Category: Sissy Phone Sex

Babysitting or Training session?

 

Sissy Training Phone Sex

I hate watching boys. Puberty has them going wild and honestly if it walks and talks I really don’t want anything to do with them. I like them so young they can’t say no! I was watching Chris. The annoying bitch boy who hated it and threw a fucking fit every time his mommy and daddy left. They knew he was a monster just like I did. This little shit was acting like a pussy ass bitch. Crying and screaming on the floor. I grabbed him by his ear and pulled him up off the ground, Almost ripping it off. Slapped his little bitch face which shut him up. I told him if he was going to act like a little crying bitch he was going to be treated like one. I had my costume wig with me for Halloween and I put it on him. We went into his precious mommies room and put her make up on him. He kept screaming and crying as I was trying to do his make up. Its ruined, tear running down his face. I slapped him again and dressed him in his mommies clothes. Made him duct tape his tiny cock back by his asshole. Put on a thong and a bra as well as a sexy see through nighty. Strapped some heels on him and shoved him outside. I made this crying bitch walk up to each one of his neighbors and tell them what he was. ” I am Christina, your new neighbor. I am a sissy faggot whore. Can I suck your cock?” He was a brand new sissy bitch and he was going to be trained so well!

Mistress Adriana knows sissy phone sex

sissy phone sexI am a sissy phone sex expert, I’ve been doing this shit for years so do not ever presume that you know better than I do sissy! You are a wimpy little bitch boy that wishes he could be as beautiful as I am… news flash loser, you will never look like me! Me allowing you to be dressed up and used in our sissy phone sex call is about the best that you can hope for and you know it as well as I do. You are not going to get babied during our sissy phone sex call either so don’t even expect that shit. I am a bitch and we all know it, if you are calling me it is for abuse and humiliation and degradation, not some foofy baby talking bullshit you may get elsewhere. I have never been the type of mistress that will hold your hand and be nice to you… you are my sissy slave, nothing more than a whore and that makes you beneath me!  So get dressed sissy and get on your knees ready to worship me!

Mommy’s Sissy Phone Sex

Sissy Phone SexCharlie’s such a good Sissy Phone Sex slut and doing training with mommy is paying off so much.

Daddy and I decided that maybe it was time to let Charlie have her first client since that… more than a little painful experience the last time she was on stage.

She was a little afraid, not having a real cock in her ass since that night but Daddy and I assured her that she’d be fine.

That this person would be gentle and love her tight little ass and cock.

So, I dressed up my little Charlie. Using a pretty satin pink dress with a sparkly hair bow. I put on a pair of white cotton panties with a matching pink bow on the front and a pair of shiny black mary janes. Before doing a simple and very natural makeup on her. She didn’t need much, she looked so much like her twin sister. Full pink lips, smooth cream colored skin, big blue eyes with long eyelashes, and naturally curly blonde hair.

She was such a sexy little Sissy Phone Sex whore and I could tell she was excited and nervous as her “Date” knocked on the door. I opened it to find our friend, he was a tall man and built like a tower. All muscle, beard, and intimidation.

I had a moment of uncertainty but he was paying us a lot to play with our Charlie so I invited him in. He smiled warmly at our nervous sissy and Carlie said hello with a cute blush and shuffle of her feet.

The man squatted in front of Charlie. “What’s wrong little one? You look scared.”

Charlie blushed brighter and smiled weakly at the man. “It’s… You’re big and…” she looked down shyly at floor, refusing to meet the man’s eyes.

“Well… Why don’t I give you a preview of our night tonight and we’ll see if you’re still scared of going with me?”

Charlie looked at the man surprised. “We can do that?” she looked at me after. “Would it be okay?”

I laughed, “Of course!” I agreed, liking the idea of seeing this man with my little girl.

So the man took Charlie’s hand. Her hand looked so tiny in his and led Charlie to the couch having her kneel on the cushions as he knelt in front of charlie. He lifted her skirt and rubbed his huge hands from Charlie’s little cock to the back. Cupping his ass, finger pressing up and against Charlie’s little asshole.

“Oh…” Charlie breathed, squirming against the man’s hand as he leaned forward. Licking a wet spot along the hardening little cock underneath. His hands moving to pull the panties down to his thighs. Sucking on his middle finger for a moment before returning it to massage against the little asshole. Pushing a finger in as the man takes the entirety of Charlie’s cock and little balls in his mouth. Sucking and licking and making Charlie moan and hump against the man’s face.

It only took a moment for him to cum, but he more than happy to go with the man after that. I can only imagine the amount of fucking that happened that night with my perfect little Sissy Phone Sex slut.

Sissy Phone Sex with a Princess

I recently had a call from a great guy. He treated me right from the outset. I never opened a door, never spent a dime out of my pocket, and he made me feel like I was the only girl in the room every place we went.

Naturally, when he called up requesting another date last Saturday night, I said yes. Imagine my surprise when a rather attractive female showed up at my door dressed as well as I was. When he spoke, I instantly recognized what was going on, and we proceeded with our date as planned.


When the date was over, after another lovely night of him treating me like a lady, I invited him up for coffee. He accepted, and followed me directly upstairs. When he closed the door behind us, he immediately dropped to his stockinged knees on my floor and assumed a submissive position. He begged me, right then and there, to make him my little bitch boy. He even shed tears, he begged so prettily.Sissy phone sex

I made him crawl into the living room with me and start taking my shoes and stockings off. Then, I had him kiss my feet and lick my toes. At one point, his teeth scraped across my foot in the process of him licking, so I made him climb across my lap and take a spanking.

