Category: Sissy humiliation training

The Beginning Of My Boss’s Transformation

Best Sissy TrainerI work in one of those standard boring offices with a nine to five gig. It fits me most of the time, however lately my boss has been a major buzz kill. He’s starting to complain the clothes I wear are no office appropriate. He went as far as to tell me that my skirts are to distracting for the males in the work place. I’m use to sexism but nothing has really changes until this last week, and I’ve been racking my mind as to why. And a thought occurred to me, last week in the break room I spilled some coffee on my blouse and since I was the only on in there I went ahead and did a quick change. But if that perv was watching the camera then he may have seen me in my pink bra looking through my bag for another top. However, it doesn’t explain his recently attitude toward the way I dress…unless he was jealous. I easily pick up on those kinds of things. So I tested my theory and waited for most of the office to clear out before requesting a meeting with him. I shut his door and pulled the blinds down while he gave me a puzzled look, and then I threw a pair of lace pick panties on to his desk. “Put them on”. He blushed and cleared his throat. “Excuse me?” he attempted to question me. I laughed at his attempted to cover up what I already knew. “I said get you sissy boy ass up and put on the panties, I was very careful to get a pair I was sure would fit you”. The room fell silent and for a minute I thought maybe I was wrong. Then he picked up the panties and started to feel them in his hands and smiled. “How did you know?” he asked. “Because all sissy sluts act jealous around me. I’m everything you want to be, and if you do exactly as instructed I can get you as close as possible to being just like me.”. The happy look in his eyes told me exactly all I needed to know. Now the fun part can begin.

Comply Or Perish

mistress phone sex

No matter how many disobedient boys I talk to there always seems to be another one in need of correction. It’s a good thing that there are lots of Dommes that are ready to take the whip to them and correct their behavior. I can only imagine the perverse things that you’ve done that you need to confess. Confession is good for the soul. Come to me and kneel and tell me what you’ve done. I’ll go from there in deciding how to deal with your actions. I’m not a kind Mistress either, I will bring you a great deal of pain.
If you’re sitting there stroking your hard cock and thinking of Mistress phone sex take your goddamn hand off of it right now. That is not for you to touch without permission. Boy, you are going to be a lot of work aren’t you? That’s OK, I am a strong Mistress and I’ll make you crumble at my feet in worship. It’s actually your good luck that you found me. I’ll bleed the bad right out of you and baptize you in blood only to have you reborn as my servant. Your body, mind and soul will be mine.

When you Disobey you get Forced Sissy Training

Forced Sissy TrainingSometimes I have a little sissy come to me that requires forced sissy training. One sissy could not keep her hands off her little clitty. She was constantly sneaking around and hiding to watch shemale porn and searching the web to view the BBC. The only thing she wanted was cock, nothing else. She was my little clean up gal because she was such a cum whore until she started disobeying. She knew she needed to ask permission to play with her clitty, watch shemale porn or look at BBC images. So, what to do with a little sissy who is obsessed with cock? I could cage her little clit, butt plug her man pussy, turn off the internet or bind her hands, but that would be too easy. I was feeling a little more punishment was due. I brought her into the back bedroom and had her undress and put on a pretty pair of black heels. I attached a blindfold to her face and handcuffed her hands together. Next, I had her lay back on the bed, and I attached a spreader bar to her ankles. Her dick was so hard, but I lifted her blindfold and gave her a little blue pill to take. We want to keep that dick nice and hard. She was almost panting in the excitement as she thought I was going to use her to get some dicks nice and hard for Mistress Francis. But she was in for a shock when me and all my girlfriends came into the room for some drinks and fun. What this little sissy wants least in this world is pussy. For her punishment she was going to have to fuck pussy for as long and as many times as my friends wanted her too and with that little blue pill, we could keep this going all night.

My Sissy Gets Some Humiliation Fun

sissy humiliation trainingOh how my sweet Devina went on for weeks begging for a humiliation assignment. However I wasn’t quite sure Devina was ready to push her boundaries. Then I realized I didn’t actually care so I sent her specific instructions with a warning that if she did not follow through I would disown her from my collections of sissy darlings. She was to meet me at my favorite nail salon at 2pm on Saturday. I knew they would be the busiest than, which made it the prime spot to show off my pretty pet. I should mention instructions entailed her showing up in a dress and pretty pair of floral sandals I recently ordered her to purchase. Much to my surprise my little sissy bitch showed up! A complete stuttering mess and a bit clumsy as she shyly looked at everyone who was whispering and giggling. Never seen Devina this shade of red before, she certainly impressed me. We each got our nails done with bubblegum pink polish and for good behavior I let her out of her little pink clitty cage for the evening. I have a pretty good idea of what she did for her Saturday night.

Sissy girl training

sissy girl training

Sissy girl training is my passion. I would love to strip you down, and redress you  like my little sissy slut fairy bitch. Bring your tiny little cockette over here so that I can look at it. I want to laugh as I put you in panties. You’ll wear them because that tiny excuse for a peepee is more of a clit and that’s what you will call it. I want you to rub your clittie for me through those silky panties and tell me how much you want me to fuck your sweet little pussy hole. I bend you over and spank your thick little ass until it’s red and stinging. I pull your cheeks apart and slide my big thick, studded cock right into your whore hole. You love the feel of my strap on. I’m going to hold you down and fuck your little fairy ass like the cum slut you are. You’re going to be my little fairy hoe and I will own you! I pull my cock out and make you suck it clean. I love watching you lick all of your he-pussy juices off of my strap on cock. You’re my sissy girl and I will fuck you when ever I want!

