Prison Fling

by Cassandra Dee

  “Oh god,” she moaned the entire time, breasts swaying as she fucked her own ass. “Oh god, yes.”

  And after a couple more deep slides, I hocked once more.

  Immediately, her head turned, eyes wide as they met mine.

  “Wha--?” was her surprised gasp.

  But it was too late.

  Because slowly, I added another finger into her butthole, prying that dark star open.

  “Unnnh!” came her strangled moan. “Unnnh, oh!”

  But my buddies were on it as well. Watching with hot eyes, Kane started stroking her clit, loosening that pussy up. And Mason began tweaking her nipples, sending jolts from those hard nubs all the way down to her cunt.

  “If you feel good all over, it’s easier,” I crooned once more. “Keep going,” I directed my friends.

  And slowly, I pushed my fingers in deeper, breaching the dark space.

  “You can do it,” came my sensuous growl, rubbing against her rectal walls. “Relax your ass honey. Let my fingers in, it’s the only way.”

  And Katie’s a champ because taking a deep breath, she pushed her ass back then, swallowing the two digits while moaning musically.

  “Tyler! Kane! Mason!”

  Aw fuck. The three of us shared a glance over her smooth back. This girl was the answer to our dreams. A whore in private, yet pure, wholesome sweetness in public. We needed it, bad.

  And in a flash, my dick was out. I needed to be inside of her. Popping my fingers out of her rectum, I gripped the beast, rubbing the tip between her nether lips.

  “Just getting lubed up,” came my hoarse grunt. “Just getting some of this nectar so I’m nice and wet.”

  The girl moaned again, head dropping down, hips bucking backwards reflexively, like she was trying to catch my dick in that juicy pussy. But this wasn’t the time.

  “Naw sweetheart,” I panted. “We’re taking your ass cherry remember? We’re gonna bust that one good tonight.” And with that, I aimed my pole at her dark star.

  Oh god, she was so small, the pleats contracting at the brush of my dick. But familiarity will do a lot. So spitting onto the tip of my cock, I began to rub my cock on her anus, spreading the goodness while warming her up. Shit. My hips jerked forward at how good it felt and I wasn’t even inside yet. Adding a bit more saliva, another groan escaped me.

  “Relax sweet thing,” I rasped. “It’s going to feel weird the first time. There’s going to be pressure, so relax and take a little of me at a time.”

  Katie could only nod her head wordlessly as the tip of my cock began to work its way inside her anus.

  “Unnnh,” she moaned again, holding completely still as the penetration began. “Oh god.”

  Mason and Kane were on it too, gripping her hips, making sure her nips got rubbed as that back star was breached.

  “Keep going brother,” grunted Kane as he swiped a hand between her legs. “She’s wet as fuck. Getting wetter the deeper you go.”

  And that was all I needed to hear.

  “Sweet thing,” I rasped. “You think you can do it? You think you can take all of me into your backside? Hmmm?”

  Katie didn’t answer with words, but her reply was all too clear. Because the female swayed her hips in a circular fashion, and then slowly pushed back onto my cock. Holy fuck, it was a sight to see. That big butt slid backwards slowly as her anus spread, rim gripping me tight, fuckrod disappearing into that deep brown. Holy shit, I was gonna explode in about two seconds.

  But it was too early. We wanted her stretched out and loving it, taken all the way. So Kane rubbed her pussy lips, lubing the girl up, and she relaxed more as juice dripped down those meaty thighs. Tension lessening, she was able to push back further onto my dick until we were halfway home, my fuckrod firmly stuck in that back end.

  Leaning over, I spit once again, keeping her lubricated while slowly grinding my hips.

  “Yeah, just like that sweetheart. Just like that.”

  And slowly, the girl pushed back once more until I was firmly embedded in that butthole, balls to the wall.

  “Shit, she’s wet,” rasped Kane, still rubbing between her legs. “She’s pouring into my hand now.”

  Mason dipped his head down to suckle a hard nip.

  “Her tips are like bullets,” he ground out. “Rock hard and ready to rumble.”

