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Sissy Boy Phone Sex with Raine

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I was at my girlfriend’s house on the weekend. Suppose to be picking out courses for the coming fall semester. Alright so it was mostly watching movies and chatting about who was dating who now. Never ending drama in the friends circle. We paused the movie we were only half watching so I could head off for a washroom break. The washroom was right next to my friend’s brothers bedroom and his door was partially open.

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As I walked by I could hear Taylor Swift playing softly which I thought was super odd since he was a hard core metal fan. Never heard anything but that since I known him. So of course I had to look in thinking he might of snuck a girl in there. Yes even a kinky phone sex coed can be a bit of a pervert too. Not gonna lie was a touch horny and would of loved watching him get a blow job from some hottie.

I wasnt really ready for what I did see. It was my girlfriend’s brother dressed up in his mom’s lingerie.

Ya! It was a bit of a shocker to say the least.

He was dancing around in black panties and bra and some silk robe. I tried really hard not to giggle but really how can you not laugh at seeing a sissy boy dance around in what can only be his mother’s undergarments.

Sure I have seen pictures of sissy boys who call me for some kinky phone sex fun all dolled up in their favorite frilly outfits.  But to see it in person from someone you have known for a really long time. Gotta say I was a bit stunned.

Well not stunned for too long cause as soon as my brain comprehend what I was seeing I had to run off to the bathroom and laugh. Didnt wanna get caught peeking in on the sissy boy.

Bet your wondering if I told my girlfriend about what her brother was up too?

That little info you will just have to call me for.

Dial the number below and ask for Raine!

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Cuckold Phone Sex Sissy Boyfriend with Kassidy

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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.

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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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Cock Sucking Instructions From Shemale Dru

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We all know you love a little JOI when it comes to rubbing that clitty but I am gonna give you a different time of jerk off instructions today. Well actually its just some helpful instructions over all its how to suck a cock 101. Since your have already found your way into dressing up pretty the cock sucking will be the next adventure for you.

I know you will want to be the best at that. Hate to be the disappointment to that gentleman who so graciously gave you his cock to suck. Right?

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That is where I come in for you gonna grab the best and biggest dildo from your collection. Now dont look at me all innocent and doe eye like you are stunned I said dildo collection. Sissy sluts always have a collection of cock in some drawer. Never know when your gonna wanna see how a new lipstick will look on a dick. So I am sure you have various sizes and colors of dildos in that drawer.

Grab your favorite cause I am gonna give you a detail description on how to work that cock like a nasty cock sucking phone sex slut. Yup when you drop to your knees to work a man’s dick over that guy will be doing his best to try and not to blow his massive load down your throat.

Course with these amazing cock sucking phone sex instruction you will have all the wonderful ability to take control of his orgasm. Working that jizz right to the edge leaving him breathless and begging for more of your sweet sissy cum dumpster of a mouth.

So while you work on figuring out which cock goes best with the lipstick you have on currently I will be sitting here by the phone. Patiently waiting to instruct you into being the perfect cock sucking phone sex whore.

Just ask for Dru.

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Sissy Bitch Becomes Whisper’s Cock Sucking Trainee

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You know your wife is out fucking another man. Sure you should be deeply upset by this little discovery but yet your not. Instead you are searching the internet on ways to be a pretty little bitch boy so that your wife may invite you to the party. She has told you a thousand which ways she isnt into having two men but perhaps you can convince her into having that real man and you the new sissy bitch.

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Welcome to being a cuckold to your wife’s latest sex fantasy. Its the one she was hiding away from you but trust me as someone who is use to transforming men into pretty girls I have you covered from helping you choose the perfect panty to tuck your useless nuts into all the way to what lipstick will leave a nice ring around a cock.

Oh ya I did say cock! For your gonna be the sexy fluffer that ensures any guy fucking your wife will be rock hard by the time they hit that pussy. So best work on your cock sucking skills. Hell as a sexy shemale I will be more than happy to help you work on your oral abilities. But how about first we start with your pretty little outfit.

I know that is what you sissy phone sex bitches are eager to start with anyways. Must always be pretty for those impending erections. Just ask for Whisper when the dispatcher answers your call.

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Sissy Boy Shopping

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When I was younger I use to work in a lingerie shop and one time a sissy boy came into the store. Always enjoyed when a sissy ventured into the shop, it wasnt an every day occurrence but every so often a guy would get up the nerve to come in. I could tell he was nervous. Probably his first time coming into a store to buy something sexy specifically for himself.

