Category: Best sissy trainer

Unmerry Sissy Mistress Phone Sex

Mistress phone sex

Christmas time mistress phone sex is a bittersweet creamy treat for all of you pathetic losers who don’t have anyone who wants to hang out with you for the holidays except for my sissy sluts.  Sure, nobody in your personal life likes you enough to invite you over for some holiday fun, I get it.  You don’t have to explain to me what it is that makes you a simpering idiot in life, I really don’t care.  You’re here calling me for a hardcore ass fucking from one of my biggest dicked femboys on Christmas day.  You’re a miserable man for one reason or another.  That’s all I need to know.

Where’s your family?  I know you don’t have a girlfriend or anything like that, but where are your parents or grandparents or whatever?  Don’t you have anyone who gives a damn about you who might want to see you today?  Not a dinner with a co-worker’s family or anything?  It’s so sad that your only hope for holiday happiness is one of my beautiful lady’s long, hard penises.  Don’t get me wrong, I don’t mind and she won’t either.  I know I have at least one or two big wanged women who would be happy to gape out your ass gash, that’s what they’re for.  I’m just saying, pretty sad, Bro.

Are you going to cry throughout the entire sphincter stretching session?  I know it doesn’t hurt that much, does the hardcore pounding from a gorgeous he-bitch just help you to release all of the pain you feel inside, or something?  What’s that?  No, it just plain ol’ hurts because that whores cock is the biggest hunk of she ham you’ve ever had lodged up your hairy asshole.  Yeah, that tracks.  Whatever it is, cry it out here, Guy.  This is a safe space for all of your Christmas time woes and your unmerry tears.  Just grit your teeth and take it if she starts giving you too much, you’ll thank her for it. 

 

Sissy Training: Choosing the best heels.

Sissy Training

I just love when my pretty little sissy sluts take a whole new step in their sissy training journey! Allowing me to set up extra special tasks for them, like picking out new heels or pretty skirts! Being a girl, the most important part about feeling totally fabulous is almost definitely how you dress and accessorize yourself. Sometimes it’s hard to find your perfect style or things that would look the best on you. That’s what I’m here for! To help you love your best sissy life being the best little cock sucking whore around. But, being dressed to the nines while doing it!
just the other night I sent my super special sissy on a shopping trip to pick out the absolute best things, making her send me pictures and allowing me to choose exactly what she was purchasing. That’s the beauty of having an online phone mistress. I’m here to help you every step of the way!

Sissy humiliation training

BBC sissy trainerHahaha, Sissalina has the tiniest peenie.. I would call it a clit but after comparing that microscopic little organism to a woman’s clit.. I think we can settle with calling it a nub! I made her tug her maggot in front of me and Marissa while we giggled about how pathetic she was.. That little piggy seemed to be lost.. Watching her tug until she was ready to explode then forcing her to stop and stunting her little orgasm was the funniest thing to watch!

Little cocks like hers do not deserve to squirt haha.. That’s what big black bull cocks are for! If she’s on her best behavior maybe I’ll let her watch that chocolate cock cum deep inside of me.. Then give her the honors of giving me a nice cum clean up. Given that the only thing she is good for is making me laugh.. I felt it would be so selfish not to bring Marissa in on the fun!

Using her as the main serving of entertainment was perfect.. We made her strip down completely naked and humiliated her the entire night… haha, we had her pathetic little dick at our disposal. She was super shy to share her shrimp dick pics with me so I made a pinky promise while having my fingers crossed.. No duh, Loser! Now, everyone on the slut hut will know of your terribly tiny winky…

Reading all of your messages of you begging and pleading with me not to share, made me want to share them even more. If your pathetic peen is good for anything, that’s making me laugh! Now let’s get that maggot in a nice pink bow.. If we are going to be playing dress up, there’s no better way than to glamorize that weenie while we laugh. Loserrrr! Don’t get your Sissy panties in a bunch LOL

Sissy phone sex

Humiliation phone sex with the Best sissy trainer!

mistress phone sex for the holidays

mistress phone sex

If you want mistress phone sex, you will be shelling out to me more than you know. I’m a mistress that enjoys a sissy spoiling her rotten. As I make you my little sissy bitch you make me happy by fulfilling every single wish I have and more. When in doubt, shell out. My motto is simple and if you want to be the best sissy for me, you will do all I ask without hesitation. Show me you’ll do anything to keep a smile on my face and prove that you will make your way by making me your mistress who fucks you over and shows you how to be an infinite cock sucking sissy bitch.

Jingle balls all the way; make sure you stay and play.

Gift Yourself The Best Sissy Trainer!

Best Sissy Trainer

My sweet sissy baby doll, I’m so proud of you for making it through the year and now it’s time to spend a little on yourself for some holiday cheer! I’m ready and waiting to train you in all my slutty mistress ways; you’ll learn how to suck thick hard cock, get fucked and dress like the bimbo that you have been dying to let out. Once I show you how to shop till you drop and make that face look glamorous, you’ll be the hottest slut to get fucked. I’ll make sure you are the prettiest princess at the Christmas ball and by the stroke of midnight you’ll be filled with to the brim with cum! There won’t be a single pair of balls that hasn’t been drained by my sweet sissy slut once you’ve treated yourself to a quality training session with me!

