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The Bet

Category: Mature
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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.


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.


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.


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.

“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 huh….be 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.

“Hey mom! Look!” I said as I barreled off the end of the board.

When I surfaced I heard mom telling me to be careful. My plan had worked though because her attention wasn’t on Steven any more, a fact that didn’t go unnoticed by my friend. He was glaring at me but I just smiled at continued to swim. For the next hour or so any time that Steven made any advances towards my mom I would do something to get her attention. I even faked cramps once. Eventually my game plan was foiled though. Steven got out of the hot tub to get my mom another wine cooler. On his way to the house he leaned over the side of the pool.

“Cut the shit man. You’re breaking the rules. Tell her you’re going home or the bet’s off.” he said.

Now I knew I was probably bending the rules just a bit so I wasn’t mad for him wanting me to leave. Besides, there was no way I was going to let him pull out of the bet after all this time. I told mom I was feeling tired and was gonna go home. She said she wouldn’t be much longer so I grabbed my towel and pretended to leave. About five minutes after I left I walked back into Steven’s house and took up a spying position at the window above the kitchen sink. With the blinds drawn almost shut I could see them but they couldn’t see me.

Steven and mom sat in the hot tub for a while laughing and splashing water at each other. As they were fooling around Steven made his move and slid right up beside my mom. She didn’t seem to mind even when Steven put his arm around her shoulder. They talked for a few more minutes then I saw Steven take his arm from around my mom’s neck and it disappeared from view as it sank under the water. I couldn’t hear what they were saying but mom appeared to be in mid sentence when her eyes widened. Steven just looked straight forward. Slowly mom started talking again and everything appeared to go back to normal. Mom laid her head back against the back of the hot tub and slowly her eyes closed. I waited anxiously as I watched for any sign that Steven was making any headway. They both sat in the hot tub motionless for a while and I was just beginning to relax when I looked back to my mom’s face. Neither she nor Steven had moved an inch but her mouth was now halfway open. With her head leaned back and her eyes closed it looked like…well. I’m not going to say what it looked like. I started to panic not knowing if Steven was doing something to her under the water.

“Calm down, it could just be the water jets making her do that.” I told myself.

I continued to watch for another ten minutes or so hoping that I wasn’t seeing my chances of winning the bet unravel in front of me. I kept staring at mom’s face trying to see if anything changed. Just a few seconds later I saw mom stand up in the hot tub. I prayed that Steven had gone too far and that she would tell him off or something but nothing happened. Mom got out of the hot tub and walked back to her lawn chair were she laid down on her stomach.

Steven got out of the hot tub and brought another lawn chair over right beside moms. I was just glad that now I could see what was going on without the water there to hide Steven’s actions. Mom laid there for a few minutes with Steven sitting beside her talking. Everything calmed down for a bit then Steven picked up a bottle of sun tan lotion and appeared to ask if he could rub some on my mom’s back. Mom raised her head and nodded her approval. Steven rubbed some lotion on her shoulders and upper back. He was quite brave as he applied lotion to mom’s lower back and sides. He came very close quite a few times to the exposed sides of mom’s breasts. I could see them pretty well even from the window so I knew Steven was getting an eyeful. Steven kept rubbing mom’s back and shoulders for so long that I knew damn well that the lotion was thoroughly applied. He was more massaging her than rubbing the lotion in. As I looked on I saw Steven use one hand to quickly untie the back of mom’s bikini top. He did it so fast and while one hand was still rubbing that I don’t think mom realized what had happened until it was already done. Steven didn’t give mom any chance to say anything either as he continued to massage her back. The sides of mom’s breasts were fully exposed now and I was fuming as Steven stared at my mom’s exposed flesh.

Steven continued to massage my mom’s back slowly working his way down. Once he reached the small of her back he wrapped his hands around her waist and started to slide his hands up slowly. I knew that if he kept going his hands were going to touch the sides of mom’s breasts. Mom’s arms were raised with her head lying to the side resting on her forearms. I watched in slow motion as Steven’s hands slowly glided up mom’s side. My mouth opened as Steven’s fingers glided across the sides of mom’s naked tits.

