Tag: Sissy training

Best Sissy Trainer Loves New Toys

Best Sissy TrainerI see I have a new brat to tame tonight don’t I? Your pretty girlfriend sent you in here right? Oh yes, she’s lovely indeed! I got to have some fun with her this afternoon and sucked her pussy as she told me all about you! hahaha! Quite the screamer too. She said you were nothing but a little pansy bitch just waiting to become who you really are. So, are you ready to become the sissy you deserve to be so you can stop disappointing that sexy girl of yours? Get on your knees! Crawl naked on the floor for me on all floors! Those pink panties are laid out just for you little faggot. Try them on and come out to meet some new friends!

Punishing My Sissy Cum Slave

Sissy pantiesMy sissy slut Cassidy pissed me off the other day. She disobeyed her mistress and removed her plug before I gave her permission. To make matters worse she didn’t even use her mouth to clean it like I like all my sissies to do. She was nervous her wife might find out about it. Just for that I locked her little clitty up in an extra small cock cage and made her wear her pink frilly sissy panties home to her wife. I also put my inflatable ass spreader in her and filled it all the way up. For good measure, I made her suck on a cum ice cube on the way home too. I want her breath to smell of fresh cum when she goes home to kiss her wife.  I hate it when I have to punish my cum sluts but this mistress doesn’t take kindly to disobedience. This little sissy will learn to understand that her wife is not the one she needs to be afraid of. 

 

Joy To The World!

Sissy Training

The end of the year is the busiest time for a sissy slut trainer like me! I talk with all my sissies daily about their holiday party outfits, gift choices and make up combinations. I even spend time talking about cock sucking quotas. That’s right, my sissies are extra giving during the holidays, they are excited to get a cock sucking quota of at least ten fat cocks a week! They linger at the gym, at family gatherings, after work parties and at gloryholes waiting for their opportunity to suck a mean dick and tell me about it later, they know I live for the dirty details. Why do they do it? Simply because they know that Mistress Raine wants her sissies slurping and deep throating all December long to bring joy to the world!

Sissy training involves me

Sissy training

You know sissy training is my jam, and I love it so much because I can put whatever kind of twist on it I desire. I’m the girl you want to learn from and to be honest I have quite the lessons to show you. Im going, to be honest. Porn is a godsend. It will show you what men love more than anything, and in my eyes, that’s pussies and boobs. Naturally, you don’t have a pussy, but you have an ass pussy, and that will do. Im going to enhance your fake boobies and help you dress to impress. iM GOing to make all the straight men give you a shot. Im a pro like that, and you will see plenty of cock for your sissy holes.

Get Dressed

 

mistress phone sex

Time for a pool party baby. I am having some friends over and you and my hubby are going to be the entertainment and pool faggots. Go on into the room and I have laid out the sweetest little slutty maid outfit for you. A hot short, pleated skirt with matching corset, a black thong, breastplate and black thigh highs and heels. Oh, and I put a pretty Christmas tree butt plug beside it too. Make sure you push that all the way into your pussy babe. Then put on your lip gloss and get out here.

Oh, my look at you two. Perfect femboys. Now get to work. You know what to do. Grab your trays and make sure everyone gets their drinks and appetizers and whatever else they want too. Oh, and don’t forget the poppers, you know how much my friends love those. Come closer. I whisper in your ear that your mouths and man pussies are available too. Don’t disappoint me and don’t embarrass me. As I sit back and sip my drink I marvel at my party. Then I see you both performing lovely.

My hubby on his knees sucking a big black cock, which he loves. Practically worshiping it. I can only imagine the little clitty leakage occurring as he devours it. You? Well, you are bent over the table. Skirt pulled up and taking a big thick dick in your tight pussy as you also suck a cock in your mouth. You both look marvelous. I could use another faggot for my party. Do you think you have what it takes?

BBC Sissy Trainer Heaven

BBC sissy trainer My little sissy cum sluts are trained to be the perfect BBC cum whores just like their sexy Mistress. I put my sissy on a leash and caged up his tiny clitty. Mistress Heaven has a surprise for this sissy slut. “I have a surprise for you that I know you’re gonna love my beautiful sissy,” I told her. Before she could ask any questions, I commanded that she open her big mouth nice and wide. I completed her slutty leather outfit with a new toy, a slave punishment mouth gag with nipple clamps. Her pretty red lips looked so plump and sexy in her new toy. “Assume the position” I instructed. My obedient sissy slut bent down and got on all fours. I pulled out my next surprise, a huge hollow tunnel butt plug. I inserted it into her tight sissy asshole. She whined and tensed up. “You better get used to the feeling of having your tight little man pussy stretched open babe. All good sissy pussies are always wide open and ready to be used at any given moment.” That’s when I brought in my final surprise a BBC friend of mine who just happens to love breaking in new sissy sluts. “You’re going to be the best sissy and lick my sweet pussy while my friend fucks your boy pussy with his giant black cock,” I smiled. I spread my legs for my sissy as my friend rammed his cock into my sissy’s hollow asshole. My pretty sissy obeyed my instructions while her tight ass got used and fucked. She sucked my wet pussy as my friend’s massive cock filled her juicy, stretched out man pussy with hot sticky BBC nut sauce. “Let my beautiful cum whore clean you all up, friend,” I told him. My friend nodded and pulled his hard, shiny cock from my sissy’s wet asshole. He removed the mouth gag and replaced it with his BBC. “I want that dick all cleaned up, sissy,” I directed. “You’re going to be a BBC pro by the time I’m all finished with you,” I smirked.

