My Son's Cumbucket Ch. 01

Story Info
Stepmom finds new passions in younger man.
6.7k words
4.53
194.6k
342

Part 1 of the 9 part series

Updated 02/23/2024
Created 12/23/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Have you ever experienced a glass shattering moment that completely ruined everything about you? Well I have and that day was when I saw my step son masturbating for the first time. Some context: I married this older man a couple years ago. He's a good deal older than me and he has two sons. One son is away at college and the other is about to graduate high school. While I am still older than both of his sons, it is still alittle strange to be closer in age to my husband's sons than to my own husband. Now before you start branding me the gold digger, yes my husband is very wealthy and yes i do not have a career, per say, but i didn't even know how much money he had until we got married, nor did I know he was so much older than I was. I knew he was older but not as old as he is until I saw his birthday date on our marriage license.

Well one day I was outside doing some gardening. Yes i still got my hands dirty even though we had a gardener that could do it all for me but i grew up hands on and i like tending my own garden. Anyways, as i was clearing out some weeds and preparing the ground for new plants i was really close to the half window that saw into Jack's bedroom in the basement. When i realized that i could actually see into his room i was about to knock on his window but then i saw he was laying on his bed and thought he might be asleep so i thought better of it. The window was half hidden by this shrubbery bush and I did even know it was there. I went back to my gardening and out of the corner of my eye I kept seeing movement in Jack's room. I kept looking to see if he was awake or asleep and then I saw it. The movement I noticed was the sheet fluttering from his crotch.

It wasn't until he flung the sheet off of him and I saw something that made me stop and nearly gasp in shock. Jack was masterbating his massive cock. Like this was easily twice as big as his father's, which his father had a good size dick to begin with, much bigger than most of the asian men i grew up around. I must've started for a long time because at some point Jack grabbed a sock and covered his prick with it and I saw his head roll back as he obviously came into the sock. I could see Jack's chest rising and falling in obvious deep breaths. When he got up I quickly came to my senses and scuttled away from the window and tried to get back to my gardening.

The damage was already done. As I moved back away from the window I realized that my pussy was soaking wet in my tight spandex shorts. I was on my hands and knees in the dirt and soaking through my sorts having watched my own step son jerking his big hard cock. This was so wrong.

When I finished with the garden, quitting more accurately since I could think about anything but how big Jack's dick was, I got back into the house and was surprised to see Jack in the kitchen making himself a sandwich. I froze when I saw him and became very self conscious about how I looked and couldn't even meet his eyes after what I just witnessed. I was standing in the kitchen, my tank top soaked with sweat and a wetness between my legs that I could tell was more sweat or pussy juices. The cold air of the AC was not helping me either as I felt my nipples get as hard as diamonds. Definitely not the sight I wanted to present right in front of someone I just saw masturbating.

"Uh hi Jack," I saw trying to keep the nervousness out of my voice, "what uh whatcha up to?"

"Hey Naomi, not much just getting a snack. I am starving," he said as he stacked his sandwich.

"I wonder why," I said to myself.

"Cool....cool um i'm going to go take a shower...'' I trailed off telling him gesturing upstairs and smiling nervously.

Quickly I made my way past him and up the stairs and into my private bathroom. I stared into the mirror trying to shake the nervousness out of me. While Rich, my husband, was not the first man I ever had sex with, he is the second. Jack is the only other penis I have ever seen and I was by far the biggest!

"No stop Naomi," I told myself in the mirror, "he is your stepson. Just forget anything you ever saw and move on."

I looked into my almond eyes and tried not to see the hungry behind them. My chest was heaving, my C cup breasts raising and falling as I tried to control my breathing. I ran my hands through my long dark hair and took a deep, deep breath. Once I calmed down enough I got undressed, nearly peeling myself out of my damp clothing. I got into the walk in the shower and sighed at the soothing water. I draped my long hair over me to soak in the water. This took a couple seconds because I liked to keep my hair long enough to just meet my lower back. Most of the time I braid it but today it was just in a loose ponytail.

As I lathered myself in soap my mind began to wonder back to what I saw through the basement window. Jack lay on his bed, his hand firmly grasping his massive hard cock. His chest raising and lowering as he stroked his hard dick.

