Sissy Boy Phone Sex with Courtney

Hey Sissy boy! Have you ever complimented a girl on her dress or shoes? Bet you have! You seem like the type who would go around noticing how a girl is dressed. Sure that girl is all pleased as punch some random guy paid her a compliment on how she looked. Except I bet if she knew who was paying her that compliment she wouldnt be so happy.

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The man paying such close attention to that jersey knit dress was someone who just finished dressing up for a sissy boy phone sex call. Oh dont act all surprise. I know your type far too well. I talk to you on the phone.

Your secret stash of clothes tucked away in a box in the back of the closet so no one will find them. The lingerie you buy around the holidays saying its for your “girlfriend” but really you havent had one in fucking years cause well.

Why dont you have a girlfriend?

Afraid she will discover your secret fetish for dressing up in women’s clothing? Well dont worry I wont laugh. Much! A soft giggle as I tell you what a sissy bitch you are for dressing up so pretty. Then I may make you venture off to compliment random girls to see if they can figure out who you really are. A sissy boy!

Ya sure sounds cruel but in the world of femination domination I am merely a sensual domme which means you havent met mean. Now your curious right? Curious what a sissy boy phone sex call with me would be like?

Well why wonder when you can simply call and find out for yourself. Just ask for Courtney!

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Become Phone Sex Domina Shiva Girlie Elf

Its rather true I am not one for the holiday season. I mean the day doesnt revolve around my glorious self so why should I really be all gun ho. Yes the presents are nice but as a phone sex Domina you should be showering myself with gifts every week.

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So how does this ultimate phone Domina opt to celebrate the day. Well I was thinking with a little feminization phone sex scenario with a jolly holly add on. See I was thinking for those sissy boys its time for you to dress up like a girlie little elf and help Santa relieve some stress before he has to dive down those chimneys.

Yes since we are talking about sissy boys I will ensure to take great time on transforming you into the perfect girl elf. From the rosy cheeks and freckles to the stripped knee high socks with black mary jane shoes.

But I dont have any good girl elves at my North Pole. Oh no this phone sex Domina has nothing but naughty elves who perhaps were ex strippers and they are more than happy to perform on those candy cane poles in the middle of the shop to ensure there is a happy and well horny work environment.

Once you have performed in your peppermint green string bikini for all those elves its off for you to show Santa how amazing your mouth skills are from sucking on all those candy canes. Yes Santa has noticed you were extra naughty this year with putting all your focus on teasing the other elves. Now its time to show him you can suck the cum from his big fat ball sack.

No need to be shy for Santa has seen it all this year. Yes even that time behind the barn. Naughty sissy elf.

Tell the dispatcher you wish to speak with Domina Shiva.

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Panty Boy Humiliation with Porsha

I caught my husband looking at porn last night. I mean, I work in the adult entertainment industry, and have even taken some risque photographs myself, but it is the principle of the thing.

So what did I do? I engaged in a little panty boy humiliation, obviously.

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See, he is one of those big, burly, manly men with the bushy beard that makes him seem like a huge fan of Grizzly Adams. So I stripped his ass down, made him put on a pair of pink panties, and took some pics of him in them. Of course, I told him that his mother and friends would LOVE to see them, and he freaked out. I won’t be letting them get out, of course, as long as we are married, but he does not know that. He’s still wearing the panties now, in fact, as I am typing this out.

I am trying to think of some things to do to him. I know some of you have wonderful ideas when it comes to humiliation phone sex, so I am leaving it open to you guys. We will call it a little contest, I suppose. The best panty boy humiliation session on the phone gets picked, and I will do it to him. Maybe I will even tell you guys what happened with it later. This should be so much fun!

The new little panty boy has no idea what is about to hit him, and he will do literally anything I say as long as those pictures exist. The funny part is that I constantly look at porn myself. Sounds hypocritical of me, doesn’t it? But who cares? I have been looking to do this to him for a while now. Wonder if I can get a dress on him… and a dildo in him, too?

Naughty panty boys just ask for Porscha

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Cross Dressing Phone Sex with Raine

Yesterday I was walking the down town area. Just window shopping and enjoying the sun before the anticipated storms the weatherman was calling for. As I was staring in the window of some kitchen shop the reflection of a passerby caught my eye.

This amazonian type woman with rather masculine features. Gotta say at first I thought it was the reflections distorting the image like a fun house mirror. Making things seem opposite to what they were. When I turned around I half expected some petite woman standing behind me.

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Nope the reflection was rather correct for it was a very tall man dressed up in ladies clothes out doing their afternoon shopping. The cross dresser just gave me the once over and proceeded down the sidewalk letting her black 4 inch heels click confidently on the brick.

