The fifteenth part of my adventure in becoming a TV / Sissy

Now we have to go forward a few weeks, because in the next weeks there was nothing happening. I did search the web for sissy related stuff, but I did not dress, did not wear my chastity cage, did not meet any guys, did not go to any porn-theater,...

All in all it was quite a sad and depressing time for me, because I knew that I really wanted to do something like we had done. One day after work I started dressing up to get over it and started to play with my toys while I watched sissy-hypnosis clips on my computer. As I had the feeling I was 'done' playing I started to take of my chastity cage to jerk myself off, but as soon as I started I felt that it was not right. I locked the cage back on my cock and proceeded to play with my toys. After about two more hours of sissy-hypnosis and playing with my toys I was really exhausted, got undressed (undressed also the cage) and went to bed. I was still really horny, as I did not have an orgasm.

As I started to touch my cock I felt like it was kind of wrong in this moment and so I decided to put the cage back on and slept while wearing it. The next days I put the cage on after work and started to search the web for sissy stuff. I often caught myself thinking about jerking off, but most of the time I stayed strong and kept the cage on, but sometimes I unlocked it and started jerking, but I stopped after some seconds/minutes and put the cage back on.

I started to look on the internet for ideas to keep myself in my cage. I found some site on which someone wrote, that he was using a “kitchen safe”, some kind of cookie box with a timed locking mechanism. He wrote, that he put the key in this box and sets the timer of the lock to whatever time he wants to stay in chastity. Another guy answered, that he was using a simple tupper-ware box. He told that he filled half of the box with water, froze it, placed the key to his cage in the mid of the ice, filled the other half of the box with water, too and froze it again. So that he would have to be totally serious and aware of the situation, in which he unfreezes the ice, to get the key.

I was kind of amazed and decided to try the method with the frozen key. I immediately went into my kitchen, filled a box to its half with water and put it in the freezer. The next morning I took the cage of, before going to work. I placed the key on the middle of the ice, filled the box completely with water and put it in the freezer again. After I was getting home I put on the cage, closed the lock and after that went to look for my key-box. The water was completely frozen and the key could be seen, how it seemed to float in the middle of the ice-block.

I went on over the day, I did not dress and did not anything which potentially made me horny. In the evening I got the ice out of the freezer and left it outside. I went to bed and slept.

In the morning the ice was back in its former state. I was able to grab the key, take the cage off and after that I directly put the key back into the water. As I had no time to freeze the first half of the box, I decided, that it would be the same, when I just place the key on the bottom of the box and freeze the water over it. I put the box in the freezer and went to work. After work I put the cage back on. This was becoming my ritual when I got home from work and I really liked it. I did this for some weeks, in which I did not orgasm once. I came two times during the nights, though. I was not able to do anything to prevent this to happen. After several weeks of “forced” chastity I was getting really horny on a saturday evening. I got dressed and started to play with my toys. This time I really came from fucking myself with a vibrating dildo. At first it felt a little bit like I needed to pee, but after some minutes this feeling changed and was replaced with an arousing, somewhat like a tickling inside of me. It was intense and shortly after this change I felt how my cock began to twitch in its cage, before shooting its load. I collapsed after I was finished, because it was so intense. It was kind of shocking, I remembered that I “wanted to experience it, at least once”, after this I was sure, that I wanted this to happen again.

The next days I tried again to fuck myself until I came, but it did not work. I paused some days and the next weekend I tried it again, still nothing. I was frustrated, because I thought, that it has to happen, because it already happened once. Today I realize, that I was getting tensed up with this and that it probably did not happen, because I was not relaxed and just enjoying the act itself.

As soon as I had figured, that it only happened if I was relaxed and enjoying it, without trying to force it, I was able to cum from fucking myself once or twice a week (mostly every time I really got dressed up and started playing). I started to search the web for guys to meet again and without realizing I went deeper into it. I searched for guys who were dominant. I was not interested in guys who just wanted to get sucked or fucking me. For that reason I needed to decline the guys I had written with. With every passing day I got more and more desperate to find a dominant man. Again some weeks later, I decided to write Holger a message. I told him that I was able to cum from fucking myself with the vibrator and about my routine with the key to my cage. He did not answer at first and I was disappointed again. The next morning, after waking up, I found a message from him. He congratulated me to be able to sissygasm and asked why I told him. I answered, that I felt that he would like to know and that I was really missing the time we had together. He answered me, that he also misses the time, but that he also was not willing to make some kind of arrangement, when he owns a slave. I told him, that I would really like to fulfill his demands, but that some of them were impossible to fulfill. I named precisely the first two questions we had discussed. He asked what was about the last both points and I told him, that I would really want to try to fulfill his demands, but that I don't know if I really would be able to do it, without chickening out or denying anything which he would be demanding.

He answered, that he was thinking the last weeks about all this and that he really wants these points to be fulfilled, but that he would get me a code-word, which I could use every time to stop it, but that there's a rub to it. If I would use the code-word, our relationship will immediately be over. Further he told me, that he would be O.K. with me wearing the cage like I did the last weeks already. He admitted he liked the idea of a frozen key. For my male underwear he told me, that I would nevertheless get rid of it, except one boxer-short. He joked that he would like me to freeze it, too, as soon I get home from work. Immediately I thought about the kitchen safe and told him about it. He told me, that he would be visiting me on Friday night again and that he will be buying and bring this “kitchen safe”. I was supposed to buy an amount of panties until then, because I would need a reasonable amount of underwear for my everyday life. He bid me goodnight and I went to sleep, wondering if I really did the right thing.