Anonymous Encounters (The Billionaires Club Book 5)

by Cassandra Dee

  DONNY: Great, you up to meet tonight?

  A pause.

  LIPSTICK4EVAH: Well, I’m not sure. Do you want to chat more?

  DONNY: Bout what?

  Another pause.

  LIPSTICK4EVAH: Well, this just seems so fast. I mean, you only emailed me this morning.

  DONNY: That’s what it’s like here. It’s discreet encounters baby, we’re not going to get to know each other or anything.

  LIPSTICK4EVAH: Oh I get it, totally get it. I was just wondering more about you.

  DONNY: ???

  LIPSTICK4EVAH: You know, like what you like to do for fun? Where you live?

  I sat back, grunting. This girl clearly had no idea what she was doing on-line, much less on a site like Discreet Encounters. I needed to set her straight.

  DONNY: Where I live? Shit honey, that can get you shot and killed on this site. We’re all about anonymity, baby, where I live is the last question you should be asking a dude. You do that often? The moderators haven’t warned you? Did you read the Terms of Agreement when you joined?

  A pause. Was she flustered? Embarrassed? Had I gone too far? But then the ellipses appeared again.

  LIPSTICK4EVAH: Oh I’m sorry! I just joined yesterday and yours is the only message I’ve gotten so far. I mean, I’ve gotten other messages but they were from people whose names were … well, I can’t repeat them here.

  That made me chuckle. Can’t repeat them? I wanted her to say those filthy words, to hear them float from those sweet, pouty lips. But still, she had my curiosity piqued. There was something curiously naïve, innocent and giving that drew me like a magnet.

  DONNY: So … you wanna meet tonight?

  Another pause.

  LIPSTICK4EVAH: I do, but …

  My dick twitched. What was going on? Usually a girl who ducks and covers, who plays coy and kittenish does nothing for me. Usually I’m looking for hot sluts, ones who leap on the chance to get their pussies plowed by a random stranger, some dude who was willing to do it with no questions asked, no comments, no judgement, no nothing. But somehow, my lipstick girl had charmed me. The hesitation, the naive questions about where I lived and what I liked to do were getting under my skin, pulling me in rather than turning me to ice.

  So I kept going.

  DONNY: What’s got you holding back?

  LIPSTICK4EVAH: It’s not you, it’s not.

  I frowned. Of course it wasn’t me. I don’t have a pic up, I don’t have any stats except that I’m a forty five year-old white male, athletic, living in Vegas. Could be anyone right? There’s no reason to disclose that I’m a billionaire with a hot bod and private plane at my disposal. No need to say I own a couple islands in the Seychelles, that I like to vacation in Paris and Milan, that I’ve got a closet full of designer suits. To these ladies, I’m just a finger in the crowd.

  So I waited patiently as Lipstick typed.

  LIPSTICK4EVAH: I just want to make sure that you know, you’re real.

  I almost laughed aloud at that.

  DONNY: Oh I’m real. You’ll see how real I am tonight, absolutely.

  Another pause.

  LIPSTICK4EVAH: You promise?

  Again, her innocence was charming if naïve. A promise from some random dude on the internet, who hasn’t even posted his pic? I wasn’t a wolf in sheep’s clothing, I was just a wolf, straight out. And yet the girl was willingly putting herself between my jaws, begging me to bite. All the better, I love these types of meetings the most.

  DONNY: I promise, baby girl. It’ll be good. Relax okay? Just meet me there and relax.

  Another pause.

  LIPSTICK4EVAH: Okay then. Great American Music Hall for the 10 p.m. showing right? Ticket’s at Will Call for me?

  DONNY: You got it.

  LIPSTICK4EVAH: Okay, I’ll be there. Bye now.

  And with that, the green light next to her name flickered off. I sat back, heart thumping despite the fact that my big frame looked relaxed. Usually I have no problem with these on-line dialogues. Most girls want to chat a little, they want to make sure I’m not some thirteen year-old adolescent boy causing trouble. They wanna make sure I’m not their high school math teacher, the one with the bad breath and big belly.

