Long Ago

We were arguing.....over something stupid that neither of us remember.....but the thing that stands out....the thing we both remember so well is when she told me to "Kiss my ass!!!!"
And I did.....I bent down and kissed her ass......I remember she was wearing jeans and I kissed her ass.....and I enjoyed doing it so much that I kept doing it....and she enjoyed it too...
We had both discovered something about each other....

Sissy School - A Weekend Visit Home - CANCELLED

"it's sad that we can't go home Kaaren.....but you have to cheer up.... "
"Why should I.....I didn't even get a letter from home this week...."
"I know a way to cheer you up......"
"Hey.....you know.....I'm suddenly feeling much better!!!!"

Comfort

It's just the two of us so we both like to wear our "comfort" clothes....
She likes a simple denim skirt and top whereas I like a nice dress and hose....
It's funny how we both choose to wear heels to be comfy....
I almost always feel like an innocent little girl when she starts feeling me up...and this type of thing usually ends up in her bedroom.....with her big latex cock buried inside me!!!
I'm not a virgin in any sense of the word....but sometimes I still like to imagine that she's a bad girl who's going to take me for the first time.....

Quarantine

What do you miss most about being under quarantine?
Going out to your favorite restaurant....oh yeah....me too....a beautiful New York Strip steak, medium rare, with mushrooms.....oh yeah....I miss that....
Going out to the clubs and dancing the night away.....I love to dance....and I miss it very much....she laughs at me when I put on music and dance around the house....
The Theater.....I love going to shows....sure they're overpriced and the seating is wildly uncomfortable....but I love seeing a good show that's performed well....
A Bloody Mary at my favorite bar.....Johnny the bartender really knows how to make them....I'd tell you the bar's name but I'm afraid it would mean crowds and I wouldn't get my favorite stool up in the corner....
And so much more....
Shopping....
Picnics.....
Family gatherings....well....with her family.....
Grilling burgers for the kids....except little Maddy....she likes hot dogs....just like me!!!!
And you can all get your minds out of the gutter....Maddy is five and she's the closest I'll ever have to a daughter....
Going swimming with everybody.....I love to see the bulges and the boobs.....
But most of all I miss sucking a nice big cock.....
I love the feel of it in my mouth and I love to hear the moans and groans as I work on those delicious cocks.....
I'm just tired of waiting for it....

Side By Side

Is there anything better than being on your knees sucking a big cock while your sweet wife is kneeling next to you doing the same....
It becomes almost like a competition to see which of us can get a sweet mouthful of cream first!!!!
But we're not competing.....we're going to share whatever we get!!!!

Lube

"Yes Sissy....I'll use lots of lube....and I'm going to slip inside you so smoothly that all you'll feel is pleasure....."
"Mmmmm"
"And then I'll use lots more when my friend Maurice gets here...."
"Wait what????"

Old Habits

Even though I'm going to spend most of the afternoon with my tongue buried inside her glorious pussy....I still take the time to give her panties a good sniff....
It's an old habit and I have no intention of breaking it....

Almost

The wives were deep in conversation and they told us to go upstairs....
"No fooling around sissies...."
"Yes Ma'am...." we said, almost simultaneously....
And we almost made it to the top of the stairs.....almost....

Shopping

I hate this....fucking stupid virus!!!!!
I need to go shopping....
I need new shoes....
I need new dresses....
I need new undies.....
I was going through my closet and I have absolutely nothing to wear!!!!!

Hump Day

Even though you've been encouraged to work on your own.....sometimes you need some supervision to make sure you're correctly observing Hump Day!!!!

What Do You Mean

"What do you mean you don't want to go Sissy? You said you were going crazy and you needed to get out and go for a walk!!!!"
"I just don't feel like it anymore...."
"I spent an hour dressing you to get you ready....so you can bet your sweet girly ass that you're going for a walk....three times around the block should do it...."
"But what if people see me....like this...."
"Oh Sissy....do you really think....after all this time.....that everybody around here doesn't already know that you're a sissy?"
"Really....everybody?"
"Yes Sissy,,,,you're not nearly as discrete as you think.....now get going....."
"Yes Ma'am...."