I felt his hard cock pressing against my legs as soon as he lay across my lap, and when he got back up, I gave that a quick smack, too. We had lots of fun that night, but I’ll post more about it later. I need to go for now.

Let me tell you about my new sissy phone sex caller

sissy phone sexLet me tell you all about my newest sissy phone sex caller, she calls herself Candi Slut and she is the most ridiculous sissy I have ever seen! See, here’s the thing about sissy phone sex, it doesn’t always go the way you want it to and trust me, this sissy learned that the hard way! She said that she hadn’t been feminized in quite a while, poor little sissy had moved away from her previous Mistress and thought that she could just go back to being her “alpha male” self. Hahaha oh man, did I ever laugh at that shit! This little bitch has a tiny penis and a feminine attitude, there is NOTHING alpha male about her at all! She didn’t like that I laughed at her pathetic little penis, she tried to say it was big but I made her admit the truth… and the truth is that it is the smallest dick I have ever seen! I forced that sissy to fuck herself with a nice big rubber cock as punishment and even though she tried to say that it was way too big and that it was hurting her, she kept on with it and soon was leaking her precum everywhere! You see sissy? Mistress really does know best! And that is something you would do well to remember during our next sissy phone sex call!

sissy phone sex

This tranny loves sucking cock.

tranny phone sexI loved the way you were sucking my cock. Slowly, barely nipping at the head, as you swirled your tongue across my smooth balls. You said you had never been with a tranny so I was kinda surprised when you begged for a taste of my 8 inch meat stick. You were an eager little faggot, almost whimpering with desire. I let you suck for a few minutes but I wanted more. I was wondering how much meat you were packing in those tight Wranglers. You peeled them off quickly as I joyfully discovered a meaty, thick 9 inch cock. You didn’t resist as I gave you your first tranny blowjob. I moved on to your puckered man pussy. I already knew how good it felt to penetrate and violate an anal virgin and my dick throbbed in anticipation. I tasted your pink starfish and it was so good. I delved my tongue deeply, rolling it up to tongue fuck your pussy. I grabbed your ass cheeks and slapped my cock against them, aiming for the bullseye. Your squealed in pain and pleasure as I gave you what you needed. You were so tight that I knew I was going to blow. I pulled away as you begin to shudder, your balls pulling up tight. Not wanting to waste your juice, I wrapped my lips around your cock and began to suck like a cum crazy whore. Your moans of pleasure almost made me lose my load. I savored every drop and stood up to kiss you, making you sample your own cum. Then it was time to finish what I started. I spun you back around and bent you over, sinking to the hilt in tight virgin booty. This night was just getting started.

 

I just got a brand new maid!

sissy phone sexI just got a brand new maid, and the best part is that she is a little sissy slave girl so I don’t even have to pay her! I literally own this bitch right here and there is not a damn thing she can do about it. See, this little sissy bitch used to be married to a good friend of mine, but my poor friend had to deal with finding out that her new husband not only had the tiniest little wannabe dickie she had ever seen, but she also had to deal with the fact that her new husband was a cross dressing, dick sucking sissy faggot! How fucked up is that?? Ladies, never wait till marriage to fuck your men or shit like this can happen! Anyway, she didn’t want to be with a faggot like that so she gave him to me. So now I have the little bitch wearing a french maid costume while she scrubs my floors, if she does a very good job, I will reward her with lots of big fat cocks to suck and fuck!

Have you tried crossdressing phone sex yet?

crossdressing phone sexLook at you, you’re just a wimpy, little dick sissy boy that is a perfect candidate for crossdressing phone sex! With that tiny little penis, you definitely are no kind of man so you may as well just give in and become the sissy you were always meant to be! Oh what’s that? You are a real man? You don’t want to be a sissy??? Hahahaha I don’t give a fuck what you want bitch! You have a tiny little dick, it’s more of a clit really so you will never ever be a real man! No woman, especially a woman like me, will ever fuck you or even allow you to touch her with that nasty little baby dickie. Women like me like a big fat cock… as a matter of fact… let me bring in a REAL man with a big fat cock. He can show you the differences between you and even help me dress you up in something frilly and feminine. I will give you a complete makeover and you will see how good it feels to give in and be the sissy you were always meant to be. By the end of this, you will be sucking dick and begging to get your little man pussy’s cherry popped!

sissy phone sex

Tranny Slip n Slide

tranny phone sex

I think covering a slip n slide with cum would be the ultimate ride. Can you imagine how much cum that would take? A whole row of sexy tranny girls in bikinis stroking their cocks as you slide past, catching some cum on your tongue as they spurt hot loads all over the mat. I bet some of you sissy boys would be lapping it up like ice cream.  The idea of rolling around in a cum bath until we are all lubricated is so hot. Lots of tranny tits and round tranny ass humping some dirty little faggots and milking those loads too. Our sexual slip n slide is the best ride in town. Slide on down and let me wait at the end with my cock sticking straight out and ready for your pussy. I’ll bust that cherry with a loud pop as you scream. Soon those screams will be garbled moans as you get the ride of your life. What a summer fantasy!!!

Bow down you little bitch!

small cock humiliation phone sexListen up you pathetic little sissy bitch, you are my whore and as such you will worship me… you will never ever get to fuck me! I seriously can not believe that a little bitch like you would have balls enough to ask me if you could fuck this pussy. That tiny little worm between your thighs is much too small for a woman like me to even want to touch it, let alone fuck it! I need a big cock and a real man and trust me whore you are no kind of man and your cock is barely a clitty so you better just get down on your knees now and beg me for forgiveness. Otherwise I may not even let you touch that nasty little dicky of yours!