Category: Sissy phone chat

Be My Cock Pleasing Protege!

Mistress Phone Sex

I’m in the mood to turn a curious sissy into a full blown faggot! I’ve been dreadfully bored this week and I need a closet bound queer to mold into the perfect little cock pleasing sissy slut. It is no easy feat turning a curious boy into a glorious cock queen like me but I’m always up for a challenge! First we start by watching some beautiful tranny porn, only the filthiest will do as my sissy will need to know just what I’m expecting him to turn into. Then we will work on the look, every sissy needs some good styling and product recommendations to make them shine. Finally we will work on pleasing a cock together, the ultimate task, if you can share a cock with Mistress Raine, you are already winning the sissy slut game!

I have a pussy and you don’t

sissy phone sex

I have a secret weapon that makes these sissies cry. Look, I know the ultimate dream is to be like me. A cute young spinner who can get all the delicious cocks in the world. The problem with that is you are a natural-born male. Shocking how I tell you the truth. See, most the trainers will have you think you are a “real woman” the thing with that is that it is pretty misleading and a big fat lie! Yes, I am going to be mean. You wish you had a pussy. The sad part is even if you bought a fleshy pink cunt and had the modifications and surgeries, don’t be a ” woman,” let me tell you, and you’re not a woman. You will never have a natural-born pussy. You can never get pregnant by semen. It might hurt to hear the truth, but you will never be me. Once you realize the reality, which you know all too well already, you will face the fact that you are only a man in drag that will be used to pay up and add to my funds. You want  sissy phone sex huh? now this is the pinacle of sps.

Sissy Cums in Lockup

mistress phone sex

Spread that fucking as apart so mistress can get a good view while she fucks your sissy ass. I got you a new chastity so I can see your little clitty in cage while you penetrate that man pussy for me. Before I give you this big veiny strappy that I have I want to see you fuck your pink man pussy for me. Lay on your side like a slutty bitch and put this dildo all the way in until the balls hit your little grape nuts. “These are tiny and pathetic” I say in disgust as I flick your quivering nuts. Your tiny dickie is already dripping from the dildo plugging your pussy, so I snatch it out of your hand and shove it in your mouth! “You only cum for Mistress!” I remind you as I shove my thick 11 in cock inside you. I’m so deep in your twat I can feel your tummy rumbling! Youre such a size queen I should’ve known thrusting this big dick in your twat would make you squirt! Even in lockup you can’t control yourself from leaking cunt juice down your little berries and thighs!

Sissy phone sessions

sissy phone

Get ready for some wild sissy phone fun. I’m going to use terms that will be hypnotic. You will be my sissy slut who will do whatever I say. Once you do what you want, you will move on to the next level. Sissy tasks tend to be all about what makes your mistress happy. What makes me happy is a fluffer and a vacuum cleaner. Go ahead and suck a cock till it’s hard, and clean up the effect. Take notes and learn what will make you the best sissy slut.

It is an honor for you to learn the best tricks and tips for becoming the best cock sucker and the number deepthroater. you are so lucky to enjoy training from the best red headed goddess around.

Sissy Girl Training

sissy girl trainingLooking for sissy girl training? I love to train sissies. I am a mommy and a nurturing sissy trainer. I treat my sissies like my daughters. I dress them up frilly and pretty. And I teach them all the things they need to know to please men. I have a new real-time sissy. She found me through my daughter. He used to go to school with my daughter, but he dropped out before graduating because he was bullied. He was a femme boy then. Still is, but now he wants to transform. He plans on becoming a T-girl. She is saving up for a boob job, but in the meantime wants to work the truck stops and glory holes for money. My daughter brought her former schoolmate to me because she knew I was the best sissy trainer for the job. She was right too. I know how to turn a boy into a cock sucking princess. A few days with me as her trainer, Mark became Michelle. I did her makeup. I put her in a wig and some very pink and frilly clothes. I showed her how to walk like a woman. I showed her how to suck cock like one too. Such a pretty girl afterwards. She is a natural cock sucker. Honestly, one of the best I have trained to date. She took my big black dildo balls deep after the third try. It is 12 inches long. I knew where to get her maximum money for her skill set. The truck stop is full of black truckers in need of an eager mouth to drain their balls. When she became Michelle, she wanted big black cocks. So many sissies do. I am a BBC sissy trainer because I am a BBC slut. The bigger the better if you ask me. Same for Michelle. I took her to the truck stop last night and she made a couple thousand dollars just sucking on big black dicks. She will have her money for her boobs in no time with me as her trainer.

