Tag: sissy training phone sex

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!

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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.

My Diaper Baby

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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

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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!!!

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.

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?

Make me cum for Mother’s Day

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It’s Mother’s Day and I can’t believe the party my boys threw for me. All of my little sissies did the hottest lingerie show for me. I have way too many pairs of panties myself so I let them raid the panty drawer.  Let me know if you want to buy some for yourself. Then you can really jack off with mommy as you wear your special sissy panties that I hand pick for you. Feel how your cock swells when  you put them on. That’s because you really are a girl at heart. A girl with a penis is a great thing. Let me show you what I mean. I want to see you bent over with your panties down as mom guides a hard dick into that boy pussy. I’ll teach you how to fuck and suck so you can be the hottest sissy around. Mommy will break you in right for Mother’s Day. Bring that ass toy with you. You’re gonna need it.

Phone Sex Mommy Nicolette is a Sissy Mom Too

phone sex mommyI want to be your phone sex mommy! You can be any age you want too! As a P mommy, I have played with sons of all ages.  And I have sons of all kinds. Currently, I have a school boy who thinks he is a school girl! Naughty little boy who likes to wear mommy’s panties.  He had an accident at school yesterday that tore his jeans during recess. The whole school saw that he was in women’s panties and laughed at him. They called him a sissy. He ended up in the principal’s office. I had to go bail him out of jail. I have told him time and time again, he can wear my panties at home, but never at school. School age boys and girls can be very cruel. The principal suggested I get him counseling. Like the principal never stole a pair of his mother’s underwear before. Every guy goes it. Doesn’t mean they are gay or even a sissy. Some boys  just like to feel close to mommy’s pussy. Some like the feel of the silk on their little dicks. Some realize they have little dicks that get lost in boxers so prefer the tight fit of mommy’s panties on their junk. I asked my son when we got home, why he disobeys me by wearing my panties to school? He told me he thought he might be a sissy. I asked him how he even knew about such things at his age, and his response was from you on the phone! He has been listening to me be a sissy mom for all my phone sissies. Luckily, my boy toy husband is very open minded. When I told him that his son thinks he is a sissy, he didn’t shame him or even punish him. He just pulled out his cock and ordered his sissy son to suck daddy’s big dick. Sissy school is in session at my house!

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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