A Reluctant Sissy -- Part 7 -- Going Home

It had been nearly six months since I had deposited my rotten, trouble-making son at Mrs. Trainer's "academy" outside of London when I received this letter from her:

"Dear Mrs. _______

The big day has finally arrived!  Your son has graduated from our sissy transformation program and I know you will be absolutely delighted with the results.

Your darling Kimberly is prepared to be obedient and submissive to you in every way.  I would urge you to begin thinking hard about how you will incorporate Kimberly into your life at home.  I'm sure you are already thinking about how Kimberly will take care of all the household chores -- cleaning, cooking, laundry, ironing, etc.  But there is so much more you can expect from your new sissy.  Your sissy exists only to enhance your life in every way imaginable.  Get creative.  Your sissy can serve you breakfast in bed or massage your feet while you are eating lunch (that he has prepared and served you). Your sissy can bathe and dress you --- there is no point being modest around your sissy; it is best to think of your sissy as an extension of yourself.  Your sissy can tidy up after you have enjoyed time with your lover."

I stopped reading for a moment to let Mrs. Trainer's words sink in.  Having Kimberly bathe and dress me...? I hadn't thought of that, but it gave me a tingle just thinking about it.  And it had been years since I had experienced a lover -- and all because I was constantly dealing with my son's misbehavior.  Well, that would certainly be fair -- making Kimberly tidy up after I'm done having sex with a man since he prevented me from having any romantic relationships for so long.

I returned to the letter.

"It is important to keep your sissy busy and on a strict schedule at all times.  For many of our clients, sissy bedtime (I we mean lights-out!) is 8:30pm, with wake-up at 4:30am.  That gives your sissy 90 minutes to prepare themselves for the day and make themselves look lovely for you, and another hour to prepare the house and breakfast for you by 7:00am.  Of course you will establish whatever schedule best suits you.

And PLEASE, do not miss opportunities to punish and berate your sissy.  The smallest mistake or infraction (even if you have to make it up!) should be dealt with severely.  Over the knee spankings are very effective (always use a hairbrush to protect your hands) and scolding is always appropriate.  Reminding Kimberly frequently that he is a pathetic, weak, stupid, worthless sissy is very beneficial.

We will be putting Kimberly on a plane home to you in just seven days from now.  We will send several cases of clothes and other items that Kimberly will need.  We will also send along our sissy owners manual that is filled with useful tips for getting the most from your new sissy.

Enjoy the photo enclosed.  We are having Kimberly model the outfit that he will wear on the plane ride home to you.  This is what he will look like when you see him next week at the airport.  Isn't this marvelous.  So beautiful and so impractical!  He will certainly get plenty of attention during his journey home.

All of us here at the Academy have been delighted to work with your son.  We are very pleased with the changes we were able to make in him.

We are always here for you if you need us in the future.

Regards, Mrs. Trainer" 

A Reluctant Sissy -- Part 6 - Sissies for Hire

About a month had passed before I received another letter from Mrs. Trainer.

"Dear Mrs. ____,

Sorry for the delay in writing but things here at the school are very busy indeed.  This is a crucial time in our training process where we expect to see our sissies display the attitude and actions that are expected of them without any reminders, prodding or punishment.  We are still enjoying our trips into London and our Thursday night officers' parties.  And I am delighted to report that your son is by far the best behaved, hardest working, most delightful little sissy in the entire class.  We are absolutely thrilled with how far he has come in just five short months here.

There is a special privilege (well, I 'm not sure the sissies see it as a privilege) that we reserve for our most accomplished, most feminized, most obedient sissies.  On occasion, if one (or more) of our handsome, older Air Force officers wants to "borrow" a sissy, that is something we can sometimes arrange.  Well, I can assure you that ALL of the gentlemen are asking for time with your beautiful son.

Sometimes an officer will request a sissy to be their date for an evening of dining and clubbing in London.  Your Kimberly  went on such a date two weeks ago wearing that adorable black minidress.  Doesn't he look divine.  Our officer was so proud having this lovely sissy hanging on his arm all evening, showing him off to all his friends."                                                                                                               I stopped reading long enough to look at the first photo.  I nearly fainted at the sight of my son wearing a very sexy minidress -- and looking amazing in it.  He looked so delicate, so feminine.  The short dress made his legs look so long and slender, the high heels he wore added to the effect.   I took a breath and returned to the letter.

"Then last week, another officer borrowed Kimberly for an entire weekend, jetting him off to some swanky island resort.  We assembled some fabulous outfits for your son for this little adventure.  I simply love the very revealing black top combined with the wide leg trousers.  Your son looks like he stepped out of a fashion magazine!  And the fun part of wearing that top - it makes our sissies wish that their boobs were actually larger than they are (but the hormones only work so fast -- don't worry, you can expect a lot more progress in this department over the months ahead).  We also sent your son off with a sexy swimsuit for his resort getaway."

