dirty_boy69, Author at NSFW story — Page 5 of 21

My Secret Part III [M35/F40/F42] [Chastity] [Anal] [Lesbian] [Toys]

*The parts I and II are* [*over there*](https://www.reddit.com/r/dirty_boy96/comments/y7w1bc/my_secret/?utm_source=share&utm_medium=web2x&context=3)*. I advice you to read them first. Enjoy your read.*

After arriving in the bedroom upstairs, my wife ordered me to kneel down in front of the foot end of the bed. She ordered me to stay there and watch. Watching her and my boss making out with each other. Watching two hot women fucking each other.

My wife trained me well, so I followed her order without any hesitation. Totally ignoring my urge to join them in. Totally ignoring the desire to beg them to unlock my limp and useless dick to be able to get hard again. To be able to stick him inside both of them.

At least they allowed me to watch. She could have ordered me to stare at a bedroom wall two. Only able to listen to their fucking noises. Desperately trying imagine what they were doing.

My wife and my boss wasted no time. As soon as they were on the bed, as soon as their bodies touched, they began to kiss each other. Gentle kisses to warm up. Passionate kisses soon after. While kissing, they slowly undressed each other. They freed their hot bodies from their dresses. Read more »

My Wife, The Police Officer [M31/F34] [Caught] [Ball Busting] [Pegging]

Yes, you have read right. My wife is a police officer. And she is one since she was old enough to be one. She loves her job, and I love her. We are married for about one year right now. We ran into each other, or she ran into me about three years ago. She caught me in the act back then. Back then when I was thirty one years old and she was thirty four.

My story, our story began as mentioned above about three years ago. It was on a very foggy fall evening. Early evening, it just got dark and the fog was setting in when I was driving along a country road to get to my destination, a small town in the middle of nowhere. I had to get there, to do some business. I was on my way visiting a local agricultural machinery dealer. To sell him the newest products of my company. To convince him that it was the best stuff we ever made. To convince him that everyone needs the newest version of our plows. Read more »

Our Babysitter, The Trap [M37/F35/F22] [Trap] [Caught] [Threesome] [Anal]

My wife and I are hard working people in our mid thirties. We want to get somewhere in life. We wanted to achieve something. So our work days tend to be long ones. We often have to attend to work related events in the evening. So we often hire a babysitter to take care of our children. To prevent them from starving or dying an incredible stupid, totally pointless accidental death.

Our babysitter was working for us for about two years back then. She was a twenty two year old, good looking and smart college student that always took her time to look after our offspring. Because she needed the money. We paid her more than just well. Because finding someone you can trust to look after your children, not a that easy task to do.

When at work, when she was over at our place, looking after our children, she had the usual tasks to full fill: Feed our three children, wash them and make sure that they went to bed. Once the three monsters were asleep, she was allowed to do whatever she wanted in our place. Well, organizing a wild college party at our place was no option, but I think you know what I am trying to tell you here. Read more »

My Landlord Part VIII [M34/F65] [Blow Job] [Pussy Licking] [Vanilla]

*I really advice you to read the previous parts first. T*[*he parts I-III are over there*](https://www.reddit.com/r/dirty_boy96/comments/xut9ur/my_landlord/?utm_source=share&utm_medium=web2x&context=3)*,* [*parts IV-VI are over there*](https://www.reddit.com/r/dirty_boy96/comments/xuwm4g/my_landlord_ii/?utm_source=share&utm_medium=web2x&context=3) *and* [*part VII is over there*](https://www.reddit.com/r/dirty_boy96/comments/y73api/my_landlord_part_iii/?utm_source=share&utm_medium=web2x&context=3)*. Enjoy your read.*

About half a year later I still was with my landlord’s daughter. We had a very serious relationship up and running. I moved in with her. I knocked her up, and that slowly began to show. We were still fucking each other’s brains out. And I got along well with my landlord. Yes, she still somehow was my landlord, not just the mother of my girlfriend, because the place I lived in with my girlfriend, her daughter, was owned by her too.

My landlord was nothing but happy when we broke the news, when we told her that she was going to be a grandma soon. But she made a joke upon it: “Am I really looking like an old lady now?”

I jokingly shook my head, and told her that she still was good looking, gorgeous and was giving me a raging boner as soon as she began to show off. A very very happy smile appeared on her face, she even blushed a little bit: “Thank you.” Read more »

My Secret Part II [M35/F40/F42] [Chastity] [Ball Busting]

*The first part is* [*over there*](https://www.reddit.com/r/dirty_boy96/comments/y7w1bc/my_secret/?utm_source=share&utm_medium=web2x&context=3)*. I really advice you to read it first. Enjoy you read.*

It was Friday afternoon, about a week after I had the honor to serve my female boss for the first time, when it knocked at the door. I was in the kitchen when I heard it knock. I was busy cooking a feast. But my wife wasn’t ready yet. She still was in the bathroom, putting on some make up, making her hair or dressing up herself. So I had to open the door. I had to leave the hot pots on my stove unattended. Something I clearly didn’t wanted to do.

