The Bet

I think that in everyone's life, no matter how much or little sexual experience one may have, there is always going to be that girl that you wanted so bad and never got. That girl that haunts you the rest of your life, the one that you fantasize about more than any other. You may have been good friends, or may have never even said as much as 'hello' to her – no matter the effect is the same. That fire that ignites in you that just can't ever be quenched. That girl for me was LeAnne.

We were casual friends in high school; me a bit on the dorky side and she a total babe. Blonde hair, blue eyes, perky tits – the perfect head cheerleader. She dated the coolest guys with the coolest cars; I drove my parents van. All I could do was admire her from a far and of course, fantasize about what it would be like to get in her pants.

After high school we went our separate ways, she to Tech and me to State to study law. I grew out of my dorkiness over the next few years and actually did quite well with the ladies during my college career, but I never was able to quench the desire to fuck LeAnne.

Once out of law school I moved away to practice with a large firm in a large city. The work was what I thought it would be and the pay was great but I missed my home, and after fulfilling my commitment to my firm I was able to land a job with a small firm near my home town. I had been back a few weeks when I went to the mall, and ran into the object of my fantasy.

I was out shopping for some new cloths when I wandered by one of the woman's boutiques and happened to look in the window and see her there, standing over a table folding shirt and setting up a display. I stopped dead in my tracks and gazed at her. She was still amazingly beautiful. Her long blonde hair had been cropped to her shoulders, framing her beautiful face and accenting her big blue eyes. She was wearing a tight blouse that let me see the outline of her still perky tits and her tight ass was stuffed into a pair of tight black pants. I felt my crotch stir and knew I had to talk to her.

I walked up behind her while she was working. "Excuse me ma'am, I was wondering if you could show me something in my size."

She turned, a funny smile on her face. It took her a moment to recognize me but when she did her smile turned to an open mouthed stare.

"Mike? Mike Franklin is that really you?"

"In the flesh," I said smiling at her reaction.

"Wow, what are you doing here?"

I explained my journey from college to present day and told her that I was back in the area to stay, about the firm I had joined and about the house that I had purchased in the town where we had grown up and gone to school.

"You've certainly changed," she said, taking in my physique. I'm not a body builder but I'm in good shape and the quality of woman that I had been with since my dorky days of high school had increased in dramatic fashion.

I looked her up and down and smiled slyly. "And you haven't at all. Wow, you still look awesome."

She blushed but shrugged off the compliment. She looked at the floor and scuffed her feet. When she finally looked up at me, she was again smiling. "So are you finally going to ask me out?"

"Maybe," I said coyly. "You never seemed that interested in me before."

"Well, that was then... and this is now. Now the roles seem reversed, don't they? Here you are a successful lawyer and me just a simple store clerk. Maybe you're out of my league."

Her humility was kind of touching. I had always looked at her before and figured she would go on to great things – meet a rich guy in college and be a trophy wife. The irony of that thought occurred to me then, here I was the rich guy looking for a trophy wife to call my own.

"I dunno, I don't date girls from Tech," I said jeering her.

"Oh you State boys think you are so cool, don't you?"

"Well, we have to have our standards."

We bantered back an forth for a while, tossing around all the standard jabs that graduates from the rival schools routinely tossed back and forth at each other.

"Tell you what," I said handing her my card after scribbling my cell phone number on the back. This weekend was the annual game between our alma matters and I decided that a bet was in order. "Tech wins this weekend, then you can plan the date. I'll take you out and do whatever you want. State wins and you accompany me to the welcome party my firm is putting on next weekend."

"Deal," she said tucking my card into her shirt pocket.

She had to get back to work and I needed to finish my shopping. We said our goodbyes and I left, anticipating the outcome of the next days football game even more than I usually did.

+++++

The game on Saturday went much to my liking with State kicking the crap out of Tech, winning by three touchdowns in a game that wasn't even that close. No sooner had time expired then my phone rang. It was LeAnne.

"Well, I guess you win," she said without bothering to say 'hello.'

"That I did, now you have to be my date next Saturday."

