Maddie's Bet: Sex With a Stranger

MADDIE’S BET:
SEX WITH A STRANGER

by
Libby Cercasa

Copyright © 2013 Libby Cercasa
Kindle Edition

Table of Contents

Title Page

Chapter 1

Chapter 2

Chapter 3

Chapter 4

Chapter 5

Chapter 6

Chapter 7

Chapter 8

Epilogue

Dedication

Well-deserved thank yous

About the author

Chapter 1

F
irst, let me introduce myself: I’m Maddie, Madeline Sinclair, a thirty-year-old accountant. I don’t consider myself to be pretty, but I’ve been told that I’m attractive in that classic, movie-star kind of way. But to me that just means that you don’t look like you’ve been chasing parked cars and don’t have to bring your own paper bag to an orgy. My dark brown hair hangs down my back to just below my shoulder blades, in a mass of unruly curls; and every time I want to go for a shorter or straighter style all I hear is how much others pay their stylist for the same look. My face is just a basic oval shape with brown eyes, a small straight nose, with an average-sized mouth with lips that could maybe do with a little Botox. Nothing special—just the basic features. My five-foot six-inch body isn’t sculpted but is toned, and so it should be considering the hours I sweat in the gym to keep it that way. I’m really just your average girl next door.

I’ve been told that I’m dull and boring, always so sensible and predictable; or I was until tonight. So why am I here, walking down this badly lit street in a not-so-safe part of town, challenging everything that I am? Why did I make that bet with my best friend, Sherry? Because she called me a coward—that’s why! But what would I rather be… a coward or a slut?!

Truthful answer: neither. But, as they say, a bet is a bet.

Chapter 2

T
he bet: That I wouldn’t dare have sex, hot and heavy sex, with a stranger. No names. No obligations or complications. Just sex!

The prize: A week’s vacation at a day spa resort paid for by the loser.

And what do I hate more than anything else? Yes, you guessed it—losing—especially to Sherry. She gets this evil gleam in her eye, and you just know that it will cost you more than money.

So here I am, entering a biker bar. And who is this gorgeous redhead dragging me over the threshold, with my elbow in a vice-like grip? This, of course, is Sherry. Sheryl Jackson, my best friend: a thirty-year-old function coordinator. She’s a couple of inches shorter than me but towers over me with attitude. She’s the whole package—bubbly personality, self-confidence oozing out of her pores, the body and face of a goddess. If I ever decide to turn lesbian, then she’s my pin-up girl. I’ve been told that she only likes me around to make her look better, but I know it’s not true—she couldn’t possibly look better! Don’t get me wrong; I don’t mind being her plain-Jane sidekick. I’m not at all jealous of her—okay, maybe a little. We’ve been friends since my family moved in next to hers when we were both six. I’m closer to her than to my own sister. And that’s partly why we’re here. She says that as my proxy sister, it is her responsibility to make sure that my virginity doesn’t grow back and that this is the perfect solution. It’s okay for her; men drool when she passes. I have to put in hours of effort just to get a glance. And when I’m with her, I’m not so sure that it’s me they’re glancing at.

It’s been nearly two years since my last serious relationship. Serious for me, but as it turned out, not so much for him. I wasted ten months of my life on that jerk! All the signs were there, but like the lovesick fool I was, I didn’t see them. It wasn’t unusual that he traveled constantly between two cities—for business, he said. He was here so often that he moved into my apartment. More convenient than hotels, he said. What he didn’t say was that his other residence contained his wife and two kids! Why didn’t I see it? It all seems so obvious now. He only traveled on business but never had any dirty laundry, never had to buy supplies like toiletries or new clothing. They always just appeared when he returned to me.

Don’t get me wrong—the sex was great. We always did the things that apparently his wife wouldn’t. That was his excuse anyway, when I eventually found out about his double life. Sherry was always trying to sow the seeds of doubt into my brain, but the brain and body weren’t listening. Not until the day I received an anonymous letter suggesting I contact his wife. Listed was a name and address. It took me over a month to do it, but the reply confirmed it. And do you know what surprised me? She seemed to already know. She wasn’t angry with me or anything. No name-calling, just a polite letter telling me about her and the kids. I think that was worse than if she had lashed out at me. I felt used and dirty. And she said that it wasn’t the first time and probably wouldn’t be the last. Well, I had more pride than she did, so I ended it. Oh… I heard the usual: “She doesn’t understand me, only you do,” “But it’s so good between us,” “It’s you that I really love” bullshit, but I don’t share. Then came the insults about how he was sick of me anyway, had only been with me because he felt sorry for me, etcetera. Then it turned really nasty with threats and debasing comments. After I got a restraining order and changed to an unlisted phone number, the communication ceased. So for the last two years, Steve Baxter has been a fading memory, and the only sexual partner I’ve had takes two AA batteries.

Chapter 3

S
o here we are. We’ve dressed to kill, courtesy of Sherry’s extensive wardrobe. Short tight skirts, tight skimpy tops, and shoes with four inch heels. Everything I’m wearing is hers—except the thong she made me buy. Unfortunately for me, I am one size bigger than her. If my boobs don’t fall out, then my ass surely will. She even insisted on doing my hair and make-up. I look like a hooker!

We enter through the swinging, saloon-type doors and are immediately thrown into sensory overload. Loud voices, and I’m sure there’s music in there somewhere! There’s an overwhelming stench of stale bodies and beer. Thank heavens there’s a no-smoking rule or I’m sure I’d collapse from asphyxiation. The lighting is dim throughout except for a couple of low-hanging fluorescent lights towards the back.

I desperately try to keep my balance as Sherry guides me towards the bar, but these heels are a challenge. The bar is surprisingly devoid of patrons, much to my relief as I try to avoid stumbling into anyone. Everyone seems to be gathered towards the back of the room.

Sherry turns to me as we reach the bar. “Wine or beer?”

“Ugh?”

“I said wine or beer? I’m sure you’d prefer one of your usual fluffy cocktails but I doubt we’ll get one here. So what do you want, wine or beer?”

“Whatever you’re having,” I reply.

Sherry turns to the bar, her words muffled by the noise from the crowd. I timidly scan the other patrons. Leather-clad bodies are everywhere, both male and female. The dark, wood-panelled walls are covered with advertising mirrors and wooden tables and chairs are scattered across the floor. I hate to admit it, but the décor fits the place.

Sherry is soon by my side with a bottle of beer in each hand. She hands me one, then raises her own towards her cherry-red lips, flicking her hair over her shoulder before she sips her beer. “Come on,” she says as she grabs my elbow and leads me towards a table at the far side of the room. Several are empty, as the majority of the people are still congregated at the back, surrounding what appears to be a pool table. Nobody is looking our way; their eyes are fixed in the direction of the table. Money changes hands as, I assume, they place bets on the outcome of the game in progress. Must be a good game!

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