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.

Sissy Roommate Part 7 -- Romantic Autumn Afternoon

When Thanksgiving week came around, most students left to go home to spend the week with their families.  But Tank had a big game and practices over the Thanksgiving break, so I stayed to be with him.  And when Tank wasn't at his two-a-day practices or in the gym, he was spending his free time with me.  Here some photos that Tank took of me one afternoon.  He had me get all dressed up and we went into the woods.  He brought a bottle of wine and we found a secluded place where we drank it and then had sex -- right there in the woods!                                                                                                                                   As I've said, my life is getting a bit confusing and complicated since I'm spending so much time dressed up and acting as a sissy girl.  Tank is insisting that I should be dressed and made-up like a girl any time that he's in the dorm room!  I want to make Tank happy -- and I certainly don't want him to be angry with me -- but it's really hard for me to do what Tank is demanding.

To give you a sense of how complicated my life has become: I have to be all dressed and looking pretty for Tank when he returns to the dorm around 9:00 after his early morning work-outs.  He's already eaten breakfast with the team but I always have some eggs and toast ready for him when he comes in that I make on the little hot plate we have. While he eats, he likes to watch ESPN on the TV -- and get a blow job from me.  Tank finishes with his breakfast (and with my mouth) a few minutes before 10:00.  Then he goes off to take his shower and do whatever he does all morning (I don't think he goes to a lot of classes).                                                                                                                            But I have 10:00 lectures to get every day -- and no time to wash off my make up and change back into my boy clothes.  At first I was skipping a bunch of lectures but I was really falling behind.  I realized the only way I could keep up with my lessons was to rush over to the lecture halls still dressed as a girl. I keep to myself and try to sit in the back so that I don't attract too much attention.  But sometimes a boy will sit next to me and try to flirt with me.  I guess I find that sort of exciting, but I try not to encourage it too much.

After my morning lectures, I stop by the dining hall -- still dressed as a girl -- and quickly eat my lunch.  At first I thought everyone would notice me, but so far I haven't had any real issues. Then I rush back to the dorm because Tank usually shows up there around 12:30 after he's had lunch with his buddies.  When Tank arrives, we usually make-out for a little while and then he has sex with me.                                                                                                         I had to beg Tank to let me change back into my boy clothes in the afternoons because that's when I have my small classes.  I can get away with sitting in a big lecture hall pretending to be a girl -- but that doesn't work at all for the small classes.  But since I don't have any classes on Friday afternoons, I usually stay dressed as a girl all day long.

Something else happened on that trip to the woods over Thanksgiving.  After Tank had finished fucking me, he handed me a small bag.  "You have to start taking these," he said.  I looked inside and wasn't sure what I was looking at. "They're birth control pills," Tank explained. "You know, female hormones.  They will make you more like a real girl."  I asked him where he got them and he explained that he told the team doctor that he needed the pills for his girlfriend, and the doctor handed him a six-month supply, no questions asked.

"But I don't think boys are supposed to take those," I stammered. "I mean, those are only for real girls."

"Shut the fuck up, you stupid sissy bitch. I said you're going to take them and that's what you're going to do. In fact, take the first one right now!" 

I fumbled with the packaging and managed to pop out a single pill from it's container. I washed it down with the wine.

"Good," said Tank.  "Now suck me off quick before I have to go to practice."

Sissy Roommate -- Part 6 -- Sissy Doubts

Tank has been giving me money almost every week to buy more outfits.  I think it gets him very excited to send me off to the mall with the assignment of buying clothes to wear that will make me look pretty for him.                                                                                    Here's a cute little outfit I bought on my shopping trip last week.  I love this little denim top.  I think it really shows off how skinny I've become since I started dieting extra hard.  I think my arms look so pretty and feminine in this photo.  And of course I bought another short skirt.  I love how this one is just a little bit flouncy and how it moves and swings as I walk.  But it is so short! If I sit or bend over, my lacy panties are on full display for all to see.   

Tank has been sending me out in public dressed as a girl more frequently.  Tank took these pictures of me outside our dorm building before telling me to go to the Student Union to buy some snacks for him.  At first I was super nervous about walking around campus looking this way. But I was really surprised to discover that nobody recognized me.  I guess that's partly because I was always sort of a loner and didn't have any real friends on campus when I was living as a boy.  But I also like to think it's because I look really cute as a girl.  I certainly get some admiring looks and sometimes comments from the boys I pass as I walk around campus.

I think Tank really likes me and that makes me very happy.  He certainly gets excited and wants to have sex with me a lot. But I guess I should tell you that Tank sometimes brings girls -- especially cheerleaders -- back to our room. He says he needs to keep up his image and that people would think it was really strange if he wasn't sleeping with a bunch of girls.  Anyway, the hardest part is when he texts me that he's bringing a girl over and I have to clear out of the dorm room immediately.  And sometimes I'm all dolled up because I was expecting to spend the evening with Tank.  So I have to quickly clean off my make-up and change back into my boy clothes and plan on spending the night sleeping on the couch in the TV room downstairs.  I guess I get a little jealous when Tank is sleeping with girls and sometimes it's hard for me to fall asleep on the couch thinking about him being in bed with them.  But I believe that Tank really loves me -- in his own way -- and that this is just one more way I need to be a good sissy and to be supportive of my man.

