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

As I had agreed on being Holgers slave from now on, he actually wrote me some messages every day, asking what I was doing, how I felt,... In his first messages he had demanded, that I check my phone as often as I could, because he did not want me to take long for an answer. At first I thought it might be annoying, but after some days I really liked it and thought it was hot to be controlled in that way. Friday morning I got a text, in which Holger demanded to get to know my address, because this time he wanted to visit me. I did not answer immediately after reading his message and like five minutes later I got another message from Holger. He wrote something like: "You have to obey me slut. If you don't want to get punished, give me your address. Now!" I answered and gave him my address. After work I rushed home, took a shower, shaved, vacuumed the rooms and generally cleaned up a bit. After I was done with everything I started to get ready for Holger. He told me, that he was arriving at 11:00 pm. I thought he was joking, but then remembered, that he had to work in the theater until 10:00 pm. As I was bored, it was around 7:00 pm, I started to search the web for stuff related to sissification, feminization, BDSM and other stuff related to those themes. As 11:00 pm was getting close, I was really horny already and was eagerly waiting for Holger to arrive. Holger arrived precisely at 11:00 pm, he rang the doorbell and I opened the door. I was kind of nervous, but also very, very horny. After entering my flat he started to look and walk around. He opened some doors of other rooms and even some doors of cupboards and my wardrobe. After he was finished snooping around (which felt really weird by the way) he went into the living room, sat down on the couch and told me to get into my position in front of him. I did as he told me. I don't remember the following conversation completely, but I know that we spoke about how far I was ready to go. I remember some questions from him, because they scared me, made me uncomfortable or at least gave me a weird feeling.

These questions were:

1. Are you willing to get rid of all your male underwear?

2. Are you willing to wear the chastity device every day?

3. Are you willing to train yourself to be able to cum from fucking yourself with a dildo?

4. Are you willing to be completely owned, controlled and getting decisions made for you?

5. Are you willing to experiment with different practices with the goal of minimizing/eradicating your Limits?

These five questions were the ones I needed to think of for some minutes and needed to speak with him before answering them.

1. + 2. We spoke about that for some time and he was really serious with it, he wanted me to wear panties all the time. As I needed to change clothes at work, I was not really sure about this and asked him, that I would need to keep at least some pairs of boxers for work. For the second question I agreed to wear the chastity device in my spare time, but, for the same reasons as above, not at work.

3. I agreed, because as I knew, that it was possible I wanted to experience it. (Further I thought, that I could back out at every time, and I wanted to feel it at least once, to get to know it).

4. I asked him what he meant by that and he told me that he wanted to control my life in every aspect. He wanted to know where I was at any time and wanted me to be ready to dress up and be ready for him at any time (besides work). He wanted to be able to decide if I would be allowed to go out, to go shopping,... basically he wanted to decide what I was doing during the day. This scared me kind of, because I thought of a lot of situations where it would be disturbing and in which I was not able to pull myself out of, to be ready for his demanding. I declined this point, but offered him to be available for him at the weekends and during the weeks, as long as there was nothing preventing me from this.

5. I asked him again what he meant and he explained, that he would really want to stretch my limits. For example he told me, that he would like it to cum in my mouth and fuck me bare. He further wanted me to swallow his piss and lick his ass. He told me that there is no rush in these things and that he would be leading me towards these points with care. I declined this point completely, because I was not ready to go this far.

After our little conversation Holger told me, that we won't be getting along with this kind of “relationship”, if I was not willing to really go for it. He told me, that this is not just picking the raisins and that I can't expect him to do things with me, which make me horny. He admitted, that he liked our meetings and that he was having fun while we were doing things together, but that he wanted more than that, too. The same way I was asking for more than just being “kept” in the theater and occasionally fucked. I understood his point of view, but told him, that I would not be able to go that deep into this, because it needed to stay a secret. I was not willing / able to take it being exposed in any way, even if it would happen randomly / accidentally. After that Holger left. I was disappointed, because I thought we were about of having some fun and that's it. I did not speak to Holger for about three weeks, I even did not dress at home, played with my toys or met other guys. I kept thinking of him and the things we had done together and every time I was getting really horny and sad at the same time. It was kind of strange. After three weeks I decided to go to the theater again and try to talk to him and maybe even ask if I might stay the nights. I was especially petty with shaving myself while I was taking a shower friday after work. I dressed most of my clothes under my normal clothes, packed the rest in my backpack and drove off at around 6:00 pm. After arriving at the theater I went to the counter and asked if I could enter the theater and get a key for my stuff. Holger just greeted me as a common customer, gave me a key and charged me for the entrance and 1,- € extra for the key.

After I was finished with getting dressed up, did my make-up and packed everything in the locker I went to the counter in the theater-area and rang the bell. Holger came up and asked if he could be of service. I asked him to take the key for me, but he declined. He went back into the shop and left me there, kind of frustrated and sad. I sat down on a bar-stool and smoked some cigarettes. I had no interest in walking around or even look after some other guys to have fun with. At it was time to close the shop Holger came to me and asked me to change and leave. I asked him if I maybe would be allowed to talk a walk outside. I was not. Totally disappointed I got changed and left.

The next weeks I kept thinking of everything that had happened and how I wanted everything to happen again, but I did not take any actions.