“C’mon mom….don’t let him…” I said quietly.

To my dismay mom didn’t move a muscle, even when Steven’s hands moved back down and once again his fingers slid over her breasts. He repeated those movements for a little while. I think he was testing the waters because he seemed to go lower every time. Slowly but surely his hands kept going lower until eventually his hands were sliding over mom’s hips with his thumbs clearly gliding over her butt. He kept up his massage until his hands were sliding down mom’s thighs. I wanted so much for mom to say something or do something to stop him.

“What the fuck mom?” I said.

Steven looked to be having the best time of his life. He was grinning broadly as his hands caressed my mom’s skin in places I thought he would never even get close to. Steven took a second to put some more lotion on his hands before rubbing back up mom’s thighs until he got to her ass. I guess he thought he was irresistible because he untied one side of mom’s bikini bottoms. I was about to shit when I saw mom’s hands quickly retie the knot. Steven stopped in his tracks as mom retied her top as well. I breathed a sigh of relief that the torture session was over.

Mom sat up in her chair and took a big drink of her wine cooler. She talked to Steven for a while. I thought she might tell him off but they both smiled the whole time. A few minutes later mom got up and got into the pool. She swam a bit before Steven got in as well. I watched as they swam and was beginning to think maybe I could go home. Steven splashed mom with a big wave of water which caused mom to return the favor. Before I knew it they were almost wrestling in the pool. Steven dove under water and mom turned in circles looking for him. She was laughing loud enough for me to hear her in the house. I also heard her scream when Steven came up underneath her and tossed her. They horse played like that for a little while until mom appeared to get tired. She swam to the side of the pool and rested her head and arms on the edge of the pool. Steven swam right up behind her and rested his head on her shoulder. His hands were under the water again so I didn’t know what was going on. They stayed like that for a few minutes then mom got out of the pool and dried off. As she was drying her hair out Steven got out of the pool and I cursed out loud. Even from the window I could see that he was hard as a rock. He stood beside mom with the front of his trunks bulging out while he dried off as well. Mom didn’t blatantly look but there was no way she wasn’t aware of it. She wrapped her hair in the towel and put back on her shorts and t-shirt. Just when I was about to bolt I saw Steven walk up behind her and wrap his arms around her waist. I couldn’t tell exactly how close he was but I hoped mom wasn’t letting him touch her with his erection. Mom turned her head and kissed Steven on the cheek before heading towards the house. I ran like the wind back home and was upstairs before mom got to our front door. Later she came up and asked if I had fun. I pretended that I had and told her I was gonna hit the sack. She said she was going to do the same after a quick shower.

Just before I turned the light off in my room the phone rang and I saw that it was Stephen on the caller I.D.

“One more day and you owe me big man.” I said immediately.

“That’s all I’ll need. Did you see earlier? I had your mom eating out of my hand.” Steven said arrogantly.

“Whatever man. Hugs and massages aren’t what we were betting on. You got a long way to go.” I replied.

“It’s cool man. Look, tomorrow night around seven, I need you to tell your mom that you’re going to a party or something. I’ll wait a while then go over and seal the deal.” Steven said.

“Uh huh…” I said.

I wasn’t sure about leaving them alone but I knew that I had to do what Steven said. It was his last chance and I knew I could just sneak back later and spy on them anyway.

“Cool, just remember that you better have proof or it’s gonna be time to pay up sucka.” I laughed.

“I got a new cell phone just for tomorrow…” Steven said before hanging up.

I laid in bed for a while thinking about what happened today. Steven had taken some liberties and gotten away with them but so what. He either had to have sex with my mom by tomorrow night or I was gonna be a thousand bucks richer.


The next day I woke up pretty early. I knew that today was the last day of the bet and I could almost smell the money that would soon be mine. I walked downstairs and told mom that later tonight I was going to a party. She told me to be careful and to not drink any alcohol. I reassured her I wouldn’t before playing some video games for a few hours. About six, I got up off the couch and went to take a shower. After I got some clothes on I walked downstairs to tell mom I was going out for the evening.

