Mother's Boyfriend

CW: The same man is having sex with both mother and son. This story is from the son's perspective, hence this category. But straight sex is implied here.

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Before you judge her, let me tell you that my mother was not like this before. She was completely head over heels in love with my father ever since I remember. And always loyal to one man. Those two have been and always will be my idea for what a proper couple should be like.

Although I quickly learned that I would rather be with men; I have seen what a healthy and mature relationship should look like. It was Richard and Mona Simmons, my parents.

The problem started when my father died in a freak accident. I would never forget the day. I had turned eighteen only a month ago. My father was only forty five at the time of his passing. Any plans for going out to college was thrown away.

I started on a job a month after dad's passing. I was working hard to put food on the table. But the rent was being paid from my father's savings. My mother was a shell of her former self.

Nine months' after dad's passing, mom started working on two jobs at once. I told her that she didn't have to work that much. She was working too hard, and I feared for her health. She then informed me that along with the hospital and funeral cost, we had already spent half of what dad had saved for the future.

I didn't argue with her too much after that. Both mom and me would be out of the house early in the morning. Whereas I would be home in the afternoon. And mom came home really late, completely exhausted.

I wanted to protest. I wanted to say that she was putting her health at risk. And we did not need to do this. We are not that poor. We could borrow money from relatives if it comes to that. But I didn't say any of that. Because deep down, I knew that she was not working only for the money. She was trying really hard to keep herself busy.

Our relationship had turned into that of two roommates living in an above average apartment.

--

I knew I was gay ever since I watched porn for the first time. I don't know what made my parents give me the name Riley Simmons. I sometimes assumed that one look at me told my parents that I would be taking hot dicks up the ass. So they named me aptly. And they were not wrong.

Having the place to myself for more than six hours every day was an advantage. I could easily host for my grindr 'dates'.

I was not having sex every single day of the week. But I did have someone over at least twice a week, maybe more. I mostly used my own bedroom for sex, occasionally fucking in the living room or the kitchen. Every one of the men coming to fuck me knew that I share the apartment with two other people who will be back in a few hours. It has worked pretty well for me.

My sex life was varied. There have been men who I have invited to my place more than once. Despite having sex with many men, I only exchanged contact information with only five of them. I only kept their number if they were really nice or really really good in bed.

--

A few months after mom starting her work, she brought a man with her at our place. It shocked me a little, but I didn't say anything. That man left the next morning I never saw him again.

My mother was still only forty-two. She always had a perpetually exhausted look on her face. But she was still really pretty, and had an attractive figure.

Then it started. Mom started bringing men in pretty regularly. I assumed she was also using dating apps for hooking up. She knew I was gay, but I was able to hide the men I brought home.

--

On a fateful day, my life changed forever. It happened when my mother brought a man with her that had sex with me in the very apartment. He was an older man who called himself Carlos when he first came inside the apartment a month ago. Needless to say, he also came really deep inside me as well.

He was one of the best fucks I ever had. But I didn't exchange numbers with him, on account of him being a little too brutish. I like getting it hard and rough. But he was only that, hard and rough sex, and not much else going on with him.

Now I knew why he acted the way he did when he was with me. He was just a top that wanted someone to fuck at that time. He probably still was straight on the outside world. Hell, he might be one of those homophobes you meet that secretly had sex with men.

His eyes lit up when he saw me. He asked my mother who I was. My mother told him the truth. He then greeted me and told me that his name was Jacob.

That night, I went to bed thinking about the man fucking my mom. I knew exactly how rough he could get. And I imagined him doing that to my mother. It felt weirdly arousing at that moment. And yes, I am ashamed to admit it, but I masturbated before sleeping that night.

The worst part of all of that was that the man actually had breakfast with us the next morning. He told me that he was a colleague of my mother. They had started dating a few months ago.

A shiver ran down my spine realizing I would be seeing this man regularly now.

Then I looked at my mother. Jacob said that they had been dating for a couple of months. Mom had another man over only a week ago. Then I looked at the man. He fucked the shit out of me less than a month ago.

The man gave me a smirk before grabbing mom's hand.

"We are taking it slow." He said.

--

A week after that day, I found Jacob completely naked in the living room as soon as I walked in.

"Riley!" He addressed me. "Come over here and sit down with me son."

It felt wrong to hear him talk to me like that. It had been fifteen months since my father passed away. And I didn't want anyone to call me son ever again, especially the man sitting naked in front of me.

"Why the fuck are you naked?" I questioned his audacity.

"You know exactly why." Was his even more audacious answer. "Come on now."

Him being a brute and an asshole aside, you need to know that he is one of the best fucks I have ever had. I had sex with more than forty people. And he was, maybe the best one. Was it because the sex was still too fresh on my mind? I don't know.

All I know is that I was not strong enough to resist the magnificent dick in front of me. I kept glancing at it when Jacob stood up and led me to my room. Then he took me to the shower.

I was on my knees in less than five minutes. Instinctually, I opened my mouth and started suckling on his dick. It was a novel experience. I liked taking my time and licking the dick from tip to balls. Then he fucked my throat for ten minutes before cumming on my face. He then walked out of the shower and told me to carry on with my day.

