A Sissy Begs for Forgiveness

"Oh, please, Stepmother," I begged.  "It won't happen again.  I am so sorry.  I promise.  Please don't punish me.  PLEASE!"  I stood in the middle of the room, perched in my towering high heels, my manicured hands clasped together as I repented for my failings.

"SILENCE!" Stepmother shouted.  "You are NEVER to speak unless spoken to!"

I lowered my eyes to the floor, now terrified that I had made my terrible situation much worse.

"Look at you, you pathetic sissy.  I can see right through that ridiculus outfit you are wearing.  Only a real sissy slut would dress like that.  Aren't I right?"  she asked.

"Yes Ma'am," I replied softly, even though we both knew that she picked out all the outfits I was allowed to wear.

"You broke a very expensive teacup when you were washing the dishes today and that sort of misbehavior must be punished.  So what will it be, sissy?  The paddle or the dildo?"

Oh no, I thought.  This was going to be bad.  Even though my bottom was still raw from my last spanking, I really hated being punished with Stepmother's strap-on.  "The paddle," I said.  "Please," I quickly added.

I pulled down my panties, lifted my billowy skirt over my waist, and lay across Stepmother's lap.  But before she started paddling my bottom, she called out loudly, "Tiffany, please come in here!"

And in walked Tiffany, my stepsister.  Oh God!  What was Tiffany doing here?  It was so humiliating having my much younger stepsister seeing me like this, laying across Stepmother's lap, with my skirt hiked up and my bare bottom sticking up in the air. I started to try to squirm away, but Stepmother is so much stronger than me and she held me firmly in place.  "Be still, Sissy!"  Stepmother growled.  Tiffany roared with laughter seeing me like this.

"You see, Sissy," she explained, "I decided that it was time to show Tiffany how to discipline you.  That way we can ensure that you will always be as obidient to her as you are to me.  Now go ahead, Tiffany.  Do it just the way I explained."

Tiffany picked up my punishment paddle and waved it in front of my face.  "Kiss it, Sissy," she said with an evil grin.  I did just as instructed, knowing that to protest would be very unwise.

And with that Tiffany began to administer 20 stinging blows to my bare bottom, while her mother held me firmly in place on her lap.  After the first ten, Stepmother said to Tiffany, "Now dear, if you don't spank him harder than that, how will he ever learn his lesson?"

Tiffany put all her strength into the next ten blows.  I could hear her laughing as she abused my bottom.  Tears were pouring down my face as the pain and humiliation were unbearable.

When Tiffany was done with my beating, Stepmother started rubbing my burning bottom.  "Have you learned your lesson, Sissy?"

"Yes Ma'am," I whimpered.  "I'm very sorry. I learned my lesson."  I started to get up from Stepmother's lap.

"Not so fast, Sissy," she said with a sneer as she kept me pinned to her lap with her strong arms.  "You didn't thank Tiffany for teaching you a lesson and helping you to become a better Sissy."

I choked back my tears and forced myself to say, "Thank you Tiffany for teaching me a lesson and helping me to become a better Sissy."

Stepmother administered a sharp bare-handed slap to my bright red bottom and snarled, "From now on you will refer to her as Mistress Tiffany, do you understand?"

"Yes, Stepmother.  I understand.  I am sorry for my inpertinence, Mistress Tiffany."

"That's more like it," Stepmother said with a satisfied smile.  "Now get yourself cleaned up and get started on making dinner."

Young Sissy Created for Older Men

Stepmother was so excited!  Tonight, Sissy Suzette was going out on his first date -- with a MAN!

Sissy Suzette's cruel stepmother, Mildred, had been transforming her stepson Stanley from a normal teenage boy into a feminized plaything for older men.  Two years ago,  Stanley/Suzette's father ran off with another woman, leaving Mildred to care for Stanley on her own.  She decided that she would take her revenge on her husband by destroying his only son.

And so, after two years of hormones, strict training and brainwashing, it all came down to this.  Poor Sissy Suzette!  He is so terrified about being sent on a date.  He was close to tears this afternoon as Mildred helped him with his hair and make-up.   

Mildred had posted Suzette's profile on Match.com, including some sexy, glamourous photos.  The profile said Suzette was 19 years old -- and that she was interested in dates with much older men.  Well, within days it seemed like millions of men in the area eagerly responded.  Mildred was delighted when she discovered that she could subject poor little Suzette to a limitless number of romantic encounters with different men.

Mildred carefully selected outfits for Sissy Suzette that were both sexy and classy.  A rigorous diet cimbined with a little padding in all the right places gave Sissy Suzette the alluring shape of a pretty young woman.  And with relentless training, Sissy Suzette could now talk and sit and eat and walk exactly like a girl. 

