1,510 results for sissy training

Christmas git of big black cock for my favorite sissy

I gave a Christmas gift of a big black cock to one of my favorite sissy sluts. He obeys so when and he will always clean up any mess I have. He never lets me down when it comes to his Sissy maid training. Even when I show him, he needs improvement he will take every spank with pride and begs for more while thanking me. I called over my favorite bull with a big 10 Inc monster black cock that I can’t even wrap my fingers around it. After some time, he arrived. I had my sissy bitch greet him with his ass in the air on all fours like a dog bitch. It is what I like, and my sissy slut knows it. I pulled my bull friend’s heavy flaccid cock out and laid it on my sissy whore’s face. Like a dog bitch she sniffed it and tried to lick it with her sissy tongue. I could tell she was being so teased that her little dicky was leaking through her sissy panties. I looked at her and told her to not let me down. That is when she opened her mouth and went to town sucking on that big fat dick until my sissy bitch got a mouth full of semen. I know my sissy enjoyed his gift.

Sissy maid training

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!

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

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!

Sissy Slut Maids Don’t Just Clean

Sissy maid training

One of the biggest benefits of my super slutty sissy maid training is that my apartment is always spotless!  I have so many femboy maids under my thumb that I never have to worry about dusty shelves or cobwebs in the corners and having an unpleased, dry pussy while my housework gets done is a thing of the past.  All of the household chores that I don’t want to do, which is all of them, get delegated down to my caged dick queenies and if they want me to allow their little clitties to cream, they know exactly what they need to do.  Satisfy Mistress K in every way.

I don’t just want a man maid that just dusts the room in a sexy maid outfit, any guy can dress up and do that.  My sissy slut maids need to jam a feather duster up their asses and clear off all the dust with their buttholes.  Same goes for sweeping and mopping or anything with a handle remotely cock shaped, really.  The vacuum too, it’ll even vibrate on their prostates and milk out some cum as they’re cleaning the carpets.  I love the sight of a woman wannabe with a Kirby handle jammed deep up her craphole, the faces they make are priceless!

Clean my commode and you better stick that brush up your butt and swirl your ass around to do it.  Wash my dishes and find the fattest pot handle to push as far into your tight little pooper as possible.  See what I mean?  If you just clean my stuff, you’re only a crossdressing man wearing a maid’s uniform helping me out, a little. Use everything you get your hands on to ram into your rectum and stretch out that ass pussy of yours, then you’re on your way to being a real sissy slut maid.  You’ll know if I like the job you’re doing by how much I let you touch my cunt.  If I’m happy with your work then you’ll have my permission to bring me to orgasm, just remember to clean all the pussy juice off of me when I’m finished.

 

Secret Sissy Survives My Cock

Sissy Girl Training

 

I met this man who was a secret sissy and invited him over to my place. I figured it out when I caught him staring at my computer that had sissy porn in it. When I pretended to leave the room, I observed him watching sissy porn. I burst into my room, acting shocked that he was watching porn in my room. I told him that I would not expose his porn preferences to the world if he were a good sissy slut for me. My landlord wanted to convict me for unpaid rent, so I told him that he would have to learn to take his big cock down his throat. When the secret sissy told me he had not ever sucked a big cock, I was surprised but prepared. I got out an 8-inch strap-on and told him to suck it. He sucked it obediently. After a couple of minutes, I grabbed the back of his head and rammed his cock down his throat. He gagged and struggled a bit, but he took it like a good cock slut. With a few more of these sessions, he will be ready for the real thing. 

Femboy Training with Heaven

Femboy Training

I hope you’re ready to begin your femboy training because this is it! You have one more hour left of freedom before you’re locked in chastity on my command so you’d better do all you can to put that worthless dick of yours to use now because it’s your last chance. As a courtesy, I’ll allow you to stare at my perfect black tits and ass while you stroke away; I’ll even do you the honor of watching me get fucked by a big black cock…soon enough I’ll train you to fuck a cock halfway as good as I do (although you’ll never be as good as me). You’d better not make a mess on my floor when you cum, either, and if you do, you’re going to lick it up, just like you’re going to lick the cum and juices off my sheets after I finish fucking; this is me slowing acclimatizing you to the cum whore I’m going to make you within the next 30 days. You’re going to be eating and drinking so much cum, it’s going to be all that you crave. Here; I’ve picked out some pink sissy panties and a beautiful bra for you to wear. Enjoy!