I filled her in on the details, advised her of the dress code and set a time to pick her up. I felt my cock stir in my pants – if things went right maybe by the end of the night I would get the chance to quench the fire that she had ignited in me so many years ago when she bopped around junior high in that little cheerleading skirt.

+++++

The week seemed to last forever even with all the things going on. I was trying to settle into my new job as well as my new house – my days spent unpacking law files and my evens spent hanging pictures and arranging furniture. Finally Saturday came and I awoke with a spring in my step. These lawyer sponsored parties are famous for being almost unbearably boring but I thought that tonight would be different, I would have LeAnne on my arm – and hopefully in my bed.

Late in the afternoon I showered and dressed, making sure to splash some cologne in strategic locations hoping that later my date would get the chance to appreciate my gesture. I hopped in the Benz that my firm had leased for me and headed to her place.

I rang her doorbell and could hear her heels clicking on the floor as she came to the door. It swung open and I almost fainted. Standing before me was the most gorgeous girl I had ever laid eyes on.

LeAnne was dressed immaculately. She had on a short black skirt that showed off her very well muscled and tanned legs, tight thighs and sexy calves. Her blouse was blood red and tied in the back with three bows, there was no way that she could have a bra on under a top like that. Sexy three inch 'fuck me' heels finished the outfit. Her hair was expertly styled and she wore just the right amount of make up. Her perfume smelled of flowers and had that indescribable quality that let you know it was expensive.

"Holy fucking shit," I said in a voice that I didn't recognize as my own.

She smiled back at me, satisfied that she had elicited the reaction that she was looking for. "Nice to see you too," She said. She leaned in and gave me a quick kiss, he lips barely brushing against mine before she was gone. I gathered my composure and grabbed her by the hand, leading her to my waiting car. I opened the door and she slid in.

We made small talk on the way to the party, filling each other in on our respective past week. Her perfume was making me dizzy with lust and her skirt rode up high giving me a great view of her amazing legs. Every now and then she would shift them ever so slightly, causing her skirt to move even higher. She was doing it intentionally no doubt, and I think that if the ride to the party had lasted any longer it would have made it all the way up.

The party was what you would expect, dry and bland. A lot of 'congratulations' and 'welcomes' and hand shaking. At least having LeAnne with me made things bearable. She as the perfect companion for the evening, smiling at all the right times and laughing at my new colleagues jokes no matter how un-funny they happened to be.

Even though the party lasted far too long, I managed to have the best time that I had in a long time and told LeAnne that. She smiled and thanked me for the compliment, but suggested that we convene to a more intimate location where we could talk alone. We said our 'good-byes' and made in back to my car a short time later. I drove fast and soon we were pulling into my drive way.

Inside I poured us drinks, a good blush wine for her and straight 12 year old Scotch for myself. We made our way to my back porch and sipped out drinks as we looked out over the woods that comprised my back yard. I really like the house, it wasn't too large but it was big enough for a bachelors needs and it was private; I didn't have a neighbor in either direction for more than a mile.

LeAnne finished her drink quickly and I refilled her glass. We talked, filling each other in on all that happened in the years since our days in high school. She told me about a relationship that she had been in in college that she thought was going to end in marriage, about moving with this guy to the city before finding out what a jerk he really was and deciding that she should move home to contemplate what to do next. I told her that I was glad that she had moved back because I was really enjoying her company.

She swallowed the last of her drink and walked over to the railing, her sexy ass swaying beneath the soft cloth of her skirt. Her legs shown in the moonlight and even her back was sexy. I figured that if I was going to make a move, now was the time. I set my drink on the table and moved up behind her.

I wrapped my arms around her and kissed her neck softly, she didn't object and actually tilted her head away to give me more access to her neck. She grabbed my hands with hers and our fingers interlaced; she held them to her tight stomach as I continued to kiss her neck. Her body was pressing against mine and I could feel her ass grind against my hardening cock.

She turned to face me and looked me in the eyes. "How long have you been waiting for this?"

"All night," I replied.

"Just tonight?" She asked raising an eyebrow.

"Ok," I admitted. "Since about eight grade."

