Sissy Attitude Adjustment

Poor Sissy Millie just couldn't seem to accept what was happening to him. 

Physically, Sissy Millie was a huge success -- his forced transformation from occasional crossdresser to chemically and surgically feminized sissy was nearly perfect.  His face was smooth and beautiful, his body was soft and slender.  His hair was long and full.  And his boobs were...well...incredible.  Just look at them!  I can't resist squeezing them and playing with them!

Everything was perfect except for his attitude.

You see, Sissy Millie continued to insist that he was "a man."  He kept shouting that his name was Simon and he would never be another man's full-time, live-in sissy slave.

This was a real problem for me.  Sissy Millie's new owner was scheduled to take possession of his sissy in just three weeks.  But Sissy Millie's attitude -- his entire mental state -- needed a major adjustment.  And quickly!

I've been through this many times before and I have never failed to break a sissy. Sissy Millie is going to wish he had cooperated with his transformation and succumbed to his new life before it came to this.  He is going to endure punishment beyond his wildest imagination.  Once it begins, he is going to start begging me to stop the torture -- begging to be allowed to embrace his new life as a sissy maid and sex slave.  But I am not going to stop until I know that Simon is gone and only Sissy Millie remains. And if that takes three weeks, well that's OK with me. 

Sissy Millie has been tightly corseted, bound and perched on that little stool all night long, a 12 inch dildo vibrating and pulsing wildly in his sissy pussy.  Morning has finally arrived after a long, painful and sleepless night.  He is terrified and exhausted. But his worst fears about what are about to happen to him are nothing -- NOTHING -- compared to what this final stage of his transformation will be like. We will completely break his will and his soul.

I feel no guilt about the suffering Sissy Millie will soon endure.  This is all his own damn fault.

A Sissy Begs for Forgiveness

"Oh, please, Stepmother," I begged.  "It won't happen again.  I am so sorry.  I promise.  Please don't punish me.  PLEASE!"  I stood in the middle of the room, perched in my towering high heels, my manicured hands clasped together as I repented for my failings.

"SILENCE!" Stepmother shouted.  "You are NEVER to speak unless spoken to!"

I lowered my eyes to the floor, now terrified that I had made my terrible situation much worse.

"Look at you, you pathetic sissy.  I can see right through that ridiculus outfit you are wearing.  Only a real sissy slut would dress like that.  Aren't I right?"  she asked.

"Yes Ma'am," I replied softly, even though we both knew that she picked out all the outfits I was allowed to wear.

"You broke a very expensive teacup when you were washing the dishes today and that sort of misbehavior must be punished.  So what will it be, sissy?  The paddle or the dildo?"

Oh no, I thought.  This was going to be bad.  Even though my bottom was still raw from my last spanking, I really hated being punished with Stepmother's strap-on.  "The paddle," I said.  "Please," I quickly added.

I pulled down my panties, lifted my billowy skirt over my waist, and lay across Stepmother's lap.  But before she started paddling my bottom, she called out loudly, "Tiffany, please come in here!"

And in walked Tiffany, my stepsister.  Oh God!  What was Tiffany doing here?  It was so humiliating having my much younger stepsister seeing me like this, laying across Stepmother's lap, with my skirt hiked up and my bare bottom sticking up in the air. I started to try to squirm away, but Stepmother is so much stronger than me and she held me firmly in place.  "Be still, Sissy!"  Stepmother growled.  Tiffany roared with laughter seeing me like this.

"You see, Sissy," she explained, "I decided that it was time to show Tiffany how to discipline you.  That way we can ensure that you will always be as obidient to her as you are to me.  Now go ahead, Tiffany.  Do it just the way I explained."

Tiffany picked up my punishment paddle and waved it in front of my face.  "Kiss it, Sissy," she said with an evil grin.  I did just as instructed, knowing that to protest would be very unwise.

And with that Tiffany began to administer 20 stinging blows to my bare bottom, while her mother held me firmly in place on her lap.  After the first ten, Stepmother said to Tiffany, "Now dear, if you don't spank him harder than that, how will he ever learn his lesson?"

Tiffany put all her strength into the next ten blows.  I could hear her laughing as she abused my bottom.  Tears were pouring down my face as the pain and humiliation were unbearable.

When Tiffany was done with my beating, Stepmother started rubbing my burning bottom.  "Have you learned your lesson, Sissy?"

"Yes Ma'am," I whimpered.  "I'm very sorry. I learned my lesson."  I started to get up from Stepmother's lap.

"Not so fast, Sissy," she said with a sneer as she kept me pinned to her lap with her strong arms.  "You didn't thank Tiffany for teaching you a lesson and helping you to become a better Sissy."

I choked back my tears and forced myself to say, "Thank you Tiffany for teaching me a lesson and helping me to become a better Sissy."

Stepmother administered a sharp bare-handed slap to my bright red bottom and snarled, "From now on you will refer to her as Mistress Tiffany, do you understand?"

"Yes, Stepmother.  I understand.  I am sorry for my inpertinence, Mistress Tiffany."

"That's more like it," Stepmother said with a satisfied smile.  "Now get yourself cleaned up and get started on making dinner."

My Sissy in the Tub

I have always loved my husband very much.  He has always been kind and gentle and generous with me. 

But after his second heart attack, I insisted that he quit his high pressure job and make some...lifestyle changes. 

That was three years ago.   Now, with my guidance, my husband who was once a powerful executive has been transformed into the most delightful and feminine Sissy gurlfriend. 

Here we are in the tub enjoying our time together.  His pale skin is soft and smooth and so beautiful.  His hair has grown long and is now a lovely shade of red.  And his breasts!  They are magnificent!  I simply can not resist playing with them. 

And our love life has never been better.  Of course his little tiny cock can't even get hard anymore.  But my husband can spend hours with his face between my legs bringing me orgasm after orgasm with his talented little tongue.  When that isn't enough for me, I let him fuck me with a strap-on.

And when it's his turn for a little pleasure, I wear the strap-on, sometimes still wet with my juices, and fuck his little sissy pussy.

Sissy Weddings!!! A Young Sissy Bride Prepares for his Big Day

I do so enjoy a Sissy wedding!  Almost nothing fills me with so much joy as seeing one of my Sissy creations forced to marry a man that I have selected for them.  As a full-time Sissy Trainer, I am paid very richly to provide Sissy brides to wealthy men looking to fulfill their fantasies.                                                                                                                                                                                 Sissy Abigail's wedding was one of my favorites.  Just look at him -- so young, so sweet, so scared!  I had such a good time preparing Sissy Abigail for his big day.  All those months of trying on gowns, learning to recite the vows I wrote for him, the dance lessons, the dildo practice...

Sissy Abigail was forced to try on hundreds of gowns before I selected the perfect one.  The girls at the bridal salon had such fun teasing and torturing my little Sissy.  They gushed about how sweet or how sexy each gown made him look.  They told Sissy Abigail how pleased and aroused each dress would make his new Husband/Master.  And of course they talked endlessly about how exciting Sissy's wedding night would be and how amazing it would feel being fucked by his new Husband/Master.

 

The dresses above were two of my favorites.  Sissy Abigail looked simply darling in them both.  But when he tried on the dress on the left,  I knew it was the one!  Seeing my little Sissy encased in acres of chiffon left me breathless.  And the effect on Sissy Abigail was just as profound.  He felt so helpless and hopeless -- just look at his sad and scared little face -- priceless!  He felt like a present that was beautifully wrapped for his new Husband/Master to open and enjoy.  And of course, the little Sissy was absolutely correct.  That is exactly what he had become; a possession for a superior male who would own, control and dominate him for the rest of his Sissy life!