Category: Sissy Training Phone Sex

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I stabbed at your asshole with my stiff dick. You moaned out loud, arching up to receive me. I felt your sphincter relax and I slid inside. So fucking tight around my cock. I love ass virgins. Tonight had been our first date and you were fumbling like a nervous teen as you reached under my skirt. The look on your face was priceless. I thought you knew I was a shemale. Now, as you gripped my hard cock, you looked up at me. “I always wanted to suck a cock.” you whispered.
I smiled knowingly as I pushed your head down. I love sissy domination phone sex!! You gagged and drooled trying to inhale my big dick. Mmmm, I love me a good little closet queen. You sucked cock like a girl, whimpering as you bobbed up and down. I looked down to see you stroking your own cock. It was small and thin. Oh, the perfect candidate for training to be a bottom. I stroked your ass and smiled as you responded. l slid the tip of my finger into your tight rectum and began to finger fuck you. “Oh, please, ma’am, please fuck me. Teach me to please you.” you lisped. That was all it took. Such an easy little whore.
You screamed out loud with my first hard stroke. Taking your virginity had me so turned on. I wanted to treat you like shit and make you love it. I called you names. Fairy faggot, princess, and sissy, they just seemed to make you hornier. I was pounding you with full, hard thrusts, ripping your ass-pussy raw. “Harder, ” you moaned. That was enough to make me blast your sexy ass full of ladyboy sperm, just as your little dickie spurted onto the floor.

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Sissy cumslut humiliation phone sex with Miss China

sissy training phone sexWelcome to China Doll’s Parlor of Pleasure and Perversion where nothing is too bad. The pussy is young and tight and I am always happy to see you. How can I please you today, master? Maybe you like prostate massage or strap on play? Or maybe you wish to to become one of my girls. Now boys can be like girls. I offer training and Hot sissy cumslut humiliation phone sex for men who wish to have pussies.We bathe you, dress you up, make you pretty sissy and pimp you out to suck much cock. Pretty boys must be trained like girls. You must learn the art of giving pleasure to men. Balls must be shaved. No nasty body hair allowed. Panties only may be worn. First lesson involves being laughed at and forced to do degrading things. I have a list that you must complete to be accepted into the next session. My girls will help me with session two as you learn to suck cock properly and get fucked in the ass by me. Once asshole toughens and heals, We will set you up on dates. These dates will be clients of mine who will critique your performance. I only choose the best sissies for my elite club. You must be able to handle rough and dirty sex and beg for more.

Our final step is a shopping trip to buy you new girly clothes and sexy lingerie for your new job as a Massage Slut Sissy. Are you ready? I require strict and obedient compliance. Soon I will introduce you by your new name and you will be the girl you always wished you were.

Open that ass-pussy wide and prepare to get fucked as you see me being used below!!!

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Two is better than one

2 girl phone sexTwo girls to laugh at you? Two girls to humiliate your pathetic ass? That’s a dream come true for you, isn’t that right stupid sissy faggot? Your tiny fucking dick makes us laugh so hard, nothing like that could please us. That’s why you’re going to be forced (supposedly) to be a little sissy faggot and dress up like a pretty girl! Makeup is the start of it, earrings too. We’ll laugh as we torment you. You know if you want to be a girl you have to take cock like a girl and Anastasia and I have more than enough cock for you! Giant, fat cocks. Cocks that are going to stretch your ass so far – just like a girl does. You will take more than one cock at a time, slutty fucking sissy. You need one in your mouth and one in your ass. Now we’re really laughing at you. You’ll never be a superior woman like us, and you know you’re nothing but a fake man. We know you’re a sissy faggot and we’ll never let you live it down. No worries, we know that’s exactly how you like it anyway.

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Pathetic Lil Diaper Wearing Sissy

sissy phone sexLooksies here, it’s itty bitty baby faggot Michael fucking F. Pathetic little pansy. What can I do with you but laugh at you? You know that’s all you’re good for. That’s why you dress up in your wittle diapers with your paci – so fucking pathetic. Little diaper wearing baby needs attention, is that so? Hahahaha, what a loser! Such a lil diaper wearing fag, crying and begging for some attention from a superior woman like myself. She wants to be a big baby, I have no problem treating her that way. Babe’s gotta know nice and early how to behave, and that includes the humiliation you want. Hahaha, little sissy baby can’t resist dressing up, can’t resist being a whiny little brat in a crib. You get to be laughed at now, all my sissies can laugh at you cuz you’re even lower than them, sissy baby. You will get the most attention of all don’t you worry. Being made fun of by my sissies and me too? I bet you’re just dying to pee your diaper. But if you do you’re going to be known as a bad sissy and we don’t want that now do we? We’ll just keep laughing at you, hahaha – you pathetic little diaper sissy!

I Love You Sissy

adult phone chat sissyIt’s been so long since I blogged about our Sissy Fairy Faggot., but when I saw her pretty pictures I had to do it…

Sissy is all dressed up and looking fab for a day of shopping on the town. She feels so special in her heels with her jingly jangly bracelets and her big hoop earnings. Her dress showing off her fantastic legs and sexy sissy shape. She looks like a million bucks.

People laugh and stare while pointing at her and taking pictures. She is the center of attention every where she goes. Sissy is such an exhibitionist. She doesn’t mind the taunting and people making fun because she knows that these Sissy Days makes her Princess happy.

I dream that one day Sissy will be brave enough to walk into the office dressed in her pretty Sissy clothes and talking in her sweet Sissy voice. It would be great on Halloween so that no one had to know that in her heart this is her true self. Of course we would all know that this is our REAL Sissy and that the fake man they see every day is just an impostor.

