Friday, April 30, 2021

When He Thought About It

When he thought about it he had fucked her hundreds of times....he'd given her hundreds...maybe thousands of orgasms....and he did it all without her releasing him from the cage.....he felt the only satisfaction he was allowed....the satisfaction of a job well done!!!







A Good Start

"Well....it's a good start to your life as my sissy cuckold....chastity and panties....get used to both of them....now we have to talk about all this body hair....you know it has to go don't you...."
"All of it?" 
"I want you to be as smooth as I am!!!"
"But my co-workers....my friends....they might notice....what will I tell them???"
"Tell them that your wife is feminizing you, and that when I'm done, maybe I'll have you suck their cocks...."














Thursday, April 29, 2021

Waiting

Every time she goes out, I find myself waiting at the window for her to return....ready to provide whatever service she might require....











A Drive

"That guy in the SUV is looking you over Sissy!!!"
"He is not...."
"Oh yes....he's looking at your legs in your pretty stockings....maybe we should show him more?"
"No....let's just ignore him....the light will change in a moment...."
"I want to show him what you have to offer a stud like him Sissy...."
"Yes Ma'am...."
Unfortunately a few moments later the light changed and he was gone....












Wednesday, April 28, 2021

Hump Day

 Even though work has you tied up in knots...you still get to enjoy Hump Day...after all we all need a break sometimes!!!










First

"You go first...."
"No you go ahead...."
"Really....you go first....I insist...."
"I'd rather watch you go first...."
"And I'd really rather watch you go first...."
She had on my favorite strap-on and he was hard and wet....at least he was a minute ago when he was in my mouth.....now all I wanted was for them to just decide....flip a coin for goodness sakes!!!!!












Tuesday, April 27, 2021

Memories

When he was settling his mother's estate he went through all of her things....and for a moment he was that awkward boy once again....going through his mother's things....











Traditional

I don't go for all that new fuss....I'm a much more traditional sissy maid....
Nothing fancy...just get down on my knees and suck his cock....it's what my wife trained me to do and I do it very well... 














Monday, April 26, 2021

My Analyst and I Go For a Stroll

It had been so long since my last session and there were so many new things I wanted to discuss with Dr. Dee...
She thought it would be nice and less Covid intensive if we met in a local park and talked as we strolled in the open air....
I told her about my new mask fetish and she laughed....
"Only you Kaaren....it's so typical....you desire anything you can't have....."
It was then that I noticed her on the bench....I nudged Dr. Dee and nodded in her direction....
"Is it possible....do you think that's one of the benches?"
"She does look kind of masculine in a real feminine kind of way Kaaren.....maybe....lets go and see...."
We walked up slowly and the girl on the bench eyed us as we approached....
"Excuse us....my patient and I were just wondering if perhaps you needed any help..."
"Your Patient?"
"Dr. Dee is my therapist....we were wondering if anything might have happened to you since you sat down on this bench?"
"No it's been a slow day....I'll tell you what....you're both kind of cute....I'll do you both for $75...."
"Oh no my therapist and I still have so much to discuss...."
"Not so fast Kaaren.....maybe this would be good for both of us...."
"Well if you think it's OK then I'm OK with it...."
And the three of us walked off....Dr. Dee, me and the young man who had been the woman sitting on the bench moments ago....
















Monday ManCandy

"Are you dressed yet?"
"Yes Ma'am....I'm wearing the dress you laid out for me...."
"Very good....have you said your prayers?"
"Yes Ma'am....but I'm still not a real girl...."
"That's alright....you just keep trying....have you had your breakfast?"
"Just finishing the last drops now Ma'am...."
"Did you enjoy it ?"
"I always enjoy it Ma'am....breakfast, lunch or dinner...."
"Alright then....you run along while I have my breakfast..."
"Can't I stay and watch....please?"
"You're incorrigible....maybe some other time...."
ManCandy!!! It's a a tummy filled with love!!!!















