A Sissy and his Mother Have a Weekend Adventure -- Part 2

Janey finished doing his hair and his make-up.  He slipped on the dress I had bought him earlier that afternoon.  He looked simply stunning.  I was so proud of my beautiful sissy son.

We rode the elevator down to the restaurant.  As we crossed the busy hotel lobby, I was aware that everyone was noticing this striking, elegant and -- dare I say it -- sexy young lady as he walked past.  I'm sure Janey noticed that many heads were turning because of him.  

Unfortunately, the restaurant was very busy and we hadn't made a reservation.  The Maitre d'  suggested that we have a drink at the bar and "perhaps a table might become available."  We did as he suggested and stepped into the hotel's lounge. The bar was mostly full of men -- and it was very crowded.  When we couldn't easily find a seat, I started thinking about leaving.  But just then, two men slid off their bar stools and offered their seats to us.  


The men introduced themselves as investment bankers from out of town. They were stuck here over the weekend, they explained, because they were working on some big deal. The older one was a senior partner with their firm, the younger one was a junior associate.   They wasted no time in buying us drinks and chatting us up. The younger one seemed quite delighted with Janey and was working very hard at impressing him.  I could see that all of this attention was making Janey a bit uncomfortable but I was really enjoying the older banker's flirting.  He was quite charming and I was starting to have a lot of fun.  

After his second glass of white wine, Janey started to relax.  He seemed to get into the spirit of the moment and started to enjoy the young banker's overtures.  Janey laughed at the young banker's jokes and partipated more in the conversation.

More than an hour went by when I mentioned to the older banker that Janey and I had hoped to get a table at the restaurant but that we didn't have a reservation.  "Let me fix that," replied my handsome older banker.  He walked out of the bar and returned two minutes later.  "Our table is ready," he announced.

Apparently, my new banker friend was a VIP of sorts and when he wants a table, one is immediately made available.  Before I could react, Janey and I were being seated at a table with our two gentlemen admirers.  Janey was starting on his third glass of wine (and keep in mind, he is too young and shouldn't be drinking at all!) and he seemed to be OK with this unexpected turn of events.

Dinner with our two handsome bankers was lovely.  Both were charming and fun. Janey was a perfect lady and played his part perfectly.  Maybe too perfectly.  As dinner progressed, Janey and his young banker were whispering to each other and giggling.  After the salads were cleared, I noticed the banker had his hand on Janey's stockinged thigh -- and Janey didn't seem to mind.  And while we were waiting for dessert to be served, Janey and his admirer started making out -- right at the table!  I was quite shocked but I wasn't going to interfere.  And besides, it made it very natural for me to start a little canoodling of my own with my senior partner. 

As my banker was paying the bill, Janey and I stepped into the ladies room for a quick talk.  Janey was nearly bursting with excitement.  "Mommy, I think he really likes me!" he panted.  "He wants me to go back to his room with him.  What should I do?"  

"Absolutely not, Janey.  You've had too much to drink and you have no idea what you are getting yourself into," I replied.  I had never even dreamed that Janey would feel this way about a man, worked up in a girlish romantic frenzy like this. And what did he think was going to happen if he went up the banker's hotel room? "Why don't you and your new 'boyfriend' have another cup of coffee down in the lobby and I'll come back and get you in an hour.  That should give you some time to...get better acquainted."

So after Janey and his young admirer excused themselves to go to the lobby, my senior banker and I went up to his room for a quick roll in the sack.  I expect that he was married, but I didn't care.  I was super horny and he was great in bed.

After the hour was up I put my clothes back on and went down to the lobby.  There was Janey sitting on a sofa frantically making out with his new boyfriend.  I separated them and dragged Janey back upstairs to our hotel room.  

A Sweet Sissy Escort

This is a picture of me taken yesterday.  I am an escort and I work the promenade near the fancy hotels downtown.  My real name is Robert.  But when I'm working, everyone knows me as Rebecca.