Sweet Sissy Boy

Best Sissy Trainer

This best sissy trainer has some big plans for you! I love tying you up like the little piggy that you are! I have you dressed in your slutty and sexy clothes baby! You have your ass hole stretched out with a dildo. I have a few big black nigger cocks ready for you to be played with. I have you on your hands and knees ready to take them in your tight fucking shit hole. I let them come in and on gets on his knees and tells you to open your whore mouth. You do as he says, and he uses that fucking throat to thrust his hips into to! Don’t worry baby there’s plenty more to come!

Sissy Panties For Santa Claus

Even Jolly Ole Saint Nick has his secrets and kinks and wears Sissy panties. We all know that Santa Claus is completely fictional and is all about a good time. So my local Mall Santa is really completely naughty in his love of a good time. I paid Santa a Visit and sat on his lap. And I whispered in Santa’s ear that I know what he has on under that red suit of his. With this little tease I made Santa turn red.

You see I caught a Glimpse of Santa getting into his Jolly red suit. I saw that Santa was sporting an extra sexy white lacey panties. When I sat on Santa’s lap to let him know what I knew, there was more to it still. I may have been dressed as Santa’s helper as I do for charity every year. In the back dressing room I caught a glimpse of Santa and his panties. But that wasn’t all Santa was also wearing pantyhose. 

I whispered that I knew my big man Santa Claus was really a little crossdressing sissy and if he didn’t come to me for proper training I would out Santa and make all the Elves pump in his bottom. The thing is, the Elves all had big black cocks. So training is underway on the Day after Christmas so Santa can be the best BBC cock sucker there is in his pretty lingerie playing the role of a Ho ho Hoe.

Sissy Panties

I needed to remind my sissy about all her Sissy maid training she needs

I needed to show my old sissy bitch who was in charge she had not come over for a while and she was overdue for some Sissy maid training. As soon as she came in, I got her on her knees. My shoes all needed cleaning and I wanted her to use her tongue. She did so good and cleaned every pair, she just needed to clean the ones on my feet. When she opened her mouth, I shoved my heel down her throat making her choke like a sissy bitch does on a dick. I told my sissy bitch to suck it like she was trying to get a nut out and that is what she did to my heels. When they were clean, I bent my sissy over my knee and gave her some hard spankings with my paddle. She thanked me and begged me for more. I liked hearing her beg it told me she knew what she was missing. I stood up and told her to bend over as I was putting my biggest strap-on on. i knew my sissy could hear what i was doing and I saw her clitty twitch in her panties. I moved her Sissy panties to the side and rammed my cock deep in my sissy bitch’s pussy. I fucked her hard and raw making sure I was going to leave this sissy slut sore. When I was done, I saw all the gooey mess on the ground from my sissy enjoying the pounding I gave her. I made sure the cum mess from her sissy clit was cleaned up before I sent her home.

sissy maid training

Sissy Phone Sex with Big Black Cocks

sissy phone sexLooking for sissy phone sex? I love all my sissies on and off the phone. For my real-time sissies, I decided to throw a special holiday party. It was a themed party. It was all about celebrating the Black New World Order. I have a lot of BBC sissies. Most men come to me for their sissy needs because they know I will train them with big black cocks. Many white men understand they are inferior to black men. At my little Christmas soiree, I had my BBC faggots in red and white Mrs. Claus outfits complete with white stockings and red bows on their little jingle balls. I had 8 BBC sissies, plus my two sissy sons. They like big black cocks too. They are not exclusively bbc sissy boys, like many of my full-grown sissies. But they appreciate how big, powerful and beautiful those big black cocks are. Since I am a BBC sissy trainer, I made sure only the best black bulls in my pen where there for my sissies.

It became a feeding frenzy when big black cocks came out of pants wearing a red mansleeve with mistletoe hanging off the balls. My little white sissy sluts begged for those big black cocks. There was a black cock for every sissy, but I fed them more than once. It is the holiday season after all. When a black cock would cum in one of my sissy’s holes, then he would move on to the next sissy. One of the reasons that black cock is superior to white cock is how much it can cum. One big black cock can cum more than a dozen white cocks combined. Facts. So, every sissy got at least 10 loads of holiday cheer from the best cocks in town. They also got fucked in their back door sissy holes too. The holiday cheer will be oozing out of their sissy holes for days. I thought it was a great party. This phone dominatrix always throws a killer party for her BBC sissy faggots. Maybe you can attend the next one?

Femboy training: Do you wanna be a good little slut for me too?

Femboy training

One of my favorite things about femboy training is when my sweet little sissy Becca blows me up for attention just dying to talk to me knowing that I’m super busy! It’s the best feeling ever to be worshiped by such an obedient cock sucking slut. I really really enjoy when boundaries get tested and limits get pushed. The size of the dildos disappearing deep inside her sweet sissy pussy getting bigger and bigger. 

Just imagine being ordered to put a wig, fishnets, skirt, panties, and lipstick on before we get to get down and dirty with some play time! There’s nothing better than a dirty little slut doing what they are told and making me so happy! Completing all of the tasks I’ve assigned is just the best little slut ever! 

Come be my dirty little whore too, let me show you just how much fun we can have together!