Sunday, April 25, 2021

Sissy School - A Weekend Visit Home

It's always nice to be home....and although my wife and her lover had originally sent me to Sissy School to humiliate me it really hadn't worked out that way....I loved it....I loved everything about it.....ans although I had made her angry by seducing her boyfriend, her sister and almost all of her neighbors....she still made sure I was wearing fresh new panties before she put me on the pink bus to send me back to school....
There was a lot of shenanigans on the bus and it was a long ride, so I couldn't guarantee the condition of the panties by the time we got there....maybe that was why she was always buying me more!!!!













Prelude

When she takes me over her knee the spanking sometimes doesn't begin for quite a while as she explains why I'm being corrected....and I'm very ready by the time she begins spanking in earnest....


 
 
 
 
 
 
 
 
 
 
 
 
 


Saturday, April 24, 2021

Saturday Matinee - The Secret Below


 
 
It had been a wonderful dinner party....all the best people were there....Lord Toban was the perfect host.....but Jerry Anderson was not the perfect guest....
He'd come along as a guest of the Earl of Dusquene....and his interest was strictly in the real estate value of the old castle....
He'd made a fortune in transforming these old ruins into modern hotels and condo's and this one looked like it could be a huge payday if he could talk the current Lord Toban into selling!!!
He did the usual small talk with the snobs....Lords and Earls and Dukes....pompous asses all of them....they were dinosaurs trying to live in the modern world.....he would buy them all out and turn their entitled world into a tidy profit....
He wanted a tour of the place but he kept being put off....he needed to see just how poorly the old dump had been maintained....sure the rooms he'd been shown were beautiful...but that was just the surface....he needed to see the problems he'd face at the bottom....
His guest room was richly appointed and he was looking forward to it being a guest suite or master bedroom.....he could already count the millions he would make from this dreary old dump!!!!
After they had all retired, he slipped out to do his own tour of the place....
He slipped down the stairs and found the entrance to the lower levels in the kitchen.....just where he thought it would be.....but as he was about to open the door he heard approaching voices....
It was that fat couple......Lord Somebody and his fat wife....
They were laughing and chatting as they headed to the door to the cellars....
"This is always the best part of Toban's dinner parties don't you agree?"
"Oh yes my Dear....I always look forward to it...."
And then the door closed behind them....
What the hell was that about.....
Jerry slipped through the door...trying his best to not make a sound....but he followed the laughter and conversation of the other two till he came to a closed door....
Their conversation soon changed to a very sexual nature and words that he wouldn't have believed they even knew came to his ears....some actually making him blush....
But there's were not the only voice....
There was another.....another voice....obviously female.....who begged them to stop....who pleaded with them for release....
Her plea's were met with derisive laughter and then the sounds of sex....moans and groans and cries of orgasm from both of the nobles....
Shortly after they left the underground room....they hadn't bothered to dress and he watched their naked bottoms as the climbed the stairs.....
He had to see what was behind the door....this was so crazy....
He pushed open the door and found a dimly lit room....a woman was chained in the far corner....she was quietly weeping and hadn't noticed him until he shut the door behind him....
She looked up and despite her obvious misery she smiled....
"How may this slut serve you my lord?"
He was a ruthless businessman....he'd screwed lots of people....but not like this!!!
"I'm getting you out of here....then we'll go to the police....and we'll have the whole lot of them locked up...."
"You'd be willing to set me free.....I never dreamed I'd be free....I've been here for so long..."
"Yes I'm going to set you free....and after the scandal of all this, I'll be able to buy this place for next to nothing!!!!"
 "Please hurry....break my bonds....it's been so long....is Victoria still the queen?"
He ignored the question as he set to breaking the manacles that held her so cruelly....
and finally the last link in the chains was broken and she rose....the light was playing tricks on his eyes as the whole room seemed to glitter around them....
Where the abused girl had stood there was now a handsome young man....and before he could say a word the man grabbed him and kissed him....full on the lips....and then smiled and opened the door....
And there they all were....waiting....smiling....and before he could run they were upon him ....and the manacles were placed on his wrists....and he was a prisoner.....and somehow he was a woman.....
And they all took their turn proving to him that they liked him much more this way....




















Sweet

"You're right Baby,,,,your Sissy husband has a sweet ass.....just like a girl.....I wasn't sure before but now I can say....I'd fuck him if that's what you want...."
"That's exactly what I want.....I want to see his face when you push your cock inside him...."
"I don't know which of you is freakier but let's do it!!!!"



