I stopped again to look at these two photos.....

"And please don't be concerned by the expression on Kimberly's face.  I'm happy to report that he is not sneering or frowning for the camera.  Rather, he is genuinely frightened of being sent away for time alone with these men.  As awful as life is for our sissies in the school, they become familiar with their surroundings and the routine and they take comfort in that.  But when they are sent off into the world on their own, with no chaperone, that can be very unsettling.  Your lovely Kimberly was absolutely trembling with fear before being sent off on these two "assignments."                                                                                                                But I'm happy to tell you that in both instances our officer friends were absolutely delighted with Kimberly's company!  

There is a group of three officers who have inquired as to whether they could take Kimberly away for a weekend at a country estate they are renting.  I think that sounds like a marvelous idea.  I'm sure they will find all sorts of ways to keep your darling son busy!  

I expect that there will be some sad faces over at the base when it's time for your Kimberly to be sent home to you.

That's all for now.  We are in the final stages of preparing your son to go home to you!

Sincerely, Mrs. Trainer"

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. 

 

A Reluctant Sissy -- Part 4 - Going into London

I was now getting updates from Mrs. Trainer every couple of weeks regarding my son's feminization transformation.  The latest letter read as follows:

"Dear Mrs. _____, 

Now that our most recent crop of sissy students has been with us for a couple of months, we have added a fun new activity to their schedules.  Every two weeks we get our little sissies all dolled up to spend a fun day in London!  It is so much fun dressing our sissy boys up in the cutest little outfits and to spend an entire day putting them on full display in the busy city.

There is so much to do in London; we usually start our day at a chic salon where the sissies can get their hair and nails done.  The ladies at the salon really enjoy working on our naughty boys and ensure that they all look their very prettiest for the rest of their big day out.  We usually do some shopping for dresses and pretty things at a few boutiques or one of the wonderful London department stores.  Then it's off to downtown (we call it "The City") where we go for lunch at some restaurant crowded with handsome young businessmen.  There is a lot of ogling and leering going on as our sissies try their hardest to ignore all the attention they are getting.  Sometimes a brave young banker will approach one of our tables and try to flirt with one of our boys.  It's very upsetting for our sissies to realize that they have been so feminized that they have become the objects of desire for real men!"

I stopped reading for a moment to take a look at the photos that Mrs. Trainer had included.  My heart nearly stopped when I saw the first photo --  my son in a pretty yellow cardigan, chicly belted around his skinny waist. And this was over a blue polka dot pleated skirt that fell just below his knees.  This was finished with towering pair of open-toe pumps and the same oversized pearl jewelry I had seen in earlier photos.  He looked simply amazing.  So stylish.  Simply gorgeous.  But as always, that naughty boy refuses to smile for the camera!  

I continued reading:

"Our day might include a ballet matinee or high tea at a fancy hotel.  You know -- all the things real ladies love to do.  And our sissies are expected to demonstrate their best behavior and participate enthusiastically in whatever activity we dream up for them.

Of course, your darling Kimberly is so very pretty that he attracts a lot of attention where ever we go.  Doesn't he look so sweet in the little pink and blue sweater and skirt ensemble he's wearing!?!  He wears this outfit so well that I promise that we will send it home with him when his training and transformation here are over."

I looked at the second photo that Mrs. Trainer had enclosed.  It was shocking to see how feminine -- how absolutely lovely -- my rotten son looked.  My mind went into overdrive in that moment, beginning to imagine the new life the two of us would be living when he returned home.  

Mrs. Trainer's letter concluded:

"You may have total confidence that we will complete your son's transformation to our very high standards.  You will be delighted with the lovely and feminine and compliant sissy that you will see in just a few short months.

Sincerely, Mrs. Trainer." 

A Reluctant Sissy -- Part 2 -- Dinner

About two weeks after I received my first report on my son's progress at Ms. Trainer's London facility for enforced feminization and obedience training, I received another update -- with more photos.  Let me share this latest update with you:

"Dear Mrs. ____,                                                                                                                               We wanted to let you know that we are continuing to make good progress with your son's transformation.  As you know, he is rather strong-willed and stubborn - but our staff loves a challenge!  And we have the tools and the experience to break down even the most reluctant sissy.                                                                                                                                                             The enclosed photos show your son dressed for dinner.  Dinner is a rather formal affair here at the facility and we insist that our sissies dress up nightly in an appropriately fancy and feminine manner.  We think your son looks absolutely divine in his dinner dresses.  As you can see, his still refuses to smile for the camera.  He is very unhappy with what we are forcing him to do and he is probably terrified of what the future holds for him.  Regardless, I think he looks simply divine in the nude colored dress and absolutely charming in the green dress"                                                                                                                                               I took a moment to study these latest photos.  I could hardly believe that this lovely creature in the long sleeveless dresses was really my son!  He looked so ladylike, so elegant.  But I certainly did recognize his scowl -- just about the only expression I ever saw him make.  Well, pout as much as you like, sissy boy.  I know you will be no match for Ms. Trainer's staff and their techniques! 

