Category Archive: Sissy maid training

Show me those panties!!!

jack off with mommySometimes you just need to Jack off with Mommy. I’m a sissy boy mom. I love taking you wanna-be sluts and making you into cum slurping little faggots. I know you steal my panties or maybe your own mama’s, or your wife’s. They have no idea on how to deal with a sissy like you, but I do.

One call with me and I will own your little faggot hole. I’m sweet to my newbies but I won’t be so easy when it comes to breaking in that pussy. It’s your secret desire to be a girl and I plan to Ass-ist you. Here’s my orders. Shave those legs and those nasty fuzzy balls. Steal some panties or I can sell you a pair or two. Grab your butt plug, dildo, and lube. And you will also need a glass.

We’re going to have a roleplay and it’s gonna feel so real. I will tease and demean you, gently at first. Once we get that boy-pussy all nice and wet, you’re gonna fuck that pretty booty for me. Or maybe I’ll pull out my training strap-on. Then I will get rougher and call you names. You know that makes your clitty swell in those panties. When you can’t take any more, you’ll cum in that glass for mommy. Then I will give you two choices. Drink it like a good little cum slut. Or freeze it and make it into a cum-sicle for our next call. Yummy frozen cummy for my panty boy.

Come meet your new sissy mommy for that special training that I know you need.

Sissy Lessons with Mama Pearl

Sissy maid trainingSissy maid training classes are now in session, boys. Sign up now to learn to be that cum slurping little faggot that deep down you really want to be. In my special tutored classes you will meet our sissies who want to be just like you. Together we will dress up and do our make-up. You will transform from masculine guy to a sexy, flouncing girly-girl.

Lesson two will be playing with a variety of ass toys. Bring your favorites and show the class how much cock you can take. We got to get that boy-pussy stretched wide open. No man wants to fuck a cry-bebe faggot. You need to take that fuck stick to the hilt and love it.

Lesson three. We will practice on each other. Learn how to approach and flirt to get your needs met. Lots of roleplaying to get you feeling good and confident. Bring that sexy lingerie and those lace panties and learn how to rock them. High heel or stilettos required.

Lesson four is the best. I will have some sexy tranny-loving men with large cocks come in and show you how it’s done. I will fuck and suck and demonstrate on these meat sticks before I allow you to join in for your first taste of another man’s cum.

Are you ready to begin your new life as a tranny? Come join Mama Pearl for some therapy and education.

Late night Tranny fantasies

Sissy training phone sex

Just admit it. Sissy training phone sex is what you are on here looking for. You’re not just another hard dick looking to get jerked off.  You have some special needs and you want the perfect mommy to help you. Sweet boy, quit hiding from your desires and come tell Mommy. You see, I’ve known your kind before. My older brother and my own son are both sissies. I trained both of them to be cock sucking little sluts. I can train you too.

I mean, you’ve known from a young age what you really are. You are a closet faggot who hides the fact that you want to be a girl. You want to be dressed up. You want to be properly and gently trained. I want to hear those fantasies. I’m an older sissy mommy with experience so no shame, no judgment.

Your need to wear panties and lingerie doesn’t shock me. In fact, i will sell you some that are perfect for you. You also need an ass toy to start your training. Oh, it will feel so good and so right inside of you. My strap-on is also available to help you stretch that new pussy.

Quit trying to sleep when all you think about is cock. Bring it to Mommy and I will explore all of your faggot or tranny fantasies. You will be so pretty and fuckable.

Training my new sissy

jack off with mommy

Jack off with Mommy while I teach you how to be a sissy success. Mommy knows what ti takes to be more than just a dress up game. You have to become a real girl. A slut. One that can please men with your cock sucking skills and a love for cum.

“Mommy, how can I be a real girl.” you ask. “Can I wear your clothes?” Sweetie, it’s more than just wearing my clothes. Any boy can put on women’s clothes. You just look like a drag queen. You have to learn how to wear those clothes. I mean wear them like a woman. With class and a flounce.

And your cock sucking skills need work too. You look like a pig slurping at the trough. Any whore can do that. You need “the look” as well as the skills. Look at him with those big eyes, nibble a bit, leave him waiting for more. Now take that meat rod down your throat. Deeper. Oh yeah. Now gag just a little. Make him feel like a man. You’ll get that cum that you crave so much.

I can teach you this and more. Come on, little sissy. No one has to know your secret except us. Be the best sissy that you can be. Just reach out to Mommy…

 

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

Jack off with mommy

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

sissy boy phone sex

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!

sissy training phone sex

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.

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