Category: Sissy Training Phone Sex

Did you know about National Tell a Lie Day?

sissy training phone sexDid you know that April 4th was National Tell a Lie Day? Well it sure was, so I decided to have a little fun at my sissy’s expense. I told sissy that we were going to do something special, something that she never in a million years thought she would ever be able to do… Can you guess what that was?? Haha I told sissy that I was so horny that I would let that little bitch fuck me! OMG you should have seen her face! She was overjoyed and I swear she was so excited that she almost passed out! She 100% believed that I was going to actually allow her to fuck me with that tiny little shriveled up wannabe cock! It was ridiculous really and I could only keep a straight face for maybe five minutes before I just busted out laughing in her face. I laughed and laughed, I laughed so hard that I damn near pissed my panties and that was when sissy finally started to get a clue that I was lying. I told sissy what day it was, that it was tell a lie day and that just made the little bitch cry harder. Ridiculous really that she was so upset, I mean seriously, this little bitch has a two inch little clitty why would I ever actually want to fuck that?? I told her that she needed to suck it the fuck up and quit all her bitching because this was just part of her sissy training phone sex sessions and if she wanted to continue her sessions with me that she would need to quit her bitching and get ready for all the huge cocks that were coming over to fuck her. She shut right up after I said that, my sissy is a huge dick lover so she didn’t want to miss out on all that!

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April first is coming soon…

sissy phone sex April first is coming up soon and you know what that means right? April Fools Day! Man I hope that this year turns out as funny and memorable as last year! You see, last year I decided to fuck with my favorite sissy and boy did I get her good! I called her up and told her that I was feeling very generous and extremely horny and that it was her lucky day because I was going to let her actually fuck me with her tiny pathetic cock. Oh wow was she ever excited! She rushed on over here with her tiny little clitty just poking out the front of her panties, she was just so happy that her luck had finally changed… until she actually got here. Once she walked in the door she knew she’d been had because we all jumped out from our hiding places and yelled April Fools! I laughed at her sad lil face and asked her did she really think a Goddess like myself would ever let a tiny dickie like that touch me?? She mumbled no and even had a couple tears roll down her face but once the first big black cock went in her mouth she was back to being a happy sissy again. I wonder who I should prank this year…

Forced feminization phone sex is what you’ll get!

forced feminzation phone sexOh you silly, silly boy did you really think that your pathetic little penis would be enough to satisfy me? Really it isn’t even big enough to be called a penis, that tiny thing is barely 2 inches long so in my book that makes it a clit. You are the perfect little bitch boy I’ve been looking for actually, I’ve been wanting someone like you to makeover into my newest sissy slut. Oh, you’re not a sissy you say? You don’t want to dress up in frilly little panties and a slutty little dress or have your hair and makeup done? Awwhhh well isn’t that just too fucking bad for you! Have you ever heard of a little thing called forced feminization phone sex? That’s where I take your little bitch ass and FORCE you to do whatever the fuck I want… and right now what I want is to dress you up and whore your faggotty ass out to the highest bidder! You are useless as a man, that pathetic little wannabe cock is never going to satisfy anyone but you so you may as well rent that ass out. Don’t worry, you might choke on those huge cocks at first and I am quite sure that you won’t be sitting on your sore bottom for at least a week after your first time but it will get easier for you… eventually. I know this is hard for you to take, I’m sure when you came over here that you were thinking you were going to get to fuck me and things just didn’t go your way, now did they? Oh well sissy, you will get used to all of it… one cock at a time.

Spring Break Tranny Fling

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I had no plans to get laid when I walked in for coffee. I was hung over from last night and half asleep. I was on Spring Break and decided not to go to Mexico.  He was in the corner and wouldn’t stop staring. Finally, he came over and handed me a business card. “Damn, you’re sexy. Let’s have dinner.”  I smiled and nodded.

