1,508 results for sissy training

Put on those Silky Panties

best sissy trainer

Michelle tells me that I’m the best sissy trainer that she’s ever had. Michelle came to see me and he was dressed in blue jeans, a sweatshirt and work boots. I raised my eyebrow and told that girl to strip out of that crap right away. He had men’s white briefs on too. I cut them up in a bunch of tiny pieces. Then I put her in lavender silk panties and a white silk nightie. I made that girl put in a thick pink plug and stretch her pussy for later use. She whined but her clit was standing out all hard.
The next training that I gave to Michelle was cum eating. I didn’t want that sissy to embarrass me when she got cum from a real cock. I took a cum covered strap-on and fucked it into her lips. God, that lazy slut hadn’t even made her face up before she came over. I smeared the jizz all over her face with the strap-on and let it dry. That’s how I made her go out shopping. She had a tiny nightie, panties and dried up cum on her whore face. She’s almost ready for real dick now.

Cucksucking 101

Sissy Girl TrainingWatching a sissy suck cock can be so amusing. The cock hungry little whores just try to swallow the things which may make the guy cum but won’t necessarily be a mind-blowing blowjob. It lacks a key ingredient that linger with a man after he gets his dick sucked. That my sluts is the art of the tease. If you want to ever be considered among Arabelle’s darlings then you will listen to my advice and learn to utilize it. Any man can find a whore on a street corner to devour his cock for a quick 5 minute nut, but a real woman no matter how salacious have class. I can give a man a blowjob that will have his mind reeling because I know how to take my time. I know how to use my skills to tease every inch of his cock and balls. While still catering it to what he likes. You need to listen to the sounds he makes, test out his super sensitive areas and see how you can make him squirm beneath you for a change. That’s how you become the best cocksucker you can be.

Stevie gets her Clitty Spanked

Sissy Girl TrainingYou see those nice acrylic high heels I am wearing? And those short shorts and cut off tank top? Those are things that my sissy Stevie begs to wear. But Stevie has been a bad girl. She has become quite the little slut and can’t get enough of pounding her little man pussy with her big black dildo. Normally that would not be a problem, but Stevie leaves her little clitty messes all over the place and never cleans them up. So today I decided that Stevie was going to learn to clean up all her little cunnies and as a reward she could wear this outfit of mine she so longs to wear. We started by removing her butt plug and inserting a remote-control dildo, that will vibrate whenever I press the button. Stevie put on some satin panties and we sat down to watch her favorite shemale porn. Less than 5 minutes in and she had already made a mess. I ordered her to clean it up and she back talked. I pulled those panties down and smacked that clitty with a wooden spoon a few times and told her I would continue until she cleaned up her mess. Tears filled her eyes as she licked them all up. I then started the tape again. Same thing, 5 minutes and back talk. More clitty spanking and then finally she cleaned it up. She is a tough one. I then turned on that vibrator and started the tape again but this time I didn’t stop it as she made mess after mess after mess. I told her not to touch her mess, just yet. After her panties were soaked and it was running down her legs, I took them off and put them in her mouth to chew, therefore forcing her to clean herself. I got her a fresh pair of panties and put back on the tape. I told her that we will continue all night if we have too. After a few pair of fresh panties and a few more clitty smacks she was immediately cleaning up her cunnies. As a reward, I removed my outfit and let her wear it. She looked beautiful.

I’ll Train You, Baby

sissy slave training

You keep saying that you want to be a sissy and that you want to serve me, but you keep finding excuses to not do it. Well, that is going to come to an end today. You are going to get on the phone and call me for the beginning of your sissy slave training. I know it might be a little difficult since you’re so defiant, but I have no doubt that I can reign you in and turn you into the sissy slave of my dreams.
I don’t care if it’s against your will. You are going to learn to do everything you need to do to become the perfect woman. Sure, you have to learn to look the part, but it’s much more important that you learn to suck cock. I’ll invite a few of my friends over every day. Oh, and don’t you worry, my sissy slave – I’m not going to get you just any cocks. I will get you the biggest and most delicious cocks you’ve ever seen. And once you master sucking cock, I’ll train you to be able to take huge cocks right in your brand new pussy. Don’t keep denying what you’re meant to be. Call me and I will train you to be the best sissy slut you can be.

Some Boys Just Need Phone Domination

phone dominationWhen you need some phone domination, call a sexy sissy trainer like me.Often times, men need cock control. I am the key holder for many men. Having a  cock is a privilege and you should not abuse it. If you can’t stop rubbing your nub, then you need a mistress. If you are a chronic masturbator with a small nub, you need to be in a pair of panties. I love training sissies, cuckolds and small dick losers. I have this peeping Tom neighbor named Larry. He thinks he is being discreet, but I have cameras all over the place. Even when I am sleeping, I know what everyone is doing. Larry has a tiny dick, yet he was yanking it hard outside my bedroom window the other night. He could never get a girl as hot as me. Hell, he could not get a girl half as hot as me either. I got a pair of sissy panties for him, and paid him a visit last night. He lives alone. No surprise there. I have never even seen him with a woman. Now, if he had a decent cock, I could just cage his little pecker and help him learn some self control. Larry was born to be a sissy. He didn’t agree. That was until, I put him in my panties and pegged his loser ass. Normally, I am more of a nurturer, but Larry is a fucking pervert. He is jacking off as my daughter and I sleep. He needed put in his place. I am not sure if I was too convincing but I did peg his ass hard. I made him a sissy bitch for about an hour. I’m not done with Larry yet. He needs more sissy slave training. I will make him soon realize what he was born to be. 

