My first interactions with Princess Annie were almost 10 years ago while I was still a young, horny, pathetic 20-something sissy. I spent a lot of time online messaging with dommes, scrolling twitter pages and fantasizing about hot femdom scenarios. And one day I scroll past Princess Annie, in her leather, the iconic smirk of hers, a clip of the laugh that has come to make my useless sissy stick twitch uncontrollably when I hear it. So obviously I liked the tweet, and few more, then a few more. Until one day, in a mood I can only assume in equal parts sadism and generosity Princess Annie raffles off a short skype session to her followers, something along the lines of “I’ll choose a random like to cam with this evening” I was selected and so my relationship with Princess Annie truly began.

That first time camming in those short 5 minutes I got to show off what a pathetic and utterly absurd sissy I love to be. An attribute that any followers of hers must at this point must know she loves (at the very least to take advantage of). So we continued to interact and play as Princess Annie conditioned me to be sluttier and sluttier, weaker and weaker, more and more obsessed.

Things started off relatively light. Get dressed up in the absurd, frilly sissy dresses I had, suck on a dildo, bounce on a butt plug. But the thing about Princess Annie is that above all else she loves to be IN CONTROL, and in my experience, this often manifests in pushing her subs to do dirtier things, more humiliating things. And as it turns out when a sissy is horny, at least when this sissy is horny, trying dirtier, more degrading things sounds very very hot. And so for the past decade my escapades with Princess Annie grew more varied and when remembering them leave me with a deeper feeling of shame.

The escalations began probably much as anyone would imagine. Dress more ridiculously and get bigger toys. Tame enough in the grand scheme of things. But from there things went in less predictable directions. The number of experiments I have been put through would be daunting to try and remember so I won’t try to recount all of those experiences. But there have been 3 areas in particular that appear to have brought Princess Annie great amusement and I believe may be responsible for her consideration of me as a fun toy. The introduction of distance-controlled toys, diapers, and sploshing.

The distance-controlled toys allow Princess Annie a level of control over this slut that would otherwise be impossible. With the Lovense toys she doesn’t have to tell me what to do with my toys, she can raise the intensity of that plug shoved up my ass and those nipple clamps all on her own and quite unexpectedly. She has often ordered me to bed with my sissy accessories charged up and left on to be used by her in the morning as my alarm clock. And being in a part of the world 5 hours behind her this makes for quite the early morning wake up. In fact I have been called upon to be up early on so many occasions that I rarely sleep past 6:30 am anymore. The other things about these toys is that they are far less limited in where they can be used. Princess Annie has taken great pleasure in the past in sending me out on errands with a plug in my ass under her control. Just imagine trying to have a conversation with a mechanic or sit through a movie while a giant butt plug is stuffed up your ass with unexpected spikes in the intensity of its vibrations. I promise you it is very distracting and more than a bit nerve-wracking. We have also experimented with an distance-controlled shock collar and during the pandemic I acquired I think Princess Annie’s absolute favorite piece of equipment of mine, a distance-controlled fuck machine. She has left me on my hands and knees, face buried in a pillow, for actual hours while her relentless, tireless, mechanical cock plunged in and out of me. The things about such a long fucking is that it doesn’t end when thrusting stops, it leaves your ass so loose and wet that it takes days to recover and in the meantime there is nothing you can do about the unpleasant wet spot that keeps forming in your underwear.

The introduction of diapers into the play kit also introduced a new dynamic. With being a sissy, all of the satin clothes, the panties, the dresses, the make-up, comes a certain level of feeling made up and better than before. In my experience only so much shame can come from that. Yes, I might look ridiculous to others and not sexy in any way, but that feeling is still there. Diapers have no such redeeming quality. It is impossible for me to slip on those bulky, crinkly, uncomfortable things and feel sexy about them. They induce an instant feeling of intense shame. I’m wearing underwear specifically designed for me to relieve myself into. Princess Annie knows this, understands this, and LOVES this. At this point I have also acquired locking pants for them, because where is the fun in making me use the diapers if I can just take them off immediately. I have spent hours in used stinky diapers that I have been unable to take off. And you don’t stay horny over that length of time, it comes in waves and that makes the shame so much more intense. This is also how I have come to know that scat play is one of my absolute hard limits.

And finally the sploshing, the glorious sploshing. I have had many conversations with Princess Annie about how much she loves making her subs get messy. A less common fetish that is turns out the 2 of us have in common. And eventually I was subjected to such treatment. If I had to hazard a guess and what Princess Annie would name as her favorite session with me I would say it was when I lined my room completely with pink plastic, forever dubbed my “Dexter setup” and prepared lots of slimy items for Princess Annie to cover myself with as she took charge of my fuck machine. Imagine raw egg and syrup running down your body while a chocolate pudding covered dick slams into your sissy hole before you have to clean it off with you mouth. I don’t think I have ever heard Princess Annie laugh harder at me.

There have been many other ways that Princess Annie has flexed her power over me and I am sure that there will be many more in the future, but for now these are some of the more memorable ones. The common thread among them all is that they bring such great amusement to Princess Annie and the “Good girl” that comes at the end of being subjected to them makes it all worth it every time.