  So it’s understandable, and the concert ticket serves more than its obvious purpose. These tickets are expensive, even the ones in the back for people who stand. At two hundred bucks a pop, I’ve made an investment, I’ve shown that I have skin in the game. And does it really matter what I look like? After all, the females are getting a strange finger in the puss, and all that matters is that my digit is clean, big and thorough. I could be Kermit the Frog or James Bond, and it wouldn’t make a difference.

  So I stood, stretching, looking deceptively relaxed. For some reason, Lipstick was making my heart pound unnecessarily. What was the name she’d given again? Rebecca? Renee? I looked at my phone. Oh right, Rachel. I was supposed to leave the ticket in the name of Rachel Smith. Well, that’s a throw away name if I’ve ever heard one, probably just the moniker on her fake ID. But whatevs. I was looking forwards to meeting my little Rachel for a down and dirty tryst. And even if she never saw my face, it didn’t matter. Anonymous, discreet, and covert is how I operate and a certain female was gonna get fucked tonight.

  CHAPTER TWO

  Rachel

  I stepped up to Will Call.

  “Um hi, Smith?” I asked hesitantly. “Rachel Smith?”

  The cold air was chilly and I shivered in my thin jacket. But even more, I trembled because this whole thing was so nerve-wracking. I was half sure that the woman would look through her stack of tickets and come up with nothing, embarrassing me. But instead, the middle-aged hag cracked her gum loudly, before sticking out a hand.

  “Here ya go,” she said, looking bored. “Here ya go.”

  And looking down, sure enough, there was a ticket for the second tier, standing room only. People milled about around me, the crowd buzzily excited for tonight’s performance. But I was dumbstruck, all the blood draining from my body. Oh my god, was I really gonna do this? Oh my god, oh my god.

  My thoughts were cut off by the Will Call woman’s impatience.

  “Next!” she bawled loudly, already eyeing the long line behind me. “Next!”

  And with dazed steps, I moved out of the way, caught by the swell of passerby, moving with numb feet towards the door. Could this be really happening? Was I going to meet up with my unseen correspondent, this guy who called himself Donny? Why did he call himself Donny anyways? It was such a funny name, bringing to mind Donnie Wahlberg of New Kids on the Block, a former boy bander from the wrong side of Boston. Was my anonymous guy the same type of Donny? Once cute but aging now, with squinty eyes and a buzz cut? Or was he something else entirely?

  And that’s why this whole thing is so crazy. Because I’m at the Great American Music Hall after chatting on-line with a virtual stranger. And it’s not like we’ve been chatting for weeks or months. We’ve only chatted once. That’s right, once, this afternoon. Other than the initial email he sent me on Discreet Encounters, we’ve only had one on-line session, and my partner in crime was completely unforthcoming then, telling me nothing about himself despite my not-so-subtle attempts to pry.

  So what the hell are you doing? screamed the voice in my brain. Rachel Smith, what in the world are you doing? Are you crazy? He’s probably some psycho stalker, some ax murderer who specializes in luring women to their deaths, you’re insane to be here!

  And of course, the voice was right. I was insane to be here. But the thing is somehow that chat entranced me. There was a way about the man, a darkness to his tone that was devastatingly sexy, a deep, knowingness that permeated his every sentence. I can’t put my finger on it, but somehow the manner in which he parried with me, answering my questions with the subtlest replies, always guiding but never forcing, made something flare inside, something hot and sensual despite my logical brain trying to tamp it down.

  So I was here now, o
n the steps of the Great American Music Hall. Whoever said curiosity killed the cat was probably right, because I was about to get my pussy fingered by a total stranger. Holy shit. Me, boring Rachel Smith, such a dunce that I actually gave my real name without thinking twice, is signed up for a rendezvous with a total stranger. And not just any rendezvous, but one where he’s gonna touch my sweetest spot, caressing places that no man has ever touched before.

  Because I’m a virgin and yet I’m gonna let some random guy stroke my clit and push his fingers into my interior canal. I’m gonna let him feel me until I scream, until the swell breaks and I shatter. Me, Rachel Smith, who works at the school library wearing staid button-up sweaters and boring knee-length skirts. Oh my god, I really was crazy, someone take me to the insane asylum now.

