A Reluctant Sissy -- Part 8 -- A Letter to Mrs. Trainer

It had been about a month since Kimberly was returned home to me and I decided to write a letter to Mrs. Trainer.

"Dear Mrs. Trainer, 

I can't believe it has already been four weeks since my Kimberly was returned to me.  I can not thank you enough for the dramatic improvements you made to my son's attitude and behavior.  I am so happy to report that he has been an absolute DELIGHT since I picked him up at the airport.

Let me fill you in on some details.

When Kimberly arrived at the International Terminal, he was dressed just as you had promised -- in that adorable cream colored two piece outfit with the belted top and the pleated skirt. And those beautiful high heeled shoes.  If you hadn't prepared me by sending the photo to be ahead of time, I would have fainted seeing how beautiful he looked!  Anyway, as he stepped off the gateway, he walked right up to me, eyes pointed down to my shoes, and he curtsied!  He actually curtsied to me right there in the airport!  He thanked me for sending him to your school and promised that he would never disappoint or disobey me ever again.  I told him that a new life awaited for him at home and off we went.                                                                                  When we arrived home, I showed him to his room which had been completely redecorated since he left.  There was no trace of his past life.  All the furniture was white and there were lacy curtains over the windows. The drawers and closets were already full of his lingerie and dresses and shoes and all the lovely outfits you had shipped to me before he arrived. And of course there was a vanity table and mirror for him to do his hair and make-up.

As you suggested, I wasted no time getting Kimberly introduced to his new schedule and responsibilities.  He is so wonderful at following directions -- I only have to tell him to do things once and he immediately gets busy fulfilling my every need.  Of course that includes all the cooking and cleaning.  But I also have him bathe me every evening -- that was quite an experience the first time for both of us!  I'm sure others would find it quite shocking for me to be naked and bathed by my former son.  But there is nothing sexual about it.  I know it sends a powerful message about who is in charge and who is subservient. 

Also, per your instructions, I arranged for Kimberly to "make amends" for all the past trouble he had caused and believe me, that was a very long list indeed.  I had Kimberly dress in the outfit pictured here.  I know he hated it but he said nothing.  Just look it him!  That dress is ridiculous -- and just perfect for what I had planned.                                                                             About two weeks ago, I had Kimberly put on this outfit.  He knew something was up as soon as he put it on!  And off we went to downtown.  I made a list of every store that he had shoplifted from and we went to each one.  Kimberly went in, curtseyed to the manager and asked for forgiveness for is past misbehavior.  People in the store watching this couldn't believe their eyes.  Most had no idea what they were witnessing -- this absurdly dressed young women, fighting back tears as she (he) begged for forgiveness!  It was wonderful!.

But the best part came next.  After visiting about a dozen stores downtown and several more at the mall -- we went to the high school next!  As you said, there is no reason for Kimberly to ever return to school -- he learned everything he will ever need to know at your training academy.  But Kimberly needed to make amends to many teachers and administrators at the school for all the trouble he had caused.  So there we were -- for a couple of hours.  Walking the hallways, going room to room, office to office, curtseying and apologizing to every teacher and every administrator that had been subject to his misbehavior.  And of course, only a million of his classmates saw him as we walked through the busy hallways.  There were many giggles, much pointing and quite a few "salty" comments from some of his former classmates.  Well that experience was traumatic for Kimberly to say the least.  He was in tears before we were even half through our rounds!

Anyway, life is wonderful with my new and improved Kimberly.  Thank you for saving him and returning him to me.  It was for the best -- especially for him.

Yours,   Mrs. _________"

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 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 3 -- Sissies go to Church

It had only been a week since my last letter when I received another update from Mrs. Trainer on my sissy son's progress at Mrs. Trainer's "transformation" academy

"Dear Mrs. _____, 

All of our sissies, including your pretty son, continue to make wonderful progress.  Of course, there are challenges to overcome, but nobody said it would be easy!

