Lunch Date

Oh Sissy, I didn't expect you to be early....yes we're still going to lunch...I'll be ready to leave as soon as this intern makes me cum again...don't pout Sissy...you can have your turn when we get back from the restaurant!

 

Sissy What's Taking So Long!

"Sissy, what's taking so long? I need a big cock inside me now!"
"Just another minute or two sweetheart!"
I knew he was ready but he had a wonderful cock and I just wanted a little more of it before she had her fun! Hopefully I'd get him again at clean up time!!!

The Third Date

"Yes it was a lovely restaurant and I really enjoyed the show! But I've been wondering about a couple of things...I see you have quite a lot of cosmetics in your bathroom and I can't help but notice you seem to keep staring at my feet! Is there anything I should know?"
Time to start telling her everything Sissy! Worst case, she calls you a couple of names and you never see her again!
Best case, you're fully made up wearing your prettiest panties and licking those beautiful toes!
Always hope for the best! Honesty is the best policy!

 

Maybe Sissy

Maybe I should have been born with a cock Sissy...a great big thick meaty cock! You'd feel it rubbing against your sweet girls ass when we're like this!

You'd push back against me like you're doing now! My cock would be pressing against you! It would be all that you could think of! You'd feel it pressing against your sweet sissy pussy! You'd want it wouldn't you? I feel you squirming under me! You want me inside you! You want me to fuck you! To fuck that sissy pussy all night long!
Wait just a moment Sissy and I'll make your dreams come true!

Sissy School - Auto Shop

"Alright Sissy Kaaren let's see if you've done your homework for once! Imagine, your car simply won't start, after you open the hood what is the very next thing you do?"
"I bend over at the waist and flash my panties and I should have help arriving in no time at all?"
"Absolutely correct, I see you've done your reading, very good Kaaren!"
Sissy Kaaren leaned over to her friend Sissy Leeanne and whispered, "What's he talking about? Was there something I was supposed to read?"
Sissy Leeanne disguised her laughter as coughing and excused herself to go to the Sissy's rest room!

 

Monday ManCandy

Hot White Cum....Pearly White Teeth....Coincidence? I don't think so!
ManCandy is there anything it can't do?!?!?!?! The perfect start on a Monday morning!

Treasures of Grandmas Dresser

I wonder if she knew that I was the only one of her grandchildren who would appreciate it the most! People always said I got my looks from her...that I had her eyes....now here...like this...I see the resemblance!!! And I love her and miss her even more!!!!

 

Waiting

One of the hardest things for a Sissy cuckold to do is wait to be called while listening to their moans of pleasure coming from the Mistress Bedroom!

Vintage Sissy

As he pushed the hidden door open Detective Smythe could not believe his eyes!
"Oh my God, Caruthers! Is that you!?!?"
"Run sir, these fiends have a machine that turns men into women! Run sir it's too late for me...save yourself!"
Detective Smythe stepped into the hidden laboratory.
"Turns men into women you say!" he said removing his shirt and extending his hands to be bound, "I' think I'd like to see if they dare try that on me!"

A Good Sissy

A good Sissy is always prepared, ready at the right moment to serve! Her date has barely had a moment to catch his breath as Sissy rushes in to clean up!

Let's Go For A Walk

Let's go for a walk Sissy! The boys in the Fraternity down the street have "rented" you for tonight. I told you we had to cover all your expenses somehow, and their offer will pay off your Victorias Secret account in full!!!

Sissy's Big Night

This is it Sissy...after tonight you're no longer a virgin!

 

Serving My Country

"Hello"
"Yes Senator I'm almost there, just a few more minutes..."
"Yes I'm wearing that dress..."
"Sorry but she said no, so it's still locked in it's cage..."
"No Senator, using a locksmith would be cheating..."
"No I forgot my bag in the car, why don't you just keep your dress in your office..."
"I'm sorry but my car is hundreds of miles away at a train station Senator, if I go back to get it then we'll have to reschedule..."
"Of course I'll let you wear my panties while I suck your cock..."
"I would like to discuss your position on a few issues before I let you cum in my mouth..."
"Flexible...Me Too!"
"I'll be right there baby....I have a few congressmen to see later!"
"Be there in a minute baby..."
"Bye"

 

I Know It's Going To Hurt

I know it's going to hurt like hell when she takes those clips off and my skin will be a little raw from her beautiful nails....but.....heaven help me I just love when she does this!!!!