Think most sissy’s always buy on line but really where is the fun in that you can’t go out and touch the clothes and feel how soft it is and what it will feel like against your girlie parts.

I had fun with him pointing out all the new panties and bras to that sissy boy. I know your wondering how I knew it was a sissy boy and that he wasnt buying for his “girlfriend”. Well he just had a certain aura about him well that and he was trying to feminize his movement along with the slight hint of lip gloss and the eyeliner he didnt quite remove from his play session the night before.

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I was giggling and laughing with every item I made him buy. it was lots of fun. Pretty sure his sissy boy clitty was getting excited with all he was buying.

With doing phone sex calls especially feminization type fantasies it makes me long for the days of working in the lingerie store and interacting with nervous sissy boys. Which is probably why I give you sissy phone sex boys so many go out and buy lingerie from an actual store assignments. Love hearing that rush in your voice when you call me after that assignment is done.

You can reach me at the number below to set up your own sissy boy shopping phone sex fantasy. Never know might start out as a fantasy and lead to a real assignment.

The name is Arianna

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Sissy Phone Sex Daddy with Josie

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Who knew there were so many sickos out there ok well sickos might be a strong term but like come on when a guy is all let me be your daddy but like dress me up to be your mommy isnt that a bit like umm odd? Like I get sissy boys and Daddy fantasies but come on you try and keep a straight face through sissy phone sex daddy fantasies.

You just fucking cant!

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Well maybe you can but like if your calling me to be your daughter to dress you up then just know this sissy phone sex daddy your gonna be dished out some humiliation cause like there is no way in hell that I can be all this is my sissy daddy with a straight face while I introduce you to my friends who come over for a sleep over.

Like I know your gonna be right in there as a sissy bitch wanting to be playing make up and wanting a full on slutty make over. Ohh wait maybe you didnt want a slutty make over but like thats what you get with me and my friends cause how can we not make my sissy daddy into a full blow cock craving whore.

Yes I know your not that type of sissy but come on its just tooo much fun making your lips pop out with that peppermint lip gloss. Making it all tingly and feel those lips pop like you were sucking a vacuum cleaner.

Do you all wanna get dressed up in my clothes? Cause like we are definitely gonna have to talk about more of an allowance for clothes since your gonna be stretching out all of my panties and those body hugging dress are well not so cute on me. They pretty much hang on me and dont show off any of my cute body. Ya gonna need a clothing shopping spree ASAP!

Thinking my sissy phone sex daddy would love a two bratty princess on the phone with him cause like who doesnt love more than one girl giggling at him and dressing him up. So tell the dispatcher you would love to have 2 sexy barely legal princess’ dress you up tonight.

Just ask for Josie and the dispatcher will take care of the rest.

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Bare Back Phone Sex with Sexy Tranny Dru

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This year for Christmas I want to bury my tranny cock balls deep into some sissy bitches ass. But thats not even the best part I want to do it all condom free. Yes today is all about some bare back phone sex fantasies that will have you begging for more of my bare cock!

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Since its the holidays I am in a rather giving spirit.. Giving of my load of hot jizz up that sissy pussy of yours. Though I know your a true little slut and have opted to don your crotchless panties at the Holiday Party. Yes I know you couldnt handle the idea of covering up that cum catcher of yours but at the same time a girlie girl does love the feeling of pretty lingerie rubbing against her over grown clitty.

Dont worry I love the fact that you put on that bright red crotchless panties it makes fucking you so much easier. Course you probably thought that pack of condoms you stashed in your clutch would be used. Or better yet I would opt to drain my nut juice down your throat. No I am not feeling like unloading in your slutty mouth. I rather fuck you till I orgasm right up that tight ass tonight. Enough of the teasing.

See I know your sissy pussy is virginal. Ok perhaps virginal is the wrong word. i know you have had a number of cocks up there but you have yet to have a load of cum spray upon those rectum walls. Let me be the first to Christian that anal cavity with my hot sticky load. You wont regret it.

You will be walking around with my cum dripping out of your ass all night long. To see the jizz stream glistening on your stockings in the flashing Christmas lights.

Yes its time for a bare back phone sex fantasy with  this hot phone sex tranny Dru!

