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"

Bad News for My Sissy Husband

"Sweetie, do you have a minute to talk?" I called up the stairs.  My darling sissy husband, Lily, came down right away.

"Yes, Martha. Is there something that you need?" he asked.

"My, don't you look extra pretty today!  That pink top is super cute on you and really shows off how you are...developing.  And I love that necklace on you!" I cooed.

"Thank you, Martha," he replied softly. I could tell he was both thrilled and a bit embarrassed with my compliments.

"Sweetie, we need to talk. Now I know you have really been looking forward to our vacation to the Bahamas tomorrow," I started.

"Oh yes, Martha.  I'm very excited about our trip!" he replied breathlessly.

"Yes, well," I started. "There's been a change of plans.  You're not going," I stated matter-of-factly.

Completely blindsided by my announcement he responded, "What? No! We've been planning this trip for months!"  His eyes were starting to tear.  This announcement was getting him rather upset.

"Now Lily, really!  Think about it.  I mean, just look at you.  Look how much you've changed!  Your hair, your breasts, your hips.  You have become so feminine!  How can I be expected to go on a romantic Caribbean vacation with you?  You can barely even pass as a man anymore!  Needless to say, you can't take your shirt off on the beach now that your boobs have grown so much," I explained.

"But I did all of this for YOU!  YOU wanted me to become more feminine, more ladylike.  I made all of these changes because YOU wanted it!" He was starting to cry as he spoke.  Goodness, the hormones make him so emotional!

I put my hand on his shoulder, "Oh, Lily, of course I know that. This is how I want you. Soft and feminine and gentle.  I love having you as my sweet little sissy housewife.  You look and smell so pretty and you take such wonderful care of me.  You are exactly the way I want you. At home, that is.  But on a romantic vacation?  Well, that obviously is not going to work."

"So you cancelled all of our vacation plans?" he asked stupidly.

"Oh, good heavens no, silly girl.  The trip is all paid for.  I'm going with Ben."

"Ben? Who's Ben?" Lily asked.

"Ben Martins, silly. My editor," I said. Then the wailing really began.  

"You're going on vacation with Ben?!?  Why? How? What's going on?" Lily was starting to get a bit hysterical by this point.

"Well, Lily, Ben and I have been spending a lot of time together finalizing my latest book. And he is going through a difficult time since he is getting divorced.  Anyway, over the past couple of months, he and I have gotten rather...close.  He really is a very nice man.  And so tall and handsome!"  The crying got much worse when I said that.

By now I was growing tired of Lily's sobbing. "Now calm yourself. You know this is for the best. Look, I am a woman and I have needs -- and believe me, he really knows how to fill my needs!  Ben and I will be able to have a wonderful, romantic vacation together in a way you and I simply can't anymore. Besides, you have fallen way behind on your chores and this will give you a whole week to get caught up."

Lily had no words in response to that.

"And since I'll be spending more time with Ben at his apartment when we get back from the Bahamas, I thought it would be nice if you would go over there while we're away and get it all tidied it up.  It really is a mess and you wouldn't want me having sex in an apartment that wasn't properly cleaned, now would you?"

"Well, would you?" I repeated a bit more sternly, in case Lily thought it was a rhetorical question.

"No, I guess not," he answered softly.

"No, of course not," I agreed.  "Now pull yourself together. I know, let's go to the mall and I'll buy you something pretty to cheer you up.  And while we're there, you can help me pick out a new bikini and maybe a sexy nightie to take on my trip.  OK?  Now dry those eyes and grab your purse."

You Sissies Will Be Punished!

 

Sissy Roommate - Part 10 - The Conclusion

 I know it's been a long story, but now you are up to date.  It's the start of Tank's Junior year.  I dropped out because I knew I couldn't care for Tank and take classes at the same time.  But Tank and I will be living together this year in a beautiful condo that a rich alumnus has provided for Tank.  I've been working hard to make sure it is clean and all ready for Tank when he arrives, which should be any minute now.

