Category: Online sissy training

Best Sissy Trainer Loves New Toys

Best Sissy TrainerI see I have a new brat to tame tonight don’t I? Your pretty girlfriend sent you in here right? Oh yes, she’s lovely indeed! I got to have some fun with her this afternoon and sucked her pussy as she told me all about you! hahaha! Quite the screamer too. She said you were nothing but a little pansy bitch just waiting to become who you really are. So, are you ready to become the sissy you deserve to be so you can stop disappointing that sexy girl of yours? Get on your knees! Crawl naked on the floor for me on all floors! Those pink panties are laid out just for you little faggot. Try them on and come out to meet some new friends!

Forced Sissy Training 4 my bro

forced sissy trainingIt’s only a matter of time before I give my brother some forced sissy training. He is a smaller sized guy who already looks a little effeminate to me. All through highschool girls asked me if he as gay. I would say that I didn’t know. But the more I learned about life, and sissy training. I began to suspect he was very much like our father. Is being a sissy inherited? I always noticed panties, stockings and bras going missing. I would get into a fight with my mother that my father was yanking his cock to my underwear. She would punish daddy until she told me that she was satisfied it wasn’t him. It really dawned on me one early Saturday morning. I hear the sound of a vibe coming through the walls between me and my brother’s room. I decided to creep next door and see what was going on. And as I turned the doorknob and slide in his room, I was rewarded with my brother on his hands and knees teasing his butthole with my Vibe! He didn’t even notice I was there! “Keep it.” I giggled. He was so embarrassed telling me it wasn’t was it looked like and that he wasn’t gay! “I know you’re not, you’re a sissy,” I said with enthusiasm. My brother still denies that he needs sissy girl training, but we shall see. I love forced play of a sissy whore!

He Needed a BBC Sissy Trainer

I am a bbc sissy trainer and so is my daughter. She is 18 now and wants to be a sissy trainer and dominatrix like her sexy mommy. She has shared some of my BBC lovers with me over the years. And I have shared quite a few of her black boyfriends with her over the years. Last night, one of her black boyfriends was over when I was training a sissy. This sissy has never expressed interest in black cock or any cock. This sissy just wants to dress up and be my sissy maid. That all changed when my sissy went upstairs to use the bathroom and walked by my daughter’s room. She did not have the door completely shut and my sissy bitch saw her sucking on her boyfriend’s big black cock. My sissy came back downstairs and started drilling me about the guy upstairs. His clit stick was bulging in his nylon panties. I excused myself for a moment and came back with my black suction cup dildo. My daughter’s boyfriend is not into guys at all. But I know plenty of black men who think any port in a storm will do. I texted one of them that I had a sissy bitch who needed stuffed. While I introduced my sissy to my black dildo, she came alive. She was no longer interested in being a sissy maid. She wanted to be a black cock sissy. Well, she was in the best company because I am the best sissy trainer for BBC faggots. She sucked on my black dildo for awhile before she asked for the real thing. That was on its way. My black lover arrived 20 minutes later and broke in my sissy’s ass with the real thing. Nothing feels better than a real BBC in a sissy’s ass. Or my ass either. And just like that as sissy went from a maid to a bbc sissy faggot.

Joy To The World!

Sissy Training

The end of the year is the busiest time for a sissy slut trainer like me! I talk with all my sissies daily about their holiday party outfits, gift choices and make up combinations. I even spend time talking about cock sucking quotas. That’s right, my sissies are extra giving during the holidays, they are excited to get a cock sucking quota of at least ten fat cocks a week! They linger at the gym, at family gatherings, after work parties and at gloryholes waiting for their opportunity to suck a mean dick and tell me about it later, they know I live for the dirty details. Why do they do it? Simply because they know that Mistress Raine wants her sissies slurping and deep throating all December long to bring joy to the world!

Sissy Maid Training for the Holidays

sissy maid training

For some reason, some of you who call me for sissy maid training think that you’re going to get out of doing the actual maid work. When a man brings a sissy maid into his home, it’s NOT just for cock sucking and fucking. So, you need to just get comfortable with the fact that you’ll be doing more than looking cute in your outfit. Your new Master might want you down on your hands and knees scrubbing the kitchen or bathroom floor with a toothbrush before he fucks you. And if that is what turns him on, then you’d better be down on your knees doing as you’re told.

Once you’ve done your chores, then you might get lucky and get his dick shoved down your throat. And if you are a VERY good girl, then you might even be permitted to swallow his cum. But if you resisted him in doing your chores, you might still get that load, but he might shoot his load on the dirty floor and make you lick it up from there. I think the best thing for you to do right now is call me so we can get you trained properly!

Mistress phone sex with Miss Remi

mistress phone sex

 

Mistress phone sex is my favorite way to have fun! I love telling stories about what I do with my sissy bitches. Last night, one of my favorite little, sissy sluts came over to see me for some kinky play time with his favorite mistress. I had a date planned but this sissy bitch is such a good cock sucker and such a cum thirsty, little whore that I just had to use his slutty mouth. I had him suck and stroke my date’s fat cock until it was rock hard and throbbing for me. I got so turned on watching his throat getting fucked so hard! He watched me ride that massive, fat fuck rod until I drained my date’s balls into my hot cunnie. My little cum slut  was begging me to lick up that creamy load but I made him wait. I wanted to feel that creampie drip out of my hot pussy while he cleaned my date’s cock off with his dirty whore mouth. I even got a hot video of my cum slut, sissy bitch licking my pussy clean while my date pumped him full of cum! I’m going to be watching that while I wait on my phone to ring.