Friday, April 23, 2021

Humiliation

 Then there was that one time when we couldn't find the lube anywhere and she decided to use my own natural juices to do the job.....it was humiliating to be milked like that but somehow it was even more humiliating to get fucked hard, pushing my own cream back inside me....










So?

"So Sweetie....I'd like nothing more than to pull this mask aside and take your cock inside my mouth....all you have to tell me is....are you vaccinated?"
 

 









Thursday, April 22, 2021

How Could You

How could you ever go back to boxers and t-shirts after this?








A Show

Our wives wanted a show....but no cummies were allowed....
Steve....excuse me.....Stephanie was enthusiastic....but not too enthusiastic....we wanted to play.....spankings could come later.....
 









Wednesday, April 21, 2021

After He's Gone

After he's gone you come quietly into her bedroom....
No need for words between the two of you....
She feels your tongue....so gentle against her.....
Your intent is not to arouse her....you want to soothe her....
And you do....at first....













Hump Day

 Don't you just love it when Hump Day rolls around and you're done with your part of the project and you get to sit back and watch your colleagues do all the work!!!!











Tuesday, April 20, 2021

Why

Why do we both wear dresses to eat dinner?
Because she likes to have easy access to tease me and I like to have easy access to please her!!!!
Any other questions?











Might Have Been

She was a good Christian girl from a good family....and she married a good Christian boy from a good family as was expected....
She might never have really known how inadequate he was....
She might never have known what a real orgasm was....
Until she caught him wearing her lacy undies....
And he confessed his dirty fantasies....
And he convinced her to do it....
She didn't expect it to be so different....
She didn't expect it to feel so good....
But god....she loved it....and her husband squirted in the little panties as she came hard on the big cock that was changing her world!!!!



 










Monday, April 19, 2021

Still Togther

"So you see Honey....this is why your Daddy and I are still together when so many of our friends ended up divorced.....we always worked things out by ourselves....and Daddy always saw that he was wrong....and after a good spanking we would just move on...."










Monday ManCandy

It's the best breakfast treat you can have....but sometimes I feel guilty about having it all to myself and not sharing it with my husband....

It's the best breakfast treat you can have....but sometimes I feel guilty about having it all to myself and not sharing it with my wife....


 ManCandy!!! It's the guilty pleasure that you can share....if you want to!!!












Sunday, April 18, 2021

Cuckold Wedding

With her new husband waiting for her in the limo the bride was finally able to enjoy her wedding reception!!!!










Sunday Brunch

Another couple of Sunday brunches like this and I'll be able to afford that beautiful ball gown!!!
When would I wear a ball gown you ask....I'd wear it every chance I get....










Saturday, April 17, 2021

Saturday Matinee - Hers Alone


 
 
"But Doctor....there must be some explanation for this...."
"I agree completely....Mr. Blackwell....there must be....but I don't know what it is....I've never encountered anything like it....neither has any of the medical sources I've consulted....I'm afraid it just has to run it's course...."

