Category: Sissy Training Phone Sex

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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I’m ready for Valentine’s Day!

sissy phone sexI am so fucking ready for Valentine’s Day! I am sure you know why…my pets are all going to spoil me fucking rotten. I am expecting dozens of roses, lots and lots of chocolates and stuffed teddy bears. Lingerie and high heel shoes. I want too many pairs of panties to count. I want sex toys and gift certificates to get my hair, nails and even a massage done. I am going to be lathered in presents this V-day by all my pets. My sissy pets are so loyal, I must say I do adore an obedient sissy that treats her queen as I should be treated. Those are the ones that get my attention. The ones I take shopping with me and dress up. The ones that get a full sissy makeover and even gets to see my special friends is the kinda of sissy that will be spoiling me this Valentine’s Day. My sissy pets will get the utmost reward for spoiling me, they’ll get their own v-day… one that includes them wearing the lingerie and having their ass fucked.

Sissy Phone Sex Training with Aunt Sheila

sissy training phone sex ffSissy training phone sex is much more fun than I thought it would be for me. I don’t get many sissy calls, but that is about to change because I have my own sissy under my roof. My nephew is staying with us for several months. He is this smart boy who graduated early from high school but can’t start college in the Fall. I thought I was making him a man when I took his virginity, but apparently, I have made him a sissy. I caught him wearing my underwear to his job. When I searched his room, I discovered a slew of missing undergarments of mine. Bras, panties, pantyhose, even some slutty club wear and makeup. This boy was clearly not a man, but a sissy. I confronted him when he came home. He tried to lie to me. To me, the woman who is giving him a roof over his head. I grabbed him, pulled down his pants and gave him an old fashioned bare bottom spanking. Of course I had to remove my pink panties first that he was wearing.

I was enjoying paddling his ass, but not as much as he was enjoying it. Every spank I gave him, he came on the floor. Turns out my nephew is a sissy and a punishment whore. Well, if I was going to have a sissy under my roof, he was going to dress and act the part. I made him clean up his cum off the floor with his tongue. We can add cum slut to the list of things that describe him too. After that, we went shopping for a sissy maid outfit for him to wear and some panties that fit him better. It was like having a daughter. In fact, that is how I view him now. I have changed his name from Mark to Marie. Outside of the house she can be known as Mark, but under my roof, she is Marie, a good little sissy that cooks, cleans and does whatever her Aunt wants her too, even fluff the cocks of the various boys that entertain me while my husband is at work.

spanking phone sex ffMarie and I are in the beginning of our relationship, but sissy training is going very well. I know they say boys will be boys, but some boys were never born to be boys, don’t you agree?

We’re going shopping

sissy phone sexI can’t wait till this weekend! Want to know why? My personal Sissy and I are going shopping. Not just any kind of shopping, the kind that will involve a purchase at a famous lingerie store and lots and lots of fun dressing up my sissy too! I love lingerie shopping, throw in a silly little sissy like mine and you’re going to love it even more! That is what I am so excited for…well and of course having sissy stare at me like a goddess wishing she could look  like me only for me to laugh at her and have her poser ass put on a new thong set. Sorry Sissy, you’ll never look THIS good but it’s fun to imagine, and it’s fun to put you in your place. If you step outta line too much I’ll really have to put you into place, this can and will include lots of big fat cocks that are going to be keen on dominating every hole of yours…just like a girl sissy! Just like me, isn’t that what you wanted? Oh, it’s going to be a fun shopping trip!

Stupid little sissy bitch

sissy phone sexStupid sissy bitch, don’t you know I have no time for you? No time to waste trying to please you when you should be the one pleasing me! And not in the sexual make me cum way because we all know sissy bitches like you can’t do anything like that you’re far too pathetic in that department. Even if your wife is lying and telling you your tiny cock is pleasing her, it’s not pleasing her at all. She is probably fucking some black man with a massive dick behind your back. But that’s okay you’re doing things behind her back aren’t you? Dressing up is stupid sissy faggot outfits and begging to be fucked in your stupid sissy ass. I know you even wear my underwear when you think I am not looking. But I don’t have time to deal with your dress up fetish I only have time for you to entertain me so I think it’s about time we got to that. About time I brought you over here to get your sissy ass fucked hmm? It’s time you officially became my bitch by taking this 13 inch cock in your ass and then finished in your mouth. Ready to make me laugh?

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Faggot Bitch Takes My Strap On

You are such a fucking pathetic little whore. When you come over, my best friend and I are going to defile every inch of your worthless body. You are going to be our personal little sissy bitch. We are going to send you home crying. When you come over, we are going to make me strip naked while we put a thick collar on your neck that adores the name “Sissy Bitch”. Then we are going to attach a chain link leash and guide you to the bedroom like a dog. You are going to bend over while we paddle your fucking ass. You’re going to squeal in pain like a little bitch boy while your ass gets bruised by two little girls. Once we decided you can’t take it anymore, you will get on your knees and suck our big eleven inch strap ons. You aren’t getting any lube when we fuck your ass so you better make it count, we tell you. When your jaw starts locking, we are going to take turns fucking your puckered asshole like the fucking faggot you are. Don’t you love being our faggot bitch?

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Renting Your Ass Out

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No matter how mean or cruel I am to you, you keep crawling back to me. I guess you just can’t help but be the slut you were born to be. You used to take pride in being so manly. I remember you used to have to go to the gym every day. But that’s all changed now. I own your ass. Quite literally, isn’t that right? Maybe you keep crawling back because I have a nice toy chest filled with big dildos and butt plugs…or maybe it’s the fact that I have an unlimited supply of real man with nice cocks who love to take out their frustrations on you. That’s really all you are, is just a fuck doll used after a hard day at work.

The first time you took a cock it took you hours to get ready. You wanted to look perfect for your Master for the weekend. It was the start of me renting out your ass every week. Guys paid good money for your ass to, but of course you will never see any of those profits, even if it was your ass that made them. I guess you are useful for something after all. I still remember the face you made when you saw the man hand me a big wad of cash. You looked so fucking pathetic down on your knees with the collar attached to your leash, just looking up at me, begging with your eyes like a lost puppy. Now I think you really look forward to the weekends. You never know what your weekend Master will have in store for you. Sometimes you get a nice Master who only makes you clean their ass with quick ass slapping. But this weekend you are in store for a very hard weekend. This guy even paid extra. You can’t even imagine what he is going to do to your pathetic bitch ass.

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