The letter continued:

"I understand that you never received much background on our process here at the facility as I know you deposited your son with us with some urgency.  I thought you would enjoy a quick overview of our process. Every day begins at 5:00AM sharp and our sissies make themselves pretty for the day.  Then for the next 12 hours, it is non-stop chores and training. We are proud of what wonderful domestic workers our sissy graduates are after hundreds of hours of cleaning and cooking and serving -- all under our most strict supervision, of course. There is intense training on etiquette, deportment, speaking, beauty and other skills expected of sissies (did anyone say massage?)  Training here includes classes led by my wonderful staff, supplemented with subliminal messaging and hypnosis.  We have also begun your son on medically supervised hormone treatment (you will recall signing a release for that.)                                                                                                 I did not share it with you in my prior letter, but we did have to use some rather extreme measures on your son during his first weeks with us.  But we know what we are doing in this area and we were able to get him to understand that he is to be obedient and submissive and cooperative -- or risk a repeat of the punishments he received when he first arrived.                                                                                                    Anyway, those days are behind us now and your lovely sissy son is making wonderful progress.    I will write again soon.  Sincerely, Mrs. Trainer."

 

A Reluctant Sissy -- Part 1 -- Arrival

It was just about two years ago that I finally decided that I had had enough!  I am a single mother and my son was completely out of control.  I didn't really care that he was a crossdressing sissy.  I didn't like him getting into my lingerie and make-up and dresses and shoes every time my back was turned.  But I could have lived with that.  There were other problems -- real problems.  He was close to failing out of school, he was getting into all sorts of drugs, and I was spending a fortune getting him out of trouble with the police for his non-stop shoplifting.

There were endless meetings with his teachers and counselors at school.  But they had no answers.  I tried family therapists, but they were useless.  I tried grounding him and every other form of punishment I could think of.  Nothing worked.

And then he stole several pieces of my jewelry and tried to pawn them. That was the last straw!

I remember reading somewhere that there was a Ms. Trainer who ran a service where she could improve the behavior of boys through feminization.  It wasn't easy to track her down, but I did.  I discussed my situation with her and she was very reassuring.  She explained that since my son was already a crossdressing sissy, her techniques should work very effectively on him.  She suggested that I send him to her new facility in London, where the staff and the process were extremely strict and effective.  A new semesters was just about to start and there was one opening (they handle up to six sissies at a time).  I considered this to be a real opportunity so I wasted no time at all in doing what she suggested.

Imagine my son's surprise when we arrived at Ms. Trainer's estate outside of London.  My son thought I had taken him to London so he could go pubbing and what not. You should have seen the look on his face when we pulled up the driveway and two enormous orderlies roughly grabbed him and dragged him out of the car and into the house!

After an initial period a six weeks, during which I had heard nothing about my son's progress, I received my first report from school -- complete with lots of photos!  Let me share their letter with you:

"Dear Mrs. ___, 

We are happy to report that your son has made good progress during his first six weeks with us.  We have decided to call him "Kimberly" -- we hope that name is satisfactory to you. He is settling into our routine of continuous training, behavior modification, and positive and negative reinforcement. There is evidence that we are starting to strip away his awful self-destructive behavior and replace it with a gentler, more compliant, feminized version of himself.  Enclosed please find several photos of how your son is dressed everyday here at the facility.  He really makes an adorable sissy!"

I stopped reading to marvel at the enclosed photos.  I was stunned by just how lovely my son looked in his pretty new dresses.  He had become so skinny in just a few weeks.  And his hair was dyed such a pretty shade of blonde.  His make-up, his jewelry, his sky-high heels -- everything was just so perfect and dainty and feminine.  I could barely believe my eyes.

The letter continued:

"Of course, even though we know he is a sissy at heart, he is resisting the feminization process.  This is normal and not a cause for concern at this early stage.  As you can see, he refuses to smile for our photos. As we remind him daily, we don't care if he is happy or not; he is only succeeding in making his transformation more difficult and more miserable for himself.

We will keep you posted as our time with your son proceeds.

Sincerely, Mrs. Trainer"

You Sissies Will Be Punished!

 

Mommy's Pajama Sissy -- Part 5

Well, I imagine you could already guess what might happen next. I couldn't stand having My Little Princess with me only when we were home alone and wearing our nightgowns. In early May I went out and bought Tammy some pretty dresses and shoes that he could wear out in public! 

