Anonymous Encounters(5)

By: Cassandra Dee

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.



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.

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