Tag: mistress phone sex

Best sissy trainer gets you addicted

When you have been trained by the Best sissy trainer, you become a cum addict. All you think about is the next moment mistress Gypsy will use you to milk a BBC. Since I work with BBC trainers I will always keep you full of cum. I want you in your sissy uniform I have picked for you and on your knees waiting to serve us in any way. Tonight I wanted to have you dripping before you milked any cock. I love seeing what a good cum whore you are. We teased you by making you suck on each and everyone of our toes like they were dick you needed to milk. I made you lick my asshole while my BBC trainer friend put his toes inside your Sissy panties and teased your sissy pussy. That had your clitty hard, especially when he shoved his toes in your pussy. You start begging me to let you milk my BBC buddy. As I laugh, I open your mouth and guide your head on his thick long cock. Right away he face fucks you hard, making you gag and choke until you have tears flowing down your face. Your little clitty leaked through your panties and when he started filling your mouth up with thick yummy cum, your clitty squirted. That shows me you are an addict to the cock.

Best sissy trainer

Sissy Training is My Specialty, and So is Being a Loving Mommy

sissy trainingSissy training is my specialty, but I get a lot of mommy calls too. I guess you could call me a sissy mom. I have two trans sons. When I first started this job, my boys were schoolboys. Just young boys who liked to play dress up in mommy’s clothes and play with make-up. I knew then that they were special. I mean boys their age played with cars, Legos and trucks. They wanted to wear jeans and t-shirts. I let them be who they were. I think it is harmful to stifle a young one’s natural exploration to find out who he or she is. Most women are not as enlightened as me, though. I get all sorts of sissy phone sex callers who talk to me about how they were shamed and ridiculed, even punished by their parents when they got caught wearing mommy’s pretty things. Some of these men are pretty fucked up because their parents just did not understand.

I like to recreate the mothering experience with callers. Be that nurturing, loving, encouraging mother that they should have had. The kind of mother my boys have. My twins are living their lives in that in-between world that scares so many people these days. They go to an arts school where their creativity  can blossom. They go to a school where they can wear dresses and makeup to school daily. They have friends. They have boyfriends. They thrive socially. Regular school was not so welcoming, but I recognized that immediately and switched their schools. What mother does not want her offspring to thrive? When they are 18, they can decide if they want to have sex reassignment surgery, or become trans girls. Whatever they choose, I will support because that it what a good parent does. They support their offspring. And the best sissy trainer supports you. Nurtures you, encourages you and only punishes you in order to train you properly.  Mommy is waiting for you boys.

His first Sissy training session went well

Sissy trainingThere is a new sissy in town and he’s going to be squeezing his little link into his first pair of Sissy panties! He was at work when his asshole started feeling all slimy, he couldn’t help the tingly sensation that ran through his body.. He needed a fix, even if that meant in the parking lot of his place of employment.. Risky business! He took his 15 and called me up from the back seat of his compact car..

He didn’t have any toys so we settled with his fingers! He slicked his tips up by slurping and sucking them, like they were a fat cock.. Then smacked the excess saliva that he scooped up from his chin onto his manhole.. The windows of his car were not tinted but they did naturally fog after a while of his huffing from the sensational fuck he was giving himself; while I whispered humiliating things into his ear.. He or should I say she?

Anyway, the faggot is aware of his position.. Not every call will he get off; sometimes he may even just have to sit back and listen to me breathe.. I mean whatever it takes to talk to a hottie, you couldn’t stand a chance with in reality! uhh, the good in fantasy, huh? haha, Sissy training has only just begun, we went shopping for some fun stuff..

So far we’ve gotten a clear 7.3in soft realistic dildo to gag his bussy with and a plus size contrast lace mesh slip with a matching thong… It’s even got a satin bow that sits right between his knockers. I can’t wait until it arrives so I can show the world that a Sexy BBW does exist.. His juicy phat ass is going to look amazing sucking up a g string.. He has never had his man hole stretched with anything besides his finger.. Lucky him, I am the sexy bitch who’s going to break him in. Welcome bitch, You’ve got yourself the Best sissy trainer on the net, Good taste!

Sissy Gurl Mistress phone sex

Mistress Phone sex

 Nothing gets my sweet MIstress phone sex pussy off more than making fun of soft bitches like you! Laughing and teasing your ass for being such a limp dick little sissy cock loving faggot.  I had so much fun the other day with you confessing to me how much of a sissy faggot you are. 

