Tag Archive: sissy training phone sex

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.

Sissy boy punishment

Sissy boy mommy

Someone has been a very naughty little boy, catching you jerking off without Mommy’s permission is very very naughty. First things first…we have to go to the store because you are out of diapers. I put you in the back seat and strap you into your car seat making sure you can’t get out. I have a cup of water in my hand and you ask for a drink. As I am handing it to you I “accidentally” spill the whole cup onto your pants crotch area and down your pant legs. “Oh my, too late to change your pants baby, we have to get going.”
We arrive at the store a moment or two later and the water on your pants hasn’t dried. I come to the back seat and undo your car seat and say let’s go into the store. You pull on my hand a yell no at me. My eyebrows go up in an “oh really” look at you. “Get out of that car right now young man, before I take you over my knee right here in this parking lot.” You start to step out and your pants…you definitely look like you’ve peed your pants. I grab your hand, walk into the store, grab a cart and make a B-line for the diapers. I grab about four of the biggest boxes they have and load them all into the cart. I grab your hand again and pull you along to the check outs. People are staring and even laughing. Think it’s at Mr. pee pants? Or that I have a cart full of diapers that you clearly need.
I put you into the back of the SUV and start to take your pants off. “What are you doing Mommy??” I give you a stern look and tell you that I am going to put your diaper on. The look on your face and the begging that came with it was quite a lesson for you. I get the diaper under you and use the baby wipes from the car and clean you off. A passerby saw your big cock being wiped down like a baby and she looked shocked. I fasten the diaper on you and tell you to get your pants on. In the car ride on the way home I ask you “Do little boys jerk off without Mommy’s permission?” A valuable lesson for my little baby boy.

Sissy training phone sex

Sissy Boy Phone Sex Mommy for you

sissy boy phone sex

Ready for some sissy boy phone sex play time, little boy? Your big, obedient mommy is here to make sure you get the proper training. I’m a no-nonsense mom who expects my boys to be able to serve any cock in town after they are trained. A rigorous schedule of feminization is followed by cocksucking lessons. Are you ready to flounce it for me, little sissy? Purse those pretty pink lips and wiggle that panty ass. That’s a good girl. Now let’s work on that pussy power.
A good sissy needs to be sweet, obedient, submissive, and able to accomodate any size size of cock. Today’s lesson is simple. Mommy is bringing out the big fuck toys and the strap-on. You are getting that first lesson in taking a cock in that new boy-pussy. Don’t worry. Mommy will be kind. It will only hurt a little. I’m not really a mean mommy. I will kiss your booboos and give you a titty. Like a real mom, I just want the best for my sissies. Don’t be afraid. Come to me and I will teach you all that you need to know. Your secrets are safe with me.

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!

sissy training phone sex

Sissy learns the sexual ballet

jack off with mommy

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.

sissy training phone sex

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

My Diaper Baby

mom fantasies

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

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.

jack off with mommy

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!!!

Mommy Phone Sex or Sissy Mom Sex?

mommy phone sexSundays are mommy phone sex days.  Mommy gets dressed up in her Sunday best. Maybe you get to see her putting on her sexy pantyhose. Or catch a glimpse of her in her sexy undergarments. Are you turned on or jealous that she gets to wear such pretty things and you can’t? A sissy mom would never punish you for wanting to play dress up in her clothes. She would actually encourage it. I have 6 sons and not all of them share the same fetishes. I have two boys that love mommy’s panties, but for vastly different reasons. One of my older sons was a panty stealer. He would take them out of my dirty hamper to jack off in them. He loved the smell of my ripe pussy, the flavor of the cotton lining. Like most teen boys, he was just curious about mommy’s pussy. Once he got to eat and fuck the real thing, he lost interest in my panties. My youngest son from my first marriage however, liked more than my panties. He liked all my sexy clothes, my shoes, even my makeup. He is a sissy boy, but I love him. I encourage dress up. Even gave him a girl’s name since clearly he is more of a daughter to me than a son. We shop together for clothes, he even fluffs some cock for me and does little sissy maid tasks. Sometimes I am a very nurturing mommy, other times I am getting off on publicly shaming my sissy boy. So if you like mommy’s panties for reasons other than mommy’s pussy, don’t feel ashamed. You just need a sissy training mommy to help you be the best sissy you can be. Who is ready for dress up time? Sissy school is now in session.

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