Dressing for Sissy Success

 It's a very exciting moment when your Sissy is ready to be sent off for his first day of work.  I have made arrangements with a few local businesses to hire my Sissies as receptionists and secretaries. 

I have a wonderful arrangement with these local businesses.  For $3.00 per hour (paid directly to me of course) they get the services of a meek and eager-to-please Sissy.  I ensure that all my Sissies are well trained and so it is a real bargain for the employer.  And of course, if the boss wants some "extra service" from his newest employee, well that's fine with me.  I don't care if my Sissies spend half their day on their knees under the boss's desk with a big cock in their mouth.  As far as I'm concerned,  the boss is always right!

The only condition I place on the employers is that I insist that everyone in the workplace know exactly who and what my Sissies.  Sure, many of my Sissies could pass as just another genuinely female bimbo -- but that's not what I want.  I want everyone to know -- from the other girls in the office, to the big hunks on the loading docks, to the salesman that visit the office -- that the sweet little thing serving them is a Sissy.

When it's time to send your Sissy off to work, I think choosing the right wardrobe is terribly important.  Your Sissy's outfit needs to scream femininity.  It needs to be sexy and impractical.  It needs to show off your Sissy's new curves and as much cleavage as possible.  It also needs to be something no genuine woman would wear to the office.  In fact, I try to dress my Sissies in a way that infuriates and insults the other women in the office, making the Sissies' life just as uncomfortable as possible.

Dressed this way, there is no way that your Sissy's life won't start to get complicated.  Some man is going to start hitting on your Sissy -- maybe a Salesman visiting the office, maybe one of the janitors -- who cares.  And my Sissies are trained to never --  never ever -- say no to the advances of a man.

So here are a few of the outfits I have picked out for my working Sissies recently.  It can be so much fun to dress up your little working Sissy like this and then enjoy the show!

A Sissy and his Sister

Sissy Sandra sat on the beach with his twin sister Emily.

"Say Cheese, Sandra!" Emily's husband Mark called.  Sissy Sandra turned toward the camera as Mark snapped another picture.

Poor little Sissy Sandra.  He was a pathetic, quivering shell of a person.  Fortunately his sister Emily took good care of him.

Their parents died when they were little children and they were sent to live with their Aunt Jenny.  Aunt Jenny had some serious issues with men and didn't like the idea of having a boy in the house.  So she decided that her little nephew Sammy would become her neice Sandra.  From that moment on, Sissy Sandra's life became a bizarre nightmare.

Aunt Jenny decided that Sandra should emulate his sister Emily in every way.  Sandra was not permitted to have wants or ideas of his own.  When Emily wanted Barbie dolls for Christmas, they both got Barbie dolls.  When Emily wanted to take ballet lessons, they both took ballet.  When Emily wanted to get her nails done, they were both taken to the salon for manicures.  Whatever outfit Emily put on in the morning, Sandra would have to put on his matching outfit.  Sissy Sandra was raised as a girl, a copy of his sister, in every way.

And of course, when Emily entered puberty, Aunt Jenny arranged for hormones for Sissy Sandra.  And before sending her twin "neices" off to a women's college in New England, Sissy Sandra underwent facial surgery and had breast implants to better match his beautiful, sexy sister.

Raised in this way, Sissy Sandra had no personality of his own.  He knew no existance other than to be exactly like his lovely sister.  After years of living in fear of the severe punishments he would receive if he didn't look, act, sound and even think like his sister, poor Sissy Sandra didn't know any other way to live. 

And so, Sissy Sandra lived with his sister and her husband.  Emily was very kind and gentle with her Sissy brother, helping him to be as feminine and beautiful as she was herself.  Poor Sissy Sandra could only feel peace and contentment by knowing he was almost identical to his exquisite sister.

