Author: dirty_boy69

The Accidental Dick Pic [M32/F32] [Femdom]

*Beware: M32/F52. Damn fucking typo. Enjoy your read.*

Yes, it happened to me. I sent a dick pic to the total wrong person. I wanted to sent one to a friend with benefits, we both were into sending each other pictures like that, but it landed on my companies CEO’s phone. As soon as I realized that I made a mistake, I tried to delete the picture. But it was too late, it already got delivered. I had more than just a small anxiety attack back then.

You might ask yourself, how an average corporate office drone got the phone number off an CEO, here is the explanation for it: I once had the honor to serve as driver for the head of the corporation I worked for. The reason for it was that the actual driver was sick. He wasn’t able to get out of bed for two weeks. So a replacement was needed. And when my boss ask who has a driver’s license, I was smart enough to lift my hand. Read more »

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

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

The next morning I was the first one waking up. The two women next to my, my wife and my boss, were still asleep. I decided to leave them alone and went downstairs, to make them some awesome breakfast. Well after a visit in the bathroom, I took a quick shower, I cleaned my cage and brushed my teeth. And nope, I wasn’t putting on any clothes afterwards.

Down in the kitchen I threw some nice tunes on the radio and went to work. I prepared some fruits, I prepared some pancakes, I boiled some eggs and I brewed some fresh coffee. It must have been the smell of the coffee that woke up the two women. They came downstairs together. Dressed in some comfy sleeping clothes. The ended up in the kitchen, next to me. Standing in my way. So I told them to sit down next to the kitchen table. I also told them that breakfast would be ready soon. They did what I told them to do. Read more »

How I Turned Myself Into A Perfect Sissy Part V [M23/F26/M36] [Anal] [Deep Throat]

*I really advice you to read the previous parts first. They are* [*over there*](https://www.reddit.com/r/dirty_boy96/comments/xuwfq0/how_i_turned_myself_into_a_perfect_sissy/?utm_source=share&utm_medium=web2x&context=3) *and* [*over there*](https://www.reddit.com/r/dirty_boy96/comments/102bdix/how_i_turned_myself_into_a_perfect_sissy_ii/?utm_source=share&utm_medium=web2x&context=3)*. Enjoy your read.*

Time flies by. Especially when you look back onto your own past from a future point. After my roommate and I had produced our first more than just decent porn video together, the thing really got viral and made us a lot of money, my feminiziation kept on going. I kept on training my voice, I improved my posture, my movement with every week and I was planning of getting myself a nice pair of tits. And maybe some new fuller lips.

But surgeries like that don’t come for free. Or for cheap, when you want to make sure that you get the best, most qualified surgeons that are available. So I needed to make more money. My roommate, well, from that point on more my girlfriend, and I kept on producing content. Content that on average did more than just well. Our audience was growing. Not exploding, but the numbers went upwards not downwards. Read more »

My Virginity Problem [M31/F58] [Pussy Licking] [Vanilla] [Virginity]

Yes, I admit it it. I had a virginity problem. Until I was around thirty one years old. And nope, I was no unkissed virgin, but well, besides some kissing I had no sexual experience at all. I just struggled with that things. I was, and I still am, on the shy and introvert side. So talking to some woman was a next to impossible task for me. And well, due many failed attempts, I just threw in the towel. I gave up on having sex or finding a suitable partner.

To compensate for it, because horny still is a part of your life, even if you stop pursuing any sexual experiences with a partner, I began to watch porn. To watch a lot of porn. To jerk of at every possibility.

And yes, over the years I got addicted to watching porn. It got worse and worse, to a point were it really began to interfere with my day to day life. Luckily I was still reflected enough that I figured out that I had a problem on my hands. But it took me some time to make the first step, to actively do something against it. Read more »

My New Swimming Pool Part III [M35/F64] [Mature] [Pussy Licking] [Hand Job] [Vanilla]

*I really advice you to read the previous parts first.* [*They are over there*](https://www.reddit.com/r/dirty_boy96/comments/yq0lj8/my_new_swimming_pool/?utm_source=share&utm_medium=web2x&context=3)*. Enjoy your read.*

The days after I had an awesome threesome with my hot neighbor and her friend next to my backyard swimming pool, my streak of good luck came to an end. Summer was showing me the middle finger. The weather turned bad. Clouds were covering the sky for a few weeks straight. The temperature dropped – no, it wasn’t freezing, but not going for a swim hot either – and rain was pouring down nearly every day. Needless to say, my pool was closed.

All I did on weekdays was working, staring out of the window, viewing the weather forecast, hoping that the sun would make a comeback. And my neighbor would show up next to my pool again. In the best case accompanied by her hot friend. But it wasn’t happening. The weather stayed bad.