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Sissy Phone Sex: Dru Makes You a Pretty Girl

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How many sissy phone sex boys are just loving this time of year? Can venture out into the stores to stock up on your lingerie and make up without a sales girl blinking an eye. Ok so maybe only a few of you sissy boys have clued in that you should be running out to get your pretty on this time of year.

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Seems this sexy shemale had to pass that little info on to a few. Sure some of you sissy phone sex boys LOVE the element of getting caught so this really doesnt pertain to you. The bold bitch that will walk into a store during prime time shopping hours. When anyone and everyone are watching you hold that hot 1950’s inspire dress up to your body in the public mirror. This by far doesnt apply to you.

I am more talking to the ones who hit up Walmart in the middle of night when only the bare minimal of crew are around. So ya can by your cheap ass panties with generic make up. Now is the time to have some fucking fun! Go out and enjoy the fact you can sit down at the Sephora make up counter and get a consultation for your new “Halloween face”. They buy all the products.

Yes that is what I am talking about.

Oh and once your all made up give me a call for some hot sissy phone sex! I mean you cant let that pretty face go to waste. Or maybe you need to call me first so we can work out your plan of shopping attack. The stores to hit and what you should say to the sales clerk.

Ya that sounds about right!

Just ask for Dru the sexy shemale ready to help you pretty up your girlie ass.

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Sissy Phone Sex Boy Confessions with Arianna

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So sissy phone sex boy how is your girlie voice?

Have you been off practicing it? Sitting in rush hour working on that feminine voice that will match your alter sissy ego. Hmm what is her name? Jessica Carmen? Jennifer? Barbie?

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Its always interesting what names you boys come up with for your pretty girlie side. I have to admit over the years of doing sissy boy phone sex calls I have wondered about the process that goes in before your call. Like do you dabble in the lingerie and consider yourself a guy with a fetish for women’s lingerie? Or do you honestly know your a sissy bitch the moment those silky nylons slip over your feet?

Does your name come to you while your applying your lipstick? That first pucker of your lips as your kissing the air make you think oooo I feel like a Kylie. Or does your name come from someone you knew at school. The slut of the high school that girl you admired for sucking so many dick. Your girlie side surely desires to be just like her.

See so many questions for you sissy boys. I know we could focus on the clothes and the make up and all things pretty and girlie but really wouldnt it be fun to focus on the how’s an why’s?

How did you come to that dressing style? Why that name? Where did you learn your make up techniques?

Ok so some of them are not quite how’s and why’s but you know what I mean. Dont you long for a gossip session where you just let all your secrets out. Why you became a sissy boy is the question I would like to know.

So when your in the mood to divulge those inner most secrets give me a call. I know I cant wait to hear them. Then after the sexy question period I could fuck you with my strapon. A good sissy phone sex boy does deserve a treat.

Talk to you soon, Arianna.

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Cock Sucking Phone Sex with Shemale Whisper

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The joys of summer where you can spot a cock sucking fag from a mile away. Yes your eager to know how a sexy transsexual like myself can spot you wanna be cum eaters.

Well very simple.

In this hot weather you guys are going for something cool Popsicle and freezies. The real men will just dive into those frozen treats biting them with out any due care.

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A closeted cock sucking phone sex fag will slowly unwrap that rather phallic treat and lick it with soft delight. Savoring that long thick icy pole. Closing your eyes to enjoy all that is in your mouth. Wrapping your lips around and sliding that slippery frozen novelty in and out.

Your getting the picture right?

Basically your desire to give a blow job is so strong your giving your summer time refreshment one. Sick fucks. Whats even sicker is your generally unaware of your own sexual perversion. Happily standing there with your friends deep throating an icy treat while they are talking about the baseball highlights from last night.

Do you care? No!

All your focused on is how amazing it would be to fall to your knees and suck a thick cum filled dick off. Your eyes half opened wondering which one of your friends would let you do such a thing on July 4th. Could you get one of them drunk enough?

Well as your shaking your head trying to erase that thought from your mind. How about you jump to a very safe alternative one that wont have you outing yourself to your whole neighborhood. Give this sexy tranny a call. See we can talk about your cock sucking desires over the phone and keep you in check.

Now before you say Whisper should you be promoting my inner bisexual cravings? But of course. However, I also know there is a time for discretion and perhaps this is it. Lets talk about your need for another mans dick in your mouth during a cock sucking phone sex fantasy. Then take it from there. We can get to the outing yourself at a later date. Perhaps after BBQ season.

Just ask for Whisper when you call!

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