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 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"

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?

Taking my Sissy Husband on Vacation

My husband and I are having the most wonderful vacation together.  That's me in the photo on the left, the brunette in the black dress.  But that's not my husband in the photo! That's my new vacation boyfriend, Jerry.  I met Jerry earlier this week at the resort bar.  You see my husband is not a real man like Jerry.  My husband is a feminine, submissive sissy. 

That's my sissy husband in this photo -- the pretty blonde "lady" in the sexy gold dress.  His real name is Martin, but he is living only as "Tina" this week while we are on vacation.  And as you can see, Tina landed a handsome new vacation boyfriend too! His name is Darren.

My Tina is very, very good at passing as a woman.  He works hard at keeping his body slender through a strict diet and body-sculpting exercises.  He keeps his hair long all the time, but dyed it and had it styled especially for this trip.

Don't you think they make a cute couple?  Darren is everything that my Martin/Tina isn't. He's strong, confident and decisive.  A real Alpha male! I love seeing Tina with Darren. It seems like Tina doesn't have a single idea of his own when he's with his hunky new boyfriend -- Tina seems only capable of agreeing with whatever Darren says and whatever Darren wants to do.

I love seeing how Tina behaves when he's with a real man!  That's why I planned this vacation to a singles resort.  Although we have been out together as two women many times before -- to restaurants and bars and so on -- we had never taken a week-long vacation like this before.  For Tina -- and for me -- it is a wild, new experience!

I know my sissy husband enjoys his time as Tina.  I know that his need to express him feminine side is far too powerful for him to resist.  And being in the arms of a strong, masculine man is so exciting for him, throwing his feminine feelings into overdrive. But tricking a man to believe that you are a real woman when you are not is playing with fire!  And Tina knows this. Each moment he spends with an unsuspecting man fills Tina with equal parts excitement -- and fear that his secret will be revealed.

Tina and Darren have been an item for three days now -- and we have three days left in our vacation.  Can Tina keep up the act for the rest of our vacation without letting Darren find out the truth?  I certainly hope so.  I expect that Darren would be furious beyond belief if he learned that the woman he was falling for was really a man.

So how does Tina manage to keep his secret? Well, the first night was easy --  just some flirting and a little pawing at the resort bar, with a brief good night kiss at the end of the evening.  By day 2, things were heating up, with some heavy making out during the day and a hand job in Darren's room at the end of the evening.  (His cock is enormous, Tina reports!) 

Today is day 3 of their steamy relationship.  I caught Tina and Darren making out like crazy earlier today -- including in the swimming pool!  Now we are all dressed up for a double date together.  First we'll have some Happy Hour cocktails, then a romantic, candlelit dinner together, followed by dancing at the outdoor bar until late. It's what happens after that that has Tina very nervous.

"You better hope he likes blow jobs!" I told Tina. "And I hope you are really good at giving them.  Because he is going to expect to get some serious action from you. And since he can't fuck you, you better find some other way to keep him interested." Tina has practiced giving blow jobs on the strap-on dildo I sometimes use on Tina's backside.  But Tina has never had a real cock in his mouth -- or down his throat.

 

Of course, I've been fucking my new vacation boyfriend every chance I get this week.  We run off to his room a couple of times during the day and of course in the evening. He is amazing in bed! And I always give Tina a detailed report on my sexual encounters with Jerry.

I really hope that Tina -- and his pretty mouth -- can keep Darren satisfied and unaware of the truth. They make such a cute couple and Darren really seems rather smitten by Tina. And I can tell Tina is really falling for Darren.

Keep your fingers crossed that Tina can really pull it off. With a little luck -- and a lot of sucking -- Tina just might come home with wonderful memories of his romantic vacation with Darren -- and a tummy full of Darren's hot, sticky cum!

 

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

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

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

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

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

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

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