A Reluctant Sissy -- Part 5 -- Elegant Nights

When I opened my most recent update letter from Mrs. Trainer, these two photos fell out of the envelope.  I must have stared at them for five whole minutes before I could tear myself away from them to read her letter to me.

"Dear Mrs. ____, 

I am very pleased to report that our progress with your son is proceeding very, very well.  An entirely new personality is being revealed; One that is demure, gentle and obedient.  I am sure you will be delighted when you see the finished product in just a few short months from now.

Now that our sissy students have been with us for 16 weeks, the intensity of the training and our expectations of our "ladies" increases quite dramatically.  Days are longer, infractions are dealt with more severely and our behavior and personality manipulation (some might call it brainwashing) is taken to a new level.

We are very fortunate that our school is located just a few miles from a Royal Air Force base.  Over time, we have developed a relationship with a select group of senior officers from the base that we can trust.  Every Thursday night, we invite our officer friends over for a very swanky party with our darling sissies.  The officers tell their wives that they are working late (seems to happen every Thursday!) and our sissies entertain these handsome gentlemen from early in the evening until well past midnight.

We dress our sissies up in their finest outfits to show the officers how much we appreciate their company.  And it should be no surprise that your little Kimberly is one of the officers' favorites!  The gentlemen arrive -- in full dress uniform, of course -- around 6:00pm.  It's cocktails and flirting with the sissies.  Then dinner at 8:00 followed by more cocktails, dancing and...well, whatever the officers want to do.  We have plenty of space here at the school for the officers to take a sissy somewhere private for some one-on-one time.  This goes on for a few more hours until our gentlemen guests are exhausted and need to head home to their families.

You may be curious as to why we incorporate some much interaction with men into our training program.  Let me explain.  First, when our sissies are in the presence of alpha males, like our wonderful RAF officers, they are shocked into realizing just how little they have in common with such real men.  Being surrounded by strong, masculine, muscular men, our sissies feel small and delicate and weak.  They recognize nothing of themselves in our handsome guests.

Second, it is understood by all that the sissies are to cooperate with and please our guests at all times.  Our officers are accustomed to having their instruction followed and their needs met.  It is wonderful practice for our sissies to understand that their role is only to please and to serve.  At this point in their training, they are beginning to feel a sense of fulfillment, and even pride, in their submissiveness and servitude to these strong, dominant men.

I will write again with more photos as soon as I can.

Sincerely, Mrs. Trainer"

I put away Mrs. Trainer's letter and again marveled at the photos of my beautiful, elegant, ladylike son.  I could just imagine how these older gentlemen would absolutely drool at the site of such a lovely young "girl."  And while at first I was shocked by the thought of him being forced to endure...encounters...with men, I could see Mrs. Trainer's point that it was probably a very powerful indoctrination and re-education tool.  I reminded myself of just how bad his behavior was before I sent him away and how I was in favor of whatever Mrs. Trainer felt she needed to do to fix his awful behavior and attitude. 

 

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 Simple Minded Sissy

Poor Sissy Gretchen.  His transformation had been particularly difficult.  He had resisted the process every step of the way.  He simply would not cooperate with the plans I had for him.  But I knew he would make an exceptionally pretty -- and valuable -- sissy once the transformation was complete.

Through a combination of drugs, hypnosis, electroshock and beatings, I was eventually able to break through his resistance and complete his conversion.  And I was right -- I was able to transform this young man into one of the prettiest sissies I ever made.

Aided by a daily dose of narcotics, Sissy Gretchen becomes a simple minded little sissy who no longer has any will of his own.  He will obediently follow any instruction given no matter how demeaning or disgusting.  That makes him the perfect sissy escort.  I have a long list of wealthy men who have no problem paying me thousands of dollars for a few hours with this gorgeous and completely docile sissy love doll.

At the end of every long day of sissy sex servitude, Sissy Gretchen has an unusual bedtime routine.  He strips off his pretty dress and slips into a sexy, sheer and very revealing baby doll nightgown. Then he allows me to put a ball gag in his mouth and to tie his wrists and ankles to the bedposts.  Sissy Gretchen falls asleep, content and mindless.  I leave his bedroom light on.