Sissie Loves That BBC

BBC Sissy TrainerI know sissies love that BBC as much as I do, but sissies must be trained to control themselves. I am the best BBC sissy trainer there is and I knew I could train Susie. So, I asked my favorite BBC Fred to come over. I dressed Susie in some pretty pink panties and matching lipstick and told him that he was to watch as I played with that big black cock and to never move his eyes from mine. I know this will drive him crazy as he will want to look at that gigantic beast of a dick. I sat Susie down on the floor in my room as I undressed Fred and myself and got down on my knees to admire that big black beauty. My god it is so wonderful. I could see Susie trying to divert his eyes and quickly reminded him that his eyes were to remain on me. Susie watched me take that massive beast deep in my throat as Fred proceeded to fuck my throat hard. As soon as he came in my mouth, I held that giant load without swallowing. Susie had been so good that I motioned him over and opened his mouth and dumped my mouthful of big black cum into his. I made Susie hold it in his mouth until I told him he could swallow. He did so without hesitation, so I wanted to reward Susie. I let Susie clean Fred’s massive, beautiful, black cock with his tongue. I was so excited watching my training being successful that my pussy was getting wet. I think I will take that BBC in my pussy next.

Hypnotized For Daddy Santa

sissy hypno training

I bet all you sissy bitches are ready to get dressed up for the holidays, aren’t you? And you say you want to suck cock, but you just don’t seem to have the courage to go through with it. That’s why you’re going to call me for sissy hypno training. I’ll get you ready to suck the most festive cock of all – that’s right, it’s Santa!
But first you’re going to need to be hypnotized. While you’re on the phone with me, I want you to lie back in a quiet, dark room. I want you to focus on your breathing. Breath in for five seconds and then out for five seconds. I need you to be really relaxed. I’m not going to tell you the exact process here, but when I’m done with hypnotizing you, you’ll be putty in my hands. You will be in your sissy glory and wondering why you weren’t on your knees in front of Santa before now. You’ll get over your nervousness AND you will surely be on Santa’s VERY naughty list. That’s the list you want to be on. So, you’re welcome for that. When you’re ready to become the sissy you were always meant to be, call me!

Forced Feminization Of A Small Cock Loser

forced femination

This Christmas I want to make you my little Sissy elf Bitch. That’s right some forced feminization will do you good for the Holidays. I bet you really want to be a woman anyway, don’t you? I want to help you in that progress and make you the best little Helper Santa has ever had. I will teach you how to drain those Jolly balls of his so we can deck the Halls with loads of cum. That’s better than snow for my naughty elves that desire to be Sissy sluts to big Jolly old men. I think you are just in time for the best part of training. A nice peppermint candy cane will feel so good up that new vagina of yours and the gooey cream down your throat is the best egg nog of the season. After all Santa is an alcoholic and addict, so you know that cum is a party whores favorite thing.

Let’s Get That Boy Pussy Ready

femboy training

If you’ve found yourself in need of a little bit of femboy training, you have come to the right mistress. I love taking boys and turning them into feminine fuck toys. That’s what you want, after all. You want to get all kinds of feminized and get that boy pussy fucked, don’t you? Well, that’s part of the training. I’ll have to get your pussy ready for the real cocks that will be sliding deep inside you. I’ll give you a few fuck sessions with my trusty strap on cock and you’ll be cock ready in no time!

But first things first – you need to make sure you look the part of a femboy. Maybe you don’t want to go fully feminine and that’s okay. We can add feminine elements to the way you already look. Black nail polish, eyeliner, and a nice pair of lacy panties will be a great start. Oh, maybe even a pair of fishnet stockings over your panties. Who doesn’t love those?! Your lover will be turned on and you’ll feel sexy as hell.

If you’re ready for a woman who can help you with the extensive training you’ve been craving, let’s get this started, sissy slut!

Put Your Panties On

sissy girl training

Do you find yourself in need of some sissy girl training? I can totally understand. Being a girl is hard and of course, it takes more than just looking like a girl to actually be one. Don’t worry, though. You are in the right place and I promise you that you will be trained and ready to take on the world as a sissy slut. You will be the talk of the town by the time I am finished with you!

You are in the perfect hands with me. I know how to transform you into the sissy girl you want to be. I can help you out with the looks part of things. See, that’s really the most important part. It matters that you feel beautiful and sexy. Trust me, when you look and feel the part, it’s going to make getting down on your knees for that man so much easier. Once you are all dolled up, everything else is going to come so naturally to you. And if it doesn’t, that’s okay. You have me as your sissy trainer to teach you about all the fun things to do to a cock. What more could you ask for?