I Love Phone Domination

phone dominationI love phone domination. I can be a whips and chains dominatrix, but I prefer to be a nurturing domme. The kind that pegs your ass, dresses you up and teaches you to suck cock. I am a bad ass bitch. I have softened over the years since I became a mother. I am more nurturing now. A caller asked me how I knew I was dominant. My awaking was in college. I was an alternative girl. I was part of the Goth community, leaning more towards the steampunk clique. I took no shit from anyone, especially men. I met a much older professor when I was 19 and we had an affair that lasted 15 years, even after I married and became a mother. It is not the kind of affair you think. I was his mistress but not as in lover, as in owner. He had a kink lifestyle he had to keep hidden. In the early 2000’s he paid me $500 a week to peg and whip him. I did other things too like flogging and face sitting. My dorm roommate was slaving at Walmart for minimum wage. She worked 30 hours a week for less than $200 a week. I worked like 8 hours a week and was paid cash, under the table. My professor liked my look. He trained me to be a phone dominatrix. I was dominant by nature, but I had no clue yet about the BDSM lifestyle. Meeting him changed my life. Based on my experiences with him, I was able to add more clients. Before long, I was 23 making over $100,000 grand a year as a dominatrix. Now, here I am training sissies because all sissy trainers are bad ass bitches. Not all submissive men are sissies, but all sissies are submissive. They need a sissy trainer who is not afraid to train then or punish them either. I still have a few BDSM clients that I see in their homes, but I am more or a sissy trainer these days. Sissy training begins with a phone call.

Mistress Raine Is Proud Of YOU!

BBC Sissy Trainer

When I hear my little sissies squirt all over themselves from our calls it makes my kitty purr! I love talking dirty with my sissy sluts all night long! I love hearing about all the perverted things my sissies like to do like sucking cock at gangbangs and getting cum dumped like whores. When my sissies tell me about all the cock they have taken or even the cocks they dream about my little pussy gets so wet. Mistress Raine craves all those sissy slut stories and likes hearing about anything filthy that her sluts get up to while they are out in the world of cock. If you have a slutty story you need to tell me, give me a call and I’ll tell you how proud I am of your slutty sissy behavior!

Best Black Sissy Trainer

best sissy trainer

I’m the best sissy trainer because I do not hold back for a little dick motherfucker! I let these little dick fuckers know that I am their Goddess and they only time they can come near my twat is when they are licking th cum out of it. Other than that, I want to see those puckered pink man pussies in the air so mistress can spank them. I like to paddle a sissy ass until its hot and red so it hurts even more when I drop my dick in them! My favorite dick to use on them actually belongs to my black buck Tyrell. He has a 14-inch cock that he loves to use on my little dick lovers when I do not feel like they deserve my cock. He can fuck a pansy pussy for hours but first he has to make goddess cum. While he has my legs pinned back I expect to have two sissy mouths on my clit and one on his balls. They need to milk his black rod of the biggest fucking load right into my heavenly twat! Once my pretty slit is dripping cum Tyrell will pick who can lick it out of my cunt and who can get a load straight from the source. What will you do to ensure he chooses you?

we need to have a meeting

sissy phone

As part of my sissy phone sessions, I love to have meetings and will expect nothing but the best from my sissies. I want to make sure you are intelligent and working smart. When you are jumping into the world of sissy life, you have to know you will not be the only person around who has ever thought of being sissified. You must come through with the work. I want to make sure you are sucking so many cocks and taking lots of cum. I don’t have time for games and will put you to the test. I will make sure you outdo yourself and show me you were born to be a sissy whore. I want to see improvement from your walk to your clothing attire to your personal dating life. You must show me you are all in so that I can keep training you and making you a complete sexy vixen sissy slut.

What to do With all my Sissys

Domination Phone SexSlippery and filled with cum was the best way to describe my heavenly cunt when I let my prime big dicked sissy have his way with me earlier today. It was a reward for truly understanding his place, and having a very massive man meat with which I could treat myself. He was the model Sissy, I had to reward him, he called me goddess every time he had to speak up, he waited until I allowed him to talk, he begged me to take his money and didn’t look up from his feet until I let him. Most importantly, he had such a long needy dick hidden behind his bright purple panties! I couldn’t resist, wouldn’t have resisted even if I could, and he never broke character even as he pumped heaving loads of cum right into my greedy slut slit. That I had another less fortunate sissy on hand to eat it all out was just more evidence that it had to happen. I wonder if he’ll call again soon, because I’m really looking forward to another training session, and hopefully the lessons stuck because I’m looking forward to a sloppy wet and sticky reward even more.