Category: Online sissy training

Online Sissy Training Just Got Three Times Hotter!

Online Sissy TrainingWe just might be too much for you! Three Sexy Mistresses for online sissy training? You better be able to handle us. Seems as if we get a lot of three girl calls to humiliate mother fuckers like you. The Stunning Queen Bitch Arabella is skilled in the art of make-up and getting your cock up classes. Transforming you into a living breathing fuck doll. Only maybe the cock that’s getting a rise isn’t yours! Maybe that big Meaty Extra large cock is yours to please! Who am I fucking Kidding? Of course it is sissy boi! You need to look the part if you’re going to be a girly little dicked man! sissy humiliation training

Then Comes wicked Hottie Janie! The big cock size queen who knows how to pick a big dick out to humiliate your ass! The bigger the better and this Seductive Beauty Knows you could never be even half as hot as us. So as Mistress and queen of Kink Arabella is getting you dressed she is teasing you and making fun of you in drag!  Teasing your little prick and pulling out the measuring tape to document the small peen you have to carry around for the rest of your life.  Just part of your sissy humiliation Training that’s all! You have everything to be ashamed of! We know what makes you break, and you better be ready to break for your Mistresses of humiliatingly  sissy fun! sissy phone sex

Once you get a taste of us we become your addiction! Don’t worry baby, we won’t hurt you! Maybe rough you up a little and make that ass red with a little tight ass spanking! Three hotties laughing at you and making sure you get to have all the big dick you can handle, and pushing you to your knees so you can worship us and cock appropriately.  Bringing in the big guns to compare a shrimp clit sized dick with. Worship the cock that you can never have. We all three know how jealous you are. So get to cock sucking bitch. You know you deserve multi-girl sissy phone sex so you can be turned into the sissy bitch you were meant to be! 

Pleasure Me Sissy

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What would you do to get to run your tongue across Mistress Francis’ nipples or smooth slit? I can see you thinking about it right now – the teeny tiny bulge in your pretty nylon panties is telling me. You know that your little cock can’t please me, but your tongue can pleasure me for now. Let me sit down on the couch and spread my legs for you sissy. Crawl over here on your knees and bury your tongue between my legs. Use your tongue and run it up and down my pussy lips tapping my clit with each lick. That is it sissy, you are doing so good. Now let me grab your head and smash your face against me. Now lick sissy and don’t stop until my pussy juices run down your chin. Oh sissy, how good of you to please your mistress like you do. Now stand up in front of me so I can see you. Aww look at that tiny little wet spot forming in your panties. Now pull your panties down, grab that tiny dick and start jerking for me. Aww look at that tiny thing. Oh, sissy you amuse me so. Now let’s see your orgasm face, there you go. Now pull those panties back up and enjoy that warm cream between your legs.

Service Sissy Slaves

Online Sissy TrainingDoing online sissy training is not as easy as it might look. And ruling this kingdom is its Queen is even harder. I have to entertain several guests, regularly. And trying to keep those men interested is so difficult. Sometimes they bring their wives, and every once in a while their offspring.

Last night, I had a full house. It was the perfect time to show off my little sissy bitches. I dressed them to the nines, even stuffing their bra since their hormones were only just starting to work on their tits. Their little clitties were stored away in chastity cages, hidden underneath frilly silky panties. They wore sweet flowing gowns, and their hair had grown out long and was done into beautiful braids. My perfect princesses.

In the middle of dinner, I could see several of the men start to get antsy. So one by one I sent my little sissy sluts under the table. They unzipped their pants, and went to town sucking on their hard cocks. Well, the women started to wonder what was going on, and when they looked under the table and saw my pretty princesses down there slurping on their husbands cocks, well they got pretty jealous. More of my princess girls crawl under the table, moving the ladies panties to the side so they could look at their sweet pussies. Even the young ones were starting to wonder, and so I sent the last of my girls underneath of that table to play with those young sweetlings, giving them a taste of my Royal hospitality.

I know that this was your favorite lesson, being a service slave to me. I know that you still crave it to this day. To be used simply to pleasure my dinner guests, of course it can be done if that’s what I want. I’m in charge baby, and you’re forced feminization is all that I care about.