There is so much activity here at the academy every day and every week.  I know you never had the opportunity to attend our full orientation program for sissy guardians and owners, so I hope my letters will help you get a full picture of all the fun we are having here (well, fun for us. Not so much fun for the sissies!  Ha ha!)

One lovely tradition we have is that we take all of our sissies to church every Sunday.  The vicar of our local church is quite the pervert and he enjoys getting to know each of our sissy students.  Every week, our sissies get all dolled up in their Sunday finest and we parade them into church, where they all sit in first pew, their dresses and make-up and posture simply perfect."

I marveled at the photos Mrs. Trainer sent of my son wearing these adorable, conservative -- but very stylish -- outfits.  The idea of Mrs. Trainer's staff forcing my son into these clothes and then taking him out in public gave me an unexpected shock of excitement. He's even wearing gloves in one photo!  And I simply love the oversized pearl jewelry they have him wearing.  

And there was that same sad/mad face.  I knew that attending Mrs. Trainer's academy must be torture -- but I also knew that it was for the best.  Besides, he brought it on himself!

I returned to Mrs. Trainer's letter.

"Part of what makes taking our little sissies to church so fun is that the congregation has no idea these are naughty boys all dolled up and in the process of being transformed.  As far as the other churchgoers know, these "ladies" are attending a "finishing school" that I run.  And the best part is, while our little sissies serve coffee and cake after the service, all the church ladies make such a fuss over them saying things like, "How I wish my daughter would act and dress like such a perfect lady," or "I wish my son in London could meet a nice young lady like you."  This attention makes our little sissies absolutely squirm! For the staff at our school, it is one of the high points of our week.

I mentioned that our local vicar takes a very keen interest in our sissies.  He is an obese old man who visits our school several times a week to meet with our sissies one-on-one for  "spiritual development" counseling.  This always seems to involve our sissies enduring a lot of severe over the knee spanking.  And I'm not sure that there is a lot of praying going on, but our sissies seem to spend a lot of time on their knees when they're with him (wink, wink!)

Rest assured, we are doing a very thorough job on your son.  Don't let that insubordinate sneer on his face worry you; your son is stubborn but I promise he will be as meek and gentle as a baby kitten when he returns to you.

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."

 

Mommy's Pajama Sissy -- Part 3

By the time Christmas arrived, Tommy and I had been sharing my collection of pretty ladies pajamas for several weeks.  He had wore every set I own at least a few times.  I thought Tommy would enjoy something new.

On Christmas Eve, it is our tradition to open one gift each, saving the rest for Christmas morning.  This year, I had picked out a very special Christmas Eve gift for Tommy to open.

When Tommy opened his gift, he was almost overcome with joy.  Inside was a pretty blue flannel nightgown of his very own.  "Oh Mommy!  I love it!  Can I put it on now?"

"Of course sweetheart," I replied.  And when Tommy returned downstairs in his pretty new nightie, he had a second surprise.  I was wearing the exact same nightie.  "Surprise, sweetheart!  Now we're twins!"  Tommy ran up and hugged me.  He told me he loved me.

I fixed his hair and put a little lipstick and blush on him.  I added just a spritz of the flowery perfume he liked so much.  He was simply lovely in his pretty new nightgown.

We spent all Christmas Eve -- and most of Christmas Day together wearing our matching nightgowns.  And we had a wonderful on Christmas afternoon snuggled up together on the couch under a warm quilt watching chick flicks on TV.  My sweet Tommy cried during "The Notebook."

Over the next few weeks I bought Tommy -- or as I was now calling him -- Tammy -- and me several more pretty matching nightgowns to get us through the cold winter together. 

Mommy's Pajama Sissy - Part 2

When Tommy returned home from school the next afternoon, the first words out of his mouth were, "Mommy, can I dress up in your pretty pajamas?"

I will admit that I was surprised by how anxious and excited Tommy appeared to be to repeat last night's experience.

