Sissy Confession with Kassidy

April 15, 2025 by femdom

My sissy confession is that I was one of those girls who use to dress my brother up in girl clothes when I was younger. I would manipulate him into those frilly little princess costumes that I had in my dress up box.
It use to be so funny cause I would get him to come into my room and say lets have a little party and course he would say yes. He loved to dance so I knew if I played some fun dancing music that was a good start. Then I would say oh wouldn’t it be fun if we got dressed up like we were going to some club. Course in my head it was some super girlie club. So he would sit down and I would start putting on some make up. Then I would swish around in my skirt and go hey wouldn’t you like to swish around in a skirt too? Yes was always the answer. So see it was super easy to get him into girlie stuff.

I always wonder if those moments made my brother a sissy boy? Well I hear some stories when I am on the phone with sissy boys and they are all my sister got me into being a girlie boy and my sister did this. So then its like could my brother be calling up phone sex girls telling them how his sister forced him to wear girls clothes and now he is a sissy boy? OMG if my brother only knew I was a phone sex girl who still forced boys into girls clothes. Hah that’s kind of funny isn’t it.
Well love to hear you sissy confession especially how you got into wearing women’s clothing.

Just ask for Kassidy when you call the number below

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Become Dani’s Phone Sex Sissy Daddy

March 25, 2025 by femdom

Daddy will you play dress up with me? Was thinking it would be super fun to make my daddy a phone sex sissy boy!

We can break into Mommy’s make up and do each others hair. Well I guess more you do my hair cause you don’t have much. Ooo what if we got you a long blonde wig so you could match me?

I promise not to make a big mess of your make up daddy. We could do like a spa thing where I give you a mani/pedi. Would you like sparkly pink nails Sissy Daddy?

I think sparkles are the best!

Then we can go into Mommy’s closet and I can really get you all pretty sissy daddy. I wanna put you in everything pink cause that color is just so much fun.

Please come be my phone sex sissy daddy. We can have so much fun together. I don’t mind if you wanna do even naughtier things than just dress up. I was kind of thinking we can do that stuff in those movies you like. You know the ones where the pretty guys dressed up as women kiss other men’s dicks.

Your baby girl is ready for you!

Just ask for Dani.

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Sissify your Bath Time

February 5, 2025 by femdom

Hi Guys n gals. Now being a girl with long hair one of the things I get to enjoy is great hair products. Course that got me to thinking that it sure is a super easy feminine thing for those closet sissy boys to do when they can’t get all dressed up. So just wanted to share that for those closet sissy boys that are looking for a little something they can do between dress up session and sissy phone sex calls. It all starts in the bathroom with your bathing routine. That’s right guys time to sissify your bath time.

Shampoo. Getting a great smelling shampoo and Conditioner. Right now I find that Fructis has some yummy scents. Some are rather super girly and the best part is they have a whole line so you don’t have to stop at your sissified shower you can continue right on to your gel and hairspray.

Body wash. You could grab a scented man wash but honestly you will smell like every other man in the elevator. Rather boring. More interesting if your the only man in the elevator and they are all sniffing around wondering where that sweet floral scent is coming from … you. So go indulge in a beautiful woman’s body wash. There are some that are a bit more unisex if you have to dive into this one more slowly or if your daring go for a perfume scented one. You will be super girly when leaving the shower.

Deodorant. Why wear those masculine man deodorants when you can wear a super sexy woman’s deodorant. Trust me you will feel extremely feminine the minute you start gliding it on. Especially if its on freshly shaved underarms. *hint*hint* Then through out the day when you lift your arms you will get a sweet smell of that sissify deodorant.

I hope you guys enjoy my girlie tips.

Kassi ~ xox

Just ask for Kassidy

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Female Transformation Hypnosis with Savannah

January 5, 2025 by femdom

Often get asked what someone can expect with a female transformation hypnosis phone sex session well everyone has their own end results they want from a sissy hypnosis session. For some its building a hypnotic fantasy around transforming them into a sissy slut guiding their trance into what they would look like at the end and what fun they will have being a woman. While some its all about putting the hypnotic triggers in place that will have them working on their own form of female transformation.

For one sissy boy its all about the latter.

Putting those female hypnotic triggers within his subconscious. Building upon them so that the process. The desire to be a woman is unmistakable. Making it so he can not hide who she desires to be.

Some of the hypnotic triggers are rather simple and any sissy boy or cross dresser would love them such as making him want and need to wear panties all day long. Simple enough right?