It was time for Sissy Suzette's first encounter.  The date was arranged at a french restaurant downtown.  Mildred sat at a nearby table and enjoyed the show!  Suzette's date, a 50 year old executive, was practically drooling throughout dinner, ogling the pretty young thing sitting across from him.  Sissy Stanley flirted with the older man as his stepmother had trained him. 

Watching the bizarre scene unfold was getting Mildred excited.  She even felt her panties become damp as she saw Sissy Suzette's date place his hand on Suzette's stockinged knee under the table.  This was going even better than she had hoped!

When dinner was over, Mildred followed the pair out to the parking lot where the two were passionately making out, the older man pressing her stepson against the man's BMW as he aggressively kissed the pretend girl.  After a few moments, the two climbed into the man's car.  Soon the two would be back at the man's house, where Sissy Suzette would pleasure his date with his soft manicured hands and his red glossy lips.  As Mildred watched them drive off, she had an orgasm imagining her nephew Stanley sucking on his date's cock and making him cum. 

Mildred rushed home to arrange many, many more dates for her sissy nephew.

My Sissy Assistant -- Part 2

Well, that first business trip with my little Sissy stepson as my assistant worked out so well, that he is now my full-time secretary!  He now comes wth me on every business trip I make.  He makes all my travel arrangements, takes notes in meetings, carries my suitcase, everything.  He even helps me get dressed in the morning.  I know he hates being paraded around in public all dolled up in chic little dresses and sky-high heels.  But he be behaves and follow my every order because that's how he's been trained -- and because he is simply terrified that someone will discover that he isn't really a cute little girl but actually a pathetic Sissy boy.

And because he is so pretty now, everywhere we go men take a lot of interest in him.  Waiters in restaurants, taxi drivers, strangers in airports, it doesn't matter.  If they have a dick, they start hitting on him.  It is hysterical!  The poor little Sissy is so embarrassed and mortified by the idea of men flirting with him.

But of course, this is more than just entertainment for me.

On my business trips, I often have dinner with businessmen trying to get me to place an order with their companies.  They wine and dine me.  Sometimes it's fun but mostly it is just business.  But now I make my Sissy stepson come out to dinner with me.  I've bought him a dozen sexy going-out-to-dinner dresses that I make him wear.  Well, the businessmen just LOVE it!  They can't stop drooling over my stepson, especially when I have him dressed so glamorously.  And after a few drinks, these men usual start flirting with my stepson.  They think I don't notice, but some men will reach under the table to place a hand on my Sissy's stockinged knee or to stroke his silky thigh.  

And that creates all sorts of opportunities.  More often than not, these businessmen will invite my Sissy stepson up to their hotel rooms for a "nightcap."  My little Sissy knows he has to eagerly accept these invitations -- even though he is disgusted by what awaits him.  But he is both obedient -- and well trained in various "womanly arts."

As soon as he arrives in their hotel rooms, the little Sissy starts making out with my businessmen like a horny little tramp.  Then he drops to his knees to  demonstrate what an expert little cocksucker he is.  He hungrily swallows every drop of cum that is shot into his mouth.  And then he licks the men's dicks until they are perfectly clean.  

And do you want to know what the best part of all this?  The businessmen like my little Sissy assistant so much, they usually give me an extra 5% discount on my order -- as long as I promise to let them see my Sissy assistant again! 

My Sissy Assistant -- Part 1

After my husband ran off, I started having awful problems with the rotten stepson I was left with. I travel a lot on business (I am a fashion buyer for a famous department store) and he was getting into all sorts of terrible trouble when I was away. A friend suggested that I have him feminized because sissified gurly boys are so much better behaved.


Well that's what I did.  I sent away to have him transformed.  It took about a year and the results were amazing. Not only did I now have a cute, feminine "stepdaughter," but he was now completely obedient and compliant.  He would do anything I said without any reservation or complaint.  He was completely broken.  I understand that he had been subjected to some rather strict behavior modification during his year long conversion.


I was, of course, delighted. I could now leave my femmy stepson at home while I traveled without worrying.  When I would return home from a trip, my home would be spotlessly clean and he would greet me with a delightful little curtsey to welcome me home.


During one particularly busy period, I was falling behind in my paperwork and I asked my Sissy stepson to do some filing in my home office.  He did it perfectly.  I soon had him keeping track of my appointments and filling out expense reports for me.  I suddenly had my own personal Sissy Assistant!

I decided to take my Sissy with me on a two-week west coast trip and it worked out wonderfully!  No one was surprised to see a senior buyer like me followed around by a sweet little assistant.  But of course, my Sissy had to dress the part.  So I bought several fashionable outfits for him to wear.   Here are a few of the dresses I had him wear on his first trip with me as my secretary.  Doesn't he look adorable!













