Tag: sissy training

Sexy Mommy Rendezvous

sexy mommy darlaWhen we have our sexy mommy rendezvous we ravish each others bodies. We spend hours just touching and kissing building the flames of our desire until it is a raging inferno that can only be extinguished with unbridled passion and lust. Our time together is never short lived and it amazes me that Harley sits and watches quietly while rubbing her little clitty through her beautiful silk panties. She always dresses extra special for mommy and her friend like a good little sissy, a pair of mommy’s musky panties in one hand that she holds to her face, inhaling the scent as she watches the show. She makes mess after mess in her silk panties and never leaves her vantage point, watching wide eyed, We always let him play clean up when we are over and let him buckle the strap-ons of his choice on us so that we can fuck his tight little cunny and make him squirty squirt all over. For now he is mommy’s sweet little sissy but some day he is going to make someone a wonderful forever sissy.

Grammy’s Little Treat

grandma phone sex

I caught my grandson rummaging in my panty drawer today. I asked him what the hell he was doing and he said ” Grammy, I wanna be a girl for Halloween and you are the sexiest girl I know.” What could I say to the little bastard? I decided to help him become a sissy boy. I had always suspected that he had feminine ways.
I picked out a frilly top and mini skirt and a pair of slutty heels. We had fun trying to stuff one of my bras for him to wear. Next, I did his make-up and hair. Damned if the little fucker didn’t make one sexy whore. My evil mind wanted to pimp him out. With his tight little body and virgin ass-pussy, he was worth a fortune to my P-friends. My imagination got carried away as I imagined introducing him to his first cock, showing him the proper way to eat man-meat. I’d get on my knees and lick that little asshole until it was good and sloppy before allowing some older man to pop his butt-cherry. My fingers slid into my pussy as I pictured him being penetrated. “Oh Gram, that feels so good.” he’d moan, as a fat penis rammed him hard. I’d place him on his back, push his legs back and allow you to slide into that boy-cunt. His penis would be standing straight up and I’d reach out to stroke it while your meatstick slid back into his slippery hole. Soon you’d both be moaning as you filled up his cum dumpster and he shot his cum unto his belly.
And like a good Grammy, I’d be there to clean up the mess, lovingly lapping the jizz from both of you.
Wow, what a Halloween dream!!! I can’t wait until he gets home from trick-or-treating tonight. We’ll explore this need to be a sissy and see where it goes. My pussy is twitching just thinking about it. Care to share in the treats?

family fun phone sex

Sister Fucking with My Sissy Brother

sister fuckingSister fucking isn’t what you would expect in my family. My incestuous ways goes back to being a little girl in Canada. Before I fucked my sons, I fucked my brother. When I say I fucked him, I mean I fucked him, usually with a strap-on. My brother was a sissy. Your typical momma’s boy. Raised by a single mother with 4 older sisters; easy to understand how he got that way. I took it upon myself to toughen him up a bit. All the nights I fucked his back door with my strap on, sat on his face smothering him with my pussy and fe.d him my feet made him soft not strong. Essentially, I created another sister.

kinky phone sexHe paid me a visit last weekend, and even my sons made fun of him. They called him Aunt Mark. I got to show my sons how we treat sissies and subbies in our family. As I was sitting on Aunt Mark’s face, making him clean up his nephews’ spunk in my pussy, the boys started circle jerking on him. It was such a site to see. Three boys more than half his age, with bigger dicks taunting and teasing him about his sissy click He was enjoying the humiliation. It made him lick my sloppy wet pussy faster. My son’s were going to cum on their Aunt, but my eldest boy thought it would be fun to drop their loads in my ass and make her scope it out with her tongue.

sissy phone sexMy sons got hard again watching Aunt Mark eat their cum out of her sister’s shitter. I pretty much farted that boy seed out all over his face, which made my boys hard again. I let them cum in their Aunt Mark’s mouth this time. My sons used her all weekend as a slave. They will use you too if you have a worthless pecker and are a momma’s boy!

