I was feeling on top of the world, ready to take my prize. Kelly had been worth all the effort to get her to the edge.
It started with a bet, a simple wager and progressed from there.
Only five weeks earlier I had bet my best friend Brad $250 that I could nail Kelly before he could nail Sheila. The rules of our game were simple. We had a code we needed to keep, meaning we couldn't lie about our successes and our failures and we needed to keep each other posted on progress. Rules agreed upon included nothing forceful and the prey had to be fully conscious to win the bet.
We had until Labor Day, as of that date no nailing meant a tie. We started in June knowing that ten weeks would be enough to succeed or we would give up if it became hopeless before the end of the summer.
Kelly was different in looks from her long time friend Sheila in that she was a gorgeous blond just eighteen, tall and slender with legs you couldn't believe and a shy smile that would kill. The almost nineteen brunette Sheila was of average height with a set of perky knockers to drool about on her hourglass figure. Both girls were dream boats who had kept their virtue for marriage. There wasn't a normal stiff in town that would pass up the chance with these ladies, so our bet was a long shot with these two keeping their legs tightly closed.
Finally we agreed it was double dipping if could pop the cherry without protection. The bet was $500 for that victory.
We both clearly understood that we would have to start slowly by double dating. This was the easy as we both had taken the girls out in previous summers numerous times but harmlessly.
The Best Laid Plans.
I knew this was going to be a slow and painful process that would require great planning and full attention to detail. Knowing this, I put together a plan that I hoped would work.
Week One
Friday: We met casually at the beach with friends, where we all seamed to hang out in the warm summer months. Late that afternoon Brad and I asked our dream boats if the movies the next night were something we could double on. Friends like the idea of dates in pairs and the girls were no different both agreeing to go out with us.
Saturday, Date one was to the movies. This was simple no kissing, no moves, no nothing.
Tuesday, Date two was the same as date one, Kelly and Sheila were both home by ten.
Thursday, Date three same thing except we went for some shakes afterwards.
Week Two
Date four was at the beach on Saturday, just lying the whole day in the sun. We were four friends enjoying sand between our toes, beach balls, swimming and chat. We met again that evening walking the waterfront and having a good time. I made the first move and took Kelly casually by surprise by taking her hand into mine. We held hands cautiously for 45 seconds before I broke it off. An hour later I had my fingers entwined with hers again. Little did Kelly know this was the first step towards victory.
Brad had also gotten so far with Sheila and in fact they walked arm in arm. But my plan was devious, I wanted Kelly to be unsure of our relationship the whole time. I planned to use her insecurities to my fullest advantage. She never needed to know what was next, surprise was to be my weapon.
Week Three
And so it went, small calculated steps.
I kissed her good night after going to the movies, smiled into those puppies eyes and then didn't call or see her for five hard days.
Week Four
After five long days Kelly saw me walking and laughing with Beth at the beach at dusk. I knew she was looking so I gave Beth a long hug and a kiss. Beth was clueless to my plans or what was going on. But she didn't who care, she was a nice girl who had an undeserved reputation as a slut. In reality she wasn't, she was just different.
I called Kelly later in the week. She reluctantly agreed to go out for pizza. I had to make my move.
Saturday night we kissed in the car. I brushed her tits while kissing but never made real contact. We talked and agreed to meet on Wednesday for movies. I pushed a little further throwing attention to her shapely legs placing my hand on her leg at the movies. We kissed good night when I drove her home and agreed to meet again at the party on Friday night.
My strategy was clearly on course. I knew there was three basic ways to bring a girl to give it up. Some girls, the "bad ones" chose outright to get laid that day, but this was not how it would be. Some get caught in lust and emotions and it somehow happens, I doubted this was the way either. Then some lose a struggle with their boyfriends advances and their own emotions, they rarely see it coming before it is in them.
Every female reaches a point where she knows and accepts the fact that she is about to be royally fucked. At that point in time she willingly gives in to the inevitable, a good cunt pounding.
