Category: Sissy maid training

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

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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!

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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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.

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Mommy sucking dick with Daphne

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I know you watch Mommy sucking dick in the hallway mirror. You are supposed to be in bed. Instead you are rubbing your cock while watching mommy sucking this big black cock. You are not being a good boy and you know what Mommy does to Bad Boys. You watch Mommy dominate her her Sissy boys and make them suck big black cocks. You know that Mommy loves have a nice big thick nigger dick in her mouth just as much as she loves having it in her pussy. You also know that Mommy loves watching little sissy fags like you sucking on big cock. You are being such a bad boy, do you need a spanking from Mommy? Mommy will spank your bottom until your little ass is all red. Then Mommy will make you choke on his big black cock getting nice and wet. And he’s going to take that big cock and rub it all over your tender ass, and make you his bitch. No do you want to be a bad boy or do you want to be a good boy and do as you’re told? Mommy loves it when you’re a bad boy.

Sissy needs some Mommy Love

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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.

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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…..

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Dreams of a Sissy Training Mommy

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I had a kinky dream last night. I was training this sissy boy to be a good little cocksucker. She was so pretty and her tits were perfect. I was wearing a monster black cock strap-on and I had her bent over. Her tight little shithole was gaping from the fucking I gave it. I was loving the feel of those balls as I banged hard against them. It was like my fake cock suddenly become real and I was getting those amazing sensations in my nutsac. I reached around to grab her by the throat. I heard her whimper as I pushed 10 inches into that anal cunt. I didn’t even care, which is strange, because I am a sissy trainer who is usually patient and gentle. Dammit, I’m a mommy, not an animal.
But this whore was mine. I pulled out of her boy box to turn her around to suck em off. She whimpered as I shoved my shitty cock into her throat. I found that making her gag felt so good. That throat squeezed down hard on my fuckstick as I pushed deeper. I felt my balls tighten. She ceased to become a person to me as my cock become to pulsate in that hot mouth. I never wanted to be a man before but this was fucking fantastic. I screamed out loud as my big dick exploded all over her face.
When I awoke, I found that my belly was dripping with something sticky and white. I dipped a finger into it and smiled. I was covered in cum and it was delicious. Come share your wicked dreams with me!!!

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Mommy’s Frat Boy

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I pushed the vibrator deeper into my pussy. It felt so damn good. You’d think I’d be satiated after all of the cock I got last night but when I woke up this morning and felt his cum still oozing from my battered cunt, I got all turned on again. He is my best friend’s son. We went to college together and she made me his godmother when he was born. I never expected to be his FAIRY godmother.
I hadn’t seen him in several years while he was away at med school. He was an awkward geeky boy with crooked teeth and glasses. I never even thought about his cock even though I love it young. But when I visited Linda yesterday, I almost fell over when he came through the door. The geek was gone along with the braces and bad skin. He flashed a sexy white smile at me and hugged me. “Nice tits.” he whispered, making me laugh.
Linda had an appt and invited me to stay until she got back. He and I got busy getting to know each other again. We talked and laughed until he looked at me all serious. “I’ve always wanted to fuck you, Pearl.” He reached for me and I didn’t say no. His cock was thick. When he pushed it deep into my deprived pussy, I was a goner, a shameless begging whore. He made me cum twice before he stopped. “Let’s go back to your place.” he moaned. He ate my pussy like a starving man. I sucked his cock and licked him clear to his asshole. Then he was back inside of me, driving me wild. His pistoning hips churned my insides into butter and I was more than ready for his cream. When he finally allowed himself to cum, it was like a scream of pain and bliss.
I awoke to find him gone with a note that said, “I’ll be back tonight, Pearl. I took your panties with me. Tonight, I will show you yet another side of me that I think you’ll love.”
So, it looks like a have a brand new sissy boy on my hands. A mommy can never have too many. I can barely wait to hear his secret. Just in case, I have a big black strap-on lubed and ready for him. It’ll be my pleasure to take that ass cherry.