1,510 results for sissy training

New Young Sissy Toy To Train

The prettiest teen sissy slut stumbled onto my feet recently. I saw her walking down the street like a lost puppy. I told her that I like her pretty pink shoes and that only a good little slut wears shoes like that. I invited her to my place for a good sissy slut training. By the looks of her I could tell her sweet boy pussy was trained well. I made her undress down to her cute pussy pink  Sissy panties and only heels on. I asked her about her training history but it sounded like she only had been fucked before. I told her how I am a strict mistress and I better have any mess I have made cleaned up right away. I told her she came at the right time I had just had a really good fuck session that made my cunt dripping and full of hot gooey jizz. He got on his knees and licked my dirty cunt. With every dig of his tongue in my gooey pussy he pulled cum and juices into his mouth being a good slut cleaning me up.

Sissy slave training

When she was done I have her give my house a spring cleaning before I would fuck her with my strap on toy.

Sissy Humiliation At Its Finest

Sissy humiliation training

 

Who do you trust with your sissy humiliation training?  A newly minted mistress with one or two haggard old femi-men in her line up?  Some horny housewife with a score to settle with her cock loving little boy?  Give me a break.  Do you want to be a real sissy slut or not?  If so, you don’t fucking go to naive nipple twister or a put upon homebody…  Do you really think that June goddamned Cleaver can take you to the level of sissification that you crave?  If so, you’re as dumb as you fucking look, Jack.  Mistress K is the ONLY pretty little slave slut trainer around who knows how to properly degrade and debase a dirty dicked femboy faggot like you. 

How did your old dominatrix do it?  Dress you up in frilly little panties and make you prance around, maybe clean her house in a hot maid uniform?  Bitch, you don’t deserve those pretty panties and you damn sure haven’t even begun to work your way towards being a cock craving man-maid!  Who do you think you are?  You think that just because you call yourself a sissy it means that you can just skip all of the required training and jump right into being a hot boy whore with the tiniest little clitty around?  You really are a fucking dipshit and it seems to me that you need to be taught a lesson in respect.

Shut your fucking mouth and take off all of those horrible clothes.  You look like you shop at flea market bargain bins, is that a fucking “Esprit” shirt?  Was the Goodwill having a giveaway for dumb cunts, or something?  Don’t talk, just strip, fagboy!  Ever hear of a rhetorical fucking question?  You really are the dumbest sissy bitch around, aren’t you?

Ugh, I almost want to make you put your clothes back on, you look like a full on retard.  No, don’t pick them back up!  What’s you’re fucking problem, whore?!  I’m burning those rags, you just take a seat on the floor, pick up that magic marker and start writing on yourself.  I know you don’t know what to write, you’re a dumb fucking whore!  I’ll tell you what needs to be scribbled on your skin, moron, do you think I’m going to let you humiliate yourself?  Your parents must’ve hated having to raise such a pathetic piece of shit like you, I bet they’ve been disappointed in you since the day you were born.  Do you think you can even spell correctly?  I’m not here to fucking teach you how to spell words, but if anything I tell you to write is misspelled or written backwards, I’m really going to let you have it, bitchface.  You better get it right or this is going to be a long and painful process for a stupid slut slave such as yourself.  Now pick up the fucking marker!  Why did I have to tell you twice, cunt?!

I’ll start off easy for you since I’m sure you’re going to fuck this up.  Draw a few concentric circles… what do you mean “What’s concentric?”  Oh.  My.  God.  I have to teach you the fucking meaning of words?!  Like a dartboard, moron, you’re making a cum target on your belly button.  When you’re done with the circles, label it real big on top so everyone knows where to blow their load.  Oh, fuck me!  Did you really just write out a backwards “G” just after I told you to be sure to spell that shit right?  That’s it, I’m getting my cattle prod.  You’re going to listen to me, whore boy, one way or another.

 

Femboy Training of a Bad Boy

I have a good friend that has married a complete loser, and I finally got my chance to blackmail him. I took to some Femdom training of this little dick man with an porn addiction. My friend is a little bit old fashioned and pretty tame in her sexual explorations. Her man is not very endowed and is a bit of a bitch.