There was a bit of nervousness at first, as you might expect. But the thrill of going out in public in a pretty dress was more than enough to motivate Tammy to summon enough courage to join me on some real-life adventures.                                                                                                                                           After several days of planning, we were all set for an exciting weekend together. Friday afternoon was very warm, so I dressed Tammy in a gauzy turquoise dress -- he looked simply lovely! Our Friday adventure started with a visit to the nail salon, where Tammy got his first mani-pedi. He was so nervous at first that his hands were shaking. But he settled down and his pretty soft pink nails looked divine. Then I took him to the mall where I let him pick out -- and try on -- several more new dresses and shoes and handbags. We went to three different department stores and must have been there for two hours! And of course I needed to buy him some bras and panties -- today he was borrowing my under garments but needed a collection of his own. Then we had dinner together at a restaurant where Tammy realized that he was getting some serious attention from our waiter!  Tammy handled it well and we had a simply wonderful time.

I had a busy Saturday planned for us. I dressed Tammy in an elegant royal blue silk dress. He looked stunning -- and so grown up! We had lunch together at an intimate cafe downtown that is very popular with ladies out for the day together. Then a matinee of a play at the Civic Auditorium. And finally, the highpoint of our day, we went to a fundraiser reception at the art museum.  Since alcohol would be served, the event was restricted to guests 21 and older -- which Tammy wasn't.  But I was so confident in his ability to appear like a grown-up lady and I knew this wouldn't be a problem. When the ticket taker asked the two of us for our IDs when we entered, I simply said to him "thanks for the compliment" and the two of us walked right on in to the event.  It was magical.  The museum was beautiful, the guests were all dressed up, there was a string quartet playing -- it was heaven! And I could see that My Little Princess was in heaven too.

Waiters passed glasses of champagne and little hors d'oeurves. About 45 minutes into the event we found ourselves near one of the bars where a young gentleman was chatting with a bartender.  I struck up a conversation with the handsome young man whose name was Steve. Steve looked very dapper in an expensive suit and tie. He seemed happy to have someone to talk to. He told us that he had recently finished business school and was home visiting his parent before starting a new job in New York with a big bank. He explained that his parents had bought tickets to the event, but were suddenly called out of town for the next few days. He was attending the event alone and didn't know anyone else there. Of course I introduced my lovely young Tammy to the handsome young Steve. Tammy had had several glasses of champagne by this time and was starting to loosen up a bit. It didn't take long for Steve to start flirting with his pretty new acquaintance. And it didn't take long for Tammy to play along and join in!

At one point Steve excused himself to use the restroom. "What a catch!" I said to Tammy. "Oh stop, Mother!" he replied. ""Don't be silly."

"I'm not being silly," I answered. "He's obviously smitten with you and I can tell you like him too." Tammy turned bright red when I said this. "Why not see where this goes. He's only in town for another two days. Then he's off to New York. Why not see what can happen before he leaves town..."

Tammy was initially dumbstruck by my suggestion.  But his internal feminine needs -- and the champagne -- pushed him to be bold enough to surrender to his urges.

"Alright, mother," Tammy said. "Let's see where this goes."

Mommy's Pajama Sissy -- Part 4

 As a cold winter gave way to spring, I knew it was time to start putting away our pretty flannel nightgowns. Although we had both enjoyed the coziness of our beautiful and feminine flannel gowns -- and the instant sensation of a slumber party that they evoked each time we put them on -- the nights were becoming warmer and it was time for a change.

Just in time for Tommy/Tammy's birthday in late March, I bought him two very pretty, very feminine lightweight nightgowns, one with little cap sleeves and another that was sleeveless.  And of course I bought the same spring nighties for me.

I thought my little Tammy was going to faint when he unwrapped first one and then the other. He held the soft fabric up to his cheek and positively beamed.

He took the cap sleeve nightgown upstairs and changed into it. He no longer needed my help doing his hair and make-up.  I had even put a small vanity table with a mirror and chair in his room so he would have a special place to make himself look pretty and to store his make-up and brushes and perfumes.

I thought he looked like a little princess in his pretty new nighties. I even started calling him "My Little Princess" when he was all dolled up.  I think he really liked it when I said that.

Something else happened that spring. In his pretty spring nightgowns, my little Tammy looked so grown up, so ladylike. I thought I might try exploring a new topic with My Little Princess...men.  I started very slowly and carefully. We started watching TV shows with more mature themes. These shows would often feature steamy love scenes -- and very handsome leading men. I would say things like "Ooh, isn't he handsome?" or "Look how strong and muscular he is," or "Mmmm, I think he's very exciting," as we watched our evening TV shows. 