Sissy Phone Sex Update: Becca Takes A Huge Dildo!

Sissy Phone Sex

The sweet whimpers during sissy phone sex, of my sweet little slut shoving the massive dildo deep inside of him. Drive me insanely crazy. It spikes something inside of me that just makes me want to grab a bigger one and thrust it deep into that pathetic aching sissy hole. My sweet little sissy Becca and I just started a Sissy/Mistress journey together. That I can’t wait to continue, the homewrecking and forced training that is coming will be stories to blow your mind!

So Friday, before I went out for the night with my friends, I had Sissy Becca go to the porn store and pick up a few items for our playtime. She grabbed a dildo *the one pictured* and some fishnet stockings. Trying not to fall victim to my amazing voice and witty mind, she sat in her car until I finally told her she needed to come home or I was going to post her face to this story instead of just her bum. You see, I absolutely adore sissy blackmail.

There’s something about a little slut whimpering and obeying because they are scared of what’s about to happen, that just makes my teen Domme pussy drip!

Best Sissy Trainer Helps You Be the Best Beta Boy You Can Be

best sissy trainerThe best sissy trainer is what you need. Maybe I can be a little gift to yourself? I love sissy boys. I like all sorts of submissive men. Sissies, cuckolds, cock sucking faggots, adult babies and maids. I have a few of each in my sissy posse. Alex has been seeing me for about a year now. I was his Christmas present to himself last year. He said he just wanted a few sessions, but our explorations prompted him to keep coming back. He came to me confused. He knew he was not a normal alpha male. He knew he had a small cock and was unable to please his wife. He sometimes gets off wearing women’s panties. He fantasizes about sucking cock. He just did not know where he fell in the spectrum of submissive men. Many submissive men overlap their niches. I have lots of sissy boys who come to me for sissy training, but they quickly find out they are more than just sissies. They are often cucks and cock sucking faggots too. Alex is primarily a cuckold we discovered. He likes to wear panties and suck cock, however, he does not want to suck cock if his wife is not present. He likes to service men for her. A lot of sissies just love cock. They want to be a beta bitch to an alpha male with a huge cock. Not Alex. He just wants to suck cock to please his wife. He wants to do the labor so she can enjoy the action. He is a submissive male, but not a 100% sissy boy. We are working on how to get his wife fully on board with having lovers and fucking them in front of her husband. She has been coming with her husband to our sessions for the past several weeks. Last night, this phone dominatrix arranged for a bull to fuck his wife. My bull was black with a 13-inch-thick cock. I watched Alex fluff his cock and guide it into his wife’s hungry pussy. I watched his wife have an earth shattering orgasm too. It is great when I help submissive men, but when I can help their wives too, I really feel like I have done my job well.

Taboo phone chat is where i got a new sissy trained with Sissy panties

Taboo phone chat is where I met my new sissy. He played like he didn’t like someone to tell him what to do and put him in his place. I knew he was; I could smell a sissy a mile away. I gave him a look and told him to kiss mistress feet and dropped like the proper hoe he is.

Taboo phone chat

I gave him some pink Sissy panties and told him to put on what a bitch like him deserves to wear. I had just gotten fucked by a big black cock, so i had a pussy full of creamy load. I grabbed his face, and I told my new sissy bitch that his job for mistress was to be a Sissy maid and needed to clean all my cummy messes. I grabbed my sissy bitch by the hair and rubbed her mouth all over my cunt. She opened her mouth, and I squeezed some left-over nut right in her mouth. After she swallowed it she went to lickin! She licked mistress’s cunt so good I came inside her mouth before I was all the way clean. Mistress gypsy will give this sissy the best training.