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.