I noticed now I was now rubbing myself as I recalled the scene. I couldn't believe I was doing this. I was actually masturbating myself while I thought about my stepson masturbating. What kind of pervert was i?

I heard a noise and quickly pulled my hands away from my smooth crotch and tried to look through the foggy glass walls. I turned off the water and reached for my towel and stepped out of the shower. My heart was pounding as I looked around the bathroom and I saw my hairbrush on the floor. I sighed and rolled my eyes as I bent over to pick it up. As I put it back on the counter I realized that the door was slightly open. Which was weird because I swear I closed that when I came in here. At least I thought I did.

I shook my head and tried to compose myself. I dried myself off and went to get dressed. I've gotten into the habit of not wearing panties if i wasn't going anywhere and most days i really didn't have to and most of the time i didn't need a bra because while my breasts were rather sizeable they were still perky and held themselves up just fine.

As I looked through my clothing I saw everything in a whole new light. Everything I had seemed much too inappropriate to wear around the house with a masturbating teenage boy in the basement. I really need to go to the store and get some baggy clothes or something. I don't think I could bring myself to wear a moo moo. I liked my body and always felt comfortable in tight clothing. While I am not necessarily skinny, I am not fat. I had some healthy build to my 5 foot stature.

I settled on some leggings and a flowing blouse. As I walked downstairs I expected to see Jack still in the kitchen but he was nowhere to be found. His sandwich was on a plate on the counter with a big bite out of it but no Jack. I didn't think much of it so I went downstairs to do some laundry. As you go downstairs there is a big open room with carpet and a big couch but you have to come all the way downstairs to see anything. At one end of the room is Jack's bedroom and bathroom and on the other is the laundry room and a utility room. I went into the laundry room and started emptying the dryer and changing over the washer and as I looked around to see what to load into the washer I saw a basket of Jack's clothing. Now Jack can do his own laundry but I will do it if it's there and I have time.

Looking at Jack's basket I hesitated, remembering what he did with his socks, because right on top there were 5 single socks visible. I bit my lip and steeled myself. As I grabbed one of the socks I couldn't tell if I was relieved or disappointed to find that it was just a regular sock. Shaking my head I grabbed a handful of his clothes from the basket and threw them in the washer. As I bent down to pick up a sock that fell from the bundle I froze when I grabbed it.

The sock was soaking wet and oozed when I squeezed it. I quickly dropped it realizing why it was soaked and I just stared at my hand. It was slick with a sticky white substance. I flexed my fingers severely several times, feeling the sticky sensation. I brought my fingers to my nose and smelled the familiar scent of semen. I looked down at the sock on the floor and then back to my hand.

"Well it's not like I can get any less sticky,'' I told myself as I bent down to pick up the jizz sock again.

This time I felt the whole sock and found it to be completely soaked. I even squeezed it again and felt and saw more liquid bleed from the sock.

"How could there be so much semen in this sock?" I wondered to myself.

It was rather impressive at how much semen was obviously coating this one sock. I balled it up more and squeezed it again and just as it began to drip from my hand I cupped my other hand underneath and caught more of it. There was a good size puddle now in my one hand. I squeezed the sock dry and threw it into the washer. I looked at both of my hands and didn't know what I should do now. I looked at the puddle just sitting in my cupped hand and an idea popped into my head.

Biting my lip I looked to the laundry room door and then back to my hand. This was a crazy idea. I slowly brought my hand to my mouth and I stuck out my tongue. The moment my tongue touched the liquid in my hand I panicked and stopped and grabbed a towel from the clean pile and whipped my hands. I can't believe I actually considered tasting my own stepson's jizz.

I finished loading the washer and started it. I grabbed a basket of clean clothes and left the laundry room. I stopped to look at Jack's door before continuing up the stairs. As I passed the kitchen I noticed his partly eaten sandwich was still on the counter. I put the basket down and then looked back to the basement.

"I wonder," I told myself.

I walked to the back door and walked around the house to my garden and got on my hands and knees and crawled back around that bush and found Jack's window. Sure enough there he was, laying on his bed, this time not bothering with the sheet as he variously stroked his hard cock.

