Oh my! You are such a pretty sissy! You look gorgeous, as I always knew you would. I’m so excited to find out that you are listening to all of the sissy training tips on The Weekly Hot Spot BDSM kink podcast that I do with Ms Erika. Now, it’s time to make plans for the next phase of your sissification or coerced feminization.
What Exactly Is A Pretty Sissy?
So…what to do with a pretty sissy like you? There are so many possibilities. That’s at least part of what makes our relationship so exciting. Okay, let’s be real. A huge part of the fun is all the shopping, because girls love shopping! Add the thrill of domination and power exchange, and, oh yes, that’s the best!
So what is a pretty sissy, really? I think to qualify as a pretty sissy, you have to have a certain aesthetic. If you’re already in one of my sissy training programs, then you know what I mean. It’s about clothes, sure, but it’s not only about fashion. Style includes the total package. For many of you, makeup can be a challenge, but I can guide you so your makeup is cute and sexy. I often sort of lean into the sissy bimbo aesthetic because I think that’s super hot!
When you qualify as a pretty sissy, we should definitely talk about what we’re going to do with you next. As I said, there are lots of possibilities, and I think we should discuss at least the most obvious ones.
What Comes Next In Your Feminization Journey?
The first question I think needs to be answered is: Who are you going to serve? A sissy is no one without someone to be dominant over her. Obviously, I know you’ll serve me, as your Exxperienced Mistress. But will you be a one-Dominant person sissy, or will you submit to anyone who’s willing to take control of you? Or something in between?
I think it’s important for me to decide if you will serve women, men, or both. Given how beautiful you look, I think your beauty would be lost on men alone, so we’ll definitely let you serve other ladies besides just me. But men deserve a pretty sissy sometimes, too, so why not let’s have you serve both? I think that would be the ideal arrangement for you.
What Else Does My Sissy Need?
What else might you need? Oh, I bet you’d love a little sissy humiliation, wouldn’t you? I know you think you wouldn’t, but something tells me you would. It’s probably the fact that your little clitty is getting hard in your panties at the thought of being laughed at by your Mistress!
Hmm, what else can we do? Do you need to be totally emasculated? Not just humiliated, but stripped of your manhood entirely? I’d say it couldn’t hurt. I mean, you don’t have a whole lot of it left right now, anyway. What’s removing the itty bit that remains going to hurt, after all?
Ooh, I had another idea. I could cuckold you as my pretty sissy. I think you’d make a fantastic sissy cuckold for me, with all that entails. And what does that entail? Hmmmm, I’d say that’s probably a blog for another time. I think you have quite enough to take in right now, so I’ll end it here.
Until next time, my pretty sissy. Hope you enjoy the outfit you’re wearing for me! If you have any questions or concerns, leave me a comment or give me a call. I can’t wait to talk to you about your feminization process!
Your Experienced Mistress,
Ms Olivia
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Not into guys Ms Olivia but what about with the other mistresses? Ms Erika/Ms Delia/Ms Alyssa/Ms Daphne and Ms Madi showing me of how you dressed turned and made me your sissy with HRT in my shakes as I didn’t know as I became more girlish with growing breasts/girlish petite body/facial features/feminine arched eyebrows? I had bad bad bad cold/sore throat last 2 weeks-with 2024 here it’s time to finally be the girl I was always meant to be! Ordered 4 dresses and can’t wait to see how I look in them! Also starting strict diet to lose weight so I can fit into women’s clothes/dresses and get rid of ugly fat gut! Definitely plan on calling in 2024 on weekly basis-just need to find day/time and be consistent with this. Soo can’t wait to have you turn me into your girl with lipstick kisses on my cheeks!
lots of lipstick kisses for you!!!
That is what our academy does. It removes any semblance of masculinity and replaces it with femininity. After months of dresses and makeup any masculine traits will be gone.
xxxxxxx
Yvonne
Well …… remember there are several dances to make SURE those masculine traits are fully gone and your feminization is complete.
