Tag: Sissy training

The Sissy Olympics

Sissy Training

I love my little troublemakers; they surely help me fund my high society events. I hold the Sissy Olympics every single year, and this year I’m hopeful to see one of my own personal fuck slaves win a Gold medal in the Cum Guzzling Competition. All the renown Sissy Trainers travel from far and wide to force their feminized little fuck boys to participate in my sexy fantasy games. One might wonder what winning a Gold does for the slave; the answer? He gets one night tucked up in my bed.

Yes, that’s right. I’ll allow whatever small cocked little loser that wins the Gum Guzzling Competition to play with my pretty pussy for a whole night. I know how badly you sluts want to truly be able to pleasure me. These other trainers might allow their boys to touch them, but my whores only get that royal privilege when they’re slurping sticky cum loads from my cunt. I suggest you start practicing now if you’re thinking of trying out for the team. My sissy girls Penny, Rosie, and Ginny are sure to cum in first.
I will be, in the meantime, being worshiped by sexy BBC Alpha Bulls. Extra cum for you sluts later!

Think you can beat my own little toys? Give it a shot, you beta bitch, small balled, cuck worthy loser. See if you’re worthy of Queen Presley’s cunt.

Sissy Humiliation Training

BBC Sissy Trainer

bbc sissy trainerI am a bbc sissy trainer. If you want the bbc sissy experience, be prepared to drink a lot of protein. Black spunk is full of good protein that helps you develop a good sissy body. I make the best cum shakes too. Oliver is my newest sissy on the block. I call her Olive now. She found me through another a sissy I train. Like many of my callers, she has a fascination for those big black dicks. She watches hours of black cock porn films, including interracial cuckolding videos. I have a big bull pen of black cock studs who love to make white men black cock faggots. Trevor is a black bull who has been fucking me for years. He has no problem making white men submit to his 11.5 beer bottle thick dick either. He is a strong man. A former body builder turned personal trainer, he is a massive man who can get men and women to do anything he wants. He is not gay. He is not even bisexual. He is just a dominant black man who loves a posse of bitches and sissies worshiping his black stallion cock. Olive has only been sucking on black dildos. She has not been able to suck the real thing yet. I do not do excuses because it you want something badly enough, you will find a way to make it happen, right? Well, no more excuses for Olive. Trevor skull fucked her giving her a taste for black cock spunk. Before Olive had arrived for sissy training, Trevor had filled me up with his nutter butter. I do what all good sissy trainers do to, I pissed out the cum and made a smoothie for my sissy. Olive drank down her nutter butter smoothie while she got her anal cherry popped. Are you ready to be my BBC sissy faggot?

sissy training

His Baby Carrot Made Me Laugh

mistress phone sex

Mistress phone sex with Francis is for all you little dick men. The ones that need to be humiliated and reminded how sorry they are. The other day I had Brad over for some fun. I handed him a box and told him these are the normal condoms…put it on…look at that! Look how baggy it is! Believe it or not that little Vienna sausage was actually getting hard. So tiny, like one of those appetizers things you get at parties. I laughed and then told him to jerk it for me and fill it with cum. His sorry ass did as he was told and as he made his sad little orgasm face, I told him, good, now put that condom to your lips and drink it. He didn’t want to disappoint me and my perfect pussy and pulled that condom from his little shrimp and put it to his lips and swallowed. I laughed louder as it wasn’t even a mouth full. More like little droplets. Then I had him hold the condom next to his tiny dick and took pictures. I mean everyone needs to get a good laugh don’t they. The rubber was way bigger than his little meat hanging there. The teary eyes just made the picture a little better. Do you have a little baby carrot between your legs too? If so, you need to give me a call. I need a good giggle.

On Your Knees, Sissy Bitch!

Sissy Phone Sex

 

I have tried to be nice about it but some of you faggot bitches don’t get it!

If you want a thick hard cock in your man pussy, you have to be the sexiest, hottest femboy in town!

You want to be a sissy so you can take cock like a real sissy slut?

You want to feel that massive meat deep in your pretty ass and swallow it whole like a true lady?

You need to learn to be a submissive whore if you want to please a man! They don’t want a drama diva in sissy panties!

Oh, don’t worry!

I wont deny you that taste of man cum!

But until you can learn to be a sweet sexy sissy, the only one that is popping that man clit is me and the only cum you are eating is the spunk that you clean from my sweet pussy!

Now get on your knees sissy bitch and clean my cum filled cunt!

There is a line of cock waiting to fill it back up again!

 

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.

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.

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 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!

I Love Sissy Phone Sex Callers

sissy phone sexI love sissy phone sex calls. Sissies are the best. Every woman should be so lucky to have a sissy in her life. I have many. I have phone sissies. I have real-life sissies. And I have 2 sissy sons. My sissy sons will be shemales one day. And they will have my full support too. I can make any sissy pretty. I can turn any sissy into a shemale too. I love feminizing sissies. How can you be a sissy in man clothes, right? It is just not a look that goes well together. The first thing I do with all sissies, including my sissy boys, is put them in panties. I will not say that all sissies have small dicks, but most too. I think the lack of testosterone makes dicks smaller and lends folks to be sissies. I have met a few sissies with big dicks, but they were just sort of occasional sissies. Either they just needed something taboo to push them over the edge or they were partying. Most sissies, however, have clits. Tiny little things that no woman would want or could feel. I like to make fun of small willies as I put them in appropriate under garments. Once I have panties on a sissy, I need to find matching items like a bra and garter belt. I also enjoy a dress too. Femboy training means learning to dress like a sissy, act like a sissy and living life like a sissy. Once a sissy looks the part, she can act the part. I train all sissies how to suck cock. There are a few sissies who do not suck cock, but they are few and far between. Once you feel and look girly, you want to do girly things like suck cock. I am great at training sissies to swallow cock. My little future shemales are great cock suckers.  Sissies are like dolls to me that I can dress up and play with. Think you are ready to play?