He'd been having trouble sleeping....no that wasn't right....he had awoken several times that week feeling weird....like he really hadn't slept at all....his thoughts were fuzzy and he had a funny taste in his mouth...but it usually cleared up by mid-morning....and other than fatigue he really just tried to ignore it and get on with it....
This became a regular event for him....usually three nights a week....sometimes four...it was disturbing but not as disturbing as the sudden weight loss.....he was dropping pounds faster than if he'd been on a starvation diet....and his hair was growing much faster than it ever had before....
It wasn't until the soft mounds on his chest had obviously become female breasts that he started seeing a physician!
Then he was passed from one specialist to another as they all poked and prodded him....it was during this time that his....manhood began to shrink....the doctors all measured and compared and still offered him no explanation....
"Have you been exposed to radiation?"
"No!!!"
"Have you been experimenting with narcotics?'
"No....what would that have to do with it?"
They asked him dozens of questions like that....until he finally mentioned the sleep problem he was still experiencing.....
"That could be very significant..."
More tests as the changes in his body continued....his male anatomy was almost completely transformed now....he tried to hide the changes but eventually it was all too obvious....
More tests.....the doctors were baffled and worse....some of them were looking at him very differently now.....he'd heard a couple of them breathing a little more heavily as they examined this new body....
Still the changes continued....his weight had been redistributed....as his waist shrank, his hips and his....breasts had grown....and he seemed to have shrunk a few inches in height....
It was at the clinic in Switzerland that they had found the unknown chemical in his system...and he realized that while he was there his sleep problem had finally cleared up...and he enjoyed real sleep for the entire ten days he was there...
Returning home he found the sleep issue returned immediately....sensing a connection a team had come to his house and swept it for any trace of the chemical they'd found in Switzerland....
Surprisingly they found traces of it on his pillow....
"Does anyone else live here Mr. Blackwell?"
"No, I live alone....why do you ask?"
"I was just wondering if it was possible that someone was giving you this unknown chemical while you sleep...."
He thought of those nights....where he didn't really sleep but still wasn't awake...was it possible....could someone be creeping into his house at night....and doing this to him...
His mind, his thoughts were starting to change....the man was really starting to disappear and a new female was taking his place....His suits were gone....replaced with pretty dresses...his shoes almost all had a heel although he did own a few pairs of flats....his nails had all acquired a layer of polish which he tried to color match to his outfits....
He was wearing outfits!!!!
So he waited that night....long past the time he would have normally been asleep....he waited in his bed trying to be calm as he pretended to sleep....
It was after midnight that he'd heard the sound of his door opening and soft footsteps coming nearer and nearer.....he could actually hear the intruder's soft breathing as he stood over the bed!!!
He gripped the revolver tightly in his hand and surprised the man nearly causing him to drop the vial of clear liquid!!!
"Who the hell are you...."
"I'm an admirer....I've been an admirer since the first time I saw you....please don't shoot..."
"What's that stuff? Is that what made me like this....is that what changed me?"
"Yes it is....I've been doing this for a long time....I fell in love with you a long time ago but you were a man....and I couldn't bring myself to approach a man and confess my love....and I was too afraid to change myself....so you see I had to change you...."
"I don't even know what to say....you bastard....how could you do this to me....I never wanted this.....is there an antidote...."
"No...there's no antidote that I know of....this was going to be the final dose....it would have changed you body and soul into the woman of my dreams....."
The transformed man was at the mercy of his new hormones and instead of attacking the man he put his head down and burst into tears....
Between his sobs he asked the intruder....
"Would you....would you hold me for a few minutes?"
"It's all I've dreamed of for all this time Sweetheart...."
He sat next to her and pulled her into his arms....he stroked her long hair and felt her smooth skin.....
She sighed and nestled her head against his shoulder as she raised the gun and emptied all six rounds into his chest!!!!
As his lifeless body fell  to the floor she reached for the phone and dialed the police....
"A man tried to attack me in my bedroom and I shot him....please hurry!!!"
She hung up the phone and reached for the vial....he'd said it was the last dose and after it he'd be completely changed.....she put it in her bedside drawer....no need for the police to question her about it and after they'd gone she would decide whether or not to complete the transformation....for now she would just enjoy knowing that the decision was hers and hers alone!!!












Suck It

 "Wow....well sure I'd love to suck it....but I bet my husband would like to suck it even more than me.....so let him suck it first and then maybe I'll put it in my mouth....


 
 
 
 
 
 
 
 
 
 
 
 
 
 
 


Friday, April 16, 2021

Working At Home

 Even as the hairbrush landed again I heard several of her co-workers trying to tell her that she hadn't logged off the zoom meeting and that her camera was still on....
As if she didn't know....













Win Some Lose Some

He picked her this time.....I guess that's only fair....he took me the last two times so it was definitely her turn!!!











Thursday, April 15, 2021

Forgot to Tell You

I heard her come in from the garage....obviously I couldn't call out to greet her...
"Sissy....I forgot to tell you I invited my sister to come over.....well....I guess you already know that now...."
 

