1,509 results for sissy training

Anal Sissy Training with a Pogo Stick

sissy trainingAnal sissy training is so much fun. I have had a few unruly sissies who have protested my methods of anal training. You cannot be a good sissy if you cannot take a cock in your ass. I trained my own asshole to take big black cocks. A good sissy wants cock up her back door pussy. I had this one sissy about 5 years ago who wanted me to train her ass with unusual objects and large objects too. I was struggling to find things to fit in her asshole. This sissy had a cavern for a back door pussy. Her asshole was so big that a foot long black cock would feel small. I was not going to be defeated. I was going to find something to stuff that sissy ass. I have this belief that sissy training asses is key to being a good sissy. It is a sissy’s tightest hole. Well, not for this one sissy. One day, I saw my daughter in the backyard on her pogo stick and a light bulb went off. It was pink too. I thought okay it is a weird thing to put up even a sissy’s ass, but it was big enough to maybe stuff that sissy’s huge back door pussy. The next time my sissy was over for some anal training, I was ready. Readier than I had ever been. She fell in love with the pink pogo stick. When my sissy first saw it, she misunderstood its use. It was not to bounce around entertaining me. That pretty pink pogo stick was for anal sissy training. It was the first time I ever saw her eyes that huge. She could not believe I was going to try to put that up her back door hole. Plenty of lube and some deep breaths, anything will fit in any hole. I gave her a few shots of whisky. My sissy took it like a champ. I could not get it all up her ass, but she took far more than I thought she would. I finally found something to fit the gaping asshole of that sissy. I was so proud of myself. Trust me, I am a great sissy trainer. I will find something to gape your asshole too.

sissy training

Sometimes Forced Sissy Training Is All It Takes

forced sissy training

Some of you think you want to be a sissy slut but you back out when things get real. So I think you’re in dire need of some forced sissy training. When you call me, you won’t be able to back out of it. You’re going to be fully feminized from the top of your head to your hot pink toes. I won’t take no for an answer, no matter how much you beg. When it comes to something like that, begging is not something I love. Now, if you get on your knees and beg for cock, that’s more my style.

And speaking of cock, you’re going to be getting up close and personal with dicks. I hope you’re ready to learn to suck big fat cocks, because that’s the only kind I like. I’m a size queen and I plan on turning you into one, too. You have no choice in the matter, just like you have no choice in anything else I make you do. Do you think you could handle a forced feminization Mistress like me? There’s only one way to find out if you’ve got what it takes to be a sissy slut – pick up the phone and we’ll figure it out.

Online Sissy Training for Sissies, Cucks and Small Dick Losers

online sissy training Online sissy training begins here. I want to make it clear that training sissies is not all I do. Yes, I love being a sissy trainer and I have decades of experience, but I love small dick humiliation and cuckolding too. Sometimes, you get a guy who enjoys all of it. The trifecta of humiliation. You can be a sissy, a cuckold and a tiny dick loser at the same time. And yes, I can prepare you for it all. Todd, who I now call Tina, has been coming to see me for almost a two years now. I met her because she is married to my bestie. My girlfriend confided in me about her husband’s lack of equipment and his refusal to eat pussy. I had to have a talk with them both. It was not an easy resolution. It took over a year to transform Todd into Tina, but now my BFF has a sissy maid and a cuckold, and I have a small dick loser I can laugh at and tout as a success story. If you are wondering how the trifecta of sissy training, cuckolding and small dick humiliation work together it is simple. Sissies and cuckolds both suck cock. Mostly, they both have small dicks too which is why their partners do not want to fuck them. Just add some pretty clothes and a cheating partner and you have a sissy cuck. Tina is everything I could want in a sissy. She cleans house. She cleans dirty cunts. She fluffs cock. She procures cock and wears frilly things. My bestie and I share custody. For my BFF, Tina is a cock sucking cuckold. For me, Tina is a sissy maid. Both of us use a lot of small dick humiliation and chastity training with her. Do not feel like you are more than just a sissy? Do not worry. The best sissy trainer will make you a sissy cuck.

Online Sissy Training and Partying with Margo

online sissy trainingI have a favorite sissy who calls me for online sissy training. Her name is Margo and she is fabulous. Like many sissies, she leads a double life. She has a day job and her staff see her one way. At night, when everyone is asleep and she can sneak away, she transforms into Margo. She is a partier. I find that it is much easier to become the best sissy you can be when you are altered. Drugs and booze free the mind. And when you free the mind, the rest will follow as the song goes. Margo calls me when she can sneak away, and we work on her sissy skills. She is a very obedient sissy who loves to please her sissy mom. She likes to smoke cigarettes too. I find that sexy. Seeing a pretty sissy with a cigarette in her hand blowing smoke rings on the cocks she is sucking is wicked hot. Margo not only looks the part of a sissy, she acts the part too. She loves to dress. She loves to party, and she loves cocks, especially those big black cocks. I think that is why she first called me. Because I am a BBC sissy trainer. I enjoy feeding big black cocks to newbie sissies and seasoned sissies like Margo. I mean if you are going to suck cock, why not suck the best cocks, right? I love all my sissies, even the ones I only talk to once, but Margo is the sissy of all sissies.

