Watching My Mom Ch. 01

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Alex and his mom's boyfriend comes to an arrangement.
4k words
4.35
146.7k
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Part 1 of the 3 part series

Updated 06/08/2023
Created 08/13/2017
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This is my first story so if there are any errors, sorry!

This deals with some light incest, cuckolding and voyeurism.

And most importantly, this is a fiction.

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I.

I'm Alex. I just turned eighteen and this is my fucked up story. My life was normal as it could get. Average student struggling with his teenage years. Well everything was pretty average until I was 15, maybe 16; I don't know. I started to pay more attention to my mom. Before that she was the farthest thing I could think of when I'm jacking off. But as I've got older, I noticed how hot she is. My mom was always been very conservative. But I noticed how sexy her body is underneath all of that unflattering clothes. Since then, she was my only fantasy to jerk off to. She was a single mother, and we didn't had very close relatives. Apart from occasional visits from my grandparents, and few of mom's closest friends, we didn't had much visitors.

My mom, Jenna, is forty-six years old. She was 5' 5" with short dark blond hair. She was little bit chubbier than she was 10 years ago but she wasn't fat. Just not skinny as a super model. She worked all week as a secretary at a small family run business. With more relaxed working hours, we spend most of our time together. She was single for the longest time I can remember. When my grandparents asked her about that, she always make up some excuses. But I can see she is lonely. After all there's so much a son could provide. It all changed when she met Mike.

She met Mike at a church of all places. My mom wasn't religious, but couple of her friends were. Sometimes she attended services with them. One of said friends introduced my mom to her husband's friend, Mike Greer; a doctor at a local hospital. Apparently they hit it off right there and began officially dating soon after. I met him couple of months later. All of this was strange to me. For the past eighteen years I haven't 'shared' my mom with anyone. But there I was eating alone while they were on a date. I would've hated the guy if he wasn't 'cool'. In fact he was great. With my mom, with me, with everyone. So I wasn't mad as I would've been.

Mike is at least 50 but you couldn't tell him by looking at him. He worked out regularly and it showed. And my conservative mom tried her hardest to impress him. Her clothes became more revealing. She wore more expensive makeups and complained about being fat! To me and to my fantasies, it was christmas.

On that fateful day as they say, mom went on a date with Mike. It was their first year anniversary. Their first special day. I watched some TV and went back to my room to sleep. I was awaken by the noise I heard from the living room. I heard some giggles and shushings. I was curious. And my cock was twitching to the thought of mom getting fucked on the couch. I got up and slowly walked to the living room. It was dark except for the one light that was glowing. I saw Mike sitting on the couch and mom kneeled in front of him. I didn't took that much of a time to realize what my mom doing. I quietly watched them. Mike moaned as his head turned up. Mom's head bobbed up and down. My cock after seeing all of this trying it hardest to split my shorts. My hand went down and stroked my cock through the shorts as I watched them. Mike tapped mom's shoulder and she got up, turned around and lifted up her dress. After shedding every piece of clothes she was waring, she slowly sat down on Mike's cock. I couldn't see much because of the dark but I was frozen up. My mouth was watering up to the sight of my mom bobbing up and down on her boyfriend. My heart stopped when I saw Mike's eyes watching me. My mom was enjoying the cock, she was moaning and even pinching her nipples. But Mikes eyes were on me. I was frozen up with my hard cock in my hands. I couldn't move. Suddenly I saw his smile. A fucking smile. Even in the dark I could make out his face smiling hie regular 1000 watt smile at me as he fucked my mother. I pushed my cock down in my shorts and ran to my room.

Next morning was awkward. I avoided my mom's eyes for the whole day and fortunately Mike went to work early. He obviously haven't told my mom what happened and I can't express how grateful for him for that! So the day went by. My mom went to her office. I played some games with my buddy's and tired to forget what had happened last night. When I came home mom was already came back from work and preparing dinner. I just said hi and went to my room. After couple of minutes I heard a knock on my door. Mike walked in. Shit.

"Hey man... is this a good time to talk?" He asked with a friendly smile.

"I guess..."

"Listen... I'll get straight to the point... we both know what happened last night."

Here it comes.

"Oh... don't worry man! I'm not going to rat you out or anything... relax okay?"

"Sure"

"I understand what you are going through. Your mom, Jenna is a very attractive woman. It is natural. I mean I have hard time keeping my hands off of her... But I digress. The point is, don't worry. You are a healthy straight guy and she's a... well a sexy woman. We just have to figure something out."