She laughed and then kissed me, softly at first but then she began to pick up in intensity. Our mouths opened and our tongues met, she was an amazing kisser. I could taste the wine on her tongue as we kissed for what seemed like ages. My hands were on her back, feeling the sensuous curves of her body. Now and again I would slip on of my hands down to caress her perfect ass, but I didn't want to come on too strong and never let my hand linger longer than I thought was gentlemanly. When our kiss was done I let go of her and stepped away. My lust was rising and I didn't want to lose control, didn't want to blow this chance that I had waited so long for.

She looked up at me and licked her lips and in that instant I knew two things – one was that I was going to get to fuck her tonight and two that I could drop the gentleman act. She turned putting her back to me and reached behind her, grabbing for the ties that kept her shirt in place and undoing them. Her shirt was hanging precariously from her and I moved in behind her.

I put my hands on her stomach and found the hem of her blouse. My hands moved inside it and up over her taunt stomach muscles, up until I found her firm breasts. I've been with woman with bigger breasts but never with one who's were as firm. LeAnne's were a very firm B and if I hadn't watched them grow on her during out prep days I would have made the assumption that they were fake. Her nipples were rock hard and I squeezed them in each hand. My mouth found her neck again and I began to kiss her there again. My hands continued to rub her breasts, pushing them together and letting them fall back into my palms. Her breathing increased and I could tell that she was into all that I was doing.

One of her hands reached up and she ran her fingers through my hair, holding my mouth onto the soft skin of her shoulder and neck. Her other hand reached back lower and found my cock. She gave it a squeeze through the material of my pants and I grew even harder. She was pushing back into me and I could feel her ass pressed against me in the most intimate of ways. I lifted my hands off of her breasts and pulled her shirt totally free. It fell onto the deck in a pool of red and now her breasts were completely unencumbered. I grabbed her shoulder and turned her to face me.

I bent my head down and took one of her breasts into my mouth, sucking on her passionately. I pulled on her nipple with my mouth, pulling as much of her soft flesh into my mouth as I could. Her hands moved to my belt and soon she had my pants undone. Her hand was inside my shorts now and she was stroking my cock in her soft hands, coaxing me to full arousal.

My hands moved down her back to her ass and I took a cheek in each hand and squeezed. This girl kept herself in great shape and I was discovering that her body was even better than it had been in out youth, which was just blowing my mind. I pulled at the material of her skirt, hiking it up around her waste. I was now feeling her bare ass, squeezing hard as I continued to suck on her tits.

She pulled her hands from my pants and unbuttoned my shirt, pulling it off of me and dropping it on the deck with her blouse. I kicked off my shoes and almost lost my balance. She pushed my pants down to my ankles and I stepped out of them. We were standing on my back porch, naked save for my boxers and her skirt. I could feel the cool night air on my skin and was thankful for it; otherwise I might have burned up with the heat we were generating between us.

Without warning LeAnne dropped to her knees before me and tugged my shorts down, exposing my cock standing at full attention. Instantly I was in her mouth, feeling the wet warmth of her engulfing me fully. She was very good at giving head; the joke with the boys that she had dated in high school was that she could suck a backhoe through a coffee straw turned out to be no joke.

She was bobbing up and down on my member, sucking with varying pressure. One of her hands was softly massaging my balls, adding to the pleasure. She gave a very wet blowjob and each thrust into her mouth was accompanied by that great 'slurping' noise that only comes when a girl is really enjoying herself. She sucked me at length, giving me amazing pleasure with her mouth. I held the back of her head gently not influencing her motions but just steadying myself.

My orgasm was building and I told her so. I thought this would cause her to stop or at least slow down, but just the opposite occurred – she seemed to pick up speed. She was using all her tricks now, sucking me deeply and massaging the underside of my prick with her tongue. She squeezed my balls hard in her hand and I lost control, my orgasm taking over completely. My load hit the back of her throat with what felt like amazing force and I couldn't stop cuming. She didn't stop helping it along either, continuing to blow me as my orgasm continued.

