Category: Sissy training

Sissy Training Men I Enjoy, But I Love Cuckolding Men Too

sissy trainingSissy training may be my specialty, but I cater to other fetishes too. Cucking men remains a close second to feminizing men. I love my cuckold callers. They call me because they know I will cuck them with big black cocks. And most men want to experience a big black dick in their sissy holes. I get it. Black cock will always be superior cock.

Little Michael comes over once a week so I can cuckold his pathetic ass. His little dick could not satisfy a Barbie Doll. Although he might not possess the smallest dick I have ever seen, he remains a close second with a three-inch nub. Plus, he cums quickly too. So, when he comes over for a cuckold session, I know to lock his little clitty up in a cage. As his BBC sissy trainer, I do not want him cumming unless I give him permission. And I rarely give losers the right to rub one out.

I Enjoy Cuckolding Men with Big Black Cocks

While locked up, Michael had to watch a real man fuck me. I deserve the biggest cocks I can find. But little dick men, never deserve a hot woman like me. I reserve my fuck holes for only the best cock meat around. As I took 13-inches in my cunt, my little sissy cuckold watched in awe and jealously as I fucked a beautiful and superior black man. My hung lover insulted my caged-up sissy too. And he deserved the small dick humiliation.

But my sissy could not masturbate. He just had to sit their caged like a wild animal watching a real man make me cum. Once my black stud filled up my pussy, I let my little cuckold clean up my creampie. And I knew my pussy contained lots of cum. Black men cum more than loser white boys too. My cucky licked up a gallon of cum from my cunt. And I think he got every drop too. I even let him suck my cunt juice off my stud’s big black cock.

Michael spit shined that big black dick too. Polished his knob, washing away all traces of my cunt. My black lover went back to his wife. And I sent my cucky home in a pair of my sissy panties and a belly full of black cock spunk.

Mistress phone sex slut Remi

mistress phone sex

Mistress phone sex trainer slut Remi wants to train you to be the perfect panty boy, sissy bitch! You’re going to learn to suck dick, ride dick and drain a man’s balls into your slutty mouth and cunnie! I have guys on the way over tonight and I need a cum eating cuck to play with when they get here. You need to be turned out, like the cum dumpster you are. You’re not a real man anyway. One look at that little bitty clittie of yours tells me that you belong on your knees with your pretty bitch lips wrapped snugly around a thick, pulsing fuck rod. I may as well turn you into a girly, panty wearing he-slut while I’m teaching you to swallow big, gooey loads of cum. I have a little corset top and thong that are going to look so perfect on you. I’m going to make sure you look sexy for the studs that are coming over to fuck your face and ruin your tight little he-cunt. You’ll have to sit there in your panties and rub your clittie while I’m getting my hot, whore cunt filled up. I’ll let them have you but only after you eat up all the mess they made fucking me! I just made one of my little bitches rub his pussy and watch while I was double stuffed with thick, chocolate cocks. After they fucked me, I made that sissy slut suck my shit and cunt juices from those giant bbcs while I teased his fuck hole with my strap on. I popped the head into his tight, little pussy hole and told the stud that was fucking his whore throat to ram him back onto that cock! We pounded that bitch back and forth until my fuck stud couldn’t cum anymore and that bitch’s slut hole couldn’t take another drop! I hope you’re ready to be my next panty wearing, cum guzzler because I’m ready to have my fun with another sissy bitch.

Femboy training for old sissy slut

When I am doing some Femboy training on an old sissy is so fun. “Wear these panties” I instruct you to do. After you are fully dressed, I show you what you will get. “Look at your new paddle” I say as I show you the sissy paddle I got. “Plus, a new dildo attachment ” I tease while putting it on. Right away you get in position with your ass in the air. Since you are trained right you start to thank me every time your ass gets hit with the paddle. I hit you hard over and over. By now your body was trembling and as was swollen.

Femboy training

The best part was that it left the word “sissy” stamped on your ass. Your clitty is hard and stiff and bounces with every spank. Therefore, I lube my new dildo attachment. As soon as I was lubed up you spread your legs. “You want me to fuck you, don’t you?” I ask. “Yes, mistress please fuck me hard” you whimper like a slut. But I want to reward you for taking my spankings. That’s why I just slammed my cock toy deep inside your sissy pussy.

