1,510 results for sissy training

Sissy Phone Chat Goddess

sissy phone chat

Are you in desperate need of some sissy phone chat? Maybe you’re new to the world of feminization and you need someone to talk it over with. Not every sissy is the same, so sometimes it takes a little bit of time to figure things out. Do you want to just be a cross dressing sissy who only gets dressed up? That’s totally fine!  Maybe you just want to feel feminine from time to time while you masturbate. Maybe you’ll just rub yourself through your panties, but maybe you’ll also want to use a dildo on your boy pussy hole.

But maybe you want to go further than dildo play, and you need some help with that. Honey, if you need to learn to suck cock and play with real men, I am totally the perfect person for that kind of sissy training, too. I know you’re going to be very nervous, so I would be more than happy to assist you with that. I can’t wait to be there for you on your sissification journey! It’s my favorite thing in the world to do, so take a chance and get on the phone and give me a call now!

The Best Sissy Trainer for My Nephew

best sissy trainer

This week my nephew visited. He is a sissy, and I am the best sissy trainer for him since I am family. He was only supposed to be here for a weekend, but he does not want to leave now because he can be himself with me. My brother is not as liberal as I am. My nephew is a sissy. There is no denying that, but my brother is one of those folks who would disown his own son because he is a cock sucker. So, when my nephew is with me, I let him be himself. I encourage men to be themselves. If you want to wear panties and suck cock, why should I do anything else but support you and help you achieve happiness?  I have trained my share of sissies in my family, including my twin sons. I know what I am doing. One day this week I brought home a playmate for him. He was already dressed in his frilly dress and had been practicing his cock sucking on my dildos. This guy is older and a good friend of mine. He is hung, and very alpha male. He loves young jailbait sissy boys. I told him about my sissy nephew, and he wanted to be his first “daddy.” When I introduced my sissy nephew to my friend, his sissy stick grew in his panties. He liked him.  Terry is a handsome man. Clean cut, well-dressed, intelligent, handsome and has a 9-inch cock. I helped my nephew take his first real cock in his mouth and in his sissy hole. He is a natural. He just needs some sissy training to be the best sissy he can be. I assured him that if he got kicked out of the house by my brother, he could live with me. I may not be able to help you if your wife kicks you out for being a cock sucking sissy, but I can be your sissy trainer.

sissy training

Meet My Sissy Slut

Sissy TrainingBecoming one of the best sissy trainers wasn’t easy when I came from submission but I learned really quick where men like you belong. That is down on your fucking knees keeping my pussy clean of hot loads with your tongue! Have you got what it takes to become my sissy bitch? Takes massive sized cocks, little cocks, any cock I think you deserve after I put you in a sexy outfit and matching stockings and letting those same cocks fuck your tight shit hole?  You need to suck every last one and make them cum in to your ass! I don’t care if you don’t like the taste, stick your fingers in your ass and suck that cum off your fingers!

Sissy Panties Play Party – Caught!

Sissy panties
What in the BBC fuck do you think you’re doing? You and I are both aware that this is not even close to the first time that I have walked in on you wearing a pair of my soiled panties, with another pair nearly attached to your nose as you sniff up every little splash of juice my ass and pussy have left inside them. You were wearing the best pair of nylons I own, stroking your cock with my silky, black stockings.

And you’ve been playing in my make up!? Why the fuck do you smell just like my French Whore perfume? Are you a little sissy faggot, really? Honey you have to be honest with me me about anything and everything. If you’re wanting to learn exactly how to take big black cock, I’ll help and train you! You won’t take that cock only only down your throat but up your little fuck hole, I’m more than happy to assist.

You and I both know that I am the Queen of sissy trainers, that I will force you to be my sissy now that I’ve caught you in your little panty play party. You just love being a pathetic little sissy don’t you? You wanted me to catch you all dressed up, playing in your little panty party, didn’t you? You wanted me to absolutely violate you didn’t you? Grab my big black strap on. It’s time for a cock size session.
Sissy Girl Training

BJ Throat Training!

Sissy training Audio
Open up wide! It’s your turn to try swallowing down massive black cocks for me. I know you want to just be the perfect little sissy and it’s so hard when your tiny clitty is so achey. That’s why we had to put it in that bright pink cage honey. We can’t risk you letting that leaky goo out, now can we?

Now fix your lipstick, and swallow all eleven inches of that cock straight down your throat right now! No talking back, just gagging on massive black dicks. Cock size training is part of the gig sweetie, and I’ll fucking force you if I have to. I take worthless fag husbands and turn them into perfectly useful sissy cum dumps! There are three holes I use on a sissy, and yes i mean three!

If you get too leaky, you’ll need a little sounding to even you out. What’s sounding? Oh, it’s when I take a rod and shove it up your piss hole. Then, I like to electro stimulate those balls and make sure you get ooey and gooey. It’s time for a prostate exam, and I’m setting you up for failure because I will punish you if you cum!

