Will It Fit?

My wife assures me that there is only one way to find out.

Sissy Call Girl

At first, when my wife feminized me, I thought I would be able to continue with my current job.  But, alas, even though no one explicitly told me I had to leave, the job requirements changed as I blossomed, so to speak.  Now, I'm expected to provide certain, ah, special services to out of town clients when they visit.  At first this was difficult for me to accept, but there are fringe benefits that make it worthwhile.  And then there are the tips I receive when I've performed especially well.

Let Me Think About It Sissy

It was the third straight month that my wife had not released me from chastity.  I had tried to do everything just the way she likes it.  Still, she was disappointed with the way I'd folded her panties the last time I did laundry.  So she was making me beg for release.

"Please sir, I want some more."

Seriously Leeanne?

"Do you actually think I would permit a sissy like you to touch this goddess body?" Miss Sharon jeered.

Sissy Appreciation Sex # 103 - For Alyssa

Alyssa is such a cute girl.  I hope she enjoys sharing a cock with me as much as I enjoy sharing it with her.

Thank you Alyssa!

Sissy At Your Service

As it should be.

Too Sissy?

Or not sissy enough?

The Dinner Guest

My wife invited a colleague from work over for dinner tonight.  I greeted him at the front door wearing a black satin French maid's dress.  After offering him a drink, I took him to where my wife was waiting for him.  Watching him from the corner of my eye, I could see he was as surprised to see my wife dressed as she was as he'd been to find her husband dressed like a sissy as he was greeted at the door.  I wondered how surprised he'd be when he found out my wife was going to require me to suck his cock for her before he fucked her later.

Spying on Miss Sharon

She didn't see me spying on her.  But I am so obsessed with Miss Sharon that I had to sneak in and watch her getting dressed.  God!  She is so beautiful!  And so sexy!  Look at her sexy strip of hair showing through her panties.  Umm!

Sissy Appreciation Sex # 102 - For Jennifer

Jennifer is one of my favorite followers.  She leaves wonderful comments.  I hope she likes a good blowjob.  Because I sure do.

Thank you Jennifer!

Not Just A Night Out With The Girls

I can always tell when my wife is getting ready to go out on a Friday night that, contrary to what she says, it isn't really going to be "just a night out with the girls."

Sissy Back Massage

'Nuf said.

I Feel Pretty

Oh, so pretty,
I feel pretty and witty and bright!
And I pity
Any girl who isn't me tonight. 

Credit - West Side Story

Booby Contest

Meet the finalists in the Vera Wang Institute for Male Modification, a/k/a "Sissy School," Annual Booby Contest.  This year a first year girl is giving the upper class girls a run for their money.

 But really, there are no losers in this contest.

Sissy Appreciation Sex # 101 - For Cunny Honey

Cunny Honey, a/k/a "The Cunnilinguist," has a penchant for something sissies specialize in, so I figure Cunny Honey will appreciate what I have planned for her as a token of my appreciation for her following my blog.

 Please be sure to visit her blog.  Thanks Cunny Honey!

You May Look Leeanne

But you may not touch.  Miss Sharon loves to torment sissy Leeanne with her hot, sexiness.  

 But she won't let Leeanne touch her.  No.  Leeanne pleases Miss Sharon in one way and one way alone.

Sucking cock.

Sissy Service

Seeing a sissy in this position requires no explanation as to what she has in her mouth.

Crawl Over Here Leeanne

Miss Sharon had just returned from a date and was in need of special attention from Sissy Leeanne.  I assumed it would begin with her feet, but was hopeful, always hopeful, that it would lead to more.

Sissy Wedding Night

Wouldn't this just be so sweet?

Too Sissy?

Or not sissy enough?

Sissy Soldier Girl

This sissy loves entertaining the troops.  And the troops love being entertained by her.  But the reason they're all smiling is that they have plans for the sweet sissy that extend off of the dance floor.  Soon she'll be thanking them in a special way for serving our country.

Working Late

I'd had to work late.  Again.  My boss insisted that the report due out the following Monday had to be on his desk before I went home for the day.  My wife seemed very understanding when I'd called and told her not to wait up for me.  When I quietly opened our door, so as to not wake her, this was the first thing I noticed.

Then I heard the noise.  I didn't want to believe it at first, though there was no mistaking my wife's grunting in sexual pleasure.  Tiptoeing to our bedroom door, I slowly cracked the door and that is when I understood why my boss insisted that I work late.

