Thursday, October 31, 2013

Young Billy Wasn't Happy About This Hallowen Costume

Young Billy let his Auntie know that he really didn't want to wear this costume for Trick or Treating. He was even more unhappy when Auntie explained that this was not a costume it was what he'd be wearing to his cousin Ellen's Birthday party!!!

Happy Halloween Sweet Readers

Happy Halloween To all My Sweet Readers, I love you all!

How Devilish!

What better day than Halloween for that devilish Sissy to drop to her knees and worship her dark master!

Just For Halloween

I got you this special Halloween cage for you to wear when my girlfriends come over for our party tonight, isn't it wonderful Sissy?

Wednesday, October 30, 2013

Honey I didn't expect

Honey I didn't expect you home so soon...I can explain everything!!!! Where did you get those reins and that saddle?

He Just Didn't Believe

He just didn't believe what his friend was telling him, there was no way she could be anything less than 100% woman! He watched her as the night wore on and after he'd had perhaps one or two drinks too many he had to see for himself.
Gathering his courage he took his chance to get a look for himself. There was definitely more in those sexy panties than he'd expected to see, but for some reason the more he looked the better he liked what he saw!!!

So It Begins

She had him practically in tears, she brought him so close, over and over, but she always stopped leaving him gasping and moaning.
She took him in her hand again and this time she whispered in his ear, "Put on my panties and I'll let you cum."
In that moment, as he furiously nodded his head, his world changed forever!

Tuesday, October 29, 2013

After A Hard Day

After a hard day she liked to rest in the hot tub before dinner and soak her tensions away. I brought her a glass of her favorite wine.When I asked if she needed anything else she nodded and I knelt and lovingly rubbed her feet as she sighed.
I told her I had to get back to the kitchen and finish dinner and she laughed.
"You can finish me later Sissy!"

She Saw It In His Eyes

She was modeling some beautiful new clothes, she wasn't looking for a new Sissy to serve her.
He was a photographer and he was handling everything very professionally until she came into frame!
She knew at a glance that he was her new Sissy!
He knew at a glance that she was his world!

It's For Your Own Good Clark

You may have saved the world over and over but as a lover you're a pathetic loser Clark! What would Lois think if she could see you now? My spare uniform looks so nice on you and those pantyhose really suit you! And that tiny little Kryptonian clit barely makes a bump. Feel the power of my Amazon Strap-on in your sissy pussy and remember who penetrated the  the "Man of Steel!"  Learn to embrace the inner Sissy you are Clark, it's for your own good!

Monday, October 28, 2013

Truth In Advertising

Sometimes you can believe what you read!

Monday ManCandy

Mmmm, good to the last drop and with a tongue like that she's sure to coax out that last drop.
Happy Monday!!!

If I Wish Really Hard

Maybe if I wish really hard...,

Wish really really hard....

My wish may come true...

Who Says

Who says exercise isn't fun. Come for a sissy bike ride with me and we'll see who has fun!!!!!

Sunday, October 27, 2013


Bob's tailgating at the big games had become way more popular since his wife had feminized him. Bob was just one of the guys but Bobbi was hot!
The shorter her skirt the more new friends Bobbi made
Her skill at the grill had all the other fans coming over to join her and she showed more than a few that she was very good at handling all kinds of meat.

Sunday Is Game Day

It's Game Day Sissy! Better warm up and get ready looks like a tough one today!

As She Kissed Him

As she kissed her lover goodbye I discovered that perhaps he still had a reason to stay a little longer!!!

I Love Times Like This

I love times like this, just the two of us....put on something pretty for me she I slip into my sexy dress I realize how much I've changed. Where once I would have wanted to get into her panties at a time like this now I just want her to caress me and kiss me and hold me close...

Saturday, October 26, 2013

As Leeanne Always Asks - Which one's the Sissy

The adorable Leeanne plays her delightful game asking which one's the sissy so here's my Oktoberfest challenge.
Which one's the Sissy?

Just Us Again

I guess it's just us again Teddy, thank goodness I have you. You're my oldest friend and you never complain no matter what I ask you to do!

Kiss Me Goodnight

Kiss me goodnight Kaaren, we won't be needing you for a while. You can "clean up" in the morning sweetheart.

On My Way Home

I'm on my way home Sissy and I'm bringing a new friend. Put on something pretty and turn down the bed. He's getting his car now and we should be there in about a half hour.

Friday, October 25, 2013

Sissy in October - Fallen Leaves

Ah October, the glorious colors of the leaves, I love the crackling sound they make when you kneel down on them!

We're Doing Our Part

We're doing our part Kaaren, we're going green!!!

Special Delivery

I have a special delivery for Sissy Kaaren, I'm required to get oral verification of delivery!

Thursday, October 24, 2013

A Short Walk

Just to the end of the block and back Kaaren, I just want to see how well you manage in those heels.
Don't be silly Sissy, who's going to see you? I mean it's mid afternoon, who's around at this time of day anyway?

A Sissy Fulfilled

A Sissy fulfilled or a Sissy fully filled - either way sounds right in this case...

Twenty Seconds Sissy

Twenty seconds Sissy then it's back in the cage....

