Category: Sissy girl training

My Sissy Cuckold Husband

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Today was all about me. I had my sorry ass husband and sissy work together to please me. I first had them put on pretty pink panties and little knee highs and Mary Janes. They looked so pretty. They ran my bath water, brought me champagne and strawberries, washed my body and shaved my legs. They then dried me off and applied lotions and oils to prepare me for this beautiful creature that would be joining me tonight. As they made dinner, I picked out the perfect outfit. The bell rang and the sissies answered the door and brought him to the table. After we ate, they had filled the garden tub for us. Me and this handsome fellow undressed and got in the tub as the sissies brought us drinks. We then made our way back to my bedroom where my husband was waiting on the end of the bed. I snapped my fingers and he came over and started stroking my date’s cock until he was nice and hard. I then laid back and spread my legs. My husband knows that he is to lick me from ass to clit exactly two times to prepare me. He did an excellent job. I then nodded at my husband and he walked my date towards me and gently guided his big thick cock inside my juicy warm pussy. My husband then stood there and watched as this man fucked all of my holes, filling them with his warm thick cum that he knew he was going to clean up once we were done.

Such a little bitch

best sissy trainerI met the biggest little bitch the other day, he was the most feminine man I had ever seen and yet somehow he was in denial of his feminine side. He kept saying that he was a real man and he wanted to fuck me but what was he gonna fuck me with? The barely one inch long little clitty he kept calling a dick? Yeah, no thank you on that. I decided to show him what he really was so I forced him to dress up and I brought in a big black guy to show him what he really wanted. I showed sissy that big black cock and said now this is a real dick! What you have is nothing and little sissy bitch boy started to cry. I made him suck that big black cock until he came and you know what? It made him realize what he really was… a little sissy faggot!

Sissy Training With Yours Truly

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Now that the dressing up part of your sissy training is complete, it’s time for you to learn one more really important thing – cock sucking. I know you’ve thought about it before, and maybe you’ve even pushed a dildo down your throat and sucked it. But that’s not the same thing as having someone else present. Someone who won’t go easy on you when you start to gag because you’re not used to having something pushed that far down your throat. I understand that you might be nervous, but sometimes you just have to throw caution to the wind and go for it.
You’re not going to get any sympathy from me, nor will you be babied by me. I’ll push your wannabe whore ass down onto your knees and tell you to open your mouth. If you don’t, I’m just gonna spank that little clitty of your until you beg me to stop. Trust me, choking on a cock is much better than getting your naughty area spanked. Are you ready to obey me and open your mouth so you can learn how to properly suck cock? If you don’t, it’s not going to be good for you, you nasty slut. So just open wide!

The Best Sissy Trainer Took a Night off to Get Some BBC

best sissy trainerEven the best sissy trainer needs a night off. I had a date last night. Been forever since a man took me out properly. The Covid virus has put a monkey wrench in dating. Even just hooking up is a challenge nowadays. My sissy boys helped dress money last night. They even did my hair and my make-up. They may have been born male, but they have no masculine characteristics. They made mommy look extra hot. It was fun to get gussied up too. I have spent months at home with my hair in a ponytail and no make-up on. My date was a handsome black man named Tyrese. I met him months ago and we have texted daily while on quarantine. He loves sexy white milfs. He is ten years younger, but he is no gang banger. He is a college professor at one of the universities in town. Smart, handsome, financially secure and hung? I won the fucking lottery. We had a great date. Neither of us wanted it to end, so I invited him home for a drink since no bars are open yet in my state. My sissy boys were hiding. They knew how excited I was to get some big black cock again. I did not spring my sissy boys on my date yet, so they stayed quiet and watched as their sexy mommy got some big black cock on the couch. I was making a lot of noise because he was huge, and I had not been fucked in too long. I enjoyed Tyrese and his cock for a few hours. When he left, I summoned my sissy boys into the living room. They do not need sissy slave training. They knew what to do. I parted my legs and let them get their creamy reward for making mommy look so sexy.

Sissy Panties Sniffer Steve Is a Dirty Slut

Steve’s panty sniffing confession and love of sissy panties is a little different from my norm. He called me all worked up over how much he loved to sniff his girlfriends daughters panties while wearing a pair of his girlfriends panties. He liked to sneak a pair out to wear around when she was at work. When the daughter was off working or at school he would find her freshest worn pair of panties. He’s suck on the crotch and sniff it. He really became obsessed with her when he caught a glimpse of her fucking her boyfriends big black cock. She was so hot it made Steve get a boner. He was already wearing his girlfriends (her moms) panties and loving the feel of them. But when he saw her teen daughter fucking that BBC he was mesmerized and obsessed. He wanted to taste and smell her cunt after she had that BBC and the only way he could do that is find her soiled panties that hopefully had the cum and pussy drippings in them. He’s coming around to asking his girlfriend if she would fuck a black guy for him. He wants to watch up close as that big black dick spreads her blonde milf pussy open. I really hope she agrees to this.