After a little while I managed to get Tammy to engage me in conversation on the topic. He was, at least at first, a bit reluctant about voicing an opinion. But with a little bit of time and a bit of prompting from me, he was able to loosen up a bit and managed to admit to admiring the hunky men on the screen -- and sensing the thrill of the women that were in their arms. The more we watched and the more we talked, the more Tammy was able to imagine himself as the soft, feminine object of the male characters' desires. 

I knew that it caused Tammy some embarrassment to admit to identifying with the female characters in these romantic situations. But I explained to Tammy that it was perfectly natural for a young lady like him to have these feelings of excitement and desire for such masculine men. I explained to him that all girls want to be pursued by, and ultimately submit to, a real man.

I think my explanation confused and embarrassed my poor, sweet, little Tammy even more than he already was.  Oh well.  Maybe a few more pretty spring nighties would cheer him up, don't you think?

Mother's Pretty Little Sissy Daughter -- Part 2 -- Getting Ready for a Sissy Day

*** This is a continuation of a story from 2012.  To find Part 1, click on the "Sissy Jessica" Label in the right margin of the blog.  Enjoy! ***                                                                             As you already know, I have been pushing my son, Jesse, to embrace his feminine side.  In fact, I want him to become my daughter, Jessica, full-time.  Jesse is much too pretty to be a boy I think. And I tell him that almost every day.

I encourage my little Jesse to dress up as Jessica every chance he gets.  I do everything I can to get Jesse to think of himself as a girl.  I want him to let go of being a boy and to embrace a completely and permanent feminine existence.

Jesse still goes to school as a boy, but he spends all his time at home as a girl.  He has been living this way for almost six months.  He has become so naturally feminine that it has become unbearably painful for me when he reverts to being a boy.  And over that time, Jesse's hair has started to grow out long and beautiful and his body is slender and pretty as a result of the strict diet I keep him on.

As soon as he gets home from school and throughout the weekends, there is no sign of Jesse, only Jessica.

And because he spends so much time as Jessica, he has become very girlish and feminine. And he very talented at doing his hair and make-up.  Here are some photos I took of Jesse getting ready to spend a Saturday with me as mother and daughter.  He starts his day with a warm bubble bath, soaking in a tub where fragrant oils soften his skin. The experience relaxes and prepares his body and mind for a day of feminine fun.

After his bath he applies lotions to his skin before he begins to do his hair and make-up. Since he has been doing his own hair and make-up almost every day for several months, he has become a true expert at making himself look beautiful.   

I have a fun and exciting day planned for the two of us.  First, we will go to the big shopping mall that is about 20 minutes away.   We'll shop for dresses and lingerie at the big department stores.  Jessica always gets so nervous when I push him into a ladies dressing room to try on things.  Then we"ll head downtown for lunch at a restaurant we like. 

 I haven't told Jessica this yet, but there is a huge car show going on downtown.  The streets will be crowded with people and we'll probably have to park far away.  And of course the car show attracts men -- and teenage boys -- by the thousands.  So Jessica will get plenty of attention and admiring looks -- and comments, I expect -- from the men and boys we will be walking past.

Doesn't that sound like fun?

Now hurry along and finish getting ready, Jessica.  We have a busy day planned!

A Sissy Refresher -- Part 10

Sissy Erica returned to the living room wearing the sweetest little ensemble; a strapless lace and satin dress with a matching little bolero jacket.

"What a perfect little outfit for the trip home!" I said.

"Oh, yes," Ms. Trainer agreed.  "Doesn't he look lovely!  My assistants have been loading all of Erica's new outfits into your car.  The cargo area of your Escalade is completely full."

"That's fine," I replied. "We'll let Sissy Erica sit in the back seat instead of the cargo area, as usual."

"You drive," Roberto said to me. "I'm going to sit in back with Erica.  I need to have my dick sucked on the drive home.  I might want to fuck him too."

"That's fine dear," I replied.










"You will find everything you need has been loaded into your car," Ms. Trainer said. "All his pretty new dresses as well as his extra corsets.  In about four weeks he should be ready to squeeze into the next smaller size."  I could see Erica's face turn pale when Ms. Trainer said he would be wearing an even tighter corset soon!


"Well, Erica," Ms. Trainer said, "I hope you are going to be a good little sissy for your wife/mistress and her lover.  I expect you to apply everything you learned here this summer to being the best little sissy you can be."

"Yes, Ms. Trainer," Erica managed to reply.

"That's good, Erica.  I would expect nothing less from you.












"Now take off your little jacket," Ms. Trainer instructed. " I don't think you will be needing that for your ride home in the backseat with Roberto."  Erica took off the jacket as we once again gazed with amazement at how feminine and delicate Erica now appeared. Turning to Roberto, Ms. Trainer said, "Erica's tight little sissy-pussy has lubed up so he is ready to be fucked whenever you want."

