Category: Online sissy training

Punishments

forced sissy trainingI love being a sexy ass dominatrix. I have a naughty little cunt here who needs to realize who is in fucking charge. I grab his hair and pull him down into the floor, slapping him in the face and making him kiss my fucking feet. I smack his bare ass and tell him to get up and put on that silky pink thong right fucking now. He does as he is told like the good little bitch he is and then I see him start rubbing his little clit through those panties. I grab his hair and bend him over the fucking bed and tell him he is only allowed to fucking touch his clit if I say he is. I grab his little balls and squeeze hard enough for him to apologize and tell me he wont do it again. I take my big black strap on and shove it into his asshole hard so that he screams in pain and pleasure. I fuck him like the dirty little slut he fucking is telling him that he is a sissy and no woman will ever want that tiny little cock. I laugh as I fuck him as hard as I can and tell him that he is my little fuck doll that only I can use. He cums in those tiny little panties and I make him lick them clean.

Mother and Daughter Sissy Training

sissy trainingMy daughter loves sissy training too. She is 18 now and can legally join me. She has been joining me for about a year now anyway. I have plenty of sissy boys who love the idea of a mother daughter training session. Last night was the first time my baby girl could accompany me to the dirty bookstore with a client. My sissy Sally is a 55-year-old closested sissy. My daughter has pegged him with me. She has even dressed him up to look like a bimbo Barbie. She is very talented with hair and make-up. She is in cosmetology school. She does nails too. My daughter and I escorted Sissy Sally into the adult bookstore and into the back room where the glory holes are. She was going to practice her cock sucking skills on the real thing this time. She was ready for the real thing. Online sissy training involves dildos and garden veggies, but when you see me in real-time, you get to suck the real thing. Sissy Sally was so excited. We went into the room, knocked on the wall and cocks popped through the holes. Big cocks too. Many were black or brown, but there were a few average white dicks in attendance too. I encouraged my sissy to start slow. She started with the white dicks before she finished with the big black cocks. I knocked again on the wall to signal a few studs over to fuck Sally’s puckered back door pussy. The only thing to enter her tight hole has been my strapon. She was ready to graduate sissy school with the real thing in her sissy hole. I pulled her fluffer panties down and lubed up her hole. My daughter guided a big black dick in her technically virgin hole. The best sissy trainer always makes sure her sissies get the real thing after some practice. My daughter and I had so much fun seeing our tutelage played out in the real world.

Don’t fucking make me hurt you!

Sissy trainingYeah, you fucking sissy you like the way I bend you over and spread you ass cheeks wide open, don’t you? I am, after all, the Best sissy trainer, and you my sissy boy are now in training!  I take my face and shove it between your cherry red cheeks. Before slapping you hard again. I force my fingers, dry ,in your tight hole before I shove them deeper, fucking you hard and prepping my sissy hole to be destroyed. I love the way your ass opens for me. Good boy you know you want mistress to punish your boy pussy, don’t you? I spit on your ass letting drip down your balls before standing and forcing my strap on deep inside your ass. You’re my whore and I’m going to use you for my pleasure! You groan with the force that I pound your ass, and I grip your throat. And yank your head back. “Shut the fuck up and take this dick! You are nothing but my little fuck toy, and I am going to toy with you all night, so get ready!” I hiss while pounding you harder. Your cock is rock-hard, and I reach around stroking it slowly teasing you as I fuck my ass, hard and fast. Yeah, that’s right that’s my ass and I’m going to stretch and rip your faggot hole open!  You fucking better not cum! You know you have rules, and 100% chastity is a nonnegotiable one! Don’t fucking make me hurt you! You know how much I love that! “Now come make me happy! I say as I walk away and grab my whip from off the table. You crawl over to me before dropping your head waiting for my instructions. “Good boy!” I say as I remove my strap. The hissing of the whip as it smacks your ass makes my pussy wet.  “Now eat me like the filthy little dog that you are!”  Good sissy pet!

BBC Sissy Trainer Mistress Addilyn

I’m Mistress Addilyn and I am the one to come to for BBC. A BBC Sissy Trainer by default and a very firm Mistress for sissy boys that crave dick. My style of training will rarely be sensual or kind. I am a strict control freak and a total size queen. I like my sissy sluts and Sissy slaves to also be interested in the bigger is better mantra of cock worshiping.

Be a good slut when you call me and have at least one Big black cock dildo to work with. I will hope it’s a suction cup type so that we can train you in so many ways. Having you on your knees sucking a big black cock is a great start. I would appreciate you even more if you had a full length mirror to attach that black dildo to and watch yourself suck. The mirror is important also to admire your new girly look and to see how that pussy gets gaped when you start backing up on that big black dick.

BBC Sissy Trainer

Sissy you don’t need your Wife

Sissy Panties sky

You came here because you know you want cock in your ass and you don’t know how to tell your wife. I got you to wear my favorite pair of sissy panties, and that beautiful set of pink fishnet stockings, along with that creamy lavender cocktail dress. Oh my sissy girl you came in worried that your wife found our photos of you in my favorite red dress and stiletto heels puckered up feeling like my mistress-now look at you strutting proudly in front of my men ready to be dominated. You got your ass poking out, your makeup done so well just to be dripping all over your face in seconds. You’re more than ready for your training session, I force you onto your knees and you already have your mouth wide open to get face fucked. Honey you already know what needs to be done with that  BBC- now show me what a good fucktoy you were born to be!

