1,509 results for sissy training

Harold and Arabella’s Fun in the City

Sissy TrainingSissy training is so fun!

Every little sissy wants to be just like me but being a perfect Barbie girl takes practice!

I know you have a tiny little, not worth mentioning cock between your legs! It really is the sadist thing I have ever seen but if you are going to be a princess like me, you need to learn to forget about that little willie!

I am going to dress you in the prettiest dresses and the sexiest lacy panties. I know they feel so silky against your skin and that makes your dick want to ooze that half a spoonful of spit But don’t! You will be punished for doing anything other than what you are told!

I had so much fun with the last sissy in training. He oozed his micro meat juice and ended up wearing nothing but sissy panties and thigh highs carrying a glittery sign through the whole city for everyone to see, “Sissy in Training”!

I made him introduce himself to all the construction workers and muscle bound thugs coming out of the gym and the big strong police officers! He had to wiggle his pretty little sissy ass and talk in his sweetest little princess voice and when he did not do it perfectly, his punishment was sucking a big police cock in the back of the patrol car!

At least he thought that was his punishment…his real punishment is me telling everyone who reads this that he is a prissy little sissy, right Harold?

Magic Pecker Puffers

Sissy trainingYou know you have a tiny little sissy dick!

It is so small, even little birds have swallowed bigger worms!

It is the perfect size to stuff in those pink satin sissy panties but you know you could never satisfy a girl!

My friend Zoey and I know exactly how to make that garbonzo bean grow!

We have decided we will help you,,,just because that is the most pathetic excuse for a cock that we have ever seen! But you must do exactly as we tell you!

I want you to stroke that micro-meat until it gets hard, It should only take two strokes at the most! Come on! Stroke it until it gets hard! Oh, that is hard? We may need more vitamins!

I pry open that tiny dick eye and slide a big fat multi-vitamin down your shaft! Yes, it hurts, but you know what they say- no pain, no gain! We have eleven more to go!

Zoey, listen to him whining after only three! That is so pathetic!

There is another option for the wimpiest little pricks!Sissy phone training

Zoey is strapping on her straight shooter. My daddy should me how to use this when we used to impregnate the horses on the farm!

We will load all these growth pills in and she will pound your tiny little ass until it is pumped full of magic penis puffers!

Tell me how much you want that strap on! Tell me how much you want your tiny cock to grow!

Beg her to pump your ass full of pecker puffers!

She is fucking your tight little ass so hard, you hadn’t even noticed she had already unloaded all her goods in your brown eyed fuck hole! And your still begging her for more!

So you are trainable after all!

Princess Zoey, Your Phone Dominatrix

Phone dominatrix Princess Zoey is thrilled to be your bratty sissy owner! But that doesn’t stop me from being a phone dominatrix when you really need some one on one time with me. My clit gets hard and big , just like your clitty, when you have to spank yourself for me. Your Mistress had you call me because she knows you need to be in complete submission even when she isn’t looking over your shoulder. That email I got today? She said she caught you wearing her lingerie and stroking your clitty through it! You didn’t even have a panty liner on to keep it clean from your boi juices.  Oh, you are so naughty! Then you are going around acting like a spoiled brat because she took away your boy clothes and is going to make you go out in public in your sissy dress. Yes, Mistresses often rely on  PRINCESS online sissy training to keep bad boi sissy sluts in line. I own my daddy and I know just what to do to get you in line! I know you are locked up tight sitting in a hard back chair rubbing your caged clitty all over the back as we have our session. Most sissy slaves are honest to a fault. I make you stop and go get the fly swatter. Twenty smacks to your cliity cage! I demand you to stop sniffling and bend over the chair and give yourself twenty more fly swatter smacks on each sissy boi ass cheek. I love hearing you disciplined at my command! Then I tell you that I want a gift card code or else I will email your personal mistress and you will be punished so much more. Either way my cunt will be satisfied, your pain or something new and shiny for me! online sissy training

