they’d helped me relax, that I’d just had a cock in there a second ago. It’s always incredible, and I let out a low, throaty moan as once again, I impaled myself onto a second massive dick.

  “Unnnh!” came my inarticulate cry, boobies bobbling as I got fucked. “Unnnh!”

  “Aw shit, she feels so good,” was Kane’s harsh rasp. “So fucking good.”

  “Savor it brother,” came Mason’s low growl. “Savor it because I’m up next.”

  And using his moment in the spotlight to the max, Kane pushed in and out a couple times before withdrawing completely. I almost cried, my hole was so empty now, vaginal chamber clamping and clenching, begging to be filled.

  But Mason was ready. In a flash, the big billionaire nudged my pussy hole with his dick, leaning over my back to whisper sweetly.

  “Last time, baby girl,” was his low assurance. “And trust me, you’re getting spunk this time. Lots if it.”

  And with a wild cry, I did it. Pushing back, my pussy swallowed that massive shaft whole, loving the deep penetration, savoring the experience.

  “Yes!” came my shriek. “Yes, yes!”

  Because this was beyond my wildest dreams. I’d just taken three cocks into my virginal body, my hymen broken by my own accord. I’d just harbored three giant, massive fuckshafts, coating them with female juice, branding them with my own personal scent.

  And they loved it. The billionaires loved it, watching me get fucked, staring hungrily as those thick poles disappeared into my sweet snatch, coming out with traces of red on the sides.

  Because yeah, it hurt a little. There was a tiny sting in my pussy deep inside, like a pinprick. But it was already dissolving, and going for it, I launched into action.

  “Fuck me!” came my scream. “Fuck me Mason! Fuck me Tyler! Fuck me Kane!”

  And Mason sprang into action then. Grabbing my hips, he began pummeling my pussy, fingers tight on my flesh as his dick did its business.

  “Aww fuck,” was his bitten-out cry. “Aw fuck fuck fuck. You’re so tight.”

  “I’ll say,” rasped Kane, watching with avid eyes as my butt bounced and jounced with each hard pound. “Give her the deep dicking she needs.”

  And Tyler reached over then, all the while stroking his fuckshaft. With one clever finger, he stroked my anus as Mason pummeled me in back.

  “Let go, little girl,” came the command. “Let go and let us see you explode.”

  I had no other choice. I had to obey, there was no other way. And like a fireworks display, it happened then. Release rushed through my frame, cunt exploding in a shower of sparks as I screamed wildly.

  “Yes!” was my belted-out cry. “Yes, yes, yes!”

  And with that, my pussy and ass clamped wildly, squeezing on the hot shaft within. Mason came immediately, jerking once, then twice, before releasing a hot stream of spunk deep within.

  “Fuuuck!” came his roar. “Fuck fuck fuck!”

  But before he finished, the big man pulled out, letting Kane take his place.
/>   And in one swift push, Kane was inside once more, coming like a fire hose.

  “Milk it,” he gasped, pumping deep within my recesses, spraying my vaginal chamber with hot man seed. “Milk my cock sweetheart.”

  I cried out again, the spasms in my cunt unstoppable, electrical jolts running all the way to my fingers and toes. The top of my head was gonna blow off, I was going to dissolve into a puddle right here, right now.

  But there was one more billionaire, and Tyler wasn’t missing his turn, no way no how. Because after Kane let out a few great spurts, he withdrew, and suddenly Tyler was deep within, blasting me with baby batter.

  “Unnh,” the billionaire grunted. “Unnh, unnh.”

  Oh god, this was so dirty. I could literally feel Tyler’s penis as it pulsed, the veins on the side hot and throbbing as he jerked and sprayed within my inner chamber, pumping me full of virile sperm.

  And it only caused me to go buck wild all over again.

  “YES!” I screamed to the heavens, “Yes!”

  And that’s how I lost my virginity. It’s wrong, I know. I took three cocks within the space of five minutes. I let three men sample my insides, breaching my tiny hole, pumping me full of sperm as they saw fit. And I should be regretful. I should be shocked, I should feel dirty and unwhole, like a handmaiden forced to wear a scarlet letter.

