Tag: sissy training

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.

Spoil Me, Sissy Boy

sissy phone sex

The reason I play with other boys Daddy is because I have to. You know that itty bitty dickie of yours isn’t enough to satisfy me. Other men can make me scream, but no one spoils me like you do Daddy. I think you like it, don’t you? Seeing me gag on big, fat cocks must make you jealous though. Does it ever bother you when I play with them wearing the cute outfits you bought me? If it does, I don’t ever plan on stopping.

It’s so much fun seeing you stroke your tiny clitty while you watch me play with real men. I bet you wish sometimes that you were one of them, but you’ll never be like them. No matter how hard you try nothing will make you less pathetic or make your pencil dick grow. Just accept it. You can still make me happy by showering me with attention and gifts. That’s all you’re good for anyway. I’m the perfect Princess and your my little toy.

kinky phone sex

Consider yourself lucky. I don’t get bored with you like I do with the other boys. That’s because you provide me with constant entertainment. Any guy with a massive rod can make a girl cum, but they can’t make me laugh the way you do Daddy. I’m happy as long as I’m amused. It’s not even that much fun hooking up with men if you aren’t there watching and looking so pathetic. Even if it throws some guys off, I don’t care. I just love degrading and humiliating you that much. It’s so hot to watch you squirm while my tight holes get stretched the way they should. I’ve been thinking about letting you fuck me with a strap on, but even that might be too good for you. Your cock should be locked up, that would make it better

Ms Piggy Sissy Day

panty boy phone sex sissyOur own Tinkerbell Transvestite had another Sissy Day. I would have never guessed just how much Sissy looks like Ms Piggy when she puts on a snout and piggy ears, the only thing that was missing was a curly piggy tail to make our Piggy Pet complete. One thing is for sure, if Ms Piggy ever needs a stunt double, our cross dressing Fairy Fag can stand in for her.The pink dress was perfect, in fact Ms Piggy actually has the same dress. How adorable is that? And did you see the cute little business cards that Princess Levi had made for our Little Dicky Sissy? They are such a pretty pink and Sissy looks so cute on them.sissy training buss card I think Sissy should have to pass them out on her Sissy day and offer her services for parties. I would love to see Ms Piggy Sissy be the entertainment at a cross dressing drag queen’s birthday party. You know instead of a clown or a magician, they could hire Ms Piggy Sissy. That would be one way for our Blackmail Piggy Pet to earn extra money to give to Princess. Princess could be on the phone telling her Sissy what to do. Wouldn’t it be funny if Princess made Ms Piggy Sissy do a lump of shame in her panties in the middle of the party. Everyone would smell Stinky Sissy but no one would be able to see that Little Dicky getting hard because that lump of shame is bouncing around in her pretty frilly panties.crossdressing phone sex bacon Of course Sissy would have to record the entire thing so she could show it to Princess and be critiqued on her performance. I am sure it would take several parties and several tries before Sissy got it just right to Princess’s satisfaction. In the mean time we could all watch Sissy perform for us. And if Sissy made Princess mad, Sissy might find the videos on you tube like those pretty videos of spa day!  In fact there very well may be something in this blog that is linked to the video of those beautiful long eyelashes being applied. What a bid smile Sissy had on her face in that video! Happy hunting I know your going to look for it so you can watch the video.hot phone sex sissy

Incest sex with Nephew Gets Kinky

Incest sex was only part of the bargain between my nephew and me. One afternoon I noticed a camera set-up in the bathroom “hidden”, and approached Mick about it. My nephew had been staying with me for a while off and on. Well, he has been recording me in the bathroom to jerk off too.

As the fair Aunt that I am, and well the therapist in me I wanted to sit him down and discuss some stuff. However, I decided to turn the tables a little. I set a camera up in my bedroom. That’s right I did catch him! Mick had taken to my panty, and lingerie  drawers when I was away. He had become fond of dressing up like a little bitch and jerk off to the feed from my bathroom.

