Category: Humiliation phone sex

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.

I made her do it

sissy phone sexMy newest little sissy bitch was reluctant to follow all of my rules so I had to punish her. And what better way to punish her than to make her do all the things she was reluctant to do in the first place right? So after she was all dressed up like a little slut I told her I was taking her out for a little surprise and boy did she get all excited. She was acting like she had been a good girl that deserved a treat or something and seriously nothing could be further from the truth. She was really a pain in my ass with all her complaining but that was gonna be changing real quick. I led her into this private club where I had all her clients all lined up and waiting for her. She was going to have to serve each and every one of them before we left there or she would no longer be my sissy. Well she cried about it but you know what? She sucked every fucking dick in the place! They fucked that tight lil pussy of hers too until she had cum running down her legs and she was too tired to stand up. Only then did I take her home and let her rest.

Some Sissies Need a Lot of Force

forced feminization

A lot of guys say they are into being sissified, but when push comes to shove they always end up backing out of the fun I have planned for them. But the next time I set up a feminization session, I will definitely have a back up plan in place. I’m going to take them to a place that has a nice security setup so they can’t get away from me. If forced feminization is what I have to do, then that’s what I’ll do.
Just imagine you are the person I am getting ready to feminize. You get scared when it feels like things are starting to get real. But when you try to get out of the room, you realize you can’t open it. You’re my sissy prisoner and I’m going to turn you into a sissy slut if it’s the last thing I do. You’ll put on the clothes I tell you to. You’ll learn to apply your makeup and if I can see that you aren’t trying, you are definitely getting a spanking. And when it’s time for your cock sucking and fucking lessons, you better do them with a smile on your face. When you’re ready to submit, give me a call.

Best Sissy Trainer Teaches Cock Whores

Mistress mommy Diana is the best sissy trainer in the burbs. I have so many family man types that aren’t really men. These guys play the role well but they don’t fool me! I know a closet sissy when I see one. They are often busy professionals in their 50’s that need to let it all go. These guys can’t be themselves most of the time and visit me to be sissified and used. My sissies vary so much though. I love them all as a mommy loves her obedient good boys. I am open to being your sissy mommy and you can serve me and watch me get fucked. Clean my creampie like a good little cum slut. I will have you wearing my silky panties and whore lipstick as you learn to be a cock sucking, cum guzzling, sissy slave to big dick.

Best sissy trainer

Overdue For Forced Sissy Training

Forced sissy training

Are you a good sissy slut? I fucking don’t think so, Its time for forced sissy training sissy whore! Well, you’re not even a whore yet, are you?  I am part of the generation that gets what I want and when I want it. If I want you to wear only panties and mop my floor with your tongue, then You will do it. You ache so much for that black cock but you don’t want to work for it. What are you afraid of bitch boi? That once you take that big black dick in your mouth you are never going to want to stop? That your little clitty will explode just from the magnificent taste of that precum on your tongue? You are not a man, and sissy boi’s suck dick, the bigger the better. And this sissy trainer happens to be a black cock lover. Once you go black you never go back. And once you go sissy you never get pussy! Come play on the dark side of you black cock lust! I won’t promise you a good time, you don’t deserve it!

Sissy was a whore for Valentine’s Day

sissy phone sexI made sissy a whore for Valentine’s Day, I dressed her up in a sexy red dress and black heels and put her out on the street corner looking for johns. I made her ask every single car that stopped if they wanted to party and trust me, little sissy was kept very busy all day long. She was all excited seeing all the money she was making but I nipped that shit right in the bud. All the money she ever makes belongs to me and I made sure to take every penny from her. She was sad at first but I reminded her that I was her Mistress and it was Valentine’s Day so I deserved every penny. She was too busy sucking those huge black cocks to really disagree with me and besides, this whore would suck dick for free anyway so why does she think she needs to be paid for it now??

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 Hypno Training W/ Hot Mistress Gemini!

sissy hypno training

You bet your sweet ass you are in trouble now sissy slut! Gemini is the hot Domme who is joining me in sissy Hypno training! Guess who is a cock sucking, cum eating Faggot? One guess, It’s you! And who is going to jack off that clit while repeating to your sexy Young Mistresses? One guess, It’s you, Just pathetic cum-guzzling whore! Once again who is a cum eating cocksucker sissy whore? Yeppers, you are! Gemini and I have teamed up to bring you the hardcore sissy hypnosis that your pretty faggy face deserves. You will be guzzling so much cum from those Big cocks that you will be breathless as your clit gets sore by how much and how hard you jack it for us. Now, We are not going to ask you again little cock sucking whore. Who is the biggest BBC cock sucker who loves eating cum? You fucking guess it sissy slut! It’s your Black cock addicted whore self! Now on your knees Bitch, Its time for your Sissy humiliation training from The sexy Gemini and myself.

 

Sissy Humiliation Training

Stevie gets her Clitty Spanked

Sissy Girl TrainingYou see those nice acrylic high heels I am wearing? And those short shorts and cut off tank top? Those are things that my sissy Stevie begs to wear. But Stevie has been a bad girl. She has become quite the little slut and can’t get enough of pounding her little man pussy with her big black dildo. Normally that would not be a problem, but Stevie leaves her little clitty messes all over the place and never cleans them up. So today I decided that Stevie was going to learn to clean up all her little cunnies and as a reward she could wear this outfit of mine she so longs to wear. We started by removing her butt plug and inserting a remote-control dildo, that will vibrate whenever I press the button. Stevie put on some satin panties and we sat down to watch her favorite shemale porn. Less than 5 minutes in and she had already made a mess. I ordered her to clean it up and she back talked. I pulled those panties down and smacked that clitty with a wooden spoon a few times and told her I would continue until she cleaned up her mess. Tears filled her eyes as she licked them all up. I then started the tape again. Same thing, 5 minutes and back talk. More clitty spanking and then finally she cleaned it up. She is a tough one. I then turned on that vibrator and started the tape again but this time I didn’t stop it as she made mess after mess after mess. I told her not to touch her mess, just yet. After her panties were soaked and it was running down her legs, I took them off and put them in her mouth to chew, therefore forcing her to clean herself. I got her a fresh pair of panties and put back on the tape. I told her that we will continue all night if we have too. After a few pair of fresh panties and a few more clitty smacks she was immediately cleaning up her cunnies. As a reward, I removed my outfit and let her wear it. She looked beautiful.

Best sissy trainer

Best sissy trainerMistress phone sexMost of you know me as the bitch that always gets her way and the best sissy trainer. The bitch that spends her time tormenting little cuckys and pathetic sissys. But today I am going to be teaching someone else how to be as bitchy as I am! She is a very young one, but don’t let that fool you. I sent one of my favorite sissy bitches to Aiden, she loves to torture and torment. This sissy bitch likes to have pain inflicted upon him and feel so many cocks filling up his holes that he couldn’t even count how many. That isn’t it though he loves to be humiliated. He wanted to be a pretty girl, not a fake loser man. So he begged Aiden and me to cut off his goods. What he had was small and wimpy. He was forced to call us Mistress and forced to watch as many other men pleasured our holes. Then we made him eat the cum out of our cunts. We were going to really make him suffer as he wanted, he begged to be our little pain slut. You won’t believe what I taught Aiden to do.