"Uh... figure something out?" Now I'm curious. I thought this would just be a talk, it's natural but don't do it again bla bla bla. What's there are to figure out?

"Well you see... you like to watch right?... right?"

"Yes" I finally answered.

"And I like to being watched. Not that I attracted you if that's what you thinking. I'm saying your mom and I have um... very special relationship. This is a big secret okay? So it can't get out. I don't think you've noticed that. Your mom is what they call a hot wife. We swap partners, threesomes you get the idea right? And we are pretty open to try out new things. So if you are interested I can set something up so you can watch us. Your mom wouldn't know of course but it'll be our secret."

I can't believe it! My conservative mom, the woman that hadn't had a boyfriend for eighteen years is a fucking hot wife?

"I..."

"You don't have to answer now... just think about it okay?"

"Uh... okay. Just a question though... are you pulling my leg?"

"No! I'm not pulling your leg. We all have our kinks right? You like to watch your mom and jerk off. I like to see my partners sleeping with other people. Your mom likes to... lets say 'party'. One of the reason we got this close this fast is because of our kinks. As you can see it is not easy to find people that are in to our lifestyle. We understand each other."

"But... but she... she was single for so long."

"Well she haven't met someone like me and she thought of you. You were young and you know. But she had few partners. But not serious relationships."

"Wow... I thought I knew my mom..."

"Hey... she's still your mom. There's nothing new. Lots of people are different when it comes to sex, they keep their lives separate. I mean I don't want my coworkers or patients to know what I'm doing in my bedroom."

"I understand... I guess. I'm in."

"Are you sure? You can't unsee things."

"I'm sure. And you are right. And if I said no, I'll regret that for a long time. If I don't like what I see, I can stop right."

"Yeah absolutely."

"Cool"

He patted my back and left the room. I just fell on the bed and thought about what just happened in the room. I began to think about what I just agreed to do. I felt bad. I felt guilty what I'm going to do. I know it's not right. But I can't stop think about it. As long as I'm just going to watch them nothings going to change right? I heard another knock.

"Alex dinner's ready."

After that evening, life returned back to normal. Although I've talked with Mike everyday, he haven't even spoke a word about our little agreement. I began to think that he change his mind. It is a big deal after all. While I still admired my mom's beauty, I stopped spying on her or them. One day I got an message from Mike, while we all watching TV. I looked at him but he kept watching TV. I opened the message.

|> Alex, are you still interested?

Yes <|

|> Good. Exactly after this is over

|> Go to your mom's closet

|> Keep your mouth shut & clean up after yourself!

OK <|

My patience was never been that great. Now I hardly can contain myself. I knew I shouldn't make a fool out of myself. So I tried my hardest to act normal. As soon as the credits started to roll I ran to my room, got my trusty sock and hid in my mom's closet. Closet was lot more roomier that I thought. It hid me and my hard cock perfectly and I had a great view in to the bed. I heard the door opening. This is it.

"Mike! can't you wait until we get to the bed?"

"Do you realize how hot you are? Thank me I didn't fuck you in the living room!"

"Oh Mike... I sometimes think that you're a sixteen year old that somehow got trapped in a fifty year old's body!"

"Hey! I'm forty nine!"

They finally came to my field of view. They were making out while Mike trying to get her clothes off. Mom helped him to get rid of her clothes and then undressed him. My mom looked fucking fantastic! She looked way better under good lighting, that for sure! My mom was really pale. Her breasts are bigger than I thought. More than a handful. Her pink nipples stood out and her ass was tight as hell. Working out with Mike all these months definitely payed off! She kept her blond pubic hair trimmed. Her slutty smile nearly made me cum.

She pushed Mike on to the bed. He sat down on the corner of the bed while she knelt down between his thighs. I was amazed to see this forty nine year old had a six pack! His cock was maybe little larger than mine. Which is around six inches. For some reason I was expecting a bigger cock. Maybe because all of the hot wife talk.

"Mmm you're so hard..." She said while stroking him.

"This is what you are doing to me Jenna..."

"Ooh is this my fault? I guess I have to fix it then"

God I fucking loved how she talked. Like Mike said, she definitely was a different person in her bedroom.

