1,510 results for sissy training

Sissy phone sex with Miss Remi

sissy phone sex

If you’re a secret panty slut and crave a fat dick in your mouth but aren’t brave enough to pursue your wildest dreams then you need my help! Miss Remi is the sissy phone sex trainer that will teach you exactly how to become the cum dump slut that you’ve always been deep down. Let me show you how to tease and please and be the perfect sissy bitch cum lover! Your knees are going to be raw and bleeding after I get finished fucking your mouth with my strap-on and teaching you how not to choke when you’re throating that meat! I have to teach you to take it like a pro so you don’t embarrass me when I bring in my bbc studs and turn them loose on you! I better see those skills that I taught you when they ram their dicks in your mouth. Circle the head of their huge cocks with your tongue and lick up the salty drips of precum that come oozing out! They’re going to want your slut hole next so get ready to be spread open and fucked hard! By then you’ll know how to arch your back, spread your slut pussy open and invite those massive cocks into your slutty hole! Let’s get your training started now!

 

Femboy Training My Daughter’s Best Friend with Her

femboy trainingMy daughter’s friend needed femboy training. He came to her and asked her for help. She consulted me first. She is in training to be a mini me, but this is her bestie. She wants to make sure she does him justice. I get it. It is hard to mix business with pleasure. I told her a couple years ago this day would come. Like her brothers, her bestie is not like other boys. When he was a young teen boy, I would find him playing in my dirty hamper and my panty drawer. He was a staple over here in his school days because his mom was a single mom and she often worked late. He would walk home from school with my daughter, and his mom would pick him up later. I considered him a bonus boy. I still do. I suggested she bring him over and we have a play date. My daughter and I are both good with hair, makeup and wardrobe. She is my mini me after all. I put Marc in sissy panties and suggested he burn his boxer briefs for good. This was the first time I saw him naked. Marcus was transformed into Maria with my daughter’s help. She has a micro penis that belongs in panties. Can you relate? My daughter picked out a very girly outfit for Maria. I fitted her with a wig and we both did her makeup. Honestly, Maria could be a ladyboy. Not full trans with a little clitty like that, but a ladyboy for sure. Maria seemed to blossom before our eyes as we transformed her from a he to a she. I am jealous of her slim body and high cheekbones. My daughter and I make a great sissy training duo. Now she has a best girlfriend instead of a best boyfriend and I have another bonus daughter.

It Was Such An Intense Surprise Femboy Training Session!

Femboy TrainingOne time I went on a blind date and the guy came to pick me up at my place, he had no idea it would turn into femboy training. I wasn’t quite dressed yet so when I answered the door I asked him to come in. However, when I answered I could tell he was a sissified cuck just by the way he looked at me. I continued to get ready when I noticed him eyeing some dresses in my closet. I figured, fuck it, I might as well get something from this date since it clearly wasn’t going to be a dick. 

So I encourage him to put the dress on. Of course, he resisted at first, but after very little convincing, I had him in my bra, panties, and dress. I also had him try on a pair of my heels. Surprisingly they fit his teenie tiny feet. Telling me that his little winky was far from substantial. I gathered it was probably tiny like a tik tac and that was just gross to me. As he tried to take it off I told him no. We would not be going on any date. 

Instead, I ordered him to start cleaning my kitchen. Like a good little bitch he got to work and I invited over a few of my friends. I introduced the dude as Ashley with girl pronouns. Sure he was an ugly femme but my friends didn’t give a fuck. I knew every last snicker and laugh made his tiny little dingy hard. He served us all night like he was our maid. Even using a high-pitched female tone. However, at the end of the night, we sent her home. There was no way we wanted or intended to play with that. We invited a few studs to fuck us to finish as we deserve. 

Lucky, took his Sissy panties off to plug his man pussy xD

Sissy panties I just saw my Lucky sissy in a pair of Sissy panties for the first time! We talk regularly but we had never done a skype session until today.. I have to admit he is so much hotter than I even expected.. He was wearing a cute pink and white bikini top, bikini bottom and thigh high socks that matched his sexy feminine fit. He whipped his tiny dick with the head of his purple and white 10 inch silicone cock while telling me how proud he is to be a fucking faggot! Before we got started we made sure he stretched his anus with his new butt plug..