I bought some new clothes over the summer, including the outfit you see me wearing here.  I sure hope Tank likes it when he sees me.  And I curled my hair which got longer over the summer.   I'm making an extra effort to look nice since I haven't even seen Tank all summer long!

And best of all, the hormones really kicked in over the summer and my breasts grew a lot! 

Excuse me, my phone is ringing.  Oh great, it's Tank!

"Hi Tank! Are you almost here?  The condo is all clean and I...."

"Stop talking!" Tank barked through the phone. "Jesus Christ! Just shut up and listen!"

"OK  Sorry," I replied softly.

"Look, a lot of stuff happened over the summer. I'm engaged," Tank explained flatly.

"What? I don't understand. Are you joking? What are you saying?" I babbled.

"If you would shut the fuck up, I would tell you, you stupid sissy bitch.  You remember Amber Destry, the swimmer from the Hall of Fame event last Spring?"

"Yes," I answered softly. My tummy started doing backflips. Remember Amber?  How could I forget. She was like a living Barbie doll.

"Well we got engaged this summer. And her dad, who's loaded, has bought us a house off campus to live in together."

"But what about our condo? What does..."

"For the last time, shut the fuck up!  The good news for you is that the alum that owns the condo has agreed to let Jefferson and Jackson live there.  And they seemed pretty interested in you when they met you last year, so I decided that you can just start being their sissy from now on."

I couldn't even make sense of what I was hearing. Tank was engaged to a real girl.  I wasn't going to be living with him.  And Tank had just decided that I would now be...given?...to Jefferson and Jackson.  I started to feel faint.

"Got to go," Tank said and he hung up.

I put down my phone and grabbed hold of the kitchen counter to steady myself.  What was happening?  What was I going to do?  I didn't have a penny to my name and I had no where to go.  My head was spinning.

But not for long.  Because just then I heard the front door being unlocked and in walked Jefferson and Jackson.

"Hello sissy!  We're home!" shouted one of them in a loud sing-song voice.  The other one broke out laughing.

"Damn!  Look how he's dressed!  Did you get all dolled up because you knew we were coming?  You are one sexy sissy!" the first one said. 

The other one grabbed me by the throat with one hand and roughly grabbed one of my soft new breasts with the other. "It's true, Jack! The sissy really does have titties like Tank said!"  He kept squeezing my breast and my neck really hard -- and then he licked my face, from my chin up to my forehead.

Then Jack laughed and said, "You know how I love titties!" Then he said, "Keep holding him like that, Jeff.  I'm gonna get this party started!" as he unzipped his pants.

THE END

Sissy Roommate -- Part 9 -- Sissy on Display

It was the last week of Spring semester.  Again, I was doing very poorly in my classes because I was spending so much time and energy in performing my sissy duties for Tank.  I was pretty sure that I hadn't done well on my finals.  Regardless, Tank and I would be leaving our dorm room tomorrow.  Tank would be heading home; I would stay in the area and get a job for the summer.

It was Thursday afternoon and Tank had finished his last final exam that morning.  He seemed pretty happy that finals were done and so he spent most of the afternoon fucking me.  He was just starting in on me for the third time when his cell phone rang.  It was Jefferson, one of his buddies from the football team.  Tank put it on speaker, "Yeah, what's up?" Tank asked.

"Did you forget about this afternoon?" asked the voice on the phone.  "We were all supposed to be at the President's house for the awards ceremony at 4:00. I bet you forgot, didn't you?  Everyone is asking where you are.  You gotta get your ass over here."

"Shit," muttered Tank.  "I'll be there in ten minutes."

"And you're supposed to bring a date," reminded Davis. "Everyone is supposed to bring a date."

"Fuck fuck fuck.  Alright. Later." Tank hung up then barked at me.  "Hurry up and get dressed into something nice. You're coming with me to this awards thing."

"What?"  I asked.

"Just shut up and put on the nicest dress you got.  We have to hurry up."