Now I have to say most my interactions with men dressed up in ladies clothing has been via cross dressing phone sex calls. Well thats being full blow from the make up to the shoes dressed up. I have engaged with men who wear some item of ladies clothing like a panty boy or something who enjoys stockings. Garments that they could hide away under their “traditional” clothes so no one would find out their secret.

Which is all well and good. Rather interesting really. Nothing like playing footsie with a guy and discovering his foot is encased with silky stockings. Not sure who had a more befuddled look on their face to be honest.

Anyways I am totally back tracking with that rather limited interaction it got me wondering if cross dressing phone sex was where men who enjoy ladies clothing get their start towards public interaction?

Sort of that test the waters out with how girls on the phone interact with them and then poof venture out into the real world. Love to hear what your opinion is on that. Inquiring minds need to know.

Maybe I am over thinking the process. Either way I think this weekend should be all about some cross dressing phone sex be it humiliation or just what you should wear for a holiday party.

Raine is the name and the number is down below 😉

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Crossdresser Phone Sex with Courtney

Its the day before Halloween and wouldnt you know it last night I get some guy calling me up who is prancing around in his “Halloween costume”. Well actually that is what he is telling his friends but really he loves dressing up in womens clothing so when Halloween comes around its the one day he can actually dress up in some pretty womens costume and everyone will comment how pretty he looks rather than give him those weird looks cause he is a crossdresser phone sex freak.

crossdresser phone sex

He has a few costumes to choose from one was the school girl, which had me laughing at. There is a plaid skirt, white button up shirt, white knee high socks, mary jane shoes and if that wasnt enough he got a wig that he could put into some pig tails. I want him to wear that one. The other one was more a stripper attire, which ya that would turn some head too. Short black pleather skirt, fish net stockings, red skin tight tank top and fish net style arm gloves, knee high boots and he was going to wear his red fuck me wig.

Either way he was going to be heading down to the MAC store and having them do his make up for the Halloween party. I so want to see some pictures of how he turns out. Think either costume will look hot as hell and get people to turn their heads. He is 6’2 after all without any heels.

Have a great night Mr CrossDresser hope everyone loves your “costume”

Just ask for Courtney if you too have a crossdresser phone sex fantasy or wanna discuss your Halloween costumes past/present or future.

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Forced Feminization Hypnosis

Had an interesting feminization phone sex call but it was intertwined with quite a few other fetishes. The guy was looking for some age regression hypnosis where he is taken down to an age where he is living at home and then his mom forces him into women’s clothing.

I was definitely game.

feminization hypnosis

So after weaving my erotic hypnotic trance on him and regressing him to a point where he was living at home again. It was all about focusing the fantasy on him exploring that empty house and ending up in his moms closet and noticing a very pretty pink dress. He was oddly fascinated by it but couldnt quite figure out why. His fingers touching it and enjoying the satiny feel of the material and how soft it was against his fingers.

It was as he was lost in his senses that he never did notice his mom standing behind him at the door way to the walk in closet. The smile on her face as she saw her boy so engrossed in that pretty pink dress. How he nearly jumped 5ft when her fingers touched his shoulder and pulled him out of his trance.

Sure he tried to explain his way out of the closet but his mom would have none of it. She just looked at him and smiled as she directed him to the bed. Sit down sweetie. At first she was loving but the more he fought to be released the more forceful she became. Pushing him on to her king size bed. Telling him that he was to strip while she wandered into the closet to grab that pink satin dress.

Upon returning her boy is near naked only wearing his boxers and looking at her like he wont wear that dress. But really he has no choice. That dress will adorn his body.

The more he argues the more mom just smiles and laughs. For she welcomes having to force him into a dress. With that she is tossing the pink dress on over his head and starts getting him to twirl around and around while she laughs at him.

Mom did always want a girl and a sissy boy is just as good as any when you get down to it. His discomfort only makes the moment even more exciting. For really mom is just deciding what else she can force her sissy boy into.

Book an erotic hypnosis phone sex with Savannah.

Remember to book a minimum of 30 minutes for your hypno call.

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Strapon Phone Sex Fantasy with Savannah

All dressed up and ready for a strapon phone sex fantasy?

Well my name is Savannah and I have my plastic cock right here beside me just waiting for that perfect sissy boy ass to violate. I know you went to all that wonderful effort to get ready and here I am just like a guy only wanting to put my dick in you.

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Dont worry I do appreciate all the time it took you to get ready for me.

The extra attention you put into your makeup.

How you flipped through your outfits so you could find the right one that didnt scream anal slut. Even thought I know you been wanting a dick in your ass all day long been fantasizing about getting fucked for days. How your ass been puckering the whole time you sat there getting ready.

Oh and those panties you picked just perfect. I will make sure to rub my hands over them extra slow. So you can savor this ass pounding.

I will have to refrain myself there is just something about fucking a sissy with a long, thick strapon that gets me so excited that I can hardly hold back. Usually I have a need to just push my thick dick right deep into that waiting ass. We are talking balls deep.

