Sunday Brunch

"I just think it's wonderful!!!"
"I quite agree....please tell me my dear how you got him to do it for you?"
"It was really quite simple.....I locked his.....well I guess you could call it a penis....anyway....I locked his little penis in a chastity cage....and after a couple of months he became much more agreeable....I could have my lovers whenever I wished...he would even suck them to make them hard for me....it wasn't such a jump from there to make him my maid....and he's so wonderfully attentive  now....I laugh when I think about how he pretended to be a man.....now that he's had a few in his mouth he knows what a man is...."
"But if he is in this....chastity cage....does that mean he never gets to cum?"
"Possibly...."
"When was the last time he.....you know....had a release?"
"I don't remember....quite a while ago I think...."
"And how does he feel about that?"
"Who cares!!!!"
And all the women started laughing....

Like Any Couple

Like any couple we sometimes just lie in bed together and talk....

Pressure

I don't think she's trying to pressure me into a decision but I think maybe.....
She told me a few days ago that if I wanted to have beautiful breasts like hers she would gladly make that happen for me....
Now she's always whispering to me about how she'd love to play with my tits....she'd love to cup them in her hands and suck my hard nipples....
OMG.....I'm so not sure about this but every time she mentions playing with my boobs I start to think that maybe that's what I want....
It seems so irrevocable.....I'm just not sure what I want and she seems to have made up her mind.....although she says it's my decision to make....
I so want to please her....I'm so used to doing what she says.....but I'm really just not sure about this.....it could be wonderful or it could be something I'll regret and probably ultimately blame her for....
I just don't know which way to go.....

Enjoy It

As Stacy slipped her big cock inside me my wife spoke softly to me....
"I love you....and Stacy loves you too...enjoy it!!!!"

Cuckold

I could still taste his cock in my mouth and even though I was caged my panties were still wet with my sissy drippies....
I watched him take her hand and lead her to our her bedroom but even though I was in slutty lingerie.....even though I was a sissy cocksucker.....even though he was going to fuck her all night while I watched or listened.....
I saw that little gold band on her finger that meant she was mine.....you may fuck her....she may suck your cock.....maybe she'll give you back door access....but after all is said and done she's still married to me and after you're gone we'll cuddle together....and we'll giggle like girls together....and she'll fall asleep in my arms.....and tomorrow we'll still be in love!!!!

Sissy Training - Basics

A proper sissy always bends at the waist....
It's a basic every sissy should know!!!!

Silence

She looked down at him....his eyes closed....his mouth so inviting!!!! In a moment her lovers cum would be dripping onto his tongue....and they both knew it....he had accepted it in silence...and she wanted this so badly....there would be years to talk about it, but for now they both wanted this....she was so in love with him....and he was so in love with her!!!!

Warm Enough

It's already warm enough.....I don't need to cover it!!!!

Hump Day

Sometimes you learn that even the biggest things can be handled by Hump Day leaving you with nothing but fun till the weekend!!!!

Could It Be

For Benny it was like finding the Holy Grail!!!!
Could it be real.....could it be true....
How could he not buy it!!!!
Wearing an invisible bra......it was the answer to his prayers!!!!

Something New

I had thought all that time she spent teaching me to put on makeup would be enough....but later she taught me another use for lipstick that had never occurred to me!!!!

Not That Much Different

I'm not that much different from all you guys out there reading my blog....I put my bra on one hook at a time just like you do!!!!

Monday ManCandy

That's a good boy.....she knows what's best for you!!!
Even though you missed a little she'll make sure to help you scoop it up so you get your full breakfast treat....she's very good to you like that!!!
Now after you clean up it's time to pull up your panties and get on with your day you have so much to do!!!!
ManCandy!!!! Giving you the energy you'll need to start the week right!!!!

Sunday Brunch

I know the tray was especially for her but I couldn't resist just trying a little taste....

One Little Condition

No she never really went "all the way" but she would allow him to do almost everything else as long as he fulfilled her one little condition....and the skirts and petticoats were very comfortable after he got used to them!!!
It became so normal to him that he had trouble doing it any other way....

Punishment

She realized after a while that she had been going about his panty punishment all wrong....
"No panties for you today young man!!!"
"All day!!!"
"All day....maybe next time you'll be more careful than to drip into them!!!"