The other day my friend was going away for a week and asked if I would check in on her husband. The afternoon I stopped by their place to check in and acted like I just needed to borrow something of Cynthia’s and I wouldn’t be long. He was obviously in the middle of something naughty. It did not take long for me to see that he was watching fag porn and was wearing panties and a bra.

Femboy training

I cornered him and asked him about the porn on his laptop. He tried denying and fidgeted a lot. I told him to drop his pants and take off his shirt. Now. He fumbled it all off and sure enough. I snapped a picture and told him I would be returning later for a little training of my new Bitch. I explained these pictures would go to his wife / my best friend if he did not do as I say from here on out.

 

Mistress K’s Sissy Maids

Sissy maid training

 

I like sissy maid training because it’s just fucking fun!  I get to dress up a bunch of femboy freaks and make them prettier than they’ve ever been in their entire lives and get paid to do it!  What do you do for a living, drive a big dumb truck across the country 8 million hours a week or push stacks of paper, ad nauseam, back and forth on a desk for a thankless company?  Fuck that!  You can keep your normie career and your, no doubt, mundane life.  My sissy maids keep my life really fucking interesting and my apartment clean as hell!

Every pussy coveting parlourmaid of mine has to adhere to Mistress K’s strict standards and they’re happy to do it.  They put on every hot little uniform and tight and tiny clitty clamps I tell them that they need and they’re better sissies for it.  They clean every nook and cranny I command them to with any size dildo jammed way up in their asses that I deem appropriate for the job with a big smile on their faces.  They always take every single schlong that I throw at them and even make sure they clean up every drop of cum that might get away from them when it explodes out of those dicks and shoots all over them.  My favorite is when they thank me for the opportunity to fuck a fat cock while they lick and slurp gelatinous globs of jizz off of the floor.

You might like your job and you might even have a maid.  But does Consuelo let you strip her down, abuse her naked body then doll her back up in a hot french maid uniform?  Does she stuff her holes full as she cleans your toilet with her mouth?  Does her little clitty go drip-drip-drip when you tell her you’re going to make sure her asshole is gaped out big and wide before her shift is through?  Does Consuelo pay you for the opportunity to clean your place while you degrade her?  No?  Sucks to be you, Bro.

 

Let’s Get High and Have Sissy Phone Sex

sissy phone sexWant to get high and have sissy phone sex? I love to smoke weed. I appreciate my callers who like to party with whatever drug of choice they prefer. I have all kinds of druggy sissies. Some like coke, some like crack, some like meth, some like weed, and some like poppers. They all like cock though. I find for cock sucking sissies a little hit of whatever magic potion they prefer will get them ready to suck a ton of cock. I love oral training my sissies. During Covid, I would have sissies come over. I would tell them to bring their party supplies and all their pretty clothes. I would bring the cock. We would get high together and I we would show off my skills dressing them. I used to do hair and make up professionally. The skills never leave you. I can make a pig prom ready. Sissy Sally came over last night. She has been with me for almost a decade. A few bumps of coke and you would never guess she still needs sissy training. Now that Covid is in the rearview mirror, glory holes are open again. I no longer need to invite studs over to blow bang my sissies. I can dress them up and do their hair and makeup and take them to the glory holes. Sissy Sally sucked over 50 cocks in three hours at the glory hole last night. It was hopping too. I let her do bumps off my ass. She is a great cock sucker, but she used to be dreadful at it. She would use her teeth, gag when just the tip was in and spit out the cum. None of those bad habits were continuing when I was her sissy trainer. Now, ten years later, most guys on the other side of the glory hole wall think she is woman like me. That is because she has the best sissy trainer. I get her high, so she is more loosey goosey with those cocks. And I teach her how to look and act the part of a cock sucking sissy. Bring your poison, and I will bring the cocks.