But what sister Emily didn't know was that her husband Mark was taking advantage of this situation.  He had convinced Sissy Sandra that whenever Emily was away, then Sissy Sandra had to become Mark's "wife".  It made perfect sense, Mark explained.  To be like his sister, Sissy Sandra had to do EVERYTHING his sister did.  And so, whever Emily left for an hour or a day or a week, Sissy Sandra would be ordered into the Master bedroom to be Mark's surrogate "wife", doing all sorts of nasty things that Mark could never ask his wife Emily to do.

Sissy's DisneyWorld Vacation -- Part 3

Stepmother and I awoke early and drove to the Magic Kingdom.  My visit to the other parks had been...unusual.  In the end,  I guess I had fun -- even though Stepmother made me go dressed as a girl.  I had dreamed of visiting DisneyWorld all my life and so far it was even better than I had imagined.  And Stepmother had never been nicer to me than she had been over the past couple of days.  But today we were going to the Magic Kingdom -- the very heart of DisneyWorld.  Stepmother had me dressed as a girl again.  I was wearing the black tank top and capri pants that I had worn to Epcot.  At least I wasn't wearing the flowered sundress she made me wear yesterday!

As we approached the Magic Kingdom we drove past a giant banner that read "Happy Halloween!  Disney Costume Contest at 3:30 and Parade at 4:00!"  I had forgotten that today was Halloween.

Stepmother drove past the entrance to the Magic Kingdom parking lot and drove up to one of the big hotels at DisneyWorld .  We parked and went into the hotel.  I kept asking Stepmother where we were going but she wouldn't answer.  That's when I noticed that we were following signs to the "Bippidi Bobiddi Boutique".  When we arrived at the "BBB" I discovered what it was:  It is a little "salon" where Disney employees dress little girls up in Disney Princess costumes and make-up for their visit to the park -- this is all true.  And Stepmother was registering me for an appointment!

"Well hello there.  You must be Alice," said a perky lady in a Fairy Godmother costume.  "Good thing you made a reservation," the lady said to Stepmother.  "We've been booked solid for today since August!  All the girls want to be dressed as Princesses on Halloween. " 

I was terrified.  What was Stepmother doing?  Was she crazy?  There was no way I was going to put on some kind of costume and go to the Magic Kingdom.  Besides, this was for little girls -- like 5 year olds -- not for teenagers.

"Stepmother," I whispered urgently, "I don't want to get dressed up in a costume!  I'm not doing this!"

Stepmother roughly grapped me by the arm and dragged me to a quiet corner.  In a low and threatening growl she said to me, "Don't you dare argue with me.  Who do you think you are?   You are going to do whatever I tell you to do.   Or do you want me to show your father the photos and video of you prancing aroung Disney Studios in your pretty little sundress?"

Oh no!  Anything but that!  I was completely trapped.  I couldn't say a word.  I just stared at the floor, completely defeated. 

"I thought so," Stepmother said with a wicked smirk.  "Now start co-operating and don't make me angry.  And besides," she continued with a softer voice, "We're far from home and no one will ever know."

And so I went back to the lady at the front desk.  "Is everything alright, sweetie?" she asked me.

"Yes," I replied softly.  "I just thought that I was...too old to do this."

"Oh nonsense," the lady replied with a laugh.  "We get big girls in here all the time -- especially on Halloween."

  "Now, who do you want to be dressed up as today?  Snow White?  Cinderella?  Ariel?" Stepmother asked.  I could see that she was enjoying my humiliation.

"I...I...I..." I just could think or speak.

"Oh I know," the salon lady said.  "All the teenage girls want to be Alice in Wonderland.  And your name is Alice, isn't it?"

"Oh yes, that sounds perfect!  Don't you agree, Alice?" Stepmother replied.

I just stood there, numb.

Before I knew what was happening, I was led back to a small cubicle where a couple of ladies started working on my outfit and my make-up.  First they pinned a long curly blonde wig on me and put me in an outfit with a short skirt and stripped tights.  Stepmother made me pose for some photos before announcing that she wanted to see a different outfit and a different wig.

Then they tried a long straight wig on me.  Stepmother took more photos.  I was close to tears.  But my nightmare continued. 

