Maddie's Bet: Sex With a Stranger

by Libby Cercasa

  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

  First, 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

  The 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

  So 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!

  A few minut
es later a loud cheer erupts from them and a scantily-clad female pushes through the crowd, adjusting her tube top and the hem of her skimpy skirt. She walks in our direction and as she passes us, she winks, wipes her mouth with the back her hand, and says, “Your turn, girls.” A look of confusion crosses my face as I turn to look at Sherry.

  “Well, well, well,” she says, “looks like we’ve come to the right place.”

  I continue to look at her in confusion. “Oh, come on. Don’t tell me you can’t guess what she was doing!” I continue to stare. “For fuck’s sake, Maddie, she was giving someone head!” My mouth forms a shocked “O.” “Shut your mouth before they think you’re auditioning for the next act, will you!” says Sherry.

  “No way!” I say. Just then the crowd around the pool table starts to disperse. Three men walk in our direction, adjusting the front of their jeans, and take the table next to ours.

  “Didn’t think she could do it,” says one. “Jeannie can take anything,” answers another, “got a mouth like a Hoover, that one.” “Deep as the Grand Canyon too,” says the third.

  “Told you,” whispers Sherry.

  “We need to get out of here,” I say, grabbing for my clutch bag.

  “Oh no you don’t,” replies Sherry as she moves my bag out of my reach. “You might just get an education.”

  “As if!” I reply.

  I really don’t know why we’re whispering. The noise in the bar is almost deafening.

  Then I see him. The crowd parts and through them steps every girl’s fantasy. Boots, tight leather pants, tight t-shirt and leather vest, all black. Oh boy, his face! An angel in male form.

  “Pick your jaw up off the ground will you, he’s coming this way!” Sherry whispers. I try to snap myself out of my trance and look away, but I can’t.

  “Ouch!” I yelp as I feel a pinch on my leg. I turn, scowling, to Sherry. “What did you do that for?”

  “I know the bet is to get you laid, but not in the first ten minutes. I want to have a little fun first.” The man walks between us and the next table, and I swear I feel a hand run lightly across the back of my ass. I hear a chair scrape backwards. “Don’t look now, but he’s sitting at the next table facing us,” whispers Sherry. She doesn’t have to tell me. I can feel his eyes boring into my back.

  I see a waitress approach his table, and someone ordered beers all round. I know it was him. That voice is liquid velvet—it can only be him—it fits the body to perfection.

  “I’m going to get some drinks,” says Sherry.

  “I’m still drinking this,” I reply, indicating my beer.

  “Well, drink up. Dutch courage and all.”

  “I don’t need Dutch courage!” I say, but I’m talking to myself. Sherry has already left the table. She’s left me alone in a bar full of leather-clad testosterone. Great, just great!

  I hear a chair scape backwards again, but this time it’s much closer. Closer, as in at our table. Oh god, Sherry, hurry up. I turn my head briefly towards the bar and see Sherry flirting with a Jon Bon Jovi lookalike.

  “I think she’s busy,” the velvet voice says. Just hearing that voice, I can feel my nipples tighten and a dampening start in my panties. “Hopefully Donga will keep her busy for a while.”

  “D-donga?” I stutter like a prepubescent schoolgirl. I can’t look at him; I know that if I do I’m lost.

  “The guy talking to your friend. Don’t worry, she won’t be disappointed. He’s not named that for nothing.”

  Okay—I can’t resist glancing at him—so sue me! What can I say; I’m weak! I stare at him with a blank expression and then it hits me. Oh…my…god! He’s talking about the size of the guy’s penis! I try to look casual and nonchalant, but those eyes—the deepest blue I had ever seen, the color of the deepest ocean. I’m getting lost in those eyes. What would it be like to wake up to those eyes? Come on girl, snap out of it. At least play a little hard to get, I chastise myself. Any minute now I’m going to have to roll my tongue back into my mouth.

  “She’s just getting some drinks. She’ll be back in a minute I’m sure,” I finally reply, trying my best to sound casual.

  “Not if Donga wants to keep his reputation, she won’t.”

  “She’s not like that—she’s sensible. She’ll be back in a minute.” Yeah, right! Who am I trying to convince, him or myself? Of course she won’t come back. If she gets even a hint of an easy quick lay she’ll forget all about me until she gets a small twinge of guilt after about her…fourth or fifth orgasm. Now what do I do? So now I have to decide how much I want an all-expenses-paid vacation. Coward or slut? Which is it going to be?

