Category: Femboy training

Sissy Girl Training with My cheerleader Sissy Fag

sissy girl training Do you know why I enjoy sissy girl training so fucking much!? I get to interact with so many submissive and sissy bois and experience the worship I so deserve! I have a sissy cheer slut! Jeffery is fast becoming one of my favorites. When I answer my phone I hear..

“I am a one pump cum dump little sissy faggot.”

I know it’s my little cheerleader and he needs to tell mistress all about his naughty adventures.
Cheer leader Jeffrey just loves his humiliation at my hands and I enjoy giving it to him. Why, he even has a cheer for me! And you know I am an attention whore so I make him do it all through our sissy phone sex session. I can just see him in his little skirt trying to pick up men as he does his cheer!

My Little sissy faggots cheer!


1, 2, 3, 4 I am a little sissy whore…


5, 6, 7, 8, who likes to masterbate!


Pig tails …. Pom poms and curls,


Watch me make my little cheer skirt twirl…


Yay I am a SISSY!

Don’t you just love a sissy fag who craves dick and name calling? Or maybe your just like my sissy fag Jeffrey? Cock craving, craving abuse little whore… You know the brat of mistress phone sex will take care of you.

Why should I hold your hand?

best sissy trainerWhy should I hold your hand and lead you thru every single little step of sucking a man’s cock sissy? It’s not like this was the first time you ever sucked a dick, I know you have done it a million times. I have seen you do it myself many times so why are you acting like a little shrinking violet now? Do you think it’s cute to act like a little virgin? All it does is annoy the fuck out of me so now I will have to punish you instead. That’s right, bend over you little brat here comes my biggest strap on cock for your little faggot ass. I’m going to fuck that little asshole of yours until it is gaped wide open and you are begging for mercy. And when I am finished I will make sure to have at least a dozen men here for you to suck off whether you want to or not.

Best Sissy Trainer On and Off the Phone

best sissy trainerI enjoy being the best sissy trainer online. My sissy twins will tell you I am the best trainer in the real world too. Most moms would be appalled if they had boys like mine. Even when they were just tots, they were playing in my panty drawer. I knew they were special. They preferred my panties to their superhero underwear. They preferred their sister’s Barbie dolls to their Legos or Matchbox cars. They had crushes on male celebrities. They just never showed any outward masculinity. I started my career as a professional dominatrix. My boys are the reason I became a sissy trainer. I read up on it so I would be able to help them. Parents can harm their offspring if not careful how they handle outside the box interests. They are my boys. Gay or straight. Sissy or masculine, I was going to nurture them. I took them dress shopping. I helped them with their hair and make-up. I taught them how to suck cock and take it up their sissy pussies. They are rocking the sissy look now. They are secure in who they are too. Online sissy training is popular. I get it. You are a closeted sissy with no one to confide in or no one to share your sissy tales with. I helped my two boys become sissy girls so I can help you. Are you ready to come out of the closet yet and embrace your sissy life?

Mistress Phone Sex For Sissy Slaves

Sissy slaves need guidance. The sessions with me as your Mistress phone sex sissy mom are going to be the best way for you to learn your place. You already wear the panties in your relationship and sometimes that isn’t enough. I will love to assist in you dressing for cock. You will come around and understand that your looking pretty and feminine for that big daddy cock is essential. We can get you to that place. I want to train you to be the little cock whore for that BBC that you crave to be. It’s in my very wishes to have you dress and look your sluttiest as you service that cock. You are a slave to big black cock. A simple little pretty slut sissy slave for the much bigger cocks. You are not a man, You are a Sissy Slave.

Mistress Phone Sex

A Halloween Treat

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Oh, my sissy showed up at the door wearing the matching costume I had for him and my husband. They were both Disney Princesses this year. The looked adorable in their little dresses and tiaras. However, I did make one adjustment. I ripped their dresses so they were super short, and I could get a nice view of their pink sissy panties I had picked out for them. Now a touch of lip gloss and we were ready for Halloween. I had already called the anaconda to come see me and the sissies were ready and waiting when he arrived. Always on their knees where they belong. He laughed at their cute dresses as he pulled his cock out and smacked them in the face with it. Then he told them to suck it, like they were bobbing for apples. Once he was hard and wet spots appeared in the princess panties, I had them guide that beast into my wet pretty pussy. Their little hands trembling with excitement as they pushed that beast inside me. Then they watched as he pounded my cunt. Since it was Halloween, he decided they needed a treat. When he was about to cum, he pulled out and graced their little tongues with his warm hot yummy cum. They licked it all up like the cum whores they are. We had much more fun and I will give you all the hot naughty details when we talk. I will be waiting for you.

