Category: Online sissy training

Sissy Humiliation Training: All Pathetic Sluts Need Proper Training.

Sissy Humiliation TrainingSissy humiliation training is a need for all sissified men who need to learn their place that the feet of superior women. Some fake men are born with very little in their life, and I am not talking about monetary gain. I am talking about the little tic-tac they keep hidden in their panties, hoping no one discovers just how much of a pathetic loser they are. However, a superior teen Princess like me can smell it in the air whenever a little limp-dick loser makes his way in front of my presence. That is why sissified losers need the proper training in order to learn their real place in life. Start with chastity. You should keep that gross thing locked up tight so that you never touch it unless you get permission. Burn all your fake make boxers and briefs. From now on sissy women’s panties will be all that you wear. That includes work in front of all your real manly peers. Get yourself a big cock from Amazon and get ready to practice your cock sucking skills. After all, a real sissy needs to learn how to serve superior cock since they don’t have one themselves. You are about to be humiliated in a way that feels so good, just like the bitch you were always meant to be.

Welcome To Mistress Arabella’s Sissy Academy

Online sissy training

Welcome to lesson 1 of my Online sissy training academy, where boys go to become very sexy girls.

You have always wanted to be a sexy girl but unfortunately for you, you were born with that pesky thing they call a cock. Well darling today, we will begin the process of turning that cock into a glorious clitty. And ridding you of all your masculine ways.

Panties, Perfume, and fuck me heels.

Now darling I hope that you like panties, Perfume, High stripper heels and cock sucking lipstick shades. I plan on turning you into the perfect sissy slut. It will take some time, but I am sure if you put in the effort and time on your knees that you will pass with flying colors.

Embrace your inner sissy slut.

Now for lesson 1, I want you to slide into those sexy pink satin panties and say goodbye to the little cock. Feel how your sexy clitty loves the feel of satin and how she begins to drip in anticipation of what you will experience in Mistress Arabella’s Sissy Academy.

 

Sissy phone sex with Miss Remi

 

sissy phone sex

 

I just had the best time dominating the plumber that my landlord sent over and making him my bitch. I’m going to tell you all about it on our sissy phone sex call! He was here to unclog my bathtub but he ended up getting his pipes cleared instead! I walked by the bathroom and noticed just a hint of his bright pink, lace thong sticking up out of his pants. What a perfect coincidence that a sissy, panty slut would be sent to my apartment! I didn’t mention seeing his panties when I was talking to him, I just left the room and came back wearing my biggest strap-on. He was a big guy and he was already on his knees, wedged between my bathtub and the wall, so he wasn’t going anywhere. I walked right up behind him and started to tease him, telling him that I could see his panties and I knew that he was a sissy bitch. He tried to hurry up and stand up but I pushed him down, held him over the edge of the bathtub and pulled his pants down. I slid my finger up under his thong and pulled it to the side while I started thrusting and shoving the head of my fat, fake cock into him. He tried to act like he didn’t want it but as soon as it was in, he was moaning and arching his back to take it deeper! I was so busy force fucking him and making him whimper and moan that I didn’t notice when my boyfriend walked in. It was perfect timing because that little sissy plumber slut needed a fat dick down his throat while I pumped him. Call me so I can tell you what happened once my boyfriend got ahold of that sissy bitch!

Humiliation Phone Sex: The Smaller The Better!

Humiliation Phone Sex

So many times, I’ve been asked if I’d like to be entertained by small cock humiliation phone sex and my answer is always, yes! A goddess like me can only get fucked by the biggest of cock because I’m a size queen. I believe in training my sissies to be obsessed with big cocks too so the only use I see for a little tiny cock is to make me laugh. I love seeing how absolutely miniature a cock is next to a nice big dick that I’ve sucked hard. The comparison alone is enough to make me giggle. Those tiny cocks might as well be clits and the boys with them might as well be chicks! Small cock humiliation phone sex is my favorite pastime if I’m not busy being the best BBC sissy trainer for sluts who want to serve me!

Best sissy trainer gets you addicted

When you have been trained by the Best sissy trainer, you become a cum addict. All you think about is the next moment mistress Gypsy will use you to milk a BBC. Since I work with BBC trainers I will always keep you full of cum. I want you in your sissy uniform I have picked for you and on your knees waiting to serve us in any way. Tonight I wanted to have you dripping before you milked any cock. I love seeing what a good cum whore you are. We teased you by making you suck on each and everyone of our toes like they were dick you needed to milk. I made you lick my asshole while my BBC trainer friend put his toes inside your Sissy panties and teased your sissy pussy. That had your clitty hard, especially when he shoved his toes in your pussy. You start begging me to let you milk my BBC buddy. As I laugh, I open your mouth and guide your head on his thick long cock. Right away he face fucks you hard, making you gag and choke until you have tears flowing down your face. Your little clitty leaked through your panties and when he started filling your mouth up with thick yummy cum, your clitty squirted. That shows me you are an addict to the cock.

Best sissy trainer

Sissy Training is My Specialty, and So is Being a Loving Mommy

sissy trainingSissy training is my specialty, but I get a lot of mommy calls too. I guess you could call me a sissy mom. I have two trans sons. When I first started this job, my boys were schoolboys. Just young boys who liked to play dress up in mommy’s clothes and play with make-up. I knew then that they were special. I mean boys their age played with cars, Legos and trucks. They wanted to wear jeans and t-shirts. I let them be who they were. I think it is harmful to stifle a young one’s natural exploration to find out who he or she is. Most women are not as enlightened as me, though. I get all sorts of sissy phone sex callers who talk to me about how they were shamed and ridiculed, even punished by their parents when they got caught wearing mommy’s pretty things. Some of these men are pretty fucked up because their parents just did not understand.