Sissy phone sessions

sissy phone

Get ready for some wild sissy phone fun. I’m going to use terms that will be hypnotic. You will be my sissy slut who will do whatever I say. Once you do what you want, you will move on to the next level. Sissy tasks tend to be all about what makes your mistress happy. What makes me happy is a fluffer and a vacuum cleaner. Go ahead and suck a cock till it’s hard, and clean up the effect. Take notes and learn what will make you the best sissy slut.

It is an honor for you to learn the best tricks and tips for becoming the best cock sucker and the number deepthroater. you are so lucky to enjoy training from the best red headed goddess around.

Breaking In New Pretty Little Sissy Bitch

I have a new pretty little sissy bitch since my perfect sissy has strayed and I wanted to show my new one how to be.

Sissy slave training

I bought the biggest two-sided dildo I could find. I bought some new sissy panties and bralette set with matching stockings. When my sissy walked in, she got naked right away I love watching her little clitty in between her legs excited to see me. I turned her around and spanked her ass and made her tell me who she belongs to. She got dressed in 6-inch heels and crawled to me. I spread my legs so my sissy slut could lick my cunt and get it wet for the strap on dildo I had for us. She did as she was asked and when I put it on, she was bent over spread open showing me that man pussy. As I pushed my strap-on deep in my new pretty little sissy the other side went deeper in my cunt. I started fucking her hard and deep making sure I used her so I can cum hard. I didn’t stop until I felt my body tense up, I started cumming hard. I pulled out of her now gappy man pussy and told her to stay that way until I was ready for more.  

Best Sissy Trainer

Best sissy trainerLet’s go shopping! I’ve turned Sissy cooper into the perfect slut. No matter what he will never be a woman so he will always come back crawling to me. He knows fairly well who his superior is! He aspires to be a woman much like myself, one with sass and a nice round ass. The kind of lady that turns every man’s head! Cock drawn to her without a mention. He’s learning how to suck cock like the perfect princess fuck slut that he is. We have been practicing his nice feminine moan. No man wants you grunting while giving him a blowjob. You are going to have to learn to squeal and let out musical moans to raise the hair on his body. What better way to learn than by the best sissy trainer out there. You can check my resume! Come find out for yourself. I don’t want an average Jane. I want an extravagant bitch who knows that a woman requires daily grooming. A dramatic style with one that stands out in every room. There is no competition!! We see no competition!! When I am through with her. She will have all the other sissies wishing they could be her. Manicures, pedicures and waxes from head to toe. Lace fronts and Jewels. Nobody said becoming a woman would be easy but for certain it isn’t impossible. Sissy Cooper will be one of a kind when we are through with sissy training!

Maid Training Mistress

sissy maid training

You probably already know this, but one of the things I love most is when I get to do sissy maid training with a new caller. Now, don’t get me wrong. I love all of my longtime sissy maids. But everyone loves the feeling of something new and I’m no different. Helping a new sissy maid pick out a cute uniform, sexy heels, hair, makeup… that’s just one of the most fun things to do. I love the excitement that brand new sissies have. And so many just love taking care people, so being a maid works very well for them.

Do you want to go with the classic French maid uniform? Or would you like to try some different looks to see what looks best for you? You definitely need the cute little feather duster so you can just prance around in your heels like a dainty little lady. But we all know that you’re going to be used like a nasty slut. You might try to play it off like you don’t like it, but we all know that you do. I hope you’re ready for the very best sissy maid training around!

 

Sissy hypno and lessons

best sissy trainerHypno for Sissy Tj is all too much fun for me. Casting my special spell to sissy all over the world.
The best sissy trainer is a control freak. And as a sissy hypnotist I’m all about that control over my sissy subjects. Now sissy Tj is a bit of a BDSM freak with her spanking skirts and bondage gear ready for her to be disciplined. This sissy loves to be paddled and locked in chastity with the key thrown away! A very special encounter had Miss Tj buying an expandable butt plug for us to continue our lessons. Trust me I have this sissies clothing and toy inventory and i will dress sissy Tj up and have lessons of humiliation, public and self. And just some basic sexy things I need my controlled chastised and slutty sissy whore to do for me! Would you like to be added to the corral of sissy whores like my sexy and slutty Tj during Femboy training?