The Bet


"I heard Steven's voice earlier, what's he up to?" I asked.

"Oh nothing...he went running with me, that's all." Mom said.

"Really? He's not much into running usually." I said.

"Well, it was nice to have company." Mom said.

For the rest of the day I replayed what I'd seen in my mind. After a while I came to the conclusion that I was overreacting a bit much. Nothing had really happened after all. I couldn't even see where his hands were exactly. There was no way in hell my mom was letting my friend feel her up. With my resolve strengthened I watched a movie before falling to sleep.


I spent the majority of the day playing Xbox until I got bored. As the hours went by I was starting to wonder if Steven was going to continue his little games with my mom. About five o' clock Mom left to go to the mall. I thought about following her just in case Steven met up with her somewhere but I decided against it. I didn't think Steven would be bold enough to hit on her in public. My guess seemed correct because it wasn't long before mom was walking back into the house with several bags. I did my good deed and helped her with her stuff. Before leaving her room I asked what was for dinner.

"Oh, Steven didn't call you?" Mom replied.

"Uh...nope." I said sarcastically.

"That's strange, because he told me he was going to call you and find out what you wanted to eat tonight. He's bringing dinner, isn't that nice?" Mom smiled.

"I guess, it better not be something gross." I said.

"Don't be silly, he likes the same things you do. Now get out of here while I change for dinner." Mom said.

"Change for what? It's just Steven coming over, not someone important." I said.

"Don't be hateful, besides, I like having someone to dress up for." Mom smiled.

"Whatever." I said as I left.

I should've known better than to think that bastard was going to take a break with only three days left in our bet. I sat on the couch for about forty-five minutes until I heard a knock at the door. I quickly jumped up and ran to open it.

"Well hi there douchebag." I joked.

"You're just scared that I'm gonna win ole' buddy." Steven smiled.

I rolled my eyes and led Steven into the kitchen where he sat down several bags. I have to admit I was kinda glad he'd brought Chinese food. I was fucking starving and the egg rolls were killer. After piling my plate high I walked into the living room and plopped down in my chair. Steven came in a few minutes later and sat on the couch. He knew mom always sat on the couch so I couldn't fault his strategy. A few minutes later Steven and I turned our heads to see mom coming down the stairs. I stopped chewing for a few minutes in awe of my mom coming down the stairs in a very short black dress. Steven's eyes followed her matching heels all the way up her legs and her tight ass. I almost couldn't believe that she would wear such a dress for dinner with me and Steven.

"Well, what do you think?" Mom asked as she stepped off the last stair.

"I told you you'd look great in that dress." Steven smiled.

"Rich, Steven told me yesterday that he was at the mall and saw a dress that I would like and he was right. You have wonderful taste Steven." Mom smiled.

"It's a little much for dinner at home, don't you think?" I deadpanned.

"Well, maybe it's just a tad short I suppose..." Mom said.

"Yeah right. Ms. Stacy you look smokin'." Steven said sucking up.

Mom smiled brightly and went into the kitchen. While she was fixing her plate I gave Steven a "go to hell" look. Moments later, mom came into the living room and sat down on the couch right next to Steven.

"You know I don't like it when you boys eat in the living room." Mom said.

"We'll be real careful mom." I said.

"I suppose...Steven what are you wearing? You smell wonderful." Mom said.

"Something I got for my birthday. Do you like it?" Steven asked lifting his head.

Mom leaned over and smelled Steven's neck just a little too long for my taste.

"Ummmmmmm" Mom smiled.

The next little while went by uneventfully as we ate, although I got tired of hearing mom giggle at all of Steven's stupid ass jokes. I finally got up to put my plate in the sink.

"Honey, would you mind?" Mom asked handing me her and Steven's plates.

I glared at Steven as he smiled and handed me his plate. After dropping the plates into the sink I grabbed a bottle of water from the fridge and went back into the living room. Just as I entered the door I saw mom standing by the T.V. looking through our DVD's. Steven looked back over the couch and gave me the "hit the bricks" sign. I flipped him off before telling mom that I was stuffed and was going to surf the net.

"Are you sure sweetie?" Mom asked.

"Yeah, I'm stuffed and I've seen all those plenty of times." I said before walking up stairs.