I knew he hated it, but he was too well trained to complain.  At first, I know he was scared that someone would find out that he was not a pretty girl but actually a sissified boy.  And I constantly threatened him that someone would figure out his secret unless he behaved with girlish perfection.  But of course, his feminization was so complete that no one would ever guess he wasn't a girl -- unless you pulled down his panties.

Rotten Stepson becomes a Perfect Sissy

When I decided to have my stepson transformed into a feminized, obedient Sissy, I had no idea where this would lead.  Mostly I was sick of his rude behavior, his back talk and his laziness.  It was such a relief when I had him sent away for his year-long transformation.

When I first brought him home I was totally amazed by his transformation.  Physically he had been completely changed.  He was now a pretty, delicate, completely feminine little Sissy.  His hair was long and had lovely coppery highlights.  He had lost twenty or thirty pounds -- maybe more -- and was developing the sweetest little breasts.  Everything about his body and appearance was now so girlish.  But his physical transformation was nothing compared to his mental transformation.

He was now utterly and totally obedient to me.  He seemed to have no desire other than to please me. He was such a delight to have around the house.  He needed no instruction to keep the house spotlessly clean, to prepare my meals, make my bed -- everything!  I let him help me dress and undress me and even bathe and massage me. He would never speak unless spoken to.  When I would enter a room, he would stop whatever he was doing, lower his eyes to the floor, and curtsey to me.  It was marvelous.

But over time, I developed a strange attraction to my litle Sissified creation.  He was so devoted to me and took such good care of me.  I soon started to enjoy my Sissy in more...intimate ways.   I had my little Sissy joining in my bath and in my bed.  I enjoyed running my hands all over his soft little body.   I enjoyed pressing his naked body against mine, letting him play with my big boobs while I played with his tiny little titties.  And best of all, I loved feeling his sweet little mouth and tongue on my pussy.  I hadn't realized how thorough his training had been!

Who knows?  Maybe I'll get my Sissy stepson some big sexy breasts so he can be more like me.  I bet he'd like that!

A Sissy for the Entire Family to Enjoy!

When my Father ran off with another woman two years ago, my Stepmother became crazed with anger.  I knew that she had never really liked me and now that Father was gone, I knew that I would bear the brunt of her rage.  


I remember the day that she decided that she had too many boys to raise.  You see, she already had four sons of her own, all of whom were big and strong and brutish and mean.  Over dinner one night, Stepmother announced that from that moment on, that I would be a girl, her "daughter".  She said that I was already "girlish" to begin with and that I was probably a secret "sissy faggot" anyway, so turning me into a girl would be easy.  Her four sons roared with laughter when she said this, while I ran from the kitchen in tears and hid in my room.  I was so scared of what was going to happen to me and so ashamed to be called names like "Sissy" and "faggot" in front of my half brothers.

My life changed completely.  From that day forward, I was continuously with my Stepmother.  I even slept in a small cot in her bedroom.  I no longer went to school.  All of my old clothes were thrown away.  I was allowed to wear only my Stepmother's old dresses.  I even had to wear her underwear and her high heeled shoes.  My days were spent in dresses and make-up, cooking for and cleaning up after my four half brothers.  Stepmother punished me harshly if my chores were not done perfectly or if my behavior was not completely feminine.  I was taken to see several doctors and given shots and pills and soon I started to notice changes in my body.

After a while, I didn't mind so much the tiring and demeaning chores I did all day.  But I dreaded the end of the day when the boys would return home.  They relentlessly teased me, calling me names, slapping and pinching my butt, grabbing and squeezing my growing breasts.  It was awful.

Whenever Stepmother and the boys went into town to go to a restaurant or see a movie, I would be left behind.  Stepmother said that I couldn't be trusted to behave properly unsupervised, so I would be tied up in the storage room over the garage whenever they went out. 

Tonight, Stepmother was taking the boys into town for dinner.  Because Stepmother was angry with me for something I did or didn't do, she made me take off my dress and undies before being imprisoned in the garage attic for the evening.  The boys loved staring at me being paraded through the house naked by their mother!  The attic was so cold and uncomfortable.  I sat there for hours with nothing to do but to think about what a nightmare my life had become.

But at least tonight, I was alone.  That was better than being groped and abused by the boys.  Whenever Stepmother was out -- or any other time the boys could get me alone -- they would do things to me.  And make me do things to them.  It was horrible and disgusting and painful.  The boys used me a like a real girl, pumping gallons of their hot, sticky cum into to me and all over me.

The oldest one, Carl, was the worst.  He was mean and stupid and huge.  He not only liked to fuck me, but he really enjoyed hurting me at the same time, slapping me, pulling my hair, twisting my arms up hard behind my back.  Well at least the boys were out tonight.  Or so I thought.

