Breaking The Date

“I’m afraid it will be several more hours sweetie. There is just so much left to do on this project. And we must complete it before the end of the year.  I know. It means I’ll miss our special New Year’s Eve. But I promise to make it up to you.”

The Sissy Olympics

One of the most popular events in the Sissy Olympics held annually at The Vera Wang Institute for Male Modification, a/k/a “Sissy School,” was the Suck Off.  What set this event apart from many other events in the Sissy Olympics was that there were no points scored for technique.  It was a pure speed competition - which sissy could bring her man off the quickest.  Of course, there could be point deductions for “spillage,” so there was a premium upon swallowing everything.  This year Sissy Kaaren was determined to defeat her roommate and bestus bestie, Leeanne.  But it wasn't going to be easy.  Leeanne would surely receive no point deductions for spillage, so Kaaren had better be fast.

Where The Heck Is Sissy? She Needs To Get In Position!

Sissy Inspection

Get It Good And Wet Sissy

You know where it's going.

Sissy's Favorite Moment

This is the moment every sissy loves.  The moment when her wife’s stud pulls out and reveals the sweet surprise waiting for sissy to clean out.

Date Night

How sissy’s wife left her when she went on her date tonight. Sissy has some idea of what is in store for her when her wife and date return home.

Merry Christmas To All Of My Lovely Sissy Friends (And My Other Sweet Friends Too)

Come on in and join me by the fire.  Let's cuddle.

Addicked

Sissy Leeanne has become addicted to black cock.  What is she thinking right this moment? Besides how good the cock fucking her sissy cunt feels inside of her? That her mouth was occupied by another equally big black cock.

A Content Sissy

Naughty Sissy? Or Very, Very Nice?

Leeanne had been especially naughty this year.  The funny thing was, Santa couldn’t tell whether his spanking was having the effect he’d intended upon the little sissy minx.  I mean, what was that bulge Santa felt pressing into his lap anyway?

Getting Good Grades Had Its Rewards

Leeanne was giving the new sissies their first demonstration in Cocksucking 101 at The Vera Wang Institute for Male Modification, a/k/a “Sissy School.”  She’d gotten the highest grade in the class her first semester and so she’d earned the honor of providing all hands on demonstrations for the next year’s class of sissies.

Role Defined

That cock was all of the way inside of her just a moment before.  Her sissy husband is officially relegated to clean up duty.

Fluffing For Sissy

Suck it sissy.  Get it nice and wet.  It won’t hurt so much when I fuck your tight sissy cunt that way.

Ass Eating 101

A very popular class at The Vera Wang Institute for Male Modification, a/k/a “Sissy School,” Ass Eating requires each sissy to select a lab partner to help each other practice the art before returning to serve their wives and their boyfriends.

Yes! Use Sissy's Mouth To Its Best Purposes.

The Sissy Caddy Project

The pilot project at Pebble Beach soon swept the nation and there was a huge resurgence in the popularity of golf.  It wasn’t long before every golf course began hiring and training sissies to serve as caddies at their clubs.

Strappin' On To Take Care Of Her Sissy

Being Unprepared

Sissy was where she was supposed to be.  However, she had not calculated on early withdrawal.

Sissies Preparing Mistress' Ballroom For The Annual Christmas Party

Mistress Presents Herself For Worship By Her Sissy Husband

Where A Good Sissy Does Her Best Work....

Hippity Hop, Sissipity Hop

What Are You Waiting For Sissy? Time To Get Busy Sweetie.

Feeding Sissy

Sissy’s wife told her boyfriend sissy wanted all of him. So he gave it to her.

Sissy Fashion Show

An Open Invitation From Sissy Leeanne

Some could say this is such a waste.  Others would simply marvel that Sissy Leeanne was able to hold so much thick cum in her mouth.  What would make this better?  How about a sweet friend to kiss and share this yummy load with.  Any takers?

Sissy's Wedding Day Turned Out More Special Than She'd Dreamed

Sissy Is Feeling The Holiday Spirit

Sissy's First Double Date With Her Wife and Two Guys From Her Work Was Turning Out Better Than Either Of Them Had Hoped

Sissy's Favorite Feast

Cummy Kisses Are The Bestest

Eany Meany Miney Moe

Getting Psyched!

Pre-party huddling of the sissies hired to serve (in more ways than drinks and hors-d'oeuvres) the guests.

It's Certainly Not Like Hand-To-Hand Combat

The sissies wives seemed to always come up with new ways to ensure that their sweet sissy husbands behaved when they went on their dates.  Not that these two sissies seem to mind their plight.

New Girl Initiation

No one recalls when the practice began.  Some claim it was when those two sissies, Leeanne and Kaaren, were terrorizing the dormitory halls at the Vera Wang Institute of Male Modification, a/k/a "Sissy School."  But this new sissy was roused out of her bed in the middle of the night, collared and leashed, and now she's being led to the rooftop where all of the second and third year sissies are waiting to give her a student run welcoming party.  They say no new girl is ever the same after her first time in the middle of the circle.  And the teachers don't say anything, because the new girls are almost always immediately more compliant in class after the event, even if a little hazing occurs.

Sissy Surprise

Sissy’s wife told her she had a surprise for her.  And boy did she!  Shhhh.  She didn’t tell her sissy the two guys she brought over were the other two guys on sissy’s sales team at work.  They were very impressed with how sissy closed the deal.

My Thanksgiving Day Preferences

Some people just want the leg.  Others only want the breast.  But me, I want some of each, and this photo illustrates why deliciously.

Happy Thanksgiving Everyone!

I'll be slaving away in the kitchen all day!  Yum!

Which One Is The Sissy?

Sissy Has A New Job As A Dog Walker

She's developing a client base quite rapidly thanks to her wife's insistence on selecting her wardrobe.

New Apple Computers

The mousepads are so sensitive, you can navigate with your nipples.  It is a huge advancement in Tumblr surfing technology.

Let The Poor Girl Get On With Her Hoovering*

A well-trained sissy maid is taught that she must always be available to her wife’s lovers, no matter what other menial chore she is engaged in at the time the urge strikes him.  It’s one of the very reasons she’s required to dress as she does.  And as for her hoovering, she’ll be hoovering alright soon enough.  Only it won’t be with the vacuum.

* Hoovering - A British term used for vacuuming.

Such A Tease

Sissy Likes

Sidetracked

Sissy was supposed to be making her wife’s bed.

Sissy Was Torn

On the one hand, she was  up early preparing a special breakfast for her wife and her boyfriend.  On the other hand....

The Beginning

She’d made him promise.  If she let him cum in her mouth, he’d let her do this.  And then, he had to wear her panties.  Soon, he’d be her sissy maid and sucking cock for her.