Look

"Look what I got today Honey....what do you think?"
"Ohhh it looks sexy.....is it your Halloween costume this year?"
"Halloween.....no....it's for you actually and I expect you to wear it all day while you clean the house!"
"What! I won't.....what makes you think I would do that?"
"Really? I just moved your release date back another three months....you must really be enjoying your chastity!"
"Three Months!!!! That's not fair....I..."
"Four months...."
"If I put the dress on can I get a reduction back to the two weeks I had left?"
"Five months...."
"Thank you Sweetheart....I love it.....will you help me to put it on so I can be a proper sissy maid for you?"
"Six months...."
"I've got it.....give me a couple of minutes to put it on .....I can't wait to serve you as your maid...."
"Good Sissy, my friends should be here soon and I want you properly dressed to meet them!"
"Your friends!!! I can't...."
"Seven months..."
"I can't wait to meet and serve all your friends Sweetheart!"

I Told You

"I told you didn't I? This white sissy bitch is fantastic!!!"
"Yeah Baby but I'm still not so sure about letting you fuck his wife..."
"Sissy....get your tongue up in that ass.....make her happy so I can make your wife happy!!!"
What's a Sissy to do.....I had to keep my wife happy so I'd do anything....and it was so much fun too....and I was pretty convincing....they're both coming over soon and I'll be expected to keep her happy while he and my wife....well do I really have to spell it out for you....

I Like To Think

When I feel them get hard in my mouth I like to think that they appreciate all the effort I've put in to be pretty for him!!!!
But maybe they just enjoy having a hot sissy slut sucking their manly cocks....
Either way works for me!!!

Pardon Me

He was a very handsome man and my wife assured me he was blessed where I had been cursed....
She introduced me as her Sissy Husband.....and I blushed to be introduced like that.....it was embarrassing to acknowledge being a sissy in front of a man I had never met before....at least she didn't call me Kaaren.....
I didn't know what to do so I put my shaking hand out....I wasn't really thinking.....
He looked at my outstretched hand for a moment and laughed....
"You'll have to pardon me Sissy but both of my hands are busy inside your wife and I'd hate to be rude after she has been so nice inviting me in!"
"I.....I understand...."
Again I didn't know what to do so I gave him a curtsy and headed for my bedroom....
Their laughter followed me out of the room....

Out of the Park

A Fantasy

Remember me Coach.....you used to laugh at me because I could never get a hit....you used to call me a sissy.....well you were right about one thing.....I am a sissy and I'm proud of it.....but you were wrong when you said I'd never get a hit....just watch me knock these two balls out of the park!!!!

Fluffing

Yes I've fluffed him before.....he's actually been one of my favorites!!!!
So when I got down on my knees and started sucking him it was like old times for both of us....
Except it was 10 o'clock in the morning....
And she wasn't going to be home for hours....
And he didn't have a date with her tonight....
And there was no one there to tell me to stop!!!!!

Hump Day

Some weeks are easier than others and this Hump Day finds everything going nice and smooth....

Explain It To Me Again

"Explain it to me again Sissy...."
"Well...you remember how you said I should get out of the house....maybe volunteer somewhere?"
"OK....yes....go on...."
"So I thought I'd volunteer up at the Nursing Home.....you know....maybe read to them or play cards or something...."
"And...."
"Well we were playing cards and....one thing led to another and....well.....the next thing I know we're playing poker....and I just kept losing....and....well....next thing I knew I was on my knees and he was gasping and clutching his chest...."
"Oh my god Kaaren, he didn't....."
"He did!!! It shot everywhere!!!! He hadn't cum in decades and he had quite a backup! The nurses came running as he was shouting "Oh My God" over and over....and they said I couldn't volunteer there anymore!!!"
"I see....maybe staying in the house isn't a bad idea for you!"
"Whatever you say Ma'am!"

All You Need

"No Sissy....your wife said you're not allowed to cum.....but I know how much you want to be covered in it so here's all you need...."
"Thank you Sir!"
"You're welcome Sissy.....now get busy cleaning that up then you can suck me till I'm ready to fuck your sweet little wife.....again!"
"Yes Sir!"

