Category: Sissy Training Phone Sex

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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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!

Tweet for Chinese Food

ethnic phone sexCome make my pussy give a little Tweet Tweet. I’ve been posting some wild shit lately. It seems that I can’t get enough cock. I’ve worn out 4 sets of batteries and half a dozen cocks this week and I can’t tame this wild gash of mine. I think about cum every minute of the day. Gushing spurts down the back of my throat, volcanoes of sperm in my pussy, and a geyser in my tight puckered ass. I even booked extra massge clients so I can hear even more clit tickling stories and provide you with much needed pleasure. Care to share your massage needs with me?

Twitter lets me share some of this sexual energy. A hot Tweet can almost make me cum. Are you looking for a hypersexual slut like me? One who will share the darkest side you wish to reveal. Let’s jerk off together and have a little fun. Your cock will surely thank you.

erotic hypnosis phone sex

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!

It’s time for sissy training phone sex!

sissy training phone sexDo you know why I love sissy training phone sex so much? Because I get to humiliate a pathetic sissy of course! Just yesterday I found a whole new way to humiliate my favorite little sissy loser, she didn’t like it much but I really don’t give a shit what sissy likes or wants. You see, she says that she hates to be publicly shamed but every time I do it she squirts in her panties so I don’t believe her one little bit. I made her wear a frilly dress and shiny shoes, she had her hair in pigtails and all her sparkly girly jewelry on… she thought that I was just going to make her walk around like that but my ideas were very different. I waited until we were in the middle of a public square and then I dragged her over to a bench, made her lay across my lap and I spanked her bottom until she was squealing like a pig and begging me to stop. She made quite a scene for a girl that claims to not like being noticed and soon her whining changed from begging me to stop to begging me to allow her to fill her panties with her pathetic little squirties. What a little bitch!

Sissy Training Phone Sex Pegging Charlie

Sissy Training Phone Sex Charlie is such a pretty boy.

It’d be such a shame if he didn’t use him for his full potential. He’s already been up on stage, used, shown his place and he enjoys everything but the anal.

I take blame for that as his mother though, I’ve been so focused on teaching his sisters how to be good little sluts that I haven’t really focused any of my training efforts on Charlie.

So today we’re going to focus on stretching his ass, teaching him how to be a good little cock slut and sissy for Mommy and Granddaddy.

To get Charlie started we’ve kept him dressed up as a female, as far as anyone outside the house knows I have 4 daughters. With Charlotte and Charlie being identical twins. Of course we know that’s not true, but Charlie has also living stuffed. Pretty little plugs slowly stretching his ass so he’s ready for a cock.

Today it will be my cock, it’s little above average in size and perfect for his training (as it seems all the men who want to take my poor little Charlie’s ass seem to be monsters in the size department.) and I have made sure to put my Charlie in the mind set.

“Ready to have your pussy fucked?”

His cheeks get so red when I start this, his tongue licking nervously over his lips as he lifts the skirt he’s been wearing. I see that one of his sisters put a vibrating cock ring on him keeping him hard and dripping with precum. They were so smart, or mean, I sometimes can’t figure out which but they seem to enjoy sexually torturing their brother as much as I and Daddy do.

“What a naughty little girl I have. Look at that little bitch click leaking already.” I teased, my hand wrapping around the little shaft stroking up and down and making my little sissy whimper. Humping against my hand as I twisted the plug inside of his ass before pulling it out.

“Ready for my cock baby?” I cooed, my strap on rubbing against the puckered asshole. Spreading the lube I had put against the head to ensure a comfortable fucking for my baby boy.

His breath hitched in a way that was both sexy and adorable and he moaned as I pushed the cock head into his tight little ass. I saw it stretch around my cock and I swear he pushed back against me. What a good little slut I have!

“How long ago did the sisters put your ring on baby?” I asked, still stroking his little bitch clit. He had a hard time focusing on anything but all the pleasure but managed a breathless. “Hours…”

“Aw, poor baby, let’s make you cum.” and I felt that little cock twitch in my hand as I started to thrust into my baby boy. My cock going deeper each time until my hips touched his ass.

What a sexy little sissy I have.