Category: Sissy humiliation training

I made that little bitch squirm

sissy phone sexLittle sissy bitches need lots of humiliation to really learn their place don’t you think? Even if they say they don’t like it they clearly do, their little clitties always get hard when I degrade them no matter how hard they cry. Well one of my little sissies tried to say that he never wanted to be humiliated, he said that this was a private thing can you believe that nonsense? So I forced him to dress up like a whore and  took him to the pool at a fancy country club and made him parade around in a bikini for everyone to see. He claimed that he hated all the people staring at him but his lil clit was poking out of his bikini bottom so that was a lie. I made him go to the private pool since he lied to me and back there I had all kinds of studs there to use him like that whore he was. I made sissy fluff them all up and even bent him over so they could fuck his lil pussy too, he claimed to hate it but I know better.

Celebrate Your Independence Now

Now that the 4th of July has passed, you can do some of your own personal celebrating with the best sissy trainer Diana. I love my Sissy sluts and want to be a part of their celebrating of their own identity independence. Accepting your true feminine selves is a big step and once you feel the freedom it offers to be so accepting you can celebrate You! I am here to offer some guidance and a friendly ear for you to get some of the stress or tension off that comes with wanting to be different that what others expect of you. I am the nurturing mommy that can be here for you and I accept you as you are and I will help you be the best little cock sucker you can be and the best little sissy you desire to be.

Best sissy trainer

Sissy Training on the 4th

sissy trainingMen call me for sissy training all day long. I don’t know why women don’t want to have a sissy. I love it. Every woman should have their own sissy. They will do anything you ask or want. They make the perfect maids. My sissy boys are well trained by me, their mommy. I had a little 4th of July cookout this afternoon. My sissy boys were the ones serving drinks and food. They also doled out blowjobs and cunt licks. Whatever my guests needed, by sissy servers delivered. I have some demanding friends too. My sissy servers swallowed a lot of cock and ate several pussies too. My friends love coming to my house because they are guaranteed to have their needs met. I had my sissy twins dressed in French Maid outfits too. White stockings framed their asses and little clit sticks. Their skirts were very short, so every guest could see their goods. Some of the women got fucked by some black bulls I had on hand and my sissy boys were there for cleanup duty because they had the best sissy trainer. They had me, their mommy. Are you as good of a sissy as my twins?

Dominating Jerry’s Wallet

Phone dominationDomination phone sexMy sexy naughty lil’ friend Katelyn is my owner and I am her submissive cunt. Together we have phone domination over pathetic piggy Jerry and drain his fat fucking wallet. He loves us and how we are able to disappear & place him on hold while masturbating without telling him or giving him any sort of warning whatsoever. He does not deserve to know when the fuck we are pleasuring ourselves!  All we have to do is fill up our syringes full of meth and inject him with it and he will continue to let us disintegrate his bank account all day long. That’s all that Jerry is good for and all that Katelyn and I give a fuck about anyways! If you don’t benefit us in a lucrative manner then we don’t fucking want you! Our financial needs are all that matters. Plus, Katelyn and I are size queens and Jerry’s pathetic little cock is so fucking hilariously small. Haha! Her and I are constantly cracking up at how it twitches while it attempts to get hard for us as he strokes it like the pathetic little pay piggy that he is. We tied him up to the bed so that he was laying spread eagle with his tiny pee pee wannabe scrotum sack on display for everyone to see! Katelyn had a whole bag full of paper clips for us heat up and brand & tattoo his cock with so that everyone knew who the fuck he belonged to! We blindfolded his pathetic face so that he couldn’t see all the fun that Katelyn and I had while we dominated the fuck out of him. I shot up his pee pee hole with meth and made sure to unleash every last drop into his blood stream! Jerry loves that we deliberately force him to be intoxicated with drugs and under our sexually erotic spell. He is too much fun to use and abuse and we love having domination phone sex with him! 😉

I blackmailed him

sissy phone sexThis little sissy slut was coming to me for training but for whatever reason he was very resistant. He even threw away all of his girlie clothes and panties and all that, can you believe that nonsense?? Well I was tired of his bad behavior so I went to his house and made him dress up with all the clothes I brought with me. Then I took a whole bunch of pictures and told him that if he eve disobeyed me again that I would publish them all and make sure that everyone he knew saw them. Oh boy he was definitely ready to obey me then! He was freaking out and crying and begging me to keep the pictures a secret, it was hysterical! I just laughed at him and told him that I would do whatever I felt like doing so he better keep me happy or else. Well, he handed me a wad of cash, took me shopping and promised that he would keep me happy so for now I will keep those pics to myself. I wonder how long he will last before he pisses me off…

Jerry Zeglier from Pennsylvania is such a sissy bitch

Mistress phone sexJerry Zeglier from Pennsylvania is such a sissy bitch. Robyn introduced us the other night on one of our sex chats phone line and what a pathetic son of a bitch he is. He was trying to tell me what I could do with him and I had to shut that shit down. Like I need his advice on how to use, abuse, or embarrass him. Such a looser to think that he can even talk to me in such a manner as if he was my equal. He pissed me off and all I wanted to do was whip him with my strap. The next time I talk with him he better know his fucking place and learn how to talk to me or I won’t be so lenient on his bitch ass.