Do You Remember

Do you remember your fist dress? Do you remember how it felt? The hem touching your thighs....the zip up the back that seemed so impossible....do you remember?
The girls always looked so comfortable and natural in their pretty dresses but you felt so much excitement and you wondered if they always felt this way....
The first dress means a lot....mine was pink....appropriately enough....and it had a peter pan collar which I loved then....and still love now...and I had never felt so different....so unlike the boy but not yet the girl.....I longed to be caught in it and I was terrified of being caught at the same time!!!!
I remember how the world fell away when I put it on....I became a new person....
That dress changed me....or maybe it had opened the door to the me that I am now....
Anyway...do any of you remember your first dress....if so I'd love to hear your experiences!!!

Monday ManCandy

"What do you mean you don't have time for breakfast??? You need a good breakfast to start your day!!!!"
"It's alright....there's a place where I can get something hot that's right on the way....I'll get something there!"
"As long as it's not junk food....."
"All natural, organic and full of protein!!!"
"Alright then go on and have a good day!"
ManCandy!!!! Breakfast, lunch or dinner....it's always available somewhere!!!!

Sunday Brunch

The girls all agreed that this was their best brunch ever!!!!

Sissy Training - Professional Help

Sometimes with the more reluctant sissies it is advisable to bring in professional help to further his training! An experienced domme will work wonders on even the most stubborn sissy!!!!
You can leave most of the training to the pro, however, the first time Sissy sucks a cock it is important that you be there! Sissy has to know that you watched him sucking a cock so that when you want him to suck one for you he'll have no reason to refuse!!!!

The Tie

"But Mom....I don't want to wear a tie....I hate it!!!!"
"Well you have to wear it so just get used to it!!!!"
"But Mom....it's so uncomfortable...."
"Well maybe you'd like to wear your sister's dress again....with all those pretty petticoats?"
"No Mom.....please it's just the tie...."
"Oh you'd look so pretty.....you'd have to wear her ruffled panties and the bra with the ribbons and bows.....then the petticoats....at least three I think....and then that pretty green dress.....and maybe you'd fit into a pair of my high heels....oh my you could be the belle of the ball....is that what you'd like?"
"Oh yes Mommy!!!! That's exactly what I'd really like....can I....can I please!!!"
"Of course you can Sweetheart.....then maybe a nice long spanking over my knee!!!"
"Oh Mommy....."

Why

"Holy crap Tommy....what's going on....why are you dressed like a girl?"
"I just put on some of your sisters clothes.....you don't mind do you?"
"Jesus Tommy....what the hell?"
"Why don't you let me suck your cock.....it'll be just us....it'll be our secret....you'd like a nice wet sloppy blowjob, wouldn't you?"
"Yeah but...."
Several minutes later as he was zipping up he looked at his friend who was licking cum off of his fingers....
"It's s a secret right....."
"Sure it is....listen do me a favor.....when you go back outside would you ask Charlie to come in....there's something I'd like to talk to him about...."
"I'll bet it's a secret right?"
"Of course it is...."

A Little Under the Weather

I've been feeling a little under the weather since yesterday evening....been running a fever on and off....my wife's assistant Stacy has been here looking after me and I finally convinced her I'm well enough to update my silly little blogs....
Hopefully resume my regular posts by tomorrow morning
Love
Kaaren

Never Dreamed

Young Kevin never dreamed that just trying on his sister's school uniform could lead to such a wonderful adventure!!!!

Hump Day

You feel like the job has got you by the throat sometimes but no matter.....it's Hump Day and it's all easy going from here!!!!

School Days

The bell would ring in a few minutes so I had to hurry....
In a few minutes I'd have a nice long queue outside stall 3....and at ten dollars each I figured by the time I graduated I could be a millionaire!!!!
Teenage boys don't last long and I was already onto my fourth when I heard the door slam open and the Dean's voice booming, demanding to know what was going on in here....
I heard the boys scatter as the poor Freshman in my mouth withered....but he had paid his money and despite his terror of the Dean he finished in just a couple of minutes!!!!
He zipped up and literally ran past the Dean as he hoped to avoid punishment!!!!
The Dean stepped into the stall as I was wiping my lips and fixing my makeup...
"I see you're still in business!"
"Yes Sir....still doing a thriving business!"
"Still free for the faculty?"
"Of course Sir....you know I love the faculty!!!"
"I have ten minutes till my next meeting...."
"Ten minutes!!! Maybe you can go twice!!!"

It's Good To Be Home

As she fucked me slow and deep I could only think of one thing....
It's good to be home!!!!