I gasped as I realized that he must have been masturbating while I was in the laundry room. While my hands were soaked in his semen, while I very nearly tasted his cum I harvested from his jizz sock. I felt myself getting wet again as I looked on. I brought a hand to my crotch and felt the warmth and wetness. I slid a hand into my legging and found my clit and began to rub it gently.

I could hear Jack moaning this time. I bit my lip to keep myself from moaning audibly. I normally can be quite vocal in the bedroom, but I did not want to make a sound and get caught like this.

"Fuck yeah Naomi," Jack moaned.

I froze and my eyes widened as I heard him say my name while he stroked that big hard beautiful cock of his. He was masturbating thinking about me! I nearly whimpered but brought my hand to cover my mouth. It was wet with my juices and I remembered that this hand was just recently soaked in Jack's cum. I looked to my hand then to Jack and saw he grabbed another sock and was fixing to cum in that one too. I looked back to my hand and bit my lip as I returned it to my crotch. I was now not just rubbing myself as I watched my step son jerking off but now I was rubbing my wet clit with my hand soaked in Jack's sticky cum. The moment I saw Jack orgasming into that sock I came at the same time. I bit down on my lip hard so that i didn't make a sound.

I panted there in the dirt behind a shrubbery bush. I just made myself cum watching my stepson jerking off to me. I felt so dirty but not in a way that a shower would do anything. I crawled back out from my hiding spot making sure that Jack was still on his bed. As I stood up I dusted myself off. I had dirt marks on my knees. I figured it'd be best to just change. So I went back inside and went back through my clothes to find something appropriate.

"What does appropriate even mean anymore?" I asked myself.

I settled for another pair of leggings and went back downstairs. When I saw Jack at the kitchen counter finally eating his sandwich I kind of blushed. I went to the fridge to get water.

"So uh jack, do you have a girlfriend?" I tried to ask nonchalantly.

When I raised my head to look at him he just kind of froze there with a mouthful of food.

"Um, no I don't. At least not anymore," he mumbled in response.

I nodded trying to keep it casual when I had a question I really wanted to ask him.

"How long have you been together?"

"not long a couple months."

"what happened?"

He paused for a moment trying to pick his words very carefully. I could almost see the steam coming from his ears.

"we uh you know just didn't work out. We wanted different things."

"like sex?" I blurted out my heart in my throat.

Jack choked on the last of his sandwich.

"That's none of your business," he said, clearing his throat.

"No you're right it's not I'm not your mother, but at the same time I'm NOT your mother," I emphasized, "I just want you to know that you can talk to me about this kind of stuff."

"about sex?"

"... About sex or masturbation or fantasies whatever. I want you to know you can confide in me. And I won't tell your dad either."

I could see Jack getting uncomfortable with the situation. It kind of made me feel powerful. I was being the cool stepmom wanting to have an open dialogue with my stepson. I let the silence hang for a bit before continuing.

"Have you ever had sex?"

He shot up at my question and I could see panic behind his faux anger.

"and if I had so what. I am an adult now and I can do what I want."

At that he stormed off back down to his room I figured. I stood there watching him go and figured I'd give him a few minutes to stew. I puttered around the house doing odd chores then I remembered the laundry and headed downstairs. Before heading to the laundry I stopped and looked at Jack's closed door. Mustering courage I carried the empty basket and knocked on Jack's door.

"Come in," he said through the door.

Slowly I opened the door and poked my head around the door.

"Are you still mad at me?"

"I wasn't mad at you," he said while sitting up on his bed, "I just I don't know."

I entered his room and sat the basket down and sat at the foot of his bed.

"I'm serious about not telling your dad. Whatever you tell me stays between us."

He seemed to war with himself before finally saying, "we broke up because I wanted to have sex and she didn't."

"Ok I understand," I said, bringing my leg up to sit on the bed. "I assume she was a virgin. Are you?"

My heart was beating faster. Why was it so important that I knew if he was a virgin or not?!

"yes she is no I'm not," he said and I sighed like a big weight left my shoulders.

"Well it's a big step for girls to decide to have sex. There is more stress involved. It's a lot of pressure. I'm sure she's just scared and it's not really about you."

"Do you think so?" He asked with those puppy dog eyes.

"sure. Hard as it may seem to believe but I was once a teenage girl too." I chuckled.