Incest Sex

It appears I have a little Sissy bitch to deal with. My sister and her husband would certainly not want to see what I have caught on video. Looks like I have some leverage and about to have my own personal slave. Well, I cornered him good while he was undressing in the shower. In fact I caught him red pantied and his cock was raging hard.

sissy training

One of the best times to corner a guy about blackmailing him, is when he is in his most vulnerable state. I walked in on him wearing my panties and rubbing his throbbing cock. He was excited and shocked/ surprised that he creamed my panties. I motioned for him to remove the panties and hand them to me. Hesitantly he handed his cum soiled panties over.

“Get on all fours” I commanded Mick, and he did obey. I walked over to him and shoved the panties in his mouth. In turn I slipped my panties off and put the crotch on his nose. I then slid onto my bed and called Mick over like a dog and commanded him to lick my pussy. He obeyed well and I must admit I did like how big his dick has gotten. I would really like to take that for a test drive, and I did.

Needle Dick Bitch

young voice phone sex

Whenever you’re out in public and you hear people laughing I bet you think they’re laughing at you. Before you were probably just paranoid, but now because of me it’s probably true. Remember that picture I took of you in a pair of frilly panties Daddy? There’s no way you forgot about it because you begged me not to share it with anyone else. It was only because that one little picture bothered you so much that I decided to send it to everyone you know.

Don’t worry Daddy I did it from your phone and sent it to all your contacts too and a few from my list as well. My good friend Damon loved the picture too. At first he thought it was a girl, but when he realized it was you he loved it even more. Your sad little clitty is nothing compared to Damon’s thick, 9 inches. He’ll be here soon so you don’t just have to take my word for it.

kinky phone sex

When you first Damon I want you to be a good little bitch. Greet him on your knees and beg for his big black cock. While he is our home, you will treat Damon like a welcomed guest and will do whatever you are told. Any one of your three holes or maybe even all of them belong to Damon. If you’re luck you might just get to watch your little Princess get filled by his massive fuck stick too, but honestly I’ll probably just watch you suffer.

While you’re being used and abused by Damon I’ll be taking pictures for our scrap book. Maybe one day when I’m feeling bored I’ll upload every last one of them to the internet and a video too! If I wear stockings you’ll probably cry because you have a perverted stocking fetish. You’re such a big baby that you can’t stand being teased with them sometimes even if it’s only for a second. That’s okay Daddy go ahead and cry if you want to. I’m sure most people already know how pathetic you are, but just case anyone ever questions it I want to have proof.

sissy phone sex

Sissy’s Easter Surprise

Sissy phone sexSissy is going to be hopping down the bunny trail with a basket full of goodies and her cotton tail. This is the one year anniversary of my wonderful idea for Sissy to dress as a bunny. Her costume is so tight and revealing and it shows off her wonderful legs.  She is going to be so cute Princess Levi is going to make her hop around in her pretty pink bunny outfit with her panties full of poo like a good poo poo pansy. Bouncing around in her lump of shame. A pretty little sissy for the world to see. Her gold hoop ear rings bouncing as she skips to the jingle jangle of her pretty bracelets. Sissy is so happy in her Fairy Fagot world, humming her favorite song “I’m A Poo Poo Pansy”  a tune she wrote all by herself for her Princess.Mommy sex I think for Easter Sissy should write a new song to the tune of  “Here Comes Peter Cotton Tail” for us. I have to say the bunny costume is the best idea I have ever come up with. It doesn’t seem like it’s been a year since the first time she put it on and was so nervous about going out in public like that. I believe Sissy was told to get a Piggy costume next, to show everyone that she is a Piggy Pet as well as a Tinkerbell Transvestite. I want to see Sissy dressed as a dolly with a pacifier and a diaper and a baby bottle and a big rattle for her next Sissy day. She should have to go out in public for the entire day and have to stay in that diaper all day and not be allowed to go to a regular bathroom till the end of her Sissy day. She should wear a bonnet and a little sissy dress that is real short with her frilly panties showing from under neath. I know that would get a lot of attention! Happy Easter Sissy, it has been a year full of wonderful Sissy days, I can’t wait to see what this year brings…..

 Sissy training