A Long Time

 "You were in there a long time...is everything all right?"

"I just needed to take something to settle my stomach....now I feel much better!!!"

"Did you take Milk of Magnesia?"

"Magnesia? No....I think his name was Steve...."

A New Feature

That chastity cage, I got for Christmas, had a new feature and she wasn't shy about using it!!!

Horrible

This is horrible!!!

I mean really horrible!!!

Once you see it how could you ever forget it???

I mean....where would you even get carpeting like that???

Can I

"Can I just see it....please....I just want to see it....that's all...."

"I guess that would be alright....just seeing it I mean....it's really one of my prettiest...."

"Oh Sweetheart....it's really pretty....can I maybe....just touch it....I just want to feel how soft it is...."

"You just want to feel my boobs....and you know I'm not that kind of girl!!!!"

"I know....but it looks so soft.....I'll just feel it for a second....you can hold my hand while I do it,,,,please...."

"Alright....I guess you guys don't get to feel silky underwear like us girls do.....alright you can feel it for a second....."

 

"There are you satisfied?"

"I guess....I don't suppose you'd let me try it on?"

"Try it on!!!! Todd you want to wear my bra???"

"I'll bring it back in a couple of days.....washed and dried...."

"The hell with that.....I want to see you wearing it....and did I tell you I'm wearing the matching panties? We're going to have us a sissy party!!!!"

Sissy or Not

Sissy or not....it's still called manspreading....but it's a little more attractive this way!!!!

Caption

I generally don't post captioned images because they're someone elses work...but I'll make an exception for this one because I can close my eyes and actually hear his voice!!!

And it's funny....thanks to whoever was the original captioner....captioneer....whatever...

Even Santa

 I mean...so what....so what if Santa wants me to put my hair in pigtails....

So what if he wants to call me a naughty little girl....

So what if he knows I'm not really a girl....

So what if he likes to get to my house early so I can suck his cock....

So what....even Santa is allowed to have a special preference!!!

Merry Christmas!!!

Oh Cum All Ye Faithful

All the guys in the neighborhood were there....after all no one wanted to miss Sissy Kaaren's Xmas Party!!!

I Saw Mommy

I saw Mommy kissing Santa Claus....well it was more like I saw Mommy sucking Santa Claus....and I rushed over to join in....I figured this was going to move me up to the top of either his naughty or nice list....it's nice to be the naughtiest and it's naughty to be the nicest!!!

Christmas Backlog

Santa was having a supply chain problem!!!!

He had to put all of his senior elves on the dildo line....and he was still falling behind trying to keep up with the demand.....

One more lockdown and he wouldn't be able to keep up at all!!!!

Yeah We All Have Fetishes

"What are you wearing?"

"Silky lingerie...with lots of lace....what are you wearing?"

"I'm kind of embarrassed to say...."

"Oh....interesting....I bet you like to play dress-up?"

"Ever since I was a boy!!!"

Wrong

"Stop Sis....this is so wrong!!!"

"What's so wrong?"

"It's incest!!! I can't have sex with my sister!!!"

"Unless you cum it isn't really sex....so it's all on you Bro...."

"Oh god!!!"

 

 

Christmas Party

He skipped dinner with his in-laws because he had promised to go to a Christmas party with the guys.....but he had to stop on the way....to change!!!

Great Act

It was possibly the greatest ventriloquist act anyone had ever seen....but it was a flop....because nobody wanted to hear what an asshole had to say!!!

Loading Dock

"You know what Bob....I was skeptical about it when you showed up at the loading dock today...in that skirt...and I'm pretty sure that those shoes aren't up to safety the latest safety regulations....I was pretty sure there was going to be a problem....but I gotta tell you....most of the guys agreed that you've got the legs for it!!!!"

Almost Done

"Are you almost done? All of the other sissy bitches are busy!!!!"

"Yeah....you can have him in a couple of minutes....I'm going to find a real man to fuck me!!!"

"Good luck with that....you wait on a line and by the time you get to the front they're done..."

"Oh well....if worst comes to worst I'll come back here and use this sissy....he's pretty good!!!"