Glory hole punishment

Taboo phone chat

One of my sissies needed a little lesson on obeying orders and listening to his mistress. He also needed to be punished and humiliated too. I had the perfect punishment for him! I took him to the nastiest and seediest sex club downtown dressed in fully sissy panties, makeup, and heels. He had to walk through the parking lot and the front of the club in nothing but panties, makeup, and 4″ slut heels. I lead him through the club to the grimy dirty bathroom stall and made him get down on his knees on the filth covered floor and wait by a hole in the disgusting wall for a big cock to poke through. A really dirty looking uncut cock slid through the hole and my little sissy started to gag when his face got near it. I gave him a sharp smack across his ass and told him if he didn’t start sucking, I’d put his ass up against the hole and let them fuck him. He hesitantly obeyed and sucked the nasty dick like a good little sissy bitch and even swallowed when his mouth was filled with cum. That was just the first dick too, I had him on his knees for hours sucking any dick that came along, no matter how filthy or dirty they were. This is what happens when sissies don’t obey their mistress. They need to be taught a lesson and punished. You have to remind them who’s in charge. I love humiliating a sissy and most of the time they love it too, even if they don’t want to admit that they love sucking big black cocks, but even sissies have their limits and don’t want to suck nasty dirty cocks from a filthy glory hole bathroom for hours. He should have thought of that before disobeying me though.

Become Your True Self w/ Femboy Training

He was so confused and really needed my Femboy training sessions. It was something Jamie was really uneasy about and felt he needed to hide it, but the urges and desires to be the Ladyboi he truly was could no longer be denied. He contacted me and after our first session was already feeling more accepted and excited about his ability to come out about his Sissy needs. He would hole himself up in a Hotel room outside of his town and bring he secret suitcase of all his pretty Sissy clothes, toys and accessories to be himself finally. He lied and said he was going out of town for work. He was really going out of town to be the sissy faggot he really wanted to be and wanted the nerve to really suck cock and hook up with a sexy tranny hooker. He always failed to get the nerve and just spent his time being a sissy online in the crossdresser kink sites where he would talk with others and share pictures. When he found me, he was finally able to gain the assurance and my training and strap-on play really brought the inner Sissy faggot out. If this sounds remotely like you, I would love to assist, I am always open to first timers and experienced Sissy’s alike. The humiliation and forced cocksucking is very exciting for me and I love making you my sissy submissive.

Femboy training

Sissy phone sex with the best

sissy phone sexSissy phone sex with the best bitches on the block, that is what you will find here, so when little bitchy faggots call me with an attitude I need to slap them right down to size. This little whore thought she could talk shit to me, as if I would bow down to a sissy can you believe that shit? I am a Goddess I bow to no one least of all some little sissy dick sucker! She needed to be taken down a peg so I called several of my friends over and we used that sissy slut until she learned that her place was at our feet. Sissy had to dress up and then get on her knees and suck all the dicks there. That included big black cocks, smaller white cocks and huge rubber strap on cocks that we were wearing. We really opened up that little whore’s pussy too, I bet that bitch won’t be sitting down for a week after last night! By the time we were thru with her she was begging us to stop and she promised to be a good girl in the future. We shall see tho, I think sissy enjoyed her punishment and will be back for more real soon!

Pussy Paradise

Sissy pantiesMy sugar daddy will spoil me to the end of the world. I had a blast in bora bora. Everything I wanted I got. I could see all the other sugar babies prancing around. It was pussy paradise to all the rich sugar daddies. My loving slave pet came along, and I had him dressed up. I had a sissy bikini for him and even plenty of sissy panties. I could see his eyes full of lust and wanting to be me. Well, slave pet you will have to enjoy being in my shadows and embarking in every journey I am in and being my dandy hand servant. I wanted to treat my pet with a sweet bukkake bash. I gathered around some of the locals. I had a few connects and I made it possible to get all the tour guides and their friends to cum blast, my sissy. I could see it was heaven for him.