Kayla’s Big Adventures

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Let me tell you about Kayla. She is new to the game and I can hear the excitement in her voice as I train her. We recently went on a little shopping trip and she picked out all kinds of adorable girly clothing. Some pretty lace panties and sexy dresses. She even got a bright pink butt plug. Then she went home and tried everything on and like a good sissy sent me pictures of her wearing them. The way her man pussy takes that butt plug is amazing. So deep and she was so proud. And the picture of her in black lace panties made her little clitty look adorable. Then we talk and she fucks herself with her dildos. I love listening to her moan as she makes little cummies. The thought of a warm thick big cock in her throat and in her man pussy excites her so much I suspect she is going to be a cum slut and a cock whore. I love when she calls and tells me how she is wearing panties and a bra and her butt plug under her work clothes. It is so hot. I can’t wait to see what we have in store for her next.

Best Sissy Trainer For Covid Fags

These coming months of Winter may be another trying period in the times of a pandemic. The stay home orders are likely to be coming around again. It’s safer to just stay home be comfortable and let yourself be free to express those desires. You can order all the toys and pretty things online and have them shipped discretely to your home. You can call me up and we can have all kinds of fun that doesn’t require crowds. I love the idea of playing dress up and driving somewhere where you can watch people and jerk off in your panties for me. Maybe you can be like one of my pissing princesses and pee your pretty panties and skirts. I love making naughty sissy girls humiliate themselves for me. You can tell me all about the process you have gone through so far in becoming the sissy you are.

Best sissy trainer

Sissy was my little bitch

best sissy trainerSissy was my bitch last night, well honestly she’s a little bitch every day but yesterday in particular I had her working hard. Once of my friends was having trouble with a couple of his employees, they were slacking off and being dicks so he thought he would punish them by making them fuck a little sissy slut. Make it a blow to their egos to have to fuck a lil faggot like that. Well, they were all pissed off about it and even tho sissy was dressed in her best they were calling her all kinds of names and I knew they would be fucking her roughly as punishment. That was perfect for me because this little sissy bitch is a whiner and a complainer so she needed a good rage fuck to make her learn her place. They used her for hours, fucking her lil pussy and her mouth until their boss was finally satisfied that they learned a lesson. My sissy learned one too for sure, I bet she won’t be sitting comfortably for at least a week!

Rub Each Others Clitties For Mistress Violet

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Aww look at you. Thinking you are going to join me in the bath. You know you are not worthy of even being in my bath water dear hubby. How silly of you. However, I do have big plans for you. Well small plans actually but fun for me regardless. Anyways, go pour me a nice glass of wine and put on the surprise I laid out on the bed. There you are standing in the doorway with my glass of wine wearing a slutty maid outfit with pretty silk panties underneath, fishnet hose and pretty black heals. Is that the doorbell? You better go answer it baby. Look at who came to see us. My favorite sissy dressed exactly like you. Now hand me my glass of wine and you two sit side by side. Spread those legs wide and lift up those skirts so I can see those itty-bitty tiny cocks. Oh, how little they are. Now reach your hands and start stroking the others little clitty. Yes, just like that. Keep looking at me though. I love to see your orgasm faces. Now lean over and lick each other clean. You sissies are so entertaining. You won’t believe what I have ready for you to do for me next.

Don’t Be Shy Sissy Boy

sissy phone sex You don’t have to be shy. I’m an expert when it comes to pegging perfect little sissy boy assholes like yours. Do you like my strap-on? It’s hard, black, and 12 inches for you. Aren’t you excited that I’m going to stretch out your little ass hole baby? Why don’t you start by worshiping it first. You had better get it nice and wet with that hot hungry mouth of yours, because the only lube that I’m going to use is whatever slobber comes from your fucking throat. Oh yes baby, choke on my fucking dildo. Show me how much you want me to fuck you in that little ass. I know you bitches love it when I peg you, so make sure it’s just wet enough so that I can slide all 12 in into your asshole. Oh you’re perfect, now bend over and spread those cheeks. Look at you! You’ve never even had anything in your ass have you? This is going to be a lot more than just the pinky sweetie. This is going to be 12 inches of hard black cock pounding away at your prostate. Are you ready to get pegged? Good. Let me line up with your little shit hole right here, and boom! I’ve shoved all 12 fucking inches right into you. Just give it a minute to stretch, but I’m not going to slow down. I’m going to fuck you at supersonic speed and show you exactly what a fucking little slut you are for me.