Frocked and locked

forced sissy training

Directly disobeying me will result in forced sissy training every single time! When I told Sissy Sam to go to work wearing panties under his suit everyday I meant it! Random inspections will be done, not that I told him first. But I needed to see, and when I got to his office he sputtered and tried to be angry. But I would not expose him if he let me see his undergarments for the day. Just as I suspected, cotton men’s briefs.  That required an allowance increase for me! Shame sissy shame, Pay piggy! I pulled a jeweled butt plug out and told him to bend over and gave very little lube and pushed it inside his little ass. It was tight and now he had to wear it all day! I bet his employees thought he was constipated. I giggled as he came over for a session. I had promised that he just might let him fondle my perky breast and play with my pussy. But instead there was a billowy pink sissy uniform and a brand spanking new cock cage. I had a list of chores for sexy sissy Sam once he was dressed. So pretty in his new cage and butt plug don’t you think? First we painted my toenails and gave me a leg rub, on his knees of course! And next we watched some sissy porn so I could watch that cage get tighter on his clitty. Oh how it swelled and leaked! But I still had some sissy maid chores, like scrubbing the floor with that ass in the air, so he could get used to exposing that tight sissy ass! My sissy would obey me, and at the same time learn the basic steps to become fucked and go through forced feminization until he metamorphosed into a full flagged sissy whore! 

forced feminization

Never Lie to Your Phone Dominatrix

phone dominatrixWhen you do not listen to your phone dominatrix, you get your clitty caged. Currently, I have two bad sissies. Both made me promises that they did not keep. In fact, they both tried to lie to me. I require proof of tasks. A simple photo tells me if you did what you were told to do or not. I am not a dumb mistress. I am college educated with a Master’s Degree in Psychology.  You cannot take a photo off the Internet and pass it off as you. I will find it. There are a ton of reverse image finder programs. Both sissies begged me for online sissy training. I took my time to design tasks for them so they could advance and become the best sissies possible. What did they lie about? They told me they went to the glory hole when they did not. Both sent me pictures of them sucking cock, but I found those images on the Internet from years ago. These two sissies do not know each other, but they played the same games. I am a nurturing sissy mom, but lie to me or betray me, you get the cage. I made each loser lying sissy bitch buy a cock cage. They balked of course, but I am not afraid to blackmail an unruly sissy slave.  Most sissies who called me are married or they have corporate type jobs that would laugh them to the unemployment line if they knew what they do behind closed doors. I demanded pictures in their cages. I told them where to get the cages online, so I could verify they purchased them. Each sissy emailed me their receipt copy and a week later, sent me pictures in the exact models they purchased. If you want sissy slave training from me, you must do what you are told. Never lie to a sissy trainer or you will end up on the Internet too.

Heaven Is Your Mistress

Best sissy trainer Hey are you ready to begin sissy training. These courses are not for the faint of heart. You will need to be able to handle intense sissy training. We begin with giving you a crash course in cuckolding. As your master I will put you to work and make sure that my team of hot guys with big dicks abuses all your holes. Can you handle all these guys and their big ten inch cocks. I hope you can handle all the pressure of taking it in the ass while sucking cock at the same time. Can you keep up with what I’m going to put you through. If not need not apply. This intense sissy training will include humiliation and bondage. So don’t be a wimp when I give you your lessons. We have slot of work to do let’s get started. I want to be your ultimate sissy boss. I will get off on you being fucked in the ass.

Phone Domination on Lock Down

phone dominationPhone domination does not violate any stay at home orders. Many states are slowly getting back to normal, but adult places will be the last to resume operations. You may not see an adult bookstore or a glory hole open for a while. In the meantime, sissies still need to work on being good sissies. Lori is a long term sissy of mine. In fact, she is a sissy I trained in my home for years. She can no longer come to my house for training. She has become one of you. She must call me for her training. I will not let a sissy slide just because the world is on lock down. Lori is working on her cock sucking skills. She was about to get the real thing in her sissy holes when the world imploded. I had a big black stud lined up to fuck her sissy pussy and her pretty mouth. It will still happen. It just must wait. In the meantime, I sent her some big black dildos. Some from my private collection because she is a special sissy. Not that you are not special. It is just that Lori has been with me for 6 years. I know what you are thinking. Six years and just now about to get cock? Not all sissies are cock whores. Lori started off as a sissy maid. She just wanted to wear pretty things and take care of the best sissy trainer she knew. She would clean my house and worship my pussy and ass whenever I wanted. Lori was married when we first met. She wanted to be a sissy badly, but she did not want to cheat on her wife either. I could work with that. I respected that. Last year, sissy Lori got divorced and she knew that meant it was time to embrace the sissy life in its entirety. Until she can get that big black cock in her sissy holes, she is practicing with my dildos. I do not care if you are a sissy maid or a cock loving sissy faggot, online sissy training keeps you in sissy mode.