Wanted It

"I've never wanted it more Sissy....I want it in my mouth....I want it in my pussy.....I want it in my ass....I want you to shoot your sissy cream all over my face....all over my tits....just all over me!!!!!"
"Wow....really.....I want all that too....so much....it's been so long.....just get the key and I'll do my best for you...."
She giggled like a schoolgirl and ran out of the room.....but when she came back she was far more serious....
"It's funny Sissy....as soon as I touched the key....I began to think of all the disappointing sex we used to have....."
"So I suppose....."
"Yes Baby.....I've changed my mind.....maybe another time...."
"Yes Ma'am.....thank you Ma'am...."

When I Was A Girl

When I was a girl my friends and I used to always try on each others clothes and we would borrow from each other too....
I never dreamed that someday I would marry a sissy who loved to wear my dresses.....and looked so good in them too!!!!
I never dreamed it but I love it!!!

Monday ManCandy

Everyone is entitled to enjoy the fruit of their labor!!!!
But if he's silly enough to walk away after filling up the cup then, of course you're entitled to drink your fill.....why let it go to waste?
Perhaps he's being generous....perhaps he's already had his fill.....whatever the reason just enjoy that he left it for you to enjoy!!!!
ManCandy!!!! My cup runneth over!!!

Sunday Brunch - CANCELLED

Sure the Sunday brunch was cancelled but we liked to reminisce about the best times....
Like there was that time that she got jealous that I was getting to suck all the cocks and before I knew it she had a nice big one in her mouth too!!!!
Oh yeah....good times!!!!!

Quarantine

Our neighbors granddaughter is staying with her during the Quarantine...it's pretty clear to me that she knows all about my status as a caged cuck.....
Every time I go out into the yard.....she pops out to chat.....and OMG....a college girl dressed like that!!!!!
She teases me for a while then she wiggles her sweet little bottom back into the house....leaving me frustrated as my little clit tries to break through it's cage....

Comfortable

"Very good Sissy....are you comfortable?"
"No.....not really...."
"You're not still trying to get hard are you Sissy?"
"Only when you inspect me Sweetheart...."

Inheritance

He had inherited everything when his wife passed away....
Her money...
Her business...
Her house....
Her wigs...
Her clothes....
Her makeup....
Her lover....and his big cock...

Closed

The deal is done....I marveled at the way she manipulated the  client.....
She put everything she had into making it happen.....
But she got it done....on her terms......
And now that the meeting was done......and the cam was off....
Now it was my turn.....it was time for her reward!!!!

Let's Go

"Let's go bitch....lets show your wife the kind of bitchboi she married...."
"Please can I at least clean myself...."
"Oh no bitch....I want her to see my cum leaking out of your ass....she's going to really learn all about you today...."
"But I...."
"You get on in there and ask her if you can borrow a pair of her panties to wear because a real man's cum is leaking out of you boi pussy...and when she finishes laughing I'm going to fuck her right in front of you....I'm going to make her cum like she never has before, on that puny little dick of yours...."
"Please I...."
"You have something to say bitch you better say it now.....cause after this the only time I want to see you open your mouth is when I want to stick my cock in it....."
"I wanted to say.....Thank you!!!!"

Marriages Everywhere During Quarantine

"Just remember Baby....at the office you may be the hot shot, up and comer.....but here you're my sissy bitch.....and I'll decide if you ever get to come again!!!!!"

Me Too

"You know this whole quarantine thing isn't so bad....my company is paying me my full salary and all I'm doing is some work on my computer...."
"Yeah that sounds pretty sweet..."
"And the best part is I've been hanging around in just a t-shirt and my boxers....."
"Yeah me too....."

Hump Day

Yes it's Hump Day again.....
It's important to remember to put your client's needs before your own....that's how you close the deal!!!!

First Taste

Weeks had turned into months and he had tried to resist....but without his usual outlets he turned to his roommates to give him what he craved.....and as he leaned forward to take his first taste he realized that after this he would never be just one of the guys ever again!!!
And that was OK with him......