I waited about ten minutes before I snuck back down the stairs to spy on mom and Steven. The only problem was that I couldn't see anything with them sitting on the far end of the couch. I thought for a minute then I quietly snuck out the back door. I crept around the front of the house and got right underneath the window on the side of the living room. I couldn't hear anything they were saying but I had a bird's eye view.

Everything was pretty normal for about thirty minutes. Then Steven put his arm along the back of the couch. He left it there for a few minutes but I knew what he was doing. He slowly brought his arm down until it was around my mom's shoulders. I half expected her to do something but she leaned back against Steven's arm. Several more minutes passed then mom crossed her legs and turned her hips towards Steven. Surely she was just getting comfortable but it was pissing me off. Steven turned and said something to mom that caused her to smile. Shortly thereafter she reached down and slid her shoes off. As I watched she brought her legs up and laid them across Steven's lap.

"Son of a bitch..." I whispered.

As I fought of the mosquitoes, things seemed to stabilize a bit. Nothing else happened for quite a while and just as I was about to go inside that bastard put his hand on my mom's knee. I saw mom glance down at his hand.

"Tell that fucker off mom!" I thought.

To my dismay mom didn't say or do anything. This wasn't good for my chances I thought. I mean I still had faith that I would win the bet but an important barrier had been breached. There was no way I was leaving my perch until Steven was going home. Ten tense minutes passed until Steven leaned in and started to whisper to my mom. I couldn't hear what he was saying but mom just kind of continued to watch the movie. I tried to read his lips for a minute or two but eventually gave up. Almost forgetting about his hand I glanced down and almost shit. It was now halfway up mom's thigh, right where her dress ended. I couldn't tell for sure but he looked to be squeezing her leg. Just as my brain couldn't take anymore I saw the credits start to role on the T.V.

"Thank god..." I said.

Mom got up off the couch and turned the T.V. off. She said something to Steven and he smiled before getting up off the couch. They both walked toward the front door. Just as I was about to bolt Steven hugged my mom tightly. There was nothing inappropriate about the hug until he let go. As mom turned to open the door Steven let his hand glide down over her ass. I don't know if mom knew what he did or not but she didn't say a damn word. Fearing I would be spotted I bolted around the side of the house and was back upstairs when I heard the front door close. Needless to say, I didn't get much sleep that night. I was still sure I was going to win the bet but it wasn't as much of an ironclad lock as I'd thought.


When I awoke the next morning it wasn't surprising to find the house empty. Mom usually took her morning run on Wednesday and I was almost sure that Steven would be tagging along. I walked downstairs to fix a bowl of cereal. I took my time with breakfast then I sat on the couch for a while watching T.V. Eventually I got bored and started to play some video games. I lost track of the time and when I looked up at the clock I was shocked to see it was already one o'clock. Mom never took this long on her run so I decided to call her and see what was up.

"Hey sweetie. I guess you finally woke up." Mom said as she answered her cell phone.

"Yeah mom, I'm up. Where are you?" I asked.

"Oh, I got up this morning and Steven called to ask me if I needed anything because he was going into the city. I've been meaning to pick up a bunch of little things for the house so I thought we'd make a day out of it." Mom said cheerfully.

"Oooooook. When are you gonna be back. I'm getting hungry." I said.

"I don't know, I'm having such a good time shopping it might be late. There are leftovers in the fridge. Don't make a mess and I'll see you tonight." Mom said before hanging up her phone.

That son of a bitch planned this one really well I thought. He's got my mom all alone for the whole day. He knew I was going to sleep late like always and he took advantage of my bored mother. Part of me laughed because it was such a good move on his part. The other part, however, was not too happy about them being where I couldn't spy on their activities. Eventually I came to the realization that there was nothing I could do about it now, so I might as well just relax. Besides, they're out in public, and my mom's not gonna do anything with Steven anyway I thought.

Later that night around seven, I heard mom's car pull up in the driveway. I peeked out the corner of the living room window to see what mom and Steven were doing. They were sitting in the car talking about something. Mom was smiling a lot and Steven was making a lot of gestures with his hands. They stayed in the car for about ten minutes while I watched. Nothing out of the ordinary went down so I was relieved.

