Category: Online sissy training

Humiliation phone sex

humiliation phone sex

I love turning big manly men into princesses or babydolls. Something about shaming a small cock into being a little whore just turns me on so much! I met my last little girly girl through a humiliation phone sex call. She had such a tiny baby cock that there was no way I could let her call herself a man. To everyone else she might be David the tough guy but to me she will be Darla, my little princess. The first time I saw that pathetic little cock, I laughed until I was almost in tears! I knew exactly what needed to be done. After all, that’s why she came to me. To be transformed into what should have been in the first place. I dressed my sweet Darla up in white thigh high stockings with little bows on the tops, a pink and white frilly babydoll dress and the cutest little lacey panties. I made her rub her little pussy through those lacey panties until she was moaning softly for me. I told her not to make a mess in those pretty panties or she would be in trouble. Once I saw that her panties were all wet and sticky, I pulled them down and spanked her little ass until it was bright red. She’s not allowed to cum without my permission! As a punishment, I was going to show her what happens when bad whores don’t listen to their trainer! I called my friend over and let him fuck her sweet tight asshole as he reached around and played with that little hard clit. She cried for a while but she has to learn that I mean business! How can I expect her to be a sweet little princess if she can’t even keep her panties clean?

Teen Online Sissy Trainer Has A Sissy Boyfriend

online sissy trainingThis sexy online sissy training teen has a new boyfriend who I am turning into a sissy bitch! See he slipped up and told me that he secretly wears panties! So, I have been making him wear pretty satin and lace panties every time we have sex. He isn’t my normal type at all. But I needed a boyfriend around for family gatherings this year and his cock is just right on the average side. And being a sissy trainer, I had sissy-dar… An Internal Radar that told me he would be prime for turning into a sissy slut even if he didn’t know it yet! Kevin began to just wear his panties and he made a great cunt lick. He even loved it when I called him a perfect sissy.

Together we shaved him and waxed his balls. Hairless and with a pink thong in looked just like a girl from behind. It is an easy job sucking his dick and licking his ass hole. I tease him that he wanted to be just like me with a cock in his mouth. Then it happened one night at our party on the rooftop. I sucked his cock and gave him my panties in the bathroom for his to wear and feel like the sexy bitch he was. I commanded him to flirt with my gay friend Nathan and to let it go as far as he wanted it to go! Kevin ended up in his panties sucking off Nathans cock as he got called a cocksucking bitch and a good little whore. The best part was I was fucking the biggest Black Dick at the party while my fag sissy got her first cumshot! And you better believe his sissy girl training is just beginning!

More Sissy Panties for 2020

sissy pantiesHappy New Year sissies. I think we should celebrate with more sissy panties for you. I love dressing up my sissies. I mean how can you be a sissy in men’s clothes. I will dress you head to toe and turn you into the pretty girl that you have yearn to be. I began the new year, feminizing Taylor. His name is one of those names that could belong to a male or female, so I let him keep it. First order of business was to remove all the body hair. Since he lacks much testosterone, that was easy to do. A few coats of Nair, and Taylor had a smooth, feminine body. The next step was a make-up lesson. I showed my sissy how to draw attention to her lips. Men love a good pair of cock sucking lips. The final step was dress. You want to be a real sissy; you need to look the part too. And it means wearing more than just a pretty pair of panties. I had Taylor in some sexy lingerie. A pretty laced bra to match the panties, a garter belt and black stockings and even high heels. I gave her a pretty collar that said, “Diana’s Pet” and marched her down to the local truck stop to break her in. She netted me a pretty profit too. Taylor transformed with my training. You can too with some online sissy training.

