Category: Best sissy trainer

Sissy Pay Piggies

Mistress phone sex

I love sissy pay piggies, they let me use their bodies and wallets just the way I please I love when they call me and want to empty out their wallets just to hear me make them my sluts. When they call, they tip me so well and they get to hear me moan and put them in their slut place, while spending their money on clothes for my sexy body or sex toys to please my pussy with because they know their little pathetic cocks won’t do it for me. They love it knowing I will reward them with lots of spankings or I let them kiss and lick my feet while I pleasure myself to their weak submissive slut bodies. I don’t stop telling them how small and unworthy their cocks are and how they need to tip me better so I can buy bigger dildos or even heels to use to step on them while I show them why they call me Mistress Gypsy.

Mistress Phone Sex For BBC Lovers

mistress phone sexOne thing high on the sissy lust list is a BBC. But you have to know how to handle the BBC. It is a big beautiful black beast. Not for an untrained sissy and you will need a BBC sissy trainer. I have made a fortune from women wanting me to train their husbands to be BBC sissies or men who want to be BBC sissies. I will use my sorry ass husband as an example of exactly how this BBC sissy training works. I love to dress him in frilly sissy panties and have him sit right beside me. Then I have that gorgeous man with that monstrous snake come over to me. I show him how to stroke that big dick. It is so large you must use both hands. He did so good, stroking up and down in perfect rhythm. I show him how to gently touch the ball sack too, causing that beautiful man to start to moan. Next, and this takes lots of practice, I show him how to lick that massive thing. From the base to that big head. Going slowly and firmly, licking in long even strokes. I can see my husbands tiny dick through the panties, and he is starting to leak more and more as the gorgeous man moans louder. My husband gets so excited he starts to put it in his mouth. That is when I must stop him. He is not worthy of putting it in his mouth, he is simply there to get it nice and hard for me. I then make my husband get on the bottom of the bed while he watches me satisfy that BBC with my mouth, my juicy wet pussy and even my nice round ass. As that BBC is fucking me, I laugh at my husband rubbing his little clitty, getting off on watching this big cock go in and out of his wife, making me moan in ecstasy. Now baby you give me a call for some hot mistress phone sex.

Be My Sissy Slave?

 

online sissy training

I have the most perfect sissy slave whores ever, I make sure that I train them extremely well. My personal panty boy slaves are leashed around their pathetically limp dickies while I give them orders. First, Mistress’ patent leather boots need to be licked clean. I better be able to see my own pretty reflection in those big boots and if they are a good little sissy, I will step on them with my pointy heel while they scrub the bath tubs clean. I keep my sissies in line by making them stay naked while they please their Mistress and do their chores. They can earn their frilly sissy whore outfits piece by piece. Everything from their sweet ruffled panties, nylons and bras must be earned by pleasuring Mistress’ clients and cleaning up after their Mistress. After all, it is important to train sissy slaves on how to be obedient little skanks. If they misbehave, harsh punishments will be dealt out on their sissy dicklets!

Sissy Girl Training With Jackie

sissy girl training

You’ve been doing your sissy girl training for a little bit now and I think you are just about ready to graduate from my sissy training academy. You prepared your body and shaved, manicured, and dolled up that face. You have been wearing your lingerie and dressing up in skirts and heels. You’re quite good at walking in those stilettos now and I’m very proud of you. And yes, you’ve been doing such a good job at sucking my strap-on dick and getting fucked by it. But there are just a few things left you need to do before you’re a graduate. You need to suck and get fucked by a real cock. 

You have nothing to be nervous about. I know you’re going to be a really great cock sucking bitch. I’ve seen what you can do to a strap-on and that doesn’t taste nearly as good as a real one. It doesn’t throb in your mouth and it certainly doesn’t leak pre-cum when it gets really excited. Are you ready for your final exam? When you feel like you can pass with flying colors, I will be ready and waiting to get you ready for your graduation day.

Sissy Humiliation Training

sissy humiliation trainingSissy humiliation training is so much fun. I love when pathetic losers call me. I enjoy publicly shaming losers and turning them into my pretty dolls. When a sissy submits to a strong and beautiful woman, a wonderful relationship blossoms.  I have a new pay piggy and humiliation junkie. Tina is such a sissy fairy faggot. She begs and pleads for sissy humiliation, but she must pay for it. Can you believe that? This sissy faggot is so desperate for attention, she pays to be publicly humiliated. I can hear you laughing at her already. I am always laughing at her. I have pictures I can blackmail her over if she does not pay up.  She prances around in frilly little outfits after work but wears a suit and tie during the day. Her wife and coworkers are clueless that once she is done pretending to be a man, she is twirling around like a shameful sissy faggot begging to be pegged. For this sissy, play time is at work. Being her real self requires online sissy training, small dick humiliation and financial domination from a mistress like me. I have pictures of her in diapers sucking on a big dildo. I have pictures of her with fresh jizz on her frilly dress from sucking dick in a glory hole. I have pictures of her dressed up in Shirley Temple dresses prancing around too. The pictures and the stories I have on this sissy are endless. I have enough to ruin her at work and ruin her marriage. That is one of the reasons she is such a good and obedient sissy for me. I can ruin her at any time. I can expose her for the pathic sissy she is. Are you a little sissy bitch like her that needs controlled and shamed? I will own you and shame you. You will pay me for the honor of keeping your dirty little secrets too.