Best thing about you getting femininized is when I fuck you hard. So, when you feel my cock inside you, you start to beg. “Please let me cum mistress, please” you beg and whimper. “Not yet slut” I respond making sure to tease you some more. That’s why I spank your ass while continuing to ram deep on your sissy cunt. “Please mistress” you moan as you start exploding all over the ground. “What a pathetic sissy whore you are, you made a mess that needs cleaning” I say as I pop my new dildo out your sissy hole. 

Being The Best Sissy Trainer Makes Me Horny

I am the best sissy trainer there is. I am just the right amount of cruel and caring. I will stomp on your balls with a high heeled shoe while smiling and telling you what a good fucking little sissy whore you are.  I want to make you dress up all slutty and sexy. In a cute little shirt dress, garters, lacey panties, and push-up bra. I will put plenty of blue eye shadow and red lipstick on your fucking slutty little lips. I will tell you what a sexy bitch you are while parading you out the door to go look for cock. Once we find some cock, I will fuck the cock first right in front of you while telling you how worthless you are and how your dick is nonexistent. I mean let’s face it if you were a real man I would not have to go looking for cock. When I am done it is your turn. I want that cock deep in your mouth and your ass. When you are full of cum like a good sissy slut I will make you eat all the cum out of my pussy.

best sissy trainer

Sissy Training to Overcome Being Manly and Embrace Femineity

Sissy training can be achieved in many ways. With me, Mistress Addilyn, my focus is on guiding you out of your shell. When it comes to your true sissy girl self shining, let me guide you into those pretty panties.

Ultimately your desire is to be the sexiest and best sissy girl you can be. As emphasized, I feel I can assist your cock sucking needs. Let me know how much of a sissy you are already. Next thing, tell me of where your at in being a sissy. Maybe watch some Jackoff porn and let that ignite your desires.

Once I get an understanding of where you are and what you desire then I can guide you further. Simply put, If it’s only that you are getting iced up, dressing in your pretties and feeling feminine and ready to play. Then of course that is also a prefect situation for calling me.

Finally, let me see your pictures of that pretty girly self of your sissiness and quite possibly I will embrace outing you to all of my readers. Obviously, every sissy girl loves to be in the spotlight.

Sissy Training

 

I Will Control Your Cock And Your Wallet

Dominating you completely makes my pussy so fucking wet.  I love controlling you completely. I want to control your cock, your whole body, and your wallet. I am going to make you my pay piggy. I love making you punish your cock and balls. I get off knowing I have enough control over you to make you cause yourself pain.

 

Every time you scream in agony my pussy throbs.  I am going to force you to get fucked up on booze or something else whenever the mood strikes me. I  will force you to dress up like the trashy little slutty cunt that you are. After you are all dressed up I will parade you around to look for cock.  My pussy tingles with excitement as I see you spit-roasted by two huge cocks.  Seeing your face and your ass covered in cum is going to make my cunt juices drip down my legs. Your little tiny dick belongs to me and I will use it and abuse it as I please.  The whole time I am abusing you in every way possible while reminding you how your dick is fucking useless,  I will be draining your wallet too. You will send me all the money and gift cards I ask for. I think you will learn it is not smart to defy your mistress. Then when I am done with you, you will lick my pussy and pleasure me. It is the least you can do to thank me for my efforts.

Mistress phone sex with your fav superior blonde!

Mistress phone sex I am the best at some dirty Mistress phone sex. All of you little sissy boys need a dominant superior woman in your life. It should be your dedication and honor in life to please a beautiful goddess like me. My little bitch boy Tate became obsessed with me once I started mesmerizing him with my sexy body. At first he was resisting his place as an inferior little sub boy; that was until he saw my big fat tits and pretty bald pussy. All he could think about was digging his head between my legs and lapping me up until I was squeaky clean. He knew that could entail him eating up a superior mans creamy load from my hot wet hole. 

Now Tate cannot get enough Phone domination sessions with me. I sent him some pictures and videos of me in the shower and he immediately went into his sub space and begged for more. I have trained him and turned him into he best little toilet boy too. As you could see, when I took those shower pics/vids I made sure to include some of me squirting out my piss everywhere. I knew he would be licking the phone as his precious little cock head began to drool pre-cum. You can be the perfect little sissy boy for me too; I just need you to lock up that cock and let yourself be pathetic!