Sucking Your First Cock

Sissy trainingStanding at 8 inches from base to tip, he’s cock is hard and thick, so attractive how could you not touch it. Slowly stroking his shaft, gently rubbing the big swollen head feeling it’s soft warm skin. Go on, kiss it. Feel the heat radiating against your lips. Rub that puffy head all-around your lips, then part them and give it a wet kiss. The tip of your tongue getting your first taste of cock, sends electricity through your body, doesn’t it? Making your own clit dick harden. If you like that, you’re really going to like putting his whole head into your mouth and gently sucking it. Keep both hands slowly stroking his shaft while your mouth makes sweet love to his head. Go ahead and moan, letting those sweet sounds waves vibrate against his cock. Follow his direction, as he starts to push into your mouth, open up. Let his cock into your mouth as far as you can take it. Don’t panic, breathe through your nose and focus on the taste of his cock, the texture of his hard shaft. Focus on the salty droplets of precum the dribbles from his head. Keep in mind you are the cocksucking slut here. The only thing you need to be thinking about is how good it feels to have a cock in your mouth. How wonderful it feels to be the special little slut with a quality cock in her mouth. Before you know it you’re in a trance engulfed into your own feelings and arousal only to be brought back with that explosive power in your mouth when that perfect cock cums releasing his creamy cum for his little cum slut to gobble up. The taste becomes an addiction and you a new addict, you’ll be crawling back and begging for more real soon. You sluts always do.

Heavens Fantasy

 

 

best sissy trainer

I love watching gay men suck dick. Are you ready for your sissy training? Im taking on beginners right now. They come to my place once a week and I make them ready to be little cock sucking sissy sluts. My favorite sissy boy Lilac came over yesterday evening. I brought a freind with a 10 inch cock for him to suck. We put Lilac in gorgeous lingere and a long black wig. I instructed him to start sucking the BBC on his knees. And he obeyed. I told him to deepthroat the cock like the whore he is. He started gagging and I was pleased to see he was learning to suck with skill. Then I instructed him to leave his panty hose on but to put his thong to the side so the BBC could fuck him hard in his little white ass. He is doing so good. I watched him moan in a feminine tine. And he squirted a little when the BBC pulled out. Then I told him to let the BBC cum inside his mouth.

 

Charlie gets Fucked in her Man Pussy

Sissy PantiesI love being a sissy trainer. I love picking out panties for my little sissies to wear. Today Charlie came over for some sissy training. I put her in a pretty pair of pink nylon panties with a hole where her man pussy is. After she had changed into them I had her get down on all fours with her ass high in the air. The hole gave perfect access to her man pussy and I had every intention of using that sweet hole to my delight today. I lubed her all up and then inserted the biggest blackest dildo I could find. I rammed it into her sweet hole and pounded that pussy. She whimpered at first but then I could see a tiny wet spot forming where her clitty was. I wasn’t finished with her just yet though. I opened the door and in walked a tall handsome built black man. Charlie gasp as he came over to her and stuck his fingers in her pussy. I could see her raising her hips higher trying to get his fingers in deeper. My little Charlie is such a cock whore. I told Charlie that if she wanted some of that BBC she would need to please me first. I sat in front of her and that little sissy started lapping at my pussy, licking my clit so deep and so fast that I exploded on her little face. Since I was pleased, I told her that I was going to reward her with some BBC. She knelt on all fours and pushed her chest to the ground and looked back with a smile as she spread her pussy cheeks and he took his BBC and rammed it deep in her man pussy. He fucked her so hard and so fast. Sissy Charlie loved it and backed her pussy against his cock until he unloaded inside her manhole.