Meanwhile I am a perfect Sissy. A next to perfect fuck toy. A cum dump, the sluttiest slut out there, but I wasn’t always that way. I wasn’t always what I wanted to be. My transformation began about three 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, I was twenty one years old back then, my roommate was twenty six, after moving in, 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 we grew closer more than just fast. The fact that I was a man and she was woman didn’t really mattered for the two of us. We got along, we found out that we had a lot in common, we began to spent more and more time together. And we more and more got comfy with each others presence.
And nope, that all wasn’t happening over night. It took months to really get to know each other, but still, months hanging out with each other, spending as much time with each other as possible – nope, we were no couple back then – weren’t by far not enough to discover every secret the other one has.
We both were single back then, so each one of us spent some time in their rooms, I was jerking off, she was toying her pussy to get some sort of sexual relief. We both loved playing with ourselves, and we both got got more open to a certain degree regarding our sexuality. And no, we weren’t sitting in the living room masturbating next to each other, we just stopped locking doors, we even stopped closing doors from a certain point in time on.
So it just was a matter of time until one would run into the other, catching someone in the act, and I know for certain that both of us wanted exactly that to happen. Just no one wanted to make the first move.
Then one day it just happened. I was in my room playing with myself when my roommate came back home from work. She wasn’t thinking that much when she saw that the door to my room was open, so she just came in. Without knocking, as she had done it more than once in the past. She probably wanted to tell me something that happened to her.
But when she saw what was going on inside the room, she froze. I was laying on my bed, wearing one of her panties and one of her bras. I even made the effort to fill the cups with some clothes of mine. On the big TV screen in front of me some sissy hypno porn and my hand was going up and down my rock hard, totally hairless dick. I was moaning out loud, I was enjoying myself.
It took me some time to realize that my roommate was in my room. It took her some time to process what she was seeing. But after a while a huge smile appeared on her face. While I was looking at her, I kept on jerking my hard wood. I just didn’t bothered to stop, to cover me up or to freak out in any way at all.
Then she just stood there and watched. She was licking her lips while doing so. She waited, she smiled, she seemed to more than pleased about what she was seeing. Then I came while wishing to be one of the sissies on the screen, while I dreamed of sucking a big cock or getting fucked by one. It came good. I came all over my hand.
I tried to lick my hand clean. But I failed horrible. Horny was gone, post nut clarity set in and I couldn’t bring myself to clean after myself. I fucking hated when that happened. And it happened a lot.
My roommate was watching it all. She staid until I was finished, then she opened up her mouth for the first time a few moments after my cum shot out of my dick: “I am so sorry to have disturbed you.”
Then she left, without saying any furthers words. I clearly had no clue how to react on her behavior or what to do next, except taking a shower. To get the sweat and my own cum off my body. So I put on some sweatpants and a T-shirt and headed straight into the bathroom.
After I was finished in the bathroom, while grabbing some snacks in the kitchen, I ran into my roommate. Awkwardness was filling the room. I had no clue what to say to her. So I excused myself for not locking the door. As smile appeared on her face: “No need to excuse, I liked what I saw. It even turned me on more than a little bit.”
Some of the nervous tension left my body. I asked her if she was serious? She confirmed what she had previously said to me, and then she began to ask question: “So you are just turned on by sissies, or do you actually want to be like them? Or are you already one?”
It took me some time to answer her question. I blushed, my head was probably more red than the ripest tomato out there. I really struggled to get the following words out: “I want to be like those gorgeous sissies. I want to be the perfect sissy. But I struggle to transform myself into one.”
A huge smile appeared on her face. She even hugged me. Then she looked me in the eyes. No judgment was to be seen. She told me that she had no problem with my wish, my desire, and to make things even better, she asked me the following question: “Can I help you with your transformation?”
Now a huge smile appeared on my face. I nodded with my head. Then she hugged me again. We had sealed a deal. She was helping me to reach my goal to turn myself into the perfect sissy, the perfect sissy cum dump, only there to serve man and cure their urges. No matter how nasty their urges might be.
After we agreed onto the goal, after she assured me her help, we sat down and talked. We made up a game plan on how to reach my goal. The overall tone was going step by step, and not forcing it too much. A slow transition. One step after the other. But there was one thing we agreed upon from the beginning on: The whole progress should be documented. Documented online, call it a sissyfication diary. With regular updates on everything was going on.