Turning her attention back to Sissy Erica, Ms. Training said, "We will all miss you, Erica. You are a darling little sissy.  You are wonderfully obedient and pathetic." And with that Ms. Training gave Erica and deep, hard kiss on the lips.  Erica staggered from the experience of being kissed by Ms. Trainer, revealing just how extensively Sissy Erica had been broken, being erotically aroused by his tormentor.

Ms. Trainer continued. "Erica, I have been speaking with your owners and we've agreed that we will have you come back here for another 12 week Sissy Refresher course next summer!  Isn't that wonderful news!  We are already working on the new curriculum -- all sorts of new advanced sissy skills to teach you.  Isn't that exciting?"

I thought Erica was going to die when he heard this.  I added to the fun, "That's right, Erica.  Roberto and I are planning a long trip to Australia and New Zealand next summer so we decided that it would be best to bring you back here while we're gone.  Now answer Ms. Trainer, Erica.  She asked you if you were excited about coming back here for another 12 weeks of sissy training."

"Yes, Ms. Trainer.  I'm very excited about coming back for more sissy training," he barely managed to say.

"We are excited knowing that you will be back with us.  But for now, it is time for you to go and resume your duties caring for your wife/mistress and her lover."

"So hurry up and get in the car, sissy bitch," Roberto snarled.

And with that, Sissy Erica minced his way back to the car, returning to his life as a helpless, pathetic, feminized sissy toy for his wife and her lover.

A Sissy Refresher -- Part 9

Sissy Erica returned to the room, this time wearing a long strapless gown in ivory lace.  The dress was topped with a satin bolero jacket that matched the satin sash that wrapped around Erica's tiny, corseted waist.  Erica had dried the tears he had shed a few moments earlier when Ms. Trainer made him re-live the suffering and humiliation he endured from the other sissies over the summer.  The tears were gone, but the pain and confusion were still evident on his pretty, made-up face.

"Wow!" Roberto exclaimed as Erica sashayed across the room, modeling the elegant gown.

"Wow, indeed!" agreed Ms. Trainer.  "That is one fine looking sissy you have there."

As Erica modeled his beautiful new gown, Ms. Trainer spoke to Roberto and me, as if Erica wasn't even in the room.  I really love how she does that.  "So, I understand that you and Roberto will be having a Commitment Ceremony in the fall.  What a lovely idea."

Erica's head jerked around when Ms. Trainer said this. Obviously I had not mentioned anything about this to Erica.

"Oh yes, it's true.  Roberto and I are really excited about it. Of course I can't divorce Erica or I would risk losing control of his company and his assets. So Roberto and I can't get married.  But I thought it would be nice for us to have a Commitment Ceremony -- and a big party -- to celebrate our love for each other."  I gave Roberto a big kiss.

"How wonderful!" Ms. Trainer gushed.  "And this gown will be perfect for Sissy Erica to wear.  I assume Erica will play a big part in the ceremony."

"Oh yes," I replied. "Erica will be my 'Sissy of Honor,' supporting and serving me throughout the ceremony and the party.  I am also thinking about having Erica walk me down the aisle and 'giving me away' to Roberto."

"That's a wonderful idea -- I love it!" Ms. Trainer said with a laugh.

By this point Erica was shaking involuntarily.  The whole topic was simply overwhelming him.  But Ms. Trainer would not let up.  "And will you invite a lot of people?" she asked.



"I was thinking about one hundred.  While I've told all my friends -- and Erica's former friends and colleagues -- that he had been...embracing a sissy lifestyle, almost no one has seen him for several years.  So this party will also be a sort of coming out party for Erica."  I thought Erica was going to pass out at this point!

"Erica, sweetie," Ms. Trainer cooed, "Take off you little bolero and show us how you look without it."  Erica obediently did as he was told, exposing his soft, skinny shoulders. Just enough of his sweet  breasts were on display peaking out over the top of his gown.  "Oh Erica," Ms. Trainer said gently, "you look absolutely lovely.  Your wife/mistress will be so proud to have you serving her at her Commitment Ceremony."  Ms. Trainer's compliments tore through Erica like a knife.

Ms. Trainer continued. "I think it would be nice if, as part of the ceremony, you included a portion where Sissy Erica can make his vow to Roberto as well.  What I mean is after you and Roberto exchange your commitment vows to each other, it would be very touching if Sissy Erica would stand up and publicly state his own commitment of servitude and obedience to the new man in the relationship.  Erica could also make a public vow to you, as his former wife, to serve, honor, and obey you and to do everything in his power to ensure your happiness."

I was speechless.  This was the best idea I had ever heard of!  How marvelous it would be to have Sissy Erica publicly proclaim his commitment to his submissive sissy existence and to serving Roberto and me.