Her lips wrapped around Mike's cock. I heard his soft moans while she was sucking on him. Soon his cock got covered with her saliva. It seems like mom was really got at giving head.

"I'm gonna cum Jenna!"

"Cum for this little slut baby... cum for me!"

He shot his load in to her mouth. Just like a good slut she swallowed all of it. After cleaning herself she climbed on top of Mike and kissed him. He then got up carrying my mother and laid her on the bed. Just like mom, Mike then dropped to his keens and began kissing her thighs. Mom let out a soft moan.

"Lick my pussy baby... please!"

So he began licking her. Room was filling with my mom's sexy whimpers and moans. She got louder when he entered two fingers and touched her clit with his tongue.

"Ow fuck yeah... just like that baby..." She was holding Mike's head down with her two hands.

"Ah... I'm cumming baby... I'm cumming!" It was the loudest I've heard my mom yell. I couldn't believe I haven't heard her yell before.

Mike pulled out his fingers and licked them. My mom looked at him and bit her tongue.

"Lets do doggy tonight?" My mom asked.

"Sure thing honey"

Mike flipped her around and my mom got on all fours. Mike pulled her beautiful cheeks apart and licked her pink asshole. Mom's little toes wiggle like crazy. Then Mike climbed on to the bed and positioned his cock against her pussy. I was disappointed because mom was covered with Mike's ass but at least I could see her jiggling breasts. He slowly entered mom's pussy and began pumping in and out. I could hear they both moaning like crazy fucking each other. My hand never left my cock. Right now I was pumping to the Mike's rhythm. But I couldn't last long enough to cum with them so I shot my load in to the sock. They kept fucking for few more minuets. Mom's moaning and swearing got louder as she came and got quieter after that. When Mike pulled out of her I could see his cum dripping down from my mom's pussy. My cock got harder again.

After all of the action, they both got out of the bed and began kissing. It was very intimate. I was feeling little jealous but I was glad that my mom found someone she really loved. After making out, my mom got in to the bathroom and I heard the shower running. After Mike slowly closed the door, I got out of the closet. It was little weird standing next to the naked guy that just fucked my mom but it was oddly exciting.

"Did you enjoyed that?"

"Fuck yeah... It was amazing!"

"You did cleaned up after you right?"

"Oh yeah... don't worry about that."

"Remember this is a secrete! Nothing of this could go out. If you keep your mouth shut you'll see way more that this okay?"

"Relax Mike... I'm not gonna say I peeped on my mom to anyone."

"Good... now get out"

I got in to my room. I was still hard so I replayed what I saw in my mind and jacked off. Man what a rush!

II

So once or twice every month I got to see my mom and Mike fucking each other. Mike and I got lot closer and we frequently messaged each other about mom and stuff. He really got off of talking about them with me. I was little nervous at first but I got used to it. He sent me pictures of her naked, clothed in slutty lingerie and they fucking each other. It was great. Mike told me that he's holding off on things that are little too much for me. I begged him to send me some of those things but all I got was "be patient!".

The pictures of my mom was very useful when I was busy with my studies at the college. Yup I began college. I was there when he finally sent something interesting.

It was a video in Mike's POV. My mom on all fours, Mike's cock was covered in lube. He parted her cheeks with his free hand slowly pushed his thumb in to her puckered hole. I could hear my mom's sexy moans as he fucked her ass with his thumb. Mike then pulled out his thumb and pushed in his pulsing cock. Mom's moans got louder. And he sped up. He slapped her pale ass cheeks hard every once in a while, making them red. Mom begged to be spanked. He then grabbed her by her beautiful blond hair and showed her face to the phone. Mom's face was covered in pure ecstasy. She licked her lips.

"Mmm fuck me harder baby... fuck my ass"

Needless to say I just came then. Mike pumped some more and finally pulled out, turned my mom around and pushed his cock in to her mouth. She eagerly sucked every drop of his cum.

|> Amazing huh?

Yeah <|

I couldn't even believed that's my mom! <|

|> Listen

|> Remember I told you that your mom's a hot wife?

Yeah? <|

|> Well since you aren't here

|> There are lots of hot wify stuff going on

|> If you are okay with that

|> I could arrange the closet when you got your summer break

Do you even have to ask now? <|

I'm in <|

So the summer break finally came. I came back to my home, my mom greeted me with a big hug. When I was finally alone with Mike, he asked aside.

"Alex... I can do better than closet."

"What do you mean?"

