Category: Sissy phone sex

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

Walking My Sissy Bitch

I took my sissy for a walk today. I put on her sissy collar and only sissy panties. I made sure to shove my favorite plug in her little man pussy. I made it clear my sissy slut had to crawl on all fours like a dog bitch she is, while at the park i made her sniff people’s asses just like bitches do. I even made her eat treats out of their hands before I was going to show off how good her mouth is. I pulled my dildo out my bag and my sissy slut opened her mouth wide open. I shoved it down her slutty mouth so everyone could see how far down her throat she could take it. She was putting on a good show, but it wasn’t enough for me. I pulled her panties down and pulled the butt plug out of his man pussy.

Sissy panties

I shoved the plug in her mouth and then took my dildo and started fucking her opened sissy cunt for everyone to see. Her clitty started leaking and I scooped anything with my fingers and made her lick it. I didn’t stop shoving my dildo in and out of her sissy cunt until she made a cummy mess. Just like any other messes my sissy whore cleaned up with her tongue. 

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!

New Sissy!

femboy trainingI love all of my little sissy’s and I love all of our sessions! Sissy Bri is new and is learning how to be a sissy and it’s a good thing she found me because she needs help. But no worries because that’s what I’m here for. She seems to not be sure who she like and of course I told her the only whore she is allowed to be infatuated with is me. We just started our sessions and she is already thinking like a little sissy slut! She is wearing panties and a bra like a good little slut and we are working on makeup and more sluttier clothes. I just know that she is going to be such a little slut for me because she can’t stop asking when her next cock will be. Of course she was punished for that because who is she to demand a cock for herself when she hasn’t even sucked a real cock before. We started her assignments for oral just last week on dildos because I didn’t want to overwhelm her but if she wants to demand more we’ll just have to teach her what it feels like to not be prepared for something.

Sissy Loves Humiliation

humiliation phone sex

I caught you playing with that tiny little wiener when you thought nobody was looking. Look how fucking pathetic that 2-inch cock is! Giggles. Frankly, looks like a pinky in your panties. You know mistress needs a big, long, veiny black cock to fill her up and that puny shit just won’t do! When I look at your phone, I see a photo of me. OMG. You were rubbing your clitty to my sex photos. You little dick loser! I slap your face and force you on your hands and knees like the sissy bitch that you are. I take my perfectly pedicured toes and pinch your sausage with my them as I squash those little grapes you’re smuggling in your panties. The more pressure I put on your little cock the more bitch cream oozes out of it. You can’t get enough of this humiliating phone sex, can you? You need a mistress to remind you of how much of a little sissy slut you are! Your little whimpers are music to my ears!