How I Turned Myself Into A Perfect Sissy Part IV [M23/F26] [Anal] [Deep Throat] [Pussy Licking]

*I 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)*. Enjoy your read.*

A few months later it was time for the next step. Not the biggest step out there, but it was an important one for me. My roommate and I went to a barber shop. It was time to get my first female haircut. At least the first one done by a professional, because my roommate has done her best to make my hair look as good, as female as possible since I began my journey.

Once the hairdresser was done she showed me myself in the mirror. I just felt pretty. I felt gorgeous. Maybe for the first time ever. I took more than just one selfie, the all went online, and my viewers, my fans, they loved them too. Nothing but uplifting comments on that day. I just felt nothing but happy.

On the following day it was time for a very painful appointment. It was time to burn away more of my body and facial hair. It was time to make me even smoother. The progress so far was good. My beard was only half as thick as before, my chest hair was more or less a thing of the past, my followers had spoken many uplifting words to me. To keep me going. And yes they were paying for it all too. I just love them all.

Besides changing my visual appearance there was many other stuff I was working on back then. I had regular sessions with a vocal coach. To make my voice more female. To be able to moan more female. To get rid of my deep male voice at all. It was a demanding task, but a task that had to be done, when I wanted to reach my goal.

And something else had to change too: The way I walked, the way I was standing, the way I was interacting with other people, the way I was sitting down and standing up, it all wasn’t female enough back then. It all had to change. Some things came easier, like not spreading my legs anymore, because I was mostly wearing skirts. Then the walking, high heels help out a lot to change they way I walk. But it was a tough fight to get all the male stuff out of my head. But it was a challenge I was more than just willing to take, to reach my goal, to become the perfect bimbo sissy cum dump. Someone every men on Earth is dreaming off.

Unfortunately, or luckily, all that stuff had to be financed somehow. Besides posting selfies, besides having a transformation blog with pics of me on it, I made most of my money, as mentioned and described in my previous posts, by making porn.

Meanwhile I was doing life streams were I did whatever the viewers wanted me to do, I was doing for sale only videos were I was playing with myself. I was selling nudes. And I really really have to thank my roommate, because she was the one behind the camera. She was the one editing everything. She was the one working for me, working with me all the time. And that was why I was paying all of the rent. Yes, I already made some good money back then.

Then one day, I was doing my live stream, my roommate disturbed my show. I was just riding a huge dildo a user sent me, when she just came in the room. She clearly wanted my attention. Then she went in front of the camera for the first time. She introduced herself to my, to our audience. Then she dropped another bomb: She was planing to fuck me up the ass. With a strap on. She wanted to take my virginity. Chat went wild. And I had a huge smile on my face. I looked my roommate in the eyes, she looked me in the eyes, then she left and I went on with my show. Donations were through the roof on that day.

After my stream was over, I met my roommate in the kitchen. Again, we smiled at each other. We looked each other in the eyes. Some tension was building up. I hugged her. I wanted to kiss her. But I held myself back. She later told me that she was doing the same. Then we had a talk.

We talked about the virginity thing. I was nothing but excited about it. So was she. We were planing on shooting it on video. We were also planing on hiring a professional, porn experienced camera man to do so. To get the best possible pictures, the highest quality video. Luckily already had someone on our hands. Someone my roommate knew from arts school.

Once everything was planed and set up, once the toy was ordered, the waiting began. The waiting for my first time with my roommate. The woman, the girl that was there for me since the beginning of my transformation. The one that cheered me up. The one that was mostly always nice and understanding to me. The one that was currently building up her own name as an online content creator. Yes, our shared apartment slowly but steadily turned into a porn studio.

Then the big day came. The camera man showed up on time. He brought some of his own equipment with him. We began to set up our stuff in my roommates room, after me and her gave the place some proper cleaning they day before, then we went to do our makeup will the camera guy was setting up his lights.

Once everything was set, we did a few test shots, then it was time to put on our lingerie, to do the last and final preparations for the scene. We were doing the classic. She caught me masturbating, then she joined in and showed me how it is done in a proper way. We both were really nervous.

But as soon as the camera was on, as soon as I was laying on my roommates bed, with her scent in my filling my nose, I relaxed. I slowly undressed myself. I played with my nipples. I sucked on my fingers. Then I got a toy out. Carefully lubed it up and then they toy went up my ass.

I was in no hurry. I slowly slid the toy in. A few moans escaped my throat while I was shoving the decent sized plastic dick up my ass. It felt good. Then I fucked myself. Slow, hard and deep. My caged clitty soon was spitting juices. Now it felt really good.

Then my roommate came in. Some cheesy dialogue was spoken. Then we kissed for the first time. I had a very warm and fuzzy feeling inside my belly while kissing her. Then she sucked on my nipples, I sucked on hers, I was nothing but turned on. My asshole felt all tingly. I wanted something in it.

But first I was eating out my roommate. My tongue inside her well tasting pussy. Then my tongue was on her clit while three of my fingers were sliding in and out of her fuck hole. Her moaning was filling the room. It didn’t took long until she had an orgasm. We both totally forgot that there was a camera, a cameraman with us in the room.

After my roommate had an orgasm, it was time for her to return the favor. She put on the strap on, then they camera was rolling again. At first I was giving her a blow job. I took the dildo as deep as I could. I gagged on it. I shed a few tears. I love it. It felt so good feeling the toy sliding in and out of my mouth while looking my roommate in the eyes.

Then, finally, it was time for some proper fucking. My roommate had some experience on the field, an ex-boyfriend of hers was up the ass only, so she knew what she was doing. She lubed up her strap on, the put some lube on my asshole, I was on all my four, ass high up in the air, then she kissed me on my ass and then, she slid the toy inside.

As soon as she opened up my dirty hole, moaning escaped my throat. Finally, I got fucked for the first time. Then she slid her toy deeper inside. She took her time. She gave me time to get used to the feel of it. Then she began to fuck me. Slow and gentle, but oh god, she went in deep. It felt nothing but awesome.

As soon as I was used to the penetration, my roommate fucked me hard, she fucked in the right rhythm, she was hitting the right spot. I felt better and better with every thrust she gave me. Some inner heat was building up inside me. My eyes were running in circles. My caged dick, my balls were bouncing back and forth. My moaning was filling the room. And then, boom.

My legs began to shake. My body began to tremble. My balls unloaded themselves. My roommate fucked me elsewhere. I was gone. My sweat covered body collapsed onto the bed. She gently pulled out while all tension was leaving my body. I was nothing but a happy orgasm filled mess. It took me some time until I was myself again.

When I was back in my body, my roommate and the cameraman were smiling at me. The told me that watching me was nothing but awesome. They also told me that they had filmed it all. With two cameras. And they were right, the video became my first hit. It reached a lot of people, and yes, it made me more than just some money.

After my first time was over, my roommate and I cleaned ourselves up, then we threw on some comfy stay at home clothes and then we helped the cameraman putting away his gear. Then we had pizza together. And then, when the cameraman had left, my roommate and I just jumped onto each other. No we weren’t fucking, we just were kissing. Cuddling and enjoying some warm and fuzzy feelings inside our bellies. We had fallen for each other.

Source: reddit.com/r/Erotica/comments/ybbmka/how_i_turned_myself_into_a_perfect_sissy_part_iv