Zoey Knows you couldn’t wait to tell your Daddy all about me when he got home today. I heard all about how he surprised you with a super cute new outfit to wear for him and we had a couple of his daughter’s friends come over and laugh and make fun of you while he bent that tight ass over and made you whine like a little whore as he pounded you in my brand new short, tight mini dress. And I got even more turned on as the girls laughed and called sissy la-la a cock loving little faggot when his Daddy put her on her knees and blasted a weeks-long load he was saving up, all over that femme face.

There you are dressed up like a whore in a tight pink little mini dress, with a wet, throbbing, gaping, freshly fucked asshole, completely covered in cum, with three of the hottest little sluts laughing at your ass calling sissy all kinds of names, putting slut girl in her place, as a submissive, crossdressing, little cock whore. Thank you Sissy fag boy for letting me take your confessions and sharing my love for cock. I just wish one day I could be right there watching and laughing at you whining like a slut from getting pounded by a stud’s big cock! Thank you for allowing this Phone dominatrix to work you over SIssy Gurl! 

Calling All Sissy Girl Training Applicants!

Online Sissy Training

I don’t just train any curious faggot that comes into my chat, I train only the best sissy girl training applicants! I’m an exclusive online sissy trainer and I demand your utmost devotion to our training sessions. When you are mine, I will make you the best little sissy panties slut that you can be! I’ll have you strutting your stuff in high heels and kinky lingerie in no time! I’ll own all those perfect bimbo fuck holes so only the best cock will do when it comes to fucking my pretty sissies. You’ll have a great time shopping for clothes and cock with me and when we are out and about, you’ll be on display like my perfect little sissy cock tease! Mistress phone sex is just the beginning! We will find some hard BBC to please and make a game out of who can take that big dick the deepest! You will love having Mistress Raine as your best sissy trainer BFF!

Humiliation Phone Sex: ON your knees like a little bitch!

Humiliation Phone SexLet’s play a game little dick, one of humiliation phone sex roleplay fun. We will pretend I am the prison warden and you are the little punk prison bitch meant to be sodomized at my will. That means you will have to be a good little snot and obey each and every command I give you or your back pussy is going to be beaten to fuck by lots of thick studly man meat. I’m sure the thought of you being gangbanged by that many studs makes your widdle dicky twitch a little in excitement anyway. 

You can start by worshipping the ground and the sexy heels I walk on. On your hands and knees put that pretty little ass in the air for all the prison guys to look at and cat all. Kiss my heels. Suck on my heel like it was a cock that you were trying to bring pleasure to. Kiss up my legs wrapping your thighs around my heel so I can step on your pathetic bean bags while you thank me. You are lucky to serve my perfect hot young body. 

Service my perfect ass hole. Perhaps if you are lucky I might place a toot on your tongue. Men would line up to lick my anus and you are doing it for a chore. Let me use your tongue like a dick fucking you deep inside my ass. Lord knows it does more for me than your worthless little dick does. If you are a good little worthless worm you can lick my ass hole while one of my prison studs services my dripping wet cunt. We may even laugh as I drown you in my squirting pussy juices from fucking his perfect cock. No cumming for you of course otherwise you take my stud next time.

 

Online sissy training with Tiffany got kinky

Online sissy trainingHer first week crossdressing was a success! We’ve already found her a BBC Master to keep her tamed.. She is a slave to his Big black cock, left with no choice but to surrender when he destroys her bussy and leaves her with a creampie!

She has adjusted quite well to her new duty as a Sissy slut being dominated by an alpha male.. She called me up for intense Online sissy training and sent me some personalized photos so we could work on getting her up on as many sites as possible. This made our hunt for the biggest cock we could come across, easier…

She’s already been anal stretching for a while so she is no newbie to ass play. She has just finally accepted her fate, being better at servicing a man than a woman.. Plus, she’s already done so much damage that she has managed to destroy her nervous system.. her dick has shriveled up and shrunk about 3 inches.

These are the consequences sissies accept when they find out how good an anal orgasm feels. To her I am already the Best sissy trainer in existence.. Yet, training has only just begun! She seems to take orders quite well and isn’t a mouthy little bitch. Sometimes sissies forget their purpose is to serve and tend to be far too needy. She’s quite different. She knows I am who she idolizes and in order to be the best she can be she is going to have to follow my lead. In due time she will have what it takes!