Young Billy Was Not Happy

It was bad enough that Auntie had signed him up to be a cheerleader instead of a player, but when the girls on the squad made him up and gave him the long blonde wig it was just too much! When they made their way down the hall clapping and cheering he was amazed that no one seemed to notice him!
That is until he heard a girl shriek, "Billy is that you in that skirt!?"
He whipped his head around in time to see his cousin laughing...moments later all the students in the hall were pointing and laughing as he blushed crimson with embarrassment Thank god the panties were holding down his stiff little dick or they would all know the truth about how much he secretly loved this!

What Do You Think

What do you think of this lipstick Sissy? Oh I forgot you can't say right now...that's alright you just keep doing what you're doing Sissy!

Lunch Date

It's always special when she invites me to her office to join her for lunch!

I Have To Go Out For A While

I have yo go out for a while Sissy, I'll probably be a couple of hours. Now stop that pouting Sissy! Here let me give you some help keeping me in your thoughts till I get back! Breathe in deep Sissy, I want my scent to be all you think of till I get back! When I get back you can show me how much you appreciate my gift!

Memories

You see Kaaren, that's when we had that sweet Leon over...remember that cock....I swear I thought he was going to choke you to death with it! But you loved it as much as me I think! Remember how he sprayed his hot cum on both of us? Yeah it was wonderful! I'm getting a little wet just looking at you with that monster in your sweet mouth!!!

 

Monday ManCandy

I know you're grateful for the energy boosting, fresh dose of creamy ManCandy but please wait until it's all warm in your tummy before you say "Thank you"! Didn't your Mom teach you not to talk with your mouth full?

That Little Bitch!

That little bitch! I told her how important this dinner was! She did prepare a wonderful meal and she did serve my guests flawlessly and she does look absolutely adorable in her sissy maid uniform but I can't possibly overlook the crooked seams on her stockings! Sissy is going over my knee as soon as my guests leave!!!

Do I Need To Rermind You

Do I need to remind you again Sissy? The guests will be here soon and I will have a lovely Easter dinner on the table....on time...or you'll find out that what you just got was only a little warm up!!!

Easter

Well I'd say me too...but I pray all the time for a second cumming!!!

Sissy School - Spring Break

The judge eyed them all closely!
"You four, Sissy Jo, Sissy Kaaren, Sissy Leeanne and Sissy Shawna have been charged with a staggering amount of crimes including public lewdness, public drunkenness, indecent exposure, sodomy and...bestiality? Miss Prosecutor what about that last charge?"
"Your Honor, the second one there, Sissy Kaaren, was being sodomized by the inflatable bull mascot of one of the fraternities while she was giving oral sex to two...."
"But no real animals then Miss Prosecutor?"
"No sir no real animals."
"Okay then that charge is dismissed, and as for the rest I think I'd like to interview these....young ladies...in my chambers...court is recessed until tomorrow!"
"But your Honor it's only 10AM!"
"Recessed Miss Prosecutor! I'll see you tomorrow!"

Feel Him In You

Feel him deep inside you Sissy, Your sweet sissy pussy stretching to let him inside you! He's your man now Sissy, he's got his big cock inside you, you're his little slut now! Give him the ride of his life Sissy! Make him cum inside you! Let him make you the girl you were born to be!!! Fuck him Kaaren...look into my eyes, sweet sissy, as your lover takes you over the edge! Fuck him like the special girl you are!!!

Just My Imagination

Which one is he Kaaren?
That's Mr Schultz, he was the head of the Phys. Ed department.
What did he do Kaaren?
He insisted that I had to run a mile to get my Phys. Ed. certificate before I could graduate!
That sounds reasonable to me....
He made all the boys from the dance program run in our dance class clothes! Leotards and tights! And he invited the football team to watch!
I see, you go right ahead then Kaaren he's earned this!