Humiliation Phone Sex

A Little Bit About the Best Sissy Trainer

best sissy trainerAre you looking for the best sissy trainer? You are in the right place. Not just with me either. All the sissy trainers at this company rock. Let me tell you a little bit about who I am as sissy trainer. I am a mature woman and a cock size queen. I have been a size queen since I was in high school. I date a lot of black men and that ruins you for white dicks. I married a white man, however. That was a mistake. I divorced a white man too. He did give me a hot teen slut daughter and two sissy boys. I raised them to be sissies because it was their destiny. They were cursed with small willies. They are what you would call gender fluid. They identify as both sexes. While I was raising them, I supplemented my support from my ex-husband with sissy training adult men. I did some BDSM work too. Now I am a phone trainer and take all my knowledge and experience to help you become the best sissy you were made to be. I am a nurturing mommy. That does not mean I will not punish you, because I am big on discipline. I just prefer to encourage your growth as a sissy and use humiliation when called for. Sissy calls are not all I do either. When you are a sissy trainer, cuckold husbands and adult babies call you too. I am a dominant woman, so I can handle all variations of a sissy. I am a fair sissy trainer, but not easy. I require dedication and you will do assignments like suck cock at glory holes for me. When you disappoint me, you see my bad ass bitch side. So, do you think I am the sissy trainer for you?

Sissy loved that BBC

best sissy trainerIf there is one thin little sissy boys love it’s a big black cock so I decided to reward my favorite sissy with one. This sissy is a good girl that always does as she’s told, she’s always dressed slutty for me and does her makeup. She never shows up here looking sloppy and if I tell her to go make me money, she works hard being a little ho until she has a good amount of money to bring me. She definitely earned a reward so I got her a big black bull with a huge cock and let him fuck the shit out of her. She was begging for that huge dick like a shameless little slut, it was so cute! He fucked her throat like it was a pussy and that whore was just taking it like a pro. Then he bent her over and fucked that lil sissy pussy and filled it with cum. Good girls get rewarded, are you a good girl too?

Phone Domination Times two!

Phone Domination

You never stood a chance when you called upon the phone domination skills of these two young sluts. You thought because we were innocent looking we would be softcore with you? Not a  chance in hell as that delicate ego was picked apart by My best friend Janie. She giggled and texted me what a loser you were. We had seen the pictures circulating at the school, and now we sought to play with you like a toy! You had no knowledge of the pictures before one popped up on your screen. That is when we died laughing. The two hottest girls in school knew you had the smallest dick ever! Janie told you that you would be a virgin for the rest of your life. I blurted a secret I knew, your little dick got hard in your tighty whities at the locker room shower. The Basketball team tells us you wear your underwear in the shower and that your best guy friend had showed you his dick and you had sucked it off! Nasty cocksucker! *giggles in cuckcold*  That erupted in a fit of laughter. You begged for a picture of our tits like the pathetic excuse you were. We agreed but we sent you all kinds of big black dick pictures we found on porn sites instead. But Janie had an Idea and I could not resist it, if you video called us we would go topless. The kicker was you had to stroke your tiny little penis for us. Too bad you had no clue that we could record our screen. The whole fucking high school would be viewing little penis stroking! Now Janie and I are Humiliation phone sex sluts, and you know how we got our start. So If you dare to become a plaything, you know where to find us!

Humiliation phone sex

Slip Into Those Sissy Panties and Call Me

sissy panties

I want to talk to those of you who keep telling me you want to be transformed into a sissy but keep backing out. You need to put your fucking sissy panties on and be a woman about this. You aren’t a real man, so I don’t know why you’d even want to keep up the pretense that you are. Just give in to what you know is your truth and live it. I’m losing my patience with you whiny ass bitches. I know you’ll do what’s right and call me and tell me you’re wearing your panties and that you’re ready for my sissy instructions.

Honestly, I don’t know how I’ll start with you. It just depends on my mood the day you call me. I might be gentle with you and get things started slowly, but I also might just bend you over right away and take a strap on cock to your sissy cunt. The less resistant to me you are, the more likely it is that I’ll be gentle with you. So if you’re ready to admit to me that you’re a sissy whore and are no longer a man, pick up the phone and call me.

