Category: Sissy training phone sex

Mommy and daughter fun cum time

Jack Off With Mommy RoxanneMommy loves it when she gets to eat her younglings pussy hole. I have found that I have a taste for that innocently sweet juice and the cream it gives after licking it for a while. Its like eating strawberries and cream. I like it even better because it came from me and it adds a naughty factor t amp up the intoxicating affects of arousal. The lil pussy lip so sweet and petite make my pussy wet with desire and delight. I want to pop that cherry and deflower that little hole with my tongue and my fingers until a little bit of dew drains out, then I want to lick it up and show that mouth where to make mommy feel just as good. I will direct exactly where to lick mommies cunt so that the favor can be returned. That whole hand can fit in my pussy and that wee tongue can lick mommies clit until mommy cums too.

This Sissy Mom Loves Our Site Sissy and All Sissies

sissy momAs a sissy mom, I attract all sorts of losers, but I have yet to attract a sissy as pathetic as our company Sissy. Our company mascot is a Sissy, owned by our boss, Mistress Levi. On occasion, we are invited to help shame the most pathetic pansy of them all, Sissy Michael. This sissy is such a fruity fag too. She has clothes especially made for to wear in public because she loves being shamed by total strangers, especially young girls. I was showing my daughters pictures of the site Sissy in her various outfits and they could not contain their laughter. Seeing Sissy in a cheerleading outfit was enough to make them share the pictures on their social media accounts. My eldest teen daughter captioned a picture “Sissy maid training in session.”  She was begging for me to get the company sissy to come over and be her personal servant.

sissy maid trainingI had to break her heart that it doesn’t quite work that way, but I promised I would find her a local sissy for her very own. But, I did have to explain to her that there will never be a sissy quite like our company sissy. Our site sissy has a teenie weenie that is often under lock and key by Mistress Levi. Sissies should only touch themselves when granted permission, but some sissies like this Sissy are just too shameful to be allowed to play with their minuscule little dicks. Our sissy even has her own site. I showed my daughters her site as well as blogs other women hear have done over the years about her. This pathetic cross dressing pansy has dressed in baby garb, frilly dresses, cheerleading outfits, formal gowns and even a play boy bunny outfit. She is a total disgrace to the gender she was born.

sissy boy mommyOur site sissy poops her panties; prances about in public begging to be shamed and loves to be humiliated by sexy women and total strangers. This sissy boy mommy is grateful that she does because she gives me a lot of entertainment.

Wittle sissy baby needs to be humiliated!

sissy boy mommyThe boss lady here has her very own sissy mascot and from time to time we all humiliate her. I haven’t done so before now because I try not to ever be too mean, but once I saw her baby pictures I just couldn’t help myself! Hahaha this little sissy baby is really a ridiculous sight! She sucks her thumb and wears little frilly pink baby clothes… she even wears a diaper so that she can fill it with her poop and sit in her shame all day! Is it really any wonder that we all laugh at her?

sissy momI mean just look at her! She is a hoopy earring wearing, panty pooping little sissy bitch! What could be more laughable than that? The funniest part of all this though is the fact that this sissy fairy faggot right here pretends to be a man at work every single day! Can you believe that anyone would believe that a little prissy sissy baby like this could possibly be a man? She’s even married! Hahaha The thought of a baby like this being someones husband really cracks me up! This is a sissy that needs to be dressed up and paraded about town in her poopy shame! She needs to be forced to wear a diaper in public so that everyone can see and smell her shame!

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Sissy maid training with Peggy and Nicolette

sissy maid trainingNicolette and I both know that some boys just need sissy maid training… even when they say they don’t. My daughter’s husband is that kind of boy, he is very effeminate in the way he moves and the way he speaks and he acts certainly doesn’t ever act like a grown man. Honestly, I think the only reason my daughter married him in the first place is because she walks all over him, she has no respect for him at all. It was so easy to convince her to let us play with him, all she asked is that we record it all so that she could watch it later and laugh at him.

Nicolette and I ambushed him at home, we told him that he was going to learn how to be our little sissy bitch and he didn’t even protest! He just followed us into my daughter’s closet and let us dress him up like he was our little dolly. Poor boy cried when he saw us taking pictures of his shame but his little clitty was rock hard so his pitiful whining wasn’t very effective in making us want to stop… if anything it made us want to humiliate him more!

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We made him get down on his hands and knees and pulled his panties down so Nicolette could whip his pathetic ass while I put on my biggest strap on cock, he was no longer pretending that he didn’t like it… in fact he was begging for more! His ass was red and raw from his spanking and his tiny dickie was hard and oozing precum everywhere and when I shoved that strap on dick balls deep inside him he instantly came! Pathetic little bitch can’t pretend to be a man anymore, we own his little sissy ass now!

Halloween Humiliation

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I had a blast this Halloween! My son has been awful this last month. His attitude is shit and he keeps back talking me. He is acting like he is the man in the house when really he is mommies little bitch. I was tired of his smart mouth by the time we were getting ready for trick-r-treating. I got him the ninja costume he wanted and picked out. Now he hates it. I was done with my little bratty baby, that’s when my brilliant idea hit me. I stripped him down and put a cloth diaper on his ass and lets not forget the rubber panties! I put him in a onesie and slapped a bottle lased with laxative in his mouth. If he was going to be a big baby then that is what he was going to dress up as and be dragged around the neighborhood like the giant man baby he is! As soon as we got to the first house the laxative kicked in! He shit himself just as the door opened. A big waft of shit smell and they slammed the door in his face. My brat was humiliated by the end of the night. Watching him walk around all night in a shitty diaper and see doors slammed in his face made my pussy so fucking wet. I made him lick my creamy pussy through my dirty sinky panties! That’s the best treat he got all night long.