I like to recreate the mothering experience with callers. Be that nurturing, loving, encouraging mother that they should have had. The kind of mother my boys have. My twins are living their lives in that in-between world that scares so many people these days. They go to an arts school where their creativity  can blossom. They go to a school where they can wear dresses and makeup to school daily. They have friends. They have boyfriends. They thrive socially. Regular school was not so welcoming, but I recognized that immediately and switched their schools. What mother does not want her offspring to thrive? When they are 18, they can decide if they want to have sex reassignment surgery, or become trans girls. Whatever they choose, I will support because that it what a good parent does. They support their offspring. And the best sissy trainer supports you. Nurtures you, encourages you and only punishes you in order to train you properly.  Mommy is waiting for you boys.

His first Sissy training session went well

Sissy trainingThere is a new sissy in town and he’s going to be squeezing his little link into his first pair of Sissy panties! He was at work when his asshole started feeling all slimy, he couldn’t help the tingly sensation that ran through his body.. He needed a fix, even if that meant in the parking lot of his place of employment.. Risky business! He took his 15 and called me up from the back seat of his compact car..

He didn’t have any toys so we settled with his fingers! He slicked his tips up by slurping and sucking them, like they were a fat cock.. Then smacked the excess saliva that he scooped up from his chin onto his manhole.. The windows of his car were not tinted but they did naturally fog after a while of his huffing from the sensational fuck he was giving himself; while I whispered humiliating things into his ear.. He or should I say she?

Anyway, the faggot is aware of his position.. Not every call will he get off; sometimes he may even just have to sit back and listen to me breathe.. I mean whatever it takes to talk to a hottie, you couldn’t stand a chance with in reality! uhh, the good in fantasy, huh? haha, Sissy training has only just begun, we went shopping for some fun stuff..

So far we’ve gotten a clear 7.3in soft realistic dildo to gag his bussy with and a plus size contrast lace mesh slip with a matching thong… It’s even got a satin bow that sits right between his knockers. I can’t wait until it arrives so I can show the world that a Sexy BBW does exist.. His juicy phat ass is going to look amazing sucking up a g string.. He has never had his man hole stretched with anything besides his finger.. Lucky him, I am the sexy bitch who’s going to break him in. Welcome bitch, You’ve got yourself the Best sissy trainer on the net, Good taste!

OMG! You Just Woke Up as an Anime Girl!

Sissy training audio

 

In this listening session, all you need to do is sit back, relax and listen to the sound of my words. 

You slowly wake up and stretch, ready to get washed up and dressed. As you get up, you notice your body feels different than usual. You look down to see what is going on and you see a massive pair of tits on your chest. You run to the bathroom, desperate to see if someone has pulled a prank on you as your giant tits bounce up and down with each step. With one glance, you realize that you have been transformed into a beautiful anime girl. You have big bouncing boobs that jiggle when you breathe, a tight slim waist, and a nice round ass. You are ultimately feminine, beautiful and fuckable. You walk out of the house with your night clothes on, consisting of only a see-through white tank top and tiny shorts, and you capture the attention of all the men in the neighborhood. Seeing you in this outfit makes their cocks hard and they rush after you. You try to go back inside, but it’s too late. They have already grabbed you and started ripping your clothes off. 

You can’t fight back as they fuck you every which way. They stuff their cocks in your pussy and your ass, something you have not experienced before. Your new virginity does not matter to these men as they use you as a cock sleeve. One of the men starts playing with your tits, squeezing them and bouncing them up and down. No need for that as the men behind you are pounding you so hard your tits bounce on their own. Open wide! An army of big cocks are ready to force themselves down your tiny throat. 

Sissy Gurl Mistress phone sex

Mistress Phone sex

 Nothing gets my sweet MIstress phone sex pussy off more than making fun of soft bitches like you! Laughing and teasing your ass for being such a limp dick little sissy cock loving faggot.  I had so much fun the other day with you confessing to me how much of a sissy faggot you are. 

Zoey Knows you couldn’t wait to tell your Daddy all about me when he got home today. I heard all about how he surprised you with a super cute new outfit to wear for him and we had a couple of his daughter’s friends come over and laugh and make fun of you while he bent that tight ass over and made you whine like a little whore as he pounded you in my brand new short, tight mini dress. And I got even more turned on as the girls laughed and called sissy la-la a cock loving little faggot when his Daddy put her on her knees and blasted a weeks-long load he was saving up, all over that femme face.

There you are dressed up like a whore in a tight pink little mini dress, with a wet, throbbing, gaping, freshly fucked asshole, completely covered in cum, with three of the hottest little sluts laughing at your ass calling sissy all kinds of names, putting slut girl in her place, as a submissive, crossdressing, little cock whore. Thank you Sissy fag boy for letting me take your confessions and sharing my love for cock. I just wish one day I could be right there watching and laughing at you whining like a slut from getting pounded by a stud’s big cock! Thank you for allowing this Phone dominatrix to work you over SIssy Gurl! 

Be my sissy

phone domination

Do you want phone domination by a goddess who will make you quite the sissy? I know you want to be able to suck cock freely and become a full-time sissy. Let’s get you over to hustlers so we can get you some outfits to try on. You’ll be my sissy slut and be fucking for the dollar. Most sissies like to have a firm, stern goddess to guide them. You know I am the epitome of tough love. I am not mean because I want to be; I am only trying to make the best sissies possible. Only the strong will make it and can conquer all the sissy tasks put in play. When you do what I say, you become one of the greatest sluts.