I told Tommy I would let him wear my pretty pjs as soon as he was done with his homework. Well, Tommy tore into his homework with a vigor I had never seen before.  After about an hour and a half, he announced that he was done.  I took him up to my bedroom where we picked out a light blue floral print set for him to wear.  I again sat him down at my vanity and fixed his hair and put a little make-up and perfume on him.  "There," I announced when I was done.  "Now you look and smell pretty."  He beamed when I said that.

He moved from the vanity to my full-length mirror, where for stood for nearly ten minutes, as he turned and struck various poses, mesmerized by his own girlish reflection.

I changed into my pajamas and we ate dinner together.  He chatted happily about his day -- something that he hadn't done with me for ages. Afterwards he helped me do the dishes without even being asked.  We watched tv together and generally had a wonderful time.

Our pajama fun continued every night. Each evening I would pick out a set of my pretty pajamas for Tommy and each evening he would race through his homework so that he change out of his boy clothes and into my ladies pajamas.  Over the course of that first week, I let him wear a pretty white set with red flowers, a black set with pick flowers, and a very sweet powder blue set.

Of course I knew this was a bit unusual, but it seemed to make him so happy.  And it also brought us much closer together.  He was so engaged and affectionate when he was wearing my pretty pajamas. I soon realized I was enjoying Tommy's unusual fixation with looking and feeling feminine as much as he was.

Mommy's Pajama Sissy -- Part 1

Last fall, shortly before Halloween, the weather turned suddenly very cold.  Our house is rather drafty so I wanted to be sure that my teenage son Tommy stayed warm.  But I then discovered that, over the summer, he had outgrown all of his winter pajamas.  Since Tommy and I were about the same size, I suggested to Tommy that he borrow a pair of my flannel pjs.  I handed Tommy a set that was white with a pale blue floral print.  I thought he might protest, but he didn't.

When Tommy emerged from his room wearing my pajamas, I could tell that his mood had brightened.  He went into my bedroom and stood in front of the big mirror, admiring his reflection. "Do you like those pjs, Tommy?"  I asked.

"Oh yes, Mommy.  I do.  I think they are very pretty," he said.  "Mommy," he continued hesitantly, "Do you think I'm pretty?"

"Pretty?" I responded with surprise.  "Well, I never thought about it, but yes, I suppose you are pretty."

He smiled.  "I want to be pretty.  Pretty like you," he said, still gazing at his reflection.

I was puzzled but also very touched by what he said.  "Well, maybe I can help you to be even prettier," I suggested.  I sat Tommy down at my vanity and started to brush out his hair.  His curly, dirty blonde hair hung down nearly to his shoulders.  As a boy, his long hair gave him a wild, surfer dude look.  But as I brushed it I realized just how pretty his hair was.  I gathered up some of his hair and pinned it up in back.  I brushed out a few tendrils and let them fall to the sides of his face.  I dabbed some pink gloss on his lips and brushed a little blush on his cheeks.  When I asked him if he wanted me to spritz him with a little cologne, he said, "Yes please, Mommy."

Tommy and I proceeded to spend a delightful evening together, both of us wearing pretty flannel pjs.  We snuggled up together under a blanket on the couch and watched tv together, something we hadn't done since Tommy was just a little boy.

That night, I even tucked Tommy into his bed.  He did indeed look very pretty, with his lips and cheeks pinked with my make-up and his brushed out hair falling across the pillows.  I kissed him good night on the forehead and he said, "Thank you Mommy."

As I turned off his light and closed the door to his bedroom, I wondered if this was going to prove to be a one-time event.  I suspected it would not be.

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 Pretty Little Sissy for Ms. Jones -- Part 2

"Good," said Ms. Jones with a satisfied smile. "Because I want us to become very special friends." And with that she took of the blouse and skirt she had been wearing and stood in front of Veronica in just her bra and panties. Sissy Veronica's eyes nearly popped out of his head having never seen a woman undressed in real life, let alone a sexy, curvy goddess like Ms. Jones.

"Now tell me, Veronica, tell me that you want to be a beautiful woman like me.  Say it!"