"When did you lose your virginity?" He asked which took me by surprise.

"oh um well I was younger than you. I was 16 and he was 18. I guess I always had a thing for older guys," I chuckled, giving him a pant on the foot.

He gave a polite smile but I think he looked alittle crestfallen at my joke.

"hey you are a handsome young man she'll come around. And if she doesn't you'll make some lucky girl really happy."

I tried not to but I glanced at his crotch when I said that, knowing that I meant his big dick will make some girl very happy.

"Thanks," he said, seeming to brighten that, "it's just hard, you know? We have done other stuff and now that we're broken up... " he trailed off but I caught his meaning.

Now that they weren't together he was having to take control of his ship himself now.

"and that brings me to why I came in here," I brought up the laundry basket, "I don't think it's a good idea for you to use socks to finish yourself in."

His eyes glanced over to the nightstand where I saw a sock sitting on it.

"I uh I don't know what you're talking about," he stammered uncomfortably.

I stood up and walked around the bed to his nightstand and went to reach for his sock but he snatched it up before I could touch it.

"oh I think you do. I found your other sock in the laundry earlier."

"I'm sorry it won't happen again."

"I'll be honest with you, it was quite impressive."

He looked at me confused.

"your socks are not small and that sock was soaked through. How many times have you used that thing?"

"Um, just the once."

"That is impressive!" I exclaimed before I could stop myself.

"really?"

I reached my hand out to take his sock and he kind of looked at me confused again.

"I gotta wash it, don't be silly."

He surrendered the sock and the moment I touched it I felt the familiar sticky slim of spent jizz. It was soaked through as well.

"Oh my god Jack! It's soaked!"

"I know I'm sorry."

"No no you misunderstand. It's kind of hot."

"Really you think that's hot?"

"Well not the sock full of jizz but the sheer volume of it sure."

"Look if you are going to masturbate, can you please do it in a cup or hell a condom if that's not too weird. If I mix loads of laundry I don't know that I want to throw your socks full of cum in with my clothes. You wouldn't want my nice white blouses to get all cum stained now." I winked at him and put the sock in the basket.

His face got bright red as he clearly thought about it.

"Right right of course yeah."

"Thank you so much. Look how much you normally masturbate?"

"Um well lately it's been like...3 maybe 4 times."

"a week?"

".... A day."

"You can do that 3 or 4 times a day?!" I tried not to sound so incredulous but it was hard.

He held his head down, averting his eyes. I brought my hand down to his shoulder.

"that wasn't judgment. I just didn't think guys could do that. Your father...well you probably don't want to hear about that. I uh I'll go get you a cup. Then when you're finished it can be washed and there isn't much to clean up."

I quickly turned away and practically ran up the stairs. I was nearly hyperventilating. I was still holding the basket and when I noticed it I realized I still had the cum sock. Realizing Jack was waiting for me I quickly put the basket down and searched around for a cup that said cum bucket. Finding a wide brim plastic cup I grabbed it and went back downstairs.

I knocked on Jack's door and at first he didn't answer but then he said I could enter. Opening the door I noticed he had a sheet over his lap and his laptop on his lap. I presented the cup and sat it down next to him.

"Hopefully this can work for you. When you are done with it next time just I don't know let me know and I can wash it. If not, I can always get you condoms. Have you ever bought condoms?"

Jack stammered, "um no I haven't."

I looked at him and put my hand on his shoulder so he looked up at me.

"Honey, you really should wear condoms when you have sex."

"We tried but they didn't fit." He looked back down.

I took my hand away from him and tried to do my best clueless impression.

"Are you sure you were putting them on correctly? Let me go get you one and I can show you how to put it on correctly," I was walking to the door as I said, "I think I have a banana still I'll be right back."

Before Jack could articulate a response I was already gone and heart pounding I ran up stairs and searched for one of my husband's condoms. I knew it was going to be too small for Jack but I had to play the game didn't I? I ran back downstairs and this time when I knocked Jack quickly replied. As I entered I held up the condom and a banana.

He started to say, "I don't think... "

"I understand that this might be really awkward but I'm serious, it's no problem at all. It's just education. I want to make sure you are ready when you are with a woman."

12