No, my Stepmother said, she didn't like this one either.  She also shot me a look that clearly said to put a smile back on my face -- or else.

Then the ladies brought out a longer, more feminine Alice in Wonderland costume.  The dress fell to just below my knees and it had puffy short sleeves.  The outfit included a flouncy petticoat and a ruffly apron that was tied snuggly around my waist. They added a long wavy blonde wig with a big velvet bow.  The final touch was a pair of high heeled Mary-Janes.

"Perfect!" my Stepmother proclaimed when they showed her this look.  "Oh Alice," she gushed.  "You look just lovely!"

And so we left the salon and walked through the hotel and entered the Magic Kingdom.  It was awful.  People kept coming up to me to take photos -- and Stepmother insisted that I oblige.  I was made to pose with strangers while friends and family snapped photos.  It seemed like an endless parade of teenage boys wanted to have their picture taken with me.  Most threw an arm around my shoulders.  A few grabbed my ass or surprised me with a kiss as their photo was taken.

With all the attention and posing for photos, I didn't even get to go on many rides.  We mostly went on the kiddie rides like Small World and Teapots and Dumbo.  Stepmother wouldn't let me go on the more exciting rides.

At 3:30, Stepmother brought me over the to the back of Cindarella's castle.  It was time for the costume contest.  I told Stepmother that I didn't want to watch the contest, but she wouldn't listen.  But then I realized that I wasn't watching the contest, I was entered in it.  I was up on a big stage while hundreds of cameras flashed and people clapped.  And to make a long story short, I won first place in the the teenage girl category. 

Before I knew what was happening to me, I was standing on a parade float standing next to the tennage boy winner -- a tall, dark haired boy named Eric who dressed up as Prince Charming.  We we instructed to stand on the float, to wave to the crowds, while holding hands!  I tried to find some way out of this embarrassing ordeal, but of course Stepmother wouldn't hear of it.

So there I was, dressed up in a pretty Alice in Wonderland costume, being featured in a parade going down Main Street USA at DisneyWorld.  Thousands of people were staring at me, clapping and cheering.  Of course, thousands of cameras and video cameras from all over the world were capturing my moment of shame.  And all the while I was holding hands with big tall teenage boy.  Oh dear!

And just when I thought my parade nightmare was ending, as we stepped off the float there was a crew and cameras from the Disney Channel there to interview me.  They asked me dozens of silly questions and I gave short, simple answers in my girlish voice as I tried to sink into the floor.  And then they asked, "So, Alice, what do you think of your Prince Charming?  Isn't he handsome?  It's every girl's dream to be with a handsome Prince Charming, don't you think?" 

Oh God! "Uhhh, uhhh, uhhh," I stammered, "Yes, I guess so."  I blushed a deep crimson.

After what seemed like hours, I was released from the TV filming.  Stepmother and I went back to the salon where I returned my costume and changed into my other clothes.  I was exhausted, humiliated and very angry with Stepmother for doing that to me.  At least this ordeal was over.  I was so happy that we were on our way back to the hotel.  That's when Stepmother said, "I was talking to Eric's parents and since the two of you looked so cute together, we've decided that we will all go out to dinner together tonight.  Isn't that nice?"

"But Stepmother!" I shrieked.

"Oh don't worry, Alice sweetie," Stepmother answered.  "I picked up a really cute dress for you to wear tonight!"

HAPPY HALLOWEEN!

Sissy's DisneyWorld Vacation -- Part 2

We got up early the next morning.  Today we were going to Epcot!  I asked Stepmother for the clothes that she had bought for me yesterday.  "Of course,"  she said, "I got you a nice shirt and some jeans to wear today."

Well, I opened the bag and was horrified by what I found.  "But this is a GIRL'S tank top.  And these aren't boy's jeans -- these are girl's capri pants!"

"No shit," replied Stepmother.  "Now put them on and let's go.  Or don't you want to go see Epcot?  And don't you want some more 'nightie fun' with me tonight like we had last night?"

"But, but, but,"  my head was spinning. "I can't go to Epcot dressed like a girl!"

