Category: Best sissy trainer

Sissy phone sex with Miss Remi

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Sissy phone sex Mistress Remi is going shopping today! I’m going to get lots of pretty panties, bras and other sexy lingerie for my little bitches to wear tonight. Call and tell me your sizes so I can grab something for your slutty ass to wear too. We’ll have a girl’s night and get all dressed up in cute outfits. I’ll do our hair and makeup and then call some guys over. I know a few sexy bbc studs that are aching to destroy a tight, virgin boy pussy! When I have a room full of the prettiest and most well trained girly sluts, I’m going to bring in my team of bull-studs and let them go crazy on those sissy bitch, whores. I’ll let them rip the panties and stockings off of those faggy hoes like they’re opening Christmas presents! I expect my sissy bitch girls to take those giant cocks just like we practiced when I was fucking their mouths and he-pussies with my strap-on. Remember your training and do what Miss Remi taught you. Relax your jaw and take that huge cum cannon down your throat inch by inch until you feel those big, cum filled balls slapping up against your chin. I know you’ll be gagging and choking but you better not stop throating and gagging on that big dick until you feel it throbbing and you can taste his cum! I need you to suck the first load out so that he’ll last a long time when I bend you over, hold your cheeks open and offer him your sweet, boy pussy. I’m just about ready to leave for the mall so you better hurry up and call me so we can talk about what kind of panties and bra you want me to dress you in!  

Depraved Domination: A Sissy’s Descent into Humiliation

 

David, my pathetic little sissy, needed a strong hand to keep him in check. His weak demeanor and submissive nature were an itch I had to scratch. Bound and gaged, he was mine to dominate as I pleased, and oh, did I please myself!

I started with some light torture, ensuring his compliance. A little pain never hurt anyone, and the way David whimpered only egged me on. I ran my fingers along his body, savoring the shivers that rack his frame. He was mine to control, and the power was an aphrodisiac like no other.

I made him beg for my touch, pleading for release. But David wouldn’t find any until I was good and ready. The humiliation etched across his face only deepened my desire. I owned him, body and soul, and the thought of it made me drip with anticipation.

My fingers explored his sensitive spots, and his helpless moans encouraged my every filthy desire. I’d make him suck my fingers clean, like a good little sissy. The sight of him on his knees, eyes downcast, was a sight to behold.

I mounted his useless frame and rode him rough, making sure to remind him of his place. And the whole time, David took it—the submissive little worm!

This is our little secret. David’s too scared to ever admit what a filthy, submissive sissy he is, and I intend to keep it that way…

Mistress has spoken!

Sissy humiliation training with my favorite gonner fag!

Sissy humiliation trainingMy anonymous little sissy fag loves our Sissy humiliation training sessions whenever he is free to chat and get nasty. It has been a while since we talked so tonight was such a fucking ride. My little faggy boy went shopping and bought the sluttiest outfits to show off for me. We obsessed and gooned over the biggest black cocks we could find while he showed off his amazing cock sucking skills. During our time together he showed me his lovely BBC toy which shot out massive loads of thick and creamy cum. His handsome faggot face looked lovely covered in that hot messy seed!

Over the past few months I have been helping him become the best sissy version of himself. I am so proud of the progress he has made during his Femboy training time. My sweet little cucky boy has shown an ample amount of new fantasies that he has been obsessing over for quite some time. I watched him lay back in his chair while he stroked that hard little dick of his; my pussy was drooling with anticipation. He started detailing some personal information about his girlfriend being obsessed over her EX’s huge cock. My little fag boy was gooning so hard as he told me how much he loved thinking about his girl being dicked down by a big dick. It turned him on even more because it was her EX whom she has already fucked many times before him!

Your Phone dominatrix has a sissy hole you need to suck

Sasha your Phone dominatrix is waiting for you.You need some  tough love baby. I know your hole is hungry for BBC. Go ahead, do a bump and let out your sissy. Who cares if your girlfriends out? I don’t.Phone dominatrix

I want you to show me  just how dedicated you are to your new life as my sissy whore. And what better way to prove your devotion than by tasting the sweet nectar from another one of my sissy sluts?

I think you aren’t ready yet for fat black cock, you crave it, think about it all the time to humiliate you but you gotta show me. I have another Sissy whore that also wants her life ruined. I would turn me on so much if you cleaned out her hole for me.

Don’t be shy, she’s a little sissy whore just like you, and I’m sure she’ll love every second of it. I need more of you whores under my control so I can go on a nice vacation. I will be sure to run your account dry but at least your clitty will be nice and sticky.