Ever since my dad ran out on us, things have been really tough for Mother and me.  Mother isn't very healthy and she can't work.  Then a few months ago the bill collectors started calling and the bank said that they were going to foreclose on the house. That's when Mother told me that she needed my help.

"Mother!" I cried, "I don't want to do that!  How can you even suggest that I do that?!?"

"But Robby," Mother replied, "It's the only way.  If you don't do this, we won't have any money at all and we'll be homeless.  And without money for my medicine...I won't live very long."


When she said that I gave in. She explained that she had seen an ad on Craig's List. There was a man named "Mr. Pearl" who was looking for "girls to entertain successful businessmen."

"But Mother," I shrieked. "I'm not a girl!"

"Well, of course not.  But you are rather...girly. I mean look at you.  Look how skinny and delicate you are. Anyway, when I described you to Mr. Pearl, he sounded very interested in  meeting you."

I was horrified and ashamed by everything she said. But I agreed to meet Mr. Pearl if it would help her.

Mr. Pearl was indeed very interested in me. He said that until I came along, he only had real girls working for him. He thought that he would find MANY clients who were interested in me since I offered something a "little different." 



Mr. Pearl and some of his girls helped get me started. They showed me how to use make-up and gave me clothes that would make me look sexy and get noticed. They taught me about all the different sex things that clients would want to do to me. I started crying at one point when someone explained about "double penetration." I didn't believe half the things they told me were true -- until I started working.

That was two months ago. Of course it was frightening and disgusting at first. But I have sort of gotten used to it and I'm earning a lot of money to help Mother.

Since then I have been working the promenade five nights a week.  I walk around, wiggling my ass and trying to attract the attention of the men who are out looking for some action.  Even though I am dressed like a sexy girl, because of my short hair most men figure out that I'm a sissy whore. While most guys are looking to be with a real girl, a lot of guys are really into doing it with sissies like me. 

On a good night I might have five or six "dates."  Most of my clients are businessmen in town for conventions.  Those aren't so bad because the businessmen are mostly pretty polite and we can go up to their hotel rooms to do it.  But some men are rough and mean.  And sometimes I have to do it with men in the backseats of their cars or in the public bathroom in the park.  The worst are the bachelor parties when I have to do a bunch of guys at the same time.  I get paid extra but I really don't like it.

Last night was horrible.  My last client -- number five for the night -- was insane.  He choked me and slapped me hard about a hundred times while I was blowing him -- I thought I was I going to die.  When I got home at 4:00 in the morning I was going to tell Mother that I couldn't do this any longer.  But before I could say anything, Mother told me that her new medicine was much more expensive.  She told me, as if it was good news, that Mr. Pearl had agreed to let me work seven nights a week and days too!  I cried myself to sleep knowing that I would be forever trapped as a sissy whore.  

The Sissy Debutante Ball

Mother had been dressing her son Jimmy up as "Ginger" for years.  At first Jimmy had resisted but his mother was very strong-willed and Jimmy was weak.  Over time, Jimmy stopped fighting his feminization and accepted what his mother was doing to him.

"I had always wanted to have a daughter," Mother told him a million times. "But unfortunately you were born a boy.  But just because you were born a boy doesn't mean I can't make you into my daughter." 

So ever since he was a little boy, Jimmy spent most afternoons -- and every weekend -- dressed as Ginger. And while wearing his pretty party dresses and nightgowns, Ginger and his Mother would spend countless hours doing things that mothers and daughters do.  Mother taught Ginger how to do his make-up and his hair and his nails.  They would do chores around the house like cooking and cleaning and ironing.  At night they often watch chick-flicks together while wearing their pretty night gowns.

So Ginger was brought up to be a perfect little Sissy.  But Ginger was growing up and tonight they would celebrate the lovely Sissy lady that Ginger had become.  Tonight was the Sissy Debutante Ball!