That's when I heard Carl's heavy footsteps clumping up the stairs to the attic.  "Guess what, Sissy?  I came home early tonight.  So you and I can have some fun together and nobody will bother us.  Won't that be fun?"  He was already unzipping his jeans as he approached me.  I scrambled to me feet in a useless attempt to get away from him, but my hands were tied and I had no where to go.

He grabbed me with his huge rough hands.  He squeezed my boobs really hard and licked my face all over with his disgusting, drooly tongue.

"You are all mine tonight, Sissy," he hissed into my ear as I started to cry.

 

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.

A Sissy's Education

"Quit your pouting and change your attitude right this second, missy," scolded my stepmother.  "Look at the time and you're not even dressed yet!"

"But you promised!" I cried.  "We had a deal.  You said I could go to college in the fall if I let you treat me like a daughter all summer.  Well, I did everything you asked.   I travelled all over Europe with you pretending to be mother and daughter.  I let you dress me up like a girl every day.  I even learned how to do my hair and make-up like a real girl."

"Wasn't that just delightful," she replied.  "And you looked so cute in your swimsuit on the beach in Capri..."   

"And," I continued, "I think you've been putting female hormones in my food."

"You figured that out, did you Einstein?" my Stepmother sneered.  "What gave it away?  Was it those B-cup boobs or the fact that your little 'thingie' doesn't get hard any more?  Now hurry up and put one your dress.  The car will be here soon to take us to the airport."

"But I'm not going!" I screamed.  "You can't make be go to a girls' finishing school!"

"Oh, I can and I will!" my stepmother shot back.  "Now you listen to me you little faggot sissy.  I know you like to dress up like a girl.  I know you've been trying on my things when I'm not home.  Don't try to deny it."

I hung my head in shame.  "We've already discussed this a hundred times," I said, defeated.  "Yes, I like to wear girl things occasionally.  I like to pretend I'm a girl once in a while." 

"Well, then, what's the problem?  I'm letting you live out your dream and pretend to be a girl all the time.  I'm even willing to spend a lot of money to send you to school to be the very best girl you can be!  Now one more word out of you and I will tell your father that you're a little sissy that likes to dress up like a pretty girl!"

Oh no!  Anything but that.  My stepmother held the trump card and she knew it.

"Oh my," my stepmother said, " the limo is already here.  Get your dress on and let's get you to school."

A Stepmother's Sissy

After my father's death, my evil stepmother sent me away to feminization clinic in Brazil.  There, over the course of 18 months, I was forced to undergo a total transformation from a normal teenage boy to sexy submissive sissy.  The feminization clinic was part hospital, part bizarre finishing school and part hellish concentration camp.


I was awakened extra early today and taken to the salon, where over the course of several hours my hair and make-up were done in a very glamorous style.  Then I was brought back to the Administration building where my trainers dressed me in this very fancy lingreie. 

As several bracelets were slipped on my wrist, I heard my stepmother's voice coming from the next room.  I had not seen her since she had imprisoned me in the clinic a year and a half ago.

"That's right, Sissy, your Stepmommy is here.  She can't wait to see what we've done to you!  Time for your big debut," one of my trainers said with a cruel smile.

"Well hurry up and get out here!" my stepmother commanded from the next room.  "Don't be shy -- no reason for my new stepdaughter to be bashful in front of her stepmother," she cackled.

I was frozen with fear, horrified by the idea of parading aroung in front of her in my bra and panties, my complete sissification on full display.

"Get out there and behave yourself -- or else," the trainer threatened, brandishing the cattle prod he always carried. 

I swallowed hard and braced myself for the humiliation that awaited me.  I nervously parted the beaded curtain that hung in the doorway and made my entrance to the other room.  There was my horrible stepmother, seated on a sofa snuggled up close to a man I had never seen before.

My stepmother squealed with delight when she saw me.  "Oh my Gawd!" she exclaimed.  "It's even better than I could have dreamed.  Look at you, you pathetic sissy faggot.  What a little sissy slut you must be, prancing around in your girly undies for everyone to see."

"Isn't this wonderful, Roberto," my stepmother said to the man next to her,  "Now that my loser stepson is gone forever, I will inherit all of his father's millions.  We are rich, Roberto!" she said giving him a big hug.

"Well, time to go home Sissy.  Today you start you new life as my personal handmaiden, my own fulltime servant tending to my every need.  Won't that be wonderful?" she teased.

"We will dress her and bring her to your limo," the trainer helpfully offered.

"Oh heavens no," my stepmother replied.  "She doesn't need clothes.  She looks so lovely just the way she is.  Come along Sissy, get in the car.  A new life awaits!"