Author: dirty_boy69

My Landlord’s Daughter [M34/F29] [Pussy Licking] [Vanilla]

After I exchanged contact information with my landlord’s daughter on my landlords party, after I had promised my landlord to call her daughter it took me until Monday to send her a first message. It just was a casual “Hi, how are you? Do you even remember me?” one. Luckily she remembered me. And luckily she got back to me.

We kept on texting back and forth for a day or two. We still got along and had something to talk about. So that thing we had up and running at her mother’s party wasn’t just a one time lucky hit. So I asked her for a date. She said yes. We agreed on Friday night, in one of the fanciest Italian restaurants in town. She chose the location. She insisted on it.

Her insisting on it gave me a minor heart attack. I clearly couldn’t afford it. And getting a reservation in one of the most popular restaurants in town for a Friday night on a Wednesday afternoon, it gave me more than just a headache. Read more »

How I Turned Myself Into A Perfect Sissy [M21/F26] [Masturbation] [Sissy] [Roommate]

Meanwhile I am a perfect Sissy. A next to perfect fuck toy. A cum dump, the sluttiest slut out there, but I wasn’t always that way. I wasn’t always what I wanted to be. My transformation began about three years ago, when I moved into a new place. When I moved into her place. I, or better said we had no clue on what an awesome journey the two of us would go together. And what an awesome bounding would come out of it.

In the beginning, I was twenty one years old back then, my roommate was twenty six, after moving in, it was your usual you move into a new apartment with a person you don’t know situation. We had a few drinks together from time to time to get to know each other. We had the usual who does what in the household fight. And we generally speaking, we hat to get used to each others presence.

But we grew closer more than just fast. The fact that I was a man and she was woman didn’t really mattered for the two of us. We got along, we found out that we had a lot in common, we began to spent more and more time together. And we more and more got comfy with each others presence. Read more »

My Landlord [M34/F61] [Pussy Licking] [Vanilla]

A couple of years ago thirty four year old me had to move out of his old place. A very painful and mess breakup was the reason why I had to leave my home, a place that I had shared with my now ex girlfriend for about ten years. Yes, it did nothing but hurt. And it all sucked ass.

The apartment was owned by my exes father, so I had no chance to sue myself into staying and getting her out. It took me a few sleepless night on the sofa to accept that fact. But luckily my ex was a reasonable human being: She gave me two months after the breakup to find something new. But she also told me, that earlier would be better.

So two, maybe three days after my world broke into pieces I turned on my computer to search for a new place to stay. After browsing the web for about ten minutes I quickly realized that the rents in the city I lived in went through the roof since I was apartment hunting for the last time, about twelve years ago back then. So a big apartment in the best district, just not doable. But something decent sized in a less cool part of town, doable. Read more »

My Former Teacher [M34/F49] [Hand Job] [Teasing]

Summer time is lake time. As soon as it is warm enough, as soon as the summer is showing up, the whole town I life in more or less moves over to the lake next to our town. Everyone spends as much time as possible over there: Chilling in the sun, swimming, hanging out with friends or having a BBQ. It just is the place to be as soon as the weather turns fine.

On one ordinary Saturday during the last summer thirty four year old me was chilling at the lake. I was reading an entertaining book, when all of a sudden she showed up. She was about fifty years old and immediately caught my eye. She had my full attention from the moment she came into my field of view.

While she came closer I thought that I knew her from somewhere, but no matter how hard I tried, I wasn’t able to figure out from where I knew her. When she was next to me she asked me if the place next to mine was already taken.

I gave her an honest answer: “No, no one has taken the spot.” Read more »

My Yearly Checkup [M44/F33] [Femdom] [Anal]

Some time ago it was time. The time of of the year. Time to something I never was looking forward too: My yearly physical. Once a year I head over to my doctors office to give myself a proper checkup. To see if my body is still up and running. And to please my insurance.

The last years checkup was the last one with my old doctor. He was an awesome physician, he had humor, we got along with each other when we were dealing with each other. But on our last get together, I was visiting his office for a few stitches, to close op a cut, he told me that he had enough of the daily grind. He loved his job, but he was retiring.