While others prefer to work on their behavior. Getting rid of those annoying what society deems mannish behaviors and replacing them with sexy, sultry more feminine ones. (What those behaviors or traits are is up to you.)

Each female transformation hypnosis call pushes him that much closer to his ultimate desire… to be a stunning woman.

Do you have an ideal image in your mind of what you want to be as a woman? Are there behaviors or traits you wish you could me less mindful of? Traits that just become second nature like breathing? Then perhaps a female transformation hypnosis phone sex session is what you have been looking for.

Please note an erotic hypnosis session does require more time and 30 minutes minimum is recommended this allows for you to fall under my sensual trance and time to explore your fantasy.

Look forward to transforming you just ask for Savannah!

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Sissy Phone Sex Fantasies with Vintage Girl Maxine

October 15, 2024 by femdom

Ok if your a cross dresser or sissy boy looking for a phone sex girl who is into the latest fashion trends I am really not gonna be your girl. I could careless what Vogue has to say about what is in trend this year. What you will find is a girl who is very much in tuned with what looks good on her sexy body. I know the styles that work for me and I will rock that shit like no ones business. From hitting the local thrift stores to surfing retro clothing. Pretty sure nothing I own is from this decade haha.

All my clothes come with a story and I fucking love it. Which is also why I love chatting it up with your crazy sissy boys on the phone. I mean you guys have a wild story too. From why your hiding your secret sexual fantasy from the other half all the way to what style of clothes you choose.

Are you someone who wants the latest styles or do you prefer the classic retro looks?

Really love to hear where you shop and if you dare take yourself to the thrift stores to shop for girlie clothes. I mean to me sissy phone sex fantasies are all well and good but if you cant venture outside the box just a little then where is the fun.

Need a girl to push your sissy limits?

Suppose that is where I come in the one willing to push you to that point of going outside your comfort zone. To make you do those things you wouldnt normally. Like go buy make up at some store. Sure you can come up with a lie as to why your buying it.

So like I said I wont be the girl to talk over the latest fashion trends but I am more than happy and well eager to chat with you about the styles of years gone by and well of course your kinky fetishes.

Just ask for Maxine your vintage loving phone sex girl.

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Pretty Phone Sex Sissy Maids with Porscha

July 20, 2024 by femdom

The down fall to wearing sexy panties is the washing of them. Can’t toss them in the washing machine for that will just ruin the delicate lace. So your left with having to hand wash. Normally I would be all over that but the hours it takes when you have a hamper full is well overwhelming to say the least. I did happen to discover a solution ~ a pretty phone sex sissy maids!

Yes apparently you petticoated wearing sissy maids will enjoy standing at the wash basin performing all sorts of laundry tasks. Well any household task can be accomplished in your over exaggerated maid look from the stiletto heels to the black fishnet stockings and puff sleeved black or pink maids uniform. Mind you I prefer to have my phone sex sissy maids in a uniform that pins up in the back so can see those put satin panties all the time.

Yes a french phone sex sissy maids uniform will do nicely.

Why only show those pretty girly panties off when you are dusting the low areas of the home. Since discovering the joys of a sissy maid my life has become so much easier. I get to savor more time doing what I like. Which is laying back relaxing reading a good book and well the man dressed up like a female maid enjoys their thing too. So really its one of those win win situations.

I can even snap my fingers and that sissy boy will fetch me a drink. Life is good.

My laundry never looked so good.

Ready to play with a few more kinky phone sex sissy maids. Who is up for the challenge of cleaning for a mature women?

Porscha

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Sissy Boy Masturbate for Mommy

June 10, 2024 by femdom

My name is Jennifer but you can call me Mommy. For I know you sweet sissy boy have been looking for a phone Mommy for far too long. Someone you can get all dressed up in front of and well masturbate for.

This phone mommy loves her sissy boy’s to masturbate for her.

I know it’s hard not to get all excited like that after hours of primping. Hours of snooping through Mommy’s closet. I even let you play in my good makeup. The stuff I would normally smack your bottom for but this is a special occasion.

For everyone is out. They have left us all alone. I am even letting you stay up later than you should. No little interruptions. Just you and me and this collection of oh-so-sexy things.

Where do we begin?

Picking out the outfit you will be masturbating in?

Or do we start by Mommy doing your makeup?