Sissy Must Be Punished

Sissy Phone SexI had a sissy stop by today. He told me he had just gotten married and he wanted to be faithful to his new wife. I laughed loudly. I told that sweet sissy that while admirable, he would always be my little sissy and I would always be his mistress. He tried to argue but I quickly put him in his sissy place. I ordered him to get on all fours and to remain there until I returned. I reminded him that if he did not do as I obey, I would be giving that new wife a call and sending her some of my prize picture of her sissy husband. He hung his head as he sat on all fours in the floor in my office. I left him there to think about what he had done. I contemplated his punishment and returned. I told him I thought he had forgotten key parts of his sissy training. He was my tongue slave now to do with as I please. I informed him that we would need to increase our sessions to once a week until he was compliant again. If he did not show up, his new wife would be getting a surprise. He agreed. I told him for his disobedience he would be punished. I had him move his head towards the ground with that little ass up in the air. He was not worthy of a skin paddling so I paddled his ass through his pants hard. Making him thank me after each smack. He did as told like the good boy he was going to be. I did want to congratulate him on his marriage and give him a present. So, I climbed up on my desk and let him lick my sweet little ass with his tongue and finger my juicy pussy until the cum ran down my legs onto the desk. After cleaning up the desk puddle with his tongue, I told him what a good sissy he was and that I would see him next Tuesday. He smiled and left with the outline of his hard cock showing through his pants.

Sissy Phone Slut Gets Caught

sissy phone

My latest Sissy Phone slut had a story to share with his Mistress. He loves it when his wife and sister leave the house. This sissy slut goes in drawers and finds panties and stocking and garters. Dressed in slutty lingerie and six-inch heels he feels his true sissy side,  He rubs his sweet clitty as he envisions being caught and them putting him in sissy slut school. We all know what happens when he rubs his sissy clit. His boi pussy begins to throb and he has to go find something to fuck himself with.  It wasn’t long before he is lubed up and shoving that dildo in and out of his pussy screaming in his loudest girly voice “fuck me with that big cock!” Its buried in that sissy ass and he is leaning back on his heels bouncing on it, ore cum dripping all over the bed. He wanted his mommy’s big black boyfriend to be fucking that boi pussy. He wanted dirty and nasty to cum too so he snuck in mommies room and pretended to be her. He is squealing now saying fuck me with that big nigger cock! It was then that he got walked in on by the very person he wanted to be pounding that sissy boi ass. He was so embarrassed trying to cover up his secret sins. But that black hulk of a man walked over to him and demanded he/she suck that big nigger cock! Don’t you want to know how my sissy fag did? This BBC sissy trainer has the rest of the story baby!

 

My Daughter and I Love Sissy Slave Training

sissy slave training My daughter and I love sissy slave training you. My daughter is not of the right age to join me on calls, but she helps me with my real-time sissies, especially my sons. My daughter is a great sissy slut trainer. She is a high schooler, but she is already a size queen and a sissy slut trainer. I have been super busy on the phone this week. Honestly, I have never been this busy on the phone before. I guess the holidays are bringing the sissies out of the closets. With me being so busy, my real-time sissies have felt neglected. I don’t want that happening, so I told my daughter to fill in for me. A sissy trainer can be of any age. She is a hot teen girl and she has a love for humiliation and big cock. She takes after her mama. I finished a long call last night and went looking for my daughter. I couldn’t find her, so I checked the sissy training room. Curious what that is? I have a room in my house for sissy training. It has all the toys, equipment and clothes needed for me to be the best sissy trainer. I found my daughter there pegging the ass of one of my long-term sissies. He was wearing a frilly dress and she had on the black dildo. She was going a mile a minute on his ass and giggling with joy. It was a proud mama moment. My daughter may not have the years of experience that I do, but she is just as good of a sissy trainer as me. I guess the apple doesn’t fall far from the tree.

