I have always been interested in the concept of sissy transformation–the process of turning a regular, albeit submissive, guy into a total sissy. Now that I’ve met you, I see I have the perfect candidate for this sort of thing. You’re a man in a position of authority, but you have secret submissive desires because you sometimes need a break from that position of authority. And as for me, well, I’m in the mood to turn the tables on you.
You don’t have any sissy desires (yet). You will, eventually, but you aren’t aware of any of this just yet. I’ve just informed you we’re going on a long weekend together, and you’re very excited, thinking we’re about to take this relationship to the next level. And we are, so to speak, just not in a way you could ever imagine!
A Vacation With Your Soon-To-Be Mistress
You packed your suitcase last night and made sure you had everything you need. But I’m devious sometimes! I switched it with one that’s full of nothing but the girliest, frilliest, most feminine outfits you can possibly imagine. You’ll be none the wiser until we get to where we’re going and you open it, in search of something.
I have all the things in there I want you to wear, from panties to dresses and accessories. There won’t be a thing you can do, as there won’t be any male clothing to be had in our little cabin in the woods. You’ll either have to get naked for me, which will be rather chilly for where we’re going, or you’ll have to go en femme. I’m pretty sure I know which one you’re going to have to choose….
Feminization Through Necessity
In order to keep you from freezing, your sissy transformation will be hurried along. You’ll have to wear those girly outfits. You simply won’t have a choice! But I’ll promise when you put them on that it’ll be our secret. No one will ever know. (Yet, anyway).
The name of the game is feminization, and this experienced Mistress is the best at it. If we were at home, your sissy transformation would take much longer. But when you’re feminized through necessity–the need not to freeze–a lot of the nonsense goes out the window. You’ll simply shut up and wear the clothes.
Furthering Your Sissy Transformation
Once you’re dressed, I’ll keep my word about not letting anyone know (for now). This, however, means we won’t be able to go outside. So if we’re all cooped up in the cabin for the weekend, what is there to do? Furthering your sissy transformation, of course! Every stylish sissy needs to know how to do her makeup, deal with wigs, and walk in heels. You have a lot to learn and a very short time in which to learn it.
You’ll become my sissy slave in no time. Before the weekend is over, you’ll be begging me not to make you change back into men’s clothes when we get back home. And I will very happily oblige you with that!
Once your sissy transformation is complete, what happens then? Oh, there’s only one way to find out. But here’s a hint: It’ll probably involve a strap on. Just sayin’. Check out the BDSM kink podcast that I do with Ms Erika. There are lots of sissy training and feminization tips including episodes like this one on sissy sex!
If this sissy transformation roleplay sounds like something you would enjoy or if you have sexy transformation scene, give me a call! We’ll have a lot of fun! I can’t wait to hear from you!
Your Experienced Mistress,
Ms Olivia
Podcast: Play in new window | Download
Subscribe: RSS
Well you hardly had to trick me. I came willingly to wearing dresses. I even loved it when you put me in chastity. Enrolling me in the Madamoisele Academy was pure heaven. The bridal curriculum was so right for me.
xxxxxx
Yvonne
I sure didn’t need to trick you that’s for sure. You are the willing bride and now it’s just a matter of making sure that any hint of “masculine energy” is removed. That’s what that dance is for – just to make sure you are progressing nicely on your feminine journey.
O. M. G. This!
What an incredible coerced sissy story Ms Olivia! Once I saw the title I just HAD to read it through to the end and found myself with quite the tent.
This is the stuff of dreams!! What a hot hot hot predicament he finds himself in! All under YOUR control! I love love love the way you trick him so he has no choice. So clever, so diabolical, so HOT! I just know that every person reading this (including me) will wish this would happen to them. Who wouldn’t wish that after reading this!?
I can’t think straight now… going down… mind turning to mush. Mmmmmm. Thank you Mistress for sharing such a hot story!!!
giggles
Your MIND might be turning to mush but …. looks down and smiles …. there’s a lovely tent on those panties! grins
You know me … oh yes sweet, sexy, loving … AND AND AND smart and diabolical!
LOL
Ms Olivia❤️ Inserting myself into this saucy sissy scenario…(since I’m not inserting myself anywhere else) you are taken aback when you open my grip only to see it is already crammed with dainty delights of feminine frou frou! Satin, lace frills…an adorable over the top sissy dress, heels…the works.
“That little sneak!” you think to yourself.
The next day as we are getting ready to leave you announce, “change of plans dear”.
“We won’t be going to the cabin. I’ve booked a room at the Ritz hotel in the Big Apple.”
“We’ll have soooo much fun, out and about, taking in a show, dining out, strolling the streets!”
I don’t know whether to s**t or wind my watch!