Tonight, nearly fifty Sissies, aged 18 to 20, and their Mothers would celebrate the long and sometimes difficult journey of raising a son to be a Sissy.  Mothers from all over the country brought their lovely Sissy darlings to this lavish affair at a posh hotel in New York City.  

Ginger and his Mother looked heavenly in their coordinated, custom-made outfits.  Mother wore a tailored suit of beautiful golden silk jacquard. Ginger wore a long gown -- made of the same gold silk jacquard as her mother.  Ginger's gown made him look sweet and sexy at the same time. Ginger and his mother had spent most of the aternoon at the beauty salon. Their hair and make-up were perfect.

Even though he looked very beautiful, Sissy Ginger was so nervous as he and his mother rode the evevator down from their hotel room to the ballroom below.  Sissy Ginger didn't know what to expect. 


They made their entrance when the Master of Ceremonies announced their names over the speaker: "Presenting Sissy Ginger and his Mother, Lady Annette!"  The other guests clapped as Ginger and his Mother entered the room.  Ginger was quite stunned by the applause and by the flashes of cameras capturing his big entrance. They found their seats, Lady Annette at one of the Mothers' tables and Ginger at one of the Sissies' tables.

As Ginger introduced himself to the other Sissies, he noticed there were several other tables in the ballroom that were occupied by men. Ginger asked one of the other Sissies who the men were.

"Don't you know?" answered one the other Sissies with surprise.  "After dinner is finished and the announcements are done, the Mothers will all leave and go to another room for the rest of the evening.  That's when the men are free to talk to us and dance with us and..."

"And WHAT?" Ginger asked, somewhat panicked.

"Well, they can ask us to come up to their rooms with them, of course.  And you are not allowed to refuse.  That is all part of the Sissy Debutante experience.  Tonight we become real Sissy Ladies with the Gentlemen that pick us.  Are you saying that your Mother never explained this to you?"
Poor Sissy Ginger.  He nearly fainted when he heard this.  Of course Mother had never told him about all this.  He would have been too terrified to even come here tonight.  

Tears started to well up in poor Ginger's eyes.  "Here, take this," said one Sissy offering Ginger a Xanax and a glass of champagne.  "Just relax and remember that this is what your Mother wants for you.  You need to be brave and do what your Mother expects you to do."

The other Sissy was right, thought Ginger as he downed the pill and the champagne in a single gulp.  "May I have some more champagne?" asked Ginger trying to prepare himself for the frightening evening ahead.  "A lot more."

Sissy Gets Ready to go Out

Two months ago, my little sister had caught me dressed up in mom's clothes and make-up when she came home early one afternoon.  She said that she would tell mom and dad -- unless I did exactly what she said from now on.  I guess I had always been a bully to my little sister and now was payback time.

Since then, we've been playing "dress up" almost every night.  After dinner, we run up to her room where she makes me practice doing my make-up and styling the wig she made me buy.  She makes practice walking in high heels and sounding like a girl when I talk.

She told all her friends about what a sissy I was -- and how I was really cute when dressed up like a girl.  Tonight, my sister told me, was going to be my "coming out" party.  She was going to take me, along with three of her friends, to a fancy club downtown where they never check IDs of cute girls who want to go in.  I'm the only one old enough to have a license, so I have to drive.

Mom and dad went out early to go to a party so we spent most of the afternoon getting ready.  My sister picked out my outfit for the evening from mom's closet -- a fancy gold and white Lily Pulitzer dress and a pair of strappy high heels.  She helped me get my wig and make-up just right.

"Hmmm," she said with a smile while looking me over when we were done.  "You know, Michael, you really do look like a pretty girl.  I don't think any of the guys at the club would ever guess that you're really a boy when they start flirting with you.  Just be careful when they start feeling you up."

When she said that, I broke down into tears, panic suddenly overcoming me.  "Please don't make me do this!  PLEASE!"

