Tag: Sissy maid training

Welcome to Online Sissy Training

online sissy trainingWhen you specialize in online sissy training, you get to talk to folks from all over the world and all walks of life. I have a new sissy in my ever growing posses of sissies, cucks and faggots. This sissy is unique in many ways. First, she is from West Virginia. Not a state any of us get many calls from. A sissy thrives in a metropolitan area. At least out sissies do. Why? If you are under my tutelage as a sissy, there are things you need to do. Steps to becoming a sissy. For example, one of my favorite tasks is to send a sissy to Victoria Secret’s to try on bra and panty sets. I demand my sissies be honest that the purchase is for them. In smaller rural areas, this is not as easy because lots of folks know each other and the sales ladies do not get men buying lingerie for themselves often. A guy will stand out. Another task I am fond of is sending sissies to glory holes to learn some cock sucking skills. Small towns either do not have a glory hole or a fruit loop, or it is just too risky to go to one. As a sissy trainer, I care about my sissies. I do not want any of them harmed for being who they are. This new sissy was different also in that she has a military background and is masculine on the outside. A lot of sissies, most sissies, have small dicks and not much testosterone. My newest sissy has a 7-inch dick and is in shape too. No worries though. I will stick a big dick or a sissy clit in sissy panties all the same. This sissy also has some self-discipline. She has long been caged to prevent her from jacking off too much. My guess is her military background has helped her be disciplined. I love my job. I love training sissies from the ones with no clue yet that they are sissies to the ones already dedicated to being the best sissy they can be. Sissy school is open no matter where you fall on the spectrum.

sissy panties

Sissy the liar

sissy maid training

I went to a sissy auction the other day and bought a few to help in the household. I have been in need for a good maid and I bought one that said she was already trained. I discovered her lie after I allowed her to clean my office. She was wearing way too many clothes, she couldn’t dust at all and she looked at the vacuum like it was going to bite her. I pulled her over my knee and beat her ass black and blue for lying. The next morning when she got up there was a maid uniform and some pretty panties waiting. She came in the office and was embarrassed and holding her hands in front of her tiny clitty and balls. I had her come over to me behind my desk where I had her new cock cage waiting.  I played with that small cock for a minute until she got hard and I then snapped her in. She whined about being turned on and that I should help her. She got another round of spanking for that one. I then took her by the hand and showed her how to dust, wipe clean and then how to use the vacuum. I watched for a bit as her pretty ass swayed in front of me as she vacuumed and decided that I wanted some fun. I grabbed one of the dildos that I keep in my desk for this type of occasion and went over and turned off the vacuum. She turned to face me and I told her that I was going to have some fun now with her body. She saw the dildo and her eyes widened in terror. I told her to bend over and grab her ankles because this was going into her ass for the rest of the time that she was cleaning. She had tears dripping from her eyes as I lubed that dildo up and placed it in her ass. I told her that if she dropped it that she would be cleaning the floors with her tongue.  

Sissy Maid Training Expert

sissy maid training

I’ve been thinking of starting up a business doing sissy maid training, but then I realized I don’t need to do that when I can train sissies over the phone. I’ve been doing it for a while, so I don’t see a need to change things when they’re already working. Have you thought about becoming a sissy maid? Just think of all the rich, horny old men you would get to work for and probably get fucked by. You know those old, conservative rich men are horny and will fuck anything that even resembles a pussy.  So I think it’s safe to say you’ll get your cunt reamed pretty hard.

If you do a really good job and do special sex tricks for him, he might even pay you a little extra. If you suck his cock and tongue his asshole the way his wife won’t, you’ll likely get a bonus. If you tell him it’s okay for him to invite over his poker buddies and let them use you during breaks in their game, I bet you will score big time. All you have to do is call me for some sissy training and you’ll have your pussy full in no time!

Sissy Maid Training My Own Brother

sissy maid trainingMy brother deserved sissy maid training after he refused to clean up after himself today. He left all his stinky workout gear all over the bathroom, his towel on the floor and he knocked my new make-up pallet on the floor. Now I might be younger than him but when I told him to pick his mess up he told me to make him! I have some girl strength and I told him I would,  and jumped on his back and pulled his hair. We struggled until we hit my bed and I managed to pin him down!

“Now we can do this the hard way or the easy way you choose,” I was grinning down at his shocked face. He said easy, which was the wrong answer! I leaned over and grabbed my make-up box and my tweezers, as he struggled I began working on his pretty boy face. I made sure to reach down and pinch dick dick under the towel around his waist; he would be mine now. I would have full control and he would be my new maid. I showed that beautiful doll like face to him in my Jeffree star mirror! There was a change in his face as he began softening and letting me wax him from head to toe.

I would have a sissy maid slave who did everything his sister wanted from now on. I even helped him into his first pair of sissy panties, soon he would be in sissy dresses and being taught exactly how I liked things to be!  Sometimes just seeing how pretty you are in the mirror for me and yourself is enough to transform you.

