Tag: Best sissy trainer

Online Sissy Training Blends Well With Mommy Fantasies

online sissy trainingObviously, my specialty is online sissy training. But I do a few other things too like mommy, cuckold and adult baby play too. Sometimes I get to combine a few different fetishes. But whatever a man’s fantasy might be, I am a dominant woman, so I’m always in charge and in control.

Recently, I got to be a caller’s dominant mommy. And I turned him into my cuckold and sissy boy too. And let me tell you how much we enjoyed this role play. A smart mommy knows when her son might be a little different from the other boys. I experienced this with my own two sons. But this boy played in my lingerie and spied on mommy with her big black lovers often.

But I knew he seemed different. He liked the feel of my lingerie more than the scent of my pussy on the lingerie. And he enjoyed looking at those big black dicks more than he enjoyed watching the fucking. So, I decided he needed a little femboy training. And some black cock training too. And in that moment my son became my sissy boy and my cuckold.

A Sissy Trainer Wears Many Hats

I dressed my son up in a pink little baby doll nightgown with some matching pink panties that covered his little nub. And I slipped him into some little cable knee high socks too. But the first thing I had him do while looking so feminine and pretty was suck on my black cock lover’s massive shaft. I had to help my sissy boy suck that cock, so I palmed the back of her head like a basketball and shoved her down balls deep. Sometimes the best way to learn to take a cock is by force.

I am a dominant woman and a BBC sissy trainer. So, I know how to get you to take that massive black cock, one way or another. My newfound sissy boy polished that knob, fluffed it for mommy and then guided it right into mommy ‘s wet pussy. It felt important for her to watch me. Sometimes watching best teaches a sissy how to be a good black cock faggot.

Eventually, my boy got to clean up my pussy with all that black cock spunk in it. And I swear, all that extra protein helped feminize my son even further. I found it to be a hot role play. And so did my caller. Sometimes all a sissy has is his imagination. But with the right sissy trainer sometimes those fantasies can seem super real.

Drenching his sissy panties

Sissy panties

Covering his sissy panties in loads of cum just for him to wear all day. And of course, adding my own cum to it which is my absolute favorite standing right over them and squirting right onto them. I made him do a little fashion show in a bunch of little outfits for me and my friends. Then being used like a good little sissy slut, his little clitty was so horny and leaking from excitement he wanted me to touch him so bad. 

I teased him for who even knows how long, his little clitty was throbbing his legs shaking and him just so desperate to see what I would do next to him. Spanking him nice and hard and letting him squirm while I teased his holes. When i finally started stretching him his clitty couldn’t hold it in and he came all over his little sissy panties. 

BBC bad boy get’s his man pussy stretched and enslaved

Femboy training

Shame on you, you’ve been so bad, punishment is the only answer. You’ve been such a naughty little fuck boy. And it’s not ok darling! You’ve been whimpering, crying, sniffling, making sissy faggot faces while I’ve got this 13inch BBC rubber beast up your ass. Take it like the pathetic shit head you are and if I hear one little whimper I’ll humiliate you even more!

I like my slaves dressed in hot wear, cutie little one’s clothes including panties, bra and pigtails. That’s what y’all are, little bitches so dressing you up like one is appropriate. Make up is required in my dress up party as well, mascara, cat eyes and hot read lipstick honey.

I have friends, family and couples that’ll rob you of any dignity you thought you had, put you on your knees, bend your ass over a counter, or get down on your stomach. I want you in all the pathetic positions Ms. Jackie demands you be in. I’d love to flip that skirt up and lets shred those panties your in, stuff up your ass crack and make you scream and whimper even more. I’d love to do this more if we had an audience or a camera so we can can have you watch it back, laughing and giggling at how worthless you look, no body wants you including your wife.

Sissy humiliation includes many things but we gotta keep those cheeks of yours packed and your throat gagged. Sucking my brother’s cock while my daddy is balls deep in you, cleaning my gorgeous tight twat after a nice fuck, or even sucking down on some balls while that dick is deep inside me. I want my precious kitty purring by the time your done cleaning every drop of milky sensation that filled my tiny holes. After that is cock cleaning time, on your knees with a foot on your inverted cock, your gonna suck that beast till it glistens.

Oh all the options for my sissy faggot slave boys, I could go on…..

