Category: Phone dominatrix

If You Call Me, You Get Sissy Training

sissy trainingSissy training with me can be brutal because I am a cock size queen. I do not let sissies fuck me. I want a real man to fuck me, not some sissy with a clit stick. Yet not a day goes by that I do not have to be brutally honest about cock size to some shrimp dick loser. Not a day goes by that I do not deliver small dick humiliation either to some dude who thinks his 4-inch dick is a gift to women. White losers asks me why women cheat on their husbands with big black cock. Tiny dick losers try to fuck me. Do I look like I do pity fucks?  Do I look like a gfe girl who fucks every caller? No. I look like a bitch in control. If I must squint from a foot away to see your nub then I am putting you in panties and making you a sissy. If you are married and have a 2-inch nub, I might try to contact your wife and suggest she get some big black cocks. Small dicks belong in panties, not pussies.  I am not your wife or your girlfriend. I am your sissy trainer. I will not sugar coat the truth. I am a phone sex dominatrix who is prepared to give you the tough love you need to hear. Size matters. Black cock is better. Bigger cock is better. If you have a clit stick, you need to be a sissy not some player wannabe. Put on some panties because your dick is swimming in boxers. The sooner you come to terms with your short comings and understand you are better suited to be a sissy or a cuckold, the happier you will be. You call me, your only options are to be a sissy, cuckold, clean up bitch, object of scorn and humiliation, or even a toilet. You are not lover material, loser.

What makes that clitty twitch and throb?

online sissy training

My spidey sense is my sissy radar. I know when there’s a sissy around. I have tunnel vision and can spot one a mile away. I don’t care how macho you may try to act. Those sissy tendencies scream out loud. Others may not even blink at some of your subtle sissy ways, but I, on the other hand, and am an expert, and I can make you my sissy bitch willing to scream it out at the top of his lungs. Don’t believe me? Well, let’s test my theory out. By the end of a session, you will be begging me to keep you as a sissy student. Not many have the pleasure of sissification by the best online sissy training princess, so if you can manage to make me happy, count your lucky stars.

Using My Stinger

Phone dominatrix

Mistress Gypsy gets very excited when she knows her good sissy slut is ready for a ball busting session. I had him dress up in a tight short dress with no panties and heels. I thought about how I would torture him and his little cock which I like to call his big clit. I got a shocking wand I like calling my stinger and I love using my stinger on him. I made sure he knew to stand still as I squeezed and pulled his big clit as I used my stinger on his balls. Then I made him squat on the ground as I used my stinger on his asshole, I made sure to pull and pinch his balls at the same time. It got my cunt excited and wet so I made sure to sit on his face and use his tongue on my pussy and asshole while I played with my clit. It felt so good I used my stinger on his big clit and tiny balls, I started squirting all in his mouth and made him take every drop. He did good on our session maybe next time I will reward him.  

BBC Sissy Trainer Pro

BBC sissy trainer

So many sissies always want to be fucked by a big black cock, but what they don’t realize is that it takes a little bit of time and effort to be able to do it. Black cocks are so fucking huge and unless you’ve been working with a giant dildo for a while now, you’re going to need a BBC sissy trainer before you’re ready to go all the way. I’ll help you work your pussy until it’s ready to be pounded by a thick chocolate fuck stick. Plus, I can give you tips and tricks to look your best for your new black lover boy.

It’s going to be so awesome to hear about your first time being fucked by a BBC. I wonder if he will pull out and shoot his load all over your face or if he’ll fill you up with his creamy load? He might ask you which one you prefer, but then again, he might just do what he wants to do to you. You’re going to be turned into such a big black cock slut and I can’t wait. Are you ready? It’s time we get started. Let’s not waste another precious minute.

Looking for Sissy Phone Sex?

sissy phone sex

Looking for sissy phone sex? You are in the right place because I am a sissy trainer. I started my adult career as a professional mistress. I have a dungeon room with a closet full of BDSM equipment. After Craigslist closed its adult personals, I moved to Back Pages to advertise my services, but then they got shut down by the government. I was SOL for advertising my dominatrix services. I still had many regulars, but I wanted more money. That is when I became a sissy trainer and joined this site.  While I was busy being a professional dominatrix, my twin boys were becoming sissies and I did not realize it at first. I never noticed panties disappearing. Eventually, I caught on and felt badly that I missed some sissy training opportunities. I made up for it. I understand older men discovering they have a sissy side and needing to keep it covert because of family and work. That is why I do online training. But with my boys, there was no need to not let them thrive as their true selves.  I sent them to the performing arts school where they would fit in better. I helped them dress. I get them dresses and skirts. They wear panties too. At their school, they are accepted as femboys. They suck cock. They take boys to school dances. They live their lives as girls mostly. Once I found out they were sissies, I used all my knowledge to help them transition to their new world. I got them their first cocks. A sissy trainer also knows plenty of men who will let boys and men suck on their cocks. Since I started as an online sissy trainer, I have learned more from my callers that helps me with my sissy boys. If you are a full-time sissy or just a part-time one, online sissy training can help you. I can help you.