Kelly was a challenge. I needed to use her insecurities, emotions and naivety. She was jealous of my relationship with Beth, and believed Beth put out for me even though she didn't. I planned to use this to my advantage. She struggled with our relationship as well as her blossoming sexuality. Above all she struggled with the challenge of being caught off guard. I would use all of these weaknesses to get into her pants.
So as the Friday night developed I took baby steps designed towards breaking this philly until she would collapse for my pleasure.
Kelly was nothing short of delicious "eye candy" that night. Her flowing strawberry blond hair and creamy complexion was to die for. She wore a simple tight baby blue tee just barely exposing her midriff and a dangerously short jeans skirt revealing her beautiful legs and curvy ass. Looking at her, I knew there wasn't a man alive who wouldn't turn his head to get a second look at this marvel of nature. And any man alive would dream of the pleasures of getting into her skirt, including me.
The party at Marks house began slowly, some music and lots of chat. To my advantage Kelly became visibly annoyed with Beth's arrival. Arriving without a date and worried Beth might try to snatch me away from her was a tool to be used. Kelly was smart, very smart but naïve. Uncharacteristically Kelly started to loosen up. Someone brought a bottle of Southern Comfort and she threw back a couple of shots, and soon afterwards a third shot to show off her maturity. Wow, Kelly wanted to show she was grown up, to party hardy to gather my attention. No way could this have been planned better; alcohol weakens the intellectual senses but raises basic instincts. Breathing, heartbeat and of course reproduction are all basic.
I intended, drooling mentally, about fulfilling Kelly's basic needs. I wanted to get her cunt steaming hot and then ram my cock into her. But I would need to message her emotions. Intentionally chatting with Beth, I occasionally naughtily glanced over at Kelly. I was placing our relationship on the line trying to arouse a response from Kelly. No way would I have done this without the Southern Comfort. It worked. Another unwise hit of Southern Comfort moved things along for my advantage.
Kelly wanted me alone for herself and asked me to dance. The trap was set, she set it.
We went outside to cool off after two hot dances and continued to dance, tease and laugh in the cooler air. A slow song gave me the opportunity I needed to get close, very close. I pulled Kelly as close and tight as I could. With my knee wedged in between her legs, skin to skin, I could feel what I want from her. Pulling her tight with my hand against the small of her back I am not going to let her go until her juices started to flow.
It was perfect, her skirt rose up slightly as my leg pushed between her hot legs. That warm luscious body tightly against me on a cool summer night was electric.
After a half dozen more songs Kelly and I found our way to the boathouse. With her back against the wall I planted a deep kiss slowly spreading her innocent lips apart and teasing her tongue with unexpected in and out motions. Our tongues danced for what seamed like all to long before I led her by the hand to the far side of the boat house towards the dock.
Kelly asked "where are we going"?
"Exploring" I replied, but Kelly was innocently unaware that my exploring intentions were to be of her body.
Kelly was totally loosened up and the taste of the Southern Comfort was undeniable when kissing.
I took her to my spot where we could barely hear the music from the party, alone together under the stars. Kelly leaned, her ass against the docks edge supporting her tipsy weight, our toes in the sand as I put my arms around her lower back and wedged my knee, once again in between her beautiful warm legs. Her skirt rode up as felt the warmth of her pussy against my leg.
It was time to move forward; affectionately kissing my hand took a slow journey up her bare back under her tee shirt and unclasped her brassiere. With her shocked puppy eyes Kelly asked "how far do you get with Beth"? Perfect opportunity I thought to myself, little resistance, I will fuck her before the night is done.
"How far do you suppose?" I teased.
Sliding a hand under her loosened bra, I cupped her left tit and then began gently tweaking her nipple. We kissed again as she allowed access to her tender pearly globes.
Breaking off the kiss she asked "this far?"
Preying on her insecurities and weakened state of mind I teased again with my answer "Maybe, maybe not".
Oh? She answered unsatisfied.