  Nodding, I began a slow thrust into her back end then, anal walls squeezing me tight. Shit! Katie was so dry and small, this wasn’t gonna last long. But with every sensuous stroke, the female began getting into it more, pushing back to meet me halfway

  “Unnh!” she mewled helplessly, eyes closed and squirming a bit. “More, more!”

  I let out a hoarse chuckle.

  “Oh yeah, baby likes getting buttfucked huh? You like a big cock up your ass, don’t you?”

  The brunette nodded silently, eyes squinched shut as her fingers clawed at the bedsheets, boobies heaving heavily.

  “Unnnh,” came her throaty moan again. “Oh god, yes please.”

  At that, my hands gripped her hips as the serious buttfucking began.

  “Your wish is my command, sweetheart,” was my raspy growl. “Get ready to ride.”

  Because I began pounding that anus then. Oh yeah, no mercy for the virgin. I thrust forward like a piledriver, going at it hard and heavy. But Katie didn’t complain, she didn’t cry out in agony or pain. Instead, the opposite. That big butt trembled and jiggled, welcoming me the whole way.

  “Yes!” she screamed, throwing her head back. “Yes, fuck my butt! Fuck it, fuck it!”

  And no need to say anything twice. At that moment, my dick burst, cum flooding her asshole in a giant spill, filling the sweet female’s rectum. A goopy white mess literally overflowed from between our bodies, coursing down one white thigh as she screamed.

  “Yes!” came her agonized cry. “Yes, yes!”

  And I was no better. Roaring like a madman, I thrust again and again, filling her up with virile baby batter.

  “FUCK!” came my conquering roar. “Fuck! Shit! Fuck!”

  But the thing is, we were only one third of the way done. As my dick continued to spurt, I pulled out, letting Kane take my place behind the sweet girl. And not losing a second, the big guy had his dick out and pushed right into that sweet brown hole.

  “Unnnh!” Katie cried out in shock, butt stuffed to the max again. “Oh god!”

  “That’s right,” growled Kane, already pumping like a madman. “Three for the price of one, honey, you’re taking three of us in this sweet ass tonight.”

  Katie burst then. There’s no other way to describe it. An earthquake shook that sweet female form, orgasm tearing through her limbs, body shaking like a tree in a storm.

  “Oh!” she screamed. “Mason! Kane! Tyler! Oh!”

  And as Kane shot his load deep into her ass, he too roared mightily before withdrawing on the next stroke.

  “Shit baby girl,” he panted. “I’d give anything to stay longer, but all’s fair in love and war.”

  And in a flash, Tyler was there, massive form looming behind the sweet female.

  “Aw fuck yeah,” my buddy groaned, worming his dick into that spasming anus. “I love taking a girl as she’s orgasming, it’s hard to ride a filly who’s already going buck wild.”

  Because it was difficult for him to get in, for sure. Katie was in the throes of a massive explosion, both holes winking and blinking madly, shudders running along her spine. But Mason is a master and knows exactly how to thread a needle. Because gripping those thick hips, he held her still while insistently pushing that massive fuckrod into her dark star.

  “Ohhhhh!” Katie screamed this time. “Oh god, I’m so fucked!”

  “That you are, sweet thing,” I rumbled, leaning forwards to drop a kiss onto her glistening back. “That you are, buttfucked by three men.”

  And with that, Mason unleashed the big one. If before Katie was already overfull, then now it was like Niagara Falls bursting into her ass. Gloo
py sperm literally began gushing down her thighs now, there was so much hot jizz everywhere.

  “Fuck,” grunted Mason. “I can feel their loads slopping around inside you, it’s so fucking hot.”

  The girl merely buried her face in the mattress once more, hands gripping the sheets as a tidal wave overtook that form.

  “Oh god,” came her muffled cry. “Oh god, oh god!”

  And finally, it was over. The three of us ejaculated inside that tight, private spot, her anus milking us to heaven. Tyler slid back, groaning under his breath as his cock reappeared from that white ass. All of our fuckpoles gleamed with a mixture of ass sweat and virile sperm.

  “Fuck,” was all he managed before dropping one last kiss on her anus. “Fuck, fuck, fuck, that was good.”

  We expected Katie to fall down flat right then and there. Because what woman wouldn’t? She’d just had her ass cherry taken by three men, hard, hot and heavy. We were probably going to have to call an ambulance and get her wheeled out on a stretcher.