 

BBC Sissy Trainer

BBC Sissy Trainer

One of my favorite things in the world is being a BBC sissy trainer. Turning sissy sluts into big black cock whores is one of the most fun things ever. You sissies already have your look down (and you look fabulous) but now you need someone to teach you exactly how to please those giant chocolate fuck toys you’ve been drooling about for so long. It won’t take me too long and I’ll have you trained and ready to take a BBC in either one of your holes anytime and anywhere. You’ll be able to just drop to your knees or bend over and be able to handle it with absolutely no problems.
How does all that sound to you? Are you finally ready to let me train you and make you the best big black cock sucking sissy faggot in the county? I’ll teach you all my tips and trick and you’ll be such a whore that everybody is gonna know your name. They’re also gonna want to get in on the action. What are you waiting for? Call me so I can teach you everything you could ever want or need to know when it comes to sucking black dick.

Mistress phone sex

Mistress phone sex“I want the world to know what a sissy I am Mistress.” I look down on him with adoring eyes. “Is that so?” I start to pet his head. “You need the world to know what you truly are. Trust me I know.” “You are not the first sissy to come to me with a confession like this.” And I know exactly how to handle your craving of being ‘The center of it all whore.’ I walk across the room in my thigh high stockings and four-inch black high heels. Twisting around I face you. With my finger, I call you over to me. You crawl over on all fours as good sissies will do. You kneel before me leaning down and kissing my heals. I point to the right of you and see that I have you on live internet feed in your girly pink lacy dress. “Tell the world your name.” He spurts out “um, um… my name is Tim Mistress.” “Very good I praise you with.” “Now tell the world where you are from.” ” He looks at the camera and again spurts out “Texas Mistress.” His face blushes his dick rock hard his dream comes true.

Sissy phone sex

sissy phone sex

Sissy phone sex is my most favorite thing to do. I love training my sissy girls over the phone and making them rub their little clitties for me. Making sure they’re wearing their pink frilly panties as they make sticky messes for me. When I have them all to myself, I make them dress up for me like the little sissy girls they are. Then I put them on their knees and bring in something they’re not used to seeing. I bring in a real man with a real cock. I make sure they take his huge thick cock deep in their little throats as I turn them into the perfect little cock sucking cum queens! I make sure they gag on him and deep throat him like good little bitches. I love getting fucked right in front of them and making them lick me clean after! Part of making them cum eating queens is making sure they can lick out every drop! My little sissy dolls are the perfect cum sluts.

 

Brandie’s Valentine Present

Sissy PantiesSo, as a special treat for my sissy slut Brandie I ordered the best Valentine’s Day present. She has been so naughty lately. Unable to keep her hands off her little cunnie even though she has been reminded time and time again that it does not belong to her and she can not play with it without asking. We have paddled that little clitty and taken away her shemanle porn. Nothing has seemed to work. Her last act of defiance was when she left all her little cummies and refused to clean them up. So, I ordered a cute little pink cock cage for her cunnie. I also got a pretty pair of panties and a little dog tag to attach to the cage that says sissy slut. I got it all together and wrapped it so cute and asked Brandie to come down and open it. She pulled the panties out first and was so happy, she loved the dog tag and the matching bracelet too. But the cock cage did not excite her very much. I made her come over and I put her little clitty tightly in the cage and locked it up. She looked adorable in it. Next, we put on the panties and she looked even cuter. I didn’t want to keep this cuteness all to myself, so we had some friends over and had Brandie model her new gear. We all laughed and laughed at her cock cage. We then had her stand and watch as we sucked on some BBC and didn’t even let her clean them up. The cock cage kept her clitty from getting hard and I could tell she was uncomfortable. And just to make her more uncomfortable I had her watch while I took BBC after BBC right in my sweet, juicy bald pussy as shemale porn played in the background. When we were finished, we pulled down her panties and there were little drops coming from that cage. It was priceless so we took a picture. What do you think? Isn’t she cute?

Sissy Slave Training

sissy slave trainingI love sissy slave training my sissies. I have a few prized pupils. Some are married and must be very discreet with their sissy duties. Others are free to be the best sissy they can be. And a few are single but can only practice from the safety of their home because of stigma. They have jobs or parents that just wouldn’t understand. Breaks my heart when a sissy can’t be who she was born to be outside her home. I have two sissy boys. I knew when they were young what their true nature was. I didn’t guide them to be sissies. I let them explore their sexual identities. And those identities involved wearing mommy’s panties, playing with her make-up and sucking on her dildos. I’d buy them gender appropriate toys and they would play with their big sister’s old Barbie dolls instead. I stopped buying them boy things by the time they started school.  They are still in school, but they go to an arts school. Its LBGQT friendly. They can be themselves. The younger generation gets it. They don’t judge. For you older sissies, the best sissy trainer is a mommy who understands you can’t always be out sucking cock or going to stores and buying lingerie for yourself. I wish you could be like my sons, but I understand different generation and different situations. Regardless if you can go out and get cock and toys like my precious Bambi or you have to stay in the closet like Mickey, this sissy boy mommy wants to help you make the best of sissydom.