Category: Sissy humiliation training

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…..

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.

I’ll Be Your BBC Sissy Trainer Today

BBC Sissy Trainer

I knew what I was doing when I told my older brother he had to get on his knees in that tiny dress and suck of the school quarter back. A real BBC with a long hard 12 inch cock. I laughed as he did it and i took pictures and recorded it so he would know I owned him. He was never escaping me now. I showed him the video and made him tell our parents he was a fag and loved cock unless he wanted me to show them the videos. I exposed him at school by starting a rumor that he wore girly panties and made him wear a pink lace thong. Then convinced some boys make him show them his panties. I laughed so hard when they bent him over and fucked him like the sissy bitch he was. of course I recorded all of it.  When he refused to wear an outfit or do what I wanted I promised to show the church elders that always quieted him up. He knew he was a sissy and the next goal was to get him some real tits so he could be the perfect blonde bimbo whore. It makes me smile.

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.

AW you and your sissy panties

sissy panties

 

Pulling on his sissy panties giving him a nice little wedgie in front of all my girlfriends. We loved having him be our little servant, making him lick the cum off our sexy toes. We had him completely dressed up too, head to toe. 

He was the perfect for our little party and perfect for our entertainment. Each of us taking turn squatting over his pathetic sissy face and pushing loads of cum into his pathetic mouth. 

Even forcing them to satisfy my bbc besties using their fuck holes however their dicks needed too. 

 

My Brother Is Myy BBC Sucking Sissy Whore!

Sissy Hypno Training

I love hypno training my big brother that’s how I get him to be my perfect cock sucking sissy maid. I have him blow BBC for me and get them ready to fuck me and then I tell him to eat the cum out of my creamy teen pussy. He loves how it tastes and has started begging me for it. He really enjoys being a mindless whore and having me tell him to dress up like a French maid and bring in more men for him to suck off.  He loves when I put him under my spell and take away all choice and make him be the whore he’s always wanted to be. I make him take it up the ass with big fat cocks and make him show off his big sexy clit to all the men before they fuck his tight puckered boy pussy. he begs them to make him an anal gape slut and to breed him. He wants to be used and abused by all the bulls that I invite over and I must admit I love seeing him get fucked and watching all the cum drip out of his gaping boy pussy when their done.

Forced feminization with Tanya

Forced feminization

 

Forced Feminization just might be my favorite thing to do to you. Nothing brings me more joy than embarrassing you with some fishnets that are too tight for your manly legs and leather black heels you stumble around in. I love making you wear a little maid outfit just so you know you are beneath me. You work for me bitch, and you do as I say. Now take your little servant ass, sit on the floor in front of me, and start sucking on my toes. I bet you love how Mistress Tanya tastes. I’m going to put on my biggest strap-on. While I’m getting ready to make you a sissy, instruct you to put on mascara and lipstick. As I am choking you with this strap-on, I want to watch the tears run down your face as I make you gasp for air. I want to see you look like a sluty ugly whore with lipstick smeared all over your face. You make a beautifully trashy-looking sissy slave to me. You take orders so well. I think I should face fuck you real hard like the good little whore you are.