1,510 results for sissy training

Sissy phone sex with me turns even straight men into sissies

Sissy phone sexMy pathetic faggot little jizz mopper got his throat pounded today. I had him assume the Loser position as soon as his big juicy dick walked through the door. It was time for Sissy slave training and all I wanted to do was sit back and have my nails filed while watching him humiliate himself on my Onlyfans.. Before he got the excitement of getting his face fucked I had him stroke his teenie dick and imagine he was stroking my black friends big cock.. He dreams of actually having a cock the size that dangled in his face..

His worthless clit was helplessly precumming while being taunted with a mouth watering dick in his face.. I finally instructed him to latch on to the tip with no hands and swallow up every inch of that 13 inch cock.. Do it, Do it was all he heard as his eyes lit up and he drooled. I sat a shot glass on his peenie while it jumped for joy! I knew for certain just the feeling of that big black dick hitting his tonsils while I denied him a prostate milking would make him squirt. I drizzled his cum all over that big veiny glistening black cock and made him slurp his own nut up. All my OnlyFan subscribers acknowledge me as the Best sissy trainer. I have sluts lined up willing to pay any and everything just for a seat next to me.. Without even knowing what Mistress will have in mind.

They watch daily as I humiliate men with a micro peen for personal pleasure. It gets me so hot and my pussy so moist to chastise the weak. Men are mules; they feed off of my hypnotic energy! Anal stretching wasn’t an option for him; the only thing he was going to have up his ass was the frozen butt plug that I stuffed to melt in his ass. Goosebumps filled his body as he wiggled his ass, his version of pleading to allow access.. That was just too bad for my sissy fag, the only thing he was allowed to do was jerk it and eat it like a good slave boy. I whipped my clit on camera while he was in the background on all fours.. A thick creamy load filled his throat, a nice thick creamy treat for my naughty sissy boy. If I am not actively humiliating, I have sluts witnessing during Sissy phone sex where I humiliate and feminize all sorts of men. 

Best Sissy Trainer for My Glory Hole Goon – Goddess Addilyn

My name is Addilyn, Mistress Addilyn to you, and I am the Best Sissy Trainer. At least that is the case for my dear old man Glory Hole Goon. In her Sissy panties and all, this one shines. 
You see he tried to act straight, and pretend that he hated the thought of being a sissy faggot. Getting to the truth was as easy as creampie with this one.

I simply forced him down on his knees before me and had him lapping up the creampie from my beautiful cunt. She followed the rules like a good little cum slut sissy faggot.
Ok, so straight men have been known to be cuckolds and doing just this. But most straight men don’t start creaming and moaning like a bitch from the first taste of another mans jizz.
My glory hole goon however, showed her true colors. Worst yet, I pushed her face from my cunt and made her undress. She was trying to avoid this. Sooner than later I found out the truth.

There she was in Sissy panties and a silky training bra.


Oh, and the best part…. little sissy faggot Glory hole goon was creaming in those panties. She confessed that she loved to go to glory holes late at night and secretly suck off cock.

She even went to far as to take strange men’s dicks in her sweet panty covered ass cunt.

Best sissy trainer

Femboy Training Mistresses’ Fluffer!

Femboy Training


Some of my best work as a femboy training mistress is in teaching a good sissy to fluff hard cock for me! Yes, I absolutely do have my very own cock fluffer that I bring with me whenever I feel like getting down and dirty. My special sissy in panties is usually dressed up like my bimbo slut fuck toy in all pink! She’ll be all ready to shake some ass, gag on cock and get that D nice and hard for me. My bald wet twat needs thick veiny BBC and my sissies are some of the best BBC fluffer’s to ever give head. They have learned from the very best to suck dick and finger fuck ass just like their mistress. I’m a prostate milking cum queen and any sluts I femboy train will follow in their goddesses’ footsteps!

Femboy training sometimes requires a gentle touch.

Femboy trainingIt was raining out where this femboy training master lives, and while my pussy was in need of a good pumping and cumming, I felt the need to head around the back of my house and walk a little instead. I’d find a man soon after I got back, was what I thought. In fact, I called one while I walked, told him to show up at my house for a hot ride. Then I ran into a cute girl on the path, she was in torn clothing, drenched from the water, and her soft skin really stood out to me. I was gonna pass her by, she really wasn’t my problem even if I did feel sympathetic, that was until I noticed the cock. “Are you a guy?” I couldn’t help but ask, and at the shake of her head, I knew I’d found a sissy who would worship me very easily. “Come on.” I turned back. “Let’s get you cleaned up and clothed.”

One of the best decisions I’ve ever made. That’s a loyal sissy, doesn’t ever question me, I’ve had her lick my toes in front of visitors dozens of times just to prove she’s obedient to a fault. And when I’m feeling froggy, I have someone ready to lick me to a messy orgasm on the spot!

Cock Sucking Sissy Phone Chat!

Sissy Phone Chat

The best way to learn to suck dick like a pro is to have hot cock sucking sissy phone chat with sissy training mistress Raine! I’ve sucked more than a few dicks in my life because I’m a down and dirty phone dominatrix with a craving for deep throat fucking. I’d even say I’m the head bitch in charge of gobbling cock so any of my sissies must be trained to my standard! That’s why whenever I have nasty sissy phone chat, I make sure to tell them to grab their biggest dildo so we can practice slurping down big hard dick together. My sissies love it when I have my stud cock join us on a phone fuck so they can hear me gulping and gagging like a filthy mistress phone sex goddess. I have to make my sissies the best at swallowing cock because their sloppy top skills absolutely reflect on me and I have to maintain my reputation as the best bbc sissy trainer that money can buy!