It didn’t really took me by surprise, because he wasn’t the youngest anymore, but it still bothered me. Because finding a good doctor, it is a tough thing to do. But after he told me that he’d retire, he also told me that his daughter would take over his office. And that I might give her a try. I followed my doctor’s advice. Read more »

My New Swimming Pool [M35/F64] [Mature] [Pussy Licking] [Vanilla]

During the last winter I came up with an awesome idea: I am going to build a swimming pool in my backyard. For my children when they are with me during the weekends – yes I am a divorced father – and for the whole neighborhood during week days. Especially for those hot stay at home moms that were around. During the days their kids would be out in school, their husbands would be at work and they could come over and chill in my backyard, next to my my private swimming pool. Looking good while doing so. Bringing some excitement into my home office days.

Luckily I have the money to afford such a project. So I went down to town hall, I filled out a shitload of paperwork, I hired someone to plan it, I hired a contractor to actually built it and then I spread the message. Luckily everything went according to plan. I had my pool before summer really kicked off. Read more »

My New Female Boss [M35/F40] [Chastity] [Teasing] [Pussy Licking]

About a year ago, she came into my life. She was hired by our boss to be our new boss. Her main task was pushing our productivity to the next level. And yes, she turned us into a faster and more efficient work force.

Back then she was close to forty four years old. She was a total tough nut. But she was always dressed to impress. She loved the attention she got out of it. It was her hobby, her personal mission to give every male human being in the building a raging boner. She loved staring at the bulges she gave her male coworkers. A huge smile appeared on her face as soon as she achieved her personal goal.

But she stood 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. Read more »

The First Day On The Train [M28/F26] [Transgender] [Anal] [Romance]

Trains are my thing. Since I can remember. I have always been fascinated by them. So I spent the bigger part of my free time – no, I wasn’t working for a railway company, I spent my time in a research lab working on ways to safe the environment – on trains, in railway stations or looking at trains in some rail yard.

I was perfectly happy with my job and my life. But it lacked one thing: A significant other. A girlfriend. A woman on my side. It took until I was around twenty eight years old to find a suitable partner. And this here, is the story how I met her, or to be totally honest with you, how I got hooked up with her.

It all took place in the middle of the fall. About six years ago. I was spending my weekend on a steam powered train that was doing a trip through the beautiful autumn colored landscape. I was more than just looking forward to it for months. I even bought some new camera gear to get better shots of the train, the landscape and the people on the train. Read more »

Caught Jerking Off [M31/F34] [Femdom] [Masturbation] [Ball Busting]

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 a 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. So what happened back then? How did my wife and I got together?

Three years ago I was a traveling salesman. I was selling agricultural equipment to resellers. So I was practically living on the road. Because I loved my job and because I wanted to make as much sales and as much money as anyhow possible. As you can imagine selling agricultural equipment isn’t bringing you into the big cities. I spent my time traveling around in the country side. From one small town to the next one. Always trying to convince the local agricultural equipment dealer to buy some of the newest, fanciest and most expensive machinery my company was producing. Read more »

Caught Watching Porn [M28/F27] [Roommate] [Masturbation] [Hand Job]

Back when I was twenty eight years old I shared a place with some twenty seven year old roommate. We two knew each other before we moved in together. No we were not best friends, just friends of friends. And it was through those people we both knew that we landed in the same place. They hooked us up, so to say.

My future roommate was looking for a new person to share her flat with because she didn’t get along with her former roommate anymore. They were arguing all the time. The air just was out. And I was looking for new place to stay because of some similar reasons. I couldn’t stand the sight of my roommates anymore.

So what do you do when you look for a new place, or a new roommate so that you don’t loose your place? You tell your friends that you are looking, you ask them if they know someone, and so on, and so on. In the end a friend of mine gave me her number. Then I send her a message, we set up an appointment and I visited her place, my new home for the first time. Read more »