He took me out 3 times and didn’t make a move. I just knew tonight was gonna be the night. I shaved my balls and legs, put on my new panties, and some make-up. There was no way he could resist. And I was right. After the movie ended, he drove me out by the cliffs and kissed me. I felt my cock spring to attention. He squeezed my tits and placed my hand on his cock. It was thick and juicy and I couldn’t wait to taste him. He fucked my mouth until I could take it no more. I turned away from him and pulled down my panties. “Fuck me from behind.” I whispered. He moaned as he shoved his dick unto my boy-pussy. “God, you’re tight.” he groaned. He gripped my hips and began to slam me hard, gaping my asshole wide open. His throbbing fuckstick blasted off, filling my anal cunt with cum.

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“It’s my turn now” I grinned, pulling my swollen penis from my panties. He looked at me with fear and surprise as he realized what he had done. “Yes, you fucked a tranny. Now you get to suck my cock. ” He jumped on it like a hungry mutt. Such a good little closet faggot. He milked every drop from my balls.

It must be Spring Fever cause we fucked and sucked all night. My tranny cock “sprang” to attention every time he touched it. I couldn’t get enough of him. I’m sure we’ll be seeing each other again.

Naughty sissy is getting outed!

sissy phone sex“Hi Everyone, my name is Sissy. And I am a total loser! Want to know why I am such a pathetic sissy?” Well, you see… I must have been a very bad sissy. Sissy is in trouble with Mistress Levi. That must be why she is forced to pay the consequences. Literally. Mistress Levi wants our site sissy’s name in the blog, and I couldn’t be happier to out her. She is the one that is always saying “Please tease me! Giggle at me! Laugh at me! Out me, humiliate me & punish me as I deserve!” Yes Sissy, just as you deserve. You know you want it, you crave the attention of being outed, oh yes you do. We ALL know it. We all fucking love it. Talking about a loser sissy like you and all the silly things you do for a reaction from us beautiful, worship-worthy women. Sissy, don’t you know I have no problem telling the world about you? I don’t need an excuse to tell everyone that Michael is a transvestite mincing and prancing in public for total humiliation and sissy shame!!! Oh, that she is… just a pathetic fake man who loves this shit, eats this shit up because all Sissy wants is someone to talk about her. Someone to out her and tell the world that Michael  is a pathetic pansy crossdresser who is punished with public humiliation for all to see!!! There! There it is sissy, everyone knows what a loser you are…and next time they’ll know about your love for panty pudding too.

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Silly sissy you’re no man!

sissy phone sex redSilly Sissy you are no man, you are just a fake little loser that has come to me for your comforting and humiliation. I deal with ‘men’ like you all the time. Even in my daily life, with your fancy cars or big trucks, always trying to take away on what a pathetic piece of shit you are. But you know you can be your loser self with me, you know I’ll treat you just like you wanted. I even picked out an outfit for you already – collar included. So everyone can know you’re my bitch! Clip that collar on and I’ll attach the leash, walking around main street like you’re my special pup. Everyone is laughing your whole pathetic ass being exposed with a big huge sign screaming fuck me I’m a sissy fag! And who could pass that up? Looks like these big cocks are about to dominate you, my pet. I’ll sit back and watch you taking cock in your ass and smile, knowing you’re loving every second of it.

Ass-fucked by China Doll

prostate phone sexYou came into my massage parlor asking for something different. One look at your cock and I understood. It was teeny, barely 3 inches long. I stifled a giggle but you heard me anyway. You told me that you couldn’t be satisfied the normal way with your dick in a pussy. You needed something more. Something thick and juicy to fulfill the craving. Pulling a 10 inch strap-on out of a bag, you begged for some prostate stimulation. Only then, by milking your ass gland, could you get off and have a good orgasm.
It felt weird, that huge cock on a tiny Asian girl. I stroked it a few times as I lubed it up. looking in the mirror, I got a little turned on. You were already bent over the table, begging for it. Suddenly, my personality changed. I began to humiliate you, making fun of your little dick.
Pounding my dick deep into your faggot ass, I hit your prostate, making you moan so loud. “Come on you no-cock, slut.” I yelled. “Take my cock.” I reamed you with no mercy as you begged me to stop. My own pussy was throbbing now and I didn’t want to stop. I wanted to hurt you, make you feel my fuckstick deep in your bowels.
Finally, I pulled it out and made you lick my big dick clean while you jerked your nub onto your belly. A splatter of cock snot and I knew I had done my job well. You’ll be back, sissy boy.

