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 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 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."

 

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"

Mommy's Pajama Sissy -- Part 12 -- The Conclusion

It turns out that Jimmy told Tammy that, as Captain of the football team, he was expected to "share" his girlfriend with some of the other seniors who were on the team.  This is what I overheard Tammy talking about on the phone.  Well, I couldn't believe what I was hearing, but it seems like my sweet, innocent Tammy was going to listen to whatever Jimmy said -- and do whatever Jimmy asked.

The very next day, I heard that Jimmy and Tammy went to the beach -- along with Jimmy's teammate Marcus.  Tammy didn't share any of the details of what happened at the beach but he seemed completely fine with whatever did happen.  I guess Tammy enjoyed the extra attention of two boys instead of just one.  

I soon had the impression that Tammy's dates with Jimmy usually included one -- or more! -- of Jimmy's football buddies.  I began to become concerned that Tammy was letting himself get caught up in something that wasn't very healthy for a young lady like Tammy.  But as unhappy as I was that Tammy was being "shared" among the players on the football team, I soon learned that the situation was perhaps even much more worrisome than I knew.

Tammy had been very open with me about his early experiences with Jimmy, but as the summer wore on, Tammy became much less willing to fill me in on the details of what he was doing.  I started checking his phone when I could just to get an idea of what he was up to.  So you can imagine my shock when I found these photos on his phone.  Because that's not Jimmy that Tammy is kissing.  That's Jimmy's Uncle Mike who owns the garage where Jimmy works!  Mike is in his mid-40's and shouldn't be romancing an innocent teenager like my Tammy!

And not only was Jimmy "sharing" Tammy with his Uncle Mike -- but apparently, Uncle Mike was "sharing" Tammy with his friends too!  The photos on Tammy's phone weren't very clear so maybe I'm not exactly sure what I'm looking at. Maybe you can figure out what's really happening here...

Oh dear! Perhaps this is all my fault!  It was just so much fun when we started wearing cute pajamas and nightgowns together  I could never have imagined that it would lead to this.

Mommy's Pajama Sissy -- Part 11

After the success of PJ Day -- and Tammy's "coming out" -- Tammy was on his way to having a very exciting summer.  In fact, I don't think I can remember seeing "Tommy" all summer long.

As the summer began, Tammy took a lot of interest in how he looked, asking me to take him to my salon every week so he could have his hair styled and colored in different ways. One week he'd ask for his hair to be straight and sleek and lightened; the next he'd want some curls back and a different shade of blonde. By now, Tammy's hair had really grown quite long so the stylist was able to make it look really great.  And Tammy started wearing more make-up -- which he had really never done before. 

And then there were the clothes!  I spent a fortune during the weeks after school ended to get Tammy all the different outfits he said he needed. Here are a couple of photos I took of Tammy after one of our trips to the mall.  Doesn't he look adorable.  You can see how he had his hair lightened.  And look at his eye make-up.  So pretty!  And check out those sexy sandals -- I wouldn't even be able to walk in those!

Right from the start, Tammy's schedule that summer was busy! The girls from his class started including him in their trips to the mall and hanging out at each other's homes.  Tammy would come home after spending time with the girls and tell me all about what they did -- and what they talked about -- which seemed to only BOYS, BOYS, BOYS!  And Tammy got his share of teasing from the girls because of Jimmy.  More on that in a minute!

One of the girls even got Tammy a job waitressing during the busy lunch time shift at the local diner.  I know this was hard work, but Tammy seemed to really enjoy it.  And I was glad that he was working during the summer -- even if just for a few hours a day.  Tammy looked so cute in the apron he wore when he was working. And every time I stopped by, Tammy was always getting a lot of extra attention (and some very good tips!) from the male customers.  

Well, back to Jimmy.  I had never dreamed that PJ Day would lead to Tammy catching the eye of the captain of the football team!  It was clear from the beginning that Jimmy was completely smitten with my little Tammy!  Some days, Tammy would get off work in the afternoon and go straight over to Jimmy's uncle's body shop and hang out there until Jimmy finished work.  And Jimmy was always asking Tammy to go out with him in the evenings and on weekends.  It all seemed innocent enough -- at least at first.  Tammy was thrilled with all the attention he was getting from Jimmy and how all the other girls from school were amazed that Jimmy and Tammy were "an item."  I had never seem Tammy so excited and happy as the times I saw him getting ready for a date with Jimmy.  He would spend hours getting himself all dolled up to look his nicest for his new boyfriend.  Sometimes he would try on dozens of outfits before settling on the one he would wear out with his new beau.

And Jimmy and Tammy did seem to have fun together.  Here are a few photos Tammy showed me of their time at the fair.  Just look how happy my little Tammy is.  And doesn't he look sweet in that little sundress he's wearing?  Jimmy certain seems to like what he sees!

 

The two of them spent a LOT of time together as the summer began.  There were dates to the movies and concerts, and trips into the city and lots of time on the beach. They really seemed to enjoy each other's company and seemed to be growing very close.

I know that the two of them would sneak off to be...romantic...together every chance they got.  My Tammy didn't even try very hard to hide it from me.  In fact, he loved talking about how being with Jimmy made him feel, how he loved being held tightly in Jimmy's strong arms, how he loved it when Jimmy would kiss him really hard.  But even if things seemed to be getting a little hot and heavy between them, I figured that they were just kids being kids and the experience of being together and exploring these romantic feelings wouldn't cause any harm.  And Jimmy seemed like a nice enough boy.  So I basically stayed out of it and let Tammy find his own way through this new terrain.

I was fine with all of it, really, until I overheard Tammy talking to one of his new girlfriends from school about something Jimmy called "sharing."

Mommy's Pajama Sissy -- Part 10

When I picked Tammy up from school, he was all smiles.  "Well, how did it go at school?  How did people react to seeing you as Tammy -- and in a nightgown?"