"Oh, yes, Ms. Jones, I want to be a beautiful woman just like you!"  Ms. Jones smiled with great satisfaction.

"Now come here, Veronica," Ms. Jones instructed.  She wrapped her arms around the sissy's narrow shoulders and pulled him close to her enormous breasts.  She kissed him hard on the lips and let her hands start to explore Veronica's skinny, smooth body.

"Now, Veronica, I want you to start kissing me all over my body," Ms. Jones instructed and sissy Veronica did as he was told, starting at Ms. Jones' neck and working his way down to her breasts, her belly and beyond.

As Ms. Jones looked into her new sissy plaything's eyes, she thought about all the fun they would have together.  She thought about how exciting it will be to attack her sweet young thing with an enormous strap-on dildo, taking Veronica's sissy virginity away from him.  She thought about how much fun it will be to invite her friends over -- men and women -- and to share her sissy plaything with them.  She started thinking about having a couple of giant studs spit-roast the little sissy -- one dick in his mouth, the other up his sissy pussy -- while she filmed it for the internet.  That thought made her pussy very wet!

"Now, Veronica, you have to understand that your are a sissy and that you now belong to me.  That means you have to do everything I tell you to do, without question or hesitation.  Do you understand me?"

"Yes, Ms. Jones, I understand," Sissy Veronica softly replied.

"What do you understand, sissy?"

"That I am your sissy and that I now belong to you.  And that I must do everything you tell me to do," the sissy repeated back.







"Good, sissy," Ms. Jones replied.  "Now take off your bra and panties and put on this condom.  I am going to let you fuck me with your itty-bitty sissy-dickie-wickie."  Ms. Jones laughed.

Sissy Veronica stripped as ordered and put on the condom.  Ms. Jones instructed him exactly what she wanted him to do to bring her pleasure.  And he did it.  She had the most explosive and satisfying orgasm she had had in years.  Sissy Veronica came as well, of course.  It was the most exciting moment of his life.





"Remove the condom very carefully, sissy, and hand it to me.  Now close your eyes, tilt your head back and open your mouth."  Sissy Veronica did as ordered without question.  And as he did, Ms. Jones emptied the contents of the condom into the sissy's open mouth, squeezing every last drop of sissy cum out onto Veronica's tongue.  "That's a good sissy," Ms. Jones breathed. "Swallow it all, every drop.  Sissies have to eat cum every day, so get used to it.  Some days it will be your cum, but many days it will be another man's cum."







Ms. Jones handed Sissy Veronica the white bra and panty he had been wearing earlier.  "Put these back on and wear them under your clothes tonight and at school tomorrow.  You better be wearing them when you come to my house immediately after school.   Do you understand?"

Sissy Veronica put on the bra and panties and got dressed to go home.  "Yes, Ms. Jones.  I understand completely."

A Pretty Little Sissy for Ms. Jones -- Part 1

This is Ms. Jones. She is a forty-ish divorcee with an incredible body and some pretty kinky ideas. While she dates a lot of men, she rarely feels satisfied with conventional relationships. She's tried being with other women and with groups -- but nothing has ever really felt completely fulfilling. That all changed when she got to know Vernon, the boy who lives next door.

Ms. Jones and Vernon have a secret that they share. Actually they have several secrets. One secret is that Vernon is a little sissy fairy who loves to dress up and act like a girl. The other secret is that Ms. Jones has turned sissy Vernon into her feminized love toy.

Ms. Jones had known for some time that Vernon was a little sissy. She had discovered that Vernon was accidentally using the Wi-Fi signal from her house to access the internet. With a little help she was able to monitor the internet sites Vernon visited and even read his emails and blog posts! Well, Ms. Jones learned that Vernon was into some wild stuff. Little Vernon was visiting a bunch of hardcore tranny sites -- including this blog! -- and was exchanging emails with some other sissies and admirers. Thinking that all his internet activity was anonymous, Vernon wrote long emails and posts about how he loved dressing up like a girl, how he longed for someone to turn him into a woman with large breasts, and on and on.

