Category: Sissy training

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

Sissy phone sex confessions

Online sissy trainingWhen did you recognize it? Did you just realize this recently or had you known all along? Don’t pretend to be confused, you know exactly what I am talking about, don’t you? Don’t doubt yourself.. Yep, it’s the first thing that came to that slutty mind of yours. Maybe you are still having trouble accepting it.. You don’t like being called a faggot, in no way are you gay.. Right?

Even though you slip your penis into a pair of sissy panties nearly everyday.. Still nobody has a clue! Aren’t you so tired of hiding the truth? The first step is confessing.. Don’t worry I will clear that fog up for you. You come to me for acceptance.. You love the idea of a woman encouraging you to suck and slurp..

Sometimes you may even use the excuse you want me to enjoy myself, it’ll seem as if you are sacrificing me or your girlfriend to get our pussies stretched by a BBC.. Its safe to say, you only do that for your own personal pleasure.. You keep in mind when I orgasm all over his cock you can use the excuse of being a slave for me.. That’ll make it possible for you to clean his cock up of all my sweet juices.. Manipulation?Sissy slave training

In reality we both know, you want what’s inside his gusher.  You are hoping I get so aroused watching you drag your tongue up and down his cock that I enable you to bend over.. You want your man pussy to be loaded with the creamiest thickest cum load.. I guess that’s what I am here for… To be the one who tells you it’s okay that you are intensely attracted to big cocks.. Some men have big dicks and guys like you just have little ones!

It’s totally understandable, you want to find out what it feels like to have a real man’s dick in your hand ! Maybe even have a better understanding on why your “prude” girlfriend suddenly is a nymphomaniac when it comes to a big black dick.. its okay, want to see a magic trick? kneel down before me and watch my tight snatch swallow up an 11 inch dick.. Meanwhile, I want you down on your knees sucking my cunt juices off his balls and dragging your tongue up and down his cock as it slides in and out of me. It’s time for Online sissy training… WBMT offers the best Sissy slave training on the web!

Let Me Show You Sissies How It’s Done

Femboy training

I am disappointed in all of you. Man after man have come here to run through all of my students and you still don’t know how to please a cock correctly. Come watch me and I will show you what a real sissy whore will do. Before I do so, however, I’m going to put you all in chastity. I don’t want you all to get distracted rubbing your clits while I am teaching you valuable skills. When you get down on all fours, look back at him while he’s fucking you. Even though you are a disposable cum rag, some guys like to see the cum rag’s fuck faces. Squeeze his cock when he is completely inside of you, so that he never wants to slide it out. Do your exercises so that you can hold onto that cock for as long as you can. Unless they ask for your gaping hole, no one wants a loose pussy. I see you’re all hard in chastity right now. You had better not touch your clits until I’m done getting fucked!  

Sissy Panties: What color do you like wearing?

Sissy PantiesSissy panties always need to be worn when a pretty little plaything is in the presence of a hot young Princess like me. I can smell pathetic sissy losers in the air whenever a sissy faggot is well within range. Brainless sissys need to feel the silky panties against their little winky, it feels way better than fake men’s boxers. They can be so rough, a real puss needs panties after all. Catching a sissy wearing fake man clothes will result in caged punishment and withheld cum. There is nothing worse to a sissy bitch than knowing that he has to look and not touch. Why even push the envelope, put your panties on, and ring up the hot young mistress of your dreams?