Babysitters? Who Needs A Babysitter?

When Sissy Leeanne and Sissy Kaaren's wives went out together for "Girls' Night Out," they learned long ago there was no need to pay a babysitter to watch after their sissy husbands to make sure they behaved while they were out.  They had things worked out just fine to leave their sissies alone together.

Sissy Isn't Modest Anymore

This is the third baby sissy's wife has borne of her boyfriend.  Of course, sissy has been the babies' mother.  She has long since stopped worrying what the neighbors would say about her, and so on hot days doesn't even attempt to hide the fact that her wife keeps her in chastity.

Sissy Bath Time

Didn't I Tell You My Sissy Husband Could Suck A Mean Cock?

Can you cum in her mouth?  Why of course!  She loves it!

The Cuckold

“Yes.  The evening was lovely.  And yes, she’s right where I told you she’d be when I arrived home.  Even if she didn’t enjoy your taste, she’d do it.  For me.  But yes.  From the sounds she’s making, I’d say she does like the way your sperm tastes.”

The Nightwatchman

Sissy's friends couldn't understand why she seemed to love her job working alone all night in the local department store as a nightwatchman.

Prepping Sissy

Do I plug her?  Duh!  Of course I do!  She’s needs plugging.  She needs the reminder that her hole is meant to be filled.

Loving Cock

Eventually, this cock will end up at the back of sissy’s throat.  But for now, she’s being permitted to relish in the touch and feel of her prize.

Too Slutty Of A Sissy?

Or not slutty enough?

A Day In The Life Of A Sissy

Scrubbing the floors.

Washing the dishes,

Getting in her daily exercise.

And finally, collapsing out of exhaustion.

Sissification Complete

When Mary’s husband had first confessed his desire to wear women’s lingerie, she was uncomfortable.  But she loved him and tried to be open-minded about his kink.  Then, she discovered that she enjoyed their girly play time together.  Soon, she was all in and began doing everything she could to help her husband become completely feminized.  But now, after all of their efforts had resulted in the pretty sissy kneeling on the floor at the foot of their stairs, sucking a real man's cock for the first time, Mary was worried that she may have gone too far.  On the other hand, it would be Mary's first time with a real man in over a year, so maybe she'd just have to make the best of it. 

A Sissy's Place Is On Her Knees

Always

Always

Always

Always on her knees

Which One Is The Sissy?

Ugh!

All her sissy husband could do was watch as his wife was filled with the biggest, fattest cock either one had ever seen.  Sissy had barely gotten his pretty red lips wrapped around it to fluff him, but his wife was swallowing the monster inside of her cunt like she was starving for the pleasure it provided.

Until Death Do They Part...

Too Slutty Of A Sissy?

 Or not slutty enough?

Quiet Times

The man who visited earlier has gone home.  Sissy’s wife is sated, but still relishes the affection her sissy husband has for her in these quiet moments they share in the aftermath of her lovemaking.

The Weekend Visit

Your best friends from college visited this weekend.  When your wife revealed to them your dirty little secret, and after they made you dress up like the little sissy you are, the rest of the weekend was spent with your wife being filled in all of her holes with their thick, hard cocks.  And you?  Clean up of course.

Dressed For Riding

But for riding whom?  My guess is her sissy husband.

Lessons Taught

The nuns charged with the incorrigible boys sent to Sissy School were as strict as their reputation.  If a sissy misbehaved, there would be consequences.  But, as you also might expect, the consequences usually had a real world practical application.

Best Dream? Or Worst Nightmare?

 I always fantasize about dressing up as slutty as possible and then driving in a manner to ensure I’ll be pulled over by a policeman, who then checks my driver’s license and discovers I’m a sissy - not a real woman.  From there my fantasies take so many different directions.  What do you think?  Is this one of my dreams?  Or one of my nightmares?

Practicums

Some of the best teaching classes at The Vera Wang Institute for Male Modification, a/k/a "Sissy School," were the practicum courses where advanced sissies would demonstrate complete sexual activities, such as this course where sissy terri demonstrates her very practiced skills in performing felatio upon one of the many male demonstrators employed at Sissy School.  Notice how intently Sissy Kaaren watches terri in the background?  Soon, Kaaren is thinking, 'I hope to be the demonstrator.'