Sissy Panties Show You Mistress Meadow Really Cares

You’d never tried sissy panties before. Your sissification started slow. It started with a lot of porn. The kinkier and dirtier the better. Just stroking your cock wasn’t enough. You needed something pushing up against your prostate to completely drain that horny cock. Even when you were inside of a cunt, you wanted something inside of your asshole. You couldn’t let anyone know about your dirty pegging fetish. You even started stroking your pegging porn in the bathroom at work, instead of at home. Too bad, as your boss, I can see all the activity happening on the company wifi.

sissy panties

Sissy Panties Make Pegging More Fun

I called you into my office at the end of the day. There was a strap-on, lube, and a pair of panties on my desk. I asked if you recognized these things. I could see your cock getting hard in your pants. You were too red in the face to answer. I started pulling off my blazer and dress and putting on the strap on. “Bend over.” All your dreams were coming true at once. All the blood was rushing to your cock while you stared at the thick strap bouncing between my legs.

You took your pants off and put the pink panties on. I bent you over my desk and rubbed the lube on the head of my dick.  I pulled your panties to the side and the plug you’d been wearing out of your asshole. Look at that. You came ready for me. Then, I rubbed some of that lube on your used asshole. My fingers slid in so easy and so did my dildo. You tried your best not to moan, but I was pounding the way you’d been dreaming of. All those pornos playing back in your head had your asshole twitching around my strap. Let me know when you’re ready to cum.

Sissy phone sex with Miss Remi

sissy phone sex

Miss Remi the sissy phone sex mistress is looking for new sissy bitch men to play with tonight. I have plenty of sissy fags but I love turning out new girly bitches! When I have a man in panties for the first time and I’m making him admit to me, how badly he wants to suck cock and get his whore cunnie reamed, I get so excited! I remember the first sissy that I turned and how fun it was dressing him up. I was at my friend’s house and her stepdad walked into the room right as her mom was showing us old pictures of him at a Halloween party. He was dressed up as a stripper and had a few dollar bills shoved in his g-string. She was telling us that she could tell how much he enjoyed being dressed up and how the bikini bottoms perfectly showed off how tiny his micro cocklett is. We couldn’t hold back our giggles when he walked by. He asked what was so funny but then turned all red when he saw the pictures we were looking at. We started teasing him and at one point, my friend’s mom went and got one of her old bikinis for him to try on for us. He tried to refuse but was outnumbered by the three of us telling him that he better put it on and model it. We were only going to make him dress up and tease him but when we saw how he looked in that string bikini, we took things a little too far. When you call me, I’ll tell you about holding on to my best friend’s step dad by the hips and pulling his bikini bottom to the side so that I could shove my 12 inch strap on deep in his slut hole! I hope you’re ready to be the next little bitch getting pounded by my big dick! 

 

Your sinful Sissy panties are a aphrodisiac for Mommy

You know me, always pushing the boundaries of your Sissy panties and never holding back. You know how much I love seeing a Sissy in a pair of lacy, frilly panties. It’s an aphrodisiac for me. And you my Sissy, do not completely disappoint. Sissy pantiesYeah, your wig looks cheap and you aren’t completely shaven but that’s ok, I can still work with that. I love those panties though. The rush of power I feel when I slide over those panties and slam my thick cock into it is truly out of this world. I mean sure, if your wife or girlfriend found out what you really are I am sure they would recoil in disgust and throw you away. But not me baby.

I just think you need a bit more, I mean a lot more, Sissy training. I’ve seen it all, cheap wigs, ill-fitting outfits, but at least they try. And that’s what counts. But when you are a true cock hungry whore like yourself, I can do anything. You know I’ll work your boy pussy so hard that thing will be gaped for days. It will make me so proud when your bussy is filled up with two hard throbbing cocks.

When they pump you full of cum, I will make my lesser little sissy clean you out slut. It’s a sight to behold and it makes me proud to see how far they’ve come. But all you sissies always need more training, and I’m more than happy to provide it with hot Taboo phone chat!