Get Dressed

 

mistress phone sex

Time for a pool party baby. I am having some friends over and you and my hubby are going to be the entertainment and pool faggots. Go on into the room and I have laid out the sweetest little slutty maid outfit for you. A hot short, pleated skirt with matching corset, a black thong, breastplate and black thigh highs and heels. Oh, and I put a pretty Christmas tree butt plug beside it too. Make sure you push that all the way into your pussy babe. Then put on your lip gloss and get out here.

Oh, my look at you two. Perfect femboys. Now get to work. You know what to do. Grab your trays and make sure everyone gets their drinks and appetizers and whatever else they want too. Oh, and don’t forget the poppers, you know how much my friends love those. Come closer. I whisper in your ear that your mouths and man pussies are available too. Don’t disappoint me and don’t embarrass me. As I sit back and sip my drink I marvel at my party. Then I see you both performing lovely.

My hubby on his knees sucking a big black cock, which he loves. Practically worshiping it. I can only imagine the little clitty leakage occurring as he devours it. You? Well, you are bent over the table. Skirt pulled up and taking a big thick dick in your tight pussy as you also suck a cock in your mouth. You both look marvelous. I could use another faggot for my party. Do you think you have what it takes?

BBC Sissy Trainer Heaven

BBC sissy trainer My little sissy cum sluts are trained to be the perfect BBC cum whores just like their sexy Mistress. I put my sissy on a leash and caged up his tiny clitty. Mistress Heaven has a surprise for this sissy slut. “I have a surprise for you that I know you’re gonna love my beautiful sissy,” I told her. Before she could ask any questions, I commanded that she open her big mouth nice and wide. I completed her slutty leather outfit with a new toy, a slave punishment mouth gag with nipple clamps. Her pretty red lips looked so plump and sexy in her new toy. “Assume the position” I instructed. My obedient sissy slut bent down and got on all fours. I pulled out my next surprise, a huge hollow tunnel butt plug. I inserted it into her tight sissy asshole. She whined and tensed up. “You better get used to the feeling of having your tight little man pussy stretched open babe. All good sissy pussies are always wide open and ready to be used at any given moment.” That’s when I brought in my final surprise a BBC friend of mine who just happens to love breaking in new sissy sluts. “You’re going to be the best sissy and lick my sweet pussy while my friend fucks your boy pussy with his giant black cock,” I smiled. I spread my legs for my sissy as my friend rammed his cock into my sissy’s hollow asshole. My pretty sissy obeyed my instructions while her tight ass got used and fucked. She sucked my wet pussy as my friend’s massive cock filled her juicy, stretched out man pussy with hot sticky BBC nut sauce. “Let my beautiful cum whore clean you all up, friend,” I told him. My friend nodded and pulled his hard, shiny cock from my sissy’s wet asshole. He removed the mouth gag and replaced it with his BBC. “I want that dick all cleaned up, sissy,” I directed. “You’re going to be a BBC pro by the time I’m all finished with you,” I smirked.

The Best Sissy Trainer for Christmas

best sissy trainerGive yourself the best sissy trainer for Christmas. The holidays are right around the corner, and you deserve something for yourself right? It can even be our secret. I have plenty of closeted sissy boys. Most of my sissy callers and clients are married with respectable jobs where imagine is important. What happens with us during our time together, stays between us. Unless you piss me off of course. I have a private sissy client I see in real-time. I have known him for over a decade. He was my divorce attorney. One of the best in the industry. I saw something in him. He knew what I did. At that time in my life, I was not doing sissy phone sex yet. I was a dominatrix. My ex-husband was trying to blackmail me into getting custody of our offspring. I knew if he got custody, he would send our sissy boys to some alternative conditioning school where they could not be themselves, so I hired the best lawyer. He became one of my first sissies. We have had a decade relationship, but he recently tried to black mail me into free training. Like that shit is going to fly. He had no power over me. Being a sissy trainer is not illegal. My sons are trans, and young teen boys, no one can take them away from me. He was trying to black mail the wrong woman. I have nothing to lose, but he has everything to lose. I sent him an email of him in frilly pink dresses and bonnets getting spanked and sucking cock. Over 10 years together, I had a ton of photos. I told him one push of a button and I would send them to his firm, the American Bar association and his wife. I am severing my relationship with him too. I mean you cannot blackmail woman who is providing you with sissy training and not expect her not to fight back. I am a nurturing and sweet sissy trainer, until you cross a line. Then you will pray you had never met me.

Sissy Adult Diaper Lover

sissy phone sexI have the cutest little sissy who is an adult diaper lover too! I have been working on that part of him that needs to be nurtured and cared for and wearing a big stinky diaper for me. I call that a two-for-one when I get a sissy who needs to be humiliated in a diaper. That’s a two-part humiliation my loves! I just love feminizing a man all the way down until he is now a little girl in a fancy pink on it and a little pink bloomers with a big bottle full of cum juice right in his little cutie pie lips or should I say her lips? And that little dicky poo is just a cute little clitty tucked away in a diaper. And being a sissy trainer / Mommy I know that it’s important for my sissy to get as much nourishment as possible! Cum and cock and mommys milk provide that! Especially an ABDL diaper loving sissy little girl! And my boyfriend has a big black cock that he doesn’t mind using as a bottle so that my sissy can drink right from the tap! Are you supposed to sissy who loves diapers and needs to be humiliated?