Author: dirty_boy69

A Sissy Takes Off [M34/F25] [RimJob] [Anal] [DeepThroat]

Shortly after the first professional shot pictures of my sissy girlfriend went online the inboxes were filled to the brim. Most of the messages were horny men asking for more a pictures, telling my girlfriend that they wanted to fuck her or just were saying something pointless like hi or hey. My girlfriend clearly liked the attention she got. The compliments made her more self conscious. It all made her hungry for more.

Luckily there were some serious job offers buried beneath all the spam and horny messages. Some people actually really wanted to book my sissy girlfriend for a photo shooting for their businesses and web pages. Due the fact that I had more experience with business things – thirty four year me had seen a fair share of negotiating in his life – I handled the requests.

Most of the requests led nowhere: The first conversations went silent when I told the potential customers that my girlfriend wasn’t available for erotic or pornographic shootings. The next, and the by far biggest part of requests dropped when I told them that some sort of compensation has to be made. Read more »

The Old Mansion [M32/F51] [Femdom] [JOI] [Masturbation]

Working as a headmaster, it just is my dream job. I like doing minor repair works, I like taking care of a garden or some lawn. I even like doing some cleaning work in hard to reach spaces. And I love that I mostly work without any supervision, that there is hardly ever a boss breathing down my neck.

But it wasn’t always that way. Back then, when I left school, I learned a trade. I became electrician. I did nothing but wiring new buildings for about half a decade. At first it was fun, then it got repetitive and boring. While the pressure to get more and more done in the same amount of time constantly rose.

It took me a while to figure out a way out. I was browsing job descriptions, I was talking with friends and family, until one day I ran into someone drinking in the local pub. While sitting at the bar next to each other, a conversation came up and I asked him what his job was. Read more »

Falling For A Sissy [M32/F24] [Romance] [Sissy] [Deep Throat] [Anal]

Like most other people on our planet I have to go grocery shopping from time to time. It just has do be done. Not that I love doing it, but well, one thing that I like even less is starving. Or running out of snacks while hanging out in front of my TV.

To prevent such accidents from happening I headed into the grocery store not far away from the place I was living in. About two times a week, sometimes even three. Because stupid me tends to forget buying non essential stuff like canned tomatoes when planing to cook some pasta with tomato sauce.

I normally go grocery shopping on Tuesday and Fridays, always after work. I take a huge bag with me and on my way home I get some food supplies. But when I am on vacation, or when I have days off, I do my shopping in the late morning hours. Because there are by far less people are in the store and it makes grocery shopping a much more relaxing experience. Read more »

Meeting An Old Friend [M27/F28] [Transgender] [Trap] [Deep Throat]

Some time ago, I was twenty seven years old back then, an old male friend of mine texted me out of the blue. We hadn’t been in contact for more than seven years. So he somewhat took my by surprise. But it was a more than just welcoming one. As it always is when someone from your past drops in to check up on you.

We kept on chatting from time to time for a couple of weeks. It mostly was some remember back then chit chat mixed with some actual information about our current lives. It was nothing out of the ordinary, overall speaking it just was nice. And it grew the idea inside me to meet up for a cup of coffee or some ice cold drinks.

So I just asked him out. For a meet up, I clearly wasn’t planing hitting on him. Talking in person just is much nicer than texting. And I was curious about him. About his looks, about his everything, because I found nothing about him online. Not a single picture of him, nothing. He probably was one of those who liked to keep a low profile. Who wasn’t keen about sharing his face and his private life with the rest of the world. Who could blame him for being that way. Read more »

The Business Trip [M32/F56/M59/F30] [Femdom] [Spanking] [Anal]

When my alarm clock rang on that Saturday morning I was already out of bed. No drinking, no hanging out with friends for me the night before. I went to bed early. After reading the third reminder message the secretary had sent me. He really took his job serious. He really wanted me to be on that trip. So did I.

So after waking up I had some breakfast, then I went into the bathroom and then I got dressed. In some of the fancy looking new clothes I bought with the credit card that was given to me in one of the stores the secretary later recommended to me. Once my morning routine was over, it was close to pick up time. So I grabbed my stuff, went downstairs and waited for a few minutes.