Sissy School - A Womans Touch

"Well Sissy Kaaren, I see you've even managed to be late to our meeting. we are certainly not getting off to a good start! The headmaster seems to think that your interaction with the male staff has been lopsided in your favor so he thought you might need a woman's touch to correct your naughty behavior, you may refer to me as Ms. Alexis"
Sissy Kaaren sat stone faced, she wasn't impressed so far!
"Well, cat got your tongue Sissy? Perhaps you're having a hard time focusing your attention. I have just the thing for that!"
Sissy Kaaren was shocked when Ms. Alexis unbuttoned her blouse and rubbed her little nipples until they were erect. Ms. Alexis quickly grabbed two small clamps and before Kaaren even realized what was happening her nipples were cruelly pinched by them.

Sissy Kaaren gasped as the initial jolt of pain went through her!
"I have your attention now Sissy?" asked Ms. Alexis while giving the clamps a small tug.

"Yes Ms. Alexis!" Sissy Kaaren gasped, she didn't want the woman to know that she was kind of enjoying the feel of the clips, that the pain was starting to give way to arousal!
"Yes what Sissy Kaaren?
"MmmmYes Ms. Alexis you definitely have my attention."
"Hmmm, warming up are we, perhaps this will warm you further!" she said picking up her antique rug beater.

Pushing her down on the padded bench she soon had Sissy Kaaren in a perfect position and began spanking her. The Headmaster had told her that spanking was useless, that Sissy Kaaren seemed to enjoy it but she wanted to see for herself.

Sure enough, to Ms. Alexis surprise the young Sissy was moaning, but it didn't sound like she wanted it to stop any time soon! Ms. Alexis was finding the challenge this Sissy presented a little exciting!
The harder she spanked the more the squirming Sissy seemed to enjoy it! She couldn't believe her ears when she heard the Sissy encourage her to spank her harder! She had encountered some naughty sissies but never one so naughty that the punishment only made her worse!
And worse yet with every swat she looked at the pretty bottom in front of her and she found her own thoughts getting quite naughty!
Ms. Alexis couldn't wait any longer! This Sissy had her so excited she needed some attention right now! She slipped off her soaking wet panties and stepping up to Kaaren she pulled the Sissy's face into her steamy wet pussy!

Just as she had heard in rumors, the Sissy had a fantastic tongue. She came hard and quickly, as the Sissy's tongue kept working! After three more mind shattering orgasms she finally pushed her away. She tried to compose herself as the Sissy remained in position watching her, a smile on her wet lips.
Kneeling down Ms. Alexis gave her a kiss, tasting herself on the Sissy's lips and tongue!
"So are you going to behave now Sissy Kaaren or will we have to do this again?"
The Sissy laughed, it sounded so sweet. "Oh I'm pretty sure you'll probably get a call about me again! Probably soon, at least I hope so....I haven't had this much fun in weeks!"

Another Job Lost

Okay this time it really wasn't my fault! I listened very carefully and I did what I was told!
"You can't work in those clothes Kaaren" he said.
"You have to wear the uniform Kaaren" he said.
"You can wear this apron until we get a uniform for you Kaaren" he said
So let's review, I can't wear my clothes, I have to wear the uniform which I don't have, I should wear the apron until they get me a uniform!
I did exactly that and he still fired me although he did give me his phone number before I left and said I should call as he might have some work I could do at his house!

 

Do It Baby!

That's it baby....take his hard cock in your mouth...suck that cock...that's it...suck it hard...I want you to be my cocksucking sissy....use your tongue baby...make him cum..make him cum and swallow it all...be my girl...be my sissy...then you can use that cummy tongue on my clit and make me cum too....suck him...do it for me...you know you want to...you know you love it....

Come and Get it Kaaren

These are so full of his cum that they were practically sliding down my legs! When you've licked these clean I'll be waiting for you in the bedroom....hurry now Sissy I want that tongue in me soon!

Choices

"I'll tell you what Sissy, I'll give you a choice. I can release you right now but you won't touch, taste or even see my pussy for a month or you can agree to stay locked up for another month  and kneel down and lick me right now. Which will it be Sissy?"

I know exactly what I would do...what would you do? I'd love to hear from you!!!

