Category: Taboo phone chat

Stepbrother Forced Sissy Training

I walked in on my stepbrother after he hopped out the shower and I saw how little his white dick was. I started laughing at him pointing at his big clit. I walked up to him, pulled my panties from the hamper, telling him he will dress as a bitch because that is what he is. Being a girl is fun i told him you get fucked and filled up. I stroked his little dick trying to get pre-cum out and when he started leaking, I wiped some with my fingers into his mouth making him lick my fingers clean. “Oh yes a good sissy bitch knows how to clean a cummy mess”. I knew my boyfriend and his big black cock were coming over so i made it clear to my sissy white stepbrother that he is my bitch toy to us as i want and to not say a word. I blind folded my boyfriend and walked him into my room.

Forced sissy training

There I pulled his big black cock and grabbed my stepbrother’s head and pushed it down, making him suck his BBC. My boyfriend called him a good cock sucker and slut. Then i bent him over and told my boyfriend to fuck me. I guided his cock into my stepbrother’s asshole. I played with my cunt as my forced stepbrother was getting fucked and filled up by my BBC boyfriend and it made me so very horny.

Sissy Phone Sex

sissy phone sexI told my little slut to come here and suck this big black cock the way I trained her to. She put her big dick sucking lips to work right away like a good little femboy. I got her all dressed up in pink panties and bright red lipstick for tonight’s occasion. She was going to make me a shit ton of money with her tight ass body whether she wanted to or not. I yanked her up by her fucking hair and told her to be a good little sissy and lay on the bed. She started stroking her small cock so of course I punished the bitch. I went over and slapped the bitch in her face and pulled her legs open revealing that tight dirty asshole he wants. I told him to shove it in her as hard as he fucking could and then maybe she’ll learn her fucking lesson. He shoved his dick in so fucking hard she screamed so I had to sit on her face to shut her the fuck up. He fucked her so hard and fast that he came inside her tight dirty asshole and of course she thanked him for it after like a good little bitch would.

How Will You Serve Mistress Raine?

Mistress Phone Sex

My sissies love making their Mistress Raine cum hard hearing about all the cocks they have taken! It’s no secret that my sissies are the best cum sluts out there, they fuck with the intention of telling me all about it. They love hearing the happiness in my voice when I tell them they drained those balls exactly as I would have. My sissies are completely devoted to being obscene cum dumpsters on a mission to take as many cocks as they can before their holes are all fucked out. My sissies love sending me pictures and even videos of them sucking a taking cock in their tight little boy pussies. If you think you have what it takes to serve me and be one of my very fuckable sissy sluts, Call me!

Femboy Trainer Jackie

femboy training

If you’re in dire need of femboy training, then I am just the Mistress for you. I love nothing more than helping boys just like you transform into the most gorgeous femboy slut you’ve ever seen in your life. Sure, you can be a sissy and just kind of do it haphazardly, but that’s not what you really want, is it? You want to be the very best version of yourself and if you stick with me, that’s exactly what you’ll be. Everyone will be in awe of your beauty and transformation, and that’s when you’re going to start getting cock.

So, until your training to be a femboy is complete, you don’t need to worry about dick. You will get it in due time, but that time is not right now. We’ll be talking about how to turn you into the prettiest sissy in your town. Hair appointments, waxing appointments (this one is super important), manicures and pedicures, lingerie, and shoe shopping – all of that and then some is in your future. Are you ready to be fully feminized by a woman who knows exactly what she’s doing? Then book a session now for your Cinderella moment!

Sissy Panties Full of Cummies!

Sissy Panties

Your sissy panties are going to be soaked when I’m done with you! You are such a good sissy that Mistress is going to let you feel her superior pussy pressed up against your clitty! Only though the panties though as I don’t want you to get too spoiled. Giggles. As I grind back and forth making your itty bitty dickie will feel wet and sticky from my cunt juice you need to be worshiping me as the Goddess I am. I’ll even let you suck my toes while we scissor. pretty little slit so wet and sexy but no more for you! Get down and assume the position so I can spank your tush! The only sound I want to hear is the sound of you moaning and begging for BBC while I smack your rump! Right when When I think your man purse is ready for me to drop change in it, I’m going to go balls deep in you! Mistress is going to milk that prostate until your man pussy squirts! 

Breaking In New Pretty Little Sissy Bitch

I have a new pretty little sissy bitch since my perfect sissy has strayed and I wanted to show my new one how to be.

Sissy slave training

I bought the biggest two-sided dildo I could find. I bought some new sissy panties and bralette set with matching stockings. When my sissy walked in, she got naked right away I love watching her little clitty in between her legs excited to see me. I turned her around and spanked her ass and made her tell me who she belongs to. She got dressed in 6-inch heels and crawled to me. I spread my legs so my sissy slut could lick my cunt and get it wet for the strap on dildo I had for us. She did as she was asked and when I put it on, she was bent over spread open showing me that man pussy. As I pushed my strap-on deep in my new pretty little sissy the other side went deeper in my cunt. I started fucking her hard and deep making sure I used her so I can cum hard. I didn’t stop until I felt my body tense up, I started cumming hard. I pulled out of her now gappy man pussy and told her to stay that way until I was ready for more.  

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.

dick breath

 

Are you craving chocolate honey, aren’t you? Something big and juicy won’t fit, but you will beg to make it work, huh? Don’t lie. You know you want the mark to fuck your ass pussy. Don’t get your panties all wet, and you sissy cum fuck. There are some rules to fluffing because that’s what you will be ultimate. Mark wants no part of your sissy cock. Instead, he wants you to prep him up by sucking his cock and being the vacuum.

What do you think a vacuum is…. I’ll wait. Hmmm, still doesn’t come to your sissy mind? Maybe it’s cause you keep staring at Mark’s big cock! Now you stop it right now. You better listen to me give you some humiliation phone sex to pass the test. A fluffer is a pregame and endgame. You should be happy you start something and clean it up like a vacuum. Enjoy your dick breath bitch!

Humiliation phone sex

Taboo Sissy Phone Chat

taboo phone chat

I just had the most taboo phone chat with one of you little dick sissies. This slut spent 45 minutes begging mistress to fuck him in the ass with the biggest strap-on that I own. I asked if she was sure because the biggest Mistress Heaven owns is 16 inches long and thick as fuck. This BBC will stretch your shit hole open so wide that your ass will be gaping hole for at least a week! I thought that would scare her but she reached in her bag and pulled out an adult diaper. This sissy wanted mistress to make her into an adult baby! This was some uncategorized shit but I still did it! I love fucking a tight hole until its loose. I must admit, I loved having a little sissy baby! I dressed her up in cute little dresses and nursed her while I rubbed my clit. Her mouth around my tits made my pussy tingle! After I gave that sissy some grade A cock I put her diaper on and carried her around like a little baby until she fell asleep in my arms. So cute! 

Sissy Slut Earned His Punishment

Nothing better than a mistress that knows how to punish you in the best way you love. I know how to put you in your place. My sissy maid hoe that is all you are. If you forget to clean something right or you don’t milk my BBC bull friends right, I will bend you over my knees and give you a sissy slut spanking. I won’t stop until your ass is red and swollen.

Mistress phone sex

That is when I will put my big strap-on on and fuck you hard, showing you who you serve and who you belong to. You little clitty leaks all over my hand when I touch your chastity belt. I don’t stop until I make you scream who you belong to. Hearing you say you belong to me and having the end of the strap rubbing on my clit as I fuck you, I don’t wait, and I pull out and spray you all over with my cunt juices. When I am done you right away get to cleaning my mess with your mouth like I like, and I know my punishment worked.