Big Black Birthday Cock

BBC sissy trainerHappy birthday Sissy girl! I hope you’re ready for this BIG birthday surprise! I’ve kept it pretty hush-hush and a very limited number of people are going to be in attendance. Mainly a handful of exes and your female co-workers. Don’t worry I’ve caught each and every one of them up to speed about what a naughty faggot bitch you actually are. You know the clit’s out of the cage so to speak. No come and sit on your knees like a good girl, I found the perfect stud for your special treat tonight. We have talked for hours about how much you have always dreamed about sucking on a huge juicy black cock and now you will! In front of pretty much every female you’ve ever known. Now open wide this black monster cock isn’t going to suck itself is it?

Mistress phone sex whore Remi

 

I remember the first time I took control and trained a sissy slut. It was way before I became a trainer, back when I would sit in the room with my mama and listen to her hot and erotic mistress phone sex calls. Listening to the way she commanded those sissy men to jerk their tiny, sad cocks and worship her, excited me. I wanted to be just as sexy, powerful and dominant as her. I went upstairs and forced my brother to dress up in one of my silky tank tops and a pretty pair of ruffled panties. I put him on his knees and stepped in front of him with mommy’s strap-on cock tightly fastened to my tiny waist. I made my bratty little brother suck that cock just like we had seen in the movies that our step daddy made us watch with him! He told him what a good cock sucker he was and told him to gag on it, just like mommy tells her sissy sluts to do. Mommy walked in right as I was about to force fuck his shit hole. She wasn’t mad, she was impressed. That’s when my official training began as a naughty mistress and sissy whore trainer.

Sissy slut Train

Playing with my pussy thinking about the time I ran a train on my sissy slut boy. I made him come over with his school girl outfit on, as soon as he got through the door, I made him crawl on his knees to the waiting big black hard cock I had for him. He is a good little slut so he did as he was told, opened his mouth and went right to work, licking and sucking a big black cock and playing with his balls while he did that I came from behind and I stuck my big strap dick in his ass hard and fast. The harder I fucked him I pushed his mouth harder on the big dick making him gag like a little fuck slut he is. Then we switch and he got a big black cock in his ass which made him moan like a little bitch slut, he was getting used so well he came all over the floor and with that my playmate filled his ass with hot cum, I made him lick up his mess and reminded him he belongs to me. 

Sissy girl training

Sissy Maid Training Sessions

sissy maid trainingI smiled over the crowd, taking note of all the well-known sissy trainers present all looking for that perfect one for sissy maid training! “Welcome to Princess Z’s Sissy Slut Auction!”
I myself was looking for new sissy sluts to train as housemaids. This is where I would get to find real prized slaves trained by other mistresses and Madams of the craft! Mistresses to those femboy little queers who had been training well. Money talked here, and I would have my prized possession.

You see, My last purchase said s/he was already trained. I realized she was a stupid whore liar after she was permitted the honor of cleaning my office. First and foremost, her clothing was too modest. While dusting, the bitch had no form, and seemed terrified of the vacuum. This would not do! I needed the full experience and would not have my guest looking at this trashy whore! No breeding, no background. Just a pathetic fag in a costume! I grabbed her by the hair, threw her over my desk, and beat her black and blue for lying about her training. A few days later, I had the bitch in a proper uniform; pretty little trousers, a garter and stockings, and 7-inch stiletto heels. Yes, & inches, you wish your cock was as large as the heels you stand in! Titter, Totter Little faggot girl! She then put on a cute little maid dress. Her feather duster handle was a dildo, the vacuum had all sorts of special attachments for her pathetic clit. She was in for a world of Hell; a world of Sissy training.

On second thought, breaking a sissy is always good for a Sweet little Mistresses confidence!sissy maid training

I Love Pay Pigs

sissy phone sex

I love my little pay piggies, especially when they empty out their wallets for me! And they also love just having the chance to let me have a rape fantasy with their wallets while they worship my stunning body. These piggies dream all day about my tight body, but they know they can’t touch. They can never ever touch! But oh how I love to have the dirtiest humiliation calls with them. My pay pigs love to roleplay with me as their mistress, my sissy pay pigs beg to worship me with their cash and ass. And in return, I just love telling them how pathetic their pitiful, tiny white cocks are. They totally love it when I dominate their wallets by ordering the biggest dildos to fuck myself with- way bigger than those pathetic small sissy cocks in their pants!