Princess Zoey, Your Phone Dominatrix

Phone dominatrix Princess Zoey is thrilled to be your bratty sissy owner! But that doesn’t stop me from being a phone dominatrix when you really need some one on one time with me. My clit gets hard and big , just like your clitty, when you have to spank yourself for me. Your Mistress had you call me because she knows you need to be in complete submission even when she isn’t looking over your shoulder. That email I got today? She said she caught you wearing her lingerie and stroking your clitty through it! You didn’t even have a panty liner on to keep it clean from your boi juices.  Oh, you are so naughty! Then you are going around acting like a spoiled brat because she took away your boy clothes and is going to make you go out in public in your sissy dress. Yes, Mistresses often rely on  PRINCESS online sissy training to keep bad boi sissy sluts in line. I own my daddy and I know just what to do to get you in line! I know you are locked up tight sitting in a hard back chair rubbing your caged clitty all over the back as we have our session. Most sissy slaves are honest to a fault. I make you stop and go get the fly swatter. Twenty smacks to your cliity cage! I demand you to stop sniffling and bend over the chair and give yourself twenty more fly swatter smacks on each sissy boi ass cheek. I love hearing you disciplined at my command! Then I tell you that I want a gift card code or else I will email your personal mistress and you will be punished so much more. Either way my cunt will be satisfied, your pain or something new and shiny for me! online sissy training

Frocked and locked

forced sissy training

Directly disobeying me will result in forced sissy training every single time! When I told Sissy Sam to go to work wearing panties under his suit everyday I meant it! Random inspections will be done, not that I told him first. But I needed to see, and when I got to his office he sputtered and tried to be angry. But I would not expose him if he let me see his undergarments for the day. Just as I suspected, cotton men’s briefs.  That required an allowance increase for me! Shame sissy shame, Pay piggy! I pulled a jeweled butt plug out and told him to bend over and gave very little lube and pushed it inside his little ass. It was tight and now he had to wear it all day! I bet his employees thought he was constipated. I giggled as he came over for a session. I had promised that he just might let him fondle my perky breast and play with my pussy. But instead there was a billowy pink sissy uniform and a brand spanking new cock cage. I had a list of chores for sexy sissy Sam once he was dressed. So pretty in his new cage and butt plug don’t you think? First we painted my toenails and gave me a leg rub, on his knees of course! And next we watched some sissy porn so I could watch that cage get tighter on his clitty. Oh how it swelled and leaked! But I still had some sissy maid chores, like scrubbing the floor with that ass in the air, so he could get used to exposing that tight sissy ass! My sissy would obey me, and at the same time learn the basic steps to become fucked and go through forced feminization until he metamorphosed into a full flagged sissy whore! 

forced feminization

Sissy Maid Training For Cock Cravers

Sissy Maid Training

I’m Diana, a Sissy mommy and Mistress. Sissy maid training sessions are great for those closet cock craving, panty wearing girly boys. I think you could use some fun in your dress-up time and be made to do naughty things for the love of cock. I have a sissy son of my own and we can all play together even. If you are a good cock lover I will let you suck my boyfriends big black cock. Oh! That made your clitstick twitch didn’t it? The thought of your mommy feeding her boyfriends BBC into your mouth and having you suck it off. It was just in mommy’s vagina. You like the taste of mommy’s cunt juices on that cock don’t you? You got so excited watching mommy bent over in the laundry room as I was getting all my sexy panties and bras from the drier. You knew there was cum dripping between my legs and soiling the sexy panties I was wearing. You were so good to put on a pair of panties and lay down on mommy’s bed and wait for her. I always love the way my Sissy cleans my messy creampied cunt up. You deserve a big cock of your own to suck baby girl.

 

Sissy girl training with Miss Remi!

sissy girl training

Come on ladies!  Sissy girl training starts right now! I hope you’re ready for Miss Remi to turn you into the princess cum slut that we all know you are! It’s what I’m best at, after all. I might be young but I’ve been training little sluts like you for a long time! My mama taught me to be the best trainer there is so that I could turn out the hottest he-whores ever and make good money off of those tight whore holes! Don’t try to resist because that only makes me more eager to put you on the street, selling your slutty little pussy! Everyone knows my sissy whores when they see them! Miss Remi makes all of her sissies wear the hottest and sluttiest outfits. I need you to impress all of these hard cocks I’m going to bring to fuck you. My sissy sluts know how to gag on a cock and give the sloppiest and nastiest blowjobs ever! What my sluts are really known for though, is their perfect tight sissy cunnies and how well they can take a huge hard bull cock! I let my sluts get pounded in their hot little pussy holes and make them take so many loads of cum! Once you start sissy whore training with Miss Remi, you’re going to become the ultimate cum dumpster sissy slut!

 

 

Sissy Girl Training For A Sissy Whore

sissy girl Training

My sissy Nadia has made the transition to a complete cock whore.  She obeys my every command during our sissy girl training. Sending me pictures of her in her complete getup. Looking fly for a white girl I might add.  I know she is dependent on our talks because she can’t even get her clitty to squirt without me knowing how much she loves the black cock. I know she cums on those black cocks, but her submission is cute. She says she needs to tell me the dirty slut things she does to get a black man to fuck her and knowing I know makes it that much easier for Nadia to squirt when she is being pounded! She comes to me for advice on close and cock sucking. Even though I know she is a pro at what she does. I think it is part humiliation and knowing that I have a sissy boyfriend and daddy that help her with her sissy chores and sissy maid training in real life! I wish all sissy sluts were like my Nadia Truth be told. BBC loving whores always have to stick together!

Giving Daddy Sissy Maid Training

sissy maid training

Daddy Jim gets a special kind of sissy aid training from me. See he has to do as I say and put on his cute little maid outfit and hold his pee until I say he can. I make him wash the dishes with the water running full blast as he does his little pee-pee dance. Then I make him Piss on the clean dishes so he can wash them all over again! I am so mean right. Well I do take it easy on his little two-inch clitty and give him a big monster BBC to suck on like a lolly. He loves that shit; he will suck and gag until he has to pee again. I put him in his pretty little cock cage and make him piss with it on this time. I poke at his balls and little tiny dick until he can give me a little cum shot and then it is back to work for that sissy cum dump! All the while I am being fucked wherever he is cleaning by the big black bull cock! Bet you were wishing you were Daddy Jim now!