  But instead, all I feel is good. Because Mason, Kane and Tyler care about me. After they finished unloading spunk deep inside, each of them kissed my pussy tenderly, licking deeply at the swollen folds.

  “You okay honey?” murmured one, lapping at the oozing slit. Oh god, oh god, he was literally tasting the cum of three men mixed together, the sweet and salty of various DNA. But they weren’t turned off at all. Instead, all three of them knelt in back of me, worshipping the sweet hole that had serviced them all.

  “I’m okay, I think,” was my trembling whisper. “I think I’m okay.”

  “Just okay or great?” teased Kane from in back of me, his tongue playing with my clit once more. “Good or great?”

  And I giggled breathlessly because suddenly, everything went alert all over again. Could it be? Was I really ready to play again, so soon?

  But it was true. Because Mason licked my asshole then, pulling apart the great white cheeks to get at my brownie, his tongue going up my rectum this time.

  “Ahhh!” came my scream. “Ah ah!”

  “Thought so,” he growled knowingly from behind. “Thought you liked it.”

  And that was the truth. I more than liked it, I loved it. I loved everything they did, everything they’d taught me. It was beyond my wildest dreams, yes. It was beyond reality, pushing me into fantasy-land, a crazy sequence of events that was beyond comprehension.

  And yet I adored this fantasy. I loved what had happened to me, here in this luxurious hotel suite, nude and trembling with pleasure even now. I relished how the billionaires made me feel, like a precious jewel, something to be cared for yet enjoyed. And in my deepest heart, there was always the truth that I wanted more. I wanted to see where this could go, and what can possibly become of an illicit relationship … with three men.

  CHAPTER NINE

  Katie

  Walking in the door of my apartment, things felt different. I felt different. The smile hadn’t left my face since leaving the hotel room. Mason, Kane and Tyler tried to entice me to stay the night, but I wanted the comfort and familiarity of my own apartment to process my thoughts and feelings about what just happened.

  My mind kept running over each moment of our illicit encounter. The billionaires had sent me spiraling over the edge into oblivion for sure. Making me purr with pleasure. Making me hum with a new awareness. Somehow, I didn’t think I’d ever be able to get enough. They’d made me feel desirable and beautiful, like Miss America times ten.

  Carelessly, I kicked off a heel and watched it sail across the room, landing with a thud on the throw rug in the living room. Then the other one followed, landing a couple inches away from its twin. My mood was playful as I danced around my apartment, turning on lights. Humming some indistinguishable melody, I entered my room, fingers making quick work of the buttons on my blouse. Memories flooded me of Tyler’s sure hands unfastening the shirt and my body shivered.

  Next my skirt joined my blouse in a puddle of clothing on the floor. I padded to the bathroom naked and twisted my hair up into a sloppy bun.

  As the light came on, I caught my reflection in the bathroom mirror and gasped. Was that really me? The girl with a flushed, healthy glow, a certain je ne sais quoi in those sparkling brown eyes? With the lips that were bee-stung and full, a happy, sated look on her face? Turning my chin this way and that, my eyes took in the new me. Yes, it was definitely me. The same girl who’d just had three gorgeous, alpha, billionaires take her virginity.

  “You loved every minute!” I murmured naughtily, grinning at myself in the mirror, before giggling with unabashed humor. Yes, I enjoyed every minute spent in their company. And seeing myself through their eyes made me appreciate my figure that much more.

  Because I was big then, and I’m big now. But studying my reflection, there were love bites on my breasts, the marks of teeth on the undersides of those full curves. There were fingerprints on my hips where they’d squeezed me tight, and oh god, a hickey on my throat. I was gonna have to wear a turtleneck tomorrow at work, otherwise there’d be wry looks and insinuations.

  But it was nice for a change. Real action had happened, instead of made-up stuff with a fake long-distance boyfriend. I actually looked well-fucked, instead of the shy, bumbling girl that was my usual persona.