So I ran over to the entrance door and opened it up. It was her, my boss. She showed up on time. Something that normally isn’t happening anymore. She was dressed to impress. She caught my eye. And she smiled at me. She checked me from tip to toe. I was wearing nothing but a kitchen apron with some hearts on it. And my chastity cage. Well, the cage was hidden behind the apron, but it was there. Believe me. Read more »

My Secret [M35/F40] [Chastity] [Pussy Licking]

About a year ago, she came into my life. She was hired by our boss to be our new boss to push our productivity to the next level. She was about forty years old. She was a total tough nut. But she always was dressed to impress. She loved the attention she got out of it. And she loved staring at the bulges she gave her male coworkers. It just was her thing to do. It was her kink.

But she stand no chance with me. She just wasn’t able to pull the stunt. My thirty five year old cock didn’t want to get hard. Sure, I was looking after her. I wished to fuck her, like nearly every other man in our factory, but there was no boner between my legs. My dick stayed limp. And that drove her insane.

She saw my limp dick as a challenge. A challenge she wanted to pass. So she gave me a special treatment. She offered me views down her cleavage, she bent over without wearing panties, she did everything to get me hard. And believe me, I was lusting for her. I wanted her. But my dick, my dick stayed limp. Read more »

My Landlord Part VII [M34/F29] [Vanilla] [Breeding]

*I really advice you to read the previous parts first.* [*The parts I-III are over there*](https://www.reddit.com/r/dirty_boy96/comments/xut9ur/my_landlord/?utm_source=share&utm_medium=web2x&context=3)*,* [*parts IV-VI are over there*](https://www.reddit.com/r/dirty_boy96/comments/xuwm4g/my_landlord_ii/?utm_source=share&utm_medium=web2x&context=3)*. Enjoy your read.*

On the next morning, it was a Sunday morning, I woke next to my damn hot girlfriend, the daughter of my landlord. She was still snoring next to me when I opened my eyes. The second thing I realized after waking up – my girlfriend is always number one, or at least in most cases – was the perfect example of morning wood between my legs.

A boner that was hard enough to drive nails into walls. A boner that I didn’t wanted to go to waste. At fist I was thinking about jerking off, but then I turned myself around. I spooned the woman next to me. I gave her some gentle kisses on her neck. I pocked her with my hard one. To wake her up, and hopefully to fuck her.

Not even a minute later she opened her eyes. Without turning around, without even looking at me, she said the following, still half asleep: “Pull down my panties. Stick it in. Dump your load inside. And make my body tremble, make me moan out loud while doing so.” Read more »

The Bet [M27/M24] [Trap] [Roommate] [Blow Job] [Anal]

Roommates. We all love them, we all hate them. Most of them tend to be nothing put a big pain in the backside. But there are those rare ones, those you really get along with. And I had one of them, a couple of years ago. I was twenty three years old, he was twenty six years old when we first moved in together.

We shared a relatively big flat. Each one of us had an own room, we had a kitchen, a living room and a bathroom. We rarely ever argued, we shared cleaning duties, and it worked, we had something to talk about. We sometimes cooked for each other, and we loved to enjoy a drink together while having your typical male to male conversations.

We were living together for about a year when we were sharing a late afternoon drink in the living room. We were talking about this, we were talking about that and then the topic, the conversation moved towards woman. And well, all of a sudden, out of thin air, my roommate made made one comment. He did it in a very jerky, arrogant and confident way: “Those traps. Nothing easier to than to tell the difference between a trap girl and a “real” girl.” Read more »

My Roommate, The Sissy [M22/F22] [Sissy] [Roommate] [Anal] [Caught]

There is point when it is enough. When you have to stand on your own feet. When it is time for you to leave your family home and get a place on your own. It was a few years ago when I made this decision. But rents were already through the roof back then, so I needed a roommate to be able to afford anything. I came up with the great idea to ask a long time friend of mine, who was about twenty one years back then, to move in with me. Luckily it didn’t took much to persuade him to join in, because he had exactly the same problem like I had.

After some searching – it actually was nothing but a big pain in our backsides – we found an affordable, surprisingly big place for the two of us: A room for each one, a kitchen, a big living room and a bathroom. We immediately turned it into our man cave. Or better said, into our party hub. We did what you do when you move out from home when you are in your early twenties: Lots of drinking, mixed with loud music and fucking everywhere. Luckily our neighbors were forgiving. Or never home. Or just deaf. We never had any problems with them back then. And we still have no problem with them until this day. Read more »

Night Shift [M35/F35] [Trans] [Hand Job] [Anal]

I am clerk at a local gas station. I have that job fore about a decade. I drag my thirty five year old body to work on five, sometimes six days a week. But I always go to work when it is dark outside. I work graveyard, I work the night shift only, because it is my thing to do. I love to work when it is dark outside. I love the silence of the night, and yes, I like the people that show up too.

And no, I haven’t said goodbye to sunlight: After my shift I often go out, into the sun, some hiking, some chilling, enjoying the quiet of the morning, while everyone else drags their sleep drunken bodies into work. I love my ultra night owl lifestyle, but finding a partner that shares it with you, is a very tough thing to do.

My shift starts at about nine thirty in the evening, and it ends around six thirty in the morning. When I arrive at work, I make a round around the compound, to check out if everything is alright. Then I take over the cash register from a coworker, then I end my coworkers tend to have some chit chat, then they leave. They leave and leave me alone in the dark. Read more »