  Okay, the vacation appeals to me, as does the man. So how am I going to start? This is Sherry’s area of expertise, not mine. Small talk maybe, but I can’t imagine him engaging in a conversation about the weather. I’d flirt if I knew how, but it would probably end up looking like something in a cheap porn film. Maybe if I act a bit more like Sherry would. Goodness knows I’ve witnessed her methods too many times to count.

  I return to reality as a beer hits the table in front of me, clinking against the one that I’m holding in a death grip. While I was deep in my own thoughts, he ordered more drinks. Looking up, I see him staring at me, an amused look on his face. Looking away isn’t an option; I seem to be caught in those eyes—or “drowning” is probably a better description.

  Okay, maybe his face isn’t as angelic as I first thought. No angel would have such an amused smirk on his face. So smug, like he knows I’m going to be the next notch on his bedpost. But there’s no harm looking, is there?

  Dark hair, cut just above his shoulders; a square jaw with just a hint of stubble; lips that make you want to suck and nibble on them all day; a straight nose with a slight bump at the top; and those eyes. No visible scars or blemishes—he seems too flawless for a biker bar. He obviously works out. His tight t-shirt hides nothing. Although the vest covers his sides, there’s no doubt that his body contains not one ounce of fat. I have a sudden urge to run my fingers under the hem of his t-shirt and…

  “Like what you see?’

  Oh God—back to reality! I can feel the heat running up my face. I’m blushing like a schoolgirl. Now what would Sherry do? Okay…take a deep breath.

  Nope, I can’t do this. I’ve got to be true to myself, no matter what. Oh, bugger off, conscience! What’s the harm until Sherry can tear herself away from her fun? Flirt, come on, flirt, damn you! It can’t be that hard. A few flirty words, some sultry looks. It’s not as if you’ll see him again.

  “Yes. What about you?” OMG! Where did that come from? I do feel a little bit braver. Well, I do until his eyes start accessing everything of mine above the table.

  “What I see so far…definitely,” he says, looking directly at my boobs.

  Now he’s done it. My nipples are getting so hard I’m sure he can see them. Who can’t in this top? It’s like they are reaching for him, begging him to pinch and suck them. Sherry, I hate you!

  “There’s no hurry. You can show me the rest later.”

  Oh…my…god! I can’t do this! Where’s the mystery and romance? I just don’t have any cheap tart in me. I’ve got to get out of here!

  The look on my face must have said it all. Next thing I know his hand is covering mine and he’s trying to reassure me.

  “It’s okay. You look like you’re about to run! But don’t, please!”

  “I…I…” Great, now I’ve got a stutter!

  “I saw how frightened you looked when your friend left, so I decided to take my chance and rescue you.”

  “Rescue me? From what? Who?” I manage while nervously scanning the room.

  “All of them. If I hadn’t have come over here, you would have had any number of these men over here in an instant.”

  “Yeah, right!” I don’t believe him. It’s just another line they use to make you more reliant on the male species. Well I’ve had enough of that! From now on it’s me that I rely on. No one else
!

  “‘You don’t believe me?” Great, now he’s reading my mind! “Okay, I’ll be back in a minute.” With that, he’s rising out of his seat and walking towards the bar. I must admit—the view is good. Those leather pants look like they are hugging a perfectly formed pair of tight butt cheeks. Oh, and those thighs. Just the sort you want either side of your own, pinning you to the bed.

  Then it starts. In front of me, blocking my view, is a less appealing specimen. There’s no comparison, really, but apparently this idiot doesn’t know it. He seats himself, uninvited, and tries to talk directly to my boobs.

  “So, Sugar…your place or mine?”

  Oh please! As if! “That seat’s taken,” I tell him. Yep, like that’s going to work.

  “Didn’t look like Jake was doing so well to me. Looked like he bombed out big time!” As he says this he’s trying to play footsie under the table, bruising my toes in the process.

  “Ouch! That hurts! Do you mind?”

  “Not at all, Sugar! I don’t mind at all! In fact, I know the perfect place we can go to and I can suck them better for you.”

  Oh god! Now I’m going to be sick! Don’t get me wrong, I’m not averse to a little toe sucking, but there is no way that mine are getting anywhere near this idiot’s mouth.

  Okay, it’s time to leave. As I’m rising and trying to maintain some dignity, a hand gently applies pressure to my shoulder and keeps me seated.

  “I believe the lady said that that seat was taken, Rocky!”

  “Yes! I…” A gentle squeezing of my shoulder tells me to keep silent. It’s not hard to do. My body seems to be tingling. It’s starting where his hand is resting and quickly moving to more intimate areas.

  “By me!” This last, very short, very direct statement is said with such authority that both Rocky and I immediately look down at the table.