"Of course you can.  No will know but me.  Now hurry up  and get dressed."

Well, I did as she commanded.  Once I had the tank top and capris on,  she put a little make-up on me and brushed out my hair.  "There!  You look lovely!  Just another teenage girl at Epcot.  Now let's go!"

We did go to the park and no one seemed to notice that I wasn't a girl.  In fact, it seemed like a lot of boys (and a lot of grown men) were staring at me.  Stepmother said that they were staring because I was so pretty and they were imagining having sex with me.  Yuck!

After a while I began to relax and focused less on the fact that I was dressed like a girl.  And Stepmother was really nice to me all day.  She must have taken 200 photos of me that day!  All day long she called me Alice and seemed to really be enjoying having me dressed up like a girl in public.

We were exhausted from our busy day when we returned to the hotel.  We took quick showers and I didn't protest when Stepmother told me to put on my nightie.  Stepmother brushed out my hair and did  my nails.  I enjoyed being treated so gently by her -- even if it was a little strange to be dressed as a girl.    After we turned off the lights, Stepmother once again started carressing me and whispering in my ear what a pretty girl I was.  I lay back as she gently stroked my stiff little cock through the silk of my nightgown.  In just a few moments she made me cum -- all over my nightie.  She raised the cum-covered hem of my nightie to my mouth and made me suck my cum off of it.  "That's a good little Sissy," Stepmother said.

The next day we went to Disney Studios.  This time Stepmother handed me a flimsy little sundress and some flip flops to wear.  I tried to protest but of course, in the end I did what Stepmother told me to do.

I was really nervous and uncomfortable wearing the little dress.  I felt like everyone -- especially all the boys -- were staring at me.  I felt half naked.  I worried all day that my skirt wouldn't stay down and everyone would see my panties. 

Stepmother and I had a wonderful time at the park.  She told me about a thousand times how cute and pretty and sexy I looked in my little flowered dress.  She took tons of photos and even some video of me having fun in the park wearing my pretty dress.

And of course, at the end of the day, Stepmother and I returned to our hotel for what she called "nightie fun."  I was in heaven.

The next day we were going to the Magic Kingdom...

Sissy's DisneyWorld Vacation -- Part 1

I was so excited that my Stepmother was going to take me on vacation -- to DisneyWorld!  I had always dreamed of going to DisneyWorld.  Our trip was planned for late October when I had a short break from school. 

I really don't like my Stepmother.  She is not nice to me.  Ever since she caught me once trying her clothes, she has insisted that I wear girls clothes at home whenever my father is away -- which is very often because he is in the Navy and is sometimes away for months at a time.  She says that I am a pathetic Sissy Faggot.  She makes me cook and clean and she beats me for making even a tiny mistake.  She made me practice my make-up, my voice, my walk -- everything -- so that now I can really look and act like a girl.  She hasn't let me get a haircut for nearly a year and now my hair is starting to get pretty long.

Anyway, I thought the vacation might mean that maybe my Stepmother was going to start being nicer to me...

On the day of our trip, the limo came to the house very early.  Everything seemed to be in a big, frantic rush to get out of the house.  Unfortunately, in our rush, it seems that my suitcase was left behind.  Stepmother was very, very angry with me, saying that it was all my fault that my suitcase was left in the house.  She slapped me hard across the face, calling me a "Stupid Sissy Faggot" -- right in front of the limo driver, who just laughed at my humiliating treatment.  There wasn't time to go home and get it so Stepmother said that she would have to get me some new clothes when we got to Florida.

When we arrived at the hotel and entered our room, I saw that it only had one big bed, not two smaller beds.  When I asked Stepmother about it she just said that this was the only room the hotel had available and that it wasn't a problem and that would just share the bed.  That sounded very strange to me...