After the Flu

After my bout with the flu I became even more concerned about germs in the house....so I use my disinfectant on just about everything.....
I can't figure out where I caught it and it's driving me crazy.....and I can't figure out how my wife didn't get it from me......although I am grateful she didn't.....anyway.....I don't think I've missed any spot in the house where a germ might lurk....
She laughs at me when I clean her desk.....
"Do you think I'm going to infect myself Sissy?"
Let her laugh.....I just want to be sure....

It Was Good

He leaned over her and asked her if it was good for her....
"Yes Baby....it was soooo good....but you have to move aside now.....now it's my husbands turn....he's going to lick me clean!!!!"
"Oh my god.....he's such a sissy!!!!"
"Yes he is....that's why I love him!!!!"

Joy

There is a certain joy to be had just laying in bed and feeling your smooth stockings....
You may not be able to stroke your little caged clit but you can stroke your smooth nyloned legs....
Just imagine a strong man pushing your legs apart and really making you feel like a woman....
What joy!!!!!

Monday ManCandy

It's really true that sometimes there's a bit more than you can handle all in one shot....
A few drops spilled is a shame but when you weigh that against the huge load sliding down to your tummy....well it's not so bad!!!!!
And for the really dedicated you can always get the rest.....you just have to get down and lick it up....
ManCandy!!!! Come for the bulk....stay for the scraps....

Sighs

Yes the quarantine is wearing us down.....
"God Sissy.....I love you but sometimes I wish you had a cock....I could really use a cock right now!!!!"
"Me too Sweetheart...."
"You're such a slut...."
"Yes I am Sweetheart.....I'm your personal slut...."
"That's so sweet Sissy...."

Sissy School - A Weekend Visit Home - CANCELLED

"Look Kaaren....it's obvious to all of us that you're depressed...."
"Really....I'm OK...."
"We all know how much you look forward to your visits home...."
"Well....yes I really do....."
So some of us contacted your wife and asked her to do us a favor...."
"You did!!!!"
"Yes we did....we asked her to send us something that will really remind you of home....and she was nice enough to send us this...."
"Oh my....that's my favorite....."
"She used it before she sent it so it should still have her scent on it....and maybe you'll be able to taste her too...."
"I can't thank you enough....this is wonderful!!!!"
"Why don't you give it a little suck to get it wet and then bend over and you'll feel just like you're at home!!!!"

The Virus

She had to be so careful not to let the virus spread.....she took all the necessary precautions.....
She always handled the samples with gloves....
No way was she going to allow the small dick virus to infect the population....it was bad enough that her husband had caught it....
Thankfully she had discovered that regular doses of semen from big black cocks had given her a certain amount of immunity....
She would have to do far more research into the immunity.....lots more research!!!!

Dressed

"Kaaren....you look beautiful....that's a lovely nightie...."
"I'm glad you like it.....I love your lingerie too...."
"I can't get over how pretty you look....."
"I know what would make me look even prettier....."
"Really?"
"Oh yes....I think I would look really pretty with your thighs pressed against my ears...."
"I think that would look lovely too Sissy.....let's go to bed...."

Drips

How many men could sit and watch their wife take another man's cock into their mouth?
How many men would submit to being a caged cuckold?
How many men would sit and wish that he could suck that big cock?
How many men would drip onto the pillow as they watched.....
I don't know how many.....but I'm one....

Surprise

She smiled at herself in the mirror....
Sissy was in for a surprise when he crawled up under her desk during her next online meeting....

Never Enough

It really can't ever be repeated enough....every time I got down on my knees I could hear her voice....so loud and clear....even if she wasn't there my memory would provide me with vivid recall.....
"Never forget the balls Sissy!!!!"
"Yes Ma'am!!!!"

Not What They Used To Be

Yes.....even a submissive sissy starts to feel her age as years go by....
I have spent a lot of time on my knees over the years and now I'm afraid to say that I just can't kneel for as long as I used to....
So my darling wife has agreed to let me sit outside her bedroom while her boyfriend fucks her like I never could....
She wants me to save my knees for when I clean up the two of them....
She spoils me like that....what a wonderful woman she is!!!!

