Category: Sissy Training Phone Sex

Making Men My Bitches

Shemale Phone SexI dig a good fucking blow job from a wet man’s mouth. The way their lips feel as they slide down my tranny shaft. I look down at the man on his knees and I can see he is so desperate to please me. My tranny body has him in a trance and under my spell. I order him to turn around commanding him to get on all 4rs. I kick his legs wide open spreading his ass cheek with my hands. I see his tight asshole pulsating for my tranny dick. I jam two of my fingers deep in his ass twisting them before I pull my fingers out. With a wicked laugh, I shove those same two fingers of mine in his mouth down his throat. Making him taste his sweet ass juices. Bringing my dick head to that puckered tight hole of his as I slide smoothly in his ass. Making yet another man my bitch.

Babysitter’s Fuck Club

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My best friend and I started a sort of evil, slutty babysitter’s club- we call it the Babysitter’s Fuck Club. We make sure to sissy and slut train your little brats and for an extra fee, we can show you just how slutty we can be. The other day, we had got a job with the both of us booked. That usually never happens but we figured we had a lot of tikes to watch. When we get to the house, the daddy answers the door and lets us know that the brats are already in bed and that the mommy is taking a while to get ready. Odd but okay. He leads us into the kitchen and offers us some water but I had a better idea. I heard the shower turn on and started rubbing my besties pussy in front of the daddy. He instantly got turned on while I began licking her pussy and took off my shirt. I then pulled out his hard cock and started sucking his cock. My bestie got on the counter and he started licking her pink teen pussy. We both fucked him right there on the kitchen table while his wife and brats were in the other room. Hehe.

Slutty Babysitter

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I know I’m an evil sissy trainer but the brats shouldn’t have all the cock sucking fun. A slutty babysitter like me has needs too. When I showed up to sit for a new family last night, I could tell that the daddy was interested in me, he eyed me up and down. His pants had a huge bulge and I knew that I’d get more than money at the end of the night. After a good session with the rugrats, mommy and daddy came home. Mommy was soooo drunk and instantly stumbled to pass out in bed. The daddy came up to me and started pulling off my clothes, I made sure to tell him how good his lil ones were at cock sucking tonight and that they deserved a special treat. I led him into his daughters’ room and had him fuck my tight teen pussy on the bed while the tikes watched playing with their lil cunnies while their daddy stretched open my pussy. When he finished inside of me, I had the lil brats lick me clean.

My First Time

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Everyone always asks, “isis, how did you learn to become the most masterful sissy and slut trainer?” Well, I don’t believe in that “magicians don’t reveal their secrets” bullshit. Simply put, I was taught by the best. Growing up my parents were always gone. Always away on business, always too busy for their sweet little girl. My nanny, Myra, taught me everything I know. Ever since I remember, she trained me to be her little whore protege. My first time, she brought over our neighbor, Rick. She made him force fuck my little virgin pussy and I had to eat his cum as it dripped out of me. Every day and night, she forced me on my knees to suck cock of the many strange men she brought into the house. She stretched my pussy and asshole over and over again so that I can take as many cocks as I could. She forced me to be a slutty little gangbang whore. She would force fuck my throat with giant dildos and had me lick her pussy until she squirted all over my face. I was her best little slut, I became addicted to fucking and she taught me my place as an evil, dirty whore. She corrupted my mind and body in the best way and now it’s my turn to teach boys and girls how to be the best little cock sucking whores that they can be.

 

How to be A Good Mistress

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Becoming the best Mistress Phone sex whore takes patience.  See it was easy to tell My Husband his small cock would never be enough for me so I will go fuck men with large dick and come home to him. My way or nothing. Over the years he has even become my number one sissy.  Still he does misbehave on occasion and requires punishment.  I have come to believe in the power of cock cages and cock restriction. the harder his little peepee gets the more painful these devices are for him. and just about everything he does makes him hard around me. I even have a humbler that makes it impossible for him to move. his balls and cock are locked down while he is on his knees sucking cock. He has a mouthful and is almost crying as he moves in rhythm to the throat fuck. I let him loose so he can hold me open for one 10 inches in my pussy and an 8 inches in my ass. I love double penetration. And when They are done he will be a good cum eater and slurp every drop down. then he will run me a warm bath and bathe me and oil my aching holes. Such a good sissy and I just might let him sleep at my feet tonight! 

 

Lil Sissy Cocksucker Training

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There’s nothing I love more than teaching a boy to become a good lil Sissy cocksucker. The other night while babysitting for dear wittle Matty, I decided to invite the older neighbor. I could tell he had a thing for wittle Matty and he would be the perfect helper in training a Sissy cocksucker. I made sure to make Matty nice and pretty for our guest. I picked out a pair of frilly pink panties for him and a cute frilly dress. He hated it at first, but that’s the key, the ones that hate it at first end up becoming the perfect lil Sissy sluts. I made him up into a nice, sweet Sissy faggy and put his mother’s pink lipstick and mascara on him.

