Sissy Boy Phone Sex

Crossdresser Phone Sex with Courtney

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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.

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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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Kassidy’s Cum Fetish makes you a Bukkake Princess

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So I have said that I may had a bit of a cum fetish, I love hot loads of jizz being squirted over my face and tits. Any where over my body really. So of course I am a bit preoccupied with bukkake fantasies. I guess that is why I end up with sissy boys coming to me to talk about their cum fetish fantasies.

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Not so much that they want to shoot their own cum on themselves oh no! These sissy boys want to be on their knees feeling what its like to be a bukkake slut. To take multiple nut batter loads all over their made up faces.

Probably my last favorite bukkake phone sex call was making the sissy become a cheer leader. Ya you probably know where this is going. I had to take that sissy cheerleader into the boy locker room where all those foot ball guys were hanging out after the game. They were in a bad mood since they lost the game and well needed a bit of a cheer me up. What wouldnt do that other than a slutty little cheer leader.

Mind you my cheerleader had all these guys to satisfy at once and only a few holes. What to do? Ok so you know where this is going. That sissy just dropped down on her knees to say boys get ready to jerk off and me and coat me in your ejaculate. Let the jizz fly!

What guy wouldnt want to be apart of humiliating a sissy bitch like that?

Every where she turned there was a cock with cum dripping out. There heads swelling up more and more as their balls are filing about ready to burst. Not knowing when that cum would blow out.

Ya describing each cock in detail.

Only made that sissy beg for those cocks to blow hard and fast.

How many cocks do you fantasize about squirting over you?

Call Kassidy and let her transform you into a little bukkake princess.

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Sissy Adult Baby with Mommy Jennifer

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Mommy Jennifer got to have some special fun with a certain phone sex adult baby who came crawling into her nursery. That he was in desperate need of a changing. So he was put up on the change table and carefully striped down. Getting rid of those boring clothes and put into the clothes that would make him feel more comfortable. As she powered that bottom with lavender powder this adult baby knew he was in for something special.

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He watched his phone sex mommy reach for the diapers on the top shelf above the change table where all the pretty pink things where kept. He tried his best to squirm but nope it wouldnt. For Mommy was too strong and quick with that diaper change.

On that pink diaper went.

That wasnt the only pink thing that phone sex adult baby got either. For Mommy Jennifer was giggling away as she was laying out all the pretty pink sissy baby clothes she was ready to put him in.

I know your going to wonder what all happened.

What did Mommy Jennifer do to that sissy adult baby? Well your just going to have to call and find out in your own sissy phone sex call with Mommy Jennifer.

The number is below is how you can reach Mommy Jennifer

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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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Strapon Phone Sex Fantasy with Savannah

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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

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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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Feminization Phone Sex with Arianna

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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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Strap On Phone Sex FemDom Shiva

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So your dressed up like a pretty little bitch, I see. Now your mind is wandering from getting all pretty to actually feeling like a slutty bitch. Which means your on the hunt for a strong dominant woman like myself who will bend you over and fuck that sissy boy pussy.

Good news! You found the femdom of your dreams for your next strap on phone sex fantasy. Well I am the Mistress of your dreams only if you care to speak to someone who wont baby you or give too shits about you.

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For I am not about to compliment you on your shade of lipstick or how great you applied your eyeliner. I will compliment you on how tight your pussy is for me as my thick plastic dick is slipping pass that sphincter.

Your here to help amuse me.

So by all means pick out your sluttiest outfit for I do appreciate a sissy boy who puts in the effort on feminizing his so called masculine body. Just make sure I have super easy access to what I want. Your girlie pussy and that mouth. Did you think I wasnt gonna claim you from both ends?

Well I shall be for that is what a strap on phone sex whore will do.

Suck it.

Fuck it.

Then suck it again just to be a good bitch and clean off that dick!

Dont worry you can find your new femdom strap on phone sex mistress available for calls most nights. The number is below all you need to remember is to ask for Shiva.

Now off you go and get extra slutty for me.

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Sissy Boy Phone Sex Slut with Courtney

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You know when you get in that mood? Well ok so I am always in a mood cant help that but today I am in the mood to dress up a sissy boy. Ya I want to tap into those days where I use to dress up my barbie dolls. Except now of course the version of playing dress up with my doll will be a bit different. After all I can be far nastier with you than I could my barbies.

Or will it?

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My barbies were always a touch on the slutty side messing around behind Ken’s back with who ever came along in the male boyfriend department. Yes I did have more male barbie dolls and the no name versions of such dolls cause well its more fun to have my barbie girl out numbered. 

Seems I was a bit of a cuckold girl back then when I think about all the things she did behind Ken’s back. 

Anyways back to you sissy boys. I want to dress you up into the perfect cock sucking whore. Yes thats right! Making sure all the guys are gonna take note of you and think DAMN! I want to slide my fat cock in that slutty bitches mouth. Fuck that is a perfect little fuck hole!

Well you get the idea right?

Time to become my perfect sissy boy slut and gobble up some cocks. 

Just ask for Courtney!

 

 

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