And why my wife was not upset that I had to.

Cruel? Or Necessary?

Sometimes a sissy simply has to be shown tough love.  When she's been locked in chastity for a month, and can't hold her sissy juices back for even minute under the toe of her mistresses heel, there has to be a consequence.

 And of course, she is expected to clean up her little mess as well.  Maybe next month she'll do better.

Too Sissy?

Or not sissy enough?

Preparing to Work a Party for Miss Sharon

Miss Sharon had strict requirements for her sissy when she was hosting a party.  Not only must her sissy prepare the hors d'oeuvres and serve guests their drinks, but she also had to be prepared to provide other services, as requested by the guests, and without hesitation.  Miss Sharon would not suffer foolishness from her sissy.  Miss Sharon was taking sissy Leeanne through her preliminary walk-through now.

Playboy Bunny Class

First year girls could not sign up for this elective.  It was reserved for third years.  And it was, by far, the most popular last year class for sissies at the Vera Wang Institute for Male Modification, a/k/a "Sissy School."  There was only enough room for a few girls, and auditions were required before admittance.  None of the sissies who were accepted ever revealed what they'd done during their auditions to be accepted.

But you can imagine the rumors.

Casual Friday

Sissy is not required to wear her French maid's uniform to perform her household chores on Casual Fridays.

But that doesn't mean her backseams don't have to be straight. 

Miss Sharon Wet Dream

Last night I woke in the middle of an intense dream, soaking wet.  In my dream, Miss Sharon made love to me like one of her girlfriends.  It was short-lived pleasure though, as I soon realized that she would never permit a sissy such intimacy.

Preparation

"Oh yes baby!" my wife sighed as I carefully shaved her pussy.  "Jermaine loves it smooth.  He'll be very pleased with your effort on his behalf."

Clubbing

Sometimes my wife likes to go out clubbing with me.  She usually ends up dancing with lots of guys.  And if she likes one, she'll take him into a back alley and let him have her.  So that she doesn't have to leave right away (because of the cum dripping from her), I'll go out back after each guy returns to the club and clean her.   

 On some nights this can happen several times.

Too Sissy?

Or not sissy enough?

A Satisfied Wife

I just returned from serving my wife's lover breakfast.  He had to go to work.   But she doesn't like him to leave hungry.  Seeing her in our bed, I immediately knew that she'd had a good night.  Now it was my turn to make her feel good and to clean her pussy.

The Sissy Bride

The first time a sissy bride cleans her wife's pussy after she consummates the marriage with the Best Man is a special moment that will always be cherished.

Waiting

I was not allowed into our room at this point.  My wife was in there with her boss who'd come to our house for dinner.  But she permitted me to observe through the partially opened door.  The position she'd assumed left me no doubt what she was preparing to do with him.

Woman v Sissy

A sissy witnesses a woman being fucked from this perspective:

A woman witnesses a sissy being fucked from this perspective:

Not An Elective

At many schools for sissies, teaching sissies how to share a cock is an elective.  But at the Vera Wang Institute for Male Modification, a/k/a "Sissy School," such deportment is considered a mandatory requirement.  Wives should be able to expect their sissies to work together if friends loan their sissy husbands to each other for special occasions.

 

Vera Wang Institute for Male Modification, a/k/a "Sissy School" Curriculum

The entire curriculum at the Vera Wang Institute for Male Modification, a/k/a "Sissy School," was designed to train budding sissies to please their wives, girlfriends and Mistresses, whatever the case may be.

However, no sissy could graduate without first earning an A+ in this particular subject.

Sissy Dormitory

The first year girls at the Vera Wang Institute for Male Modification, a/k/a "Sissy School," have to live in dormitories and share rooms.  The goal is to help young sissy trainees become less modest about their new bodies.

Too Sissy?

Or not sissy enough?

She Was Soooo Right!

My wife told me that there really was nothing quite like the sensation of a man spraying his cum all over your breasts.  I'd just received my implants and she was showing me why it was the best decision I'd let her make for me.

Date Night

And that meant I was expected to bathe my wife as part of my assistance to her getting ready for whoever was going to come by to take her out for the evening.  She insisted that I participate by helping her look her sexiest for her dates.

On Your Hands And Knees Sissy!

Now!

Too Sissy?

Or not sissy enough?

Which One Is The Sissy?