The Bet

Here's another story for you guys that's been bouncing around inside my head for a while. Hope you enjoy. All characters are over the age of eighteen.

Hi, my names Richard Williams, Rich to my friends. I live in southern California with my mom Stacy. My dad died when I was too young to remember. The accident that killed my dad, while tragic, was made less so by the size of the settlement his company paid my mom. Because of this, she never had to work again, and we also got to live in a very nice neighborhood. I had a pretty normal childhood. Everything went along pretty much par for the course until I turned twelve. That's when Steven Daniels and his family moved in down the street. The first day of school that year I saw him reading an issue of The Amazing Spider-Man and we bonded instantly. We were both uber dorks and still are to this day. We also played sports and got into trouble like all teenagers do, but we were pretty good kids all things considered.

So anyway, I'm sitting in my room right now, it's about two in the morning and I really can't believe what I've just seen. It boggles my mind. The funny thing is that I'm partly responsible for what happened. Yes I'm going to explain what happened, but first you'll need some details. As I said, I live with my mom Stacy. She's thirty-seven years old, with shoulder length red hair and still turns heads when she enters a room. She's about 5'6 and 125 lbs. Not overly blessed in the chest but respectable. Even though she has red hair there's not a freckle to be found, and thanks to the rigorous workouts she puts herself through, she's built like you wouldn't believe. Now remember my friend Steven? He absolutely loves my mom. He told me the first time he saw her he fell in love. Most of the time I just laughed it off because I'd also heard a couple of my friends talk about my mom that way. It was nothing new.

The summer after me and Steven turned eighteen we were playing basketball and talking trash like we always did. We started calling each other bitches and then saying that the other couldn't get any pussy. Now, neither Steven nor I did very well in the chick category but we'd been laid a few times during high school. Anyway, the trash talk got more and more heated and it ended up with Steven saying he could score with any chick I knew. After he made a few jump shots on me I said he was full of shit, so he bet me a thousand dollars he could. Now I don't know whether it was the anger over losing or what that made me bet him, but I could really use the extra cash. The only thing was, I really didn't know any girls that I could ironclad swear Steven couldn't score with. Then it hit me. I don't know why those particular neurons fired that day, or why the hell I even considered it, but I opened my big mouth.

"Hey man, I know a girl who you've liked forever you wouldn't stand a chance with." I teased him.

"Shit, just say the name and she's all mine." Steven replied.

"Stacy." I said calmly.

"Stacy who?" Steven asked with a funny look on his face.

"Stacy Williams, dumbass, also known as my mom." I laughed.

At this point I fully expected Steven to just laugh it off and curse me in defeat but the son of a bitch did the last thing I thought he would, he called my bluff.

"Alright man, by next weekend I'm gonna be your new daddy, and you're ass is gonna owe me ten Benjamins." Steven said cockily.

Knowing that I had a lock on winning this little bet I looked Steven in the eyes and shook his hand. He told me that I couldn't do anything to sabotage him or the bet was off. Also, I had to do what he said while he was around my mom. I told him that I wouldn't do anything unfair; besides, I knew full well he didn't stand a chance with my mom. I told Steven that I would need proof of the act. A picture or video, his word would not be enough. After talking it over while we cooled down Steven said that he'd start tomorrow (Saturday). I just laughed and told him I'd see him then. After that I walked home.

(Saturday)

The next morning I was awoken by the sound of people talking loudly. After clearing the cobwebs I realized that the sound was coming from downstairs. I slowly crept down the stairs and peeked into the living room. My mom was sitting on the couch watching T.V. and Steven was sitting right next to her. They were both laughing at what was on the television and carrying on like two morons. I laughed and thought to myself that Steven doesn't waste any time. Thinking nothing of it I walked back upstairs and got into the shower. As I rinsed I wondered how Steven was going to go about trying to sleep with my mom. He was always pretty flirty with her and I once heard mom talking to Steven's mom about how cute he was, but to actually make a move on her was something I couldn't fathom. When I was finished with my shower I walked back downstairs to find Steven had already gone.

"Hey mom, anything I miss?" I asked.

"Nothing at all sweetie, it's about time you woke up though. You're gonna waste the whole day." She said.