  But it was too late because the crowd swept me to the front of the line, and with unseeing eyes I presented the ticket to the usher. As she scanned it, a beep sounded, and the woman didn’t even look up, already onto the next person.

  “Level two,” she mumbled. “Staircase to the right.”

  Again, I was buffeted by the crowd, pulled by the human sea in the right direction and found myself standing at tier two sooner rather than later, stunned, the good angel on my shoulder still warning me to stop. Get a hold of yourself, she admonished. Get a hold of yourself. It’s not too late to back out. You can still turn around and leave, it’s fine.

  But the thing is that the human tide had me boxed in, and besides, I didn’t want to leave. This is the craziest thing I’ve ever done in my life, and you know what? I kinda like it. I kinda like being different from my usual tame persona, the kind, dependable Rachel that everyone knows. Not that I don’t want to be kind and dependable, but I want to live a little too. I want to feel sexy and crazy, I want to let my hair down and do things that no one would dream of when they see a plump girl with curly brown hair and a shy smile.

  Besides, it was too late now. The lights were dimming and I took my place at the edge of the railing, looking out over the sea of people beneath. Tier Two wasn’t too packed, there were other folks, sure, but it’s not like we were jammed in like sardines. I shot a nervous look over my shoulder, automatically scanning the crowd for anyone who could be my mystery man.

  But there was no one. No one was even looking at me, every single person seemed to be with a date, or chatting with friends, or guzzling beer from red Solo cups.

  Stop it, the voice in my head went. He told you not to look for him. You’ll never see his face, the only thing you’ll be experiencing is touch. So don’t even look, that’s part of the deal, remember?

  Besides, it was probably better not to look because best case scenario, my Lothario was a normal, middle-aged dude, probably married, who wanted to get his rocks off while the missus was out of town. He’d put an ad up and I’d responded, and since wifey was scheduled to return to the next day, and tonight was the night. A married man? I didn’t want a part of that, so it was better not to see his face.

  Besides, the worst case scenario was so much worse. In this case, my partner was some disgusting geezer who wanted to touch pussy for fun, who liked sweet, creamy teens and wasn’t shy about putting up ads to meet one. He couldn’t get it in real life because of his zillion warts and hairs sprouting out of his chin, bent over like a gnome. Shit, if that was the case, then yeah, I was better off not looking into his eyes. That way I could at least pretend a hot alpha had come to feel my pussy, to take me to Neverland.

  Facing forwards, I fixed my eyes on the stage as the band strode out, jaw set, nerves on edge. Oh god, oh god, things were starting now and it was too late to back out. Every muscle in my body tensed, every sense on alert even as I strove to look normal, like I was another concertgoer enjoying the music.

  And just as the strains began, a deep voice sounded in my ear.

  “Relax baby girl,” it commanded. “Relax.”

  I started involuntarily, helpless already. Because this definitely wasn’t the voice of a gnome. It was dark and sexy, making me twinge unexpectedly inside, inner channel running wetly. Warm breath skated across my neck and I realized the man behind me had to be tall, over six feet at least.

  “Hi,” I said breathily. “I wasn’t sure you’d come.”

  But any small talk was cut off immediately. As the band launched into its first riff, the man behind me merely nipped my neck once lightly with his teeth, making me squeal out loud.

  “No talking,” was all he ground out in reply. “No talking.”

  And breathing hard, I nodded, sensations already on high. Of course no talking, right. We weren’t going to exchange any words, this was a completely anonymous encounter, a random stranger fingering my pussy until I came, and then dissolving into the woodwork like it’d never happened. There were no words, no faces, no names, no nothing, we were two strangers meeting in the night. So nodding my head slightly again, I forced myself to look forwards, eyes blind. Every muscle in my body was slightly tense, every nerve on edge as the big stranger moved in back of me.

  And then I felt it. His hand on the outside of my thigh, caressing, warm, hot even, the palm curiously gentle for someone so big.

  “Shit,” was all the voice said behind me. “Shit.”

  I whined slightly despite his warning that I wasn’t supposed to talk. But this wasn’t talking, this was the animal sound of a woman in heat, a female ready to be touched and fucked. Because suddenly I didn’t care. I needed this to happen, desperately wanted it, and my ass bumped against him, begging for more.