But since you went to all that effort of looking so pretty for me, I think we will just have to make this fucking last a bit longer.

Are you ready for a strapon phone sex fucking with me?

I know I am.

Just ask for Savannah

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Cuckold Phone Sex Sissy Boyfriend with Kassidy

Its really no surprise that I enjoy cuckolding men be it my real life boyfriends or those special boyfriends over the phone. See I pretty much view you all the same. You soon gonna be my cuckold phone sex boyfriend.

For I will be able to do what ever and who ever I want. Now you might be going ya thats happened before Kassidy. What you dont know is that I wont do it behind your back there is no “cheating” in the classic sense of the word. I will bring over my bulls to fuck me right in front of you. Why hid the fact that your not able to satisfy me in the orgasm department.

cuckold phone sex

I am beyond faking in the bedroom. I want you to not only know but see that you are not capable of keeping me pleased. To actually see how strong of a sexual appetite I reallly have.

Now course with you often watching that makes things a bit complicated. For I know your gonna be sitting in the corner jerking off your tiny cock and well that wont do. For the way I see it as my cuckolded boyfriend you will have to endure some humiliation. So why not make you my cuckold phone sex sissy.

Yes you read that right!

Cuckold Sissy Boy.

See before my date shows up to fuck me we will both be getting all pretty. Each of us wearing some sexy little outfit. Mine of course will be to turn him on and well yours just to show us how pathetic you are.

You see where this is going?

It starts with you in panties and could very well end up with your wrapping your lips around something other than my dildo. Ooops am I letting a few secrets out?

Well how about you give your sexy girlfriend a call and let your cuckold training begin.

Just ask for Kassidy. Dare you to tell the dispatcher you wish to be my cuckold phone sex sissy boyfriend.

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Feminization Phone Sex with Arianna

Now I will be the first to admit when everything switched over to online ordering and well curbside pick up I was a bit miffed as a feminization phone sex creator. For there is nothing quite like getting a sissy boy calling from the parking lot to do a quick 10 minute session to motivate him to walk into a lingerie store or well any retail store to purchase women’s clothing.

That rush of taking the scared wanna be sissy and giving him the huge burst of confidence he needs to go into that store and buy his first outfit in person. Its a game changer. Course when the world flipped upside down that little sissy game got taken away and it was back to online shopping. Which yes is fun but there is that rush you get motivating someone to actually step into a store.

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The phone sex call afterwards of hearing them panting and near breathless of OMG OMG OMG I did it!

Telling me so fast what they bought and what happened. Course its a quick run down of events that even the sissy boy sitting in his car is able to process the entire events of the shopping experience. Which I get I mean its an adrenaline rush.

So back to the online shopping thing. It ends up being a different rush. You looking at when that order will arrive course some are working from home like your favorite feminization phone sex creator and get to understand the joy this freedom brings. Such as wearing wonderful girlie outfits but also tracking your new purchases. Which means you can dress up sexy and if your lucky or unlucky depending on the sissy you can run into your delivery driver. Or maybe they get a sneak peek at you through those curtains that werent as closed as you thought.

Or maybe its just the matter of leaving the make up on from the youtube tutorial you were enjoying earlier in the day when you go to sign for that package while wearing your boring man clothes. Honestly the humiliation factor is rather limitless and well your at home so it does make thing more interesting. Cause I know lots of you were going shopping 3 towns over. Now those clothing items are showing up at your home. In boxes that say Victoria Secret.

Ya feminization phone sex just got far more interesting with ship to home purchases.

Who is up for a little online shopping?

Your Phonesex Tease ~ Arianna

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Sissy Slut Phonesex with Jillian

The weekend is upon us and I know you have been struggling all week in your man clothes. Maybe you slipped a sexy pair of panties underneath those slacks just to make those work clothes feel less confining.

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Funny how you can be all dolled up in bras, panties, stocking, garters, skirts, blouses, heels, wigs and make up etc and that feels less constricting than your business suit. Oh how your gonna rush home come that Friday 5pm tick of the work clock. All day you been planning your outfit. The sexy heels you ordered last week finally came in. You been stretching them out so you can wear them all weekend long.

Gonna do your sissy slut phonesex strut in your whore outfit. Now the question becomes will you actually suck a cock this weekend? Or will you just call me up and continue the dick licking fantasy?

I know its just so hard when you crave to be more than a pretty dressed up bimbo. You want to be a cum whore. Desire to be a jizz junkie but just cant quite get there. What a shame. Time to end the madness I say. Give me a call for some hot sissy slut phonesex fun and let me guide you into being an actual cock sucking whore.

Be rather fun.

My sexy voice pushing you into that next step.

I mean you want to impress me dont you?

Just ask for Jillian when you call.

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