Ms. Jones found it very exciting to be the only person in the world who knew Vernon's secret. She would sometimes subconsciously touch herself as she spied on her little sissy neighbor's internet antics. Over time she found herself thinking about Vernon obsessively, finding the idea of a girly-sissy boy arousing. She decided to take action.

One day when Vernon was taking the garbage cans out and was all alone, Ms. Jones approached him. "Vernon, I have something very important to talk to you about. But I am only going to say this once so listen carefully. I know you are a little sissy crossdresser." Vernon was about to say something to try to deny it but Ms. Jones would have none of it. "Shut up!" she snarled sharply, causing Vernon to jump. "I told you to listen to me and I meant it!" she said in a growling, commanding way. "I know you are a sissy faggot and that's OK with me. I don't plan on telling your mother or anyone -- if you do what I ask of you. Do I have your attention?"

Vernon nodded meekly. Ms. Jones noted with satisfaction how easy it was to dominate him with just a few strong words. She also noted that even dressed as a boy he looked rather girlish, his long brown hair hanging over his rather delicate features.

"Now, I think you are going to like my proposal. Starting tomorrow, you are to come over to my house everyday after school as well as on weekends. I have plenty of girly clothes and make-up and everything you need to have your little sissy fun. I will even help you. How does that sound?"

She already knew the answer. Even though it was hard for him to admit it, the offer was like a dream come true.

The next afternoon Vernon came over to Ms. Jones house as she had instructed. She greeted him with a big hug and brought Vernon up to her bedroom where she had him undress completely, right in front of her. Ms. Jones laughed when she saw how tiny Vernon's little dickie was. Vernon was so embarrassed but completely powerless to do anything other than accept the humiliation he was experiencing.










Ms. Jones reached into a dresser and pulled out a a very pretty white bra and panty set. She explained to Vernon that this underwear belonged to one her girl lovers who was just about the same size as Vernon. She helped Vernon pull on the panties and to tuck his tiny dickie. She then fastened the bra behind his back. "Vernon," she explained, "you are going to have to learn to do this all by yourself." She then brushed out his hair and put some make-up on him. She slipped a pair of sexy, strappy black heels onto his feet. She told him to lie back on her bed as she started to take photos of him. "Do you like this, Ver..." she hesitated. "Do you like this, Veronica?" she asked. 

"Oh, yes, Ms. Jones. Very much," he replied breathlessly.

"Do you like dressing like a girl, Veronica? Are you a little fairy sissy? Well, are you?"

"Yes, Ms. Jones," he replied. "I am a little sissy fairy and I like dressing like a girl."

"Good girl, Veronica," Ms. Jones cooed. "We are going to have a wonderful time together."

As Ms. Jones continued to snap photos of sissy Veronica in his pretty white bra and panties, she asked, "Do you like me?"

"Um, yes. Of course I do," he replied.

"And do you think I'm pretty, Veronica?" she continued.

"Oh yes, Ms. Jones. I think you are beautiful. I think you are the most beautiful woman I have ever seen."

"And do you wish you could have great big, soft titties, and a pussy, like I have, Veronica?"









"Oh, yes, Ms. Jones. Yes," Vernon panted.

"Good," said Ms. Jones with a satisfied smile. "Because I want us to become very special friends." And with that she took of the blouse and skirt she had been wearing and stood in front of sissy Veronica in just her bra and panties.

Sissy Priscilla Part 3 -- Mother's Wedding Surprise

After I had taken about a million photos of my beautiful sissy son bride, I told him that we should head back inside.  I could tell he was sad when I said that, sensing that our bridal fantasy day was wrapping up.  But I had other ideas.  In fact, the fun might be just beginning!

As I said earlier, sissies have such limited lives -- no friends, no romance.  But I knew I could change that.