  “Horny little slut, aren’t you?” came a dark chuckle in back of me. “Horny, huh?”

  But I was still now, unable to move, because on that one bump I’d felt something hard press against my flesh and it wasn’t his belt buckle. I’d instinctively raised my butt, seeking his touch, and my ass had brushed against a fucking hard snake. I’m a virgin, but I know aroused cock when it touches me, and oh god, but that massive staff wasn’t just hard. It was pure steel, stiff enough to punch through metal, and the realization made me even hornier.

  “Please Daddy,” I cried out throatily, low so that no one could hear but us. “Please,” I begged.

  The big man chuckled behind me, moving even closer, the rustle of his jacket evident. He pulled it forwards so that it shielded us, or at least shielded my ass, and then whispered in my ear.

  “It’s coming little one, don’t worry, it’s coming.”

  And just like that, the play started again. His fingers ran up the backs of my thighs, trailing lightly, teasing my flesh, making me shiver uncontrollably. But then they stopped, and I moaned, the anticipation almost painful, gyrating my hips desperately. But I knew why he’d stopped. Because I hadn’t worn panties and my partner had just discovered that fact, lightly sampling my bare, wet flesh.

  “Little slut, aren’t you?” he rasped directly into my ear. “What little whore doesn’t wear panties? Nasty little cumbuckets, that’s who.”

  The words should have made me so angry, should have turned me off, they were so demeaning. But instead, I only wanted it more, the heat inside ramping up a million degrees because yeah, tonight I wanted to be a man’s cumbucket. I wanted to throw my inhibitions to the wind and become a receptacle for a strange male, to let him finger me everywhere, touch where he wanted, using my body until I collapsed.

  “Oh yeah Daddy,” I breathed, cunt dripping wildly. “I’m your cumbucket, only yours.”

  He grunted in back of me, that thick, hot dick brushing my ass again.

  “Not tonight, you’re not, you’re just a fingerholster tonight. But later, I promise,” he whispered into my ear again. “Later baby girl.”

  And with that the big man began his exploration once more.

  “Mmm, I like,” he ground out, low for my ears only. “I like a lot.”

  I whined slightly, wiggling my butt. Because the man was stroking my curvy rump, running his fingers over that ass before gripping the flesh and squeezing hard, making me jump. Oh
god, it felt so good as he kneaded and massaged, and I held perfectly still, letting him touch wherever he wanted, wild and wanton.

  “I’m not even there yet,” he rumbled, deep voice amused and smooth. “I haven’t even touched Wonderland yet. But we’re getting there.”

  Because slowly, oh so slowly, his fingers began to worm their way in. No, not into my vaginal channel, not yet. Instead, he put two fingers against the small of my back, pointing downwards, and began a slow slide vertically. That’s right, he pushed two digits down my back and slid right into my butt crack making my eyes fly open. Was this really happening? Was this man really reaching down deep between my ass cheeks, slightly sweaty and plump? Was he really gonna to touch my anus, that nasty, private hole?

  And oh yeah, but Donny’s not a man to hesitate. Because in one fell swoop, that huge hand was buried between my butt cheeks, the mounds of flesh squeezing him tight. And pausing for a moment, the big man enjoyed it, wiggling his fingers as heavy buttocks clamped around him.

  “I love a woman with extra curves,” he rasped into my ear. “And fuck baby, but you’ve got ‘em.”

  My entire body went hot then, pussy streaming wetly. Because oh yeah, I’m a big girl and sometimes it’s not easy. Sometimes it’s embarrassing if the space between restaurant tables is a little small, or if you have to ask for the seatbelt extender on the plane. But now, his words made me feel so wanted, so desirable and utterly female. Because I was doing something a skinny chick couldn’t. My ass is so generous, my rump so big that he could bury two fingers inside and get lost in the clamminess, the ginormous mounds eating him up.

  But Donny didn’t stop there.

  “Sorry baby girl,” he panted into my ear. “But Daddy doesn’t have time for playing with your back hole now, I gotta fuck the good stuff.”