Bareback breeding is my gift to her whenever I see overall improvement. An entirely new wardrobe is what we are currently working on, all she needs is guidance. Forced feminization isn’t necessary!

Best Sissy Trainer Coraline is Part Phone Sex Therapist Too

best sissy trainingI am not so egotistical to say I am the best sissy trainer here, but I am one of the best. I think what makes me good is that I am equal parts sissy trainer, mom and phone sex therapist. There is no cookie cutter sissy caller. You must know how to listen to a sissy when she is talking. Some do not want cock, some are all about the cock. Some want sissy humiliation, others want encouragement and nurturing. Some like to dress up in frilly dresses and be exposed as sissy faggots. Yet others just want to wear panties and stay in the closet. A good sissy trainer does not treat all her sissies the same way. I am part sissy phone sex therapist. I listen to my sissies. I help devise a sissy plan that best fits them. Jake for example, lives in a rural city. He wants cock, but it is hard to get cock in a small town. It is also hard to dress up and go to glory holes when your town has no glory holes and everyone in town knows everybody else. I have been encouraging Jake to travel. He finally did and he called me from San Francisco the other night. He wanted some encouragement on where to begin. In a large city full of gay men, sissy faggots and all kinds of alternative folks, Jake could blend in. I sent him to a glory hole first. I found an adult bookstore near his hotel and instructed him to go there. I was with Jake the entire time. He wanted me to hear him suck his first real cock and I did. I was like a proud mama bear. My months of sissy training finally being put into practice. It was hot hearing Jake swallow cock after cock. I helped Jake get what he wanted out of the sissy life. His journey is just beginning, however. Maybe I can help you with your sissy journey too.

Sissy humiliation training Size Queen

Sissy humiliation training This sexy vixen delights in sissy humiliation training. You should all know by now that I’m a size queen mistress who keeps it as real as she can for you. It serves you no use for me to deceive you or make you feel better about your tragic disability. Besides, come to think of it, I’m the one who deserves pity. What am I expected to do with your tiny cock? Even the term “little” is praise. It’s more like to a guy clit. A disappearing micropenis. It’s pointless massaging or sucking it to get it hard since even hard, it’s a pitiful small pathetic pinky.

Sissy Humiliation Training for small dicks


If this big dick queen is going to devour a cock, it had better be a long, thick hunk of meat! Have you got it? No! I also don’t want to see you jerk your puny winky in front of me, foaming at the mouth and gyrating like you’re having a seizure. Disgusting!

Here’s what I do with guys with little dicks like yours. I dressed you in pink pantyhose and crotchless sissy panties with a little hole in the back for your male pussy. I tell all the Alpha males I know that I have a special sissy girl that needs her ass cherry popped for them to fuck. You should see all of them line up! They understand that if this huge dick lover is pimping out a sissy fag like you, you must be one of the worst losers. And they like assisting their favorite size queen and mistress phone sex in degrading and humiliating little dick sissies like you!

Just being honest! All sissy sluts and faggot prostitutes, unite! It’s time for you to come out of the closet, and I’m just the cunning whore who can bring you there. Nothing excites me more than preparing you to be the sissy girl of your fantasies. I also specialize in: spanking, pegging, sph, bisexuality, smoking, foot and shoe, and BBC, as well as chastity, bondage, humiliation, teasing, and denial! 

Mistress phone sex whore Remi

mistress phone sex

 

I found a cute, little sissy bitch in need of a hot, mistress phone sex trainer to teach him how to take dick! I could tell from the start that I was going to have to be mean to this little whore! He was already dressed up all girly and slutty with thigh highs and a sexy thong. He had a nice, thick buttplug popped in his sweet, tight fuck hole but that wasn’t enough. My sissies are bbc sluts so they have to be ready to take the biggest and fattest cocks. I made that little slut ride a huge, fat dildo and stretch his sissy pussy wide open! I kept telling him what a pathetic cum whore he was and laughing at him. He looked so desperate and sad, bouncing on a dildo and dribbling drops of precum everywhere. I noticed that whore was making a mess on the floor so I started slapping him around and demanding that he clean it up. I made him stop riding that fat fuck toy, take it out of his whore hole and use it to scoop up the sticky cum that was all over the floor. Then I made that little bitch lick and suck the dildo clean for me while I kept telling him what a little bitch he was and how I owned him. I had so much fun with my new slut and I can’t wait to make him take a real cock tonight!