I'm Home Sissy

For obvious reasons I hadn't heard her come home early! I first heard her call out as she pushed open the bedroom door!
"I'm home Sissy, there's a strange car in our driveway and....Kaaren!!!! What is the meaning of this?!?!?"
I was in no position to explain at the moment, as she could see!
"You finish up then you get my hairbrush and come to the den! You have some explaining to do!"

Rewards - Sissy Training

As your Sissy progresses it's always a good idea to give him a reward, but the reward must be something you choose! Sissy must learn that even his rewards should be pleasurable to you whether he likes it or not!!!

When I Was A Girl

When I was a girl I used to ask my Mom or Dad to zip me up! I never dreamed that one day I'd have a Sissy husband who'd be asking me to zip up his dress!!! I never dreamed it but I love it!!!

Monday ManCandy

What's the best way to start another work week? ManCandy gets my vote! A mouthful or more gets me out the door!!! Thumbs up!!!

 

Kaaren Get Him What He Wants

"Kaaren!" my wife called from her bedroom, "please take Mark to the kitchen and make sure he gets what he wants!"
As I stepped out of my Sissy bedroom he was waiting in the hall wearing his black boxer briefs and his boots! It was funny but I guess he had no slippers....He smiled at me and motioned for me to lead the way.
Have you ever felt someones eyes on you? Maybe it was because I felt him checking me out or maybe my natural inner slut was coming out but I walked a little slower and added a little bit more hip motion!
When we reached the kitchen I asked him what he would like to have.
"Only one thing I want right now!" he laughed.
I found myself, panties pushed aside and bent over the counter before I could even say anything! I only managed to gasp that I needed to be lubed! He used his spit!!!

As he entered me, filling me up with his wonderful cock, I heard her call downstairs.
"Did you find anything? Sissy you make sure you take good care of him!"
He gruffly answered "Yes I'm enjoying it right now! Your Sissy is wonderful in the kitchen!"
I couldn't answer, I was lost feeling that cock fucking me, it turned out we both got what we wanted in the kitchen!!!

A Sissy Must

A Sissy must always be ready to provide that small boost her wife needs to reach the object of her desire!!!

I Couldn't Agree More

Sissy you made a wonderful choice when you picked Ted for your Best Man! From what I can feel he's certainly the best "man" here! He'll be coming back to the hotel with us, won't that be wonderful.

Needs Fluffing

Isn't it nice Kaaren? I'm really going to enjoy him, but he seems a bit droopy. You get him nice and hard for me and I'll be waiting in the bedroom! Hurry Sissy I really need a man's cock tonight!!!

A Sissy Lives To Serve

I love doing this for her! While she surfs the 'net I kneel and polish her beautiful nails! After I finish her hands the polish on her toes should be dry and I can then give them some special attention!

I Heard The Door

I heard the door open and footsteps approach the bed! I strained to hear something that would help me identify him but all I heard was his soft breathing as he stood so close! My senses were straining and so was my poor little clit, locked away in it's little cage! All I knew was that he was going to take me however he wanted, she had promised him that! She also promised him I would never know who he was unless he wanted me to know!
All she said to me was, "You see him almost every day Sissy!"
He could be anyone...I tried to think and then I felt his hands on me and I forgot everything...at least for a while!!!

Feeling Foxy!

I just love this new plug with the tail attached! I would be wagging it right now but I'm busy with this nice man's cock at the moment!

Sissy School - First Time

Sissy Kaaren had met him in town and they had both felt the attraction! It was different than what she felt for girls and sissies, just being near him made her tingle in ways she never had before!
When he invited her to his house she knew that she would never make curfew but she had a feeling that the spanking she'd get for tardiness would be worth it!
In the blink of an eye he had literally charmed her out of her panties and after she demonstrated her considerable oral skills he told her he wanted her! Wanted her badly! She watched as he put a dollop of lube on his delicious cock and rubbed it back and forth until he glistened in the light! Then he laid her back and slowly, oh so slowly, pushed against her, stretching her as he  entered her!
She was grateful now for all the classes she had received on pleasing a man! There was little pain as he slipped his length inside her and as his body pressed against hers she knew that this was something she would want to do over and over!
He felt so different from the dildos and vibrators and plugs...she couldn't explain it but she was delighted and thrilled!
She would tell her best friend Leeanne all about it later but for now....Wow just wow!!!!