“I’m gonna go ahead and go to the party. A couple guys from school I know got a band to play and everything.” I lied.

“Alright, just be careful and don’t come back too late, ok?” Mom said.

I got into mom’s car and drove off down the road. I circled the block a few times then I parked down the street a bit before turning off the engine and the headlights. It didn’t take long before I saw Stephen walking up the sidewalk towards the house. Stephen knocked on the front door and moments later I saw mom let him in. I snuck up to the house and peered in through the window. They weren’t in the living room so I went around to the back of the house. The window right above the kitchen sink was open a few inches and as I got closer I could hear them talking.

“Why didn’t you go to the party with Rich?” Mom asked.

“He was supposed to meet some girl there and I didn’t want to be the third wheel. He would’ve done the same for me.” Steven said.

Mom and Steven talked for a while longer before going into the living room. I made my way back around the front of the house. Without any open windows I couldn’t hear anything that was said but I had a good view.

Steven sat down on the couch followed by mom. She’d apparently been having a little wine tonight because there was an empty glass on the coffee table. They both got comfortable and watched T.V. for a while. After about thirty minutes I saw Steven stand up and motion to the kitchen. Mom nodded and Steven grabbed her wine glass before walking out of the living room. While I waited on Steven to come back I looked at mom sitting on the couch. She was wearing a simple light blue dress. She must’ve expected to spend the night alone because her hair was down and she didn’t appear to have any makeup on. My thoughts were interrupted by Steven coming back into the living room.

“Damn, you think that’s enough?” I thought to myself as I saw mom’s wine glass filled to the rim.

Mom didn’t take her eyes off the T.V. as she brought the glass to her lips and took a big gulp. Things went on uneventfully for a long while after that. It was so boring that I was starting to nod off as I kneeled in the grass. A while later I glanced at mom’s glass and realized that she’d drank the whole thing. A few seconds later I noticed that Steven had put his arm around my mom’s shoulders. That must’ve been his favorite way of breaking the ice because it wasn’t the first time I’d seen him do it. After nothing happened for a little while I sat down to give my legs a brief rest. I checked my watch and was relieved that it was almost eleven.

“Just a little while longer and I’ll win this fucking thing.” I thought.

After my legs felt less like jello I stood up again. The sight that greeted me was enough to cause some concern. Mom had her legs up on top of Steven’s as she watched television. I watched intently as Steven brought his hand up and sat it on my mom’s knee. I bit my lip nervously as mom remained unfazed by Steven’s actions. Mom glanced over at Steven and I thought she might say something but she simply smiled. The next thing Steven did caused me to stop breathing for a moment. As I watched Steven slid his hand up under mom’s dress. My heart started to accelerate. As she watched T.V. mom used one hand to take another drink of wine as the other pulled Steven’s hand out from under her dress. Steven was undeterred though because soon his hand was back on mom’s knee. He kept his hand there for a while before leaning over and lightly kissing mom on the shoulder. My mom just took another big sip of wine. Out of the corner of my eye I saw Steven’s hand slip under mom’s dress but not too far. It appeared that he was testing the waters again. Mom sat there unfazed for a bit, that was enough for Steven I suppose. Slowly is hand started to move upward.

“I know he’s not gonna…” I said as Steven’s hand slid even further under mom’s dress.

Mom’s mouth opened slightly and she leaned her head back against the couch. I couldn’t tell exactly where Steven’s hand was but I could guess. I couldn’t quite believe that she was sitting there with Steven’s hand god knows where under her dress. Steven leaned over and I thought he was going to whisper something else to her but he began to kiss my mom’s neck lightly. His hand was moving a lot under mom’s dress but from my vantage point I couldn’t tell what was going on so I made my way to the window right behind the T.V. As I slowly peeked in my mouth fell open.

“Oh shit…” I thought.

From this spot I could see exactly what Steven’s hand was doing. Mom’s dress was pulled up pretty far and I could see his hand rubbing the front of her panties. I started to breathe really hard at this point. Mom was wearing some tiny white panties and Steven’s hand was cupping her pussy. I looked up at her face just in time to see Steven kiss her deeply. Mom put her hands on Steven’s chest as if to push him away but she made no real effort. Eventually mom’s hand grabbed the back of his head and they made out like teenagers. I watched as Steven’s hand pushed mom’s panties to the side a bit and for the first time I saw her pussy. The tiny landing strip caught my eye and even I had to admit it was sexy.