Wednesday, October 23, 2013

Sissy in October - I'm Certainly Not

I'm certainly not much of a boy anymore but I do still love to jump into the piles of fallen leaves!

He Couldn't Understand

He couldn't understand why she kept doing this. He was so close again and again she stopped and made him make another promise. He'd already promised to be her sissy slave, he promised to wear her panties, he promised to suck her boyfriends cock, he promised to worship her pussy, he promised to worship her ass, he promised he would do whatever she wanted if she would only let him cum!!!
She asked him if he promised to be put in chastity for her and he paused until she stroked him to the edge again and he promised.
She knew he was hers, and she would let him cum...eventually...


Subtlety has never been my strong point....

Tuesday, October 22, 2013

Give Me A Kiss Sissy

Give me a kiss Sissy, you'll be sleeping in the guest room tonight. You can serve us breakfast for two at my usual time OK sweetie!


Sometimes a Sissy has to help his mistress with her makeup. Sometimes that involves holding her mirror or getting her brush or lipstick. Sometimes it means something much more basic...

There's Nothing Like

For a sissy there's nothing like coming home after a long day and slipping into a wonderfully snug bra! It feels as nice as a hug!

Monday, October 21, 2013

Coming Home Early

I had finished all my errands much earlier than I expected and when I got home I was happy to see that my wife had also come home early. I came in and not finding her in the living room or kitchen I figured she must be upstairs. When I opened the bedroom door I was shocked to find my beautiful wife tied spread-eagle to our bed. Her eyes widened when she saw me as I rushed to her side to rescue her.
"You're early," she whispered at me, "go away for an hour or two...hurry!"
I heard the toilet flush and realized I wasn't needed.

Monday ManCandy

Better than a protein bar, a fast dose of high protein first thing in the morning to beat those Monday blues. A perfect way to start your week!

Sissy Therapy

I once thought that Therapy would help straighten me out and make me a manly man! My therapist of course knew differently right away.
After all what kind of therapist asks if you'd like to wear stockings just like hers?

Did You Ever Wonder

Did you ever wonder why Mom and Dad let you spend so many weekends at your Grandma's house?
And what was in that locked box in their closet?
And what were those marks on Dad's wrists?

Sunday, October 20, 2013

Sunday Is Game Day - For Her Too

You take care of the other men Sissy but Joey and I will be spending some time watching the game privately. I'll call you when we take a timeout so you can freshen me up!!!

Sunday is Game Day Sissy

I think you look very cute in those white panties and I'm sure that the men from the pub will agree!


Don't be silly Sissy, you look adorable and even if anyone suspected anything they'll soon be too drunk to care!

The Groom Found His Wedding Night Very Educational

For instance he finally learned why hotel rooms had two double beds...

Kaaren I Appreciate Your Enthusiasm

That feels lovely Kaaren and I really do appreciate your enthusiasm but honestly I was only looking for my contact lens!

Saturday, October 19, 2013

Sometimes You just Need A Break

After toiling away all day on the old Sissy Blog I like to push back from the desk and put my feet up and relax!

In No Time At All

Honestly he was only in the cage for two weeks and there he was on his knees! In frilly panties! Licking my boyfriends hot cum from my pussy! It was so easy, once you control his little dick you control everything! You have to try it!!!

Young Billy - Something for School

After the last shopping trip young Billy was very unhappy to find out Auntie was taking him shopping for school clothes! His cousin Ellen had some definite ideas about what he would look cute in!

A Message From Google+

Got this just before they deleted the content from my profile page:

Dear Sissy Kaaren,
You've recently been violating the Google+ User Content and Conduct policies.
Pornography or sexually explicit content are not allowed in your profile, posts, comments, photos, or anywhere else on Google+.
Please review our policies to avoid violating them in the future.
If you continue to violate our policies, you may lose the ability to use some or all features of Google+ and other Google services. Learn more
We're all in this together. Let's make Google+ a place where we all want to hang out.
The Google+ team.

Friday Is Date Night

I was in the bathroom getting ready when I heard them come in....I was still working on my makeup when she joined me.
"Oh Kaaren," she said as she stroked and carressed me, "He's so nice and he's got a nice big cock. Hurry Sissy and you can help me suck it!"

He actually smiled and said hello to me when I entered the room where she was already licking his lovely big cock. Sometimes I still get embarrassed around men in situations like this and I felt myself blushing as I knelt down and joined my wife licking him!

He pulled her up to kiss her and I wasted no time taking his beautiful cock into my mouth, I was pleased to hear him gasp as Ihe felt my lips and tongue work on him...

But what he really wanted was to fuck my sweet wife and I watched as he sank inch after thick inch into her,...

I stood by watching him take her as I never could he seemed like he could go forever....

Finally he gasped that he was going to cum, she pulled me into place under her as he sprayed his wonderful thick cum all over her, pouring it down to my waiting mouth...

Then I crawled to her and gave her another orgasm in the best way I can...

When we turned back her date had slipped away while we were busy...she smiled and pulled my face back to her hot wetness and said "One more for a nightcap Sissy!"