Sissy Boy Phone Sex Archives - Extreme Phone Sex Fetish

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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Burlesque Feminization Fantasy with Savannah

January 5, 2024January 5, 2024 by femdom

Hello Sissy Boys. Every so often I find I think about an old caller. There can be something that flashes on TV or something someone says or whatever; then boom I am reminded of that one call. That is exactly what happened when I was looking at some burlesque stuff. I use to have a caller who would never quite call himself a sissy but definitely had a feminization phone fantasy. Where he was a beautiful burlesque dancer and the erotic phone sex fantasy was all about getting him ready for the stage.

Granted this guy loved the art of being dressed up for the stage with fancy gowns and beautiful lingerie but it was just me dressing him up in a sensual roleplay we never did explore this fantasy through erotic hypnosis. I know you are probably rather surprised that the Hypno Goddess never did explore a burlesque dancer fantasy under trance but we never did.

However, it has always been in the back of my mind what fun it would be to do this feminization fantasy while the person was in a deep state of trance.

To go under so deep that you can feel those makeup brushes brushing against your skin. You hear the music of the girl who is currently on the stage in the background. To feel the satin and lace of the corset pulling you in and giving your body that curvy figure. To feel the silkiness of the stockings wrapped around your legs.

You can see where I am going with this right?

Erotic hypnosis will just enhance everything about this fantasy all the little things really that will make you crave to be a sissy slut for hypnosis. I of course am more than happy to guide you into that deep state of sensual trance that will have you feeling the beat of the music and have you dancing away to your audience.

Granted you may not see yourself as a burlesque dancer which is fine but I would love to help you explore your feminization fantasy while you under my erotic trance.

What sensual fantasy do you see yourself exploring?

If it’s your first time exploring or thinking about using erotic hypnosis to explore your fetish fantasy then be aware that 30 minute minimum is in place when doing sensual trance. Hypnosis is a specialty fetish and does require more time to get you into that wonderful deep state of trance… This can not be rushed nor should it!

Ask for Savannah

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Sissy Boy Confessions with Jillian

December 20, 2023 by femdom

With everyone talking about holidays does that leave you pondering if you have been a good sissy boy?

No really are you sitting there wondering if you have sucked enough cocks to qualify to make the nice list or would all those glory holes you visited this year put you on the naughty list?

Does get you wondering but dont worry I know which list you should be on. The one that didnt suck enough cock. The one that has you not dressing up enough through the year.

Yes I know you told me you were busy with work and family but really I gave you a few easy to do sissy boy assignments and you still gave me excuses. So that has your name slipping down and down on the nice list.

Santa only wants to visit the sissy boys who he know will absolutely drop down on their knees and suck dick for him.

Will that be you?

You did say no when you were off on that out of town work trip saying you didnt know where to go. What places would be safe. Etc. Etc. All excuses a true cock sucker would of said bring on the dick. I want cock. I need cock in my mouth. Taking full advantage of being in a place where no one knows them.

But not you. No you sat in your hotel room jerking off to cock sucking porn. Naughty boy.

Granted you did call me to confess all your cock sucking fantasies too but really it would of been more fun if I was listening to you actually suck a real dick. Hearing that man tell you what a nasty bitch you were for him.

Well looks like we found your 2024 goal. To take a real cock in that mouth.

Till then you can reach me at the number below. Just ask for Jillian

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Sissy Bimbo Phone Sex with Dru

June 15, 2023 by femdom

You’re already a sissy. You threw out all your male clothing long ago. You’ve accepted that your tiny little clit belongs in a chastity cage for now and forever. You’ve grown your hair out and now keep it styled in a feminine way. You have more makeup than most department store counters.

But that’s not enough for you, is it? You want to go further.

Well, that’s just fine because as much as I like sissy boys and sissy girls, I like sissy bimbos even better.

It’s time for you to weed through your closet again. But this time, you won’t be throwing out your long-forgotten male clothes. You’ll be tossing out everything you own that’s not sissy bimbo material. You must look like the slut you are at all times, so no pants, no skirts longer than just an inch or two below your ass, no shoes with heels lower than four inches, etc.

And, yes, I know you already know how to do your own hair and makeup, but you’re going to have to learn a different way. You’ll be going full platinum-blonde, and you’ll be growing it out even longer than it already is. You’ll also be learning to slut up your makeup even more so than you already do.

Oh, and get ready for pink. Lots and lots of pink.

If you’re ready to begin your sissy bimbo phone sex training, then call me. Just remember that bimbos only speak when spoken to, so don’t let the thought cross your pretty little head that you will be allowed to say whatever you want to me.

