The Bet Ch. 01

It is kind of hard to find the right place to start, but I guess one has to start somewhere. My name is Megan Williams and this is the story about how everything changed for me last Christmas break.

I suppose I should get the basic information out of the way. I am nineteen years old and currently enjoying my freshman year of college. I have a very loving if slightly inattentive family. My father is a cardiologist and my mother is an elementary school teacher. I guess you could say that I was born with a silver spoon in my mouth, but I try my best not to be a spoiled brat. My younger brother, Ian, is a senior in high school and somewhat of a prototypical jock. As far as my family situation goes, I think that I am pretty blessed.

As far as my physical traits go, I have been told by several men that I am, "one fine piece of ass." I don't like such crude terms, but I think that I am kind of cute and possesses the assets that most men desire. Being a cheerleader also helps the cliché fantasy factor quite a bit. For the record, I am five foot four and weigh one hundred and twelve pounds. I have medium length blond hair and blue eyes. I also will take a moment to point out that I am a bit of a fashion victim. If Abercrombie and Fitch sell it, I probably own it or it's on back order.

I bet you are thinking that I am a typical air head cheerleader, that is were you would be only half right. I know that there are roles in society that we fall into. I think about them all the time. I try my best to see alternative points of view and do my best to break the bonds cast upon me by the overseers of social order. Once again in the spirit of honesty, part of me likes being the perfect blond cheerleader.

Now that introductions are out of the way, let's get to the reason whey we are here. My first semester at the university was just coming to an end and I was basking in the thoughts of seeing my boyfriend, Ryan, again. Ryan and I were going through some tough times during my first semester away and I knew that a surprise visit would be the perfect remedy.

Ryan had always seemed to slack in the ambition department. He decided that taking some time off between graduation and college would be beneficial too him. I felt more that just a little disappointed when he broke the news to me. He said that working for his father at the auto dealership would give him valuable experience that would help him in business school. I knew that he would take advantage of his dad and spend most of the time getting stoned and screwing around with his slacker posse of friends. My best friend, Lisa, says that I have a terrible sentimental attachment to Ryan due to the fact that he is my first serious boyfriend and that our best moments together are long gone.

Let me take a moment to bring up my adventurous id of a best friend, Lisa. Lisa and I complete opposites. She is a painfully outspoken girl with dramatically gothic tendencies. How did two diametrically opposed people become best friends you ask? The truth is, I'm really not sure. We were assigned seats next to each other in first grade and pretty much have been inseparable ever since. Lisa also has a theory that I am afraid to experiment and try anything new. She says that it is evident in my slavish devotion to one brand name of clothes, and my refusal to move on from the pathetic excuse for a man that I gave away my virginity too.

My mother, Lynn, was instrumental in securing me an early plane ticket home while playing interference with Ryan. While I was waiting for my baggage at the airport Ryan called me on my mobile phone and I had to tell a fib and claim that I was still at school. I felt a little horny at the sound of his voice and began to develop the perfect seduction plot in my mind. I had a nice home cooked meal with my family and was happy in the fact that not much had changed in my little hometown. I enjoyed a nice hot bath and spent some time grooming myself into a clean shaven sex kitten. Ryan was very fond of a bare pussy and I didn't have time to get myself to the salon for a proper waxing session. The weather had been, according to my mother, unseasonably warm, so I picked out my shortest frayed denim miniskirt a flimsy white sweater and some sexy sandals that barely covered my tiny feet and laid them out for the next day.

The next morning I woke up feeling tremendously aroused. It took all my willpower to keep me from touching my newly shorn pussy. I sat around in a bathrobe for most of the morning and watched some cheesy talk shows while having a modest breakfast. Thoughts of sex filled my brain as I got dressed. I felt pretty bold and decided not to wear a bra or any panties. The sheer white sweater barely concealed my pert pink nipples and my miniskirt was so mini, than any slight bend would certainly expose my ass and possibly more.