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You will do exactly as I say!

sissy training phone sexHahahahaha, you of all people want to be a sissy? A sissy bitch? You think you’re pretty enough, you think that you’re gay enough for for the job? I am so not sorry to tell you that you are not the sissy for the job. You see if you want to be a sissy you have to be a very pretty girl I’m talking a full on make over and if you won’t allow me to do that than you’re just not worth my time. Well technically you’re not worth my time anyway but I do enjoy spending my time humiliating a pathetic sissy loser … And a loser like you is going to need a lot of work a lot of waxing new girlfriend and of course we’re going to have to get your ass ready. Do you know how we’re going to do that? Lots and lots of ass fucking not only from me and my massive strap ons but my fucking huge big black cock friends. Every sissy whore loves big black cock and it’s no different for you, loser. Don’t try and tell me differently. You’re taking cock up your ass like it or not, bitch.

Suzi Meets Her Match With Princess Paris

Tranny Phone SexI have a new address from the escort service. I am supposed to be a dominant tranny on this evening to a submissive male. I dress the part in my black shiny latex dress and fuck me boots. I pull into the drive of a very nice house and ring the bell. A beautiful woman comes to the door. I ask for Mr Rick, which is who I am supposed to see on this evening. She tells me there is no one there by that name. I’m a little lost as to what to do since my cell has no service in this area. She invites me inside to use her phone, which I graciously accept. Once inside, her attitude completely changed. She called me her tranny slut for the night and told me she would train me on being a “real” woman. Calling my agency for the correct address was long forgotten as I seemed to fall into a trance in front of this beauty. and found myself wanting to do exactly as she instructed. She had me change into a little pink dress that was sickeningly cute and lacy panties. The panties did not contain all of my package but I tucked it in as best I could. She redone my makeup – exchanging my usual dark black eye shadow and bright red lipstick for  softer more feminine shades. She even put my hair into pig tails. I felt utterly ridiculous, but also turned on. I bounced around her house as she instructed, ultimately showing  just  how silly I could be, until her friend showed up. Her friend was a very muscular, hunky guy and I was immediately attracted to him. She began to tell him to do things to me such as piss on me and humiliate me in any way he good. He told me I was a sissy shemale bitch and that he was going to use me as his personal toilet. He advised me to open my mouth. I did and received a large stream of piss directly into my mouth which I gulped down without hesitation.  Before the night was over, I had taken his huge cock straight down my throat as well as in my tight tranny ass. He had rewarded me with a huge load of cum in both. Princess Paris and her friend showed me who was boss on that night – and for once it wasn’t me. I never did make it to Mr Rick’s house.

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All of us humiliate our site mascot!

sissy phone sexI’ve been training Anastasia to be the perfect Mistress, just like me. She is learning well with lots of practice humiliating our loser sissy! Some of my favorite things to make this loser sissy do is sing to me, over and over again. She just fucking adores to be forced into humiliation. I should say that the site sissy loser doesn’t have to be forced to do anything at all because she wants to do, begs to do it just begs for the humiliation that we give her. That’s not all the dirty little secrets I have about sissy! I have some VERY dirty (literally) secrets and I know that as soon as sissy lays her eyes on this blog she’ll be making that poopy panty pudding all over again. Oops! I let the secret out…as if everyone didn’t already know that our site sissy loser liked to poop in her panties. That’s even more embarrassing than the size of your itty bitty winky. What else can I do but laugh at a pathetic failure like yourself. A failure at being a man but definitely are winning at being a stupid pathetic sissy. The kind of sissy that has no control, that begs for this over and over and doesn’t care if she gets caught or exposed because what you really want is to entertain and be the silly fairy faggot you are and as I help teach Anastasia how to be a superior mistress like myself we will continue to use you for practice in our humiliation towards you, got that you poopsie panty pudding sissy? That might as well be your new name – I might even write a song and make you sing it. Who knows – I can make you do anything! We all know that…don’t we? Go ahead and go clean up sissy, we all know you have plenty of panty pudding to take care of.

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