Just ask for Dru

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Sissy Salon Fantasy with Porscha

May 15, 2023 by femdom

I was going through my wedding album the other day. Looking at my gorgeous wedding dress and veil. I loved everything around that day the hours of getting ready. Sitting in the salon getting the up do and my make up. The list really goes on and on. Perhaps its holding on to that special moment which makes it so much fun when I have a sissy who wants to do a salon fantasy.

Mind you this time I would really like to so a sissy salon phone sex fantasy where that sissy is getting ready for a wedding. Sitting in that chair with the hairdressing cape over them. The long blond wig being twisted on to big hot rollers. Have to build up that volume. Know the butterflies are fluttering around in your stomach over what your end result will be.

How will your hair turned out? Will it be like you planned?

As the last roller is being placed that is when the make up artist comes in to work her magic over your face. Opening her box of delightful colors that has your eyes just dancing in delight.

To feel the coolness of the foundation being applied. The casual conversation about what your wedding dress is like and what is going on with the reception. Things your all to excited to answer.

Far too excited about your dress.

So what do you think ready for a sissy salon fantasy and let me be your hairdresser and perhaps more.

Porscha

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Lingerie Loving Phone Sex Sissy

April 25, 2023 by femdom

So I know I do phone sex probably way too much when I start getting ideas for sissy boy assignments in the most craziest of places. Well maybe not that crazy considering the assignment I thought of. I saw this guy wandering the mall while I was working, folding panties of all things. He completely made me think of this one phone sex sissy boy that loves lingerie which is probably why we ended up talking. But anyways. I was watching this guy walk around the mall and I swear he had a thong on under his clothes like he was dying to pick out the ass floss but at the same time enjoying it a bit too much.

So I was like wouldnt it be fun to give the lingerie guy an assignment where he had to wear lingerie to the mall. Like panties, bra, stockings, garter belt, sexy cami under his jacket. Ya I didnt let him wear a shirt but was allowed pants. Then sent him to the mall and made him walk by the lingerie shops and think of me.

I havent heard back from him yet. So not sure if he did it or not. Or maybe he is still wandering the mall?

Have you ever done any crazy sissy phone sex assignments that got you really excited? Or maybe you want to do that one and send me pictures of you dressed up.

Oh and lingerie loving phone sex sissy you so need to call.

Kelly

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Sissy Adult Baby Phone Sex

April 15, 2023 by femdom

I adore sissy babies. Love putting them in those frilly dresses with the pretty ribbons and tons of lace. Those tights with the frills on the bottoms and the socks with the lace around the edges. I can go on and on with the joy dressed a sissy adult baby brings me.

Probably the only thing that exceeds that joy is publicly humiliating a sissy baby. For you dont expect me to be content will just having you prance around the house in that pretty girlie outfit do you? No of course not. I want to show off my little bundle of pink goodness to others. Now I know they are not all going to be as accepting as I am and they will be giggling and laughing at you. That is what its all about making your cheeks redden with embarrassment.

For those that love to be embarrassed when they are all dressed up in those pink diapers. Nothing quite like a 2 girl phone sex call where I get to tell the other girl how you are all dressed up and listen to her laugh and laugh at you.

I did just that with one particular taboo phone sex babe on the site, Emma she has the cutest giggle and she loves humiliating sissy adult babies as much as I do.

I know Emma and I would love to team up and dress up another sissy adult baby role play again.

Give us a call for a 2 girl phone call just ask for Nancy and Emma.

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Small Penis Humiliation Phone Sex

March 10, 2023 by femdom

I want to thank the small dick men out there that wear panties. You are making it so easy for a girl like me to figure out who is under endowed in the penis department. Sure I just though guys wearing panties were secret little sissy boys but come to think back to all the small penis humiliation phone sex call and how many of you little dick guys who like to wear panties. I know realize those panty lines your sporting are actually excellent way to weed you out.

Now dont get all worried your never going to get near a hot girl. Thats not the case cause even a hot girl wants a good laugh and well lets face it what you are tucking under those pretty little panties gives us a very good laugh. Course the great thing about small penis humiliation the more we laugh at your itty bitty thing the smaller it shrinks.

Good news for you guys I love to laugh and well I have a great laugh.

Now all I ask is that you wear some pretty panties for me. I dont care if they are used but between you and i we know picking a pair of panties out of the hamper is the only way your small dick is ever going to get near a pussy.

I have to say though if you fit comfortably in a thong pair of panties then expect my laughter to be hard on those small penis humiliation phone sex calls. Yes if your asking I will watch you on your cam. Why I am agreeing to this is beyond me but I do happen to enjoy the pathetic show your small dick men in panties put on.

Get ready for some small penis humiliation when you call

Courtney

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