A cute little tail hung out of his manhole as he pranced around like the faggot he is. It was so exciting seeing him bent over with his face in the camera and a massive dick right in front of his face.. He ran his tongue up, down and in circles with his eyes rolling back, quite impressive faggot. It was so big the cock sucker could barely get the rubber dick down his throat.. Of course, being on the line with The Best sissy trainer, I had to teach him how to properly deepthroat without gag reflex.. He huffed as if he was fogging up a window and the thick dick managed to dig deeper into his throat..

The windows were wide open and so were the blinds, so it is possible the neighbors might of heard or seen my favorite sexy Faggot deepthroating and gagging! To my surprise his dick actually grew another 2 inches from being so stimulated from double penetration. He sat on the floor with his legs spread, swaying his ass against the hardwood floor and whipping his clit with lubricant. I made him record every moment of his faggotry so her can see for himself why he should be proud to be the hot faggot that he is. Femboy training went well and my sexy, hot, naughty and just overall purrfect sissy kept his mistress smiling ear to ear! 

Femboy Training needs lots of Pink

femboy trainingFemboy training is all about that pink! From ruffled pink sissy dresses to pink cock cages and Botty holes, PINK is the universal sissy color! There should never be too much pink in your life! Some of my favorite little whores have pink hair and I’m down for it! My Rode-OH harness panties are pink and My strap has a beautiful pink swirl in the black silicone! My mechanic is a sissy who loves pink and getting her pink puckered ass  fucked!  and I pay for car repairs with my snap-on strap-on! I love when mommy Zoey needs an oil change and ends up changing her Car monkey’s oil at the same time! Nothing like going out to the gay bars and seeing my Favorite blue-collar bear strutting his shit in all pink as she sings Madonna, knowing that butt plug and cock cage are still held in tight under my command. My momma always said to have a sissy in every corner and I think she just might be right! What part of my life can you help me with while I keep you as my pink femboy!

Sissy Phone Sex with a Mix of Cock and Ball Torture

sissy phone sexSissy phone sex anyone? I am a sissy mom. I love my job too. Nothing more rewarding than helping a sissy reach her full potential. But sissies are not the only ones I talk to or even see in my private practice. I morphed into being a sissy trainer from domination. Yes, I was a full-fledged dominatrix. I did sensual domination, still do, but I could be a total bad ass if that is what you wanted or needed. I miss it sometimes. I would flog cocks and balls. Sometimes, I even did some extreme ball busting. I love cock and ball torture. I sometimes mix CBT with sissy training. I have a new sissy who is a total pain slut. She needs the pain to get off. And guess what? I fell right back into being a total bad ass.  When my sissy explained that she used to see a dominatrix and learned that ball busting is fun, I knew she was craving some ball torture. I had her gather a few things from her house like rubber bands, a spatula and some safety pins. Plus, I asked if she had any Ben Gay or something similar and cotton swabs. I bet you know where I am going with this, right? This was a phone sex call, so I had to trust that my pain slut sissy was indeed doing what I told her. We began our session with rubber bands around her tiny, worthless balls. Stopping the flow of blood is painful. Leave bands on too long and you can castrate yourself. I had him whip his balls with the spatula and then insert safety pins in his ball sack. I could hear the pain in his quivering voice. He knew I was his phone sex dominatrix and he listened to me. While his balls were tied up and sore, I had him use a cotton swab coated in Ben Gay in his pee hole. Sort of a painful sounding device. Maybe, a more painful one. He wanted a real CBT call, and he got it. This sissy mom can be a bad ass bitch. Think you can handle a session with me?

BBC sissy trainer like me are always ready to fuck your ass!