As much as I enjoy making Tank happy -- and as natural as it has become for me to dress and act like a girlish sissy -- sometimes I wonder if I am doing the right thing.  Each day I feel a little part of the person I was before I met Tank disappear.  Sometimes I even get confused if I'm even really a boy any more.  Where will all this lead?                                                                      Anyway, tomorrow I'm going ride the bus back to the mall to buy some more clothes. And this time I am going to go dressed as a girl. That way I can try on things in the ladies dressing room and people won't look at me funny when I'm shopping for bras and underwear. I don't think anyone will guess that I'm not really a girl.  Do you?

Sissy Roommate - part 5 -- Some New Clothes

Well, my trip to the mall was quite an adventure.  I had made a list of the things I thought I would need.  More sexy underwear, some sexy tops and some short short skirts were definitely on the list.  I also planned to buy some more make-up and some brushes and sprays to make my hair look nicer.  And I hoped I would have enough money left over for some perfume -- I thought that Tank would really enjoy that.                                                                             But one thing made me extra nervous about my shopping adventure: Tank had also told me to get some clothes to wear outside.  He was going to make me go outside fully dressed as a girl! So I needed to be smart about what I bought since this wasn't just for sissy dress-up games in our dorm room.

Here's one of the outfits I bought for myself on that first trip to the mall.  Don't you like this cute little top?  I didn't realize when I bought it that it wouldn't even cover my tummy!  But I think it looks super cute.  And I think it looks nice with the short plaid skirt I bought.  I also bought some shoes and a bag that I could take outside with me.

Here's a close-up of my face.  I think you can see that I've gotten a lot better with my make-up.  I think I look very pretty in this photo.                                                                                         Maybe you can tell that I have plucked my eyebrows into a pretty arch shape.  That, along with some eyeliner and mascara, helps make my eyes look extra big and pretty.                                                                                             And Tank really likes it when I wear lipstick.  With some practice, I've gotten really good at putting it on. I spent a little more to get extra long wearing lipstick because regular lipstick doesn't stay on for very long since Tank likes kissing me so much.

And as you can see, Tank was true to his word.  He made me go outside behind our dorm to take these photos.  I was so scared that someone would see me as we went out the back stairs.  But the sensation of being outside dressed as a girl was so exciting!  I loved the feeling of the cool fall air on my exposed skin.  I loved posing for my man as he took dozens of photos of me.                                                                                                And I could tell that Tank was getting excited by taking me outside and making pose for photos.  Because when he was done taking pictures, he grabbed me by the wrist and rushed me back upstairs to our dorm room.  "All fours!  Now!" he growled. I quickly did as I was ordered and positioned myself on my hands and knees on the floor.  Tank pulled down his pants and approached me from behind, lifting up my skirt and pulling down my lacy panties.  Tank loves to fuck me in all sorts of different positions -- but I think he likes it best when I'm on my hands and knees.  I love it when he spanks my bottom while his dick is pumping in and out of me.  It gets me so excited when Tank says how tight my "pussy" is while he's fucking me.  I have to admit that it's pretty painful when Tank fucks me because his cock is so enormous. Sometimes it hurts so much that I cry while Tank is pounding away at me.  But it also makes me feel so happy and fulfilled to be pleasing Tank and to submit to him so completely.

Sissy Roommate -- Part 4 -- My Purple Dress

So from that day forward, I have been Tank's sissy.  He has a tremendous sexual appetite, needing to cum two or three -- and sometimes more -- times every day.  He also expects me to do other stuff for him, like his laundry, which I do every day without being asked.  I know he expects it so I just do it.

At first, I would go through bouts a doubt and self-loathing.  What was I becoming?  Why was I doing this?  I would think about performing oral sex on Tank and get sick to my stomach.  But then these feelings would subside and be replaced by feelings of warmth and happiness and satisfaction unlike any I had ever experienced before, as I assumed the role of the subservient, obedient woman serving her superior, masculine male. 

About half of the things I took from the lost and found bin at the gym turned out to fit me pretty well and it seemed to please Tank when I would get dressed up.  I also got much better at doing my make-up and making my hair look prettier. I also bought a ladies razor at the drug store and started shaving my body. I really like it when Tank runs his big rough hands up and down my soft, smooth legs. 

The best item that I took from the lost and found was a really pretty purple dress.  It had a lovely floral print and a fancy lace inset around the neck line.  I felt so pretty when I wore this -- just like a princess!  

Sometimes, when I would emerge from the bathroom after putting on my dress and my make-up, Tank would have me stand in the middle of the room with my gaze directed downward -- a position of total submission.  He would say something like, "Who do you belong to, sissy bitch?" and I would reply, "I belong to you, Sir." This little ritual would continue for several minutes until Tank was worked up into a frenzy.  Then he would grab me and roughly shove his enormous dick into my mouth.  

Other times, when he saw me wearing this dress, Tank would sit naked on the edge of his bed and he would tell me to climb on his lap and we would make out for a while before he decided it was time for me to suck him off.

Even though I looked pretty in the clothes I had taken from the lost and found, after a while, Tank got tired of seeing me wearing the same things all the time.  He told me to get some more clothes. He peeled off four $100 bills from a fat roll of money he had in his sock drawer and threw them at me. "Go buy some new clothes. Get some sexy stuff."

I had never bought girls clothes before but at least I knew something about my size based on the things I took from the gym.  I decided that the next day I would take the bus to the mall.