Sissy Boy Phone Sex

Street Walking Phone Sex Slut with Whisper

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street walker phone sex slut

It should come as no surprise that one of my sissy phone sex slut has graduated from parading his ass up and down his hallway to shaking those hips on hooker avenue. It often happens. For really, it is only a matter of time, you go from admiring women’s clothing online to ordering your own outfits for a little dress up once a month to needing to satisfy that inner slut feeling on a more regular basis.

Course for this naughty sissy phone sex slut it seemed once he was able to walk in those hooker shoes, he was craving to go out there and shake his ass in front of the men and see if he could actually pass as a real street walking whore rather than just role play being a lady of the evening standing on the corner.

Oh and before you wonder, yes he did have to gradually work himself err I mean  herself up to wearing them ankle breaking heels, for one does not just leap into wearing those fuck me pumps. Sissy phone sex slut started with a 2-inch and once was able to parade up her hallway without the assistance of using the wall to steady her wobbly ankles, could move up another inch. Then and only then could she move to wandering a pathway outside the house.

Yes, she did have nerves wandering around in public in her sexy heels but oh the excitement of shaking that ass outside of her hallway. Course I think half those nerves was her hoping and praying she would get some cat calls. Mind you there was probably a part of her hoping for a rather indecent offer such as an invitation to have a dick in her mouth. You know that is gonna happen at some point for the wanna be street walker.

Just ask for Whisper

 

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Sissy Boy Phone Sex Panty Assignment with Courtney

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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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Glory Hole Phone Sex with Arianna

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glory hole phone sex

Sensual Phone Tease Arianna Here! It’s that time of year when everyone is making wish lists of what they want. I don’t care who you are making a list. I think as we get older, the list gets a bit more kinky and nasty. I feel like a bit of a kinky elf hearing some of the guys’ confessions lately. For really, there are quite a few of you guys that are calling to tell me their taboo phone sex fantasies about what they would like to do for Christmas or even better on New Year’s.

Like Mike, he has usually kept his kink to porn watching and taboo phone sex calls. Which usually does it for him. He loves watching porn and talking to an anything goes phone girl like me. So the other day we were talking and he goes. Arianna I really want to suck a cock before the year is over.

I tried not to laugh cause he just blurted it out. I mean we weren’t even watching glory hole porn. It was some foot worship stuff. And come to think about it the nasty phone fuck has never even done a glory hole phone sex call with me let alone a wild bisexual fantasy.

So I was just like, huh?

Where did that come from?

Guess he has been watching some glory hole porn and well seeing all those cum sluts on the monitor has got him craving to be a jizz guzzling glory hole phone sex whore himself.

All I have to say is Go Mike!

Like I would stop that wish.

Just ask for Fetish Babe Arianna and lets explore your glory hole phone sex fantasies today!

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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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Sissy Deserves Arianna’s Strap On

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Hello, my sweet sissy. I know that giving in to your true nature has been hard. Any major life change can be. Though I also know that you feel more complete now than you ever have. Knowing your true place, and where you fit in this world, this life, is very freeing indeed.

Now, given that, the only places where you feel empty still are the places that don’t have a cock in them. You are made for pleasure, and you also take some guilty pleasure in being filled up. By men, especially.

Well, I don’t happen to be a man or have a cock, but I do have the next best thing, little sissy slut. I have a strap on with your name on it. It may not be a “real” dick, but you will moan for me just the same. If you are a good sissy, I will even be nice and lube you up first!

Knowing you, your ass just involuntarily twitched in joy as your little clitty began straining against those pretty panties. You’re wondering what I’ll have you do first? Maybe lick the length of it up and down before taking it between your greedy lips? Maybe pretend to jerk me off while I pet your head and giggle? Or maybe we can completely skip the foreplay for once, and just get down to making you scream my name as I ram it deep inside you. Or maybe you have some other scenario we can discuss? Strap on phone sex is full of fantastic possibilities, really.

I love hearing your dirty little fantasies of having me buried deep within you, your painted lips wide in a cry of pleasure. Just call me to make it happen.

Just ask for Arianna for a true sensual domme experience.

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Pegging Phone Sex with Gail

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pegging phone sex granny

There is nothing more exciting than to dress a men up in a bra and a pair of panties. Why you may ask? Well I plan to fuck his ass with my strap on and well I think its far more enticing if he looks sexy for his pegging phone sex session with myself, Granny Gail.

It also helps him get in the mood as well.

There is just something about slipping on a pair of panties and adjusting yourself so you fit them just right. The sensual sensation of the panties rubbing against you. The erotic mind set as you know those panties will soon be pushed aside and your ass taken advantaged of with my strapped on dildo.

You know once those panties are rubbing against your swollen cock, you will be begging me to bend you over and fuck that ass.

Perhaps its the idea of being pegged by my strap on that gets you feeling rather submissive or perhaps its knowing your about to have your ass claimed by a sexy pegging phone sex loving GILF. What ever gets you feeling like a total anal whore this sexy granny wants to hear all about it.

Don’t be shy either. Come tell Granny Gail how you want to dress sexy for me and have me peg that ass of yours.

You can reach me by calling the number below and just asking for Gail. If you wanna be extra naughty tell the dispatcher you wish to book a pegging phone sex session with Granny Gail.

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Sissy Whore Hypnosis with Savannah

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sissy whore hypnosis

So what item of woman’s clothing does a sissy whore need to put on to make her feel extremely feminine?

Is it stockings? Heels? Or maybe some make up?

Now what would you save it I made your favorite sexy feminine item a hypnotic trigger. Where you put on that item and that feeling of becoming a sissy phone sex slut takes over you. Whether you just crave the idea of having more womanly mannerisms or maybe its becoming full fledge cock sucking slut.

For my last phone sex caller it was to have his sexy lipstick to be the hypnotic trigger that put him not only in a super feminine state of mind but craving to be a cum craving sissy whore. Every time s/he applies that lipstick s/he would know that mouth is missing something very important… a cock sliding over that lip paint.

Each application of her/his red lipstick had him gliding into a deep hypnotic trance where his mind goes blank. Well near blank I mean this is a cock craving sissy whore so there is only one thought sliding across this sissy’s mind.

Cum.

Leaving her red lipstick mark around a hard cock as she works on draining every drop of cum from it. In the attempt to satisfy her cum craving.

What would you like your feminine trigger be?

Give it some thought and then come book an erotic hypnosis session with me. Let the transformation into being a nasty cum slut begin. Oh and if you desire to be nothing more than just a pretty slut wanna be we can work with that too. After all its our time together and where the fantasy goes is up to you.

All boundaries are respected.

Call the number below and remember to book a minimum of 30 minutes for a sissy hypno phone session.

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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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