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.
But back to the moment when she came in my room back then. Despite that I was planing, that I was hoping that it would happen, I froze when she came in. So did she. Seeing me on my bed, wearing her panties, jerking off to some sissy porn, just caught her by surprise. Luckily she didn’t got mad or anything. Just a smile appeared on her face when she say what I was exactly doing: “Sorry to have disturbed you, I am going to leave you alone now.”
Then she left my room. Without closing the door behind her. I, kept on jerking. Imagining how it would be, when I was the sissy in the movie. Imagining how awesome it would be to suck some nice cock and getting pound by the same cock afterwards. While wearing some fine lingerie, while wearing some hot makeup, while looking, while being a hot woman.
I took my time with jerking off. I squeezed my balls. I edged. I enjoyed the feeling of being horny as fuck. I delayed my cum shot as long as possible. I was promising myself to eat my own sperm after it was out of my balls. But then, the orgasm happened. I couldn’t hold myself back anymore. No, I wasn’t able to eat my own spunk. And unfortunately, the nice horny feeling left my body too. Same shit as always.
When I was done, I got dressed and went into the bathroom to give myself a proper cleaning. On the way back to my room, I ran into her, my roommate. Awkwardness was filling the room. I felt embarrassed about what hat happened earlier. But she, she took it cool. More than just cool. A smile appeared on her face: “So you are into sissies?”
It took me a while to figure out an answer, I was thinking of talking myself out of it. I was thinking about telling her a made up tell. But in the end, I went for it. It told her the truth: “I didn’t want to fuck some cute sissies, I want to be one. The perfect sissy. The most perfect and hottest fuck toy you can imagine.”
A damn fucking huge smile appeared on her face once she heard me saying that I want to be a perfect sissy: “Do you need some help changing yourself?”
No, she wasn’t judging me. She wasn’t beating on me. She wasn’t looking down on me. She just offered me her help. And that put a huge fucking smile on my face. I finally had found someone that was willing to support me, someone that was willing to help me turn into the person I wanted to be.
It told her that it would be awesome if she would help me. Better than awesome, fucking awesome. Then we sat down and talked. To my surprise, she knew a lot of sissies. She told me that she was into sissies. That turning me into one was a very welcoming challenge for her. And then, we set up a plan together.
We didn’t wanted to force it all too much. We went for a slow transition. Step by step. One slow step after the other. To turn my male body into a perfect fuck toy. To change my mindset. To turn me into a cock loving, cock craving and cock addicted sissy bimbo slut.
And yes, we came up with the great idea to document the progress. To put it all online, to share everything with the rest of the world. To inspire others, and yes, to maybe make some money with it. Because well, there is definitely a market for that kind of stuff out there.
After everything was planed out, no not down to every detail, just a list with stuff that need to be done, stuff that had to happen, we called it a day. I went back in my room, where I struggled to fall asleep, because my mind was only filled with one thing: My dream will finally come true.
The next day my roommate and I went shopping. For some nice panties, for some nice stockings. Because she didn’t wanted to share her stuff with me. So we had to get my own. Luckily I had by far enough money saved up.
The shopping trip itself was interesting. All the working in the stores we went into were more than just supportive. And to my surprise, they were very competent in picking out underwear that suited my figure. I clearly wasn’t their first male customer.
When we came back home, my roommate and I got rid of my male underwear. From now on, panties only. Best always compared with some stockings. The first step was taken. And it felt great. Wearing panties was nothing but a turn on for me. I was jerking off like a maniac. I was creaming up my panties nearly every day.
But that was a problem. I should have abstained from every male sexual activity to change my mindset, to turn all more female. But I struggled to do it. I was to weak back then. To used to relief my urges in the easiest way possible. I asked my roommate for help.
My roommate, she immediately offered me her help. She totally understood how hard it is to stop playing with yourself. And she already had an answer, a solution for my problem: It was time to lock me up. To put my penis into a chastity cage. To stop me from playing with myself, and to let my dick shrink down to an acceptable size. Yes, she made her homework. She really dug in deep into the process of becoming a sissy.
Then we ordered a few chastity cages: Different models, different sizes, to find a fitting one. Because when you wear something 24/7, it has to be comfy to wear. So we picked ten cages and ordered them. Yes, not cheap, but well, sometimes you have to invest something to reach your goals.
While waiting for the parcel to arrive, I made another huge step. I began to smooth up my hairy body. At first I was thinking about shaving, I asked my roommate how to do it best, but she voted for waxing and tweezing. I asked her if it would hurt, she said yes. But the result would be by far better than shaving. And yes, she did the same.
The day after I went shopping. Wax, wax and more wax. In the evening the waxing began. Luckily my roommate was helping me. Luckily because I had no experience regarding that field at all and there are many hard to reach hairy spots on a male body. The whole procedure lasted for a few hours, and it hurt like hell. But here, it clearly was a case of no pain, no gain.
Needless to say, we took pictures, we made videos off the whole procedure and put it all online. The response on the content was great. Many provided tips on how to smooth your body. Permanent hair removal was my favorite, but damn it, I hadn’t had the funds to go through that back then. But our audience was growing fast.
A few days later the cages arrived. It was a tough fight to try them all, because as soon as I tried to put one on, I got hard. Luckily we anticipated that this would happen, so we had a lot of ice in the freezer. My roommate was very patient and supportive and a few days later I had a favorite. The cage was comfy to wear and had the right size.
After the right one was found, I handed my roommate the key. She was in control of my penis now. And I couldn’t have found a better key holder. No matter how hard I begged, I was really desperate for a relief after a few days, and the desperation grew, she was persistent. She said now. She always took her time to explain me, that it was better that way. That it needed to be done. That it was the only way for me to transform. And that we would take care off my desires, my horny, my urges in a very female way soon.
Source: reddit.com/r/gonewildstories/comments/xku20c/mf_how_i_turned_myself_into_a_perfect_sissy