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sissy training

Adoption with Kathy

Mommy phone sex

I love taking in stray whores.

They come to me looking for work.

I clean them up and fuck them for free.

I get them working for me and pay them to fuck other men!

I love adopting my little whores so much I went and adopted myself a son.

I love my sweet son.

He is treated like a sweet little angle.

I put him in diapers, give him bottles and he even sucks his new mommies titties.

I love cleaning his ass after he uses his diaper.

Ageplay phone sex

After he gets all cleaned up this naughty mommy sucks his dick.

I love sucking his balls and his cock.

His dick is so big I even ride him.

He is such  a good son.

I love my sissy son.

He lets mommy dress him up like a little baby whore.

He loves it when mommy puts him in a diaper.

My big sissy son loves to be treated like an adult-baby!

 

He Is So Shy

kinky phone sex camillaHe wanted to be my little girl so badly. I could see the longing in his eyes when he watched me get dressed and put on my make up. Finally I took him in my lap and wrapped my arms around him. I let him place his head on my chest as he sat without saying a word. He just sat and listened to my heart beat. We sat like that for a long time before I took his hand and led him to my room. Sitting him on my vanity stool i stood behind him and began combing his hair while I told him that inside there was a beautiful princess longing to get out. I continued to quietly tell him that I wanted him to be my special girl and before long he began to come out of his shell and she was born. Her eyes lit up like a Christmas tree when I took out the make up and began to transform my sweet princess into what she longed to be. She began talking little by little as I led her to my drawers and told her she could not only pick out anything she wanted but she could keep it too. Soon she was babbling on and telling me all of her hearts desires I am working on making each and every one of them come true for my beautiful, blossoming sissy princess. 

Picture Day

mommy phone sex darlaHarley is so cute. He wanted to play photographer and take sexy pictures of his hot mommy. As soon as he told me what he wanted to do my pussy got so fucking wet. He was in charge of the entire session. He told me to undress so he could get some good pictures of me naked. He told me how he wanted me to touch myself all while he snapped pictures. He had a box sitting next to him. He reached in and pulled out a pair of my sexiest panties and made me put them on for him. He had me pull them up and into my pussy all the while my pussy is pumping juice while he snaps pictures. He has me take the panties off and makes me put on a pair of pantyhose. I love the way he tells me what to do while he takes more pictures. I can’t help but be turned on by his hard dick and I start to cum hard in my pantyhose. I am begging him for the shoot to be over so he can lick my pussy clean. I need to feel his lips on me and I need to put my mouth on him. I love my sweet little sissy boy.

Oh Sissy Your So Fine

kinky phone sex sissyAn ode to Sissy, to the tune of Oh Mickey…kinky phone sex sissy movie

Dancing Sissy

Oh Sissy You’re So Fine

Oh Sissy, you’re so fine
You’re so fine you blow my mind, hey Sissy,
Hey Sissy

Oh Sissy, you’re so fine
You’re so fine you blow my mind, hey Sissy,
Hey Sissy

Oh Sissy, you’re so fine
You’re so fine you blow my mind, hey Sissy,

Hey Sissy!
You’ve been a sissy all your life and that’s a little long
You think you’ve got the right but I think you’ve got it wrong
Why can’t you prance all day not just when you’re home, Sissy

Jingly jangly bell wearing pansy you are such a joke
You’re little bitty clitty can’t even give a poke
That pink penis pouch is the final note, Sissy

Oh Sissy, what a pity you really are a man

You really look so fake as you approach the stand

Oh Sissy, you’re so pretty, can’t you understand
It’s girls like you Sissy
Oh, what you do Sissy, do Sissy
Don’t be a man, Sissy

Hey Sissy!kinky phone sex sissy2

And now Sissy here are Miss Darla’s demands as a superior female:

1. You will sing this tune in it’s entirity every day from now until Vaca to your Princess in addition to singing it to each and every one of us while we are on Vaca

2. We have all come to the conclusion that as our very own Sissy you should honor us with more money for our Vaca. After all we work so hard at humiliating you and we show great restraint when it comes to not using your name in our blogs.

