Feminization phone sex

Becoming Sissy Slut Cumilla with Savannah

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sissy slut phone sex

I don’t know this hypnosis caller by any other name other than Cumilla, his slutty alter ego that comes out when he goes under. Well, really, we are trying to bring out Cumilla more than just during a sissy slut hypnosis session. Building upon previous erotic hypnosis phone sex calls that will have that male side disappearing entirely and having him venture out into the world as Cumilla.

Last night’s session took a bit of a left turn, for we were talking about street walkers and breaking out into being that type of dirty whore. The male side told me how they had driven around town to find the right spot to work their ass a few weeks ago. When pressed about how that corner was working out. Well, let’s just say that slut hadn’t been back.

The male side prevented Cumilla from working.

Definitely couldn’t have that. So back under my spell, the sissy slut went and worked on the hypnotic trance that would have Cumilla venturing down to that corner once again and working that ass. Waving at the men and showing off those pretty fake nails.

Course it wont just end at waving to those potential johns.

Oh no Cumilla is there to work and become that sissy slut.

Savannah

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Strict Phone Sex Mommy Nancy

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strict phone sex mommy

Everywhere I look lately, all I see is naughty boys. Naughty boys that require some discipline from a strict phone sex mommy. Well I mean you all need some form of punishment but I don’t have enough hours in the day to dish out that level of punishment so for now we will only focus on those that are in need of some over the knee spankings.

What could make those poor boys be on the receiving end of my hair brush?

Well the last one it was rather simple he didn’t listen when I said no to him wearing my stockings. No you may not wear my silky panty hose. No I do not care how good they feel rubbing against your naughty bits. No those stockings are only meant to be worn by your strict phone sex mommy.

The joy I took while rolling those stockings down over his quivering thighs before making him laydown across my legs bare naked from the waist down was rather thrilling. With each smack of my wooded hair brush on his bare bottom had him whimpering. Hell he was making sounds with just feeling my arm raise up in the air. That teasing of bringing the brush down on his bum but barely touching. Yes that was far too fun.

Had me wondering who else I should be spanking over my knees.

That was till I got to the next naughty phone sex boy that was found playing in my make up. Using my blush brush to apply blush to various areas of his body beyond the cheeks on his face. Really his balls didnt need that extra rosy color to them for I was more than happy to smack his balls around with a paddle.

This strict phone sex mommy is all for a little CBT when it comes to keeping her boy in line. I know your probably thinking that punishment is a bit too much but not really for these naughty boy really did deserve his balls being spanked. Sure he tried to tell me he was sorry and that wouldn’t happen again but we all know that once they discover that feel of that blush brush on their nuts they will want to fondle those balls again and again.

I could spend my time telling you how I punished other naughty boys but I rather explain over the phone how I am gonna punish you, for something tells me you are in need of a strict phone sex mommy and well I am right here.

Just ask for Nancy.

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Sissy Boy Phone Sex Panty Assignment with Courtney

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sissy boy phone sex panty

Hey this is Courtney and a day wandering around downtown had me thinking about a sissy boy phone sex call. Oh don’t be all surprised that I would be thinking about a call from the night before. We all have those moments where something happens the night before or weeks before and we keep replaying them. Don’t ask me why I couldn’t shake this sissy session.

It wasn’t like he had a sexy voice that had me going oh fuck yes. Not with “Carlie”! This 50 year old guy loves to dress up in all sorts of pretty girlie things. His favorite thing or well so it would see for its what he always wears when he calls me, is a pink baby doll.

Could tell you all the things we do on that call in his pink baby doll but really your wondering why I couldn’t shake the call with dear old Carlie. Well decided to vamp it up a bit for him. Rather than letting the fun end after our 30 minutes of flirting around with him dressed up and putting make up on to make out with his dildo Bobi. Carlie really needed to go out with some feminine clothes on. So told him to go out and buy a pair of thing panties and wear them under his khakis.

Ya simple assignment. Right?

Well that is when Carlie started to fluster and sputtered for words. He was going but I have to go golfing with my buddies and and and. Yup excused don’t want to hear them. Want you to go shopping and wear those all day long.