"I have another question for you," Ms. Trainer began.  "At your Commitment Ceremony and party, will Sissy Erica be on his own -- or will he have a date?"

"Well, I guess I never really though about that," I replied.  I guess I figured that Sissy Erica would be on his own."

"Well, I think it would be fun if Erica had be big hunky man for a 'date' on your big day.  You know, I big muscle-y man, pawing and groping at Erica all evening in front of your friends. It would be fantastic.  If you like the idea, I can find you the right man to be hanging all over Erica all night long."

"Oh, Ms. Trainer!  Your great ideas never end!"  I exclaimed.  "Please, find me a great big stud to be Sissy Erica's date for my Commitment Ceremony!"

"Well, I'm so glad we were able to enjoy this little fashion show and to share a little bit about Sissy Erica's exciting summer," Ms. Trainer said.  "But I sorry to say that it is time for us to say good-bye to Sissy Erica.  Darling," Ms. Trainer said to Erica, "Go and change into your last dress that you can wear for the trip home."

A Sissy Refresher -- Part 8

Sissy Erica returned to the living room, this time wearing a lovely dress in the palest imaginable shade of blue.  The full skirt ended in a pleats at the waist where pretty lace applique ran around Erica's tiny waist.  The dress was elegant and sexy at the same time, with a low cut neckline that revealed Erica's hormone and surgery enhanced cleavage.

"Oh my," I said as Erica modeled his latest dress.  "He is the epitome of ladylike elegance and femininity in that outfit."

"I agree," replied Ms. Trainer. "I think this dress suits our little Erica perfectly."

"Erica, did you make friends with the other little sissies that were here with you this summer?" I asked.

Sissy Erica didn't seem to know how to answer.  He looked over to Ms. Trainer for guidance or permission or something.

"Well now," Ms. Trainer answered for Sissy Erica.  "That is a very interesting question.  I am so glad you asked.  I'm sorry to report that Erica didn't do so well in making friends with the other sissy students this summer."

"Oh dear," I replied.  "Erica, whatever was your problem?"  I felt myself getting cross with Erica and wanting to punish him.  It was a good feeling after being away from him all summer.

Ms. Trainer explained.  "You see, we had a little fun at Sissy Erica's expense this summer.  Since he was the prettiest, most feminine and best trained sissy, we thought it would be fun to make the other sissies extra jealous of him."

I noticed Erica react to Ms. Trainer's words.  This was clearly new information he was hearing for the first time.

"Oh yes," Ms. Trainer continued.  "After a training exercise we would often compliment Erica on his performance and tell the other sissies that their performances were terrible.  We would threaten to punish the other sissies because they weren't as perfect as Erica.  We would also tell the other sissies that Erica was getting extra food because he was such a good sissy.  Sometimes, we even told the other sissies that Erica had tattled on them, and gotten them in trouble and subjected to more punishments."

"But I never did any of those things!" Erica blurted out.  "I never tattled and I never got extra food!  I never meant to make the other sissies mad at me!" He broke into tears as he spoke.

Ms. Trainer promptly slapped Erica hard across the face and screamed, "Sissies do not speak unless spoken to!  For God's sake, didn't you learn anything this summer.  Stupid sissy."  Ms. Trainer tore the little jacket off Erica's narrow shoulders and shouted, "Now just stand there -- SILENTLY -- while I finish speaking."  Her fury subsided and she continued, "Of course you didn't do those things, Erica, but the other sissies didn't know that, now did they?"

"Well anyway, the other sissies really resented Sissy Erica and that was great fun to watch.  Poor Erica was all alone in every sense this summer."

"What did the other sissies do to Erica?" I asked.

"You're going to love this," Ms. Trainer said.  At night, all our four of sissies would sleep together in one king size bed.  Wearing nothing but their corsets and curlers.  It's a very sexy, sensuous scene, as you might imagine.  Anyway, the other sissies would...take advantage of Erica at bedtime.  What the sissies didn't know is that we added a dose of ground up Viagra to the other sissies' dinner rations  So by the time they climbed into their shared bed with your gorgeous little Erica, their resentment and desire were both inflamed.  So they would take turns fucking little Erica here, two sissies holding Erica down while the third sissy pounded Erica's tight little ass."

Erica went into uncontrollable sobbing reliving the horrors of the past 12 weeks.

"And the best part is, we filmed this little rape scene every night!  I have hours and hours of hot, rough sissy sex action on tape starring Erica.  I have some friends who are editing it down.  They think we can get 8 or 10 hours of the best material and make some good money selling it on DVDs and the internet."

"Isn't that exciting, Erica?" I said. "You're going to be a movie star!"