Mistress Arabella Loves her Sissy maid!

Sissy maid training

You know you want to be the best little sissy you can be. Well, come to my Sissy maid training.

Being a good sissy is all you can think about, isn’t it? I mean let’s face it you aren’t man enough or woman enough, are you? You better work to be the best little sissy you can be. Otherwise, you are just worthless. Now, I am sure you want to look all pretty as a sissy, but that is not where we are going to start. First, I need to see your skills. How will I do that you wonder?

All we need is slutty red lipstick and a fat dildo. HMM, have you guessed what I have in store for your very first training? We are going to see how far you can deepthroat that cock. To be honest, I need to hear you gag on it and keep going if you are going to pass my very first class. So open wide little bitch.

Forced feminization for Sissy Sluts

Forced feminization

Have you ever thought about how Forced feminization is really necessary to break men of their pathetic toxic egos. Some men are wise enough to know that their ultimate place is behind a strong woman. Or between her thick muscular thighs. So many sissy bitches say oh they just want to be controlled and led by a mistress. But we really have to break their tiny/giant egos. Yes I said it. Some men think their pathetic holes will be filled by just going along with a mistress. But most sissy sluts have a breaking point where they really need to be pushed to. High pleasures only come with higher discomfort and pain. I save Femboy training only for sissy bitches who open themselves to being my pleasure tool, cuz they aren’t ready to be my personal slave.

I go overboard as a BBC sissy trainer for fun!

BBC sissy trainerThe collar clipped around his neck, the leash pressed into my hand, and my vibrator perfectly set up inside of me. I was ready to get on with my BBC sissy trainer ways. I’d started something so fun it had me giggling all night the night before just thinking about it. “Let’s go for a walk.” I said, and I saw fear in his eyes. I’d done this many times before in the house, but he definitely wasn’t ready to be brought out in public. I didn’t care about things like his shame, I had fun to have, and I knew he’d be a pansy no matter what I did. That’s kind of what a sissy is, a man who’s inner girl had taken over and caused him to crumble. A trainer like me was something much greater, so he’d do what I said, and he knew it before he even complained – which is why he didn’t, he just accepted the humiliation phone sex coming his way.. Instead he started crawling towards the door. I took great glee in opening it for him, and walking him out onto the city streets. My pussy was dripping down my leg, and he was so nervous it made me practically skip. I’d gone and done something so sexy I couldn’t control myself. I sat on his back, rubbed myself into him a little, and ordered him to keep going. He was a tougher sissy, one that could handle me like that at least a little, but you know what they say, the tougher they are the less mercy I give. He was an excuse to go overboard, he always was, and now he was crawling down the sidewalk while my juices wet his back, and people stared at him like he was insane. To be fair he had become my slave, to most people that would in fact be losing his mind. To me, it seemed like righteous obedience and sissy training success.

Femboy training for Basic bitches

Femboy training

It’s amazing how many basic vanilla bitches desire a walk on the wild side seeking Femboy training. They are underwhelmed with the monotony of vanilla plane jane life and they want to be a naughty Janet. These basic bitches (as I’ve dubbed them) have been scrolling pages of basic vanilla plain janes seeking something that excites them. However  the boxes they exist within leave zero space for imagination. The desires they have require them to step back from their egos and tame the boring beast inside of themselves. If one truly seeks submission into the unknown then one must pause on rushing to their finish line. Can a sissy girl hold her breath and dive deep into her mistresses pleasures?

His Sissy panties were in a bunch as I selfishly fucked BBC!

Sissy panties He is an obsessed white cuck slave.. My sissy snow-bunny loves having leftovers! I make him sit and watch me take joy rides on hard black long dick while he has his Sissy panties in a bunch. Being a cuck wasn’t a decision of his own; it was more of a command. We’ve been on and off dating for a while and his measly cock just isn’t pleasurable.. Every time he gets drunk he puts my clothes on and begs for us to go to bars downtown.. I’ve watched him prance around batting his lashes and chicken out, too many times.

That’s why I decided to start bringing black men home after a fun girls night out! He wakes up to the sounds of me moaning begging to be fucked harder every weekend. He knows to put his dick in chastity and come find me. I am always sure to be in a doggystyle position having every last one of my holes plugged with a big black cock. I know its more of a tease to have to watch 3 men fuck me hard rather than just one, so selfish! LOL… He drools as he watches me get fucked and not just out of his mouth..

This is only the start of Femboy training, he has no idea that as soon as I get bored of teasing him he is going to be the one plugged up.. That’s why I make him watch not just to tease but so he can learn. When I am through, getting a nice thick creampie I have him clean their black limp dicks of my pussy juice. Then give me oral until his jaw locks! I am always sure to save the orgasm for his face..

I smother him with my Cum filled cunt and grind my silky smooth pussy up and down until my clit explodes. This fucker is going to give in, he will soon be slaving for black cock as he truly desires. I am sick and tired of him not accepting his true self whether boyfriend and girlfriend or best friends till the end he will be my sissy 4evaaa! Even if it’s through Forced sissy training, he’s giving up his man pussy to something besides a rubber dick!