I thought it was kind of strange for her not to mention that Steven had come over but what the hell, he was over all the time, nothing strange about that. I grabbed a quick breakfast and then got hard at work wasting the rest of my Saturday. About three o'clock mom left for her usual run so I took the time to pop in a movie. Mom was usually gone a couple hours so I had some time to kill before dinner. About an hour and a half later I heard my mom laughing. I got up quickly and looked out the peep hole on our front door. Mom was standing on the front steps with Steven. They were both covered in sweat, but Steven looked like he was going to pass out.

"That son of a bitch." I laughed.

Steven had gone on one of my mom's runs. Now my mom exercises like a machine and I know Steven's not in as good as shape as she is so it really must've taken it out of him. I looked on as they chatted. Mom laughed at what Steven was saying and she even twirled her hair around her finger. It was nothing new I thought, she'd known Steven since we were kids. Steven took a drink from a bottle of water and then offered my mom some. I chuckled knowing that she would refuse. She's kind of a germafobe and won't even drink after me. As I watched, mom took the bottle from Steven and slowly brought it to her lips. She smiled and took three or four big gulps before handing it back to my friend. Steven continued to talk as mom wiped her mouth with the back of her hand. I couldn't believe it. Before I had time to contemplate what I'd seen mom turned toward the house so I bolted for the couch.

"Hey, how was your run?" I asked as mom came through the living room.

"Same old same old." She said walking upstairs.

That was the second time that she'd neglected to mention to me that she'd seen Steven. The logical side of my brain knew there was no way Steven was making any headway in our bet. The paranoid side however, was starting to wonder. Never the less, I would have to keep a closer eye on my mom than I thought.

Later that night I noticed that even though it was about seven o'clock my mom was still upstairs. She usually had dinner ready by now. When mom finally came down the stairs her attire caused me to do a double take. She was wearing a bright yellow sun dress with shoulder straps and matching high heels. Not that it was overly inappropriate or anything but it was very short. It only came down her thighs about half way. Her hair was also done up fancily on the top of her head. Like I said, nothing inappropriate, but a bit more dressed up than she usually was for dinner.

"What's the special occasion?" I asked.

"Oh nothing honey. I just felt like dressing up, that's all." She replied.

She walked into the kitchen and I began to hear pots and pans clanging. At least she was finally starting to make dinner. After about thirty minutes mom came into the living room and sat down on the couch beside me. I couldn't help but notice her legs as she sat. I've never thought of my mom in a sexual way, but I'll be the first to admit that she is a very attractive woman.

"Dinner about ready?" I asked.

"Yeah, just about. Hey, I forgot to tell you. Steven's coming over." She said nonchalantly.

"Oh really?" I asked.

"Yeah, I told him that it was fine. It's been a while since I've cooked for you two." Mom smiled.

I just rolled my eyes and marveled at Steven's persistence. Mom and I sat on the couch for a while until I heard a knock at the door. I went to get up but mom darted by me quickly.

"Hey there pretty lady." Steven said.

"Always the charmer." Mom replied.

As I watched mom wrapped her arms around Steven and gave him a tight hug. Steven glanced down at her ass and gave me a wink. As they walked to the kitchen Steven gave me a little look. I took it as him telling me to make myself scarce. Under the terms of our agreement I decided that I would stay out of the kitchen until mom called me for dinner.

After a few minutes the curiosity got the better of me so I decided to do a little spying. I crept up to the wall that separated the living room and the kitchen. I got as close as I could to the doorway that led into the kitchen. From my vantage point I could see the entire kitchen in the reflection on the patio doors. Mom was standing at the sink while Steven was sitting at the table. As mom went about her routine Steven was devouring her with his eyes. They made small talk and every once in a while Steven would comment on how nice she looked. Mom would smile brightly as she went about fixing dinner. Eventually mom got the pasta noodles off the stove and took them over to the sink to drain the water. Steven walked up behind her and looked over her shoulders.

"Man, I don't know what smells better, the food or the cook." Steven said placing his hands on my mom's shoulders.

Mom looked back over her shoulder at Steven. It was a funny look that I hadn't seen before. It didn't look like she was mad at all. It was like she didn't quite know what to say.

"Thank you...Steven." She finally said.

Steven dialed it down a bit and sat back down at the table. Mom went to the fridge to get the salad out. As she bent down Steven's eyes were glued to her ass and legs. It was hard for me to tell in the reflection but I didn't see any visible panty line. There was no way my mom was walking around the house without any underwear I thought.

A little while later mom finally called me for dinner. I sat down at the table and smiled at Steven. With me in the same room his little game wasn't going anywhere. While mom went to the stove Steven gave me a hand motion as if to say get lost. I gave him a funny look.