My trusty blue Acura was waiting for me in the garage and I began my journey towards sexual fulfillment. I pulled out of the driveway and noticed that the sky was beginning to become grey and wind was starting to pick up. My mind must have been in a sexual haze because I didn't even pause to go inside and pick up a jacket. After a few miles I could feel the tingling in my pussy start to reach critical mass. I needed to be fucked in the worst way. It was a feeling that I had never felt quite so acutely until that day. Lisa would definitely be proud of my brazen sexual urges; she would only be disappointed that Ryan was going to benefit from them.

As I turned towards Ryan's house a noticed a familiar blue Volkswagen bug parked in the driveway. It took me a moment but I realized that it belonged to Amber Jennings; it was at that moment I felt like was going to be ill. As if on queue the front door opened up and out walked Amber and Ryan. I did my best to park a safe distance away, but close enough to confirm my worst nightmare. Amber had obvious "fuck hair" and she was wearing an oversized sweatshirt that belonged to Ryan. They stood outside near her car for a few moments before Amber sealed my fate. She moved towards him and they began making out right in front of god and the neighborhood.

The next few details are sketchy and may be slightly embellished. I swear that she began fondling his cock through his sweat pants. My mind went blank as I put the car in gear and pulled into Ryan's driveway. I leapt out of the car and slapped Amber across the face. The look on Ryan's face will stay in mind forever. I think that he even let out a tiny scream when he saw me. Amber looked like a deer caught in headlights. My hand stung from the slap that I delivered across her pudgy face. It was at that moment that I realized that I had just wasted three years of my life and that Lisa had been right the entire time. I suddenly felt embarrassed that I had even wasted the energy to slap Amber. All I could hear as I got back into my car was Ryan pleading for me to come back.

Flakes of snow started to fall against my windshield as I sped away from Ryan's house. I swerved all over the road as I reached for my cell phone on the passenger's seat. I had a moment of clarity and decided to pull into convenience store parking lot. I instinctively dialed Lisa's number as the tears ran down my cheeks and smeared my make up. I also became acutely aware that I was sans any underwear. I felt like a complete idiot. After a few rings I heard Lisa's voice answer the phone. It took her a few moments to realize that the sobbing fool on the other end of the phone was me.

"What's wrong sweetie?" She said.

"Can I come over?" I asked.

"Of course you can. What happened?" She asked.

"I caught that stupid asshole Ryan with Amber Jennings!" I blurted out.

"Ok, you really have to come over now!" Lisa said.

"Ok, I'm coming straight over." I said.

"Be careful driving. The snow is really coming down and the roads are starting to ice up, not to mention your emotional condition." Lisa said.

"I'll take it easy." I said.

My little Acura deftly cut through the snow as I slowly made my way towards Lisa's house. I couldn't see the through the snow but knew from experience that I was pulling onto the right dirt road. The whole area was rapidly becoming covered in a blanket of white. My spirits picked up when I saw massive façade of house in the distance. I was about ninety yards from the house when I felt my tires spinning in the snow. I didn't have enough momentum to make it up the hill. My car slid back a few more yards while I steered it to the side of the road. I tried to dial Lisa's house from my cell phone but there wasn't any reception in the area. I knew that I would have to get out and walk. I looked around and was happy to find one of my brothers sweatshirts nestled in the back seat. I took one look at my flimsy sandals and knew that it wasn't going to be a pleasant walk to the house.

I could barely feel my feet and the freezing wind froze my petite backside. I reached the front door and began frantically pressing the door bell. I noticed Lisa's brother Tony's face peeking at me from behind the living room curtains. I motioned for him to be a doll and come answer the door. After a few more freezing seconds Tony opened the door and gave me a sly grin.

"Where did you come from? I can't see your car in the driveway." He said.

"My car is stuck down the road. I had to hike all the way up here." I said.

"Didn't you watch the news? The weatherman said that were going to get at least eight inches of snow." Tony said.

"I think that it is pretty obvious by the way that I am dressed that I wasn't expecting snow." I said.

"Yeah, I was trying my best not to mention that. You look kind of hot by the way." Tony said.

"Don't be a smart ass." I said.

"I am totally serious." He said.

"Don't just keep her standing in the doorway, Tony!" I heard Lisa yell.

"Ok, don't start with the yelling!" Tony Said.