  But never underestimate a sweet, horny virgin. Because panting, the girl looked over a slim shoulder at us, big brown eyes wide yet still hungry.

  “Put it in my mouth boys?” she mewled, opening that pink pout so that it was a perfect circle, temptation to the nth degree. “Put it in here, and let me taste?”

  I growled then, dick jumping to life once more. Because Katie’s perfect. Two seconds after getting her butt dicked for the first time, she wanted to taste the remains. She wanted to sample our cocks when they had the distinct tang of female ass on them. And I groaned, pointing my fuckrod at that perfect pout.

  “Sure thing, sweetheart,” was my raspy grunt. “If you’re into it, then we’re into it.”

  And fuck, but the feel of those velvety lips on my pole was enough to shoot me to the moon and back. Because Katie’s the answer to our dreams, a mass of contradictions, intriguing and innocent, yet devilishly wild. But will we ever get enough? Right now, this is just a weekend fling … but what about owning this female long-term?

  CHAPTER ELEVEN

  Katie

  Squirming in my office chair, I couldn’t believe what had happened at Wayland Manor. Not only had I lost my virginity, but now Mason, Kane and Tyler had also popped my anal cherry. It was so wrong, and yet the dumb smile wouldn’t leave my face.

  Because I let three alpha billionaires own my back hole on a nineteenth century bed at a tourist attraction. We went at it like wild animals, screaming and crying, uncaring of who was outside. It’s a miracle they didn’t call the cops from all the heavy pounding and breathless gasps.

  But it’s weird because I feel no guilt over what happened. I should, I know. We defiled a historic place, treating the antique furniture like it was Ikea. But that aside, I feel really good. Floating on a cloud even, like I can’t get enough. Because this is more than some hot sex, and then sayonara. Mason, Tyler and Kane surprised me by asking me questions about myself during the trip, really curious about my life. The billionaires wanted to know what makes me tick, what makes me glow, and most of all, what makes me scream with pleasure.

  Suddenly, a voice cut into my daydream.

  “Where were you earlier today Katie? You seem a bit flushed,” Sally asked with concern written all over her face. Sally’s a dinosaur at the magazine, one of those people who’ll never be fired because she’s a fixture around the place. But at the same time, I liked her. I liked the hopelessly old-fashioned pearls in a place that was supposed to represent the cutting edge of fashion. I liked her slightly messy hair, if only because my own curls was always a little mussed too.

  “I’m fine, just a little warm,” was my blushing reply. I tried to look normal, but it was impossible. “I’m fine,” I said, ducking my head again, even fanning my cheeks a little. “Thanks.”

  Sally clucked like a matronly hen.

  “You look a little peaked,” she said kindly. “Here, take my water,” she said, placing a plastic cup of ice cold liquid before me. “Just in case you’re getting sick.”

  And gratefully, I drank as Sally moved off down the hall. Get with it! warned the voice in my head. You can’t be acting weird at the office. This is work, where they pay you to be productive.

  Of course they do, but at the same time, I couldn’t stop my train of thought. Because what would the ladies’ faces look like if I told them I’d just had butt sex with three hot alphas? That I’d let three men spurt their cream into me, one right after another, filling me up all the way?

  They probably wouldn’t believe it, that’s what.

  Quiet, capable Katie, having anal sex?

  With three men?

  Yeah, right.

  But it was true. And wiggling my ass slightly, I wondered if their sperm was leaking out of my back end right now. There was so much of it after all. Maybe a bathroom break was necessary to make sure it didn’t seep through my panties and leave a tell-tale wet spot on my skirt.

  “Heading to the bathroom Laney, I’ll be back,” I called out to my co-worker in the next cube. For some reason, the need to talk out loud was overwhelming, but Laney didn’t even look in my direction, head buried in something or other.

  “Okay,” was her mumbled reply.

  Getting up awkwardly, I headed for the restroom. Oof, my anus ached a bit, my gait a little unsteady. But before even getting half the way there, my snotty co-worker Mary, a senior editor, accosted me. Stumbling, I almost ran into her before coming to an abrupt halt.