"Oh for God sake STOP CRYING!," my sister yelled.  "You're ruining your make-up!  You are such a big sissy!  Get it together and fix your make-up before the girls get here!  NOW HURRY!"  She slammed the door and went downstairs.

I stared at my reflection in the mirror.  My sister was right -- I did look like a pretty girl.  And she was also right about me being a big sissy. I knew I had to obey my sister or she would tell mom and dad.  As I started redoing my make-up, I tried to imagine what it was going to be like, being in a fancy nightclub in a pretty backless dress, sexy stilettos and glamorous make-up, knowing that men would be trying to talk to me and buy me drinks and...other things.

"Michael!  I mean Michelle!" my sister yelled from downstairs.  "Hurry up!  The girls are here!"

I dried my tears and fought to calm myself down.  I fixed my mascara and finished putting on my bright red lipstick.  I grabbed my little clutch purse and headed down the stairs.

When my sister's friends saw me, they screamed with delight.  They all told me how pretty and sexy I looked.  They said that all the guys would be drooling all over me tonight.  I enjoyed hearing the girls say that I was pretty -- but talking about the men at the club made me feel  sort of sick to my stomach.

One of the girls said, "And when you're giving some guy a blow job tonight, be sure to swallow every drop.  You don't want to get any stains on  your mother's pretty dress."

The girls howled with laughter at that.  I almost started to cry again.

"Time to go, Michelle," my sister said.

A Simple Minded Sissy

Poor Sissy Gretchen.  His transformation had been particularly difficult.  He had resisted the process every step of the way.  He simply would not cooperate with the plans I had for him.  But I knew he would make an exceptionally pretty -- and valuable -- sissy once the transformation was complete.

Through a combination of drugs, hypnosis, electroshock and beatings, I was eventually able to break through his resistance and complete his conversion.  And I was right -- I was able to transform this young man into one of the prettiest sissies I ever made.

Aided by a daily dose of narcotics, Sissy Gretchen becomes a simple minded little sissy who no longer has any will of his own.  He will obediently follow any instruction given no matter how demeaning or disgusting.  That makes him the perfect sissy escort.  I have a long list of wealthy men who have no problem paying me thousands of dollars for a few hours with this gorgeous and completely docile sissy love doll.

At the end of every long day of sissy sex servitude, Sissy Gretchen has an unusual bedtime routine.  He strips off his pretty dress and slips into a sexy, sheer and very revealing baby doll nightgown. Then he allows me to put a ball gag in his mouth and to tie his wrists and ankles to the bedposts.  Sissy Gretchen falls asleep, content and mindless.  I leave his bedroom light on.

These bedtime preparations are required because during the hours before dawn, Sissy Gretchen will awaken as yesterday's dose of narcotics begin to wear off.  As his brain begins to refocus, he remembers who he was -- and what he has become.  I expect his mind is flooded, all at once, with images of his feminized self submitting to the disgusting demands of his many male clients.  The terror he experiences is amplified by seeing his own gorgeous sissy reflection in the mirrored ceiling above his bed, his enormous breasts barely concealed by his sheer baby doll nightie.  He writhes in mental agony on top of his bed, struggling to free himself from his lashings.  His screams muffled by the bright red ball gag in his mouth.

I allow this to continue to a couple of hours until I am ready to get out of bed and deal with poor Sissy Gretchen.  By then he is a wreck, overcome by his exhaustion and horror.  I stand above him and tease him.  "Oh, what's the matter sissy?" I might say.  "Don't you like staring at your sexy reflection in the ceiling mirror?  Aren't you happy that you are now a perfect sissy slut?  Didn't you have fun yesterday -- and everyday -- doing all those nasty things you did to all those men?"  It doesn't take much to get him to start sobbing.

Eventually I take pity on him I inject him with today's dose of narcotics.  He slips back into unconsciousness for a couple of hours.  When he awakens later, the episode he experienced just a few hours earlier will have been completely forgotten, as he begins another day of obedient sissy sex servitude.