Lisa rushed down the staircase and offered me a friendly hug. She looked a little different from the last time that I had seen her. Her dark hair had grown just past her shoulders and her bangs were cut in a Bettie Page bob. She was wearing a low cut white shirt that showed off her large breasts and a tight pair of hip hugging jeans. Tony stood next to her for a few moments and I could see the family resemblance. Tony was tall and lanky and his dark hair was a precise mess. Tony stood there for a few more moments and I could tell that he was looking at me.

"Quit staring her down idiot! She has had a rough day." Lisa said.

"What happened?" Tony asked.

"It's none of your business dork! Go pull your friend Oliver away from the television and go outside and chop some firewood." Lisa said.

"Oliver?" I said.

"You remember Oliver Thorton, don't you? He is in the same grade with Tony and your brother Ian." Lisa said.

"Yeah I remember Oliver. Ian and him don't get along." I said.

Lisa smirked at me and then grabbed my by the hand and led me into the kitchen. She poured me a tall glass of wine and handed me a blanket to warm myself up with.

"You and Tony are alone for the holidays again?' I asked.

"Of course, I don't mind it though. I think the more time that Mom and dad spend in Europe the happier I am. They have this tradition of being in Paris during Christmas and I think that they like it better without their offspring tagging along." Lisa said.

"I don't know if I would enjoy being alone during the holidays like that." I said.

"I'm not alone. I have Tony to boss around. Forget all this holiday talk; you still need to give me the gory details about Ryan and Amber!" Lisa said

Lisa and I Sat in the kitchen and over the course of several full glasses of wine I told my embarrassing story. I could see Tony and Oliver chopping wood in the backyard and noticed that the snow was falling heavier that ever. I could tell that Lisa was happy that I had finally seen the light and decided to stay away from Ryan forever. She goaded me on for a few moments about how I would finally have to make a change in my life. I did my best to convince that I was going to start being adventurous. It was at that moment things started getting out of hand.

"I have decided that I am going stop being a killjoy and go out and have some real fun!" I said.

"This I have to see." Lisa said.

"I'm serious. I have been faithful to Ryan and have turned down many opportunities to have fun with hot guys." I said.

"I really don't think that it is in your nature to go out and screw around. You are definitely a relationship type of gal." Lisa said.

"Everyone can change. I think that I have the desire to go out and experiment, to really see what life has to offer." I said.

"I think that you need to put your money where your mouth is." Lisa said.

"You don't believe me, do you?" I said.

"I bet that you will just hang out with your family and me all Christmas break and never take advantage of your new found freedom." Lisa said.

"We have three weeks until we have to back to school. I think that I have plenty of time to meet some one." I said.

"There you go with meeting someone. You need to be in a relationship to even think about kissing a guy much less moving on to something more." Lisa said.

"What are you saying? You think that I don't have the nerve to have a one night stand? I can fuck who ever and when ever I want." I replied.

"Want to make a bet?" Lisa said.

"What kind of bet?" I asked.

"You have to have sex with anyone who really comes on to you." Lisa said.

"Anyone?" I said

"Anyone without exception" Lisa replied.

"What do I get out of it?" I asked.

"What ever you want, I will not turn down any request as long as you are truthful about it." Lisa said.

"It's a deal. I mean how many people are going to come on to me in anyway." I said.

"You might be surprised. At any rate we better shake hands on it." Lisa said.

I remember a lump gathering in my throat as Lisa stretched out her hand. It was as if time had stopped. I instinctively reached out and shook her hand. Lisa smiled at me as if I had just made a deal with the devil.

"You are going to be a total slut from now on!" Lisa said.

"I seriously doubt that many people are going to ask me to fuck them." I said.

"I think that guys will sense that you won't say no, and that will make all the difference." Lisa said.

Lisa's words hung in the air for a bit before the silence was broken by the ringing of the phone. Lisa picked it up and all it took was one glance to confirm that it was my mother calling. Lisa assured her that I was more than welcome to stay at their house until the storm blew over and that there was plenty of food. I grabbed the phone from Lisa's hand and gave my mom the condensed and edited version of what my day had been like. She told me that it was probably for the best and that I should enjoy my new sense of freedom. If she only knew about the pact I had just made.