Monday ManCandy

It's always nice to share breakfast with a friend!!!! Who doesn't enjoy that creamy treat that stays with you all day!!!! The flavor lingers on your tongue long after you and your BFF have had your fill!!!!
Your texts back and forth about how wonderful it was just makes you want more....
ManCandy!!!! There's always more than enough for everyone!!!!

Vacation Accomodations

The hotel was really beautiful....and judging from certain clues I get the feeling we've been here before...

Sleeping Late on Vacation

She allows me to sleep late on vacation....after all I really don't have any housework to do.....so I like to sleep past dawn!!!!
And when I open my eyes and see her waiting for me.....smiling and hard ....I know it's going to be a great day!!!!

Vacation Correction

"Did you bring that baby blue set with all the bows....I'd like to see you in that tonight?"
"No Ma'am....but I have something just as pretty in here!"
"But I want you in that set....did you pack my hairbrush because we're going to have to talk about this!"
"Yes Ma'am....I'll get it for you right away!"

Weekend Vacation

It was only going to be a weekend trip so I just grabbed my small bag to take with us....after all you have to make sure, even on a short trip, that you take the essentials with you!!!

Going to be Traveling

We're hitting the road this weekend to visit some friends in their new home in Connecticut....so keep an eye out on I-95 North and maybe you'll see us go by!!!!
I"m not allowed to say where exactly we're going but it's just outside of a touristy town that has a really famous pizzeria.....if I say more than that I'll have a very uncomfortable drive after a serious spanking!!!!

A Few Minutes

"I think that's enough Sissy.....let's get you back in your cage....I don't want you spraying your Sissy cream all over my toes!!!"
"Oh pleas just a few more minutes!!!! It feels so nice.....I promise I won't cum....I promise.....and if I do I'll lick it all up.....please!!!"
"Sorry Sissy.....get the cage.....even the possibility of you cumming isn't allowed!!!"
"Yes Ma'am!!!"

It Doesn't Matter

It really doesn't matter where you are....sometimes you just have to stop and tuck it back again!!!!

Sissy School - So Much

"I don't know why I ever listen to you Kaaren!!!!"
"Because we have so much fun Leeanne...."
"But we always end up getting spanked!!!"
"Like I said....we have so much fun!!!"

Fluffing

Sometimes she might decide to keep you fluffing until he cums in your mouth....her hand on your head...tells you she wants you to have the first....she'll take seconds today!!!

Hump Day

It's Hump Day!!!! As hard as it's been you can definitely feel that the end is coming soon....really, really soon!!!!

Awake

Awake!!!! Of course I was awake....but to be honest....I was just so exhausted I really just couldn't....I honestly dom't know where she gets her energy!!!!
So, yes of course I heard them.....you'd have to be stone deaf to not hear them!!!!
And yes the bed was rocking....and of course I could feel it.....
But I just needed to sleep.....my peeks at the clock showed me how little sleep I was going to get...
It's not that she doesn't care but she forgets sometimes how long my day really is....
But I'd be lying if I told you I wasn't tempted to roll over and start using my tongue wherever I could......

Surprised

I didn't even hear the gate....perhaps I was dozing....
"Hello Sissy....is your wife home?"
I was startled and realized it was my wife's assistant Stacy....
"Yes Stacy she's probably in her office...."
"What did you call me!!!!"
"I'm sorry.....yes Mistress Stacy....she's probably in her office!!!"
"So much better Sissy....maybe we'll talk about that misbehavior later!"
"Yes Ma'am!"
She's a keyholder and she has privileges with me and, to be honest, she spanks harder than my wife does....and she has a real strap-on fetish too!!!!
Not that I'm complaining mind you....she's one of the very few women that my wife allows to play with me....
I can suck all the cocks I want but she is very jealous about other women....

Let It Wait

"But I have so much to do....I have to put the coffee on and start preparing your breakfast and laying out your things...."
"Let it wait.....come to bed with me Sissy.....imagine when he wakes up to us sharing his cock...."
"Sharing?"
"Sharing Sissy.....it's magnificent....and it really needs two of us to do it justice...."
"Well if it's what you want...."
"Come to bed Sissy...."
"Yes Ma'am!"

Smiles

Of course I'm all smiles...I'm heading to a party wearing my pretty white summer dress....and everyone there knows Kaaren and none of them knew the boy that was there before....
What's not to smile about!!!!