"It went great!" Tammy practically shouted.  "Of course, when I first arrived, I got a lot of stares walking down the hall to homeroom. But mostly I think people were staring because they didn't know who I was -- or why someone was wearing such a fancy nightgown to PJ Day!"

Tammy continued. "When I first got to homeroom, people were shocked.  I mean speechless. I thought it was hysterical!  But after just a few minutes, a bunch of the girls -- the cool girls, the ones that never talk to me -- came over and started fussing all over me. They were saying how pretty I was, how jealous they were, and so on.  It was totally fun!"

"It was sort of funny," Tammy continued, "That I was the one wearing the prettiest nightgown! Most of the other girls were wearing pajamas or flannel nightgowns -- like the ones we wear together in the winter. Nobody was wearing a fancy, pretty nightgown like me."  I was relieved to hear this as I thought Tammy's selection of nightgown wasn't exactly appropriate and I thought it might cause a problem -- but apparently not.

Tammy continued, talking a mile a minute. "But of course, the boys noticed me too.  A bunch of them just couldn't stop staring at me while I was chatting with the cool girls.  And then a couple of brave ones came up to me.  At first I was worried that they were going to give me a hard time or start calling me names.  But that didn't happen. Instead Jimmy Michaels came up to me a said 'Wow, you really look amazing. I barely recognized you.'"

I was shocked to hear this because I was aware that Jimmy Michaels (who was captain of the football team, by the way) had never been nice to Tommy over the years, calling him names like "sissy" and "faggot" just because he didn't like to play sports and because he mostly kept to himself.

"Well, after homeroom, we all went to the auditorium for the end of year presentation. The girls from my homeroom asked me to sit with them, and we were joined by the cool girls from the other homerooms.  And everybody was super nice to me and made a big deal about how pretty I looked." Tammy was practically breathless from talking so fast.

"Then after the presentations, we all went to the gym where they handed out yearbooks.  And they had pizza and soda and everybody spent the rest of the day signing each others' yearbooks and chatting and eating.  This time Jimmy Michaels came up and talked to me, even offering to get me some pizza and soda. He told me that he would working all summer at his uncle's car shop on North Street and he said that he hoped that we would get to hang out together over the summer..."

"The whole day went by in a flash. Before I knew it, it was time to go home."

"Well, young lady, you certainly had an exciting day!" I said. "You must be exhausted."

"Oh, I guess. But I'm supposed to meet some of the other girls at the mall at 3:00.  Can you drive me?  And tonight, Jimmy invited me to go with him to end of year bonfire down by the lake -- can I go to that too?"

"Well, I don't see why not. If it's what you want to do," I said.

Tammy's life experienced a big change as a result of his wearing a pretty nightgown to PJ Day.  That whole summer was a whirlwind of parties and days at the lake and afternoons at the mall and nights at the movies. Needless to say, I had to spend quite a bit of money on getting Tammy all the clothes that he needed now -- casual outfits and jeans and tank tops; swimsuits and cover-ups; party dresses; the works!

Mommy's Pajama Sissy -- Part 9

Tammy never shared with me all the details of his date with Steve. But it was very clear to me that Tammy had had an amazingly romantic and passionate evening.

But now Steve was gone, having moved to New York, and I could tell My Little Princess missed him, even though they had only been together on one exciting date.  But the last day of school was fast approaching and that was something good to look forward to.

At Tommy's high school, they have a fun tradition where the graduating seniors -- of which Tommy was one -- come to school in their pajamas on the last day of school.  Of course Tommy had never been one to get very involved in school activities.  He never went to football games or pep rallies or things like that. So I wasn't sure if he would even want to participate in Senior PJ Day, as they call it.

Well, he DID want to participate. And he wanted to participate in a very special way.

"Mother," he said to me. "I've been hiding all my girlish feelings from everyone for so long, always pretending to be someone that I'm not.  Well, tomorrow is PJ Day -- and it's the last day of school forever. So I want to go to PJ Day as Tammy.  The real me.  In a nightgown.  And if people don't like it, well fuck 'em!"

Tammy had never used language like that in front of me before.  It showed how strongly he felt about what he wanted to do.  So I gave him my full support.

Senior PJ Day arrived and we both got up extra early.  We took extra time getting Tammy ready for "her" very first appearance at Tommy's high school.  I warned Tammy that people would be shocked and that he would probably get some pretty strong reactions from people.  But Tammy was determined.

We hadn't discussed it before, so I asked Tammy, "So what exactly are you going to wear today.  Which nightgown have you chosen?"

Tammy replied.  "I have a favor to ask. Can I borrow your white night gown and robe set?"                                                                                  "You mean the one with the eyelet and lace trim? And the buttons down the front?  I haven't worn that one in years.  Well, I guess you can borrow it.  But, it's a bit...grown up and...romantic to wear to school."                                                                                                    "I understand. But it's what I want to do." And with that, I dug out the nightgown set from deep in my lingerie drawer.                                                                                           Tammy put it on and he looked absolutely stunning.                                                                               Ten minutes later I was driving him to school.  His hair and make-up were perfect. He wore just a bit of perfume.  As we pulled up to the front of the school, I asked one more time, "Are you sure you want to do this?"                                                                                             

 "I've never been more sure of anything." And off he went to the entrance of the school.

All morning I worried about My Little Princess being at school looking like a bride on her wedding night.  I kept me cell phone with me in case I got a call and needed to rush to school.  But no call ever came.  At 1:00, I drove back to the school to pick up Tammy, as the last day always ended early.

"How did it go?!?!" I asked excitedly as Tammy climbed into the car.

"It was great!" Tammy said with a smile.  And he proceeded to tell me all about his day.