Sweet Teen Cunny

mom phone sexAs if spending time with the neighborhood boys wasn’t enough, I was able to snag some of their little girlfriends too this weekend. Their tight little bodies, super soft skin and long hair is so sexy to me and was a nice change. Believe it or not, they were even more eager than the boys. It seemed as though pleasing me was their ultimate goal. They were so easy to teach, and took the lessons well, learning quickly how to lick my pussy and get me off. What good little girlfriends they will be, and wives someday, skilled in how to please both a man and a woman. They certainly are good at getting me off. Today was fun after a sleepover last night. Little Tracy woke me up wanting more and laid down between my legs and licked me awake. I was really getting into it when her little friend Jennifer came in and joined us. It was a licking, sucking fest and we woke everyone up with our moans of ecstasy. A glorious gang bang ensued, and I couldn’t get enough of watching over all of my little ones getting each other off so well.

After school detention for you.

Jack off with MommyYou caught my eye the minute you walked into my classroom. Way bigger and taller than the other students, I knew you were special. I checked out your tight jeans and round little ass, then grabbed a quick peek at your package. I just knew that you were packing the meat. You seemed to know exactly what I was thinking. You grinned at me, looking at my big firm tits and short skirt.

“Please turn in your homework before you leave.” I told the class. You were the last one to leave and you hadn’t even brought a book to my class. “After school detention for you, buddy. Starts in 10  minutes.” You licked your lips as you left, leaving me with a wet pussy and breathing a bit heavy.

You walked into the classroom and shut the door behind you. “Detention is cancelled today. Everyone is gone.” You walked over and kissed me, unzipping your fly.  “Suck my cock, teacher, and you’ll get your missing assignments.” I dropped to my knees and took your young, rock hard monster into my mouth. Your hand went into my hair as you face fucked me.

I stood up and took you by the hand. “Fuck me. Right here on my desk.” I ordered, spreading my legs. I almost screamed with pleasure as your 10 inch cock pushed into my juicy cunt. You jackhammered me hard. “Do I get an A, teacher?” you moaned. “Oh, yes. Fuck my Asshole. That’s your A.”

We spent the whole afternoon fucking and sucking. You came so many times. That’s why I love the young dick. “Detention again tomorrow, young man” I tried to be stern as you left. “Absolutely, but find a cute student to play with us.”  I nodded with anticipation, thinking about which student I wanted to lick my pussy.

Sissy learns the sexual ballet

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Every good sissy needs to know how to dance. Dancing and fucking are arts that a girly boy must be exceptional at. The first form of dancing is my sexual ballet. Learning the flexible poses and spins while dressed in a lacy pink tutu is a great way to become a sissy. The ability to do those contortionist bends will make for some unique fucking positions. Can you imagine doing a Balançoire while being fucked from behind? Or how about a sexy Cambré, bent over at the waist, ready to receive what your pussy craves the most? As a sissy Danseur, you wouldn’t be wearing just the leotard but also the frilly tutu that makes you the star of the show. Standing Demi-pointe, you will stick that sweet ass up and out, balancing on the balls of your feet, waiting for that first hard thrust. Bent completely over in a Fish dive position, you will beg for that cum.  To finish your lover off, you will perform a Grand plié as he fills up your boy-pussy with cum. Never before has the ballet been so sexy. The cum runs down your leotard where your lover has torn a hole so he can stuff his cock into your tight starfish as you perform your pas de deux.

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Next lesson: Salsa dancing with a sexy Latino who loves that sissy pussy.

My Diaper Baby

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I love my son as much as my girls; I know he is going to be a diaper baby forever! Even when he becomes a big adult, he’ll always be my little diaper baby! Even when I change his diapers now it makes me think about all the men I talk to that are still obsessed with diapers. They have as many mommy issues as you would think! They need a naughty mommy that is going to touch that tiny little cock when they’re getting changed. Just like every diaper change now I am sure to inspect that cock until I get that little boner throbbing. I want to feel it twitching a growing in my hands. I will stroke it, kiss it, and suck it till it’s slimy with precum. That’s just what I want… and he clearly wants too because he never cries. It will be like this forever, a bonding time that only a mother and son can share together. I made that cock, and I am going to wipe it clean, with a wipe and then my mouth… and then it will time to powder it all even that little bottom and on goes that diaper! Perfecto, my darling. This is how a date is supposed to go! A Mother/Son date that is…

Sissy Training Milf

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When you are training to be my sissy there is one main rule you must remember. I am your Alpha. Yes, I am a female, so? You call yourself a man to your colleagues but when you step into my room you’re my slave. When I get my hot black slit fucked my sissy boy better be there ready to beg to suck the cum out of my twat and clean it all up. Before you can you must also thank the man who filled me up for allowing you to taste his yummy load. You’re lucky I let you get this close to my beautiful pussy because your little dick can’t even begin to satisfy me. Even during the nastiest times you will be around to be my sissy will be in training! I refuse to rough up my delicate ass after taking a shit when I can just have my bitch clean my shit and piss with his face. Being a sissy in training has its perks though! You get to spend all the time I want you to with me!