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."

Blonde Sissy for Black Master

When the world middleweight boxing champ wanted to get his very own sissy, he came to me. He was a black man, amazingly strong and fabulously wealthy.

I transformed a young man into a perfect sissy sex toy for him.  Sissy Tammy's body had been forcibly feminized to perfection.  Sissy Tammy was petite, blonde and completely terrified of his new owner, who has made Sissy Tammy's life a nonstop nightmare.

Master enjoys using Sissy Tammy as his own living sex doll, forcing himself on his defenseless little sissy whenever and where ever he wants.  Master likes to pick his sissy up in his big strong arms and fuck him in mid air, roughly bouncing his sissy up and down, again and again, on his rock hard cock.  Poor little Sissy Tammy feels like he is going to be split in two every time Master rams his huge cock into his tight little Sissy pussy.  Sissy screams in pain with each thrust, but the sissy's sceams just get Master more excited.

After Master is done filling Sissy Tammy's ass with gallons of his hot cum, Sissy Tammy crawls between his Master's legs and carefully licks his Master's massive dick clean.  If Master gets hard again, then Sissy Tammy gets to swallow another load of his black Master's seed.  And when Master tires of having his enormous dick sucked, he lies down on his king sized bed for his nightly massage.  Sissy Tammy has been trained to expertly massage his Master's strong, muscular body.

Oh dear, it looks like the massage is making Master's dick hard again.  Get ready for another fucking, Sissy!

A Sissy Hooker

When the people at the "New York Transformation Institute" offered to finance my feminization surgery, I should have been more suspicious. But they showed me how beautiful I could become if I elected their very expensive "super premium feminization surgery" package.   I knew I couldn't afford it, but I was powerless to resist.

When the surgery was complete, I was indeed as beautiful as they promised me I would be. My face, my boobs, my hips -- everything was perfect and sexy. They even made my waist super skinny! It was all beyond my wildest dreams!  I wasn't just beautiful -- I was hot!

But now I was deeply in debt. I had no way to pay back the $85,000 I now owed the NYTI. But that was their plan all along! I am now an indentured servant -- a slave -- because I can't pay my bill.  And if I don't pay them back, they said they will kill me! 

I am forced to work for them as a sexy sissy hooker.  Everyday, I am dressed up in some skimpy, whorish outfit and made to stand behind the bus terminal waiting for men to drive buy that are looking for prostitutes.  Then I either give them blow jobs right in their cars or let them drive me to the motel near the warehouses.  The men I have sex with are mean and dirty and I feel sick everytime I have to let one of them cum in my mouth or on my face.

My doctor/pimp says that if I work really hard, I might be able to pay off my debt in fifteen years.  Until then, I will spend every day of my life as a frightened, cum-soaked Sissy whore.

The Sissy Behind the Curtain

"Martin!" my wife shouted, "Get out here.  NOW!"

My wife had caught me dressing up in her clothes a few weeks ago -- and she didn't like that one little bit.

"Don't be shy, Martin!" she continued.  "We all want to see how pretty you are."  My wife and her lover were waiting for me in the Master bedroom.  They both started giggling when she said that.

I had been dreading this moment.  During the afternoon, my wife had spent hours getting me ready.  First she did my make-up and pinned a curly brunette wig on my head.  Then she dressed me in a sexy red outfit including some strappy high heel sandals that she had picked out for me to wear tonight.  She even put some of her jewelry on me.



"WE"RE WAITING!" she yelled.

I reluctantly stuck my head through the curtain that separated the Master bedroom from the dressing area.  I saw my wife and her lover, both half naked, wrapped in each other's arms sitting on the bed.

"Come on now," my wife called.  "Come all the way out here.  Don't keep us waiting any more."








I tentatively pulled back the maroon curtain and stepped fully into the Master bedroom.

