Category: Sissy training

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 feminization for sissy whores

Forced feminization

Forced feminization is for sissy whores. You’ve never dressed up like a sissy whore before? Well, I’ll rebuild you from the concrete dust and up. I’m going to take away everything that you’ve ever stood for as a man. I undress you and force you onto the floor, my heels digging into your should blade. I’m your new phone dominatrix and whatever I say goes from now on. I’m going to force you into some extreme sissy girl training. I pull out my favorite pair of sexy lingerie see through, now sissy panties, and put them on you. I dress you up in a training bra, and some sexy 6-inch-high heels to go along with it. Those look so sexy on you! I force you to prance around in that sexy lingerie. I then put a frilly dress on you and tell you that you had better wear that outfit for my guests that are to arrive soon or else I will push you to the breaking point in this sissy humiliation training session. Sissy slave training is what I do best I tell you as I lay down a huge dildo on the bed, I inform you that my guests are coming equipped with strap ons and that we are all going to have so much fun with you. I hear the doorbell ring… Are you ready for what I have instore for you?

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!

Sissy Maid: Follow My Instructions

Sissy maid training


A sissy maid that is employed by me has to do a lot more than wash dishes and do my laundry. Obviously, you will be doing any chores I assign to you, but I have a few extra activities that a regular maid will not do. You will require extensive training before you can really be called my maid. You have to take corporal punishment well, even if you haven’t done anything wrong. Sometimes I just like to spank your ass. You also have to be in a chastity cage every minute you work for me. You are more of a sissy slave than a maid, and no slave needs to be getting off without my permission. In addition, a maid must be willing to vet all of my sexual partners thoroughly. That means you’ll have to be good at taking a hard fucking. None of the men that I have ever fucked (and they are few and far between) got to fuck me before showing how good of a lay they are. You don’t have to do anything but let them use you and rip your pussy apart. Once you have been sufficiently degraded, you need to report back to me how good he was. If he’s shit, he might need to practice on you until he gets it right. You’re okay with that, aren’t you, maid sex slave? 

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.

Gotcha Professor; A Sissy Phone Chat Roleplay That Will Make You Hard

Sissy Phone ChatSissy phone chat will suck you in when you are a cross-dressing faggot craving the penetration of a superior women’s strap-on. I know that when you admire a beautiful woman it is not the sexual desire of ravaging her body that plagues your mind. Instead, it is envy that pierces deep within your soul knowing that you, a man, just wish you could be in that pretty lady’s clothes. That is why whenever you show up at that college party, I can tell by the way you are looking at me, Professor, that you want to be naughty but not like all the other professors with their horny teacher’s assistants. 

It doesn’t take much convincing for you to take me back to your place. A single-person basement efficiency. You make good money working for the school, so why live in a dump like this place with thrift store furniture? I know it isn’t because of fancy clothes, because you would rather dress like a whore. However, the air smells of sweet perfume. Hookers. You do like to get your rocks off. You have no wife so it must be an embarrassing fetish that keeps you blowing your bullseye with women of the night. 

You lead the way to the bedroom showing me to the bed before excusing your way to the bathroom. Lingerie hangs ever so slightly from the top drawer of your dresser. Now I can’t help but snooze, stepping up to my red healed platform wearing feet and slowly and quietly pulling out that drawer. It brings a subtle giggle to my sexy lips. Panties, and lots of them. Some bras too. Inside the drawer was a variety of pretty panties all tangled up as if they were having an orgy of their own. You enter the room mid-conversation pausing, words stuck on your lips. Slowly I hold up a lacy pair of purple panties lined with a lilac silk pouch that would be against a pretty puss. 

It’s honestly adorable the way you stumble over your words slowly sulking closer to the ground. Your panties are still in my hand as I slowly walk your way. I reach down and lift your chin, ordering you to your knees. Gently I kiss your forehead and order you to dress up nice and pretty for me and you may get a reward. I order you to show me the rest of your toys, and of course, you do holding up a big 10-inch black strap-on dildo. I can hardly hold my excitement as you dress in your best lingerie. All the naughty nothings that I will be doing to you with this deep dick penetration of mine. I’ve got you now professor, you are mine all mine.

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!

Mistress Phone Sex Raine Brings The Pain!

Mistress Phone Sex

Mistress Phone Sex goddess Raine will own you today! You will be my sissy faggot cum dumpster whether you like it or not because I’m your Mistress and I demand absolute devotion! I know just what a disobedient little sex slave like you needs, the firm hand of a dominant goddess to put you in your place. Down on your knees little faggot! Don’t look up at me unless you’ve got two cocks in your mouth and one ramming that sissy pussy open. I will make you beg for cock as you get completely owned by my strong hard cocked friends who want to use you like a cock sleeve. I’ll stuff you to your limit and train you to take it like a good little cum dump. You will be a good little sissy faggot for me or you will feel my wrath of anal pain!

Sissy Humiliation Training for Faggot White Boys

Sissy humiliation training is exactly with a little pathetic shrimp dick panty wearing bitch boi like you deserves. Let your new Mistress train you to be a good little nigger cock worshipping sissy faggot white boy.

Understand your place first and foremost. That is before me, Your Mistress and on your knees in panties. My desire is to make you a good cock sucker and I have a nice big black strap-on cock to train you on. As it is I would be ashamed to have you fail at being a good cock sucker for one on my black studs. So get that suction cup BBC dildo and start sucking it bitch.

The moment you are ready and able to really get sloppy with this cock is when I will be ready to train you on taking it in that sweet pussy of yours.

Sissy humiliation training