Category: Sissy maid 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

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 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 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?

Sissy Maid Training Sessions

sissy maid training

Hello to all of your feminized cutie pies! You have been calling me for sissy maid training for a while now and I think it’s time for you to go out and find your first job. It’ll be so much fun and I’ll help you through the process. I’ll go with you on your interviews and let the gentlemen know that you’re a first-class sissy maid. If one of them offers to hire you and he’s not the right fit for you, I will tell you to turn him down. We only want guys who are going to treat you like a lady while you clean and a whore at night.

I cannot wait to be there while you tell these potential employers about all of your night-time skills. Maybe you’ll even give them a sample of what you can do. I’ve taught you to be a perfect cock sucking sissy slut, so they will be in for a treat every single day if we pick them. I wonder if your cheeks will turn red when you’re telling them what you can do with your mouth and your sissy cunt? I guess we’ll find out soon enough, my dirty little girlie slut.

Nude Pantyhose and Heels Forced Feminization

My newest sissy slut came to me in Nude pantyhose and red leather heels. He wasn’t 100% ready to be a sissy but loved the Nude pantyhose and the look of the red leather heels with them. He needed the forced feminization from his new Mistress. I have known many men that enjoyed wearing sheer pantyhose.

They claimed it kept them warm under their man suits. I once had a lover that slept in nude pantyhose. He said they felt nice and warm. He shaved everything, had long gorgeous hair and was buff. He was a swimmer and also was on the wrestling team in school. These sports helped him into this role. 

So I was not very surprised that this man came to me wearing jeans, red heels and pantyhose. He wore a masculine button up shirt. The jeans and shirt were immediately removed. I dressed him in a nude bra with inserts, and a sexy black dress. I added on some red lipstick, rouge and did his eyes. Some clip on earrings and she was good to go.  

If you ever had a curiosity in being feminized I am the perfect woman to assist you. My sissy was reluctant in the feminization. I introduced a cock cage to keep her from fondling the very thing she needs to lose. I won’t have my sissy getting erections or cumming like a man. If you are restrained enough from ejaculating and getting erections you start to lose the testosterone. That is part of our training for now. 

Forced Feminization

Sissy Maid Training For a Cock Sucker

sissy maid training

Hey there, sissy slut. You’ve mastered being feminine, but now it’s time for your sissy maid training. I’m planning on starting a cleaning service and you’ll be one of my sissies that goes out to clean the houses of hot older men who love dominating weak little sluts like you.  We’re going to get you custom made maid outfits with short little skirts and of course, no panties. Well, maybe a little thong, but it has to be something that’s easy to slide over to the side. You know, for when our client wants to bend you over and fuck you.

Maybe he will fuck you while you do the dishes. I think that would be super fun! You’ll feel so used up and while you might think that’s a bad feeling, you’ll soon find out that it’ll make you feel fulfilled in ways that you never even thought possible. I bet you’ll be so excited that you’ll even cum and make a mess. And when it drips down onto the floor, you’ll get down there and clean it up with your tongue. But fair warning – when your ass is up in the air, you might find that cock back in it again!

New Years Eve Sissy Humiliation

Sissy Humiliation Training

I always wear out my little sissy sluts during the New Year. Everyone’s drinking and partying, so of course they’re extra fucking horny and could use a nasty little sissy slave to drain their balls or clean their cont after a crazy fuck session. The people of my kingdom really love a good time, and orgies are honestly one of our favorite pastimes. I know that sounds silly, but if you ever had four girls coming on to you, fighting over who was going to deep throat your cock? What about a group of sissy slut girls? I’ve got plenty of those, and they’re all very well trained at sucking cock.
I rent them out for parties you know? It doesn’t cost that much either, more or less just some videos of their humiliation. I love to watch the cruel things that my loyal subjects come up with for my pathetic sissy whores. Are you curious now as to what I let go on with my little pets? Sometimes they come back with lacerations and bruises, Sometimes they come back with full balls, and every once in a while they come back without their balls. When I say that you can do anything you want with them while you’re renting them, I mean that. That includes a forced castration. Now tell me, my sweet sissy girl, what are you doing for New Year’s Eve?

Sissy Phone Sex

Online Sissy Training During Lockdown

The interesting thing with this pandemic is, well that some have a lot more freedom and alone time to explore their kinks. Online Sissy Training has become more popular than ever. It’s safe and consensual. The ability to mail order things for these fantasies and needs is wonderful. The ability to dress up and have more time to train and explore is perfect. Now is the best time also. With the new round of restrictions and folks playing it safe during the Winter and Holidays means that the exploration of kinks is a great thing to do now. I am a trainer and an phone domination mistress. I want to help you realize that inner woman. I want you to understand that we can talk about all these needs and how they started. I will offer guidance and support for your needs and desires. I am very much committed to your transformation in real time or just in assisting with some kinky needs. The fact is, you do not need to hide or be shy with me. I am a mature and sensual dominant sissy mommy that wants you to achieve a new level of happiness. I want you to embrace the desire for young holes as a little girly girl. You may have the desire to dress for dick. You crave to see that coworkers big black cock and to be his bitch. I want to help you, Sissy.

Online Sissy Training

 

Breast or thigh?

taboo phone chat

Tonight was a great night for a taboo phone chat. Almost every call was about how the caller fucked a family member at Thanksgiving. My favorite call was about a family full of generational fornicators. This year was one of the aunts turn to be “eaten” for dinner. When everyone came to the table her legs were tied open and she had an apple in her mouth. Her arms were tied behind her and she was ready for some “stuffing.” The chairs were all set aside so that everyone could reach her easier. The all dove in for a piece, both her son and daughter each got a nipple and grandpa was cleaning out her cavity with his tongue. He husband was licking the timer that had “stuck out.” One of the other aunts had removed the apple from her mouth and was lowering her feast onto her face. They all heard her say “gobble gobble” as she made contact. It was a round robin as everyone tried a piece of her. Grandpa got to enjoy having his cock in her mouth last as he blew his load deep into her throat. Her husband enjoyed having a large cream pie all to himself for dessert. I think that I may need to re-think my own family traditions!