Believe me, you need a lot of Forced sissy training, which means you do anything I say. Show me how obedient and thirsty for sissy humiliation you really are. And trust me, if you impress me, I might just consider letting you service some of the best black cocks.

You see, Sasha, sissification isn’t just about dressing up in pretty clothes and prancing around like a princess. No, no, my dear, it’s about embracing your true nature as a submissive sissy slut who loves to serve and pleasure cock. 

 

Best sissy trainer for the summer 2024 Dildo Olympics!

Best sissy trainerBest sissy trainer for the summer 2024 Dildo Olympics! Paris, the city of love and sensual domination, is hosting this year’s Summer Olympics. My mind has been on a few of my favorite American sissies who need some training to bring home the gold in Dildo bouncing. I have the perfect ruffle Olympics themed sissy dresses with all the bells and whistles for you to put on a good show at the games. And the dildos we will be training you on run from six inches to over a foot long. The Winner of the medal is the sissy whore who can bounce the deepest and longest.

Of course there are other categories you will be judged on as well! I wouldn’t be the best sissy trainer if I didn’t have many rules for our American sissy athletes!  So, if you want to win, you better train hard and obey the rules. And don’t forget your sunscreen! 

Category and judging shall be held by me and a team of my favorite mistresses to see who can handle the long bounce. That’s the longest and deepest ass pussy drilling on several different kinds of Phallus of the judges choosing. 

The next event is the Best of show. We all want to see the best American Olympics summer outfits a sissy whore can wear. The Best sissy trainer with the sissy boi who performs the best will win the cash and the gold medal for her mistresses at the end of our games! Our sissies will compete and be judged on feminine appearance, grace and overall sluttiness and willingness to perform for her mistress!

Best sissy trainer for the summer 2024 Dildo Olympics!

The long jump will be in full sissy gear and six inch stilettos over a Pool of cum. The volunteers have all had our teammate sissy bitches drain cocks into a small pool. If I had enough time it would be Olympic sized, but a small plastic pool still holds 100’s of cumloads! 

Another event will be cocksucking. Every mistress will chose the biggest and thickest cocks for each mistress to have her sissy suck off using a stopwatch. This summer, games are going to be lit. Let’s start with our sissy slaves running that torch of faggot love across the country! Who will win the Gold!

Best sissy trainer

Phone Dominatrix Meadow Milks Your Girlcock with Fleshlight

Fleshlight Fun with Phone Dominatrix Meadow

A real phone dominatrix knows that domination isn’t just about rough pegging and humiliation. Some of my sissy boys like losing all control to their mistress. And that’s when I use a little fleshlight fun. I take a pretty piece of lace and wrap it around your wrists. Even when you feel like you can’t keep going, you won’t be able to stop me. I grab one of my vibrators and place it against your clit.

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Your clitty is throbbing for me immediately. My heavy tits are in your face and the vibration on your sissy cock is making it so sensitive. I remind you that you aren’t allowed to cum until I allow you to. When I see that precum soaking those panties I pull it away. I pull those panties down and lean down to lick the tip of your girlcock. A reward from your phone dominatrix for being such a good girl. And to make sure you’re as sensitive as I need you.

Beg Your Mistress to Cum

You watch while I grab a fleshlight and start squirting lube inside of it. I bring that silicone cunt up to your pretty clitty. I ask you if you want to fuck this pussy for me. You start begging for it like a good little slut. I get behind you so you can feel my tits on your back. Then I slide that fleshlight down on your sissy cock. You moan so loud for me. I love when you whimper like a little slut for me.

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I tease your girlcock with the slowest pumps. Each stroke sinking as deep as you can get inside of it. But when I feel like you’re too relaxed I pump your girl cock faster. I slide the fleshlight up until it’s just touching the tip of your sissy cock. I focus it on that sensitive tip and grip your cock with my hands. Your phone dominatrix knows when you’re close to cumming. Every throb and pulse of your girlcock warns me that you’re about to squirt. I whisper in your ear that I won’t let you cum until you’re panting like my pretty little pet.

Sissy panties need to be ripped off that sissy ass

As a mistress sometimes you get in the mood to just rip some Sissy panties off and ram your strap toy in. I give you lots of training and always use my favorite bbc to break you in. Therefore, I grab my biggest strap. “Get on your knees,” I instruct you to do. After I lube my toy up, I rip your panties off. Right away your clitty twitches. “You are such a pathetic little slut” I grunt as I push deep in your sissy cunt. I start humping away at you and I could feel my start rubbing on my clit.