Mistress Phone Sex

Sissy Jay

Forced feminizationEvery Man with a small penis needs a little Forced feminization and Sissy Jay loves coming over to play with me and my boyfriends. See he is a bit shy when it comes to the ladies and I always know its him when he hits my cyber chat with.. “Is..Is this the way to the… small boys room?” It’s true my little sissy has a little pecker that makes him want to be a bonafide female. An easy target for a girl who loves to mess with men who have no dick and are so shy when it comes to talking with women. 

Little sissy Jay was at the bar scoping out women, but it’s not what you think. I knew from that look he didn’t just desire to get laid by a sexy bitch, but he wanted to be a sexy bitch. Now my girl who was helping me pick a guy or two for us to fuck while we were having some drinks elbowed me hard and said “Oh My fucking god, that’s my brother!”, as she pointed to him. I made a little pecker sign with my hands and said ”You don’t mean your “little” brother?”  

He saw me and  I could tell he was bright red and tried to make a quick exit, but we stopped him at the door and decided to walk him to his car. 

“I just think it’s so sexy when a man has a cute little cock Jay, why don’t you come to my place and we can play dress up?” The Fun part is during our Femboy training Jay the sissy fag loves getting all pretty and doing sexy twirls and admoring her new look. And is never one to turn down learning how to serve bull cock with me or his sister!femboy training

Our chats rates are the same as calls!

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Looking for Sissy Phone Sex?

sissy phone sex

Looking for sissy phone sex? You are in the right place because I am a sissy trainer. I started my adult career as a professional mistress. I have a dungeon room with a closet full of BDSM equipment. After Craigslist closed its adult personals, I moved to Back Pages to advertise my services, but then they got shut down by the government. I was SOL for advertising my dominatrix services. I still had many regulars, but I wanted more money. That is when I became a sissy trainer and joined this site.  While I was busy being a professional dominatrix, my twin boys were becoming sissies and I did not realize it at first. I never noticed panties disappearing. Eventually, I caught on and felt badly that I missed some sissy training opportunities. I made up for it. I understand older men discovering they have a sissy side and needing to keep it covert because of family and work. That is why I do online training. But with my boys, there was no need to not let them thrive as their true selves.  I sent them to the performing arts school where they would fit in better. I helped them dress. I get them dresses and skirts. They wear panties too. At their school, they are accepted as femboys. They suck cock. They take boys to school dances. They live their lives as girls mostly. Once I found out they were sissies, I used all my knowledge to help them transition to their new world. I got them their first cocks. A sissy trainer also knows plenty of men who will let boys and men suck on their cocks. Since I started as an online sissy trainer, I have learned more from my callers that helps me with my sissy boys. If you are a full-time sissy or just a part-time one, online sissy training can help you. I can help you.

Presley Dresses The Sissy Dollies

Forced Sissy Training

I love my sissy dollies almost as much as I love taking thick Alpha cock. My favorite thing to do with them is play a sweet game of dress up! My sissies thrive off of soft, feminine fashion since their goal is to be sweet sissy sluts. Not all sissies have to be thin little sticks, so I keep thicc bitch lingerie around too. Every sissy is required to dress a certain way to even think about playing in my presence.

We start by shaving the entire body except the brows and head hair, and slipping them into silky, skin tight stockings. They have to have smooth legs to spread while they take Bull Daddy cock. Sweet, crotchless panties to ensure easy anal access and a sweet garter come next. My favorite sissies get hormone replacement therapy to shrink down those useless clitties and grow in some hot tits.

I have plenty of dresses for my sweets to slip in to before giant BBC’s slip inside their throats and their anal fuck holes. Faggot holes I like to say, until my sissies become hot Tgirls. That will be the day! But they have to start somewhere, so my dollies love playing dress up with me.

Humiliation Phone Sex

Fag training!

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I love getting new slaves! They always come over so innocently but I can always tell if they are secretly craving a big black cock! little sissy john came by as I was getting my tight fucking pussy stuffed by my next-door neighbor BBC. John’s cock got so fucking hard as he watched me get stretched open by a real man not some little bitch with a 3-inch cock! It was so cute seeing him try to jerk off his little clitty I just laughed at him and demanded he come suck my neighbor’s cum out of my cunt. Like the good little whore he was he obeyed my orders and started to lick up every last drop! My neighbors cock was still rock hard and got behind john rubbing the head of his cock on john’s ass! My little sissy fag couldn’t help but moan as cum oozed out of his tiny little cock! John left after my neighbor used him as a cum dumpster a happy little fag!

A Treat For My Sissy Slut

Mistress Gypsy I have been busy getting together a whole bunch of cocks and balls all kinds of varieties. I know how much of a sissy slut you are and I know you will be excited for the treat I have for you. Before we start, I want to dress you up like a filthy slut.

Sissy training

In a mini dress and no panties with knee high stockings and heels. I’m going to show you off and get you on your knees to lick and suck my asshole. I will shove your tongue in my asshole while I play with my clit. I won’t stop until I squirt all over your face. Then I will send you off to go get fucked and used by all the cocks I collected. I want to see your face get fucked and used until it is dripping with cum. It won’t stop there I want your man pussy used and filled up too just like the dirty cum dumpster you love being my good sissy slut. That is why I wanted to give you a treat.  Mistress Gypsy will give you treats when you deserve them.