Category: Sissy phone sex

The Gift That Keeps Giving!

Sissy Phone Sex

I can’t wait to spoil my sissy sluts over the holidays! All my little sissies are clamoring to book long shopping sessions and sissy training calls with their favorite sissy trainer Mistress Raine. We talk for hours about clothes, shoes, styling and gifts! My sissies are all in perfect condition to suck and fuck and ring in the new year riding a cock! It makes my heart so warm to help my bimbos to make a great impression on the holidays, I know how important it is for my sluts to spoil themselves and their favorite people! Give yourself the gift of an hour with the best sissy trainer around! Quality time with Mistress Raine is the gift that keeps on giving through the holidays!

She Is So Obedient

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I had the most perfect sissy call the other day. So obedient and so submissive. Willing to do anything and everything with just my command. Allowing me to dress her anyway I see fit. Never offering her opinion for anything. Understand that she is to please me without question. Dressing in frilly sissy skirts and hot sexy heels and stockings. A big thick butt plug pushed deep inside her pussy. Her little clitty contained with the smallest of cages. Teasing and tormenting her with her favorite shemale porn. Watching the grimace on her face as the cage prongs stick to her swelling clitty. Trying to contain her excitement but failing. Small droplets of precum leak and I laugh. That will get you punished you faggot. She calmly walks over and bends over my knee, pulling her panties down and exposing the jeweled butt plug. I am not even going to remove it for the punishment. I admire her pale white cheeks knowing they will soon be a crimson red. I start the paddling. One cheek, then the next cheek. Back and forth over and over. She never asks me to stop. Her ass is bright red with white patches. Her clitty is swollen and painful as I reach my hand back for the final blow.

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!

He Needed a BBC Sissy Trainer

I am a bbc sissy trainer and so is my daughter. She is 18 now and wants to be a sissy trainer and dominatrix like her sexy mommy. She has shared some of my BBC lovers with me over the years. And I have shared quite a few of her black boyfriends with her over the years. Last night, one of her black boyfriends was over when I was training a sissy. This sissy has never expressed interest in black cock or any cock. This sissy just wants to dress up and be my sissy maid. That all changed when my sissy went upstairs to use the bathroom and walked by my daughter’s room. She did not have the door completely shut and my sissy bitch saw her sucking on her boyfriend’s big black cock. My sissy came back downstairs and started drilling me about the guy upstairs. His clit stick was bulging in his nylon panties. I excused myself for a moment and came back with my black suction cup dildo. My daughter’s boyfriend is not into guys at all. But I know plenty of black men who think any port in a storm will do. I texted one of them that I had a sissy bitch who needed stuffed. While I introduced my sissy to my black dildo, she came alive. She was no longer interested in being a sissy maid. She wanted to be a black cock sissy. Well, she was in the best company because I am the best sissy trainer for BBC faggots. She sucked on my black dildo for awhile before she asked for the real thing. That was on its way. My black lover arrived 20 minutes later and broke in my sissy’s ass with the real thing. Nothing feels better than a real BBC in a sissy’s ass. Or my ass either. And just like that as sissy went from a maid to a bbc sissy faggot.

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!

Mistress phone sex with Miss Remi

mistress phone sex

 

Mistress phone sex is my favorite way to have fun! I love telling stories about what I do with my sissy bitches. Last night, one of my favorite little, sissy sluts came over to see me for some kinky play time with his favorite mistress. I had a date planned but this sissy bitch is such a good cock sucker and such a cum thirsty, little whore that I just had to use his slutty mouth. I had him suck and stroke my date’s fat cock until it was rock hard and throbbing for me. I got so turned on watching his throat getting fucked so hard! He watched me ride that massive, fat fuck rod until I drained my date’s balls into my hot cunnie. My little cum slut  was begging me to lick up that creamy load but I made him wait. I wanted to feel that creampie drip out of my hot pussy while he cleaned my date’s cock off with his dirty whore mouth. I even got a hot video of my cum slut, sissy bitch licking my pussy clean while my date pumped him full of cum! I’m going to be watching that while I wait on my phone to ring.

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?

Mistress Phone Sex Cum Eating Training

Something I always wanted a guy to do for me was to eat his own cum. I love cum eating phone sex calls. Well, I am perverse to know that I could really make a guy eat his own seed. Like a straight guy. You will be all worked up and excited and I would force you to lick that semen up off your fingers before the feeling goes away. You will do it for me. You will be my submissive cum eater and I will be your Mistress. Lay back and listen to the sound of my voice. I will taunt and tease that jizz from your sexual member. You will have to instantly put your fingers to your mouth and eat that semen. This is how you prove to me that you are my slave. A good slave does what his Mistress wants. That is the power I have. I make you eat your cum. If you don’t follow through you will get two more chances. You fail all three and I am not going to be bothered with you anymore. So that is my first requirement for my slaves. I may request you buy a dildo or a cage and we will then carry on from there. But first things first. The cum eating initiation into servitude to me.

Mistress Phone sex

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.

Sissy Adult Diaper Lover

sissy phone sexI have the cutest little sissy who is an adult diaper lover too! I have been working on that part of him that needs to be nurtured and cared for and wearing a big stinky diaper for me. I call that a two-for-one when I get a sissy who needs to be humiliated in a diaper. That’s a two-part humiliation my loves! I just love feminizing a man all the way down until he is now a little girl in a fancy pink on it and a little pink bloomers with a big bottle full of cum juice right in his little cutie pie lips or should I say her lips? And that little dicky poo is just a cute little clitty tucked away in a diaper. And being a sissy trainer / Mommy I know that it’s important for my sissy to get as much nourishment as possible! Cum and cock and mommys milk provide that! Especially an ABDL diaper loving sissy little girl! And my boyfriend has a big black cock that he doesn’t mind using as a bottle so that my sissy can drink right from the tap! Are you supposed to sissy who loves diapers and needs to be humiliated?