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"