Category: Online sissy training

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!

OMG! You Just Woke Up as an Anime Girl!

Sissy training audio

 

In this listening session, all you need to do is sit back, relax and listen to the sound of my words. 

You slowly wake up and stretch, ready to get washed up and dressed. As you get up, you notice your body feels different than usual. You look down to see what is going on and you see a massive pair of tits on your chest. You run to the bathroom, desperate to see if someone has pulled a prank on you as your giant tits bounce up and down with each step. With one glance, you realize that you have been transformed into a beautiful anime girl. You have big bouncing boobs that jiggle when you breathe, a tight slim waist, and a nice round ass. You are ultimately feminine, beautiful and fuckable. You walk out of the house with your night clothes on, consisting of only a see-through white tank top and tiny shorts, and you capture the attention of all the men in the neighborhood. Seeing you in this outfit makes their cocks hard and they rush after you. You try to go back inside, but it’s too late. They have already grabbed you and started ripping your clothes off. 

You can’t fight back as they fuck you every which way. They stuff their cocks in your pussy and your ass, something you have not experienced before. Your new virginity does not matter to these men as they use you as a cock sleeve. One of the men starts playing with your tits, squeezing them and bouncing them up and down. No need for that as the men behind you are pounding you so hard your tits bounce on their own. Open wide! An army of big cocks are ready to force themselves down your tiny throat. 

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! 

Be my sissy

phone domination

Do you want phone domination by a goddess who will make you quite the sissy? I know you want to be able to suck cock freely and become a full-time sissy. Let’s get you over to hustlers so we can get you some outfits to try on. You’ll be my sissy slut and be fucking for the dollar. Most sissies like to have a firm, stern goddess to guide them. You know I am the epitome of tough love. I am not mean because I want to be; I am only trying to make the best sissies possible. Only the strong will make it and can conquer all the sissy tasks put in play. When you do what I say, you become one of the greatest sluts.

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.

 

Forced Sissy Training With A Goddess Will Show Your True Colors!

Forced Sissy Training

I love training my sissies and dressing them up in all sorts of sexy and slutty outfits. Making them wear slutty dresses and super slutty make-up and super high, high heels is only part of the joys of sissy training though. The rest is all about who we get to join in on our naughty fun together. I always have a ton of guy friends willing to break a new sissy in.

Or we could go to the club to break in the new sissy pussy. Knowing full well that your erect clit is only that, a clit not a cock. Maybe I’ll even put it in a little chastity cage so you won’t be able to touch it, just simply enjoy being fucked and squirt while that enormous cock pounds your pussy hard. Let me watch as it drips in excitement, and you get stuffed full of cocks.

I have both shemale friends and male friends who would both be open to popping your cherry my love. And you’ll love every fucking second of being used like the sex puppet you are. You’re my little sex doll that I get to make over and dress up then have fucked silly. I want you fucked so good that you call me for more, longing to be a better sissy than before.

My online sissy training will leave you drained and squirting like no tomorrow. So get in line and pick your favorite dress and we will have some naughty fucking fun.

BBC sissy trainer lets me use his sissy slut

I love when a BBC sissy trainer let’s me take over. I love making a sissy bitch fall to her knees and beg me for anything especially to suck a big black Dick I love knowing I can use a cock and a pair of cute pink panties to control you. You will pay me to degrade you and put you in your place just like your big dick trainer. When I get spoiled that is when I give you the best commands. I might task you into sucking 10 big dicks and you will do it because part of your slave training is that you must do anything I want. Last night I planned a blow job party with all my favorite BBC friends. Like a good bitch you wore what I made you wear and you pranced around like a horny teenager waiting for the moment you got to suck dick. When that moment came you didn’t let me down. You sucked all their big black dicks until they were dry and empty of semen. Your clitty leaked all over your Sissy panties the whole time you took every drop of semen down your throat.

BBC sissy trainer

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!