--

That night, Jacob prepared dinner and greeted my mother on the door with a kiss on her cheek. She let her shoulders down and smiled when he kissed her.

I could not believe the audacity of the man. He asked me about my job during dinner. He asked me how I was handling working under people. The conversation was full of innuendoes. At one point, he said that he would love to work on top of me.

My sweet mother was probably too exhausted to catch any of the hidden meanings. Or if she did, she didn't want to call him out.

Once again, I imagined that man fucking my mother while masturbating.

The next day, I walked home to a naked Jacob once again. This time I blew him near the kitchen table.

He was standing right in front of the door the day after that. I just put my bag down, closed the door and got down on my knees. This time he came down my throat.

As I got up, I asked him how he could be so careless. How he could be so confident that my mother would not show up at any moment. She had another job, but she could just get walk in anytime and catch him with his dick down my throat.

He told me that he came home after dropping my mom off at her second job.

I asked him if he was moving in or not. He shrugged and said that he had pretty much moved in already. He said he had two absolute sluts at his disposal, mentioning that he had hit the jackpot.

It stung a little to hear my mother being called a slut, but if he fucked her like he did me, I knew it was inevitable.

--

Jacob was not waiting for me in the living room the next day. I felt a little relieved, a little anxious, and a little sad. Maybe he was out on a date with mom. Maybe mom would be home sooner, and he wouldn't be able to manage our time together. Or maybe he found another ass or pussy to satiate his dick with.

All those thoughts were running through my head when I walked inside my bedroom. There he was. Completely naked on my bed, sitting with his back against the headboard.

I sighed in relief before quickly undressing. As I crawled on the bed with my mouth salivating for the dick mere inches away from my face, Jacob stopped me. He threw me a tube of lube and commanded me to fuck myself. I was a little disappointed to not be able to put the dick in my mouth.

I quickly obeyed his command and started riding him cowboy. He then brought out a cowgirl hat from the side of the bed and told me to put it on.

I had to keep one hand on top of my hat to keep it from falling over while I was riding dick. I collapsed on top of his body as both of us came at once.

Jacob then carefully pulled the hat away from my head and informed me that it belonged to my mother. Then he made an offhanded comment that my mother was a total freak in bed.

Coming down from my orgasmic high, I felt something pushing deep down my chest. As if I was having a hard time digesting the information.

He then had me lick my cum off of his chest before taking a shower together.

--

The floodgates were completely open after that day.

He started having sex with me whenever he wanted. We started doing it in every single corner of the house. I was becoming completely subservient to the man. And he knew it too. He had started pushing my boundaries ever so slowly.

The first boundary broken was having sex on my mother's bed. We did it together and I had to hastily change the sheets before mom came home. Then we had sex plenty of times in her room. Then one day, he pushed my face against the window and fucked me there. We lived on the sixteenth floor of the building, but it still felt like I was being shown off to the world as Jacob's sex object.

Then we started showering together in my mother's washroom. It was slightly larger than mine, and there was a small place to sit down. It was probably there for you to sit down and shave your legs and whatnot. Of course Jacob had me sit on it for a better vantage point to fuck my throat.

Everything was getting riskier by the day. He was intentionally fucking me longer and slower. Edging me until my mind and body was completely melting. One day, mom came home right as he came down my throat. Luckily, we were doing it in the living room. I would definitely be caught if we were in her room.

Jacob pushed me behind the couch and pulled his shorts up. He was standing only in his shorts when mom walked in. I was lying naked on the ground. I heard them flirting then. Mom asked him where I was. He lied and said that I had already had my dinner and went to bed early.

Jacob called mom a horny little slut a minute later. Mom moaned in response. I assumed that mom started rubbing his dick over his shorts. It was still quite big even after ejaculating so soon. They then walked away to take a shower together.

The worst of it all was when he just walked in my room in the middle of the night once. I woke up when I felt a gust of wind all over my body. He had pulled away the blanket. I always slept naked with a cosy blanket wrapped around my body.

As I looked up, I saw a naked Jacob examining my sleeping body. I yawned and slowly got up to see his dick completely hard and wet. I assumed he was masturbating and needed help. I went forward to grab it. he quickly grabbed my hand and told me to put it in my mouth. Hands free blowjob was not a new thing for me, so I obliged.

It didn't taste that different than the hundreds of times I had sucked him off before. It was just a little wetter than normal. I worked my magic and slowly started taking his dick deep down my throat. I had my eyes closed with my hands behind my back.

I had gotten so used to blowing him that I knew when he was going to cum by his moans. And I knew he was close. He came deep inside my throat, depositing his load straight to my stomach. As I was still gently licking around the tip of his penis, cleaning him thoroughly; Jacob mentioned that my mother came all over his dick only minutes ago.

My eyes widened up and I looked straight at him. He was not laughing at me. But his eyes sure looked as if they were. He knew what he had done. The tip of the dick still in my mouth, he asked me if I had to say anything about that.

I popped the tip out of my mouth and thanked him for making me taste my mother so intimately like that. I don't know what came over me at the point that made me say that. But it was at that moment, I knew that he had completely conquered me.

--

I didn't realize it in the heat of the moment; but the door to my bedroom was slightly ajar. And my mother was masturbating to the scene of her only son sucking another man's penis.