Author: dirty_boy69

[MF] How I Turned Myself Into A Perfect Sissy [Masturbation]

I am a perfect sissy. Meanwhile. But I wasn’t always that way. I wasn’t always what I wanted to be. My transformation began six 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, after I moved into her place, 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 it didn’t took long until it happened. Until she caught me jerking off. It might have even been partly my fault, because I accidentally forgot to close the door to my room behind me. Maybe I wanted to get caught back then. Read more »

[MF] Meeting An Old Friend [Anal]

It all happened a couple of years ago. I was a 32 year old single man back then. So I spent lots of my free time in bars, at parties and in similar crowded places, looking for a significant other, a girlfriend, someone to share my life with. But nothing had really worked out so far. No real match had showed up.

Until one day, when she came in my life. She asked me if the place next to me was taken, I said no, please, sit down. Then I offered her to pay for her drink. She gladly accepted my offer. Then we began to talk. We had a connection. Something made click. From the beginning on I had the feeling that we knew each other, that we had met before. But I couldn’t figure out where and when.

We spent the whole evening together. Talking, downing a few drinks, sharing a few laughter, in other words, we had a blast. But that was all that happened on our first evening together. And yes, stupid me, forgot to ask her about her phone number. The last one was something that I really regretted during the following days. Yes, I wanted to see her again. Read more »

[FM] My Mom’s Best Friend Pt. II [Pussy Licking] [Vanilla]

*I really advice you to read part I first.* [*It is over there*](https://www.reddit.com/r/dirty_boy69/comments/x7e61v/my_moms_best_friend/?utm_source=share&utm_medium=web2x&context=3)*. Enjoy your read.*

After I fucked my mom’s best friend, she really asked me to help her with something. She wanted to rearrange her study. She needed my help to get her books out of her shelves, and then to move the shelves. And well, needless to say, that I was helping her out.

The whole operation took us a few hours. During it all we made a few breaks. We had some snacks, some coffee and figured out that we had something to talk about. We even shared a few laughs. When work was done, she promised me a reward. No, she didn’t went down on her knees in front of me and sucked my jizz out of my balls, that stuff came later.

When work was finished we said goodbye and I went back home. Back home to have dinner with my parents. When I arrived, they two were already sitting on the dinner table. As soon as the realized that I was home, the turned around, waiting for me to show up. They had a very particular look on their face. And some very, very decent smiles. Read more »

[MF] Helping Out A Neighbor Part II [Blue Balls] [Toys]

*I really, really advice you to read part I first.* [*It is over there*](https://www.reddit.com/r/dirty_boy69/comments/xgodm8/helping_out_a_neighbor/?utm_source=share&utm_medium=web2x&context=3)*. Enjoy your read.*

A few days later my upstairs neighbor texted me again. She asked me how I was doing, I asked her if everything was okay with her. And yes, we all know, when people do the stuff I have written down in the previous sentence, they tend to want something from you. So I just asked her, to shorten the conversation: “Is there anything I can do for you?”

The answer came a few seconds later: “As far as I know, and as far as I have seen on your Social Media accounts, you are good with photography. And we both know, I sell pictures and videos of myself. So do you want to help me out, to take a few pictures of me, and maybe film me a little bit?”

I didn’t had to think long about her over. She got the following answer back: “Yes, I’d love to help you out a little bit.”

Then we set up a date. We agreed on Saturday early afternoon, she also told me to not plan anything else on that day, because according to her experience, shootings tend to drag on forever. Read more »

A Cup Of Salt [MF] [Mature] [Pussy Licking] [Ass Licking] [Blue Balls]

One ordinary Sunday morning I was beginning to cook something. I checked if I had everything I needed and yes, nothing was missing. Well, except some salt. I could swear that I had enough the day before. Maybe some ghost, or one of my roommates had taken it. I was pissed for a few moments, then reasonable me kicked in: Maybe I just knock at my neighbors door and ask them, if they could spare some.

I began on the first floor and worked myself upstairs. For about ten doors no one opened up or they just didn’t bothered to share. I grew more and more desperate with every door. But then, finally, on the fourth and last floor, I hit gold.

One of my neighbors opened her door. I knew her from running into her in the hallway. She was in her mid sixties and was living alone. Her husband has been two decades older than her and had already passed away. She seemed to be nice. I liked talking with her when we ran into each other. So well, I hoped that she would spare some salt. Read more »

[MF] Caught Watching Porn Pt. IX [Masturbation] [Spanking] [Pegging]

[*Episodes I to V are over there*](https://www.reddit.com/r/dirty_boy69/comments/vifcax/caught_watching_porn/?utm_source=share&utm_medium=web2x&context=3)*,* [*Episodes VI and VIII are over there*](https://www.reddit.com/r/dirty_boy69/comments/wvb0f6/caught_watching_porn_pt_ii/?utm_source=share&utm_medium=web2x&context=3)*. I advice you to read them first. Enjoy your read.*

As hinted before, something had changed between my roommate and I. After our last time playing with each other, we constantly were seeking each others company. We hung out a lot in the living room, watching some shows on her laptop or just being in the same room, doing what soever. Despite the obvious sings we both pretended that nothing was happening. We played it cool. Downplayed everything we felt. At least for some time.