Sissy panties

The harder I fuck you the better it feels rubbing on your mistress clitty. “Fuck back at me like I trained you to do with big black cock” I demand of you. Since I have trained you well, you fuck back my cock strap hard. “Your sissy ass was made to be used by anything, look how well every inch of my strapcock disappears inside you. As my clitty gets rubbed by my toy, yours leak from the abuse your mistress is giving your manhunt. “Mistress can I please cum” you beg as I fuck you. I love seeing you squirm. Stopping you from cumming is one of my favorite tortures.

So, I just keep pounding you harder. The best way is to put my foot on your back and just ram you like I have had many bbc bulls do to you. “Mistress please let me orgasm” you beg squealing like a fuckpig. As I laugh, I tell you how pathetic you are and how fun it is to have you flopping underneath me. “Let your pathetic clitty make a big mess for you to clean up” I instruct. I watch as you limp up and explode all over the floor. “Now clean up the mess you have made, mistress needs your mouth” I say as I lay back and expose my wet cunty.

Panty-Balled Princess: A Sissy’s lesson

 Sissy training

You’re a lucky, lucky bastard, about to embark on a journey of pure, unadulterated degeneracy. And trust me, it’s gonna make you cream your pants.

Imagine a delicate little thing, a sissy slut dressed in pretty pink panties, soft as a newborn’s butt. This sissy’s got a cute, round ass that’s just begging to be spanked, and a panty-clad crotch that’s dripping with need. Sound delicious?

This mistress has been put on this earth for one reason only: to make you her own personal plaything. And boy, do I love it. My good sissy girls, ready to serve, with a little twerking ass that’s a joy to behold.

I’m talking ass cheeks that spill out of those panties, just begging to be pulled apart and dominated. Go on, imagine yourself as my Slave,  My friends with massive black cocks taking you from behind and preparing to turn your sissy ass into his personal cumdumpster.

Oh, he’s a desperate one, facing you now with a faint glaze of pre-cum marking the outline of his cock. Yeah, he’s ready—ready to be humiliated, used, and abused. That’s the way he likes it.

But will this sissy get the attention he craves? Only after he’s earned it. So bend him over, smack that ass, and prepare for a twisted journey of sissy domination.

Enjoy the ride, you nasty pervert, as this Mistress is about to show you the time of your life. And remember, she’s always ready for another round—with a true cumslut, just how I like ’em.

Sissy Slave Training Can Make You More Feminine

So many guys call me and ask how they can become more girly. First off with some Sissy slave training that girly side of you will begin to emerge. Like a Butterfly out of its chrysalis emerging for the first time into it’s full glory.

Likewise speaking of glory, a glory hole is one great way for that training sissy to get a feel for sucking some real cocks. However that usually tends to come later. One step is to start wearing those pretty panties. And start to remove the hair from your body.

Once we get you comfortable and feeling feminine we can incorporate some toys. Sometimes the toys come into play before the feminism. All of my sissy faggots have their own style and speed and direction of how we start. It’s all in what is comfortable with you and where you wish to begin.

Finally, we should always have a session of getting to know each other to start. Nothing better than you telling me about who you are and how and when these sissy desires started. This is my invitation for you.

Sissy slave training

Sissy Training Lets Us Explore Who You Really Are

sissy trainingI bet you need sissy training. Many men do. And I do not believe there should be any shame in that either. Recently, I took on a new real-time client, which I rarely do anymore. Sometimes between motherhood, my sissy line and a personal life, I struggle with balance. Something had to give so I could be better at work and better for my offspring. So, I limited the number of sissies I see in my home.

But I made an exception for Lilly. Sissy Lilly goes to school with my sons. However, her mother fails to be as cool as me. I let my sons be who they want to be. And they have time to figure it all out because they have a mother who supports them. Right now, we know they are femboys who love girly clothes and cock. I let them wear dresses and pretty clothes to school. Having the best sissy trainer around as their mother they view as a plus.

Let Me Help You Become the Best Sissy Ever

So, if Sissy Lilly cannot be who she wants at school and home, she can be who she wants at my place. No reason for her mother to get suspicious either. My sons and Lilly are great friends. So, when Lilly visited my boys for the holiday weekend, we played dress up. I let her pick out what ever she wanted to wear from my sissy closet. My closest proves to be a magical place for sissies. That’s because I keep my closet full of pretty and frilly things. Very girlie clothes for sissies.

Lilly picked a purple bra and panty set from my vintage Madienform collections. She possesses great taste. And she picked out a purple frilly dress. She picked out a different colorful outfit every day she stayed here. I will be Lily’s safe space for exploration. She can be Chad when at home, and Lilly with me. Just like you can be your authentic self when you call my sissy phone line. Whether you want to be a pretty sissy or a cock sucking sissy, I do not care. I am here to help you be the best sissy you can be.