Tag: Sissy training

Good Sissy Bitch

Mistress phone sex Sky

Stand in front of the mirror- naked, tell yourself you’re a beautiful woman. Remind yourself of that gorgeous long hair, and cute cunt you will soon have. The panties you wear make you sexy and the heels you put on, make men jealous that only I can fuck you. Every night when you get ready for bed- you dress yourself in the lavender laced nightgown that I picked out for you. Look at the calendar reminding yourself of the date your breasts will soon be as enhanced to be as big as mine. Prepare your hot pink fishnets and 6 inch high heels for tomorrow-Don’t forget that sexy knee slit, skin tight black dress that falls right above your sexy ass. My men will need a fucktoy in the morning-and you my sissy bitch are just the perfect treat. You’re going to suck every single cock I put in front of you to get them ready before they fill my fuckholes. I’ll make sure you eat my ass too- you were made to satisfy me and any man I put in front of you.

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!

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.

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!

Stop Fucking Texting Me, Femboy!

Sissy phone

 

Do you know how many sissy phone calls and texts I get from insecure little femi-men who aren’t sure of their sissified personas?  Way too fucking many!  Be proud of the priss you’re becoming, no matter what stage of boy slut you’re currently navigating.  Confidence is key in concocting your clitty craving candy doll self.  Always remember progress is success.  If you’re trying, you’re winning.  Just stop whining about it already, you dumb cunt.

Some guys keep their sissy side a secret and just talk with me about it on my Sissy Slutline® and never let the girly girl inside of them out into the real world.  All of my sissy students are leaps and bounds ahead of them the moment they walk through my door.  They’ve made the decision to bring the boy-bitch out of their pathetically ill fitting man bodies and are willing to let me guide them on their way toward wimpdom.  I just wish they would be secure in their decision making and my guidance and go with the clitty clamps and pink lady lingerie I force them to wear.

Yes, your garter belt looks great and your pretty wig really makes that mouth of yours look oh so fuckable.  You’ll have every big black cock in town lined up at your door to get a piece of that mouth pussy.  Is that what you want to hear?  Well, it’s true.  We cleaned you up, waxed you down and bleached the hell out of your impossibly dark asshole.  You’re ready to go, Nancy Boy.  Take a dick or two up that wussy ass pussy of yours, feel the confidence you can gain from taking a couple of mandingo dicks right up your butt.  Whatever, just stop fucking calling and texting me late at night with this shit!  I see enough of your asshole as it is!

 

Help Mistress Suck BBC

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I’m going to make you watch as I take these big black cocks in my mouth! You’ve been a naughty little bitch so you were going to dress up in your sissy panties and a sexy bra for mistress. You know our big dick daddies love a bitch that’s made up too so im gonna smear some purple lipstick on you too. Now, hold these big thick meat sticks while I lick all around the mushroom tip. Don’t you wish your dick was big and veiny so mistress can wrap her slutty lips around it? That little winky in your pants could never make my mouth this wide. You better not even think about touching that wimpy little sissy Clit while you watch mistress suck down these massive loads! you’re gonna beg for big daddy dick until we feel like you’ve earned it!

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

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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!