Category: Sissy Training Phone Sex

Sissy Training Phone Sex – Luncheon

Sissy Training Phone SexOne of my favorite pansy boys contacted me today for a date. My lovely, evil mind concocted the perfect date, so I told him to put on his favorite intimates, a sexy red dress, and to make sure his bra was properly filled out, and his hair and makeup was done. He met me at the restaurant I requested, meeting each and every one of my requirements with style.

We walked in together, and heads turned immediately. It was a classy establishment, and our dresses were just this side of tasteful. We ate our meal, discussing what his goals were for the rest of the day. Little did he know what was coming.

After the waiter brought the check and he paid for it, I stood from my seat and waited for him to stand from his. Then, right there in the middle of the restaurant, I grabbed his arm and whipped him around to face me. I pushed him to his knees, being the tall fellow that he was, and I pressed his face into my breast. He quickly sprung it free and took it into his mouth like a good little bitch. I whispered for him to free his cock from under that lovely dress and start stroking it for everyone to see. He followed my orders very nicely. What he didn’t expect was for the waiter who had just served us to walk up behind him, get down on his knees, and ram his big dick into my bitch boy’s ass. He squealed into my tit before succumbing to the fucking. It was, indeed, a delicious luncheon date.

You’re in for it now sissy!

sissy phone sexOh boy, you really did it this time sissy! You’re in for a harsh fucking punishment now that’s for sure, there is just no way that I am going to allow you to get away with ruining not only my favorite nightgown but also my favorite fucking vibrator as well! You know very well that I will not use anything that you have used, especially when you cover my nightgown with cum and my vibrator has been in your ass! Fucking disgusting is what it is and now I need to teach you a harsh lesson. Now I am going to have to force you to do the one thing you always say you will never do… you are going to be sucking all kinds of dicks! Yeah, yeah, I know you think you aren’t gay but you are the biggest sissy bitch faggot I have ever met! Hope you’re ready because I see a whole lot of cocks in your future!

You will bow down for Mistress Adriana

sissy phone sexOh sissy, no matter what you think you’re going to do, you WILL bow down for me! Just look at you, you’re effeminate and wimpy and weak… you look like a little bitch and quite frankly sissy there is nothing even remotely manly about you at all! You know I’m right no matter how much it hurts you to hear it so quit all of your whining and get dressed. I need to get you looking perfect before my guests arrive, this is a big night for you and I worked very hard to set it up so you had better be grateful. I expect you to immediately get down on your knees for any man that asks you, I want to see you eagerly swallowing every inch of their cocks too! You are gonna swallow every load, no spitting any out either because good whores always swallow every drop. When I finally decide that you’ve had enough you are going to get down on your knees and humbly thank me for allowing you to be of service to me. You are going to learn your place sissy… whether you want to or not.

Do I look like a housewife to you??

humiliation phone sexYesterday was Housewife Day and I wanted to celebrate it but lets face it, I’m no housewife. I don’t cook or clean or cater to anyone, why should I? I am too beautiful to dirty my hands like that and besides that is what I have little sissy bitches for! I had an entire party set up filled with other beautiful women like me and they all had a wimpy little bitch boy with them. Those “men” thought they hit the jackpot! They were all convinced that we were attracted to them and just on a regular date but that couldn’t be further from the truth. Those little wimpy “men” all had a secret that they thought we didn’t know… they all liked to secretly cross dress. Women like us can sniff those little fairies out easily and when it came time to out them all none of them even attempted to deny it. We forced them all to strip out of their fake man clothes and put on their slutty little dresses for a very special photo shoot… I wonder if their families will like the pictures…

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Sissy Phone Sex with Sexy GFE Shannon

Sissy phone sexLately, I’ve been getting more and more calls from these sissified men who just want to feel pretty and wanted. I will admit, it gives me a bit of a thrill. Most of the guys I’ve had up til recently had been macho men who just wanted arm candy to walk around and make them look good, someone who would look amazing on their cocks. These sissy men have been treating me like a goddess, and it has been amazing. They will come to me and submit gratefully to my ministrations. They let me bathe them from head to toe, dress them in beautiful intimates and stunning dresses. I get to do their makeup, style their hair, and help them on with their stockings and shoes. Then, I get the privilege of walking out with them, seeing mens’ reactions to the beauty we have created. I get the enjoyment of watching cocks get hard over an illusion that my darling lover had an urge to portray. My favorite part, though, has been getting to take my lovers back home with me, and having friends or even strangers come in and have their way with my lovers while I get to get myself off using whatever appendages and methods I want.

Sissy Training Phone Sex with Shannon

Sissy training phone sexMy sissy boy lover came back to call. My problem was that he came dressed down, looking a little frumpy for my tastes in some jeans and a t-shirt. So, I pulled him inside and put him on the floor. On his hands and knees, I undressed him before spanking his tight little ass for showing up so shoddily attired. When I finally had him down to his bare skin and had sufficiently punished him for his lack of good judgment, I pulled out an outfit I had made him leave here in the past. I handed him the box, and ordered him to get dressed right there in front of me.

He pulled the panties on first, tucking his cock gingerly into the thickest part before adjusting the g-string into his ass crack. Then, he put his bra on, filling it out with the little silicone pads I had found for him. At this point, I told him to stop and follow me. When we got to the bathroom, I pulled a razor and my shaving gel out of the cabinet. I forced him to shave, and watched as he did it. I popped his ass every time he missed a spot, and he missed a few.

Once he finished shaving, I brought him back into the living room, and held his dress up for him. He pulled the sexy, slinky little pale blue slip of a dress up his legs and over his hips. The dress hugged every curve of his sweet body, and his hard cock was a bulge pressed against it. When he had finally finished dressing, I brought out the wig I had bought just for him. It was close to his natural medium brown, but with some natural red shot through it. It was a sleek style that would complement his facial structure. I sat him at my vanity, and watched patiently as he put on makeup, receiving approval for each item before using it. He was such a sexy sissy. When he finished, I rewarded him with my pussy on his face.

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.

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!

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