 









For You

 "C'mon Sissy....this cock is all for you....I can't wait to watch you suck it....c'mon get over here and get him hard with your mouth.....then maybe if you're really good.....maybe he might fuck you too....you know you want to....and even if you don't, it doesn't matter.....what's important is that I know you want to...."
What could he say.....third time this week....she was the perfect girlfriend!!!!











Wednesday, April 14, 2021

Hump Day

It's Hump Day and just like the rest of the week it's been full of ups and downs....










Do It Myself

"You know Homey....I can do it myself...."
She pouted....
"I know you can but I still love to do your makeup....it's like when we were young and you couldn't do anything yourself...."
"But you've taught me so much...."
"Just hush Sissy, and let me have my fun.....I just love to make you pretty....I always have!!!"
"Thank you Sweetheart...."
"Thank you Sissy...."












Tuesday, April 13, 2021

But

"But I like girls....I don't want any men between my legs...."
"Let me prove to you that I'm a girl too...."
"But you're really not...."
"Maybe not physically....but let me prove to you just how much of a girl I can be...."
"Okay....maybe this once...."













Fluffing

Sometimes they're just too ready even before you get to take them in your mouth.....now you need to get them ready again before she comes back.....and you're just the sissy to do it!!!!









Monday, April 12, 2021

Football

"So Michael...can you tell our viewers why you retired from football to pursue this....alternate lifestyle?"
"First off it's a sissy lifestyle....and it's really not so different from football."
"In what way?"
"Well....I get to dress in different clothing....and I'm still surrounded by big, rich, virile men who want to tackle me...."











Monday ManCandy

You shouldn't start your day without giving thanks...so get down on your knees and open yourself up to all the world has to offer....savor all of it but especially enjoy the moment that it fills your mouth with that unforgettable flavor!!!
ManCandy!!! The one of a kind experience!!!

 
 
 
 
 
 
 
 
 
 
 


Sunday, April 11, 2021

Sissy School - A Weekend Visit Home

"What the hell is this....what are you doing Sissy!!!"
"I'm giving her her second ever orgasm...."
"Her second orgasm....how on earth do you know it's her second ever orgasm!!!"
"Because I gave her her first about five minutes ago....at school the teachers usually require five for satisfaction...."
"Well you're not at school now Sissy....so get your tongue out of my niece and pack your bags....I'm calling the pink bus to come get you...."
"Oh my god.....ooooooooohhhhh......"
"There's number two Honey...."
"Up and out.....now Sissy!!!!"
 

 











What They Say

 Remember the old adage.....always dress for the job you want....that's especially important for a sissy to keep in mind....









Saturday, April 10, 2021

Saturday Matinee - A Deal's A Deal


 
 
