Introducing Annie May – Distance Control Journal – Week 1

I was delighted to take on another distance control slave last week, please welcome Annie-May, a pretty little submissive girly sissy. Once I discovered that my new pet was very much into being female and feminised I new exactly what direction she needed.  It’s always fun to have a true feminised sissy to play with because it is almost like having a female sub.  I look forward to having a real time session with her soon.


New HOD pet - Annie May
New HOD pet – Annie May

Day 1

My first day eased me in nice and slow and made sure I realised I was Mistresses property. Every morning and before I went to bed I was to strip off completely naked, kneel down and repeat a mantra 3 times as a pledge to be the property of Miss Deelight and to serve her to the best of my ability. I was to do this every day of the week.

There was definitely a certain, vulnerable thrill of being naked and realising I was owned by a beautiful goddess.

Day 2

Today entailed some SPH. Mistress asked for my measurements, which were humiliatingly inadequate. I was ordered to water my dicklett to see if it would grow, and send a photo to Mistress. Around this time, I informed Mistress of my chastity device (size small) that I was to frequently wear throughout the week.

Mistress asked me if I had any girly clothes, so I replied that I had quite a few :) Next I sent Mistress a more detailed description of my fetishes and about me etc, to make up for my somewhat lacking initial message.

After finding out I was a feminine, submissive sissy that longed to be feminized by a superior woman, my training really took off!

I was ordered into chastity, a maid uniform and makeup, and sent the photos to mistress to show I can look pretty on demand.

Day 3

This morning I felt overjoyed when Mistress complimented me on my photos! She told me I make a lovely sissy, which made me inspired to make myself even more girly and prettier than I am. I always want to look my best for Mistress and look after myself. It was a very positive experience, which is just what I needed from a Mistress :)

My task today was to research the Lolita makeup style, particularly the large ‘dolly eyes’ that go with it. So I watched a few instructional videos whilst locked in my small device and had a buttplug shoved snugly up my smooth sissy bottom.

During this time, my Mistress sent me a personal video message! It was so good to see Mistress informing me directly what she expected of her little Lolita and to be a good girl for her. I dutifully watched the videos and did my best copying the techniques on myself. I found I was missing liquid eyeliner and white eye pencil, which are best for this style, and I had misplaced the glue for my fake eyelashes! I was looking forward to wearing those to show Mistress how sexy my eyes can be :)

After making myself extra gorgeous and sissy I sent off the photos of my work. Mistress seemed delighted with my efforts and even picked out a favourite photo of me looking very cute and submissive with my big eyes, blonde curly hair and very small locked up clit! I will admit, it made my day :)

Next I was asked if I had a girly name, so I informed my Mistress that my friend calls me Annie May (because being a fan of anime), which Mistress approved of.

Day 4

Today I was instructed to buy the liquid eyeliner before work in the afternoon. Before then, I was to edge my clit every hour whilst wearing my buttplug. As you can imagine this was very frustrating as I hadn’t had an orgasm for a few days! Then I was to lock my denied little clit up in chastity and go to work. Of course I stopped off at Boots on the way to pick up some Maybelline liquid eyeliner and a white/black double sided eye pencil. I sent of photos of my purchases and my locked clit while at work.

Day 5

Today was another edging day! Mistress seems to have a cruel streak ;) This time, I was to do it every time I used the bathroom. Mistress also checked up to make sure I always sit down to use it. So again, another wonderfully frustrating day for Mistresses little princess.

Day 6

I received another video from Mistress today! It was a humiliating SPH clip that I had to watch 3 time throughout the day…..in chastity. Then before bed I had to watch it again whilst rubbing my clitty, but again was not allowed to cum :( Mistress sent to bed a horny little brat that night

Day 7

Today I sent off a list of all my sissy toys to mistress in anticipation of a much needed orgasm. And Mistress finally allowed it! Of course it wouldn’t be that easy. I first had to lock up my small clit, and get dressed as a SLUT. I put on an extremely clingy and short white clubbing dress my friend had given me. Very slutty and just a little sheer :)

For a full 5 minutes I had to give a blow job to my realistic thick dildo whilst plugged with my prostrate massager, which in itself was pushing me to cumming. Then I had to slide my jelly 6 inch anal dildo up my sissy pussy and fuck myself for 10 minutes! I had to prove to Mistress what a dirty little fuck slut I can be. I took a few photos and made a short clip of me bent over being penetrated. Only then was I allowed to rub my clit…a few minutes later and I came very hard. One of the most satisfying orgasms Ive ever had, thanks to mistress denying me so long, and making sure I was well fucked first…


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