Sweet and Sassy Online Sissy Training

online sissy training

Online sissy training with a full blown cum loving brat is everything you think it is! I know how much you like being a girl and being put in restraints and giving you those bare bottom spankings you adore so! You have your sissy clitty tucked away in panties just like real girls wear. Aren’t you my pretty sissy?! I am not trying to break that beautiful spirit of yours just help you into your complete transformation. Lipstick lessons if you will, Training to fulfill you feminine longings. You report to me and we decide the best dildo for you pussy and what kind of cage will be proper for you to wear. You want to know my secret, I have the key to my own Sissy daddy’s clitty cage around my neck! I wear it as a badge of honor. You will be just like my daddy when you submit to your sissy mistress. No repeat after me, “I’m a little sissy slut and I submit my ass to you!” Your only goal in life is to please me.  You will have to undergo assignments and get that male spirit broken right out of you! You were born to be feminized and disciplined by your sweet and sassy brat sissy owner. I love when I make you take a selfie all dressed up and send it to me so I can critique you and tell you how to improve on that girlish appearance. Tell me about the crush you have on a man and what makes your clitty throb thinking about him. We will metamorphose you into the perfect happy sissy man. But be warned with any sissy assignments there are rewards and punishments. Dear Sissy slut, you know you will always need a side of domination phone sex to keep you in line!

Forced Sissy Training Is Just What You Need!

forced sissy training

You always tell me you want to dress up like a sissy slut and suck cock, but when push comes to shove, you always chicken out. I’m pretty fucking sick of that, so the next time you call me, it will be for forced sissy training. I don’t care if you disagree – you aren’t the boss. I am, and you know that. Stop trying to pretend like you wear the pants in this relationship. If I have it my way, and I will, you’ll never wear pants again. You’ll be in dresses, mini skirts, and slutty lingerie from now on.

In addition to that, you’re going to be on your knees with a big fat cock down your throat, too. And not just any cock. Since you’ve been stringing me along for so long, you’re gonna get started with a bang. I think you’d look pretty slutty with a giant black cock down your throat. I don’t care if you gag. I don’t care if it makes you vomit. Maybe you should have done what you told me you wanted to a long time ago and then you would have had a much easier experience. Call me now, sissy. I’m tired of waiting.

Sissy Training With Yours Truly

sissy training

Now that the dressing up part of your sissy training is complete, it’s time for you to learn one more really important thing – cock sucking. I know you’ve thought about it before, and maybe you’ve even pushed a dildo down your throat and sucked it. But that’s not the same thing as having someone else present. Someone who won’t go easy on you when you start to gag because you’re not used to having something pushed that far down your throat. I understand that you might be nervous, but sometimes you just have to throw caution to the wind and go for it.
You’re not going to get any sympathy from me, nor will you be babied by me. I’ll push your wannabe whore ass down onto your knees and tell you to open your mouth. If you don’t, I’m just gonna spank that little clitty of your until you beg me to stop. Trust me, choking on a cock is much better than getting your naughty area spanked. Are you ready to obey me and open your mouth so you can learn how to properly suck cock? If you don’t, it’s not going to be good for you, you nasty slut. So just open wide!

Sissy Training Mama To Help You Suck Cock

My proud moments as a Sissy training mama are when that Sissy gets her first feel of a real mans cock in her mouth. The throbbing head of a hard dick slipping between her pretty sissy lips. I’m always anxious to hear about that experience and love the excitement in your voice. My sissies always makes mama Diana happy. I’m a proud mommy knowing that you got to enjoy that experience for the first time. What beats sucking your first cock, is the joy of seeing, touching and tasting that first big black cock. Yes, I know the thrill, and I also know that many of you are still anticipating that experience. It will happen for you. But what is more amazing is to get your pussy penetrated and fucked by that first dick. The feel of your cherry getting popped while you are dressed all sweet and sexy. You put in so much effort dressing for cock and I am a proud mama that you finally got your anal virginity taken by a real man.

Sissy training

Call Upon Your Mistress For Forced Sissy Training

forced sissy training

So, I have this friend who was always talking about how he wanted to be feminized, but he never took any steps to do it. I got really sick and tired of hearing about it. He’d tell me he wanted nothing more in the world but wouldn’t take any of my suggestions. I did get him to dress up in lingerie one day and let me take pictures. I told him that once he saw himself all dressed up and sexy, he’d get more excited and want to move the sissification process along. But that’s not exactly what I had in mind.
Of course, he tried to back out of our plans, so I told him that if he didn’t go through with his feminization, I’d show everyone in his life the pictures of him in lingerie. I didn’t really WANT to blackmail him, but he gave me no choice. It took a few weeks to get things done, but once his forced sissy training was complete, he was very happy. And it wasn’t just the dressing up part that I helped him with – I taught him exactly what it means to become a sissy. Wanna hear more about that? Give me a call and maybe I’ll help you, too.

Forced Sissy Training Young Mistress!

Forced Sissy Training

Sometimes a sissy like her needs forced sissy training. She knows she was born to wear panties and bras. It is a deep craving that can only be quenched by dressing up like this. But sometimes this sissy slut needs to be put in a cock cage so that she doesn’t masturbate that clitty to sissy hypnosis videos. Then and only then will she become more aware to my hypnotic suggestions.

Now listen to me Sissy slave! Complete feminization must be the only thing on your mind! As your mistress I need you to focus on me and the way your body feels as I bring out the thoughts that have plagued your mind since puberty.  Don’t you understand that if your cock is less than 6 inches than you need to be fucked? Either with my strap-on or by the men who fuck me. Big black men who know I need a little help making that virgin ass gap wide. You are now dressed like a girl and deserve to be fucked like a girl!

Now you know what to do cum see me sissy fag! Your sissy phone sex Mistress awaits!