When my spasms subsided she stood up and gave me that look that let me know that this hadn't been the conclusion to our evening, just the appetizer. She kissed me and I could taste my cum in her mouth, and interesting experience.

She made to unzip her skirt and I told her to leave it on. She complied and simply reached up under it and pulled down her panties. They were black and lacy, exactly what I would have expected from a girl of her proclivities. I pulled her over to the deck table and helped her up on it. I pushed her skirt up and out of the way and pulled a chair up close.

I sat in the chair and was staring up her legs to her shaved little snatch. I started at her ankles, kissing their perfect smallness. My mouth moved over her muscular calves and up to her thighs. How many times had I imagined her spreading her thighs for me in just this very fashion, probably thousands? My attention lingered on her perfect thighs; I kissed them and ran my tongue up the inside of them, stopping just shy of reaching her pussy. I wasn't teasing her; I was simply paying homage to the most amazing pair of legs I had ever seen.

The smell of her was awesome and in the moonlight I could see that her pussy was very wet. I slid a finger inside her and the back out. It was covered in her sweet juice and I put it in my mouth, tasting her for the first time. I put my finger back in her and began to slowly finger fuck her, observing her reaction and just playing the voyeur for the time being. I placed another finger inside her and she moved her hips to accommodate me. I knew that she was no virgin but he pussy was still very tight.

I couldn't stand it anymore and had to taste her. I pulled my chair closer to the table and put my mouth on her pussy. I began to lick her with long, soft strokes. Her hands found my hair and pulled me in closer. I stuck my tongue out as far as it would go and slid it in her hole. The taste was overwhelming and I began to lick her intensely. With my hand I spread her lips and found her clit, which was already engorged. While I licked at her hole I rubbed her clit between my fingers. The reaction that I got was the one that I had hoped to elicit and she curled up and held me even tighter as she began to moan with orgasm.

When her orgasm subsided my hand and tongue switched jobs, my fingers penetrating her and my mouth latching onto her clit. I sucked and tugged at her with my mouth and finger fucked her hard and fast with two fingers. Her legs closed around my head and she pressed into me, another orgasm closing in on her fast.

She came with a shudder, her hips bucking off of the table putting all her weight on my shoulders. Her hips moved beneath me and she was doing all the work as I held my tongue in place and let her do the things that pleased herself. I reached my free hand up and rubbed her tits, her nipples were rock hard. And speaking of rock hard, my cock was quickly becoming ready for another tour of duty.

"I want you inside me," she panted and I was all too happy to oblige her. I stood and pushed the chair away from the table. I looked down at her naked body and thought about all the times I had fantasized about doing to her what I was about to do. To this point, nothing that I could have ever imagined was as good as the real thing – I know that's not usually the way that things happen but for this one time in my life it was.

I pushed her legs up and back, opening her as wide as I could. I put my cock at the entrance to her pussy and pushed. My cock slid inside her with easy and I began to fuck her with all the intensity of the lust that I had for her. Her hands grasped my arms for support and I rammed into her again and again. For her part she fucked me back, moving her hips in rhythm and lifting off the table each time I pushed into her. Her pussy was wet and tight and just fucking amazing – I wanted to get lost in her and never find my way out.

I spent some time looking at her as I fucked her, drinking in her perfect body; her firm tits jiggling with each stroke, her flat stomach pulled taunt with effort as she held her legs up and apart. She was just absolutely amazing to look at.

I pushed her legs up and together so I could look at the back of her legs while I fucked her. Her legs were absolutely perfect, shapely and muscular, tanned and smooth to the touch. She even had sexy ankles and up to that point I didn't know that was even a possibility. I was fucking her with long, deliberate strokes trying to push every inch of my cock inside her. She was moaning with pleasure and responding to every thrust by pushing back against me.

She wrapped her arms around her legs and pulled them down to her check, opening her pussy as wide as she could for me. I responded by picking up my intensity and fucking her as hard as I could, each push resulting in a loud slapping sound of skin on skin. She began to cum and her legs shook in her embrace. She seemed to be trying to hold in her breath but the intensity overcame her and a loud cry of pleasure escaped her as she reached her peak.