Best Sissy Trainer Teaches Proper Cock Sucking Etiquette

Best Sissy TrainerAs your Best Sissy Trainer, it is my job to teach you how to suck cock properly. Now, I understand you have a cock, so you know what it feels like. But you need to know how to take a more feminine approach to sucking cock. How are you gonna be the best little sissy faggot fuck ever, if you don’t know how to suck cock the way a woman would?

Look at things from His point of view. Think of how hot it would be to look down and see a nasty bitch all decked out, sexy ass makeup, whore lipstick, and sexy nylons or stockings. That’s what he wants to see. A bitch like that on her knees worshipping his cock, making love to it and fucking it with her mouth. All dressed up and ready to give head like the little cum slut you are!

It Makes me Proud to Turn You Out

You come to me because you want to be like me, right?? You are like my biggest fucking fan, so head my words. We will have you bouncing that cutie patootie prison wallet off a cock in no time. Don’t be afraid to get nasty. If you come to me…..babyyy, I am gonna make you gag and choke on that big cock. Ill make you use your throat to fuck it. Fuck, if he’s really big we can even talk about unhinging your jaw to fit him.

But the absolute most important part of being a nasty little chicken head, is you can’t forget about his balls. They need to be licked and sucked and spit on. Pull those mutherfuckers down, make weight on them. Then use your neck. they don’t call it Chickenheading, and giving that Becky for nothing. You really want to impress him, swallow his dick and take his balls in your mouth.

 

 

Tanya’s Sissy Panties Look Good on You!

sissy panties

 

Tanya’s Sissy Panties look amazing on you. Your tiny, pathetic cock fits perfectly into the panties. If I didn’t know better, I would’ve thought you had nothing down there! And look at your flat butt cheeks sticking out from the thong. What a tragic excuse of a man. 

You look real pretty wearing not only my panties but my stockings, heels, and a long blonde wig. You would’ve made a beautiful woman, shame god gave you that tiny twig in between your legs. 

I want to invite all my friends over to watch me fuck you with my biggest strap-on, since I know you like to be treated like a trashy slut. We ALL would burst out in laughter as you moan and squirm with pleasure. I can dress a grown man up like my little fuck doll and have him begging for mercy on his knees in no time. You want to look like a prissy bitch, you will get treated like a prissy bitch.

I am going to fuck you until you are physically and emotionally exhausted, like the good little Sissy you are. 

 

You cum to the best sissy trainer to get turned into the hottest trick bitch

Femboy training

I love all you nasty pathetic little sissy fucks but lately my favorite one’s have been those weak men with inverted non working little pussy cocks. Your wife doesn’t want you, just that money you got and in fact, she makes fun of you and has moved on, fucking other men but not just any men, she loves that BBC. Your torn, feminine and weak since your still married to this crazy nut sex hungry bitch and have cum to me to help you realize your new role in life, get used to it darling. Ms. Jackie’s here to help you love and not to worry.

I start my sissy training with beautiful makeup, eyes, hair, skin. I need you to look like a cute bitch that’s craving and just asking to get rammed up the ass. I think pic tails is perfect for you. Little one, barely legal bitch! Cute little skirt, tight panties and knee high socks, your sooo ready get your man pussy popped!

My other sissy faggot boys will help you out, bend over bitch. Slowly and steady we ram our introduction 10 inch in. Not to worry we all spit on it to lube you up, so spread those legs honey! I’m pulling your little pink hello kitty panties up your ass as he smashed and stretches your oozy drippy sloppy wet baby pussy hole. Your moaning and whimpering so my rule, “Crying means harder little bitch”. Your now shivering and quivering as we’re all standing around you. Pounding and packing your fecal fudge hole.

Humiliation at its best.

In walks your wife, giggling laughing as your on all fours looking like a girly slutty sissy whore. “Well well well, I’m not surprised”. Your eyes light up, humiliated but turned the fuck on. I demand you to rock your tight ass back and forth, feeling this girthy rubber mother of a god BBC dick up to it’s fullest. Your wife watches as your soaked panties are leaking pre cum down your legs. She spread her legs in her skirt, exposing and showing you her freshly shaved pussy swollen after fucked snatch, that you’ll never fuck again. This makes you explode like a little bitch teen queen, living the new life just meant for you.

Sissy humiliation training

 


I love a good lilttle bitch boy I can just whip and humiliate. When I get a nice little twink in sissy humiliation training, it gets my pussy so wet knowing how I am going to use and abuse that my new slave. My newest bitch boy lives to be under my leather boot. whipping sessions are my favorite.