“C’mon mom…don’t do this…” I pleaded.

Steven rubbed up and down mom’s slit until he finally inserted his middle finger into her depths. I watched her face contort as my best friend finger fucked my mom. My mom squirmed and wiggled on the couch as Steven kept up his assault. I don’t know how long that went on but eventually she clinched her eyes shut and grabbed Steven’s wrist with her hand. I couldn’t believe what was happening as I watched my own mother cum on my friend’s fingers.

“It’s ok…he hasn’t had sex with her….just fingered her.” I said to myself.

After a few minutes mom let go of Steven’s hand and he kissed her again. Their mouths were open wide so I knew there was definitely tongue involved. Steven stood up quickly and took his shirt off. Mom laid there with a blank look as Steven pulled his pants and underwear off in one long motion. I couldn’t believe that I was looking at my best friend naked standing in front of my mother. I couldn’t help but notice that Steven was pretty big. I measured myself one time and was happy with my seven inch cock but Steven looked to be even bigger. Mom just sort of sat there staring, she didn’t look like she was sure what to do next. Steven took her hand and placed it on his cock. Mom slowly started to stroke up and down as Steven leaned his head back in pleasure. Mom had one hand on Steven’s cock while the other was over her mouth. It was like she couldn’t believe what she was doing either. After a while Steven put his hand on the back of my mom’s head and pulled her towards his cock. My mom shook her head and braced her hands on Steven’s hips. Maybe there was hope after all I thought. Steven was undeterred though. He brought mom’s hand back to his cock. Mom was looking up at my best friend as she stroked his hard cock. Steven leaned down and kissed her again. They kissed for a long time with mom’s hand sliding up and down Steven’s cock all the while. After the kiss Steven stood up and again slowly pulled her head towards his cock. The kiss must’ve weakened her resolve because the time mom opened her mouth and sucked about three inches of Steven’s hard cock into her mouth. Steven let out a moan I could hear through the closed window. Slowly but steadily Steven began rocking his hips as he held mom’s head with both hands. Eventually he was face fucking my mother right in front of me. Mom’s pink lips slid up and down Steven’s glistening cock and before long she was taking almost the whole thing down her throat.

“Jesus Christ…” I said as mom gave Steven the best blow job he’d ever had.

Finally Steven pulled his cock from mom’s mouth and pulled her to her feet. He kissed her briefly before turning her around. Steven got on his knees and unzipped mom’s dress slowly. Afterwards mom pulled the dress down and I saw Steven take his cell phone out of his pants and put it on the coffee table. I knew that he was filming what was happening but there was nothing I could do about it. After putting his phone on the table Steven turned his attention back to my mom. He slowly pulled her panties down her long legs. He head was even with mom’s ass as he grabbed her rear tightly. He squeezed mom’s ass tightly before slapping her ass lightly. Steven remained on his knees as he guided mom and onto the couch. Mom was wide eyed as Steven spread her legs and brought his head down to her pussy. Her head shot back against the couch and she grabbed Steven’s head with both hands. I watched the back of Steven’s head for about twenty minutes as he ate my mom’s pussy. He must’ve knew what he was doing because mom sure liked it. I could hear her moan from outside. Her eyes were closed most of the time and once in a while her tongue would trace her upper lip. Before long, as I watched wide eyed, mom’s legs clamped tight around Steven’s head and she came again. After convulsing for close to a minute, mom’s legs eventually fell apart limply. Steven eventually got up and they kissed again for a long while. My friend then stood up and pulled mom to her feet. Then he sat back down on the couch with his cock pointing straight at the ceiling. I watched as my mom ran her fingers through her hair before straddling Steven. I could hear her moan loudly as she lowered herself down onto his cock. My mouth fell open as inch after inch of my friend’s cock disappeared into my mom’s pink pussy. Mom sat still for a moment before she started to ride Steven’s cock. I watched intently as her wet pussy slid up and down Steven’s hard cock. His hands were all over mom’s tits but I couldn’t see them with her back to me. That was soon remedied though as mom got up and turned around. She grabbed Steven’s cock and guided it back into her pussy and she bounced up and down on his cock. Steven brought his hands around to mom’s tits and squeezed them tightly.