The snow continued to pile up outside as I stared out Lisa's living room window. I heard the clanging noise of pots and pans in the kitchen as Lisa, Tony and Oliver worked at making dinner. The house was a little on the warm side so I decided to take off the bulky sweatshirt that I had pilfered from my stranded car. I still needed to ask Lisa to borrow some panties. I had several more glasses of wine during dinner and found myself nearly falling asleep on the living room couch. Oliver had decided to go upstairs and play a game on the computer while Lisa and Tony ventured down stairs to the basement to watch a horror movie on the big screen television. I clicked past some boring channels and decided to watch some music videos for a while.

I woke up about two hours later to a dark house. The light of the television was still flickering in the living room and I noticed that some one had thrown a blanket over me. I walked to the kitchen and noticed that it was just past midnight. I could see the light on in the computer room upstairs and figured that it was Oliver trying to conquer some digital kingdom. I also noticed that the lights were off in the basement except the flickering of the television and I could hear the eerie musical score of a horror movie playing in time with the lights. I decided to make my way down to the basement but I paused for a moment after I heard some muffled moans. I snuck closer to the basement to confirm what my ears had picked up.

"Fuck me!" I heard Lisa's voice gasp, followed by a distinctly male grunt.

I felt a wave of curiosity and arousal wash over me and I decide to continue my investigation. I had no idea that Oliver and Lisa were even remotely interested in each other much less fucking. I crept down the stairs until I could see the shadows of two people cast against the wall.

"Fuck me Tony!" Lisa gasped. "Fuck your sister!"

I could hardly believe the words coming out of her mouth until I peaked around the corner and noticed Tony's naked body glistening with sweat and Lisa bent over the couch pushing back against her brother.

"Be quiet Lisa. You don't want Megan to find out do you?" Tony said.

"She won't wake up, just give it to me!" Lisa gasped.

I felt disgusted for a moment but it quickly gave way to a feeling of total arousal. I could feel my naked pussy becoming wet and my nipples strained against my white sweater. Tony began to thrust forcefully and Lisa pushed back in time with his thrusts. I heard Tony gasp and watched as he pulled out of his sister's pussy and shot his hot cum all over her waiting ass.

I felt like watching for a few more moments but knew that I had to hurry upstairs. My mind was swimming with the visions of forbidden sex. I rushed towards the couch and tried to feign sleep. After a few moments I began to calm down but every time I blinked my eyes I could see Tony's hard cock slamming into Lisa's pussy. I heard two sets of footsteps coming up from the basement, one headed upstairs while the other headed in my direction.

"Wake up sleepyhead." Lisa's voice whispered.

"What time is it?" I said in my best sleepy voice.

"It is almost one in the morning. I didn't want to disturb you earlier. You looked so comfortable." She said.

"Did you put the blanket over me?" I asked.

"Yes I did. You were giving Tony and Oliver quite an eyeful." She said.

"What?" I asked.

"It looks like you were such a hurry to get to Ryan's that you forgot your panties." Lisa said.

"I am so embarrassed!" I declared.

"You have nothing to be embarrassed about honey. You have a cute little pussy." She said.

"Could this day be any worse?" I said.

"Well a new day has started and you need to get some better sleep." She said.

Lisa grabbed my hand and led me upstairs. She was wearing a tiny sleep shirt that barely covered her voluptuous ass. I almost swooned when I thought about Tony's fresh cum trickling down her ass and onto her smooth legs. When we got to her room she handed me a sheer white cami and a spare tooth brush. I was so tired that I forgot about asking for a pair of panties. After a quick session of make up removal and face washing we threw the blankets over each other and fell asleep.

The next morning I woke up and realized that I was in bed alone. I looked around for a bit and realized that it was approaching nine in the morning. Just as I was wondering where Lisa was I heard a knock on the door. Tony poked his head around the door and smiled at me.

"Where did Lisa go?" I asked

"She said that she needed to go to the grocery store and would be back after awhile." Tony said.

"Are the roads safe enough for her to go out?" I asked.

"She took the Jeep, so she should be ok." Tony said.

"How long ago did she leave?" I asked.

"About 15 minutes ago. She said to make sure that you stuck around because your car is still buried pretty deep." Tony said.