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He Had To Be Punished

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So, my boss today made the mistake of correcting me in front of the office. He knows better than that as I am his mistress. He knew he had fucked up and immediately hung his head, but it was too late. He knew he would be punished. As soon as I got back to my desk, I sent him an email to meet at my house at 6pm and to be prompt. The bell rang and he took his required position of kneeling in front of my door. I left him like that for thirty minutes before letting him in. He tried to speak but I shushed him quickly. I instructed him to put on the outfit I had left in the bathroom and to crawl to me. He did as told and crawled to my feet. I motioned him to rise and turn. I then admired his pink silky panties, knee highs and Mary Janes. I put him over my knee and started spanking him, over and over again until his little sissy ass was bright pink, and tears ran down his face. I then pulled down his panties and rammed a big jeweled butt plug in his ass. He puckered as I pushed it in further. I told him he would be wearing those panties and the butt plug tomorrow. He lifted his eyes in compliance as I pushed the remote and the butt plug started vibrating. I think tomorrow will be a fun day. Don’t think he will be sassing me anytime soon.

I’m the best sissy trainer for you

best sissy trainerI’m the best sissy trainer for you sissy and I think you know it.  You can’t have a nice Mistress because you will walk all over her, that’s why you came to me. You need to be controlled by a bitchy, mean woman and that woman is me. I won’t sugarcoat it for you sissy, when you are wrong I will tell you so. Remember what happened when you were rude to me? I forced you to go out in your sissy slutwear in your own neighborhood and you were caught by your boss. Remember how embarrassing that was for you? That still wasn’t enough to shut your disrespectful mouth so I had to get real creative. I had to set up a huge gangbang for you and leak the footage of that to everyone you knew, that sure got your attention didn’t it? Now you are respectful as hell because you know a bitch like me can ruin you in an instant.

Sissy Training Mama To Help You Suck Cock

My proud moments as a Sissy training mama are when that Sissy gets her first feel of a real mans cock in her mouth. The throbbing head of a hard dick slipping between her pretty sissy lips. I’m always anxious to hear about that experience and love the excitement in your voice. My sissies always makes mama Diana happy. I’m a proud mommy knowing that you got to enjoy that experience for the first time. What beats sucking your first cock, is the joy of seeing, touching and tasting that first big black cock. Yes, I know the thrill, and I also know that many of you are still anticipating that experience. It will happen for you. But what is more amazing is to get your pussy penetrated and fucked by that first dick. The feel of your cherry getting popped while you are dressed all sweet and sexy. You put in so much effort dressing for cock and I am a proud mama that you finally got your anal virginity taken by a real man.

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Proud of Femboy Training and My Sissy Sons

femboy trainingJune is Pride month. And I am proud of my femboy training daughter and sissy boy sons. The reason I am a sissy trainer is because I have sissy sons. I knew early on that they were different from other boys. I have a 20-year-old son from my first marriage. My daughter is 18 and she has the same daddy as my oldest son. I had twin boys in my 30s from a fling. I decided to raise them a single mom. At the time, my daughter and older son were young teens, but they could help me out with babysitting occasionally. When it became challenging, I quit my job as a professional dominatrix, and took a s job as a sissy phone sex operator, so I could work at home and be around more. That was when I noticed my twins were into things other boys were not. I had been a dominatrix and sissy trainer for decades; I knew the signs, even in young boys. They were taking my panties and wearing them, but not jacking off in them. They just liked the feel of the silk on their little dicks. They also had more fun playing with their older sister’s old Barbie dolls than their big brother’s Legos or Matchbox cars. My daughter recognized the differences too. She was a natural sissy trainer, so I made her my protégé. Together, we raised twin sissy boys. Something we all share a love for in this family is big black cock. My daughter and my sissy boys have black spade tattoos above their pussies. It is a sign of ownership to black men. I love big black dicks, but no own owns me. I may be a great BBC sissy trainer and I may love BBCs in my pussy, but I am a dominant woman. I do however, love turning sissies and young girls into black cock whores. I understand if you cannot be out of the closet like my twins, but I am here to help you be proud of you even if I am the only other person who knows.

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Call Upon Your Mistress For Forced Sissy Training

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So, I have this friend who was always talking about how he wanted to be feminized, but he never took any steps to do it. I got really sick and tired of hearing about it. He’d tell me he wanted nothing more in the world but wouldn’t take any of my suggestions. I did get him to dress up in lingerie one day and let me take pictures. I told him that once he saw himself all dressed up and sexy, he’d get more excited and want to move the sissification process along. But that’s not exactly what I had in mind.
Of course, he tried to back out of our plans, so I told him that if he didn’t go through with his feminization, I’d show everyone in his life the pictures of him in lingerie. I didn’t really WANT to blackmail him, but he gave me no choice. It took a few weeks to get things done, but once his forced sissy training was complete, he was very happy. And it wasn’t just the dressing up part that I helped him with – I taught him exactly what it means to become a sissy. Wanna hear more about that? Give me a call and maybe I’ll help you, too.