BBC sissy trainerI decided to use one of my BBC sissy trainer strap-ons to play with one of my sissies, laying him down on his stomach, I sat on his legs and contemplated the both of us. He was so available, always so giving and unable to deny me for even a second. I’m a good master, nice and powerful and rewarding, maybe that’s why I have such enviable loyalty? What mattered more than all that was palming that ass of his and squeezing it in my palms. I love the sound my sissies make when I show appreciation for their bodies before getting into things. I’ve always found a good pegging comes with a gentle hand and a sensual touch that adds a sparkle to any given moments. “You ready? I don’t really care if you are,” I admitted after a second the Best sissy trainer uses her skills to feel a plaything out, “but it’s always nicer if you are excited to feel it inside you.” I adore that little nod, too embarrassed to voice their desires and efforts, but also so eager to please me that they can’t resist giving me something. “Good, thank you~!”

Already lubed up and ready for anal destruction – not that I’m about to destroy anything – my bitch buster dildo is an imposing piece that hangs strapped right around my clit so that after every thrust I’ll have a good chance to hit it just right for my eyes to roll back and my hips to start fucking on their own. That’s just a thing that happens when I get real into it, and I’m always happier with a session if I’m also glowing from a powerful orgasm that caused me to lose it and start pumping. “Let’s gooo!” I don’t wait any longer, perfectly lined up with his girly hips, the tip of my fake cock pressed into his asshole. All I have to do is press forward, so I do with a lightning fast push that splits him open and has me moving in for femboy training and selfish desires!

BBC Sissy Trainer Will Stretch Your Ass!

BBC Sissy Trainer

Being a BBC sissy trainer means that I turn curious sissies into complete fuck toys for some of my big black studly friends! One of my new sissy slave training babies asked me what does it take to ride a BBC? I told that little slut it takes a whole lot of anal training! It’s not easy being split open and used like a fuck sleeve on a BBC… you have to submit to me completely, you have to want to be owned by that big black stud cock. My online sissy training got her stretching that fuckhole in no time; we started with a small six-inch dildo, stretching while we chatted and had sissy phone sex. It only took a week to get my sissy taking an 11-inch BBC because I’m the best sissy trainer for femboy training!

Best sissy trainer Goddess Genesis

Best sissy trainer

Genesis is the Best sissy trainer on this site. She knows how to dominate and make sissy bitch boys out of the ladies that frequent this site. So many pathetic sissy brats grow into self obsessed unsatisfied pussies. Pussies like that must be guided into submission. Some don’t have the space within their egos to handle the truth. Yet others can tell from early on that there was no competition. Women way out weighed what they were doing with their lives or what they ever could do. The most pleasure they would get would be through seeking the ability to please a glorious Goddess like myself.  

It’s so easy to get these bitch boys into Forced feminization for cocks that can actually please me. BBC is all that can contain my cunt. The thrilling pump of rock hard black cock pumping my cunt. And you can be the bitch to warm that cock up for my cunt. If your really amazing I will begin sissy humiliation training and allow you to eat the cum from my cunt when he is done. 

You’re a sissy phone sex whore with a dirty secret

Sissy phone sex

When it comes to sissy phone sex, I’ll expose all of your dirty secrets. I know how you have been jerking men off in the woods, back alleys, and even hotel rooms! You’ve been dressing up in skimpy little outfits for everyone to see. I made you put on a skimpy outfit to wear. A short skirt with some high heels, all you could think about was those huge cocks fucking you so hard up your pussy. You are going to be and obedient whore for me. Whatever I say goes. I showed you the video of you taking all of those huge cocks and wearing those skimpy outfits. You begged your phone dominatrix not to tell your wife. “Please! Please don’t tell her what a huge cock loving sissy whore I am.” I heard you say. You begged me not to tell and I told you that in exchange for my silence you would have to do whatever it is that I say, under my command you strip down to reveal you tiny clitty. I laughed uncontrollable. “What is that?” I cackled at you and introduced you to all of my friends. My friends had huge BBC’s that I wanted to shove deep inside you. They smirked at your small clitty and I informed you that this was only the beginning of your sissy girl training.