Tag: sissy maid training

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!!!

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.

cock sucking mommy

Mommy’s Boy Becomes A Real Sissy

Sissy training phone sexI told you the next time I caught you in Mommy’s panties there were going to be consequences. Knowing you could not resist doing it, no matter how many times mommy told you, I planned for such an occasion. I o into my room and get the new outfit I have bought for you. When I present you with your pretty pink dress, blonde curly wig, white stockings, and ruffly panties, you complain. You say you don’t want to dress as a sissy, you only want mommy’s panties. I tell you there will be no more half assed crossdressing. Since you want to wear panties so much. you will wear the complete outfit. Hearing the sternness in Mommy;s voice, you begin to comply. You put on the ruffly panties quickly, loving the way the satin and lace feels as it glides over your cock. More hesitantly, you put on the dress and wig. Not knowing how, Mommy helps you get into the stockings. The feeling of the silky stockings is overwhelming as it slides up your skin and I see your erection begin to grow. Mommy knew you would love this. A cute pair of Mary Jane shoes complete your outfit. You say you feel ridiculous, but your rock hard cock tells another story. Now its time for Mommy’s little sissy boy to service Mommy. My pussy is dripping wet and ready for your tongue. Oh, you thought you would fuck me? No, sissy’s don’t get to fuck Mommy. Sissy’s serve Mommy and Mommy’s friends with their tongues. You will get me prepared and watch Mommy fuck a really big cock. After I am finished I will need you to clean my pussy for me. That’s right, you will suck all the cum from Mommy’s pussy. I know you love the taste of male cum just as much as you love putting on these sissy clothes. If you are a really good boy, I may even let you suck my pussy juice off my friend’s cock. You always did want to suck a great big cock, didn’t you?

Forced into sissy maid training

sissy maid training

I caught you again, you little asshole. Stealing my panties so you can jerk off in them. You wanna be a girl so bad. I’ll make you one. I toss a pair of panties at you as you whimper, your hard dick softening. “You’re not going to need that hard-on. Mommy has big plans for you.” I grin. “Now put this on.” I hand you a frilly dress with pink ruffles. “No, Mom, please.” you beg. “No sir, mister. I told you that my bedroom was off limits and you disobeyed me for the last time. It’s time for your punishment.” I giggle as you don the sissy dress, your long skinny legs all hairy. I march you to the bathroom and shave them, along with your balls. You are crying now. “Better quit that bawling. It’ll smear your mascara.” I sit you down at my vanity and apply some garish make-up. Foundation, bright pink blusher, and blue eye shadow. I fluff your hair and spray it stiff with hairspray. You look like a drag queen.

“Follow me.” I order. I take you out to the front porch and point at a chair. “Sit.” I hand you a large sign written in bright colors. “I steal Mommy’s panties so she made me into a girl.” Just then several teens walk by, including your crush. They point at you and laugh as they take pics. “I just made you famous, sweetie. Bet you won’t be stealing anymore of my things.” I’m still laughing as I walk inside, leaving you on the porch to face your shame.

sissy boy phone sex

Sissy needs some Mommy Love

jack off with mommy

Oh, Michael, you poor sissy. Someone really needs to teach you how to dress properly. That frock you’re wearing looks like you stole it from your granny’s closet. It’s so frumpy and pathetic, kinda like you. I train sissy boys and it looks like you need some lessons. If you’re gonna be a sissy, be frilly or be sexy. Flaunt that shit. But those awful dresses have to go. I see that I need to take you by the hand and give you some guidance.

Taking you shopping was fun but your sense of fashion sucks. I was helping you out of a tight dress when I saw your penis. OMG. I had to laugh. It was the tiniest little thing I’ve ever seen. How can you pee out of a button? I really get it now. You’re not a sissy because you want to be. You’re a sissy because you have no other choice. There’s no way you can ever please a woman with that nub. It would be like jerking off my clit. Please keep it tucked in your panties where no one has to look at it, much less touch it. At least in your fluffy penis pouch, it looks like you have more cock.

sissy maid training

I was feeling so mean after we finished shopping that I made Michael be my pay piggy and buy me steak and lobster for lunch, while she received a cold tuna sandwich and lukewarm tea.  Such a pathetic loser should have to pay for everything. Finally, I ordered him to put on his new princess outfit and handed him a sign to carry.

PLEASE TEASE ME ! GIGGLE AT ME ! LAUGH AT ME ! OUT ME, HUMILIATE ME & PUNISH ME AS I DESERVE !

And I laughed and laughed as people stared and pointed at the pansy fairy faggot…..

sissy training phone sex

 

 

Sissy Boy Mommy Belives in Public Shaming

sissy boy mommyAs a sissy boy mommy, you would be surprised at the number of sissy fairy fags that call and email me. Not all my brats are created equally. Most of my boys are men, but I have one son who just never manned up, so I made him my sissy maid. Subsequently, this gave me hands on experience with sissy training and humiliation. But as a mommy of a sissy boy, nothing could prepare me for the company mascot. That is correct. We have a company mascot and she does not wear some silly animal costume and sing cheerleader type songs. She is a fairy princess in a pink frilly dress, often poopy panties , who oinks like a pig and acts like a total flaming sissy fairy fag. She deserves public ridicule and perpetual teasing & sissy shame.

So, I decided to take some time and shame this poopy pansy properly. Some may say she is a man pretending to be a sissy fairy fag because she is humiliation pig. I say she is a sissy fairy fag pretending to be a man Monday through Friday 9-5 because she has accepted her role as a submissive sissy slave to Goddess Levi and all her sexy phone sex sluts. She attempts to act like a man at her job simply to make the kind of money necessary support a company of hot bitches. The act is not on the phone with us, but at work among the real men.

sissy training phone sexSissies like my son and like the company mascot serve very important functions to dominant women like myself. They are our maids, fetching us whatever we want whenever we want it. They clean for us so we can save our energy for fucking the real men. They pay us tributes for being exposed to their silly asses and because they recognize our superiority. But, mostly they give us hours of laughter oinking like pigs and jumping through whatever hoop we put in front of them. Like this pathetic, shameful, ruffle panty wearing sissy, you don’t have to act on the phone with me. I know you are a real sissy in need of public sissy shaming and ridicule.