I hung out in the hotel room while my Stepmother went shopping for some new clothes for me.  She seemed very happy when she returned.  We ate room service for dinner.  When it was time to get ready for bed, Mother noted that since I didn't have any pajamas I would have to borrow one of her nighties to sleep in.   She handed me  a pretty, clingy black silk nightie that was trimmed with lace.  I didn't argue because she had been so angry with me earlier.  I put it on and she gushed about how pretty and sexy I looked in it.  She insisted on putting my hair in a ponytail and taking some photos of me -- which she often did when she had me dressed as a girl.  She put the camera away and I climbed into bed. 

A few minutes later, Stepmother emerged from the bathroom -- wearing the exact same nightie!  That was so strange.  Why would she pack two identical nighties for a vacation to DisneyWorld?  I was beginning to think that my suitcase wasn't left behind by accident...

Stepmother turned off the lights and climbed into bed.  She snuggled up very very close to me, rubbing her hands all over my silk covered body.  She whispered in my ear that I was beautiful and that it made her excited to dress me up like a girl.  It made me very uncomfortable and frightened and confused to be cuddled and carressed by Stepmother like this.  But I was also getting excited from her touch.  My little cock became stiff and Stepmother wrapped her long fingers around it.  She stroked my cock and whispered in my ear, "I am going to start calling you Alice.  Cum for me now, Sissy Alice!"

And I did.

An Adopted Sissy Daughter

At first, I was so happy when I learned that Mother had arranged to adopt me.  She seemed like a very nice lady.  I hated living in foster homes.  Since I was smaller and skinnier than the other boys in the foster homes, I was often bullied and beaten. 

But I started to worry during the drive home from the adoption agency.  Mother kept saying things like, "You are such a pretty girl," and "I'm so happy that you are now my daughter," and "I'm glad your hair is already long..."  I wasn't sure what to do or say.  I didn't want to be rude to my new Mother.

But she when she wouldn't stop talking about me like that, I finally spoke up, "But I'm not a girl!" I shouted.

"Oh don't be silly, Mother replied.  "You ARE a girl!"

When we got home, Mother showed me to my new room.  It was decorated in pink and white, with pictures of flowers on the walls and dolls everywhere.  And the closet and drawers were filled with girl clothes.  Now I was getting pretty upset about this situation.  I protested again, saying that I was a boy and that didn't want to live in a girl's room with girl stuff and that I wanted her to stop saying that I was a girl.

Well, that was a big mistake.  Mother grabbed me and stripped off all of my clothes -- Wow! She was really strong.  She threw me over her knee and spanked my bare bottom hard for what seemed like an hour.  All the while she yelled at me saying, "Listen here, little missy.  I say you are a girl and that means you are a girl.  I don't care if you think you were a boy but from now on you (whack!) are (whack!) a (whack!) GIRL! (whack! whack! whack!)"

When she was done spanking me, she roughly shoved me off her lap and onto the floor.  "Now you just stay here and think about all this until I call for you."  She picked up my boy clothes off the floor and left my room. 

I had never been so scared or confused in my whole life.  As I lay there, naked on the floor, I started to cry.  I wasn't sure what I was supposed to do. 

About 20 minutes later, Mother called out, "Victoria dearest!  Come to my room!"

I was still naked.  I decided to grab a pair of pair a girls panties from the drawer and I walked to Mother's room.  When I entered, Mother was sitting at her vanity, also wearing nothing but panties.  Her huge breasts were on full display for me.  "Look at us," she chirped.  "We're both wearing panties.  We're twins!"

She walked over to me.  I was trembling and staring at the floor, afraid to look directly at her.  She wrapped her arms around me tightly and pressed me against her enormous boobs.  They felt so soft.  "I'm sorry I had to spank you, Victoria.  I hope you learned your lesson and never disobey me or disagree with me again."

I nodded in agreement.

"Good.  You are going to enjoy being a girl and being my daughter.  It will be a wonderful and exciting experience for you.  Together, we are going to turn you into a lovely young lady."

I gulped.  This was crazy -- but I kept my mouth shut.

"And very soon you will get to have your own big, soft breasts, just like mine.  Won't that be wonderful, Victoria?!" She said.