I know the possibilities are endless right now and your head must be swimming. Why don’t you just come sit on Mommy’s lap and let me comb your hair while we decide together? For you don’t have to make those decisions by yourself sweetheart. Mommy is here to help you.

Perhaps I will start with you watching me put my make-up on first. For it’s only right that I look just as pretty as my sissy boy.

Well sweetie Mommy Jennifer is here to have some fun with you and most importantly sissy boy let you masturbate for her.

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Teaching Sissy Boys to Wear Stockings

May 10, 2024 by femdom

If your going to be a phone sex sissy boys then one of the items of clothing you are going to get to know is stockings. They happen to be one of my favorite pieces of clothing. Nothing compares to the feeling of your legs when they are encased in silk stockings. You will want to touch them all day long.

Especially if you are shaved.

Now I know as closet phone sex sissy boys you are not quite ready to dive into shaving your legs. Or at least you can’t pull off the excuse of I am doing it for swimming when you know your ass isn’t seeing a pool. Well don’t worry your phone sex girlfriend Kassidy is here with a few tricks to help you. For those silk stockings have one downfall for hairy legs. You see it!

Well, you are going to find a thousand different ways for sissy boys or phone sex cross-dressers to hide your leg hair. This is one that I stumbled upon and found to be less evasive than bleaching your leg hair. It was buying 2 pairs of dancer tights in your skin tone dull finish. This will enable you to wear sexy nylons, pantyhose or even stockings over top no matter how sheer. Course you won’t want to hide your sexy panties under those tights so put them on over top.

So there you go a sexy trick on how to hide your leg hair without shaving or waxing and still be able to wear those nylons and pantyhose.

Love to have a sissy girl gab fest with you. Share my other secrets with you.

Just tell the dispatcher you wish to speak to Kassidy and maybe have a pair of stockings or nylons on already so you can start enjoying that silky feeling.

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Sissy Phone Sex Confessions

April 25, 2024 by femdom

I have a bit of experience dressing men up in woman’s clothing and we are not just talking sissy phone sex call experience either. See I wasn’t always a chick with a dick. I started out much like you. Venturing into my mom and sister’s closet to steal those clothes, I figured they wouldn’t miss. Then waiting patiently to have the house to myself. So that I could put on my newfound girlie items and dance around.

So I know all too well the excitement sissy boys get when their wives or significant others take off for a week or so and you get to do what you been dying to do.

Get girlie!

What is the first thing you do?

Is it put on some sexy lingerie and get a pretty drink while you do your nails?

Or are you more a put on those panties and drive to some town so you can buy some sexy things to make the most of your time of sissy freedom?

Well now it’s time to up the fun by giving this tranny a call, lets have some fun now that you’re all dressed up. Venture into some of those naughty sissy phone sex fantasies you’ve been thinking of.

Time to share and well explore those wonderful kinky fantasies you been keeping to yourself.

Dru

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Sissy Cock Sucker Sucks My Boyfriends Dick

January 25, 2024 by femdom

Now there is never any guess what this one caller is in the mood for. Sure I make him tell me he wants to be a sissy cock sucker only cause I picture him squirming around in pretty panties while he tries to find the words. But it’s the girlie voice he tries to have that gives it away. “Mistress Courtney I um its ahh your Sissy Janie here to suck some cock for you!”

Like he has watched one too many drag queen YouTube clips to get that perfect bimbo voice going. It always has me giggling cause it’s not quite there yet he bounces between his masculine voice and this high-pitched fairy wanna-be voice. Nice try though and I know eventually you will get it.

So course knowing he wants to be a sissy cock sucker for me I will not hold back. I ask Sissy Janie what she has on for me. What pretty little outfit did she find or buy for that special cock she is about to swallow. It’s usually something pink. Super Barbie doll pink lips too.

The cock in question that Sissy Janie will be sucking will be non-other than my boyfriend’s cock. Sure I could find some random guy at a club but why not have her give my boyfriend some pleasure?

The best part is watching this sissy cock sucker slurp back on my boyfriend’s cock. Sure that might not be everyone’s idea of fun but there is something so hot about looking into my boyfriend’s eyes knowing he is getting pleasure from an eager cock whores mouth.

Wouldn’t you love to slurp back on my boyfriend’s dick? Well, you can just give me a call. Tell the dispatcher you wish to speak with Courtney and let’s have you being one nasty sissy phone sex cock sucker like Sissy Janie here.

There are no limits and no taboos so who knows where things could end up!

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