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Feminization and My Sissy Maid Trio

As well as spending an entire podcast episode talking about Feminization and Sissy Maids, I’m also releasing a new session for Prissy, my blushing Sissy Maid.

Mirror Training is an explicit session for oral and anal training with large, cock-shaped toys. Though you can choose to listen to it as pure entertainment, or a visualisation.

To celebrate this release, you can pick up the Prissy Trigger Setting for free with any other purchase. Just enter the coupon code PRISSY at checkout. Take a look at some of my favourite Sissy Maid sessions.


Welcome to Episode 9. I’m going to chat a bit about feminization, and then go into talking about the Book of Expectations, and how it relates to the three maids. For describing the three maids, I’ll put some space between Prissy and Pixie, by describing Margaret in the middle. Well, not actually in the middle. You’re not getting a tawdry threesome story told to you. Though I do love a tawdry threesome. Let’s get back to the point… but first, we’re going to start in with feminization.

Why Femdom Mistresses Love Feminization

I’m sure you’ve noticed that while FLR is definitely my focus, my fetishes are here and there and everywhere. And I definitely go through stints of really craving and loving a certain thing, while something else goes on the backburner. I would say that feminization, like really focussed feminization is one of those things. Now, if it’s someone who kind of handles all their own stuff, you know… just shows up that way or adds it in… or naturally just has lingerie underneath, and I get to admire it… that’s fine. It takes no emotional, mental, whatever energy from me to appreciate that.

Now if it’s something that takes a bit more on my part, like Prissy… who we’ll get to later, who is reluctant. But it is that emotional, and physical as well, energy poured into it. Now, many a time I will pour away, because it’s fun and it’s exploring and doing. But I couldn’t do that every single day.

Just being honest with you… but there’s very little that I could do every single day. Even in regards to the FLR, there are times it just needs to run. It needs to be this naturally submissive partner, and not someone that I don’t know… needs broken. In. Every day.

Other than drinking coffee and getting dressed I don’t think there’s anything I’m willing to do every day. And if I’m on holiday I don’t even do both of those.

Okay, so for feminization, I gotta admit, I do like all the different parts. You can give me the Prissy type who’s, you know, embarrassed and forced and whatever. You can give me the Pixie type, who loves it. Loves it, you know? The more… petticoats I slip on them, the happier they are. I have a thing for bells. Ages ago it feels like now, I saw this man. Still identified as a dude, dressed up in the most wonderful sissy maid outfit ever. And part of what got it for me were these panties. They were satiny and they were gathered in the back, so they nicely outline both sides of his nice round bottom, and they tied on the side with very huge, overdone bows. And you could see them because while wearing a skirt there are enough layers that you could definitely see these panties. And then it had bells, each side had these little jingly brass coloured bells. Something about that just sells it for me, constantly. If you ever want to, if you ever want to seduce me or someone like me, just show up in a pair of those panties. Nothing else, just those. That way you can see and hear the bells.

Okay, so I like that side. I like the all-in guy. I like the “Oh no, don’t force me!” guy, I’ll play with that. But there is another bit that I’ve totally fallen for, and it’s a bit more difficult to describe. And I think it’s because you don’t often run across this particular flavour. It’s the guy that he naturally believes that women are superior. Period. And when he has an item of the clothing on, let’s say something as simple as a linen robe, wrapped up in it, tied in a bow because who doesn’t love  a bow, right? So for this man, wearing this bit of, even if not overly feminine, but definitely belongs to a woman clothing… he doesn’t feel disgraced. Not a bit. He knows he’s being honored, right?

But, here’s the fun little headfuck for him. He knows he’s not worthy, because he’s a guy. So, a bit of imposter syndrome I guess, going on there. But I like that. I have, across my play, run across a few gentlemen like this, and… oh, it’s just alluring, but it’s alluring in a way that’s kind-of hard to describe, because you can’t fake it. If that’s not your natural bent, and here you are dressed in my robe, you’re either going to fall into the “Prissy, oh no I’m so embarrassed, why are you doing this to me?” or the “Pixie, oh, look at me. Look at what I’m wearing!” category. And then if it’s absolutely not your thing… you’re not feeling honoured. You’re not feeling disgraced. You’re just, you know, a man… wearing my robe.