“Oh shit…” I thought as I noticed that my own cock was rock hard. By this time I had lost all track of time.

Mom’s head was leaned back as Steven fucked her hard. His hands left mom’s tits as he grabbed her hips and began to thrust upward as hard as he could. Even with the window closed I could hear mom moaning. Steven fucked her hard and fast for another five minutes or so before he slammed her down on his cock as hard as he could. Mom was grabbing her tits with her head back as Steven came inside her pussy. I could see his balls convulsing as he emptied his cum into my mother. Mom ran her fingers over her tits as she sat on Steven’s lap. She leaned back against him and kissed him again. As I watched, Steven’s limp cock slipped from my mom’s pussy followed by a large amount of cum. I fell backward into the grass breathing heavily as I processed what I’d just seen. I almost forgot about the bet when I looked at my watch.

“FUCK YEAH!!!” I said as I noticed the time.

It was one thirty in the morning. I had technically won the bet. However, I’d just witnessed my mom getting her brains fucked out by my best friend. I didn’t quite know what to think. I peeked back in the window to see mom still sitting on Steven’s lap. They smiled at each other before mom slid off of my friend. Steven said something and I watched as my mom brought her head down to Steven’s limp cock and sucked it into her mouth. Steven smiled as my mom sucked his cock back to life. It didn’t take long before he was rock hard again. Mom pulled Steven’s cock from her mouth and jerked it rapidly as she licked his balls. Mom sucked Steven’s cock back into her greedy mouth as her hand found her pussy. Every minute or so I would notice Steven’s eyes opening long enough to glance down at his phone. No doubt making sure that he was in the right spot. After a few minutes mom pulled Steven’s glistening cock from her mouth long enough to say something. Steven said something back before pushing mom’s head back down onto his cock. Shortly thereafter I heard Steven groan and mom’s cheeks began to balloon. I’ll give credit where credit is due, mom kept Steven’s spurting cock in her mouth the whole time, swallowing only when Steven had stopped convulsing. Time stood still for me as my brain tried to process what’d happened. When I came to, mom was pulling her dress back up and Steven was stuffing his cell phone back into his pants. They both didn’t say a word as they dressed. I waited a while before going back to the car and calling him.

“Well man, how’d it go?” I asked.

“Man…I fucked your mom! I got proof and everything.” Steven said excitedly.

Later that night on the front porch Steven showed me the video not knowing that I’d watched the whole thing unfold.

“Well, that’s proof alright.” I said.

“Man I still can’t believe it.” Steven said.

“Well I guess there’s still the thousand bucks you owe me.” I smiled.

“What the fuck ever man, you saw it with your own eyes. I fucked you mom, she came like three times.” Steven said.

“Check the time on the video dumbass.” I said.

Steven checked back to the video and after a few minutes he said “motherfucker.”

He could clearly see that it was after midnight before he actually fucked my mom. He quietly relented and dug the money out of his wallet before handing it to me. I took the money and made my way back into the house. I walked in the front door and saw mom sitting on the couch. She was reading a book as I passed by.

“Did you have a good time?” Mom asked.

“Sure did, how about you?” I asked.

“Um..yeah…same old same old.” Mom said.

So here I am sitting in my room after watching my mom get fucked by my best friend. I’m not angry or anything like that. I won the money after all. I don’t hold anything against Steven, he’d liked my mom for a long time and we’re best buddies. Mom didn’t seem to be upset or anything and there’s no telling how long it’s been since she’d been laid. I leaned back onto my pillow and smiled. What a crazy fucking week it’d been. Well one thing’s for sure, next week I’m gonna go shopping with this extra spending money. I earned it.

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sdsioux wrote

Too long a buildup for a short story.