Can the girlly grapes ???????? be shrunk? I think mine have a tiny bit but not enough to please me
I just got a dress tonight I am going to dress up as a woman crossdresser some times now not just on the beach in panties
including the girly grapes ?????????
I’d like you to dress me up like a schoolgirl who’s trying to look a bit slutty. Innocent looking, with pigtails, nice skirt and blouse, but bold makeup and lots of deep red lipstick.
I’ll be crying and pleading not to humiliate me, but secretly will be getting excited. Then once you’ve made me up into a little slut, you’ll have a special friends over and you’ll make me take care of him. I’ll beg you not to, but you’ll push me to my knees and make me pleasure him. My lipstick will get all smeared, so every few minutes you’ll have me clean up a bit and re-apply it. Good thing I’m already on my knees because I’m so excited I don’t think I could stand.
By the time he’s done with me my face is a smeary mess, but you’ll make me clean it all up, then re-do my makeup so I can take care of your next friend.
slutty sissy turned into a cock slut — that’s such a great fantasy!
ok so we must know that there is a way to bimbofication. Are you.going to make me a bimbo or s sissy maid ?
Hmmmmm making someone a bimbo, sissy maid or even a sissy slut depends on the individual, our connection, what feminization training I’m doing, etc.
So Miss Olivia you plan what type of sissy you make?
Sometimes I plan the sissy training … if I already have a relationship with the sissy.
Otherwise, we talk and then I plan.
cool ???? I kinda like your style in a corset of course you would lock ???? me in chastity personally
I just restarted my sissificitation I had purged all I could find . Then got the correct panties then correct swimsuit bottoms
then I received the pantyhose
now I have a dress.
I have perfume in the house everywhere
I also have a brand new whig
and sunglasses that l haven’t purged
I have sucked cocks or should we call them dicks? while in panties and chastity
Ahhhhh any sissy or crossdresser has usually done the purge cycle…that makes me sad … plus some cute things and fun toys get tossed. 🙁
I’m glad you’re replenishing!
Just last Saturday I received an amazing gift. A UK trans women who is married to a CIS woman is leaving the UK
and moving to Portugal & is selling their home in America and leaving lots of clothing and stuff. I now have a full wardrobe
WOW that is awesome!
oh oh Ms Olivia,
Pretty sissy twirlllll twirlllll twirlllll
pretty sissy curtsey curtsey curtsey
pretty sissy swish swish swish
pretty sissy kneels for suckie
pretty sissy bends for cookie
pretty sissy serves for pleasure
pretty sissy here for ladies
pretty sissy loves humiliation
pretty sissy locks her cage
pretty sissy lives in chastity and cuckold heaven
Twirlllllllll for us sissy belinda! Lift up that pretty skirt and show me your chastity under your pretty panties!
yes in a new style and so far it’s all free except for shoes which are for both sides of me
Mistress Olivia,
Really ADORE your blogs and podcasts, thank you so much! I’d love to schedule a phone session with you VERY soon, and will. ????. Daphnegurl
Ohhhhhh Daphnegurl thank you so much — we do have a very good time on the podcasts and wow, we’ve gotten some really fun guests.
I would LOVE to talk with you !!!!
Oh Ms Olivia, you know how to touch all of my buttons! I soooo need to call and talk to you and or Mistress Erika about what a sissy pansy nancy boi I am!
Thank you for all you do for us gurls!
*curtsy*
sissy laci
giggles
We agree! Although I feel like we know you and we talk about you on the podcast when we do a sissy or feminization episode.
In fact, I’m using one of your comments for the Popular Sissy Fantasies episode we’re recording shortly!
I am now seeing gender benders in the real world.In Florida partial crossdresser or sissy in public. not these gender benders are not done
up all the way.
Personally my clitty shrinks under humiliation.In my new wardrobe is a Cami very tight and shows off my hard nipples. Orange can wear this to beach with the orange thong panties &; a short wig on top of my head shaved when summer gets here
But that’s just future sissy cock sucking adventures.For now will be going soon wearing a new dangle heart belly piercing. I could e Mail you of the chat places I have found T Girls message me