I did as I was instructed and went to my closet.  I pulled out a cute polka dot dress that I had bought for our Florida vacation.  When Tank emerged from the bedroom, he was wearing a suit and tie.  I was breathless -- I had never seen him wearing a suit.  He looked so, so, so handsome.  My tummy did a somersault just from looking at him.  

"Are we really going to the University President's house?  For an event?  With other people?"  I was in shock.

"That's about right.  I'll explain more on the walk over there."

I quickly put on dress from vacation.  The dress was sleeveless so I added a little white sweater.  I freshened my lipstick and ran a brush through my hair.  I grabbed a purse before Tank pushed me out the door.                                                                                                                As we raced across campus Tank explained that at the end of the year, the new inductees to the school's Athletic Hall of Fame were invited to an event at the President's house.  A bunch of deans and other important people would be there.  And the press.  Tank explained that he was being inducted along with his buddies Jefferson and Jackson, both offensive linemen, both co-captains of the football team, and identical twin brothers!  He said there would be star athletes from other teams but he didn't know who.                                                                               He warned me that I better not to screw up and that everybody had to be totally convinced that I was really a girl -- or he would kill me (I don't think he meant that literally -- but he made his point.)

He told me to tell people that I was a friend of his from his hometown and that we had gone to high school together.  He said that I should say my name is Mary Ellen Molloy.  I agreed to do as he said.                                                                                  I struggled to keep up with him as we made our way across campus as my platform sandals were not made for walking fast.  And as we quickly walked my head was spinning -- first from the thrill and terror of being out on display like this.  Of course I had been out with Tank in Florida but that was different.  We didn't know people in Florida.  But this was campus!  The stakes were completely different.                                                                                                                       But my head was also spinning with the question of what Tank was thinking -- and feeling.  Tank was taking me out, in public, right here on campus.  People would see us together.  People might think we were an item. Should I interpret this as a new step in our relationship?  Was Tank ready for me to be something more than his little sissy sex toy?

I didn't have time to wrestle any further with these questions because we had arrived.  We walked into the President's mansion and there were like 70 people there.  I think I counted about 15 athletes receiving the Hall of Fame award, plus each of them had a date.  There were the senior university officials, including the president and his wife.  Then there were about 20 reporters and photographers there.  I had never been to an event like this -- either as a boy or as a girl.  Everything was so fancy.  Waiters brought around trays of champagne and hors d'oeuvres.  I could hear a pianist playing in another room.  It was like being in a movie.                                                                                                                             Immediately, Tank and I went over to his buddies, Jefferson and Jackson. "Glad you could make it," Jackson joked.  Then the two of them noticed me.                                                                                        "Oh shit!" said Jefferson. Then in a low voice, "Is that your fucking sissy?"                                                                            "Oh my God!" I screamed to myself.  I didn't know that Tank had told anyone about me. I started shaking.

"Keep your pants on.  And keep your voices down," Tank growled at them.                                                               Tank was then called away by a photographer leaving me with his two buddies.  "You are so fine," Jackson said as he looked me up and down.                                                             I gulped and managed to squeak out, "Would you excuse me please," and I walked over to the buffet table downing another glass of champagne on the way to calm my nerves.                                                                                                             I barely spent any time with Tank for the next hour and a half; the athletes were mostly talking among themselves, posing for photographs or being cornered by the university bigwigs.  The other male athletes' dates were really nice and we mostly talked among ourselves while our boys were busy.  The President's wife was also very nice and I talked with her for a bit.  I felt like I was pulling it off pretty well and the champagne was helping to give me a little extra courage.

The afternoon was nice but a couple of things made me...uneasy.  First off, Jefferson and Jackson were spending a lot of time looking at me from across the room and whispering to each other when they weren't being hounded by reporters.  That made me really uncomfortable.  The other things was that Tank was spending a lot of time talking to a girl athlete, Amber Destry, a champion swimmer.  Everyone knew who she was because she had been on the Olympic team!  Not only was she an incredible athlete, but she was super gorgeous -- over six feel tall and looked like a real life Barbie -- if Barbie as a champion swimmer.  I will admit to feeling pretty jealous when I saw this.