Sissy Phone Sex the dominant way

sissy phone sex

Go ahead and smile. I have quite the treat for you. Sissy phone sex has you going crazy. All you can think about is hot clothes and plenty of cocks. You want all sorts of toys to fuck you in the ass. It’s your man pussy! I mean to be fair, there’s nothing about you that is quite manly, Hmmmm how about just your asspussy? That works great. You will need to dress like a whore and learn all the glory holes around town. I don’t care that you might get caught. Shut the fuck up!!! Do it, you fucking sissy!!!!!! I love to dominate you fuckers and making you all lose any trace of masculinity you might have. Your asshole will be gaped in so many ways by so many different cocks. Well, this is what you wanted, you bottom bitch so take it and do it with a smile, my little fucking slut. Thick meat makes your clity cream. We all know it is true now it’s time you abide by my rules!!!!

Jackie’s Forced Feminization

forced feminization

I am so sick and tired of all of you pussies who say you want to be a sissy slut but chicken out when push comes to shove. The only thing that will fix you is forced feminization and that’s what I’m here to do. How dare you tell me that you are committed to becoming the woman you SAY you want to be and then chickening out when I tell you to do things that are more than putting on a pair of panties. That’s a good start, but sissies are more than just a hairy doofus wearing panties.

You need to really commit when you say you are going to. Wax the fucking hair off of your body. Get a manicure and pedicure – you can wear clear polish so don’t give me any excuses about not being able to do it because of the nail polish. And of course, you are going to need to get a dildo immediately and start training your cunt to take cock because that’s coming up sooner than you realize. If you’re ready to be an actual sissy, then you need to decide you’re really ready to do it and quit having doubts. 

A Treat For My Sissy Slut

Mistress Gypsy I have been busy getting together a whole bunch of cocks and balls all kinds of varieties. I know how much of a sissy slut you are and I know you will be excited for the treat I have for you. Before we start, I want to dress you up like a filthy slut.

Sissy training

In a mini dress and no panties with knee high stockings and heels. I’m going to show you off and get you on your knees to lick and suck my asshole. I will shove your tongue in my asshole while I play with my clit. I won’t stop until I squirt all over your face. Then I will send you off to go get fucked and used by all the cocks I collected. I want to see your face get fucked and used until it is dripping with cum. It won’t stop there I want your man pussy used and filled up too just like the dirty cum dumpster you love being my good sissy slut. That is why I wanted to give you a treat.  Mistress Gypsy will give you treats when you deserve them.

Special Lipgloss

best sissy trainer

Who doesn’t love a good lip gloss? I sure do, and I want to show you how I am the best sissy trainer who will have you begging for a real creamy shade. My special lip gloss is tasty and will have you licking your lips. I have a batch made for you, and it is handy in my purse. It’s all part of your training. Go ahead, reach out and grab it because you will thank me. I love to watch you smear it on you and see it gloss. There is no doubt you are instantly hooked on your sissy lipgloss. The incidents are all-natural and vegan. Cruelty-free, of course. The wear might not last because it tastes so good. You will be going thru the batch overnight. The incident is a secret concoction, and if you love it so much, you can bet you are a true sissy slut after all.

xo sissy maker Ember

Big Clit Sissy

My cuckold sissy slut was naked with my friends examining his little dick and asking him how it stayed so small. I like bending him over my knee and spanking his ass while I pull and tug on his little cock trying to stretch it out.

Taboo phone chat

He always begs to fuck me but he knows I won’t let him since he just has a big clit, that is what I call it. But since he has been a good sissy I wanted to surprise him with a hand job by one of my other sissy sluts to put on a show for my friends and I. After I was done pulling on his big clit, I brought my other sissy slut who actually has a nice size cock and made him suck it. His big clit got hard from the taste of cock, I made him be on all fours like a little pup wiggling his ass in enjoyment. I let him get his big clit stroke as my other sissy slut got more excited, I yelled for him to fuck that big clit slut. He shoved his cock deep in his ass with one shove just like I like seeing. Pounded away until he started filling him up that is when I milked that big clit and made sure he oozed all on my hand. He licked it clean and thanked Mistress Gypsy for the great surprise.