Then a big black car stopped in front of me. The driver got out, told me that he would take care of my luggage and opened the backdoor of the car for me. I climbed into the open door and there she was. My girlfriend, my mistress and back then still my CEO. Read more »

My Mom’s Best Friend [F55/M32] [Mature] [Vanilla] [Romance]

My mom and her best friend were best friends since forever. It all began on the playground, when my mom ran into her future best friend after her family had moved into the small town my family was living in for generations.

Initially my mom and the other girl were beating the shit out of each other. But they began to get along, years passed, they spent their school years together, they went to college together, they became an inseparable pair of friends for the biggest part of their lives. Their relationship clearly stood the test of time.

Now, more than forty years later they still are best friends. Sure, they had their struggles, they were fighting over some men, they had times when they weren’t talking with each other at all, but in the end the two always got their shit together. And they had been there for each other when needed.

So my mom’s best friend practically knew me since the day I was born. When I grew up she was nearly always around – as mentioned above, my mom and her had their fights, their arguments too – when I grew up. On average I saw her at least once a week. And she was the one baby sitting me and my siblings when my parents went out on a date. Read more »

The Job Interview [M32/F35] [Femdom] [Spanking] [Pussy Licking]

Don’t we all have a dream job? A job we would do everything to get? Everything, no matter what someone asks of us? I for sure had such a dream job. A job I wanted since I can remember. And when the chance opened up to get my perfect job I did everything to seal the deal.

I did everything, no matter what they had asked me to do. Just to show them my dedication, to show them that I was more than just serious of getting that damn job. And to take away the surprise, in the end I got my dream job. But the last two steps towards it were unusual ones. Some very arousing but more than just unusual ones.

Back when I was around thirty two years old I was looking for a new job. I didn’t got fired in my old job, I just wanted something different, something a little bit higher up in the corporate ladder. And it had to be in one of those companies I was dreaming to work for since forver. Luckily one of my dream corporations was hiring the exact position I wanted. So I set up the best resume, the best CV I had ever written and then I sent it over to them. Read more »

How She Turned Me Into A Woman [M20/F44] [Romance] [Femdom] [Vanilla] [Masturbation]

Back when I was about twenty years old I was more or less living in a bar around the corner. I hung out there nearly everyday. I had a couple of beers with some friends, we played darts, we played pool or we watched sports together. And from time to time, I successfully hit on women that were hanging out in my bar too. But the only thing that came out of it was a never ending series of one night stands.

Every time some new female face showed up in the bar all single men, some of the taken ones too, jumped onto her. Everyone tried to impress her, to get her into their beds. To fuck them and maybe to fall in love afterwards.

One Friday evening an about forty four year old woman entered the bar. Everyone inside was preparing to make their move. But as soon as they saw that she was good friends with the man behind the bar, the owner of the bar himself was serving drinks that evening, they all pulled back. Better not messing around with the guy that serves you drinks and owns your living room. Read more »

My Roommate, The Sissy [M29/F22] [Sissy] [Toys] [Masturbation]

About two years ago my roommate left town. He was leaving the place we share for about five years. He had a job offer he couldn’t decline. So I had to look for a new person to share my apartment with, because back then I wasn’t able to afford it on my own. And I didn’t wanted to loose my home. Because it was affordable and I just loved living in it.

Many people showed up and took a tour through the place. Most of them weren’t down my alley. Of those who were some just didn’t want to move in with me. It just took some time to find the right new roommate. And luckily one day, he showed up.

He was about twenty two years old and something between him and twenty nine year old me just made click. He genuinely liked my place, he could stand me and so he asked me if he could move in. I told him that I needed some time to think about it, but about two hours later I sent him a simple message: “You can move in, if you like.” Read more »

Our New Neighbor [M44/F48] [Femdom] [Ball Busting] [Pussy Licking]

About six months ago someone new moved in next door. The old man that had lived in the apartment next to ours for over a decade had passed by. We were at his funeral, and we missed him from day one. Because he was the perfect neighbor: If I wouldn’t have run into him in the hallway from time to time, I wouldn’t even have noticed that he was there.

From the day we died on we were hoping that we will get a similar neighbor. Just someone that lives next to us and is invisible. And by far more important, silent. Because it just is relaxing when you don’t hear anything at home. Unless you turn up the TV, or the radio, or the vacuum cleaner.

The place staid empty for a couple of months. Some renovation was done, the rent went up and so it took some time until the landlord found someone for the place. We were not that disappointed that it took that long: The longer no one was living next door, the longer it was quiet. Read more »