"OH MY GOD!" her lover shouted.  "I can't believe this!  What a Sissy!  He really does look like a girl!"

"Can you believe I actually married a Sissy faggot like that?" my wife asked.

"Now do that sexy dance I taught you," my wife commanded.  And with that, I began to sway and rock, wiggling my hips in a sort of burlesque dance.   "Oh yes!  That's soooo sexy!"  my wife yelled.  And with that, the couple on the bed broke down into fits of laughter.

After a few minutes my wife told me to stop dancing and to come stand next to the bed.  "Now you just stand there and watch while a real man fucks me."  As she said that, the two lovers stripped off the rest of their clothes.  My wife's lover was a big, muscular man with a huge cock.  I just stood there, wearing my sexy red lingerie, while he climbed on top of my naked wife and started fucking her.  I couldn't fight back the tears as my wife started screaming with pleasure, being fucked by such a masculine man. 

After they were done fucking, my wife sat up and looked at me with disgust.  "Aw, is the widdle sissy sad because he's feeling left out?  Well don't cry, sissy.  We have something very important for you to do.  Now get on your knees and clean my man's cock with that pretty sissy mouth of yours."

I did exactly as I was ordered.  As I wrapped my painted lips around this giant cock I realized my life would never be the same again.

New Sissies at the Beach

Last week I took my two newest Sissies for a day of fun at the beach.  It was a holiday weekend, so the beach was very crowded and my Sissies attracted a lot of attention!

These two fell into my clutches just a few weeks ago.  They are just at the very beginning of their transformations.  Their boyish haircuts are just starting to grow into more sissyish styles -- although I already dyed their hair to a prettier, more feminine color.  They are still very confused and frightened by their captivity and forced transformations.

My newest Sissies were horrified when they saw the outfits they would be wearing.  But their protests subsided after a few whacks with my hairbrush.

And aren't they absolutely darling!?!  I just loved dressing these two up in these identical sissy bathing suits -- with the matching sissy cover-up.  The high waisted panty (with an adorable little bow!) and the training bra tops are simply devine.  And the little pink heartsare just perfect for little Sissies.

I love this photo.  The Sissy in front is about to start crying as I just ordered him to take off his cover-up and let everyone see him in his pretty Sissy bikini!

Sissy Pets -- part 2

Sissy Timothy hated going to his ballet lesson.  He was in a class of 9 and 10 year old girls.  He was forced to wear a peach colored leotard and a ruffled tutu.  Master always watched his ballet lesson, enjoying Timothy's humiliation as well as ensuring that Timothy was trying his hardest to learn to dance.

After class ended, Master took Sissy Timothy to the mall to go dress shopping.  Poor Sissy Timothy was still wearing his leotard as they walked into the dress departmant at Macy's.  Master found a sales lady and explained to her, "My Sissy and I are going to take a cruise together and I would like to get him some cute dresses to wear to dinner.  You know, something sweet for a Sissy."

"I think I understand what you might be looking for," the helpful saleslady said.    She disappeared for a few minutes and returned with an arm load of dresses.  "Let's see if any of these will work."  She proceeded to hold the dresses up in front of poor embarrassed Sissy Timothy, while his Master commented on which ones he liked best.  Having Master's approval on three of the dresses, the saleslady grabbed Sissy Timothy by the wrist and dragged him back to the ladies fitting room.  And to Sissy Timothy's surprise, she joined him in the room and closed the door behind them.

"Now, let's get you out of that leotard," the saleslady said.  Sissy Timothy hesitated.  "Come, come now," the saleslady chided, "Nothing to be ashamed of.  No 'men' in here," she said with a grin and a wink.

Sssy Timothy's face turned bright red as he squiggled out of his leotard.  The saleslady couldn't suppress her laughter when she saw Sissy Timothy standing there in his training bra and Hello Kitty panties. 

Sissy Timothy tried on the first of the dresses, a short, floral dress with a mostly open back.  He almost started crying when he saw his reflection in the mirror and how completely sissified he had become.