By 6:00, the event started winding down.  Tank told me to go back to our room on my own because he was going to go have dinner with Jefferson and Jackson.  I wasn't too happy about that but of course I didn't say anything.  I said my good-byes to some of the other girls that were still there and started the walk back to my dorm, alone, a little tipsy from all the champagne, with my head full of questions.

Tank didn't come back to the dorm at all that night. I had to vacate the dorm and turn in my keys by 10:00 the next morning, so I finished packing up my things and left for the summer, never having the chance to say good bye to Tank.

Sissy Roommate Part 8 -- Spring Break Sissy

The rest of the fall and the winter went by quickly.

Of course, Tank set several new school football records -- and the team did make it to a Bowl Game for the first time in decades.  Even though football season ended, Tank continued to train hard all year round.

I continued to put all my effort into serving Tank and making him happy.  My own school work suffered badly -- I did terribly on two of my fall semester finals. But I realize I can't do everything and I have decided that caring for Tank is my top -- and sometimes only -- priority.

You may remember that last fall, Tank had me start taking birth control pills -- female hormones.  I didn't want to at first but Tank insisted.  Well they have had a powerful effect on me!  Almost immediately, I could feel swelling and intense sensitivity in my nipples and breasts.  My butt and thighs have gotten a lot fuller while the rest of me has gotten even skinnier. My complexion became clearer and my skin softer. And my hair started growing much faster and thicker.  There is no doubt that the birth control pills are starting to make me much more like a real girl!

As spring break approached, Tank told me that he was going to Florida.  Some wealthy alumnus was letting Tank use his beachfront condo for the week.  And do you want to know the best part?  Tank asked me to go with him!!!  I leapt into his arms and kissed him so hard when he asked me!  I was over the moon!                                                                         Of course, I didn't own anything I could wear on a vacation in Florida so I had to ask Tank for some extra money to buy some new things, including the super cute bikini I'm wearing in the photo.  What do you think?                                                                                                 When I go to the beach or to the pool, I wear a pair of extremely tight panties so that I'm totally flat in the front.  And I added some special padding to the bra top that helps push my teeny breasts up so that I look like I have boobs like a real girl.

We had  really great time in Florida -- and I had Tank all to myself.   Well, mostly.  He still went to a local gym every day.  But sometimes I went with him.  I was able to take a Zumba dance/exercise class with a bunch of other ladies which was really fun.  

The whole week was a dream.  I would get up extra early to take my shower and to make myself look pretty before Tank even woke up.  Then I would make him breakfast and then Tank would have sex with me.  I think we did it in every room and on every piece of furniture in the condo!  After that would would go out to the beach or to the condo's pool.  I think it really turned Tank on seeing me out in public in my bikinis!  And even though the beach was public, Tank still made me give him secret hand jobs -- right there on the beach!

And in the evenings, Tank would take me out to restaurants and night clubs.  It was like we were really boyfriend and girlfriend!

I was so proud to be seen with Tank.  First of all, he looked so handsome when he put on a nice shirt and pants to go out. And of course, a lot of people would recognize him when we were out and would ask for autographs and selfies.  I felt like I was being escorted by a Hollywood celebrity!  It was so exciting and dreamy!

Tank was so nice to me the whole time we were away.  He even bought me a little gold necklace -- it's a pretty mermaid pendant on a thin gold chain -- for me as a souvenir of our trip.

I was so happy while we were in Florida.  I felt like the time there -- parading around in my bikinis, being on the arm of a handsome man, receiving a lovely piece of jewelry -- was making more feminine, more girlish, every day.  I think the experience was changing how I thought and how I felt about myself -- and how I felt about Tank. One night, as I was sleeping tightly wrapped in Tank's arms, I even dreamed that I was Tank's wife.  Isn't that incredible?  

I'm really in love with Tank.