Sissy Phone Sex: Public Outing Fantasies

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My tranny ass was in the shoe store today. Of course, this shoe store is not the typical one you see in the mall.

Oh No! I don’t go to those places for my shoes, darling.

I hit the one the drag queens and strippers go to. There is nothing but walls of platform hooker pumps and mile-high stilettos. A phone sex shemales wet dream and those who love cross-dressing.

Sitting having my feet tended to by Kevin. First, I was thinking that Kevin was someone who had a foot fetish. I mean he does work in a shoe store Isn’t that someone with a shoe fetish wet dream? He would take his time picking those shoes up and admiring them. Smelling them at times.

Sure I had taken the time to wiggle my long toes but that didn’t get an adequate response. Usually, a man with a foot fetish or the like would be dreaming of sucking my toes. That is when it dawned on me. He isn’t a foot guy at all he is a cross-dresser or a secret sissy boy. He was drooling over the fact that I walked in this store dressed up sexy as can be.

Kevin was envious of the freedom I have living as a full-time shemale. I can wander in and out of stores getting my hair done, make up and nails done as well. Oh, Kevin you poor boy. Time to live a little.

I know several men out there have to live in the shadows and are too nervous to venture out in public all dressed up sexy. Which is why you call someone like myself for sissy phone sex fantasies. Most of those fantasies involve going out to public places.

As a sissy phone sex boy, where would you like to go if you had the freedom?

Whisper

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Sissy Phone Sex Fantasies with Vintage Girl Maxine

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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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Feminization Phone Sex Hypnosis with Savannah

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When most think of feminization phone sex hypnosis they think of a full body transformation. I mean is that what a sissy boy craves? To be completely passable in their own mind through the help of an erotic phone sex hypnosis trance?

Well yes and no.

For if there is anything I have learned in the wonderful world of sissy phone sex its that not everyone has the same vision. Which makes for a very interesting call. Nothing is ever the same and I love that.

See one of the transformation hypnosis calls I did was a guy who very much wanted to feel like a woman but not a traditional woman that you would see walking the street. He wanted to hit a different spectrum. He wanted to become a transsexual. To explore what it would be like have his body have beautiful tits, full lips, curves and yet still keep use of his cock.

I know interesting right?

This one something I had done to a similar degree in the past where the guy wanted to enjoy through erotic hypnosis having big breasts to fondle with while he masturbated so I did have a leap off point into a transsexual transformation phone sex hypnosis fantasy. Yes I do realize one is not the same as the other but like I say one does sort of lends itself to the other in an odd way.

My tranny wanna be had his ideal vision already set out in his mind. The type of girl he wanted to be. The size breasts. How she dressed. How she walked. What turned her on. Etc. I mean really he had done tons of prep work on his ideal vision. Which is always nice for someone to have put some thought into things. After all this is your fantasy and why not know what you want.

Must say we started out softly with some body transformations allowing him to enjoy running his hands over his soft and curvy tranny body which had him exploding in moments after being set free of his phone sex hypnosis trance.

As most experience with erotic hypnosis this was soon not to be enough and he began looking for more ways to dive deeper down the transsexual rabbit hole so to speak. Each and every call there is more mind fucking and transformations.

Do you wish to explore some feminization phone sex hypnosis? Anything truly goes. Can cover any and all sissy fantasies. Just call and ask for Savannah.

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Sissy Phone Sex Confessions

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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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Tranny Cock Worship Phone Sex with Whisper

If there’s one thing everybody knows, it’s that little sissy sluts belong on their knees. As to what they do while they’re down there…well, that depends on who they’re serving.

tranny cock worship

If it’s me they’re submitting to, there is only one reason and one reason alone I have them kneeling, and that’s to worship my tranny cock. What else is a man trying desperately to look like a woman good for? Tranny cock worship is the only thing I need them for.

So if you’re a little sissy, when you call me, you’ll be down on your knees before you know it. And even if you don’t know how to worship a tranny cock yet, you’ll know by the time I’m finished with you. I can be a very patient teacher when I need to be. Especially when the rewards will be great for me when it’s all over.

So go ahead. Put on your favorite whorish outfit. Paint your face up to look like a drag queen. Get your blonde bimbo wig and your hooker heels. Pretty yourself up as much as you can (and fail miserably at it). Then call me for cock worship phone sex. My cock is ready for some attention, and it’s past time for you to learn how to be useful to me. The sooner you call me, the sooner we can begin your lessons, and the sooner we can do that, the sooner you’ll finally be worth something other than scorn.

Just ask for Whisper the sexy shemale whose cock your about to worship.

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Feminization Phone Sex with Mrs Porscha

There are simply some days in which one gets bored. In these days of modern technology, you can see everything and do everything in such a short time, that one may occasionally end up yearning for a simpler time.

feminization phone sex

A time like the one back when we believed we discovered the music of the future because we now had synthesizers and keytars. Back when I used to go to clubs with my girlfriends and get free drinks from guys with blazers that had giant shoulder pads and popped collars over hyper color t-shirts. Of course, these days, all of my girlfriends are a bit too respectable. Naturally, that is where you little sissy boys come in!