In conclussion your wondrful Princess has given us all permission to commit he final act of outing you by adding your name to our blogs. Won’t “Oh Sissy” sound so much better as “Oh Michael Fra….”?

Someday I Will Be…

mommy phone sex darlaA superior female just like you….yeah right, in your dreams Sissy. But I know that is your dream because imitation is the sincerest form of flattery and you look so cute in your playboy bunny costume.  All the jingly jangly jewelry you an buy, All the pretty frilly dresses you can acquire. All the visits to the beauty parlor for waxing and eye brows and manicures. And still you dress in those silly man clothes every day. You go to that man job and talk in that ridiculous man voice. You tell people what to do and make them think you are a real man. You play golf and go to country clubs and dinners and act like you belong. We all know that you really love to dress up like a superior female and that you hide your real hearts desire from everyone. You can’t hide from us. We all know the real you. Should we tell the world all about your lump of shame and how good it feels to have it in your pretty panties. How it makes you want to rub your clitty with that poop. That that is why we call you a poo poo pansy. We love you Tinkerbell. You just keep on living your fake man life and we will try to keep your little secret. kinky phone sex sissy

Sissy Boy

sissy training phone sex michaelI saw this poem and it struck a soft spot in my heart for both my dear little sissy boy and for our very own special sissy. I hope that all my sweet sissies out there enjoy it too. Goodness knows I love each and every one of you and enjoy our sissy time together.

The Sissy Boy

By: Edwin Carty Ranck

Beware the Sissy Boy my little one,
Not because he’s very wild;
The Sissy Boy is never that,
Although he’ll run if you say “Scat!”
The Sissy Boy’s infinitesimal,
He is not worth a duodecimal.

If you should take a custard pie
And hit a Sissy in the eye,
He would not go before a jury,
He’d only blush and say “Oh Fury!”
For he is perfumed, sweet and mild,
That’s just his kind, my dearest little one.

One should never strike a Sissy,
He is too lady-like and prissy.
You do not need to use your fist
But merely slap him on the wrist,
And if this will not make him budge,
Then glare at him and say “Oh Fudge!”

The Sissy sports a pink cravat
And often wears a high silk hat;
His voice is like a turtle dove’s
And he always wears the “cutest” gloves.
At playing ping-pong he’s inured,
And his finger-nails are manicured.

He uses powder on his face
And his handkerchiefs are trimmed with lace;
He loves to play progressive euchre
And spend his papa’s hard-earned lucre.
He wears an air of nonchalance
And always takes in every dance.

Socially, he’s quite a pet
And always fashionably in debt.
He hates to be considered slow
And poses as a famous beau.
He loves to cut a swath and dash
When papa dear puts up the cash.

This, my littleone, is the Sissy Boy
Who acts so womanly and coy.
His head’s as soft as new-made butter;
His aim in life is just to flutter;
Yet he goes along with unconcern
And marries a woman with money to burn.

We love you Sissy!

Colors Of The Rainbow

sissy training darla (2)It’s time to introduce him to the wonderful world of variety…yes I think he is ready for the gay, lesbian, transgender and trans sexual community. I think he will fit right in with all the colors of the rainbow out there. So this weekend he is spending the entire weekend with a fiend of mine that is gay and going to throw a bash for a wide assortment of people with a wide variety of sexual appetites to introduce him to. The entire weekend is going to be recorded so that I don’t miss a minute of them teaching him the ways of their life style and how they explore sexuality. I can’t wait to see the new and unique fetishes they introduce him to and to find out what turns him on and what doesn’t . This is a stepping stone that he has earned and is so very ready for. I haven’t told him yet but plan on telling him at dinner tonight and my pussy has been so wet thinking about it and imagining the excitement he is going to have at the prospect of it all.