"Remember the rules..." He mouthed.

I knew that if I wanted to win the bet I had to not get in his way, so reluctantly I got up and grabbed my plate.

"I'm gonna eat in the living room, there's a show on that I can't miss." I said out loud.

"Rich, you better not get any food on the carpet." Mom said.

"Don't worry Ms. Stacy, I'll keep you company." Steven chimed in.

I told mom I'd be careful and then walked back to the living room. As I ate and watched T.V. I would hear the occasional laugh. Nothing was out of the ordinary until I heard my mom yelp as if she'd burned herself. I quietly reclaimed my place by the entrance to the kitchen. In the reflection I could see that my mom had spilled some of the pasta sauce down the front of her dress. Steven had reached over and used his napkin to clean my mom up a bit. To the untrained eye it looked like a simple act of kindness, but to me he was feeling up my mom. As he got lower on her chest my mom was looking intently at Steven. I half expected her to say something as his hand went into her cleavage, but she remained silent. After a few tense minutes mom brought her hand up and moved Steven's hand away.

"I think that's got it..." Mom said quietly.

Steven just smiled and went back to his pasta. Mom fanned herself with her hand for a moment or two. She must've gotten hot after cooking dinner I thought. After a few minutes I noticed that they were sitting kinda close to each other. I couldn't tell if it was mom or Steven that had slid there chair over but someone had. I stood there for about fifteen minutes while they ate.

"Man, I'm stuffed. That was awesome Ms. Stacy." Steven said.

"Thank you sweetie. It looks like you really liked it judging from how much you got on you." Mom said smiling.

I hadn't noticed but Steven had some white sauce from the pasta on the corner of his mouth. As I watched, my mom licked her finger and used it to clean Steven's mouth. Unbelievably, after she wiped his mouth she licked her finger clean. Steven didn't see her do it but I had. What in the world was she doing? Well, Steven was like a child to her anyway, so no big deal I reassured myself.

After finishing my dinner I brought the plate back into the kitchen and sat it down on the table. Mom and Steven were over by the sink washing dishes. They didn't even know I was there as they talked and laughed. I had to hand it to Steven. It was only the first day and he'd gotten further than I thought he would. I still wasn't worried though. Flirting with my mom was one thing, but actually sleeping with her was a pipe dream.

About an hour later I heard mom telling Steven goodbye. She walked over to the couch and sat down beside me.

"That was a wonderful dinner." She said.

"Yeah, pretty good." I replied.

"I'd forgotten how much I enjoy it when you and Steven are over here. Since you two have gotten older, the sleepovers and spending every waking moment together have gotten a little rarer." She said.

"Well I think you'll be seeing more of Steven." I said sarcastically.

"Why is that?" Mom asked.

Not wanting to violate the terms of the bet I played dumb before getting up to go to bed. As I laid there I wondered just what in the hell Steven had planned for tomorrow.

(Sunday)

The next morning I got out of bed only to relieve myself, after which, I had planned on more sleep. On my way back to the bed I looked out my second story window down into the back yard. I audibly groaned as I saw Steven following my mom around like a lost puppy. Sunday was the day mom would clean up around the house and mess around in her flower garden. Steven did his best to hide it but every time mom bent over his eyes were glued to her ass.

Mom motioned for Steven to help her move a pretty large planter. Steven happily grabbed one side and they moved it about twenty feet. As they sat it down mom stumbled backwards and fell flat on her ass. They both laughed loud enough for me to hear through the closed window. Steven helped mom to her feet and started to brush some grass off of her back. In a particularly daring move I thought, he began to lightly brush the debris from her backside. To my surprise, mom didn't say a word as my friend's hand slid over her backside.

After moving another planter Steven did a stupid Hulk Hogan pose I guess as a way of telling mom he was strong. Mom squeezed his bicep before giving him a look as if to say "not bad." Steven couldn't resist showing off because he then lifted the front of his shirt and flexed his abs. Mom stared for a moment before going back to her work. I watched a few more minutes until I saw Steven leave through the side gate, but not before getting a big hug from my mom. The rest of the day went by uneventfully until about seven when I got a call from Steven.

"What's up loser?" I said.

"It ain't Friday yet buddy." He laughed.

"Soon enough, what is it you want exactly?" I asked.

"Nothing much man, just tell your mom that I said she looked hot last night at dinner." Steven said.