Anyway, so feminization for me is a bit of that. I have fallen before for where it wasn’t an ongoing relationship, like a romantic one… but a friend one. Going to the book store, going out to coffee, you know… just out. Two ladies doing their thing. That is satisfying to me, too… but that falls a bit different from the gathered satin panties, you know… with the bows and the bells.

My Take on Sissy Maid Hypnosis

Okay, so… for the Book of Expectations, in regards to the maids, each maid has a page in the book. And each maid sees that when they go to their dressing room. There’s a very specific trigger for each maid, and in some of the sessions there is a bit of going back and forth between the proper one, and the slutty one, so you do have to have… if you want that kind of play, you do have to make sure that these different personas are really ingrained in there. That those word runes that house the triggers, they are burning bright.

So let’s start with Pixie. Pixie is my flirty French maid. I like to think that Pixie admires the beefiness of a man, as much as the allure of a sensual woman. I imagine that Pixie’s type of guy is all like… washboard abs, and chiseled cheeks. A bit of scruff on those so he’s not too pretty. You know what I mean by the too-pretty guy, right? Okay, and bright baby blues to top it all off. And of course, Pixie’s type of woman is sensual but stern, and willing to put up with Pixie’s antics… well… not just put up with them, but encourage them. Even if it seems like she isn’t.

Now Margaret is very much the lady’s maid. If you’ve watched, like, Downton Abbey or things like that, you will know what the lady’s maid is. She gets things done. She makes her mistress’s life better. Not saying Pixie and Prissy don’t, but Margaret just keeps it going. And I love that. I love the contrast. They’re both very welcome to have space up their in my headspace.

And Margaret also has this devotion and love and gratitude that creates this relationship that’s very intertwined and genuine and warm. I would say it’s similar to having those friends that… it’s the ladies day, and just going out and doing tea or what-not, but it’s in the maid form, with Margaret.

Margaret definitely knows her place, she definitely follows the rules and tries to make sure others do the same. And I like to think that if Margaret walks into the bedroom, you know, in the morning… and she finds Mistress in a tangle of sheets and a tangle of bodies, that she just… goes about her business and tries not to look.

Finally, we get to Prissy. I know Prissy and Pixie perhaps… I should have picked names that are a bit different, but Pixie is just pure flirtation, right? And Prissy, there is something about Prissy that you know… this man has been forced into the sissification, right? And obviously, the focus of Femdom Hypno, it’s not all about sissification. I do have these three, but it’s just because, they’re so vivid and real to me, I had to make sure I was bringing you into the headspace with them. So Prissy, yeah, he is the… or she is the, I just go back and forth because, again, it’s just the mindfuck, right? I suspect Prissy really, really wants to be dressed up, but just can’t make peace with it. So Prissy is the one that gets into these outlandish outfits. Not even close to practical. And, overdone. It’s not subtle perfume, it’s not the light pink lipstick. It’s pure, on. And it’s also making sure that Prissy is forced to see themselves in the mirror. Face themselves, and be seen by other people. There’s a good bit of… I guess you would call it humiliation. But is it still humiliating if I truly believe that Prissy wants it? I like blushing, and Prissy is very easy to make blush. Pixie’s not.

So that’s it. There are these three maids, and like I said, there are some sessions where you kind-of go back and forth in their story, and that jolt of difference, it’s good for the soul. But yeah, I’m not all about feminization, and I do believe it can be a base layer that stays all the time, and that’s fine. But it can also be like other forms of play, like puppy play, or… having that evening that’s all about welts and bruises and lines. You know, using every ouchie implement possible. Things like that, the intricate ropes, right? That, you ‘re not wearing clothes, you’re just wearing the knots that I’ve put around you. I like that too. And I know you do, as well… because I hear it, all the time.

So, today’s episode was a bit longer, but I do want to hear from you. Tell me what you would love to experience in this realm, that I haven’t touched on already. And if you’re feeling, I don’t know, prolific or creative, if you send me… let’s say 800 words. 800-ish words on the topic, and I turn it into a session, I will just give it to you. And I probably will give you a personalised version.

Your task for today is to think about the kind of Feminization that you would both enjoy, and not enjoy. And your Permissive Circumstance is, if you can make a list of things that you would love or not, and this list has at least 25 things on it, in under… should I say five minutes? Or two minutes for an extra challenge? I suppose it depends on how fast you can write. Well, then you have my Permission today, for release.

 Hear from you soon. Bye for now.

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