Carlie knew as much as I did that those thong panties would be riding high on his hip and with him golfing he would be bending over lots and well someone was bound to see the top of his pretty panties.

So waiting on my next sissy boy phone sex call with Carlie to see how he did with my little panty assignment.

Have you ever gone around all day in a pair of panties? How about giving me a call and telling me how exciting it was or who knows maybe it was a day of humiliation thinking everyone knew you were wearing them.

Courtney

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Be Dru’s Pretty Phone Sex Sissy Boy

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pretty phone sex sissy boy

Let me make you a pretty boy. Well not just a pretty boy but a pretty phone sex sissy boy.

Yes that’s right I want to have you sit down and let me put on that make up to make you one passable little sissy bitch. From picking the perfect shade of lipstick all the way down to what dress to put you in.

Why not let a phone sex tranny dress you up and make you the best little pretty sissy boy on the block. Ohhh now which part is getting you excited? The fact that you will be dressed up by a ladyboy or the fact I will have you out on the street looking all pretty. Cause honey when you look that good it would be a shame to keep you inside. Have to go out and show off my work of art.

While doing your make up we can chat about all sorts of things like where you want to go while your dressed up like a pretty phone sex sissy boy. Or better yet what trouble you will get into as a pretty sissy boy. Yes you and I both know that lipstick was picked cause it was the perfect shade of “I wanna suck dick!”

You can reach me by calling the number below.

My name is Dru the hot sexy shemale ready to transform you into one pretty sissy boy.

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Sissy Boys Dressing Up in Public with Kassidy

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So a question for the sissy boys are you liking the cooler weather? The fact you have to bundle up under layers of clothing to keep warm does that give you some extra freedom to put on those pretty frilly garments under those winter coats etc?

One of those things I always wondered.

I mean in the summer I can see you being nervous to wear panties for fear of someone seeing up your shorts or noticing those panty lines through the thin material of your slacks. But in the winter you have a little more freedom dont you?

There is that extra security of knowing the pants you wear are thicker. That panty line wont be seen as easily. You can wear a bra cause you know it will be hidden away under your sweater. OR maybe your a touch more daring and opt to wear a blouse under that sweater cause hey the office is kept colder this time of year.

So sissy boy you take more freedom with wearing something girlie out in public?

This kinky phone sex girl is eager to know!

Give me a call and tell me your little secrets about dressing up in women’s clothes during the cooler winter months. Or are you a closet sissy boy that keeps all your pretty girlie clothes for your personal time at home?

Just ask for Kassidy and share your sissy boys dress up confessions

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Phone Sex Babe Courtney Dolls up Sissy Boys

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So I admit that I am a pretty basic phone sex babe. You can find this girl next door type laying around the house in a tank and a pair of panties. Hair up in a messy pony tail. Opting for the fresh face no make up look.

Now before you sissy boys all jump on me going OMG girl how can you even call yourself a girl when you wear no make up??? I do wear it just think there is a time and place which happens not to be while laying around the house. When I toss on my make up I want to be going out and someone seeing all my efforts.

Course I know many of you guys don’t have that option when it comes to make up. For getting dressed up is a rather taboo thing. You come home draw the curtains and dig out your girlie clothes from the back of the closet. Then begin the amazing transformation from man about the city to closeted sissy boy.

I admire the effort you put in to your looks. Most the time I am rather envious of the make up you guys do. Other times I am thinking you need a big bottle of make up remover and some SOS pads to take off that thing your calling a face. Sorry but good lord! Moderation ain’t a bad thing.

Thinking tonight being Friday night we should share a few make up tips. What make up you love. Are you a matte lipstick girl or shimmer? Which girls do you watch on youtube for helpful make up tips.

You know a real girlie girl gossip session. Talk about fashion. Makeup and well fucking. Share some blow job tips maybe. Its one of those anything goes sort of Friday nights with this phone sex babe. The sky is the limit!

Just ask for Courtney when you call.