Pretty Toes for the Sissy

Sissy Training Now that Becky has some pretty panties it was time to do something with those hands and feet. So, I had sissy Becky get ready and we headed to the nail salon. We did the spa treatment as sissy had some nasty little feet and Mistress Francis will tolerate no such thing. Besides what is better than a nice pedicure peeping out of some nice heels. To make sure Becky remembered she was my inferior I had her wear black and white polka dotted panties under his white sweatpants so that everyone at the salon could see. They were pointing and talking the entire time we were there, and Becky hung his head in shame. After we were done, I pulled out Becky’s sandals and had him put them on right in the salon. He looked marvelous. As we were walking out, I could hear the laughter directed at him. I smiled and he hung his head, but I know he secretly loves it. We stopped at the market on the way home so Becky could show off her pretty panties and toes for all the shoppers. When we finally arrived home, I checked his little clitty and it was not hard, however there was some pre cum in those panties of his. Shame shame on Becky and he knew he would be punished. This time I decided I would just have him stand in the corner with his face to the wall wearing nothing but his panties and sandals showing off his pretty toes. Did I mention the corner was at the neighborhood gym? I sure hope Becky can keep that clitty under control with all those hard bodies and big dicks walking around. We will see… Don’t you like his pedicure?

Sissy Maid Training For A Cum Dump Like You

sissy maid trainingLift Your silk  Petticoats you are a sissy maid now and it is time for your spanking! Dear one did you think your transformation was complete with just your pretty little maid outfit? I will break you. Glitter lip gloss and pretty panties do not make a sissy. I have had better sissies wearing jeans and tight t-shirts. Your first step is going to be drinking cum from a tiny teacup after you serve your mistress. Pinkies out and lift up and show me your cage before you serve me pet. Not enough sugar, that’s three swats to your ass cheeks with my wooden paddle. Oh yes, red paddle lines! Now to crawl on your hands and knees between my legs and get the scent of a real woman that you will never be. I know now that spanking a sissy is not punishment but more of a reward, every pain I put you through makes you more of a sissy and you adore it. There is no harm in spanking my sweet small cocked fairy sissy maids at all. I know the next part of training is what you really want though. The biggest blackest cocks to fill your slutty troat and stomach up.  Get the lotion pet you are entering Mistress Zoeys Playroom.

Your sissy girl training will begin now!

sissy girl training

Sissy Slave Training and Punishment

sissy slave trainingSissy slave training with me is a special treat. That special treat is often in my pussy! I had a wild night last night. Three of my black lovers were over to fuck me. Now, my sissy sons were there and one of my real-time sissies too. This sissy was a naughty sissy. He worked his way on to my naughty list. He is in a cock cage. I am his mistress and his little clitty belongs to me. He doesn’t have a say when he touches himself. He can’t be trusted. He is a chronic masturbater. I paid him a surprise visit yesterday. I was checking up on him. He was not in his panties nor his cage. I made him put both back on then I drove him to my place for his punishment. If you have never been caged, you might not realize that getting an erection in one is very painful. I made him watch three black studs worship my body. I took away his spare key. I know how much he loves watching me with big black cocks. He is one of my many black cock sissy boys. I am the best sissy trainer for black cock faggots. My little BBC fag was in pain watching me take three huge black cocks. Once I was filled up with cum, I made him clean me up. Not only did he have to clean up the cum from my cunt, but he had to clean my pussy cream off those big black cocks too. Okay. Maybe I didn’t really punish him.

Sissy phone sex

Sissy phone sex I looked right into his pathetic beady eyes as he stared at my pussy taking that juicy nigger cock repeatedly! This is my favorite type of cuckold sex, taking thick nigger dick in front of a little wimpy cucky faggot who is just begging to get a taste of a real man’s cum dripping off of my pussy after a good hour-long pounding session. I regularly invite over a sissy little bitch to watch me get fucked and filled with cum just right to teach them their place and show them how a woman needs and deserves to be handled. If they are really lucky, at the end of the lesson I let them clean up the cum out of all of my holes but that only if they tell me over and over what a pathetic fake man they truly know they are. I laugh as they attempt to stroke their tiny pencil dick into a hard-on, that’s why they need me they’re worthless… and they need a woman who can tell them when they are allowed to cum, if at all. Do you think you deserve to cum today?