About a two weeks later I was seriously thinking about walking down the street, knocking at my neighbors door, doing some chit chat and then making a move on her. Hoping that she would be in it too. But knowing me, that just was a fantasy. A fantasy that I would never turn into reality. Read more »

The Elderly Woman From Next Door Part II [M34/F75] [Vanilla] [Pussy Licking]

[*Part I is over there*](https://www.reddit.com/r/dirty_boy96/comments/ywriy1/the_elderly_woman_from_next_door_m34f75_vanilla/?utm_source=share&utm_medium=web2x&context=3)*. I really advice you to read that one first. Enjoy your read.*

After our first fuck my neighbor and I kept on going. Whenever I was in the mood I knocked at her door. When she was at home, she opened up the door, we hugged each other, we had some chit chat over a cup of tea, or over a cup of coffee, it depended if it was morning, afternoon or evening, then we got closer to each other. And we fucked each other’s brains out. It felt like my thirty four year old dick was made for her seventy five year old pussy.

But it didn’t took long and the vanilla fucking got boring. It still came great for both of us, but the special something went away more and more with every fucking week that passed by. So we decided to turn up the kink. To try something new. And yes, we were looking for inspiration. So I came up with the great idea to watch some adult movies together. Just to come up with ideas. To my surprise, she said yes. Read more »

The Elderly Woman From Next Door [M34/F75] [Vanilla]

*Yes, it is not a total new tale. Just a rewritten one. Enjoy your read.*

My next door neighbor. She caught my eyes when I moved in the place. Unfortunately she was married back then. She was with her husband for about fifty years. They still were in love, and I could hear on occasion that they still were fucking each others brains out. Other than that, they were the perfect neighbors.

A couple of years went by. Me and my neighbor were chatting from time to time in the hallway. Sometimes it just was the two of us, sometimes her husband joined in. I liked them both. They were just a nice elderly couple living next to me, enjoying their live as good as they could: Yes, they were traveling a lot. They always told me that in their age, you got no time to waste.

But then fate hit hard. My male neighbor from next door got sick. He got cancer. It was devastating for his wife. And it didn’t went by me, seeing him getting worse and worse every time I ran into him in the hallway. I offered them my help, they gladly accepted. I became their grocery shopper. And a friend with an open ear. Read more »

Our Fucking Cabin Part V [M32/F31] [Outdoors] [Vanilla] [Hand Job]

*The parts I to III are* [*over there*](https://www.reddit.com/r/dirty_boy96/comments/y154r6/our_fucking_cabin/?utm_source=share&utm_medium=web2x&context=3)*. Part IV is* [*over there*](https://www.reddit.com/r/dirty_boy96/comments/yjmp36/our_fucking_cabin_ii/?utm_source=share&utm_medium=web2x&context=3)*. I advice you to read those first. Enjoy your read.*

The following days – day eight to day twelve for us living in the mountains – were filled with cutting and splitting firewood for the winter. My wife and I followed our neighbors advice. Ad first we got some tools out of the shed. We found and ax and a saw. Both tools needed some sharpening.

Luckily some sharpening equipment was in in the tool shed too. We tried our best, and in the end the saw was cutting wood again. Once the saw was up and running, we began to cut the logs and bigger branches into smaller pieces. It was hard work. In the evening my wife and I collapsed into our bed. We were sleeping like the dead.

The next day was about the same: Cutting wood, and in the afternoon splitting it into pieces. Sweat was running down our bodies all day long. Our arms were tired. Our bodies were aching. But it felt good. The pain, the movement in the fresh air, the deep sleep, it freed our minds. It made us forget about our stressful city lives. And it made us forget about the prime reason we came out there: Sex. Sex to knock up my wife. We just were to exhausted to fuck. Horny was beaten. At least until day four. Read more »

My New Swimming Pool [M35/F64/F67] [Mature] [Hand Job] [Threesome] [Vanilla] [Pussy Licking]

*Part I is* [*over there*](https://www.reddit.com/r/dirty_boy96/comments/yq0lj8/my_new_swimming_pool/?utm_source=share&utm_medium=web2x&context=3)*. I advice you to read it first. Enjoy you read.*

The day after my neighbor and me had fun in my backyard was a sad day: It was a rainy Thursday. The summer made a break until Saturday. Due the fact that my children showed up Friday afternoon, my backyard swimming pool was closed for the public until Monday morning when my kids were with my ex wife again.

On Monday, the pool was open up again. And she, my elderly neighbor showed up again. Again wearing a very suiting summer dress. But she wasn’t alone. By the looks of it, she brought a friend with her. A female friend. A woman around her age, probably a few years older than her. Also wearing a summer dress. Showing off her curves. And yes, she caught my eye.

We three stood in my entrance door for some time. We looked at each other. We checked each other out. We all knew what the goal of the visit was. My dick got rock hard while thinking about what might happen on that day. It was the friend that started a conversation: “So that is him, the one who fucks good?” 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 my age. Their kids would be out at 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 to town hall, I filled out a shitload of paperwork, I hired someone to plan it, I hired a craftsman to actually built it and then I spread the message. Luckily everything went according to plan. I had my pool before summer really hit.

My children, they were nothing but excited about it. They now loved to visit me even more. Thirty five year old me loved hanging out at the pool. It was totally worth the investment. But one thing wasn’t working out as planned. Despite me spreading the message in the neighborhood, no women my age showed up to sunbath beside my pool. Read more »