"Oh, that's adorable!" the saleslady said.  Let's go show your...gentleman friend."  Again, the saleslady grabbed Sissy Timothy by the arm and dragged him out of the fitting room.

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.

A Sweet Sissy Nest

While some Sissy Trainers I know prefer to work with just one Sissy at a time, I prefer to train mine in groups of two or three.

I find that in groups, forcibly transformed Sissies form an odd and powerful dependence on one another.  A weird bond is forged among Sissies as their masculinity and ability to think for themselves is stripped away, replaced with fear, uncertainty, obedience and confusion.  My Sissies cling to each other like sweet little Sissy Sisters.

I force my Sissies-in-Training to do everything together -- eat, dress, bathe, accept punishment -- everything.  Here is a photo of my latest crop of Sissies-in-Training snuggled up close for their afternoon nap.  The twin bed that the three of them share becomes a cozy Sissy nest.  Isn't that sweet!

A Frightened Sissy

Poor, frightened Sissy Vicky.

His Master had just returned home and Sissy Vicky knew that he had been drinking heavily.  And when Master was drunk, he always got very rough with his little Sissy. 

Sissy Vicky greeted his Master at the door as he had been trained.  His drunk Master tore the dress off of his Sissy and started slapping the little Sissy around for no reason.  Then Master started to loosen his belt to use it on Vicky.  When Vicky saw this, he started to run.  Racing through the house, wearing just his bra and panties and his high heeled sandals, Sissy Vicky looked for someplace to hide.

Vicky hid in the guest room shower, hoping that his Master wouldn't find him there.  With some luck, his drunk Master would pass out before finding where his Sissy was hiding.

Just then, the Master kicked open the locked bathroom door.  "A Sissy NEVER runs away from his Master," he roared.  "Now I am VERY angry with you!"

Sissy Vicky started to sob, knowing that his enraged Master was going to beat him mercilessly.

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.

Sissy Birthday Surprise

My Mistress seemed to go to extra effort when she dressed me this afternoon. She had me try one several dresses until she decided that she liked how this one looked best. My Mistress seemed so happy and excited as she did my hair and my make-up. She absolutely giggled with delight as she pinned the big pink hat to my tresses. My Mistress had told me that she was planning a fun outing today to celebrate my birthday.

She was in such a good mood that I worked up the courage to ask her a question. "Mistress," I asked softly, "where are we going today?"

"Oh, you are a curious little Sissy, aren't you?" she replied, "Why don't you try to guess where we're going."

"Well," I replied tentatively, "based on how I'm dressed, maybe we are going to the Smithtown Garden Show, or maybe we are going out for tea, or to a matinee..."

"Oh my goodness, no!" exclaimed my Mistress. "There's a double header scheduled today and you're going to spend the afternoon at the baseball stadium. The stadium will be packed with rowdy, drunk fans. Doesn't that sound like fun?"

I nearly fainted. "Oh please, PLEASE, don't make me sit in the stands dressed like this. I'll look rediculous. Everyone will stare and laugh at me."

"Oh don't be silly. You look lovely. The men in the stadium will enjoy looking at you. But I didn't tell you the best part -- during the seventh inning stretch, the Jumbotron cameras will focus on you while the announcer leads the crowd in singing, "Happy Birthday, Sissy Tiffany!"

Sissy's First Date

Little Sissy Wendy had spent most of the aftenoon at the salon being prettified to sissy perfection for his big night.



Sissy Wendy's Mistress had posted ads on the Internet to find a boyfriend for her exquisitely feminized Sissy.  Poor little Sissy Wendy is disgusted and terrified about having a male lover.  But this is what Mistress wants and she doesn't care about Sissy Wendy's silly feelings.



As the door bell rings, Mistress reminds Sissy Wendy that he is to be charming, obedient and submissive on his first date with a man.