 He came home from the game like he did after every game....envious...
No, of course he wasn't envious of the other team....they had defeated them easily....they had no one in their school who could compete on his level.....
No, he was envious of the cheerleaders as he always was....
They were so cute and they looked like they were having so much fun on the sidelines...they smiled and cheered whether their team was winning or losing....and the boys flocked to them after every game....
How he wished he could be like one of them....
He thought that he was alone in the locker room but a voice behind him startled him....
"I could make that happen for you...."
"Excuse me....who the hell are you...."
"Oh I was just passing by and I could hear you crying out for help.....I could make you the cheerleader of your dreams if you'd like...."
"I didn't cry out for....who the hell are you?"
"That's the second time you've asked me that....I would think it would be obvious...humans used to be a lot quicker on the uptake in the old days....let's see....I read your thoughts and have appeared to offer to fulfill your darkest desire....who the hell do you think I am?"
"Oh my god!!!"
"Close....guess again...."
"You're him....you're the devil....I didn't think you were real...."
"Really? You can look at the state of the world and still think I'm not real? Well....in the old days people recognized my work all the time....ah well....anyways....how about it....do you really want to be a cheerleader?"
"Not just a cheerleader....I want to be a girl....can you do that?"
"I can do that easy....one snap of the fingers but it doesn't come for free....you studied economics last semester.....no such thing as a free lunch you know...."
"I suppose you want....my soul...."
"Well normally I'd say yes.....but you're a special case....I'm also recruiting for my team....we're going up against the other team soon and I'd like to have a few exceptional players....like yourself....it would mean a lot to me to win just once against him and that insufferable Holy Ghost....just once...."
"So what kind of deal are you offering me?"
"I'll make you into the woman you've always wanted to be....I won't change anything else....your family will be the same...your friends will be the same....and I can even re-direct your girlfriend..."interests"....shall we say....so that she'll still be your girlfriend....no changes to your life at all except that you're female....and as far as anyone will remember...you always have been a girl....in return I get exclusive rights to your immortal soul and you will play for my team from the infernal depths in a championship game against those assholes from above...."
"But how long is the contract for....maybe I should have an agent..."
"Oh you poor schmuck....all the agents are with me....every single one of them sold their souls....for them it was easy....all they wanted was the money....and money is easy for me to get....you've heard of the Federal Reserve....well I could tell you stories...but I'm straying from the point....I could get you any agent you want....living or not....and every single one of them will sell you out to me for the money...."
"Okay so just us then....how long is the contract for then?"
"Don't you watch movies? It's for all eternity of course....I mean if I release you in a couple of millennia, where are you going to go? The other place certainly won't take you and there might not be much of a world still here by then...."
"I guess that's right....but I'd be on the All-Star Team right....so no eternal torture or any of that crap...."
"Well....everybody gets some eternal torture....it's just the way things are made....you can thank the other side for that....I didn't make the rules....but I can try to make it easier for you....at least while you're winning...."
"Okay then....what about now....I don't want to "join your team anytime soon..."
"That presents me with a problem....I need you soon....I don't want you when you're old and gray....I need you in your peak playing years.....so I'll give you....two years...."
"Make it ten....."
"Jeez....you'll be a has been in ten years....I'll go to two and a half...."
"Seven...."
"Two and three quarters...."
"Five...."
"Two and seven eighths...."
"Three...."
"Alright three it is...are you ready to begin your new life...."
"I want to be pretty too...."
"I guarantee heads will turn every time you walk into a room!"
"Alright lets do it....."
In a puff of smoke a document appeared....
"Just sign here....and here....and here....and initial here, here and here....oh and here too...."
"Is that it?"
"Yep....I'll see you in three years....enjoy your new life as a woman!!!"
And then he was alone again....and he was different in some ways....but not in some other important ways....he should have specified....
He was a woman all right....and it was true that heads turned every time he came into a room....but the devil had been true to his word....the only change had been from male to female...he was still the seven foot basketball phenomena that he had been before....
But he trained as hard as he always had because he knew that he had a future in the game....
 

 









Believe Me

"Believe me Sissy....you may be a little uncomfortable now...but you'll thank me for this later!!!"
Maybe he mistook my squirming for complaining.....I was ready to thank him right now!!!










Friday, April 9, 2021

Glass

"Wow Bro....you look so pretty in my old Prom dress. I can't get over it....all the boys are going to be all over you tonight...."
"You really think I look....pretty....like a girl Sis?"
"Oh you are just like Cinderella....all you need now is a pair of glass slippers...."
"Wow.....I can't believe it...."
"And the best part Baby Bro is you're not going to change back at midnight.....do you have that pack of condoms I gave you?"
"Yes but I'm sure I won't need them....."
"Just looking at what a knockout you are, I'm pretty sure you will...."
"Oh Sis....you're making me blush...."
"Wait until tomorrow when you're telling me all the sexy details....save your blushes for then!!!!"












In A Nutshell

 If there was ever a picture that told the story of our relationship this is the one!!!
She sits aloof and I kneel in worship....it works for us....maybe it could work for you too!!!












Thursday, April 8, 2021

Daddy

 "I want the blue one Daddy....and I want to get the other one for you...."
"Thank you Honey....but men don't wear bras...."
"Most men don't but I know you do Daddy....and you look so pretty when you do..."













I'm Sorry

I missed my morning post and I apologize to all of you....I woke up feeling truly miserable and I literally could not get out of bed....my wife threatened me with holy hell if I even tried!!!
Feeling a bit better now so I'm resuming posting....
Again sorry if I disappointed you.
Kisses
Kaaren

 

Wednesday, April 7, 2021

Cuckold

 It's alright....she's just fucking him....but the truth is, she's making love with you!!!