You see, at the same time that I was making arrangements to rent the cottage and buy flowers for today, I had also gone online to see if I might be able to find a fantasy "groom" to make Priscilla's wedding fantasy complete.  There are plenty of websites out there for men looking to meet sissies. My challenge was to find the right one.  I posted some details of what I was planning for my little sissy and, needless to say, I got hundreds of responses from horny men wanting to have some dirty action with my sweet sissy son.  But one profile stood out from all the others -- a young, tall, handsome man, clearly well educated.  He seemed to understand what I was looking for in a "dream date" for Priscilla.  I arranged to meet him in person and I liked him immediately. His name was Kurt. 

So on the day of Priscilla's wedding, while Priscilla and I were taking photo's outside, Kurt arrived at the cottage and waited patiently for us inside. When he saw us starting to walk back toward the cottage, that was his signal to come out.  Little Priscilla was so frightened and worried when this tall man walked out of our cottage and started walking straight towards us.  "Now, now, Priscilla," I reassured. "Don't be frightened.  In fact I know this man.  His name is Kurt and I invited him."

Priscilla looked so confused and scared.  Kurt confidently strode up to Priscilla.  "Hello, Priscilla," he said.  "I am Kurt.  Your groom.  Your husband.  For today." 

Well, it took some time for Priscilla to compose himself after much reassurance from me. "Come, come, Priscilla," I said.  "Play along.  This is all part of making today's fantasy complete."  After a while, Priscilla relaxed, mostly because Kurt was so charming and gentle with him.  Before too much longer, I was able to get Priscilla to smile and pose for some photos with Kurt.  Here's the first photo I took.


Well, after the first photo was done, I was able to take about two hundred more as I asked them to pose in various locations around the pond.  With each passing moment, Priscilla became more relaxed around Kurt and seemed to ease more naturally into his role as the petite bride to Kurt's manly groom.

"Now a kiss!" I shouted.  Priscilla was shocked when I said this.  Kurt wisely went in for a gentle peck on Priscilla's forehead.

"Oh that won't do at all!" I cried.  It's time for a real kiss."  And I guess Priscilla agreed.












Kurt pulled Priscilla hard against him as Priscilla closed his eyes and allowed Kurt to kiss him for a very, very long time. I was delighted to see my little sissy son experience romance for the first time in his life.  I took dozens of photos of this lovely embrace.



We went back inside the cottage where I insisted that Kurt and Priscilla act out a wedding ceremony while I took even more photos.  I had arranged for some wedding flowers for the living room to set the mood.  

"Do you, Kurt, take Priscilla to be your wife?" I intoned.  "I do!" said Kurt while Priscilla beamed.


"And do you, Priscilla, take Kurt to be your husband?"  "Oh yes, I do!" replied my eager and delighted sissy son.  "You may kiss the bride." I instructed Kurt.  And Kurt did as I told him, scooping Priscilla up in his arms and kissing his lovely bride.



















"And now for your first dance as husband and wife!" I shouted and pressed play on the CD player.  John Legend's "All of Me" began to play.  Kurt expertly led Priscilla around the living room in a gentle, slow, romantic dance.  As the song came to an end, I decided it was time for me to make my exit.  "Well, three's a crowd," I said.  There's a light dinner and a bottle of champagne for you two in the refrigerator.  I will be up in my room.  Have fun.  And congratulations!"  Priscilla giggled as I left.


At about 6:30 the next morning I heard Kurt leave the cottage and drive off in his car.  I came downstairs and found Priscilla, in his vintage peach peignoir set, sipping on a cup of coffee, looking rather disheveled -- and a bit embarrassed.

"Well, well, well," I said. "And how is the new bride this morning?"

Priscilla waited a moment, finally answering, "A bit sore, actually."  We both broke out in laughter when he said that.  I gave my sissy bride son a great big hug.  

"I hope you enjoyed your wedding fantasy, darling," I said.

"Oh yes mother.  That was the most wonderful day -- and night of my life."

Kurt continued to be a frequent visitor at our home after Priscilla's sissy wedding.  But those are stories for another time.