 

 

Rare

I found it after years of searching!!!

I was told it didn't exist but I never gave up!!!

But here it is....

The beginning!!!!

The first ever internet porn!!!

Dressed Like That

"Oh my god,Sissy....where do you think you're going dressed like that!!!"

"I was just going out to meet the guys...."

"With a skirt that short everyone can see your panties!!!"

"I know but...."

"No buts about it get over here and get those panties down!!!"

"Yes Ma'am!!!"

"Alright....now you can go....remember a good girl doesn't let the boys see her panties!!!"

"Yes Ma'am....thank you Ma'am...."

Guilt

"I understand you want to make a report about sexual molestation....would you prefer to talk to a female detective?"

"No....that's not important....I'd just like to get this out into the open...."

"And this report concerns you and...."

"My uncle.....not by blood....he's my mother's brother-in-law...."

"I see....and what was the nature of this molestation?"

"It....it involved blackmail and forced oral sex...."

"I see....and did he at any point rape you?"

"Rape me? Never....I wouldn't allow that....are you crazy?"

"Wouldn't allow it....now I'm confused...perhaps if you walked me through it...."

"Alright.....I came home one day and found him sniffing my panties....and I took a picture of him with my phone.....he said he'd do anything if I would delete that pic....so I made him lick my pussy until I came all over his face...."

"I see....so you're the blackmailer.....and you forced yourself on him....so what you're doing is confessing..."

"That's right....I confess....he's waiting for me outside and I'm sure he'll tell you the same story..."

"He's waiting for you outside?"

"Well yeah....he drove me here...."

"How old were you when this happened?"

"I'm eighteen....it just happened the day before yesterday...."

"Is he prepared to press charges against you in this matter?"

"Oh no....he kind of enjoyed the whole thing....in fact he wants to so it again...."

"I suggest that you let him do just that....my hands are tied here....there's nothing I can do for you...."

"Hands are tied....that gives me a great idea....alright Detective....thanks for your time...."

Twister

 Right hand red....

Left foot green....

That;s how it always starts....

But it always ends with my tongue in pink!!!

You Never Know

I love old bookstores....you never know what you'll find waiting for you there!!!

Sadly Mistaken

"Honestly Madame if you think this display will change my mind you are sadly mistaken...I'm wearing the exact same thing under my uniform so I can see it any time I like!!!"

Wake-Up Call

This hotel offered the best wake-up call ever!!!!

Out of the Mist

She appeared suddenly....like an apparition coming out from the mist...

She walked toward me and all I could see were those eyes...those deep penetrating eyes...

But then my mind wandered a bit and I lost my train of thought....

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Pussy

"If you let me dress you in something pretty and put you in handcuffs, I'll let you eat my pussy...."

"Okay....I'd like that...."

"My don't you look pretty like that....well I'll keep my end of the deal too..."

"Hey who's that?"

"That's my Pussy....now Bon Appetit!!!"

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Heels

"Poor Sissy....you're feet must be so tired after being in those heels all day...."

"Yes....they're a little sore too...."

"Poor Baby....why don't you slip off your panties and have a seat here by me...."

"I don't think I...."

"It wasn't a request Sissy!"

"Yes Ma'am...."

Sorry Marge

"Sorry Marge...I can't....my husband just changed out of his work clothes and we have plans for tonight!!!

Client

"Hey lady...what kind of lawyer are you...you told me you needed to see your client!!!"

"Yes...I did need to see my client...but I never said anything about being a lawyer!!!"

We Just Knew It

Every guy in my high school....and for the sake of argument I include myself in that number....we all believed....without a doubt....that this was what went on in the girls showers after gym!!!

Meanwhile at Hogwarts

Hermione knew that Harry could speak to snakes....and now she was pretty clear on what he had told them to do!!!!

I Warned You

"I warned you not to get any of that hot sauce on your fingers!!!"

Cat In The Hat

Just look at it said the Cat in the Hat

The orgy was quite a success

But  despite all of that said the talkative Cat

Your house is a terrible mess!!!