After talking with each other, me and my roommate hugged again. It took us hours, a lot of snacks and a few cup of coffee to talk it all through. A couple of mentally demanding hours, so it took me some time to calm down when I was laying in my bed latter on. I had to process it all, and in the end I came to one conclusion: I was nothing but happy to have been able to share my desire with someone else. I was even happier that she offered me her full support. And I was more than just excited about the journey that was laying in front of me.
On the next day my roommate and I went shopping together. The plan was to get some nice panties, some stockings and maybe even some fitting lingerie for me. Because she didn’t want me to take her stuff anymore. And because we needed something that really suited my body.
Then we hit the shopping mall. We went through one store after the other. Gorgeous panties, bras, stockings and lingerie everywhere. I wanted to have them all. I wanted to feel then on my body. I had a raging boner through the whole shopping trip.
But unfortunately I was running on a very tight budget back then. So two full sets were all that I could afford. I had to choose them wise. But I, and my roommate who was on my site for the whole day, we simply were overwhelmed by the amount we had to choose out. So we called a saleswoman in for help. I was a little bit ashamed, I blushed while doing so.
A smile appeared on her face when she heard that we were looking for lingerie, for panties for me, the young man, not my roommate, the woman standing next to me. She also told me that she had many young male customers like me. And that there was nothing to be ashamed off.
A relieved sight escaped my body. Then she presented her goods to us. She talked about the pros and cons of all of them. She even allowed me to try some of them. That was when I shot my first selfies in woman’s underwear and posted them online. The response was surprisingly more than just good. Many people told me how hot I looked. Some of them even began to follow me.
In the end we bought one full set of lingerie and enough panties to last me at least a week. Yes, I got rid of my male underwear back then. I just threw them into the next trash bin. No need for them anymore. And with them gone, I had nothing to fall back too. I had to wear women’s panties.
Over the next days I felt nothing but naughty because I was wearing panties all day long. But it came with one problem, my dick, he just staid hard. Because the panties felt good, and because wearing panties was nothing but a big turn on for me. I took a few snaps of my hard dick, I asked the community for help.
My followers told me to take matters in my own hands. To relieve my pressure by jerking of my dick. I did what they told me. And to prove them that I tried I sent them pics and short clips of me cumming or of the cream inside my panties. But it was no real solution, now I was jerking off more than five times a day. I was nothing but horny back then. My panties were always covered in my own cum. Needless to say, I posted pictures of my cum covered panties online. Some fans were asking me to sell them to them.
It went on like that for about two weeks. Due work reasons my roommate was barely around in those two weeks. But when she finally had some time for me again, we talked about what was going on. A smile appeared on her face when I told her that many people liked my pictures. Her smile got even bigger when I told her that people were offering me money for my creamed panties: “Let’s sell as many of them as we can.”
And we sold a lot of panties during the upcoming months. We used the money to buy cosmetics and other body care products for me. Back then I began to wax my body. From tip to toe. To make me nice and smooth. Because no one really likes a hairy sissy. And it worked, my follower count went up with every naughty shot I posted.
But despite wearing panties, despite having a smooth next to hairless body, in my head, I still was only a horn man. Nothing really changed. And that really bothered me. Because after a few months in, at least some minor changes inside my head should have been going on. But nothing.
I talked with my roommate about it. She did some digging, and she figured out that me jerking off all the time was the problem. The panties made us money, but it was contra productive regarding my transformation. We came to the conclusion that the masturbating had to stop.
At first we agreed that I just won’t do it anymore. It worked for a couple of hours. Then I was playing with my dick again. It only took a day until she caught me playing with dick. The moment it happened, she shook her head: “Nope, this isn’t working out.
Luckily she had already browsed some places online, she did some reading and had a solution on her hands: It was time to lock my dick away. All day long. To stop me from playing with myself. I nodded with my head while she told me that I would have to wear a chastity cage. I have seen then on videos, on pictures, but never actually had one for myself.
So it was time for my roommate and me to do some online shopping. We measured my limp dick first then we went on cage hunt. And damn it, we were blown away by the amount of devices that were on the market. We red a lot of reviews to find a beginner friendly device. Luckily we enough panties sales money left to order half a dozen. Now the waiting for a delivery began.
Source: reddit.com/r/eroticliterature/comments/10u84g1/how_i_turned_myself_into_a_perfect_sissy_m21f26