On this special day, Sissy could lock herself in her office and call her Princess. I bet you anything that if she did this Princess would let Sissy squirty squirt tight there at her desk in her pretty dress with her coworkers just on the other side of the door!

What a momentous day that would be!sissy phone sex

It’s time to show off our site mascot again!

humiliation phone sexIt’s time to show all my cuckies and all my sissies the perfect example of a sissy fairy faggot! We have the house mascot Michael F…….shall I say her name? Hmm, I guess we’ll see. She loves to dress up for all of us, she is the ultimate panty wearing little bitch! She begs to wear soft pretty girl undies, but we all know you’re a fake man! I am going to make sure all my other sissies, and all my cuckies follow by your perfect sissy example. Dressing up to go out and show off your pretty legs and all you have is that itty bitty baby dickie of yours hiding in your sexy little panties of yours. Ha! Pathetic. I am even going to make my sissies into little poopy princesses just like you, oh yes, now everyone can know about your poopy princess dreams. Go ahead; pat that little ass of yours in your panties full of poo. So gross, but even more humiliating. Maybe the house mascot can also teach lessons on how to be a big dick sucker in her pretty blue dress and her pretty hoop earrings; I think that makes her the perfect cocksucker. And hoops that size make you an automatic whore. I don’t make the rules, but Sissy Michael Fra…… sure does put up a hard image to follow.

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Fairy faggots need sissy girl phone sex!

sissy phone sexSissy girl phone sex is what you’re looking for, aren’t I right little sissy fairy faggot? I know I am. It’s what you crave so desperately. You need someone to make fun of you, publicly shame you, humiliate you, transform you into the pretty whore you want to be. Prep your ass and mouth for some massive cocks and your body to turn you into the sissy slut you are! There’s nothing you can do, you can’t lie to me. I know you’re a naughty little girl dying to dress up in all my sexy clothes. I know your cock is itty bitty and oh so very small, and I know you crave to be turned into a girl. You need some makeup, some panties and a dress. A pretty wig and some earrings too. Look at this pretty whore, she sure looks ready to be fucked! My friends will agree, they’ve all got massive cocks, and you have no choice but to take them like you deserve, like you want and crave. There’s no small cocks for sissy whores like you!!!

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New Sissy Night

sissy phone sex zettaThe night is here. The night that two men will discover their inner sissy with my help and the help of all my friends. They have arrived and I am helping them with their costumes. They are so excited and a little apprehensive at the same time. They have been nervously shattering since they got here and their dicks have been rock hard since they walked through the door. Asking a million and one questions about what they can expect tonight and how this is going to work. I am trying to explain to them that this evening isn’t scripted. Things will flow naturally and as the night progresses and we all get more intoxicated inhibitions will begin to slip away and the courage to move forward will replace the uncertainty. The one thing I am certain of is that by the time it is all said and done they will know what it is like to have a shemale cock in their mouths, swallowing sweet jizz. They will experience being on the bottom and taking tranny cock in their tight virginal asses while they get pumped full of cum. I know they want it, they are here with stiff dicks and enthusiasm for what is to cum.

Humiliating Sissy Phone Sex

Sissy Phone Sex

You’re a bend over bitch aren’t you? I can tell just by listening to your whiny voice in my ear and the way that you’re constantly begging to touch your dick and let you fuck me. As if that’s ever going to happen! I don’t do little dicks and I sure as fuck don’t do whiny ass little bitches. You do realize that the only way you’re ever going to get any kind of action is if you bend over and take it up the ass don’t you? In fact I would really enjoy seeing you get spit roasted especially if you’re wearing a frilly pink dress and slutty fishnet stockings while you’re doing it. Don’t pretend that you don’t love it.

Start out on your knees slut and open up wide. I want to watch you go from one cock to the next licking and sucking all over their dicks and balls. I want to see you deep throat them. Unless you want to remain celibate for the rest of your life you better learn how to relax the back of your throat and take it all the way down. Let me hear you gag on it, I want to see your eyes water. Once those dicks are all lubed up from your mouth push your sissy ass up in the air and feel one dick slide deep up your asshole while the other one fucks your face. Look at those two dicks spearing you thrusting in and out making you their bitch. It’s the perfect look for you cause you definitely aren’t good enough to fuck pussy.

Nothing But a Bitch Boi for Sissy Phone Sex

Your nothing but a pathetic bitch boy for sissy phone sex play. Your weakness is my greatest indulgence and my control over you is what i thrive on. You putting your will in my hands, whether you want that or not. I’m going to take the bet that you are secretly growing hard at the thought of me controlling your bitch ass.

So, there you were at the club looking all nervous and dressed like such a suburban prude. I could just tell you really wish you weren’t such a small dicked loser, and didn’t have a chance of getting pussy. Fuck, I can really read them. I approach you and get you a nice stiff drink, and sweet talk you into relaxing a little. I loosen and remove your tie, unbutton a few buttons on your shirt, and yank it outta your pants. Your looking a little less wretched. 

I whisper in your ear how I have an apartment nearby and I think you should accompany me home. Instead of taking you to my place though, I take you to my friends house who was having a party. I take you up to his sisters room and start undressing you… 

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 Oh don’t get too excited… your not getting what you think. I want you as my personal bitch and dress you up like one. I have you all pretty and drag you downstairs. I take you into a room where a few other girls have brought in their little bitches who were already at work. I push you towards a large framed black man and tell him your ready. He pulls out a huge black cock and forces you down on your knees before him. Face fucking your bitch mouth isn’t all he’s going to force fuck. Oh… and sissy… they don’t use condoms.