  And stepping away from the mirror, I hummed merrily, turning the shower on, running my hand beneath the head as the water heated. Oh yeah, this was much needed. The warm spray from the nozzle hit my sore body as I stepped in. Would it always be like this? Would it always feel so good to take three men, letting them use my body, becoming their plaything?

  A delicious ache throbbed between my legs, and experimentally, I touched down there. Oooh, soft and hot for sure, swollen a little too. But suddenly, a warm gush of cum slid from my hole, drenching my fingers unexpectedly. Oh god, oh god! Because this wasn’t just one deposit of sperm. This was the residue from three alpha billionaires.

  A delicious shiver ran through my core once more. Yes, I’d done it. I’d let three men use my body, going raw and spurting deep inside. It was wrong, I know, but I couldn’t resist. Lifting my fingers to my lips, my eyes closed as I sucked at the digits, savoring the man milk on my tongue.

  “Ummm,” came the appreciative moan, unbidden and throaty. The semen was tangy and gooey, the perfect dessert. “Ummm.”

  Suddenly, my eyes fluttered opened. Oh my god! I wasn’t on any sort of birth control! And to add fuel to the fire, not one, but three men just sprayed deep inside. Oh shit! Immediately, my back jerked straight, thighs clamping shut. Plus my age. At twenty-two, no doubt my body was fertile, just waiting to ripen with a child.

  Oh god, oh god. What had I done? Because yes, while the sensation of each man bareback inside of me was incredible, I couldn’t help but shrivel a bit. Talk about reckless and careless! And the chance that I’d get pregnant was multiplied by three, right? Three times the goodness, three times the opportunity? Oh god, my brain whirled crazily.

  Not only that, but Tyler, Mason and Kane were strangers no less. Numbly, I reached for the shampoo bottle, squirting a big glob of soap into my palm. I still didn’t know anything about the alphas, not really. And lathering the shampoo into my hair, my inner voice chastised me once again.

  How could you do that? it screamed. You know better than to have sex with strangers. What were you thinking? You’re done for now, Katie.

  But it was too late. The dick wall had already happened, and I’d taken them deep into my body, welcoming the penetration. Not only that, but I’d opened my heart their personalities as well. I’d let myself entertain new horizons, exploring the unknown.

  Bu
t all this could be rectified. I was going to get to know them. Biting my lip, the suds ran over my body, slippery and wet. I wanted to know Mason, Kane and Tyler. The three billionaires were a gateway to a different world … and a new me.

  CHAPTER TEN

  Tyler

  “You almost ready, bro?”

  I slipped on my suit jacket.

  “Yeah, be right out.”

  The clock on the wall read almost noon. I could only smirk when Kane told us we’d meet downstairs today. Guess Katie was afraid there would be a repeat of last night’s activities. Yeah, we all had some fun last night, and the girl seemed to love it. Of course we never have complaints in that department.

  Throwing one last glance in the mirror, I shook my head. Last night she’d been the star attraction in my fantasy and I’d jacked off in my hand remembering the slick glide of her pussy.

  But there was more to her than just the physical. There was the pure innocence, her honesty and wholesomeness. There was the way she trusted us, giving her all while holding nothing back. Hell, we needed to teach her about that. You can’t keep giving like that, you’ll be left with nothing.

  But that’s one of the things I love about Katie. Because her generosity’s boundless as far as we can tell. The female’s a well of goodness, pure and sweet, and she’d give the clothes off her back before slamming the door in someone’s face.

  Shit.

  What have we gotten ourselves into?

  She’s too good for us.

  She’s way too good for a weekend fling, that’s for sure.

  So what now?

  But first things first. When the elevator doors opened revealing Katie standing in the lobby, all thoughts flew from my mind. Because even buttoned up in her business suit, the girl looked like a pin-up model. Sassy, shy and sweet, all at once, those Double Ds barely hidden behind a loose blouse.

  And Kane and Mason were definitely on the same wavelength, eyes transfixed, bodies hard already. Shit, what she does to us. It’s insane.