Clean Me Up Sissy

Mistress Phone SexAre you feeling a bit slighted with the size of your dick? I feel slighted every time I see my miserable husband’s cock. That is what makes him a great cuck. While his cock is worthless to me the humiliation and look on my husband’s face as I am being fucked delights me. I like to invite other sissies to join me in my fun. I will have you both lick my visitors’ cock until it is hard and wet. Then one of you worthless asses can guide his cock into my juicy wet pussy. I see your mouth start watering as you lightly graze my wet cunt with your fingertips. You enjoyed that didn’t you? I can tell by the wet spots that are noticeable in the pretty pink panties you are wearing. Now sit on either side of me and watch as a real man pounds my pussy. Hear me moan? Something you will never be able to do for me. Look at those thick full balls banging against my ass, jealous, aren’t you? Watch as he glides in and out filling my cunt with his thick cum. Look it is leaking out of my tight hole. That was amazing wasn’t it. Now you two come and clean him up. Get between his balls and that thick head as well. Then you can take turns crawling between my legs and cleaning out my cunt. That is right my little cum sluts, lick it all up.

Royally Humiliated During Sissy Phone Sex

sissy phone sex
Welcome to the Humiliation chamber, my favorite place to be during sissy phone sex. Our lesson today involves one bad sissy girl, the one you see hanging from the ceiling just there. He’s naked, and his tiny cock has been released from it’s chastity cage. His arms are bound above him as he swings from the ceiling. I see how excited you are; you won’t be after you see what I do to him.
I circle him, riding crop in my hand as my black stiletto boots click click click on the floor as I pace. His body is rigid, terrified. The blindfold does it’s job, and the ball gag in his mouth prevents begging. I’ve been force feeding him watered down wine for hours. I love online sissy training. See the bulge in his belly? That’s his terribly full little bladder. I stroke his cock with the riding crop, and his wiggles and moans, trying to get as much contact as he can before I ghost away, leaving his balls full and his poor cock dripping.
I lay a few blows on his ass, but then start to beat where his agonized bursting bladder is. He knows he is forbidden from pissing until Queen Presley says it’s okay. I make three other of my sissy girls go, and stroke and fondle his cock and balls. The third one in my sissy training plays in his asshole. They edge him, getting him as close to the line as I dare let him. He’s begging, so I remove the ball gag. “Do you want to piss or cum?” I know if he cums, he’ll lose control. The poor sissy slut chooses to pee, but I make him watch as he has a huge accident in front of the whole court.
Of course we all laugh. What was his transgression, you ask? Oh, he couldn’t make me cum in under five minutes during his forced sissy training. I stare at the rest of my sissies, and grin maliciously. “Who’s next?”

Online Sissy Training

Anal Sissy Training with a Pogo Stick

sissy trainingAnal sissy training is so much fun. I have had a few unruly sissies who have protested my methods of anal training. You cannot be a good sissy if you cannot take a cock in your ass. I trained my own asshole to take big black cocks. A good sissy wants cock up her back door pussy. I had this one sissy about 5 years ago who wanted me to train her ass with unusual objects and large objects too. I was struggling to find things to fit in her asshole. This sissy had a cavern for a back door pussy. Her asshole was so big that a foot long black cock would feel small. I was not going to be defeated. I was going to find something to stuff that sissy ass. I have this belief that sissy training asses is key to being a good sissy. It is a sissy’s tightest hole. Well, not for this one sissy. One day, I saw my daughter in the backyard on her pogo stick and a light bulb went off. It was pink too. I thought okay it is a weird thing to put up even a sissy’s ass, but it was big enough to maybe stuff that sissy’s huge back door pussy. The next time my sissy was over for some anal training, I was ready. Readier than I had ever been. She fell in love with the pink pogo stick. When my sissy first saw it, she misunderstood its use. It was not to bounce around entertaining me. That pretty pink pogo stick was for anal sissy training. It was the first time I ever saw her eyes that huge. She could not believe I was going to try to put that up her back door hole. Plenty of lube and some deep breaths, anything will fit in any hole. I gave her a few shots of whisky. My sissy took it like a champ. I could not get it all up her ass, but she took far more than I thought she would. I finally found something to fit the gaping asshole of that sissy. I was so proud of myself. Trust me, I am a great sissy trainer. I will find something to gape your asshole too.

sissy training