Category Archive: Sissy maid training

Sissy training phone sex with Mommy Pearl

sissy training phone sexI’m ready to start your sissy training phone sex lessons. I’ve known since you were a boy that you were special. The way your sweet ass wiggled when you walked. The way you lisped your words. That little flounce when you were pissed. But it wasn’t until my panties started disappearing that I figured out the truth. At first I thought you were just like your older brother, stealing them to jerk off into. But I snooped while you were at school and it blew my mind. In a small set of plastic drawers in the back of your closet, I found your secret stash.

It was filled with beautiful lingerie and panties. I recognized some as mine and some as your younger sister’s. I had wondered what you spent your allowance on and now I knew. There was a box of makeup and Ebay receipts. My son was a sissy. OMG!!!  I snooped a little more and found one of my old vibrators. I put it to my nose and got a faint whiff of ass. I giggled to myself, thinking of you fucking yourself, wearing your panties. I quickly put everything away.

Tonight is ours, my sissy boy. Your sister is sleeping over at her friend’s place. Your brother has another week of college. It will be just me and you tonight as I reveal what I know. Tonight we will start your transformation into the cock sucking sissy that you desperately want to be. Mommy has a big black strap-on and a wicked smile on her face. Your secret is safe with me.

Jack off with Mommy at the Yard sale

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It was a jack off with mommy annual event in our neighborhood. My annual garage sale. I’m not a hoarder so every Spring I clean out my closet and lingerie drawer and sell it all. It’s so much fun to watch my neighbors show up, trying to be all discreet. They creep over a few at a time. And no one ever tries to haggle. They know I have the good stuff. I even have a few used toys if you’ll just ask.

You were my first customer. I was watching you out of the corner of my eye as you held a pair of panties up to yourself. I stifle a giggle as you try to tell me that they were for your wife. Your wife is a 250 lb oinker so I know that these are for you. I always suspected that you were a panty boy and now I know the truth. “I think they will look great on you.” I whisper, watching you turn red. “Shhhh, it’s our secret. Just let me know when you are ready to model them for me. I love a man who wears panties. Would you like the matching bra, too?” You look like a fish outta water as you gasp for air. I know I’ll be seeing you soon.

By the end of the sale, I have a fistful of cash and a list of names signed up for sissy lessons. Wouldn’t you like some of my sexy things, too? You can model it for me and send me pics. Mommy loves little faggot boys who beat their meat into their panties. Your secret is safe so come share with me.

 

Panty Clad Sissy Boi

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Earlier I was doing a little online shopping.  I was thinking of you as I searched for the perfect outfit.  Something pretty and perfect.  A little something to bring out the color of your eyes.  I wanted it to fit your personality.  It had to let others know that you are a cocksucking sissy boi.
You know I love dressing you.  I was thinking of the way your little clitty would fit into a lacey pair of panties.  I sat back and imagined you giving your first blow job in nothing but those cute little under things.  I thought of how your little prick would tremble with anticipation.
Funny how just a bit of shopping brought you to mind.  Now all I can think about is your lace covered dick.  I want to see you lick and suck his cock until he blows his load right down your throat…. Hmmm, looks like I have more shopping to do for my sweet little cocksucker.

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.

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!

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.

Sissy Training Milf

sissy training phone sex

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!

Mommy breaks in a Sissy.

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My poor little sissy. He still hasn’t learned how to properly suck cock. I think it’s time to go out and get some practice. He says no because he doesn’t want to be recognized in public wearing his mini skirt and thigh high stockings. But he’s such a pretty girl and that sweet mouth is begging to be used along with a tight little man-pussy. Oh, yes. it’s time. I saw him last night on his knees trying to suck a big black cock. He gagged and sputtered. My nigga loved dominating him and just face fucked him harder. He nutted so hard that cum came out of sissy’s nose.

So put on your pretties, your lacy thong. Get those balls shaved smooth. Cause your training starts tonight as I guide you on being the perfect little cum guzzling tranny slut. Our first stop is a local glory hole where you can learn to suck a cock correctly. Maybe after a few dozen loads pumped down your throat, you will be able to give head with some finesse. If not, I am gonna just back you up against that padded hole and let the savages rip that asshole wide open. Oh, they are gonna love that tight little boy-cunt so much!!! And I will be laughing at you while they do it!!!

Make me your cum slut.

jack off with mommyNo matter how old I get, I will always love sucking cock. I first started as a teen with my brother and his friends. I can still taste all that cum. I was an addict at an early age. My favorite oral sex is forced sucking. Having a man grab me by the hair, rubbing his swollen dick against my lips and demanding to be let in is one of my biggest turn-ons. I pretend to fight him, making him frantic in his efforts to get it in my mouth. I tease him first, licking his balls, stroking my fingers against his asshole. I hear him moan and I’m wet. I open wide as he pushes it clear to the back of my throat. My gag reflex kicks in and then subsides as my throat opens. I feel his nuts slap against my chin. I can smell them, the sweaty odor. It makes my pussy even wetter. He’s face fucking me now, not caring if I can breathe, just thinking about spewing his load into my mouth. His cock pulsates as my own pussy winds up. Just as he erupts in a massive gush, I start to cum, too. Mmmmm, are you ready for some of this experience? Or maybe you need mommy to teach you how to suck a cock and please a man. Older women know how to make you explode.

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