*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.
Beside your usual supporter – nope, not looking down on you here, I love every single one of you – that were subscribing to your content, that were buying my videos some bigger ones were contacting me. They offered me a lot of money to spend time with them. Get intimate with them and sometimes even to part of one of my video productions.
On one hand it was more than just awesome that something like that happened. On the other one, I was with my girlfriend, as mentioned above, formerly known as my roommate. We still were freshly in love. We still weren’t able to keep our hands off each other. Fucking someone else just seemed the wrong thing to do back then.
Again, my girlfriend saved the day. She told me that it was okay. She told me that we could do threesomes with them. So the two of us were sharing the man. And she also told me, as long as she knew about it in advance, as long as I would ask her if it was okay for her, it wasn’t cheating for her at all.
For sure, when I would be out getting nailed by some man for money, she would be jealous. She would prefer if I wouldn’t do something like that, but on the other end, the money they offered, it was more than just tempting for her too. Because we were not only a couple, we also were business partners. We even had set up some paperwork to prevent things from getting South in case the two of us would separate.
So the decision was on my shoulders again. It took me a couple of sleepless night to make up my mind. And in the end, I told my girlfriend, that we only would share a guy off camera, on camera it probably would end up being me and a guy alone. To be able to produce more content. And to offer a bigger variety of content. She accepted my decision. And I began planning meetings with some supporters of ours.
The one I always will remember is the first one. He payed a decent amount to enjoy my company. He also was perfectly fine with us filming the whole evening. He didn’t even insisted on wearing a mask or us blurring out his face. He just went for it. And so did we.
We booked a hotel room for the night. We brought our camera gear into it and began to prepare the room before he showed up. I was nothing but nervous. Nervous and excited. So was my roommate. It was my first real dick. My first experience with a real man. And according to the pictures he sent us, he was a well hung one.
Once the camera gear was up and running, we the preparation began. I cleaned out my dirty hole and fucked it a little bit. To open it up, to get used to the feel of it. To be ready to go when he would show up. Needless to say, my roommate filmed it all.
Once my fucking hole was ready it was time to put on some make up, to dress up, my girlfriend did the same, despite the fact that she would only operate the camera later on, but well, dressing up fancy just has something, then we went downstairs. Into the hotel bar and there we ordered a drink. To calm the nerves a little bit.
About five minutes later he showed up. It didn’t took long and we recognized each other. He was very polite from the beginning on. He introduced himself then he asked if the empty seat next to us was already taken. I answered him that he could sit down, if he wanted. And so he placed himself next to us and ordered a drink.
Then we kept on talking for some time. To get to know each other a little bit. To make up a plan for the night. And to warm up. And damn it, he knew what he was doing. He made a lot of genuine compliments, he asked the right question and he told us that this here wasn’t a first time for him. And he also told us, that he knew that it was a first time for me, so he would take his time and go in gentle later on.
After the second drink together we headed upstairs. There my roommate turned on the cameras and the man and I began to make out. We shared a few gentle kisses first. Gentle kisses that turned into passionate ones pretty soon. After some time kissing each other, after our hands were exploring our bodies he undressed me. He got me out of of my dress, but he left my sexy underwear and my stockings untouched while he stripped totally naked.
The moment I saw his big rock hard dick popping out of his underwear, my mouth was watering. Finally, a real dick. I made it. One big goal of mine was within in reach. And moments later I was jerking him off while he was laying on the bed with his dick pointing towards the ceiling.
It didn’t took long and his moaning was filling the room. And it also didn’t took long and I wanted to feel him inside me. So I wrapped my lips around his glans. Luckily I was already well trained back then, so I had no difficulties taking him into my mouth. As soon as he was inside me, his moaning got more intense.
I kept on sucking on his glans for some time. To enhance his pleasure I began to squeeze his balls a little. Gentle. Because some men are very sensitive down there. It didn’t took long and he asked me to squeeze them hard. His cock was twitching when I gave him the first real hard squeeze. He clearly was enjoying himself.
Again, I kept on going for some time. To give my roommate enough time to capture it all out of some different angles. When she had enough footage she gave me a thumbs up and then I took his dick deeper. I took him down my throat. Gradually. Slowly. Until he was in balls deep. I took him without gagging, without a single tear coming out of my eyes. And yes, having him down my throat, felt nothing but great. It was such a huge turn on for me too.
The men was moaning out loud all along. He really enjoyed himself. He began to loose himself. He soon wanted more. He wanted it all. He wanted to fuck me. And fucking me he did.
As soon as we had enough deep throating footage it was time for some real fucking. He gave me a few kisses first. Then he pulled down my pre cum soaked panties, lubed up his dick, bent me over and slid his raging hard boner inside my virgin asshole.
He took his time while doing so. Then he fucked me. He took me slow, hard and deep. My eyes began to run in circles. Our moaning was filling the room. My roommate was still filming it all. It didn’t took long and sweat was running down my bodies. His dick sliding in and out of my fuck hole, it felt nothing but good. I totally lost myself. He turned me into his slut. Into his cum dump.
One hard and deep thrust followed the next one. Then another one. My caged limp dick was spitting pre cum all the time. I felt something building up inside me. Some inner heat overcame me. It all felt so damn fucking good. I came closer and closer to an orgasm every time his dick went in out of my asshole.
And then, he came. He finished himself inside me. I could feel his twitching dick unloading dumping his huge load inside me. Him cumming inside me made me jumping over the edge. I turned into a trembling orgasm filled mess.
I collapsed onto the bed while he gently pulled out his dick. I had more than just a satisfied expression on my face. He fucked me really good. He made me feel like a real woman. He turned me into his slut. And he really enjoyed himself while doing so.
It took me some time to regain myself. When I was back I looked at my roommate, I looked at the men and the both just had a huge fucking smile on their faces. The men because he came good too, my roommate because she had captured some awesome footage. And because she just enjoyed the show.
After finishing the men went went to take a shower. Then he got dressed and left. Well, he said goodbye first, he hugged and thanked me for the experience and he insisted on us sending him a free copy of the video, and then he grabbed his stuff and left the two of us alone in the hotel room.
My roommate and I, as soon as it was only the two of us looked each other in the eyes for a long time. Then we shared a few gentle kisses. Then we talked. We talked about the night. About my experience. About how it felt for her. And we came to the conclusion that we both had no problems with what had happened before. No one was jealous, because it was business only. So it wasn’t the last time of something like that happening.
After we had a talk, we decided to leave the hotel and take a cab back home. I went to take a shower while she was packing up the camera gear. Then we checked out of the hotel and drove back home. Back at home we went straight to bed. Some cuddling, then we fell asleep, because it was a long and exhausting day for the two of us.
The video itself, after it was edited, did more than just well. The money it made and the money I got for the one night were enough to pay for some new lips for me. Some nice big lips. So I reached two important goals on my transformation tale back then: First time with a real dick and my first surgery to turn myself into the perfect sissy. But many steps were left to take to reach my final goal, to become the perfect sissy cum dump.
Source: reddit.com/r/eroticliterature/comments/104s6lr/how_i_turned_myself_into_a_perfect_sissy_part_v