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Corseted Phone Sex Sissy Boy Training with Jennifer

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corseted phone sex sissy boy training

When a sissy boy goes snooping through my closet you will find a wide variety of fetish wear. Oh don’t share you head like you have never snooped in sexy woman’s closet. Chances are you fingers have done some wondering through a panty drawer a time or two and even pocketed something you shouldn’t of. Well I welcome you to my closet for this is where you will learn the proper way to dress as a sissy phone sex boy.

No Walmart specials in my closet only the finest of fetish attire.

Leather, Latex, PVC and more.

I would love to share my fondness for such wonderful fetish gear but the one thing that I do love dressing a sissy boy up in is corsets for its how I get my wonderful wasp like proportions. It is how you as a sissy boy will lose that masculine figure and gain a more hourglass figure. This does require training your waist. You dont suddenly develop a sexy figure over night. Far from it. I shall expect the most obedient of sissy boys serious about their corseted phone sex sissy boy training.

The training starts with finding the perfect corset for you.

To become my corseted sissy boy ask for Jennifer

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French Maid Sissy Boy Fantasy with Trisha

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french maid sissy boy

I have come up with a most splendid of ideas. Well if your a sissy boy I am sure you would want to be a part of it. I know most phone sex girls have you wanting to be some whore standing on the street pimping out your ass. Which don’t get me wrong I do believe there are a few sissy sluts that do deserve to be out on a street corner peddling their ass.

However, I know there are some phone sex sissies out there that are not looking to suck cock but they do enjoy dressing and being used for their Mistress personal pleasure. So that is where my wonderful idea comes in. Opening a cleaning services where I only hire sissy maids. You will be dropped off at the persons house dressed up in your french maid uniform, fish net stockings and of course those amazing stiletto heels. Ok so I will let you wear a nice long trench coat over top of your uniform but once you step through their doorway you best be dropping that coat in the appropriate location. Then its getting down to cleaning like a good sissy maid.

I know I would love to use that cleaning service. Having a french maid sissy boy wandering around obeying my every order. Does get my mind thinking that the possibilities are limitless since you are here to please me.

When you reach the dispatcher tell her you wish to speak with Trisha

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Arianna Enjoys Laughing at a Sissy Boy

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Fetish Phone Babe Arianna Here! Nothing ever quite prepares you for a man dressed up in woman’s clothing. Sure I do sissy phone sex calls and talk with other phone sex girls about feminization calls they had. But until you are honestly face to well webcam with a sissy boy.

You just have no idea what your reaction is going to be.

Well my reaction is different each and every time I get a phone sex sissy boy on cam for me. The last one though I have to say had me bursting out laughing. I couldn’t control it. Not that I ever control my laughter when it comes to sissy boy on cam.

This one oh lord! Was hilarious the cam connects and boom I see a pair of pink bikini panties attempting to cover one hairy ass in desperate need of some waxing. That ass was wiggling and jiggling to a tune that I am sure is in every sissy boys ipod and if its not it has to be. Poker Face. Good gawd he just kept going and going. As he twirled his long blonde wig was getting in his face and of course sticking to his super sticky pink lips.

Oh it was just the most funniest thing going.

There was nothing that sissy boy could do to salvage his web cam performance for his phone sex teasing goddess.

Though I am curious what will happen when I get the next sissy boy on cam.

Arianna

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Cock Sucking Phone Sex Hypnosis with Savannah

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cock sucking phone sex hypnosis

Hello Hypno Lovers! There is a certain someone who calls me looking to be hypnotized. Our hypnosis phone sex calls started out with him wanting to be my female mannequin. Where it was all about manipulating his mind in such away that when he did certain things he would end up frozen like a mannequin. No I wont go into the full details of what those certain things were. Come on now you know some things have to stay between me and my sexy mannequin.

However, I will tell you that over the time our sissy phone sex hypno sessions have twisted and taken us into some interesting new areas. Like the one we did just the other night where it was all about unlocking his thirst for cum. Not just to sit there and wonder about it or even fantasize about it but to actually have that deep yearning to go out and find cock.

Ever given a thought to being a cock sucking sissy? Sure you have maybe its time to do a cock sucking hypnosis session to only make those thoughts more intense.

Ask for Savannah

Please remember 30 minutes or more is required for a sensual hypnosis phone sex fantasy.

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