These bedtime preparations are required because during the hours before dawn, Sissy Gretchen will awaken as yesterday's dose of narcotics begin to wear off.  As his brain begins to refocus, he remembers who he was -- and what he has become.  I expect his mind is flooded, all at once, with images of his feminized self submitting to the disgusting demands of his many male clients.  The terror he experiences is amplified by seeing his own gorgeous sissy reflection in the mirrored ceiling above his bed, his enormous breasts barely concealed by his sheer baby doll nightie.  He writhes in mental agony on top of his bed, struggling to free himself from his lashings.  His screams muffled by the bright red ball gag in his mouth.

I allow this to continue to a couple of hours until I am ready to get out of bed and deal with poor Sissy Gretchen.  By then he is a wreck, overcome by his exhaustion and horror.  I stand above him and tease him.  "Oh, what's the matter sissy?" I might say.  "Don't you like staring at your sexy reflection in the ceiling mirror?  Aren't you happy that you are now a perfect sissy slut?  Didn't you have fun yesterday -- and everyday -- doing all those nasty things you did to all those men?"  It doesn't take much to get him to start sobbing.

Eventually I take pity on him I inject him with today's dose of narcotics.  He slips back into unconsciousness for a couple of hours.  When he awakens later, the episode he experienced just a few hours earlier will have been completely forgotten, as he begins another day of obedient sissy sex servitude.

Young Sissy Created for Older Men

Stepmother was so excited!  Tonight, Sissy Suzette was going out on his first date -- with a MAN!

Sissy Suzette's cruel stepmother, Mildred, had been transforming her stepson Stanley from a normal teenage boy into a feminized plaything for older men.  Two years ago,  Stanley/Suzette's father ran off with another woman, leaving Mildred to care for Stanley on her own.  She decided that she would take her revenge on her husband by destroying his only son.

And so, after two years of hormones, strict training and brainwashing, it all came down to this.  Poor Sissy Suzette!  He is so terrified about being sent on a date.  He was close to tears this afternoon as Mildred helped him with his hair and make-up.   

Mildred had posted Suzette's profile on Match.com, including some sexy, glamourous photos.  The profile said Suzette was 19 years old -- and that she was interested in dates with much older men.  Well, within days it seemed like millions of men in the area eagerly responded.  Mildred was delighted when she discovered that she could subject poor little Suzette to a limitless number of romantic encounters with different men.

Mildred carefully selected outfits for Sissy Suzette that were both sexy and classy.  A rigorous diet cimbined with a little padding in all the right places gave Sissy Suzette the alluring shape of a pretty young woman.  And with relentless training, Sissy Suzette could now talk and sit and eat and walk exactly like a girl. 

It was time for Sissy Suzette's first encounter.  The date was arranged at a french restaurant downtown.  Mildred sat at a nearby table and enjoyed the show!  Suzette's date, a 50 year old executive, was practically drooling throughout dinner, ogling the pretty young thing sitting across from him.  Sissy Stanley flirted with the older man as his stepmother had trained him. 

Watching the bizarre scene unfold was getting Mildred excited.  She even felt her panties become damp as she saw Sissy Suzette's date place his hand on Suzette's stockinged knee under the table.  This was going even better than she had hoped!

When dinner was over, Mildred followed the pair out to the parking lot where the two were passionately making out, the older man pressing her stepson against the man's BMW as he aggressively kissed the pretend girl.  After a few moments, the two climbed into the man's car.  Soon the two would be back at the man's house, where Sissy Suzette would pleasure his date with his soft manicured hands and his red glossy lips.  As Mildred watched them drive off, she had an orgasm imagining her nephew Stanley sucking on his date's cock and making him cum. 

Mildred rushed home to arrange many, many more dates for her sissy nephew.

Rotten Stepson becomes a Perfect Sissy

When I decided to have my stepson transformed into a feminized, obedient Sissy, I had no idea where this would lead.  Mostly I was sick of his rude behavior, his back talk and his laziness.  It was such a relief when I had him sent away for his year-long transformation.

When I first brought him home I was totally amazed by his transformation.  Physically he had been completely changed.  He was now a pretty, delicate, completely feminine little Sissy.  His hair was long and had lovely coppery highlights.  He had lost twenty or thirty pounds -- maybe more -- and was developing the sweetest little breasts.  Everything about his body and appearance was now so girlish.  But his physical transformation was nothing compared to his mental transformation.

