29/11-2008:

Hello Master. I know that my diary is late and I fully expect there to be consequences. I'm very sorry.

Today I have been spending most, if not all of my time thinking about who I am. I've been going back and forth with me being this way; a crossdresser, submissive, bisexual. I tried not thinking about any of those desires and was thinking that I just wanted to be normal.

But I couldn't do it. I couldn't stop thinking about being a sissy maid, dressing up and being treated like a whore. I know there is no excuse for my message being late, but this isn't an everyday thing that I go through.

I've decided to stop fighting it, because I know that I'll just lose. I think you might need to train me to love being a sissy slave or maid. Even if force is needed.

I'm sorry once again, Sir. I'll be good from now on.
 
slave jade

30/11-2008:

Hello Master.
 
Today I've been wearing my panties, but everything else I've been wearing is male clothing. Which just isn't right.
 
I've been thinking a lot about the day I get to do all the things I want to do; dressing up as a girl, fulfilling your desires, sucking cock, swallowing cum and getting assfucked.
 
I've been aroused a lot today. Both from my fantasies and galleries I have found on Imagefap.
 
I haven't been doing much today, Sir. Mostly listening to music, browsing this site and homework.
 
- Your sissy maid Jade

1/12-2008:

Hello Master.
 
Today's December 1st so I'm getting a little excited because Christmas will be soon, and that means that the package you have for me will arrive soon. Then I can dress like the girl I am for you :)
 
I was at classes today, which isn't very exciting at all. I'm sure you don't want to hear anything about that, but it was fine. Sometimes I would drift off and think about the nice lingerie my loving Master has bought for me.
 
It's been cold and wet today, so not very pleasant weather at all.
 
When I arrived home, I did my work and then logged on to read any messages. I've also been reading some TS and TV/CD comics, which got me very hard. They are in my favourites under the "comics" folders if you would like to look at them yourself.
 
I've had to suffer another day of wearing male clothes.
 
I've shaved my cock for you Master and have been training my ass, like you instructed. I loved it, my ass was so tight and it felt so good, going in and out. It's gotten me very excited for when my Master's cock will stretch my ass and slide in and out of my tight ass until you orgasm and I feel your warm, creamy cum in my ass as it shoots out of your cock.
 
- Your sissy maid Jade

2/12-2008 

> I'm sorry about this diary being late, Master, as we have discussed before.
>
> I wish this diary entry could be dirty, but today was very boring. Sorry Master.
>
> It has been cold and frosty all day, and I've spent most of my day at classes. Nothing exciting there, and then after a day of classes, I have had lots of work to do and no time for anything else besides eating dinner. This means that I wasn't able to carry out your order of training my ass with a wider candle, which I am very sorry for Sir.
>
> I'm very tired right now and hope I have a lot less work to do when I get back from classes tomorrow, so I can obey my loving Master's orders. I have been spending so much time being a student today that I've had very little, if any kinky thoughts that involve me being submissive at all.
>
> Sorry if this diary entry disappoints you, Master. Tomorrow's will be better.
>
> - Your sissy maid Jade

3/12-2008

Hello Master.
 
Sorry to use this email address once again. I don't think Imagefap will let me send me long messages like this one because it just won't work.
 
Once again, I had another day of classes and it has been very cold and frosty. The ground has been very icy and I almost slipped over a few times, it's a good thing I wasn't dressed in high heels!
 
When I returned home, I saw that I had a new message. I knew exactly what it was about without even reading it; My Master asking the whereabouts of my diary entry, and rightfully so. I knew I had been a bad sissy maid and that's how I felt when I was replying to the email.
Then I decided to do my work whilst waiting for my Master's reply so that I would have spare time to obey his orders, and I just knew that I was going to be punished.
 
When I read your reply, your presence was really felt; as if I was at your feet and you were making sure I knew who I answer to. I felt terrible when I read about how much I had disappointed you, Master. That was when I promised that I'd be a good sissy maid to you, and I actually wanted to carry out my punishment because I knew that I deserved it.
 
I laid a towel down on the floor in case my punishment became messy, and gathered everything that was needed; Olive oil for a lubricant, blindfold, camera phone, mirror, 5 cm wide deodorant can wrapped in clingfilm because I had no candles and no condoms and I couldn't find anything that was like a cane, so I planned on using a belt to punish my naughty sissy ass with.
 
I sat on the towel, in just my panties and blindfolded myself like I was told. This was when I couldn't stop thinking about how much I had disappointed my caring Master, and I lubricated the "toy" with the olive oil and poured it over my pussy. I knew that if it was my Master punishing me, he wouldn't have been gentle at all by opening up my pussy a little first. So I pressed the "toy" into my pussy and it slowly began to penetrate the opening as I relaxed it. It began to slide in slowly, I felt sharp pain as my hole stretched wider than it has ever before as well as the cold canister as it slid deep into my ass. It hurt for a little while until my hole grew used to how much it had been stretched, and I knew I deserved every feeling of pain I received.
 
Still blindfolded, I reached for the belt and my pussy felt very filled. On hands and knees, I took the belt and lined it up and hit each ass cheek 5 times, and I didn't hold back too. If I was going to have streaks for at least 24 hours like my Master said, then it was going to be hard and it was going to hurt a lot. It did. With each strike of the belt I whimpered, thinking about what a naughty sissy maid I had been. It hurt so badly that I even forgot about the 5cm "toy" that was shoved deep in my pussy.
 
I removed my blindfold to see large red streaks across my cheeks, they were stinging a lot, and are still tingling as I type this. I took a photo of the humiliated sissy maid I was, with "her" pussy stretched wide and stuffed, ass cheeks stinging.
I could feel how gaping my pussy was after I had slowly slid the "toy" out. And I thought that I would be good to my Master for once and took a photo of the gape. After all, my Master deserves to see how stretched his commands have left my pussy.
 
I will be a good sissy maid from now on, Master, and I will email you the photos very soon. I hope that the description of my punishment will satisfy you, Sir, knowing that you can punish your sissy maid without even being in the same room.
 
Have a good night, Master.
 
- Your sissy maid Jade

5/12-2008:

Hello Master.
 
This week has been quite stressful because it is nearing the Christmas holidays, so there is lots of work to be done for classes. Which is why it's nice to have this weekend as a little break from all of this work.
 
The weather today was very cold, once again, but it doesn't really bother me. A typical weekday for me; get up early, go to classes and come back home. Very boring, but at least it wasn't that boring once I returned home :)
 
It was nice to chat with you briefly about my future and my interest in crossdressing. It's good for me to talk about it, because right now there is not a lot that I can do with crossdressing besides talk about it. So thank you for that. But then I had to overstep my permissions and try to negotiate this whole diary task with you, Sir. I realise that was very bad thing to do and there will be a punishment tomorrow. I am sorry once again, Master.
 
It's nice to know that my Master is interested in all aspects of my life, and that is why he wants me to write this diary every day. I just hope you can understand if any diary entries are a little boring and short because not much happening that day, Master.
 
During our chat, I was hard as soon as you ordered me to take my pants off and stroke my cock. I hope it pleases you to know that  you have the power to make your sissy maid very aroused, Master. I was very grateful for being allowed to cum, Sir. I felt quite aroused to be ordered to masturbate and cum on my Master's demand.
 
It will only be a few more days until the presents you have sent me arrive, and my excitement grows larger everyday, Sir.
 
Tomorrow is Saturday so that means I can rest a little longer in the morning, but I know that I have to be ready for my Master's orders. I am quite tired now, so I will be going to bed very soon.
 
Until tomorrow, Master.
 
- Your sissy maid Jade