Finally they got out of the car and Steven helped carry a bag up to the front steps. I quietly moved to the peep hole to continue my spying. They just stood there talking for another five minutes or so and I wondered what in the hell they could be talking about for so long. I mean, how much could they have in common? Maybe Steven was just waiting around to see if he could get another hug or something I thought. Sure enough, just as I thought about it Steven leaned in and gave mom a tight hug. Mom's back was toward the door so I could see Steven's hands sliding up and down her back. Eventually Steven's hands came to rest on mom's hips and their embrace ended. They were still very close to each other just kinda looking at each other. Mom stood on her toes and craned her neck like she was going to kiss Steven and I almost had a heart attack.

"Oh shit..." I said quietly.

Thankfully at the last second she kissed him on the cheek. I let out a sigh of relief as my heart slowed back to normal. I saw her turn for the door so I bolted up the stairs to my room. She came upstairs later and told me what a wonderful time she had with Steven. You can guess how much I wanted to hear that. Just when I thought she was done singing that bastards praises she told me that they'd made plans for tomorrow.

"Steven invited us over to his parent's house tomorrow night. His mom and dad are out of town for the week. Did you know they got a pool put in a couple months ago?" Mom asked.

"Yes mom, are you sure you want to go over there and hang out with me and Steven?" I asked doing my best to make her reconsider without violating the terms of the bet.

"I don't have anything else to do. Why? Are you embarrassed about seeing your old mom in her swimsuit?" She smiled.

"Nah mom, you know you still look good. I was just trying to save you from some boredom." I said.

Now I knew why Steven had invited us over. He knew he could get my mom to wear a bathing suit if he threw a pool party. At least I'd be tagging along though. I told mom good night and shortly after that I was in dream land.


As I rolled out of bed I couldn't help but wonder how my chances of winning the bet were holding up. I mean, nothing had happened that was catastrophic, but Steven was definitely making headway. I reassured myself that I only had to make it through tonight and tomorrow. After a quick morning shower I walked downstairs to fix something to eat. As I dug through the cabinets I heard mom humming in the living room. I peek around the corner and saw her dusting various items. She seemed exceptionally happy and I was glad to see it.

"Morning Rip Van Winkle." Mom said as she turned around.

"Good morning mom." I said.

I walked back into the kitchen and put some pop tarts into the toaster. Eventually mom made her way into the kitchen and started dusting the top of the fridge before moving on to the counters. I sat there silently stuffing my face.

"Don't forget that today we're going over to Steven's. He said he'd get something to put on the grill. It sounds like lots of fun huh?" Mom said.

"Yeah...I can't wait..." I replied.

"Do you have any swimming trunks or do we need to get you some?" Mom asked.

"I've still got some that fit I think." I said.

"I'm just glad to have an excuse to wear my new swimsuit." Mom said.

"That's nice." I said digging some crud from the corner of my eye.

"I must've tried on ten different ones before I found one that I liked. It would've taken longer if Steven hadn't been there to help me decide." Mom said as she continued to dust.

I froze for a second upon hearing what mom said.

"What?" I asked.

"Yesterday while we were in town Steven told me about the new pool. After he invited us over I stopped by the mall to pick out a new suit. The one I have is ancient. I couldn't decide which one to buy so Steven told me he'd help out." Mom said.

"Uh huh..." I said.

"I felt sorry for him having to watch me come out in so many different swimsuits. It took about an hour." Mom smiled.

I couldn't take listening to much more of Mom and Steven's adventures so I excused myself and went back to my room. After a while I smiled to myself knowing that Steven, although persistent, was running out of time. All I had to do was keep an eye on mom tonight and after midnight tomorrow I'd be stuffing my wallet with Steven's money.

I lazed around the house for a few hours until about five o'clock. Mom knocked on my door and told me to get ready because we would be leaving in a few minutes. I got into my trunks and grabbed a beach towel from my closet before walking down stairs.

"Don't forget the sun tan lotion!" I shouted to my mom.

Moments later mom came down the stairs in some blue jean shorts and an oversized t-shirt. I could slightly see the outline of her swimsuit top underneath. I figured she didn't want to walk the short distance to Steven's house in nothing but a swimsuit. We left the house and walked the hundred yards or so to Steven's house. When we got there I knocked on the front door and seconds later it opened.

"Come on in." Steven said.

Mom and I walked into the house and sat our stuff down on the kitchen table.

