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Rated: GC · Short Story · Contest Entry · #1768481
There is nothing like a dare to help get over being dumped.
I'd been at the bar since 3. Tony arrived at 5. At 9 I was retelling my story of heartbreak for the 4th or 5th time.

“You need to get back in the saddle.”

“I'm not ready for that, I found her with another man.”  The idea of another woman hurt, I still loved her.

“I'm not talking about anything serious, just sex.” He drained his bottle, “Her?” His empty bottle tipped to the barmaid.

“Caz? I couldn't, not ready.” She saw the empty and  headed over. I watched her approach through a drunken haze. T-shirt clinging to her breasts that bounced from side to side as she walked.

“Time for another?” She leant on the bar, her cleavage held my gaze.

“Actually, I have to be going, take care of my man for me.” He got off the stool, leant close and whispered: “I dare you”. Then he was gone.

He hadn't dared me anything since high-school. If I hadn't already worked my way through 10 bottles of beer it probably wouldn't have had any effect on me.

“So what's got you lookin' so sad?” She leant down closer.

The dare felt like a burning sign in my head. My mind raced for a chat-up line but only got lyrics to Guns 'N' Roses songs. I thought I was actually going to say “Welcome to the jungle.” instead I began telling my tale of woe again.

Halfway through she grabbed me another beer and one for herself, she joined in with a few well placed tut or “Poor you.” After a while they were accompanied with an arm stroke. With every stroke “Your winning.” flashed through my mind. How I was winning was lost to my beer drenched mind.

“So that's how things ended after five years, I got the engagement ring back.” I raised my half empty bottle to my lips.

“I think you need something better than beer, follow me.” By the time I got off the bar stool she was out from behind the counter. The tight black skirt showed off her round ass and all I could see was “You Win” flashing across it in burning red letters.

She stuck her head round a door, “Someone cover the bar, I'm taking a break.” She then pushed open another door and disappeared into darkness.

I followed. The door slammed shut behind me. The bolt slid into place before the light bulb blinked into life. It was a small store room, metal kegs lined one wall, shelves the other. The far wall was bare bricks, she led me to it.

“This will help cheer you up.” She stripped the clinging top from her flesh. Ripe, impossibly round breasts bounced out. My hands went to them, I lifted one to my lowered mouth while my thumb rubbed the hard nub of the other.

I licked and sucked at her hot breast, while her hands freed me from my jeans. With the amount of alcohol in my blood I didn't think I would be able to perform until her hand closed around my hard member.

Half my mind screamed at me to stop, when I'd woken up I was engaged to the only woman I had slept with for over 5 years. The other half of my mind screamed about the dare. She gave me one long stroke and it was obvious which won.

She hitched up her skirt with one hand and pulled me towards her with the other. I felt silk graze against me as I slipped past the pushed aside panties. Her warmth surrounded me. Moving my lips up from her breast I surged forwards pushing her up the wall. Her legs wrapped round me as I delved deeper.

My teeth pressed against her neck as I pushed into her again and again. With each push I heard “Win!” Her hands gripped my shoulders as I thrust her into the rough bricks making her call out. I drove harder and faster, I didn't see the face of my ex-fiancĂ©e, or the face of her lover. With my eyes squeezed shut all I saw was me winning the dare.

Her skin burned against me, the salty taste of her sweat filled my mouth. Her heavy breathing became erratic in my ear. My teeth grazed along her smooth skin. Her pulse throbbed beneath my lips.

My release was sudden, the approach hidden by my drunkenness. It was powerful, forcing me to grip her thighs tightly as I erupted inside hot throbbing flesh.

I stumbled backwards as I pulled out of her almost dropping her on the hard ground.

She smoothed down her skirt, “You go home, I have a few things to do.” I wrangled myself back into my jeans before leaving.

I picked up my half full bottle and gulped it down. It took me a while to realise why she had stayed in the store room. I should have cared, but I'd had a rough day, I deserved to be selfish. As I slammed the empty bottle on the counter all I could think about was that I won the dare.

As I left the bar and walked into the night I started singing Paradise City.


Word Count: 869
Written For: April 16th 2011 "The Weekly Quickie Contest
Prompt:
The Dare 
What happens when friends dare each other to seduce a pop star, a famous actor, or even the office heartthrob/hottest woman. The story must be a one time event or one night stand.
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