It's Her Fantasy

I don't know the story behind her favorite fantasy but she indulges me in so many of mine so when she lays out my cheerleader uniform I know I will be helping her fulfill hers!!!
When she leaves out the cheerleader uniform I know she's living her fantasy and I'm ready to go along for the ride....
"That's it Donna.....put your fingers in my pussy.....make me cum on your fingers.....make me cum you bitch!!!!!"
I don't know who Donna was and I'm not going to ask....if she wants me to know she'll tell me....I mean if I get a chance to pretend to be her teenaged lesbian lover....I'm going to go for it!!!!!

Hump Day

Sometimes you don't realize it at first....but by Hump Day you can't help but see it!!!!
Your latest project has gone sideways and thankfully that made it even better!!!!!

Anything You Want

"Why sure Honey....you just feel free to try on anything you want...."
"Thank you Auntie!"
"But we'll keep this our little secret right?"
"Of course Auntie!!!!"
"That's why you're my favorite nephew!!!!"

What Did She Know

As you swallowed that big girlcock you couldn't help but wonder.....
What did your sister know when she arranged this blind date for you?
But you can't really think right now....right now you have a delicious cock in your mouth and if your sister was here you couldn't thank her enough!!!

Allowed

"Jesus Tommy....look at what she's done to you!!!!"
"What do you mean Steve?"
"What do I mean???? Just look at yourself....look at how she makes you dress!!!!"
"You're looking at it the wrong way Steve.....she doesn't make me dress like this....she allows me to dress like this and that's why I love her....."

Monday ManCandy

In these troubled times it's so nice to have neighbors who are willing to share....
You needed it and she just happened to have plenty left over from her husband....
That's so nice of her to care enough to make sure you get what you need!!!!
ManCandy!!!! Love thy neighbor aren't just words in a book!!!!!

Sunday Brunch - CANCELLED

It's so nice that they've reopened a couple of restaurants.....and you know I love this one in particular.....the wait staff always goes above and beyond.....can you believe they actually remember us....they even made sure to serve up your favorite appetizer...so get over here and dig in....."
"Thank you Ma'am!!!!"
"You know I spoil you Sissy.....just wait till you see the dessert I ordered for you!!!!

When I Said

"When I said I wanted you between my legs.....fucking me hard with that big cock....did you really think I was referring to your little caged clitty?"
"MMMMmmmppph"
"Yes Sissy I know you're eager......we're going to have such fun.....well...at least I am!!!!"

Warning

"I'm warning you Sissy.....if I get any Sissy drippies from your little clit on my stockings you'll be in even more trouble!!!!"

Key To Success

The key to success....
Dress for the job you want....not for the job you have....

Pleasure

I'm well aware of my inability to please her with my little clit.....so like a person deprived of one of their senses I've learned to compensate....
Every time she watches that video of me finally taking him all the way into my mouth she cums.....every time!!!!
I'm kind of proud of that!!!!

Greedy Cuck

He had agreed to let his best friend fuck her....she wanted a real man....not a man with a clit!!!!
He knew he was small and he knew he couldn't satisfy her....and he knew his lifelong friend could take care of her!!!!
But when the time came he just had to suck that cock himself....he'd wanted to ever since he could remember and now he was finally going to get his chance!!!!
She might have to wait a little while to feel him inside her but he had already been waiting for so many years!!!!!

 

Ready

Sissy....I'm ready to fuck your wife....come over here and undress her for me....and do it slow....."
"Yes Sir......may I Ma'am?"
"You may Sissy....."

Hump Day

One of the best things about Hump Day is....
What?
What do you mean it was yesterday?
How could I miss an entire day?
I don't believe you.....hand me my phone....
Son of a gun.....it was yesterday....
Well.....
One of the best things about Hump Day is that it really doesn't matter which day of the week it is.....who's keeping track anyway?
Let every day be Hump Day!!!!