The Best Sissy Trainer for Christmas

best sissy trainerGive yourself the best sissy trainer for Christmas. The holidays are right around the corner, and you deserve something for yourself right? It can even be our secret. I have plenty of closeted sissy boys. Most of my sissy callers and clients are married with respectable jobs where imagine is important. What happens with us during our time together, stays between us. Unless you piss me off of course. I have a private sissy client I see in real-time. I have known him for over a decade. He was my divorce attorney. One of the best in the industry. I saw something in him. He knew what I did. At that time in my life, I was not doing sissy phone sex yet. I was a dominatrix. My ex-husband was trying to blackmail me into getting custody of our offspring. I knew if he got custody, he would send our sissy boys to some alternative conditioning school where they could not be themselves, so I hired the best lawyer. He became one of my first sissies. We have had a decade relationship, but he recently tried to black mail me into free training. Like that shit is going to fly. He had no power over me. Being a sissy trainer is not illegal. My sons are trans, and young teen boys, no one can take them away from me. He was trying to black mail the wrong woman. I have nothing to lose, but he has everything to lose. I sent him an email of him in frilly pink dresses and bonnets getting spanked and sucking cock. Over 10 years together, I had a ton of photos. I told him one push of a button and I would send them to his firm, the American Bar association and his wife. I am severing my relationship with him too. I mean you cannot blackmail woman who is providing you with sissy training and not expect her not to fight back. I am a nurturing and sweet sissy trainer, until you cross a line. Then you will pray you had never met me.

Sadistic Fucking For A Pain Slut Like You

Sissy training

Men come to me for some sadistic fucking. I know they love cock and ball torture so I tie their little cock and balls up to his hands.  I will use some metal weight clamps to clamp to your tiny balls and see how far down I can stretch them. Your cock loves it when I hurt it. I will stick some pins, one on each side on your cock starting at the base. When I get to the head your cock, I will push one down your hole. While you stand there pinned up, I will paddle you with my big wooden paddled until your ass is ready and swollen. If you don’t flinch, I will pull the pin from your hole out and bend you over. Ill shove my big metal dildo up your ass and rough fuck you until you bleed out. You’ll beg for me to let you cum and I will take my time to pull every pin out of your cock as I pound you until I finally let you cum hard from that little bloody dick.  

Xmas List 4 Mistress Phone sex

mistress phone sex My Christmas list is huge this year, thanks to all the mistress phone sex fun I have had with my pay piggies. And I can’t help but wonder what is on your secret Santa list? Darling, what would make you feel like the pretty slutty sissy you are. Maybe a forbidden pair of heels to stash in your closet while wifey poo is away? How about some silk lingerie that fits you just right? You deserve pretty underthings that form fit and accent your assets! Perhaps you can buy your wife some makeup that’s just a little too bold for her taste, and you get to “return” it for her, she gets something new and your make-up is all for you! While we are on the subject, I know you and your wife are different sizes, and you really need to stop stealing your teenage daughters’ clothes. My command for you is to buy yourself some brand new frilly sissy panties! Take your time and shop around for the best and get yourself at least one pair of expensive Delicate panties, Oh throw your wife a couple pairs in the cart too. A good clever cover up if there was ever one! Just make sure the ones you pick out are what you truly desire! If you know me, I’m all about making you into what you were meant to be, by any underhanded means possible! Hopefully you will be all dolled up and ready to play in your perfect sissy outfit for me, one you picked out! If you need help, Mistress Zoey is right here for you!

Sissy Fun With 2 Mistresses

Sissy girl training Mistress Gypsy and I always have so much fun playing with our beautiful sissy slut TJ. This Christmas we have something special planned for bringing in the new year. Mistress Gypsy got a brand new, purple, double-sided strap-on and we’re going to dress our sissy cum slut up real nice and pretty. Then we’re going to do a sexy homage to Sweet Gwendoline photo shoot starring our favorite girl! We also picked out a gorgeous deluxe pink chastity cage for her little clitty. It’s going to be so sexy watching Mistress Gypsy deepstroak sissy TJ’s tight man pussy while the other side of that purple strap-on pushes deeper inside her cunt. I’m going to love seeing our sissy slut with her pink lipstick all smeared from licking and scooping all the creampie out my slippery kitty while she takes that purple dong right in her fuckhole. We’ll fuck our sexy slut until her clitty leaks yummy cummy through her cage. Then we’ll make her clean that ten inch purple dong on both ends. She’s the perfect sissy cum eater to dress up real pretty and play with. We will train you to be an obedient, perfect, cum-guzzling sissy slut too.

Taboo phone chat