Tag: Best sissy trainer

Punishing My Sissy Cum Slave

Sissy pantiesMy sissy slut Cassidy pissed me off the other day. She disobeyed her mistress and removed her plug before I gave her permission. To make matters worse she didn’t even use her mouth to clean it like I like all my sissies to do. She was nervous her wife might find out about it. Just for that I locked her little clitty up in an extra small cock cage and made her wear her pink frilly sissy panties home to her wife. I also put my inflatable ass spreader in her and filled it all the way up. For good measure, I made her suck on a cum ice cube on the way home too. I want her breath to smell of fresh cum when she goes home to kiss her wife.  I hate it when I have to punish my cum sluts but this mistress doesn’t take kindly to disobedience. This little sissy will learn to understand that her wife is not the one she needs to be afraid of. 

 

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 training involves me

Sissy training

You know sissy training is my jam, and I love it so much because I can put whatever kind of twist on it I desire. I’m the girl you want to learn from and to be honest I have quite the lessons to show you. Im going, to be honest. Porn is a godsend. It will show you what men love more than anything, and in my eyes, that’s pussies and boobs. Naturally, you don’t have a pussy, but you have an ass pussy, and that will do. Im going to enhance your fake boobies and help you dress to impress. iM GOing to make all the straight men give you a shot. Im a pro like that, and you will see plenty of cock for your sissy holes.

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!

Taboo Phone Chat Gets Dark For Bad Sissies!

Taboo Phone Chat

All sissies get to endure my taboo phone chat role play when they misbehave and my dark side comes crawling out of the depths. I will bend them over a breeding bench, and have a huge fourteen inch fuck machine come in to act out my rape fantasies on their little assholes. Meanwhile, they’re being force fed hot cum straight from my Cum Cow farm, and I’m torturing their poor little clitty. Consider it your second circumcision but this time, it’s going to fucking hurt a lot worse. Let’s shave off that last inch or two, and leave you with a flat little piss hole! Go on, get the grinder so I can end what’s left of your “boyhood” before we forget you ever had balls for good. Oh your balls! Yes, those come away next. Let me get my sewing scissors.

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?

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 Girl Training For a Fairy Princess

My caller wanted Mistress sessions with me. He knew I specialized in Sissy girl training. Fairy Joe didn’t wat to succumb to her true fate of being a sissy fairy princess. She was so very reluctant. The thing is, the choice of panties sissy Joe wore told me all. He said he just liked how they feel.

I know panties, silky panties feel nice on those dicklets. It’s true they are stimulating for the squirties. The thing is, silky panties come in all style and colors. When you choose the frilliest of panties in pink your secret is out.

Sissy Girl Training

My fairy princess sissy Joe is coming round so well. He is succumbing to the sissification and embracing her girliness. I make her up with pretty colors on her whore face and make her wear pretty bras with silicone inserts. She gets waxed and wears pantyhose. We dress Princess Joe so pretty and I take her to the club.

Forced sissy training