A Sissy Refresher -- Part 7

"Now I don't know if you ever take Sissy Erica out with you in the evenings, but I think this dress would be perfect for a sissy night on the town," Ms. Trainer began as Erica re-entered the room, this time wearing a little black dress embellished with rhinestone around the neckline.  The dress was simple, classic -- but Erica still looked so damn sexy!

"Yes, sometimes we take Erica out with us, often when we have a male friend of Roberto's visiting from out of town.  It's fun for us to make it a double date, letting Erica be a real man's pretty date for the evening.  And yes, this dress would be perfect!  What man wouldn't love having a sexy escort like that!" Roberto heartily agreed.

Changing the subject, I asked, "So tell me, what is the diet you put the sissies on to get them so...svelte?"

"Erica, tell your wife/mistress what you ate while you were here."

Erica mumbled a response that I couldn't understand.

"Oh speak up, Erica, for God's sake! Nobody likes a mumbling sissy!"

"Baby food," Erica managed to say.

"What?" I exclaimed.  Barely able to contain my surprise and laughter.

"Oh, yes," Ms. Trainer explained.  "It's a wonderful way to control and minimize portions and calories and dignity.  One small jar, three times a day, will guarantee rapid weight and self-respect loss."

"No wonder he looks so slim and dainty," I remarked.

"Erica, sweetie," Ms. Trainer asked. "What else did you eat while you were here?"

Erica looked terrified.  "Nothing, Ms. Trainer.  I ate nothing else.  Only the food that I was given.  Honest."  Erica looked panicked, believing that he was being accused of an infraction of the rules.

"Don't get your panties in a twist, sweetie.  You're not in trouble.  I was just pointing out that you ate something besides baby food all summer."

Erica still looked confused and frightened.  "I was just pointing out, Erica," Ms. Trainer explained a bit impatiently, "that you also ate a lot of semen over the past twelve weeks.  And I mean a lot!  Isn't that true, Erica?"

Erica's fear instantly turned to intense shame.  "Yes, Ms. Trainer," came the pitiful response.  "I did eat a lot of semen."

"You see?" Ms. Trainer added.  "Our sissies get a perfectly balanced diet here!"  I almost fell on the floor laughing when she said that.

"Let's see another dress!" Ms. Trainer chirped.

A Sissy Refresher -- Part 6

Erica re-emerged from the other room, this time wearing a lovely silver dress with a matching chiffon bolero.  It accented his fabulous new figure superbly.  He looked so elegant and dainty.

"Ms. Trainer, please tell me more about the training Erica has received since he's been here," I inquired.

"Of course," Ms. Trainer replied.  "This is a brand new program for us and I am very pleased with how well it went in its first year."

She continued, "I developed a curriculum that would help advanced sissies, like Erica here, develop the skills they need to take their service and submission to you to the next level.  The course work covered three main areas: service skills, beauty and comportment, and sex techniques."  Roberto was suddenly interested in hearing more when the third item was mentioned.


"In the area of service, Erica has been learning wonderful new skills.  He can now perform a Swedish Massage on the two of you.  He has learned some interesting new breakfast in bed recipes and serving ideas.  And he has learned important new skills to help you plan and hostess and serve when you are entertaining.  Isn't that all correct, Erica?"

"Yes, Ms. Trainer," came the soft reply. "That is all correct."

"Erica, take off the little jacket while I continue," Ms. Trainer instructed.

"Yes, Ms Trainer," Erica said as he complied.

"Where was I?  Oh yes, beauty and comportment.  Well this whole decorative sissy thing requires some new skills for our sissies, like making themselves as pretty as possible and posing for hours like a mannequin..."

"Or a Barbie," Roberto interjected.  We all laughed.

"And he can do his own hair.  Isn't it lovely?  It's very difficult to make it look so nice, but Erica has been a very good sissy student.  Of course he has to sleep in his curlers, which is very uncomfortable, but it's all worth it."

Ms. Trainer continued.  "In the sex department, well that's where things got the most interesting.  Wouldn't you agree, Erica?"

"Yes, Ms. Trainer," came the timid and shameful reply.



"Our little Erica here has developed some impressive new skills.  We did lots of fellatio practice over the past twelve weeks. Erica can now accept the biggest imaginable cock down his throat.  We also had a pussy worship course -- I taught that one myself.  And I'm pleased to report that Erica has a very, very talented tongue.  You will be very pleased.  We also practiced some group sex.  Erica learned to take two dicks up his ass and two more in his mouth, all at the same time!  Erica, how much is two dicks plus two dicks?" Ms. Trainer asked in her speaking-to-a-child voice.

"Four dicks, Ms. Trainer," came the pitiful reply.

"Oh my, Erica!  Did you pleasure four men at once?  Why what a little whore you are!"

We burst into laughter once again.

"Go change, Erica," Ms. Trainer instructed.