"Well... Jenna liked to get... well um"

"It's okay Mike to get fucked"

"While blindfolded"

"Are you saying that I could watch you guys closer?"

"Well thing is... your mom doesn't like to get blindfolded and fuck me. That's her special thing reserved to her bull"

"Her bull?"

"'Bull' is a man that has control of a hot wife. In this case Jenna. You'd have to watch him... fuck your mom. And he'll see you too."

"Oh... wow. Okay. I mean I guess he's discreet?"

"Oh yeah... he's very discreet."

"Uh I don't know Mike... I'd have to think about it."

After knowing my mom is a hot wife, I 'researched' quite a bit about the subject. And I found really interesting information. But being a non-active participant with a stranger, still seemed too much. I joined mom and Mike for the dinner. I was glad to see mom's usual outward self wasn't changed even after doing all of this. We caught up all of the thing we guys missed over the dinner. It was great.

The need for watch mom's slutty side closer still lurked my mind though. I wanted to be there. Right where the action is. So i texted Mark "Yes". I'm in quite a bit already so what's this going to change?

Two days later I got a text from Mark "Don't fall asleep". I knew it was on. I couldn't sleep even I wanted to. It was around midnight when I finally got another text from him "Come to our room, remember the rules no sound no mess". I slowly walked in to their room. It took me few seconds to see all of the things happening in the room. My naked mom was blindfolded and laying on the bed. Mike was naked and standing closer to the door. The stranger, black guy who stood around 6' 2" maybe more was standing right next to my mom. He was still fully clothed. He looked at me and gave a smile and node. I did the same.

"Please daddy... I can't wait anymore" It was my mom.

"Can't wait for this black cock huh?" The stranger whom I later found out is named Jason; asked her.

"Yes daddy"

Jason leaned in and began stroking mom's cunt with his thick fingers. My mom spread her legs apart and gave him access. Her fingers were pinching her nipples while Jason finger fucked her. He then moved closer to my mom's red lips and kissed them while his fingers still buried deep. Mom's little hands grabbed him by his hair and pulled closer to her. After kissing her, Jason pulled out his fingers and replaced them with his tongue. He teased mom's swollen clit by barely touching it with his tongue's tip. My mom thrust her hips up to get a better feel.

"Eager little slut" Jason commented. Mom replied with a beautiful giggle.

Jason got up and began removing his clothes. I looked at Mike and he was slowly stroking his cock. My own cock was straining in my pants. He saw this and gestured me to remove my clothes. I dropped my pants and my hard cock sprung out. When I looked back at the bed, Jason was removing his pants. I'm a straight guy, but even I was amazed how good he looked. He had a lean swimmer's body. He end up being one of the reasons I finally joined a gym. And his cock matched porn black guy stereotype to a T. It was thick even in his own hands and long, maybe 8 or 9 inches. Either his girlfriend really loves him or really hates him.

He dragged my mom to a corner of the bed so her head sticking out. Jason then placed his cock on her face. It was longer than her face! She then grabbed it and began stroking it. After stroking and teasing it's head with her stretched out tongue, she opened her mouth. He slowly pushed the cock in her mouth but it was too long and thick to my mom to completely swallow it. Her little mouth was so stretched up but she pushed it down as far as she could. This continued for some time. Jason then pulled out his cock and stood sandwiching mom's head between his thighs. Mom's head moved up an licked his asshole. Of course I saw this on porn but seeing my mom do it to Jason was amazing. He stroked his cock while mom cleaned his asshole. I could see him getting closer. He then stopped and climbed on to the bed. Mike handed him a bottle of lube. Jason covered his cock with lube and positioned himself on top of my mom missionary style, then slowly pushed his cock in.

I could see my mom's pussy was stretching to accept his member. Mom was whimpering in pain while stroking her clit. He pushed as far as he could, leaving maybe quarter of his cock out. Jason pulled bank and repeated his slow push for few times. Every time he got faster. Eventually mom's whimpering turned in to moans and they were fucking hard. Jason leaned in and kissed her again.

"Fuck me daddy... fill your slut's cunt with your cum" Mom was chanting something along thins line every time he pushed in.

After fucking her missionary for a while, Jason turned her around to doggy. Again he pushed his cock in and they were fucking again. Mom's moans and his grunts filled the room. I was stroking my cock. I couldn't handle it any longer and I came in to my trusty old sock.

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