  Because I’ve never liked Mary, and she’s never liked me. The woman is a blonde trust fund baby who looks like a Barbie doll on steroids, with boobs out to there, all plastic. Most times, she didn’t pay attention to me, I was below her level. But there were times when those viper eyes turned my way, and I shivered at the memory.

  “Hi,” I said tentatively, unsure how to handle the interaction. “How are you?”

  An uneasy feeling knotted my gut. What did the woman want?

  Mary glared at me suspiciously, blue eyes like hard cubes of ice.

  “Well aren’t you chipper today. Did Jake, your long-distance boyfriend finally come back into town?”

  The woman batted fake lashes and put on a Joker-like smile that showed perfect white teeth. So that’s what this was about. She knew Jake was a lie and had decided to call me out on it. Why? Why now of all times? What good was that going to do?

  And just like in high school, suddenly, we had an audience. People peered over cubicle walls, putting calls on hold to eavesdrop on our conversation. Eavesdrop wasn’t even the right word. They were watching overtly, whispering behind lifted hands.

  My bravado left me just as suddenly as it had appeared. Did they all know? Maybe everyone knew about Jake being fake. But it was fine. It was all fine because I had three men now. Holding my head high, my voice rang clear and true.

  “Jake and I broke up last week,” I stated matter of factly. “I’m seeing someone new now.” People rolled their eyes discreetly, like I was lying all over again.

  And Mary laughed a high-pitched hyena laugh.

  “Is your new guy long distance too?” she thrummed throatily. “Let me guess, this one works in Borneo or somewhere so far away that the only time you guys see each other is over Skype right? This is a Skype relationship?” she sneered.

  My fingers itched to slap that witchy grin from her face.

  “Actually, if you must know, we just started dating,” I replied stiffly. “We met this weekend at my best friend’s wedding.”

  If Mary rolled her eyes any harder they probably would roll right out of her head and out the door. Her laugh this time was laced with malice and venom as she eyed me up and down before speaking.

  “Seriously, Katie,” she said condescendingly. “You should just stop telling lies. Just stop. This isn’t seventh grade. Everyone knows that Jake was a figment of your imagination. Everyone in the office feels sorry for you but doesn’t want to call you out. So just stop with this boyfriend shit, okay?”

>   Was that true?

  Did everyone know?

  But the thing is, there was truth to my words this time.

  But before I could respond, Mary’s words came again.

  “Now maybe you’ll stop with all your ridiculous lies. No one would ever be interested in a fat girl like you. Please. We work at a women’s magazine. We know what men want, and it’s definitely not you.”

  She stood there preening like a peacock, venom dripping from her lips. I wanted to shoot back with a sharp retort, act smart and sassy, and yet all I could do was stand there with my mouth open, willing the waterworks not to start.

  “But … but ….” came my stammer.

  Mary twirled a platinum lock around her fingers, already bored.

  “Please Katie,” she sighed like a lady in waiting. “Don’t waste our time, okay? You don’t belong here. You only got hired because we needed diversity, and you were the “fat” component. Haven’t you noticed? The rest of us are thin, you’re the only one who’s out of shape.”

  And I couldn’t take it anymore. Was there some kind of diversity initiative that included bodies of all types? I’ve heard of gender diversity, racial diversity, even sexual orientation as a guideline. But body shapes? Was I the magazine’s nod to curvy girls?

  It was too much. Letting out a choked cry, I ran for the bathroom, slamming the door and burrowing into a stall. And then the waterworks came like a flood. Why were some girls so cruel? Whatever happened to sisterhood? I know we’re not a perfect team, but still, this?

  Tearing big gobs of tissue from the toilet paper roll I blotted my face, make-up coming off in smudges. Oh god, oh god. Why was this happening?

  But there were no answers. After sobbing some more, I sat limply on the toilet seat. Why had I been humiliated again? Why me? I was twenty-two, and scenes like this were throwbacks to junior high. But not for me.

  Snuffling hard, I pulled down my panties with the urge to go. But a weird sticky feeling overcame me then. Oh my god, there was a string of cum connecting my puss to the thin silk, and seeing the wetness made me feel better. It was like Kane, Mason and Tyler were in the stall with me, their big forms reassuring, concrete proof of my desirability.