Bras on the chandelier 

And sperm on the floor 

And some unknown smear

On the chair by the door!!!

You'll never get done

With all this cleaning to do

So to help I'll send Slut 1

And her partner Slut 2!!!

They'll make it all shiny and new

And then when they're done

That's when you can screw

Slut number 2 and Slut number 1!!!!

Examination

"Yes Ma'am....I'm here to examine you...."

"Is this really necessary?"

"I'm afraid so Ma'am...."

"Are you sure you need to do that?"

"Absolutely....it's the reason I'm here!!!"

"You don't really work here, do you?"

"No....not really....would you like me to stop?"

"Not at all....please continue!!!"

Guests

We had guests for the Thanksgiving weekend....old friends who know nothing about our lifestyle....they've never met Kaaren....

I had to pretend to be one of the guys....couldn't dress in my pretty things....no bra allowed because it would probably show or be accidentally discovered....

I was OK on Thanksgiving....I had so much to do with the set up and the meal and cleaning up after....

By Friday I was getting a little anxious....

By Saturday it was getting to me.....I snuck a pair of panties into the bathroom like I was a teenager, and if it wasn't for the cage I would have spent the whole afternoon filling them with sissy cream.....

By the time they left on Sunday evening.....well....

Move It

It's not enough to just wear pretty things Sissy....men see pretty girls all the time....you've got to move that ass to make them look at you!!!

Deep

"Open your mouth again Sissy....I think I saw daylight!!!"

Ready....

Target locked in....

Tracking radar ready....

Rubber seals intact....

Countdown....

3...2...1...

Launch!!!!

New Car Scent

Do you love that "new car scent"....it only lasts a little while and then it's gone forever...

The scent in my car is far nicer and is renewable for the life of the vehicle!!!

Different

"I was thinking we could try something a little different tonight..."

"Bondage? Really? Do you think it's appropriate for a Pastor to  tie up his wife and  and have sex with her?"

"Well....probably not....that's why I was planning on tying you up and fucking you with my favorite dildo and then you can eat my pussy and give me lots of tremendous orgasms..."

"Well....what the congregation doesn't know won't hurt me...."

The SBI

"We're with the Sissy Bureau of Investigation and we've received a tip that you may have found a way to remove your chastity device....so please pick up your skirt and lower your panties then put your hands behind your back!!!!"

Poker Night

I checked my cards....

"I've got nothing...."

She smiled...

"That's what the other girls have told me....but I want to see it for myself!!!"

Now You Know

 Sure it takes a while for a sissy to put on makeup in the bathroom....we had to learn it later than real girls after all....

But really....did you really think that it was just makeup that took us THAT long?

Cuckold

"Sure she made me a cuckold on our wedding night....she spent half the night fucking my best man...."

"But I got even.....while the two of them were doing it for the fourth or fifth time....I ate the last piece of the wedding cake!!!"

"That'll show her!!!"

Hurry Up

"Hurry up Batman, I don't have all day!!!"

"Do I really have to wear them...."

"Yes you do....I think they'll look very cute on you!!!"

"But what if someone sees them?"

"Under your costume? Who's going to see them?"

"Maybe...maybe Superman...you know he's got x-ray vision...."

"And you think Superman is looking at you through your clothes?"

"Well no....but he could if he wanted to...."

"What makes you so sure that I don't have Superman wearing my panties already?"

"But....wait what...."

Found

"I found these panties hidden in a box....behind your toolbox....out in the garage...do you want to tell me something?"

"I've never seen those in my life!!!"

"So they're not yours then....you don't slip into pretty little sissy panties when I'm out of the house?"

"Of course not....what gives you that idea!!!"

"Well then I guess you won't want all of these that I was going to give you to wear for me...."

"Wait....let's not be so hasty...."

Prepared

GI Joe had faced enemies all over the globe....

The forces of the evil organization COBRA....

The Nazis during WW II....

The Japanese, North Koreans North Vietnamese....

And he'd always came out on top!!!

But then he faced his ultimate nemesis....he'd been forced to submit....he'd been completely humiliated...

He was no match for.....Barbie!!!!