Practical Shoes

Sissy knew these heels weren’t practical for going to the grocery store.  So did her wife.  But her wife insisted she dress the part, no matter where or what she did, even if it meant extra attention being focused upon her during her travels.

Your College Roommates

They didn't believe her at first.  When your wife invited both of your college roommates to visit for the weekend, neither of them could believe how she had feminized you since your marriage a year before.  But seeing you.  Seeing how hot and sexy you looked in your new, more shapely, definitely feminine body.  And then, seeing how readily you accepted your wife's instruction and guidance as you sucked first one, and then the other roommate's cock, they believed.  And did they ever like the new you!  Add in the bonus that your wife let them fuck her all weekend too, and you were suddenly their best past roommate ever!

Taken

Sissy watched her wife being taken by her boss and thought, “So that’s how a woman wants to be taken!”

Maintenance

Sometimes, even when she’s been a very good girl, sissy’s wife administers a spanking just to make sure her sissy husband doesn’t get all uppity.

Going Live

Her initial round of training completed, the recently feminized sissy is taken through her paces during her first live performance.  Her wife’s boss takes the lead, as he is the one who will be in charge of both of them in the future.

Sibling Rivalry Truce

Once her older sister accepted that her little brother couldn’t resist dressing in her underthings, she and her sissy brother found they had so much more in common than they ever knew.  For example, she loved having her pussy eaten, and sissy loved eating her pussy.  Their parents were thrilled to see the two getting along so much better.  They didn’t need to know the true reason.  Did they?

Muscle Memory

During the early stages of sissy's feminization, her wife required her to do this 100 times each morning.  "Only through repetition," she always said, "will your feminine mannerisms truly become second nature.  And although a real man could never do what you are doing, I promise you, when you are with one, he'll spot you as a phony immediately if he sees you fumbling with this most decidedly feminine act." 

Too Sissy?

Or not sissy enough?

Instinctual Need

As her sissy husband watches her wife fondling the cock that will soon impale her, sissy realizes why she needs this.  The depth to which her man will plunge is graphically demonstrated as sissy’s wife stands next to her man holding his rock hard cock by her side.  No wonder she squeals with such animalistic response each time the two of them couple.

Time To Prove It

“See the guy in the corner honey?  He’s the one.  I want you to go over to him and suck his cock.  Right here.  In front of everyone.  Now be a good sissy and go show me what you’ve learned.”

Sissy Surprise

“You’re going to put that inside of my wife?”

“I am.  After you suck it sissy.  Now stop staring and get busy.”

The Sissy Scout Mistress

It’s true that the entire purpose of the camping trip was to help the young Boy Scouts work on their rope tying merit badges, but the young Scout Mistress hadn’t counted on the boys being familiar with such advanced rope tying techniques.

Shaving Is Part Of Being A Sissy

Sissy’s wife told her she could get rid of this job with electrolysis, but there was something about shaving here that sissy just couldn’t let go of.

Mesmerized

Although she was the one who feminized her husband in the first place, sissy’s wife was nonetheless mesmerized by how her sissy husband had taken to cocksucking and swallowing sperm.

Sissy Headphones

I’ve always enjoyed listening to music through headphones - even more so with this particular pair.  For the life of me, I can’t figure out what it is about this pair that I love so much. 

Missing Something?

Really sissies!  One of you should pay some attention to those lovely balls.

Not Real

  But my oh my!  If it were. Mmm, mmm, mmm!

Job Perks

Sissy always provides her wife’s boss special treatment when he visits for business dinners.  And the reason why her wife is President of Marketing you're wondering?  Well, she earned position that on her own merit.  The blowjobs are a perk of her sissy husband’s new position as her maid.

The Rose

Who was it who said, “A rose by any other name would smell as sweet?”

Sissy Can See Clearly That Her Wife Has Been Up To Mischief At Work Today