He was now utterly and totally obedient to me.  He seemed to have no desire other than to please me. He was such a delight to have around the house.  He needed no instruction to keep the house spotlessly clean, to prepare my meals, make my bed -- everything!  I let him help me dress and undress me and even bathe and massage me. He would never speak unless spoken to.  When I would enter a room, he would stop whatever he was doing, lower his eyes to the floor, and curtsey to me.  It was marvelous.

But over time, I developed a strange attraction to my litle Sissified creation.  He was so devoted to me and took such good care of me.  I soon started to enjoy my Sissy in more...intimate ways.   I had my little Sissy joining in my bath and in my bed.  I enjoyed running my hands all over his soft little body.   I enjoyed pressing his naked body against mine, letting him play with my big boobs while I played with his tiny little titties.  And best of all, I loved feeling his sweet little mouth and tongue on my pussy.  I hadn't realized how thorough his training had been!

Who knows?  Maybe I'll get my Sissy stepson some big sexy breasts so he can be more like me.  I bet he'd like that!

Making a Perfect Housewife

Sissy Candi was an occassional crossdresser who liked going to the local drag bar on Saturday.  Sissy Candi was young and pretty, but also shy and nervous.  He kept mostly to himself, nursing a glass of white wine while watching the drag show and the scene aroung him.

That's exactly how Master Drake found Sissy Candi when he sunk his claws into him.

After luring Sissy Candi to leave the bar with him one Saturday night, Master Drake imprisoned the poor innocent sissy in his home. Master Drake forced Sissy Candi live as a woman 24/7. 

Through relentless beatings and mind games, Master Drake stripped Sissy Candi of any sense of confidence or self.  He lives now in a continuous state of nervous fear and dependence.  Poor Sissy Candi. 

Master Drake forcibly transformed Sissy Candi from a part-time crossdresser who enjoyed exploring his feminine side on Saturday nights to a full-time Sissy Housewife.  Master Drake insists that Sissy Candi act and look like an obedient, docile and devoted 1950's-style housewife who lives only to serve and please her "Husband."

Sexy Sissy Escort

Feminized to absolute perfection, Sissy Annette was ready for another night as a high-priced sissy escort for visiting businessmen.  It had been a very busy week as there was a convention in town.  Sissy Annette was going on 3 or 4 dates every day!

How did poor little Sissy Annette end up in this position?  Three years ago, as a young crossdresser, he responded to an ad on Craig's List offering "transformation" make-up services from a woman named Vanessa.  Vanessa was an expert and made Sissy Annette look and feel completely feminine -- for a heavy price.  Sissy Annette was soon having make-over sessions with Vanessa several times a week and was soon deeply in debt.  Sissy Annette was addicted to Vanessa's tranformations and was completely ensnared in Vanessa's web.  

Sissy Annette soon moved into a spare room in the basement in Vanessa's house and Vanessa began keeping Sissy Annette in dresses and make-up 24/7.  Heavy doses of hormones were slipped into Sissy's food and Vanessa used mind control techniques to strip away the Sissy's independence.  Vanessa became Sissy Annette's pimp and she was determined to make this a "profitable" relationship.

Starved and brutally corsetted, Sissy Annette's body became slender and sexy.  Her swelling breasts filled out her tight dresses.  Men were highly aroused by the sight of her and enjoyed running their rough hands all over her delicious curves.

Sissy Annette sees her next "date" from across the hotel bar.  It is time to be flirty and charming and docile.  She will soon find herself on her knees in a hotel room upstairs... 

A Sissy Accepts his Fate

After nearly a year of intense training, massive doses of hormones and severe psychological abuse, poor little Sissy Jenny finally surrendered himself to his new reality.  He abandoned any remaining sense of the high school drop-out he was.  He also abandoned any remaining hope that he might someday be able to escape from the captivity of his Master.  Sissy Jenny accepted his fate -- that he was now the fully feminized, sissified love toy for a strong, masculine and demanding Master.  Sissy Jenny gently wrapped his soft, manicured fingers around his Master's swelling cock and whispered, "How my serve you, my Master."

Sissy prepared for master

After nearly six hours in the beauty salon chair, Sissy Crissy was 
finally ready to be presented to his Master.  Tonight was going to be
the most important night of Crissy's life; tonight Crissy would pledge
 himself to his Master for all time in a Sissy Enslavement ceremony.
All of the Master's friends would be in attendance tonight and
Crissy wanted to make the Master feel proud.  Months of severe
training, beatings and brainwashing had transformed this teenage runaway
boy into the most exquisite sissy love toy ever.