Play Time With Tiffany

sissy phone sexSissy Tiffany loves to get all sexy for me whenever I tell her to. I put a cute little white dress with panties and a bra in the bathroom for when she comes. I love to have her go change and when she comes out I can see the bottom of her ass I fucking love it. I get down on my knees and lick tiffany’s cock through those pretty hot pink lace panties. I take her cock out and start to lick and suck every inch getting it all nice and wet not forgetting about those big balls. Just when her cock is wet enough I stand up and make tiffany suck on my big black 10inch thick veiny cock making it sopping wet before I make tiffany bend over and spread those pretty little ass cheeks revealing her tight little puckered asshole. I slowly spread tiffany’s asshole with my black cock making her moan but I stop halfway in. Tiffany stands up with my cock still in her little round fucking asshole while I bend down in front of her and let her fuck me. Tiffany loves to fuck me hard and fast, pounding into my tight fucking pussy until he cums deep inside of me. I go behind tiffany and slowly take my cock out making sure he feels every single inch. I can’t wait for our next playtime tiffany.

Phone dominatrix

Best sissy trainer

What better way to teach a sissy slut to be on her best behavior? I brought that tramp to my boyfriend’s basketball game and had her in the men’s locker room showing us what she’s worth. They milked their chocolate cocks all over her naked body.

They whipped her with their long anaconda dicks. That whore had dick prints all over her cheeks that includes her slore face! They had her pussy gaping! They opened her up wide and took turns busting loads of hot creamy black cock juice inside her ass.

When they were through I spoon fed her all of that thick cum straight from her asshole. She is one freaky nasty slut even after the basketball team was through with her she was still yearning for more.

I guess a ho will be a ho and there’s really no changing that. Who thought a hardcore gangbang wouldn’t have been enough to fulfill her whore needs.

Online Sissy Training for Pride Month

online sissy trainingJune is Pride month. Cum out of the closet with online sissy training. No shame in being a sissy.  I love sissies. I train all kinds of men too. Men you would never guess had a closeted sissy life. Older men, younger men. Black men, white men. You might be surprised how many sissies are out there. My guess is that you know men just like you, but you do not realize it. I do not share your dirty little secret with anything, but I still feel you should not feel bad for whatever your sissy self wants from wearing panties to sucking cock. Not all men can be alpha males. This world would not function if everyone wore the pants. Some of you need to wear the panties, the sissy panties. I had a new client this week. I rarely take on new clients in my real life, but its June and I told myself I would help as many sissies come out of the closest as I could. Tyler is a 28-year-old single sissy. He is self-employed and really has no reason why he cannot be out. This world seems hostile to men who are not macho white guys with big guns and big wallets, but it is far more expecting than it once was. I worked with Tyler all week. Daily sessions. I told him screw his family if they could not handle the fact that their son likes to service cock and dress up in women’s lingerie. He owns his own home. He has zero debt. He does charitable work. Sissies are not bad people. I took him to the glory hole every day and got him a taste of all kinds of cocks. He is a different sissy now. Confident and cock addicted. He told his parents last night and he said they accepted me. Tyler had a happy ending coming out of the closet with me as his best sissy trainer. I know not everyone can come out of the closet, but you should at least come out to yourself. There is no shame in being a sissy.

Sissy Whore Treat

Best sissy trainer

I made my sissy little faggot dress up for me today in her prettiest lingerie! Her favorite is a lacy pink teddy. It’s like a body suit and she feels sexy in it! I am rewarding her with a dump load of cum straight out of my pussy as she is all dressed up for me. I spread my legs wide after she watches this think big black cock rail the shit out of me, and let her jerk off on her clitty to it. She listed to my moans and licked up any remaining mess. She stuck out her tongue and pushed her face in between my thighs and pressed her cute little tongue into my pussy hole! She sucked and licked all around and made sure to get as much cum as she could from my wet cunt!

Small Dick is a Deal Breaker

sissy humiliation training

It really is a shame that you have such a small cock. You’re not half bad looking but that lil dick is a deal breaker.  What superior sexy woman do you know that’ll settle for a tiny little cock like that? You’re so fucking pathetic the only way that I would even consider speaking to you is if you paid me for it. And honestly, the conversation better be short because I don’t like to waste too much of my time on lil dick pansies. My clit is bigger than that teeny tater tot in your panties and your nuts look like two sad ass seedless grapes. LOL. Let’s just get that embarrassment of a dick locked away in Chastity so you can concentrate on worshiping my ass and twat. I don’t need your little cunt to start squirting while I grind my ass crack up and down your face. Nose dive in my perfect booty while you tongue fuck my pussy hole. I’m gonna make your ass work since you can’t make me cum any other way! When mistress begins to squirt, I’ll squat over your baby dick in a cage and let my wetness soak you. Once I’m done using you as my slutty toilet paper and cleaning my pissy cunt with your mouth,  you can use that juice to finish yourself off. You better make sure you eat up every last bit of cum after you’re done. You know I don’t like a mess!