"No way man! I ain't helping you one bit. Just come to terms with losing." I replied.

"What's the matter? You scared that I might actually score with your mom?" He teased.

"Like hell, you ain't got a chance man and you know it." I said.

"Then it won't matter if you tell your mom what I said then." He said smugly.

I was sure he didn't have a chance so I finally relented to his demands. At least this way he couldn't say I did anything to sabotage him. After hanging up the phone I walked downstairs and into the kitchen. I grabbed a bottle of water from the fridge when I heard mom ask who I was talking to on the phone.

"Steven!" I shouted.

"You two aren't going to get into any trouble are you?" She asked.

"No mom." I said as I walked into the living room where mom was laying on the couch reading.

I debated saying anything further but I figured it'd be better to get my "chore" out of the way.

"He was just telling me about the next UFC event. And he wouldn't shut up about how pretty you looked at dinner last night." I said taking a drink from my bottle of water.

"He's so sweet." Mom said as she continued to read.

"He's just sucking up." I said.

"Well regardless, if dressing up keeps getting me compliments, I might make it a habit." She smiled.

Having fulfilled my duty I just nodded and went back up to my room. She didn't seem too overly excited to hear Steven's comment I thought. Man that extra money is gonna be kickass I thought.

(Monday)

Since it was summer I was in the habit of sleeping until noon. After stumbling around for a while I made my way downstairs. I was just about to take a big drink of orange juice when I heard the front door open. I heard mom's voice first as she was telling someone to come on in.

"Don't be silly, he's probably still in bed." She said.

I heard Steven's voice so I darted for the stairs before they could see me. I stealthily got as far down the stairs as I could without being seen. I just had to know what he was up to now. He and mom were sitting at opposite ends of the couch. It looked like they'd been running again. The T.V. was on but I could still make out what they were saying pretty well.

"Don't forget to pace yourself Steven." Mom said.

"I'm just trying to keep up Ms. Stacy. If exercising can get me looking half as good as you I'd be satisfied." He said.

I rolled my eyes as he continued to pepper little comments throughout the conversation. He was certainly persistent, I thought.

"Well just don't overdo it like I sometimes do. My leg is killing me right now." Mom said rubbing her thigh.

"I might be able to help you with that. I took a massage therapy class last summer at the health club." Steven said.

He wasn't actually lying either. He really did take the class, but only because there was a girl he liked also taking the class.

"Really? I don't know Steven. I'll be alright; I'm just a little sore." Mom said.

I was glad mom seemed to be reluctant to accept Steven's offer. But he was like a dog with a bone.

"Don't be silly, I don't mind at all, you need to take care of yourself." Steven said.

"I guess you're right. Where do you want me?" Mom asked.

Steven smiled and pointed to a spot on the floor. Mom got up and laid down next to the couch. Steven's eyes lit up as my mom stretched out before him. When mom went running she wore spandex shorts and a sports bra covered by a muscle shirt. Steven took a moment to stare at mom's body laid out in front of him but he didn't waste much time. He started with mom's shoulders, slowly massaging the tense muscles. Mom turned her head away from my direction, and with the T.V. going I couldn't hear what she was saying. Steven just smiled and worked his way down her back. Once he got to her lower back Steven used his elbow to apply pressure to mom's tense muscles. The pressure caused mom to lift her head and turn it toward me again. I was not surprised to see her smiling. Who doesn't like a massage?

Steven looked at mom's ass for a few seconds and I wondered if he was going to be that daring. His common sense must've kicked in because he went to her calves next. He used both hands to cup mom's lower leg. Once he got to the bend of her leg he used his thumbs to massage the tight tendons before doing the same to mom's other leg. The son of a bitch looked around for a moment as if he was trying to decide something. Slowly he began to work his hands up above mom's knee. At first nothing seemed to be amiss, but as I continued to watch, his hands crept higher and higher. It was hard to tell from my vantage point but his hands had to be very high up my mom's leg. I was so intently watching Steven's hands that I'd forgotten about mom. I looked at her face and realized that the smile she had earlier was gone. Her eyes were clenched tight and her mouth was slightly open. Just as I was processing what was happening she raised her head and said something to Steven. I couldn't tell what it was but he smiled and then helped her up off the floor. They sat back down and continued watching T.V. After nothing happened for a while I went upstairs for about an hour. When I came back down Steven was gone. After what had happened I was curious as to what exactly mom was thinking. I had ten Benjamins riding on this bet after all.