"Grab a drink; I'm out on the patio. I just started the food." Steven said.

We walked out the back door and I have to admit Steven's parents had a pretty nice setup. I hadn't been over since they had their backyard redone. Not only did they have a really nice pool with a diving board, but off to side of the pool was a gazebo with what looked like a hot tub.

"Is that a hot tub?" Mom asked.

"Ha! Yeah, my mom told dad that the only way he was getting a pool was if she got a hot tub to soak in." Steven said.

It was hot as hell out so I took off and made a dash towards the diving board. I dove in and spent the next half hour or so enjoying myself. Mom sat on a lawn chair for a little while talking to Steven as he cooked the food. After my next dive I noticed mom had gotten up and moved her chair closer to the pool. I looked at Steven but he was staring at my mom. I realized why when she pulled her t-shirt over her head. The bathing suit she's picked out was neon green with a blue boarder. It wasn't inappropriate or anything but it did expose a great deal of the sides of her breasts. Steven wasn't worried about the food at all. A few seconds later mom pulled her shorts down and laid them to the side of her chair. The bottoms matched the top and I was relieved that she hadn't picked out anything with a thong or something. The bottoms were held together on the sides by two strings tied in a simple knot.

"Well?" Mom said glancing in my directions.

"You look great mom." I said.

"Smokin." Steven said.

"You boys are too sweet." Mom said before lying down on the lawn chair.

I glanced at Steven and he just gave me some stupid smirk. Eventually Steven jumped into the pool and before long we were doing different tricks off the diving board. Like all guys we were always very competitive with each other. If one of us did a trick the other had to one up him. In between tending to the food Steven did a reverse flip off the diving board. So I of course did the same trick but with a running start.

"You two better be careful." Mom said as she lay in the sun.

Steven knew he had to do something more daring than my trick so he was gonna do a dive with a half twist done at the top of his jump. I've seen him do the trick a couple times and it is impressive. It looks like something you'd see during the Olympics. This time however, things didn't go as well as he'd planned. He misjudged his distance and when he came down his foot hit the diving board. When he surfaced you could see on his face that he was hurt but he did his best to look macho.

"Are you alright?!" Mom asked as she jumped up off the lawn chair.

"Yeah...I'm fine..." Steven winced.

"Rich, get the food off the grill before it burns." Mom said.

I got out of the pool and went over to the grill. As I took the food off I saw mom helping Steven out of the pool. Mom put Steven's arm around her shoulder and helped him into the house. I brought the stuff inside and sat down at the table.

"It's alright, nothing's broken. Just a little sore." Steven said.

"I told you to be careful." Mom said.

"He's fine mom, I'm starving, let's eat." I said.

Mom fixed us some plates of barbecue and we all sat there eating for a while. We were having a really good time and for a while I forgot all about the stupid bet. After I finished gorging myself I grabbed a bottle of water and walked back outside. Mom came out with a wine cooler that I guessed she'd found in the fridge.

"I'm not leaving until I try out that hot tub." Mom smiled.

"Go right ahead." I said.

I watched as mom got into the hot tub and pressed the on button. She giggled as the jets of water turned the tub into a torrent of hot bubbly water. I stared for a while as I sipped my water. It was a beautiful day and I thought about getting back into the pool.

"I think I'm gonna join your mom." Steven said interrupting my thoughts.

"Uh my guest. Just remember that tomorrow you're gonna owe me a bit of cash." I smiled.

"Just make yourself scarce so I can work my magic." Steven said.

"I'll stay in pool, don't worry though, I'll let you make some of your money back cleaning my room and shit." I said slapping Steven on his shoulder.

Steven laughed and limped over to the hot tub. The noise from the hot tub made it impossible to hear what mom and Steven were saying. As I paddled around the pool I noticed that Steven would inch closer and closer to my mom. For the first thirty minutes or so I didn't see any reason to do anything at all. After all, they were just talking. Moments later I saw mom laughing and it looked like she was telling Steven to quit it. I couldn't see were his hands were under the water so I assumed he was tickling mom's feet or something. I let the fun and games continue for a few minutes before I decided to put a little damper on Steven's plans. I crawled out of the pool and went over to the diving board.

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byTheStinger© 31 comments/ 556527 views/ 490 favorites

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