I smack his tight ass so many times with my cute pink whip he can no longer feel his worthless ass cheeks when he sits down, of course he spends most of his time on his Knees begging and bowing to mommy, so he has no need for his worthless busy cheeks. He knows his place; momma needs that check from her little weeny boy and he needs to pay homage and beg crawl and clean. Now that’s a Good boy. Get to work.

Forced Sissy Training is The Best for New Recruits

When it comes to new recruits craving for the big dick, then sometimes forced sissy training is in store. As a Mistress I will not shy away from forcing my perverts and sissy girl wannabes. And what I force them into is what they crave. Obviously that is being the best little whores they can be.

Forced Sissy Training is The Best for New Recruits

Some of you come to me already in those sissy girl panties. Now this really demonstrates to me how ready you are. At least it shows me you understand you are to wear panties. Next thing you will need is that dildo or butt plug. Once you have those things and we start training those lips is best. 

Alternatively, we can train that sweet little bitch cunt. And my sissy phone sex line is the perfect place to explore. Often times we start with some butt plugs of various sizes. Additionally, perhaps a nice dildo with a suction cup. Overall these are great for you. The suction dildos you can back up on it. Just like you will for that real cock.

Additionally some of you make it a good effort to just go for it with the real thing. And this I give you props. Now when there is an adult theatre or glory hole/ sex shop near by there should be no excuse. 

Finally the need for real dick is strong and you just need to get yourself on grinder or one backpage or any other such site for finding the dick to please. Be a good sissy for your Mistress phone sex trainer and do a good job. I expect pictures. Either of you dressed, in your panties no face, or being a good slut and sucking off that dick. 

At least when you discover the need to be a sissy faggot you have options and a Mistress here to assist you.

Forced sissy training

BBC Sissy Trainer Tanya

BCC Sissy Trainer

BBC sissy trainer is the skill I’m the best at. I love taking a pathetic little bastard like yourself and forcing them to experience what it’s like to be a real sissy bitch. 

First, I’ll dress you up nice and pretty. Black thigh-high stockings, pointy high heels, and a tiny little skirt so short your pathetic little dick can’t even peek out. 

Then I’ll slide into my biggest, black strap-on and bend you over. I’ll tease your tight little lubed-up asshole until you are begging for this BBC. 

I’ll have to stuff your mouth since it’s your first time, because I know you’ll be screaming when I cram it in you. I’ll go slow at first but start to go faster once I start to hear you whimper and beg for more. I’ll keep banging that ass and jerking you off from behind, getting you close to cumming. I want to hear your moan like the lady you are. Take this dick, you worthless, useless whore. You deserve this ass pounding.  

New pathetic sissy crawls his way to me begging to be pegged

Sissy slave training

You called me tonight begging to be pegged. You’re a newby pathetic worthless faggot sissy fuck who’s been referred to me because you love to play dress up. My specialty is dress up. From dresses to makeup, hair and nails, I have all you pathetic princess’s covered.

However I was slightly impressed with this my new little sissy fuck. Professionally done up. Cute skirt with matching panties, a and his cock and balls locked up in a golden chastity. My gaping who began to cream as you crawled on all fours and handed me the key. “Will you be my mistress Ms. Jackie?” you asked like a pitiful pain in the ass. Eyes full of fear yet so feminine and pure.

There’s always as surprise on the other end when your my sissy slave!

You’ve lost control of your shrunken balls which are locked up too. Taking estrogen to make yourself feminine to fulfill your ultimate fantasy of cucking for your wife, sucking her man’s cock every night as your little tit’s are growing in.  your family is aware of your sick side life and fantasy and hold the other key to your locked up cock. This is your way of life and you’ve accepted the reality that your officially owned.

I’m honored to humiliate you, sparkling new, glistening out of the box. A fresh new slave I can abuse, violate, and toss to the side. I prefer  starting with a 10 incher in the manny pussy with the controller in my hand. I’ve got you bent over and your such a good sport,already winning hot wet mistress pussy points. I turn that shit up to ten and watch your ass jiggle and sizzle, so hot it’s steaming.

With a smile on your face you take it well and I’m pleasantly impressed.  I spread you out some more, spread some lube, smack your panty wearing ass and welcoming you to my new faggot fuck crew. Your officially apart of a family of cucks and always making sure Mistress Jackie’s cookie is poppin and fresh to death.