Your plans are coming to fruition ever quicker than you had imagined Ms Olivia!
Oh my !!
Since it’s the Ritz – we’ll have to do High Tea which is going to be quite the display since you’re in those ruffles and frills. LOL
My first High Tea at the Ritz was in Washington DC – it was actually kind of intimidating and then VERY fun!
Oh yes Ms Olivia. I will be sure to sip with pinky extended….NO! Not THAT pinky!????
laughs and laughs
SIP
SIP
SIP
When I glance around the room I notice the ladies are looking at me and they all have their pinkies extended…but they aren’t holding a cup of tea!! What could that possibly mean?!????
They’re looking at you and laughing, aren’t they?
Let’s seeeeeee …. I wonder what they’re talking about — you want me to ask them?
I can find out for you — I’m happy to do that.
hahahahahaha
It’s probably for the best. I’m liable to faint from shame mincing over to their table!
hahahahaha — shame for you is a good thing!
Oh I love this
Mistress Olivia. My clitty is already tingling thinking about the delicious lingerie, petticoats, and dresses not to mention the sissy collars, plugs, etc. and what will happen to me once en femme.
Ohhhhhh what WILL happen to you sissy donna? Why ….. anything Mistress wants!
grins
Right?
wow. this is so amazing I dream of this happening to me. I am struggling so much in my chastity cage right now because of the story.
giggles
Well ……. put that energy to good use and put on that cute lil secretary outfit.
Please xoxo
love it so much I’m so sorry comments are not working…I have written comment and it doesn’t appear.
wanted to say love it love it love it….
you’re so amazing!
Hi Casandra!
Comments ARE working … the delay is on my end.
I have comments set so they don’t “automatically” post. I do that for several reasons. I want/need to make sure the comment is appropriate, not against our TOS, etc. I also respond to each comment as I approve it – this means I don’t miss comments by accident.
This causes a delay in seeing your comment post. I approve and answer asap but it’s not always right when they appear – how long it takes me to reply will depend on a variety including: calls/sessions, podcast work, blog work, other behind the scenes things that I do, answering emails and Skype message and all kinds of other things.
Rest assured I got your message and THANK YOU !
Oh Mistress, this is like something out of my most beautiful dream. I’ve always wished I could at least dream about it and wake up excited…
You have such a beautiful and teasingly subtle way of describing a story…
It excites me to think of being forced to dress like a woman, like your sissy whore or maid, and serve to your complete satisfaction.
I’d just be terribly sorry when the weekend was over…
Oh my goodness, thank you for a beautiful article, perfect audio with a beautiful voice…I have no words…I love it!
Your devoted Casandra!
Thank you so much, Casandra, for all your kind words! I especially appreciate you mentioning my “teasingly subtle way of describing a story” !! I’ve actually taken classes in storytelling, pacing, script writing, etc. So some of the “crafting” parts are deliberate and by design.
I guess I really DO like being IN CONTROL hahahahaahahahaha right?
grins
Mistress Olivia, I totally understand the approval process, I was just worried that the comments were lost, I’m sorry if it sounded like I was complaining. You’re an amazing storyteller and I love it. I love your attitude, sense of humor and humanity, kindness and dominance. It must be a pleasure to serve you and make you happy. And it’s even more wonderful to be feminized by you in the process, as you write here in the article. W????W.
Have a great day.
Oh Casandra, I didn’t mean to imply you were complaining, not at all! I’ve had others ask and it’s a legit question – especially since comments DO automatically post lots of other places.
Part of it for me is to make sure I actually SEE all the comments and make sure I reply – when they just immediately posted I missed replying to a bunch of them!
Hey … you have a FANTASTIC sense of style! I love the images you post on Enchantrix Empire !!!
Thank you, wonderful Mistress Olivia. ????????
lipstick kisses Casandra!
This needs to be our next call!!! I’ll try to say no resist and deny you dressing me as a girl but you’re to hot sexy and powerful to say no to especially with lipstick kisses on my cheeks!!!
Great post Ms Olivia!!!
Thank you so much carli cream puff – you know if my friends and I set our sights on turning you into our perfect sissy, you won’t have ANY choice at all.
grins
Goddess Olivia:
You would never have to trick this Sissy Gurl into transformation. In fact I would beg and beg and beg you to feminize and control this submissive forever. I want to live my life in lingerie, heels, skirts and dresses. Also, please teach me all I need to know about makeup ????, nail care and hair care / styling. Hugs ????.
Sissy slut,
Jizzelle
Add in some hot pink knee pads Jizzelle and you are good to go!
Live this way as the best cock sucking sissy!
OOOhOh Olivia my dream come true but let’s skip the cold weather Email me when ever you want to further my feminization and let’s do this for real