1,510 results for sissy 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

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.

Cocksucking Sissy Phone Sex Training

sissy phone sexI love being a sissy phone sex mommy. It has been a super busy week for sissies too. New year, I guess, is making sissies want to get more cock. I cannot blame you. Glory holes are opening back up. Men are back on Grinder and wanting a sissy bitch to suck their cocks again. You just need some sissy cock sucking training. I want to help you with that. I turned my twin sissy boys into cock sucking faggots and I can do the same for you. I am a big dick sucker, so I know how to help sissy boys swallow big dicks too. A few things you want to have on hand are olive oil, popsicles and a big dildo. Olive oil helps coat your throat to make it easier for big dicks to slide on down. You do not swallow the olive oil. You swish it around in your throat and spit it out. Popsicles can be used beforehand to numb your throat or afterwards because if you are new to sucking big dick, you will be sore. Now the big dildo is for practice. You want to practice your cock swallowing skills. You want to know how far you can go before you hit your gag reflex. Guys with big dicks may force you down on their throbbing shafts. You do not want to puke on their dicks. My sissy boys can swallow up to 9-inches of thick cock without gagging or puking, but a couple years ago they gagged on an inch of cock meat in their young mouths. Thanks to mommy’s cock sucking sissy training, my sissy boys can deep throat big dicks just like their mommy. If I can make two young boys cock sucking faggots, just imagine what I can do for you.

Sissy girl training with Remi

sissy girl training

My best friend called me this morning with good news. She had found her little brother’s diary and read it. She told me how he had written all about wanting to be dressed up and taken around town. He wanted to be shown off like a dirty cum slut. She knows that sissy girl training is my specialty and thought that maybe we could have some fun with him. We invited him over. I told him that I knew his secret and that if he didn’t show up, everyone he knows would get a copy of his sissy slut diary by tomorrow. He came right over and was ready for his training. I put him in the shortest, sluttiest dress with tall heels and sexy thigh high fishnet stockings. We turned him into such a hot little cock whore. We went out for drinks and I made sure to show my newest slut off to all of the horny old men in the bar. I lifted her skirt and showed off that pretty little he-pussy through her silky panties. That thirsty little whore was so eager to get her hands on a big, hard dick. Everyone could see a little wet spot in those panties. We hadn’t even finished our drinks before I was getting offers on that sweet, virgin pussy hole! I made her into the sissy whore she wanted to be and I made some easy cash selling that cum slut.

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!

Sissy girl training for the holidays

I had so much fun this morning! I woke up bright and early to open gifts with my sissy sluts. Before we could open anything and have any fun, they had to do their lessons for the day. Sissy girl training doesn’t take a break, just because it’s Christmas! I dressed the three of them up in the cutest, silky red panties and bras. I had them prance around and show me how pretty they looked in those sexy slut panties. I made them line up in front of the tree and get on their knees as I let my big bull stud friend in. He was dressed like Santa for the special occasion and had a nice big, fat candy cane for my sissy sluts to suck on! I helped guide his big cock into their little mouths. They sucked him and teased his fat dick until he was about to explode. I grabbed his massive fuck rod and stroked him while he shot hot cum all over my tits for my little whores to lick up. We had so much fun that I almost forgot about the naughty gifts they had waiting under the tree…

Do you think you can stand some more Sissy humiliation training from me?

sissy humilition trainingDo you think you can stand some more  Sissy humiliation training from me? You must be a gimp. All while you sit back with your panties and itty bitty cock in hand. Are you a sissy who likes to play dress up?Are you the type of wannabe who has accepted that your clit is so small and measly that it should be called a clit!     Do you have a clit instead of a dick? It could be, but I can’t see it from there, or with your pants in the way, or this big fat cock in my mouth. Just a wimpy humiliation sissy who needs to be put in her place while I get my ass and pussy fucked RIGHT in front of you. Sissies aren’t looking to please women sexually. sissy panties They can only please their mistress by entertaining her. Laughing and laughing at you – it’s something I could do over and over again.         A two inch nub gets lost in boxers or boxer briefs. You need sissy panties! I don’t care how much you spoil me. I don’t care how much money you make. With a clit stick, it is not possible to fuck me! Don’t fool yourself. Size matters. I will, however, clit tease you. This silky smooth pussy is going to make you think you might actually get to feel it wrapped around your shrinky dink dick.    Despite the fact you know you aren’t worthy of me, you still spend your money on me with gifts and tributes. If I’m going to be subjected to losers with small clitt sticks and dicks, I need to be adequately compensated.    Even if they just give me laughter, every loser has something to give me.

Giving Seduction and Sissy Hypno Training

sissy hypno training All Things considered a little sissy hypno training is just a blip in your world, but you might need just a little push to be what you are. Sexual sensual domination and my voice in your ear encouraging your innermost desires. You do not have to live a life denying who you are. You do not deserve to be a man with a small dick who hates himself. The sissy life is where you belong so you can embrace all that you are. Your small dick is now your clit and your ass is your beautiful pussy. Tight, wet with your cummies and waiting for a nice big cock. Let me seduce you to go to that black cock glory hole and slurping cock for the first time. My sexy body is adorned with the feeldoe strap. That has an 8 inch dick that makes me vibrate inside and strokes my g spot and fucks you at the same time. Flip up that skirt and take me and my big back boyfriend. I am in an open relationship with my own sissy cuck boyfriend and he has room for another sissy with us. My dear you will be under my spell in no time! Give me your squirties and lick your hands clean, that is your first taste of cum, you will be begging for more by the time I am done with you!

Sissy Hypno Training For Cock Sucking

Sometimes you haven’t quite come to the realization of what you actually are. You have thoughts and get confused. It’s ok to think about dressing in lingerie and think about sucking BBC. I offer sissy hypno training to help you realize your inner desires to be a sissy. You probably already wear the panties or pantyhose. You like how the feeling of having smooth hairless legs, arm, and balls. You like to be smooth and feel silky things rubbing against you. You enjoy it so much your cock throbs and starts to leak. After so much watching those bull cocks fuck mommy and see how shimmery they are you crave to suck on them. You want to taste mommy and experience what mommy was experiencing. After a bit of fantasizing the need to have your ass penetrated grows and you start wearing panties and bouncing of objects inserted in your sissy pussy. It’s due time you buy a dildo and a butt plug. You make those purchases and give me a call to start our training sessions.

Sissy hypno training

Sissy slave training the new slut

 

sissy slave trainingI invited my new play-thing to Thanksgiving with my family. He knows that I have an unusual family but what he doesn’t know is that I come from a very long line of sissy slave training mistresses! I’ve been wanting to bring him home and transform him into my very own cock worshiping, sissy slut, since the day I met him! My mom finally agreed to help me turn him into one. My mom and sisters are ready and waiting, with his new wardrobe of slutty skirts and tiny tops. Plenty of lacey and silky panties to choose from! As soon as we have him dressed like a proper slut, he’s going to learn the art of throating a fat, hard cock and choking down gobs of cum! We may have to spend a few extra days in training, depending on how quickly he perfects his cock sucking skills. Next, comes breaking in that beautiful he-pussy. I’m saving his sweet sissy hole for a special cock… or the one that pays me the most for it!