When the neighbor came over, he could hardly contain his meaty cock. He was ready for a nice cocksucking. And wittle Matty and I were ready to please. I had the lil sissy fag open his mouth nice and wide and had the older neighbor ram his 8-inch cock inside his pretty sissy pink mouth. He fought back a little- they always do… at first. But after just a bit, he couldn’t get enough of that meaty cock, he practically begged to get a shot of warm cum in his pretty lil faggy face.

Sissy Phone Sex Month of Freaks

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Listen Up my sissy phone sex freaks! It is that time of year when my sissy boys feel the freest! My pathetic little shrimp dicks can dress all slutty and say its for a party. I need sissy men who want to be humiliated and put on show! I have a nice little email for those pretty sissy boys to be showcased! [email protected]  I am looking for the prettiest faggot callers to put in my blogs. Do not fear Mistress Brooklyn will be discreet with her sissy slave boys! Cuckolding my hubby is even more fun when I can parade him about. I need humiliated little boy cocks in my email. Hell just send me that 2 inch dickie pic so I can laugh and play with My Mistress pussy as you call me to get humiliated. I got to see the itty bitty pathetic clit stick Im degrading after all. I am a very resourceful Mistress. I believe in properly humiliating my sissy sluts. I have made sissy callers cry and I love every fucking second of it. Don’t believe me call any of my fuckalicious freak whores and ask them about my Ball washer and how I made him cry becuse he couldn’t take me bragging and telling his cocksucking stories. I can be a good Mistress and humiliate you just enough so my pussy cums as you give me a spot of cum in your panties. Don’t fret I am a year round sissy training phone sex Mistress But in October My sissy Freaks come out to play with me!

Forced Feminization Phone Sex W/ Rita

I know you are craving for some really naughty mommy to make you her special little slut, aren’t you? You can deny it all you want but forced feminization phone sex is the very thing that gets your cock aching. You want me to put you in pretty silky panties and oh my the way your cock awakens when that silky fabric is taught against your flesh, or maybe we forego the panties and go for the silky sheer pantyhose and oh my the way that bulge grows when you feel those silky things on your legs, ass and groin. I almost bet the recum is dripping at this point. We then find a pretty silky cami top for you to wear or a silky slip. Oh you feel so feminine now. I will teach you the art of sucking cock next to make you a really good bitch.

Forced Feminization Phone Sex

Double Trouble with Mistress Phone Sex

mistress phone sexI am sort of a double mistress phone sex slut. I am a mistress in the sense that I mostly talk to and fuck married men. But I am also a mistress in the sense that I am a dominant tranny. My little sissy slaves must call me Mistress Carla. I like being both kinds of mistress.  One gets me spoiled, the other one gets me deep in your ass. Sometimes I am lucky, and I am both kinds of mistress with the same guy. Meet Trey. He is a 33-year-old shemale lover. He is married, submissive and rich. He has inherited money and loves to spoil sexy shemales. He is not dominant or even equal. He wants nothing more than to be treated like a subby bitch. He is a sissy closet fag. I am sure his poor wife has no clue that he is spending thousands of dollars on tranny phone sex girls like me. He paid me a visit Sunday night, but I turned him away because he came over with no tribute for me. A hot sexy shemale with a big cock deserves a tribute. He came back about an hour later with several pairs of high end shoes. That granted him admission into my kingdom. I made him worship my feet before letting him suck my hard  fat cock. He was shaking with anticipation of having my beautiful cock in his mouth.  I made him lick my ass first, then beg a few times before I skull fucked the loser. The shoes were an annoyance tax. He needs to pay me or give me nice gifts to be in my presence. Some bottom bitches aren’t so annoying. I fuck them in the ass, let them suck my dick then send them on their way. Not all bottom bitches are created equally. Understand, that if you are a bottom or just have a small dick, you may just get fucked and sent away or you may be forced to tribute me to even to talk to you if you are super pathetic.

Sissy Boy Found His Way To Me From Tumblr

Sissy Phone SexWhen I picked up I found myself talking to a very shy individual who wasn’t sure what to say. The first thing he blurted out was “I saw your Tumblr post…and I haven’t done this before” I was at first a little concerned he might start crying he sounded so nervous. I guided him through the start getting our little chat set up, I was eager to find out why he seemed so anxious. I told him to go ahead and tell me what it was that got him so on edge. He said “I saw you on https://wbmtphonesex.tumblr.com/ when I was looking for someone to help me…” he stopped there. “Help you with what?” I asked with a calm but slightly aggressive tone. “I want to be a girl…sometimes. I like panties and I like the idea of sucking cock but mostly I want to feel beautiful.”. He let out a deep breath, he seemed relieved to have gotten it all off his chest. Of course I was very willing to help him explore his femininity. We talked about colors and styles, the importance of bringing out the eyes. Especially if your going to be a cock sucker you want those eyes to pop when your looking up at the guy whos cock your sucking. Makes it so much hotter! By the end of the call he was all slutted up and ready to be fucked. Since it was his first time I went easy on him starting him off with me fucking his ass with a strap on. Just cause your a sissy you don’t want to seem like a complete bitch for a real man. I took it slow showing him how much he could enjoy with anal sex and in return he jizzed all over his new panties for me.

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