Meanwhile her online accounts were doing great. People were hot for her videos. People were hot for her pictures. So some new, more interesting content had to be produced. My roommate asked me, and her female friend, yes the one she fucked in the kitchen while I took pictures of them, for help. I said yes without thinking more than a second about it, so did her friend.

Then we brainstormed on what the scene should be about. About what the content should be about. After an hour, or maybe two, my roommate and I came to a very obvious conclusion: How about a roommate scenario. Roommate catches roommate, things get sexual. We both agreed upon that. We set up everything for the upcoming Saturday afternoon. Read more »

[MF] Helping Out A Neighbor [Masturbation]

Neighbors. Nearly everyone has them. Some have more, some have less. I have a lot of them. Because I am living in a very big apartment complex. And yes, most of my neighbors, I have never ever met them once since the day I moved in.

Then there are those you have contact with from time to time. I tend to divide them into three groups: Those that annoy the shit out of you. Those who just say hi when running into you. And those who talk with you. No, not about my relationship problems, but about what was going on in the house. Your classic neighborhood chit chat.

My neighbor from directly above me was in the third group. We even talked about ourselves from time to time. We shared some personal information. For example I knew that she was 39 years old, she knew that I was 34. We also talked about each others professions She told me that she was a corporate drone in home office, I told her that I was doing some IT stuff and was trying to get into some freelance photography. As a side hustle, because I really love doing it. And so on, I think you all know what I am talking about. Read more »

[MF] The Accidental Dick Pic Pt. 06 [Hand Job] [Anal]

*I really advice you to read the previous parts first.* [*Chapters I to IV are over there*](https://www.reddit.com/r/dirty_boy69/comments/vkqa1k/the_accidental_dick_pic/?utm_source=share&utm_medium=web2x&context=3)*,* [*Chapter V is over there*](https://www.reddit.com/r/dirty_boy69/comments/x7lgix/the_accidental_dick_pic_pt_ii/?utm_source=share&utm_medium=web2x&context=3)*. Enjoy your read.*

After we arrived at our destination, after we had some nice adult fun on the plane, my girlfriend – yes she is my mistress and my boss too – and I got in a huge car and we were driven to our hotel. Once we arrived at our destination we moved into our suite, refreshed ourselves and then we headed to the first of many boring business meetings on our first business trip together. Well, it was only boring for me, but very important and necessary for my boss.

To be able stay together during them all she turned me into her personal assistant and secured me a place at every meeting. I always was sitting on her right side. She also gave me a few orders, a few tasks I had to take care off: “Take notes of what people saying. Focus on personal information and what they are saying between they lines.”

I confirmed her orders with a nice and short: “Yes, mistress, I’ll do my best.” Read more »

[MF] My Former Teacher Pt. III [Pussy Licking] [Hand Job] [Pegging]

*I really, really advice you to read the first two parts first.* [*They are over there*](https://www.reddit.com/r/dirty_boy69/comments/x9wqe9/my_former_teacher/?utm_source=share&utm_medium=web2x&context=3)*. Enjoy your read.*

Monday morning, the third day of me being with my former teacher I woke up alone. She was already out of bed. So no reason for me to stay in bed anymore. I went to the bathroom, then I got dressed – she put a new set of clothes for me on a chair in the bathroom – and went downstairs.

While heading down the stairs I already saw her. Sitting on the sofa in the living room. Reading a book. While enjoying a cup of green the. Once she realized that I was in the room, she wished me a good morning. I wished her the same back. She signaled me that she wanted a kiss on her cheek. I gave her what she wanted.

Then she told me to make breakfast for the two of us. But she did it in a very nice way: “If you want some breakfast, make yourself a home. There should be plenty of food in the fridge. And when you are already at it, it would be nice when you’d make enough for two.” Read more »

[MF] My Landlord Part III [Pussy Licking] [Vanilla] [Deep Throat]

*I really advice you to read the first two parts first.* [*They are over there*](https://www.reddit.com/r/dirty_boy69/comments/wxc08b/my_landlord/?utm_source=share&utm_medium=web2x&context=3)*. Enjoy your read.*

On Monday, during my lunch break, I checked my inbox for the first time. Many people were showing interest in the places I put up for rent. I immediately called her, my landlord about it. She was more than just happy to hear that I already had about fifty requests queued up. She told me to give them her business phone number. To those who had already contacted me and to those who will contact me. Then, once more, she thanked me for my help, and told me that she already was working on a reward for me.

After that call, life went back to my normal. Working, hanging out with friends, trying to hook up with some girls, the stuff that single men my age do to pass time and to maybe leave the single team once and forever.

All in all, about two weeks passed until my landlord called me again: “You can put the postings down. All four places are rent out. Thanks for your help. And do you have anything planed, Friday late afternoon and Friday evening?” Read more »