Oh, yes, you little boys will become my little glam rock groupies as we recapture a bit of the days when Journey was still the biggest band in the world and singing “Don’t Stop Believing” at the top of one’s lungs wasn’t yet considered a cliche.

Oh, but don’t get me wrong, though. You won’t look like Dee Snyder or any other member of Twisted Sister. No, no. This particular phone-sex MILF will not be caught dead with girls like that at her side. I want you to look more like…hmmm… Madonna in her heyday, or perhaps a cross between Cyndi Lauper or Pat Benetar. Oh, tight leather skirt with your hair in a sideways ponytail…gaudy lipstick with a zebra print blouse, and a pink scarf. Tattered leggings with ankle boots, and pointless rubber bracelets.

Of course, the difference between then and now is that the white stuff on your nose will be from when the guy I select for you to pleasure that night pulls out of your mouth and misses the rest of your face…

Does that sort of feminization phone sex sound appealing to you? If so, please give Mrs. Porscha a call.

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Tranny Phone Sex Bitch Whisper

The new year is almost upon us and this tranny phone sex bitch thinks you need to end this year doing something completely different. Shake things up a bit. Time to suck some cock!

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Yes thats right Ms Whisper just told you to shake out 2023 by dropping to your knees and filling your belly with some jizz. Oh yes I am well aware your most likely at some family gathering and that just cant happen. Surely you can find 10 minutes of freedom from the prying ears. To talk about those freaky things within like you wanting to eat some strangers cum.

Hey your secret desire to be a cock sucking phone sex bitch is our little secret. Course I may just make you want to be the cum dumpster to a whole line up of men with thick cum filled dicks. Oops did I let that secret out?

Its all in fun and fantasy so why not become a massive cum craved, cock sucking phone sex whore.  Go big or go home. Since your nearly home you might as well be the best cock sucking bitch ever. I will happily train you on the ways to wrap your lips around some thick, throbbing man meat.

Just talking about cock has got me excited. Surely you are too.

We could start out with you sucking on my tranny dick. Hey I dont mind being the guinea pig while you learn the proper technique. Being the best does require practice. So open that mouth and start sucking.

Well actually scratch that let your mouth tell the dispatcher you wish to talk to Whisper then we can work on your lip placement.

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Become Cheyenne’s Cock Hungry Sissy Slut

Its Saturday morning which means if your a true little sissy slut your just dragging your ass home with the collection of cocks clinging to your breath. Or if your like the last person who called me merely waking up with the smears of lipstick on your cheek from playing dress up cause he is a closet sissy faggot.

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Yes seems not everyone is as free as myself to wander around in their full sexy bitch outfits. Granted I have been secure in my femininity for a number of years. You probably are still clinging to your masculine life of marriage, kids and well adult responsibilities. What ever the excuse is you can shed them with this no limit phone sex tranny.

Thats right!

Complete indulgence is what I offer when you call me for the ultimate in cock sucking fantasies. Give into your inner sissy slut that one you break out every so often when your other half is away for the weekend. Or perhaps who you let play when your out travelling.

I know its so hard to actually go out and suck a dick when your dressed up pretty which is why this no limit phone sex tranny allows you the freedom to be your cock sucking sissy slut self from the joy of your own bedroom.

Let me be the one to slam your face down on my throbbing hard shaft and treat you like a dirty nasty cum craving whore. Oh and if you need me to be gentle cause its your first time.. I can be but you best give me a heads up for some times I get a touch over excited when I know your all dressed up slutty for me.

So lets work on your sissy slut name and have some fun this morning. Remember I am a no limit phone sex tranny!

Just ask for Cheyenne

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Cross Dressing Fantasies with Courtney

Rather ticked off was suppose to go pick up my boyfriend but with the weather being so up and down they opted to stay working till the rains came next week. So that means I am here enjoying some naughty phone sex calls with you guys. Any one up for some sissy or cross dressing fantasies?

cross dressing fantasies

Also spend the day sorting out my closet. I am clearing out most the stuff in there and taking some of it to the consignment store. Every so often think its great to just clear out your closet so I can make room for new stuff. I can be a bit of a clothing whore. Think all girls and well sissies too.

When I was scoping out this new consignment store I swear a sissy had dropped off a stash of his play things there. For there were some straight up whore stuff. Tons of dresses for going out to the club or well sucking dick in. Then boots like omg I had no idea they would take boots that look like a stripper wore them. Hmmm maybe this is where the strippers and hookers drop off their stuff? Perhaps sissies need to go there and get their pretties on!

Like I said it was a new store that I was just checking out and I am use to carting off bags of clothes to my old store near my parent place but this place was so much fun. I know that I do taboo fantasies and nothing really surprises me on the phone but WOW walking into a place like that and seeing dirty things like that in my face. Ya you would be going holy shit someone ACTUALLY wore this! Not just talked about it or looked at it on a website but actually bought it and worked it. Did get me wondering how many loads of cum some of those dresses saw.

Ok so that is a completely random thought but like you wouldnt wonder yourself.

So I am around for some sissy phone sex and cross dressing fantasies. Give me a call who knows maybe we can talk about some of the cock raising outfits I saw at that consignment store.

Just ask for Courtney

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Sissy Bimbo Phone Sex with Dru

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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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