You Sissies Will Be Punished!

 

Sissy Madison's Vacation -- Part 1

Every schoolboy loves summer vacation.  But nobody looks forward to summer vacation as much as Matthew. That is because Matthew is a Sissy. And Matthew's Mother lets him be "Madison" all summer long!

In the past, Matthew mostly stayed at home during the summer, enjoying his free time wearing pretty dresses, high heels, jewelry and purfume around the house. Mother was always delighted to spend time with her sissy son, and encouraged him to be as feminine as he wanted to be.

Last summer, Matthew and his Mother did something new. They went on vacation to southern California together as mother and daughter for two weeks! As two ladies they did everything that tourists do in and around LA. Matthew even visited Disneyland as Madison which was great fun.

During their last few days in California, Mother suggested that Madison try wearing a ladies swimsuit and go to the hotel pool. Madison didn't have any swimsuits of his own, so Mother let him borrow one of hers. Madison squeezed himself into Mother's blue and white sheath suit. Mother carefully positioned Madison's breast forms into the cups and used a little make-up to give the appearance of some cleavage.

At first, Madison was nervous about going down to the pool in nothing but a skintight swimsuit. He felt so exposed -- practically naked. And yet he was thrilled by his own reflection in the mirror. After another hour of ensuring that his lipstick, his hair, his nails were all perfect, he worked up the courage to head down to the pool. He slipped on a pair of Mother's high heeled sandals, grabbed a towel and together they rode the elevator down to the pool level.

They found two lounge chairs near the deep end of the pool. Poor Madison was still so anxious about being in public in a ladies swimsuit that Mother ordered him a pina colada, which seemed to help. After some time -- and a second pina colada -- Madison started to relax. He began to see that his secret was safe even wearing nothing but a ladies swimsuit.  

And the more Madison could relax, the more he enjoyed the experience of being one of the pretty girls lounging around the pool, his soft pale skin exposed to the sun and to the breeze and to the eyes of all the other hotel guests. Madison wasn't aware of it, but Mother noticed that some of the men around the pool were staring -- or maybe leering -- at her sissy son.


Since that first experiment was so successful, the next day Mother suggested that they do it again. This time Madison  would wear Mother's black sheath suit. Together they worked to ensure that everything was prefect and that Madison looked like just another pretty girl going for a swim before they left their hotel room.   

This time Madison was much more confident. He knew he looked pretty and feminine in Mother's swimsuit. 

After lounging by the pool for an hour, Mother suggested that they walk to the cafe by the marina for lunch. Madison slipped on Mother's sandals and off they went. As they walked, this time both Mother and Madison became very aware of the stares he was getting, especially from the men they passed. This attention from strange men made Madison a bit uncomfortable and nervous -- but it also felt flattering and a bit exciting...

As they ate lunch, Mother announced that she had already been thinking about next summer.  Since this two week "Mother-Daughter" vacation had been so much fun, Mother said that she thought the two of them should do it again next summer.  But instead of just going away for two short weeks, she thought next year they should go away, to Florida, for six whole weeks.

Madison, of course, was delighted by this idea. He leapt from his chair and gave his Mother a sweet sissy hug! 

Dr.Thompson's Sissy

I do not like being owned by Dr. Thompson. But I am trapped. I am now Dr. Thompson's Sissy Tabitha.

It started last October, about eight months ago, when I visited Dr. Thompson, the school counselor. I was confused and worried about my urge to crossdress. I felt that I needed to talk to somebody and Dr. Thompson seemed kind and willing to talk to me. When I started talking, Dr. Thompson appeared very interested in hearing about my problem. He asked me dozens of questions and gently urged me to describe all of my crossdressing experiences and my sissy feelings in great detail. At first it was embarrassing to reveal my secrets, but Dr. Thompson was persistent and eventually I opened up and shared everything -- absolutely everything.

What I didn't know then was that Dr. Thompson was recording the interview with a hidden camera and microphone.

"Well, Timmy," Dr. Thompson said as the two hour meeting concluded. "You really are quite the little sissy faggot aren't you?" Dr. Thompson's tone and words had suddenly turned harsh and mean. "Here's what we're going to do. You see, I recorded everything you just said -- sound and video -- and unless you want me to share this with everyone you know, you're going to do everything I say. Do you understand?"

I was so shocked that I couldn't even respond.  That's when Dr. Thompson slapped me hard across the face. "I asked you a question, sissy! DO...YOU...UNDERSTAND?"

I finally nodded and said that I understood.  And that's when Dr. Thompson started taking over my life.

Dr. Thompson convinced my parents that I had some kind of learning diability and that I needed to have "special tutoring" every weekend. In reality, Dr. Thompson was arranging to have me be his very own weekend sissy captive. Instead of attending the special classes he described to my parents, I have to go to Dr. Thompson's house every Saturday on Sunday morning and spend the entire day as Dr. Thompson's sissy plaything.



As soon as I arrive, Dr. Thompson orders me to strip out of my boy clothes and then he begins the process of dressing me up like a girl. Dr. Thompson has an enormous collection of girl's clothing -- I guess I am not his first sissy. He spends several hours supervising me as I transform into Tabitha, ensuring every detail conforms to his very perverted and very precise desires. He watches me as I slip on a bra and panties, as I do my make-up and make my hair look pretty. My outfit for the day depends on his mood. Sometimes he has me put on a frilly party dress. Other times he dresses me up in a sexy lady outfit. Some of the clothes are really uncomfortable, like this one. The stockings and panty are made of a really tight rubbery material and he laces the corset so tight that it is hard to breathe.

Once I am all dressed and my face covered with make-up, Dr. Thompson starts ordering me around. Usually it starts with me making his lunch.  Then I have to tidy up his home -- vacuuming, dusting, washing windows, doing his laundry. After he tires of watching me scurrying around like his private maid, he tells me to sit next to him on the couch.  Then he starts feeling me up and kissing me.  I have to sit on his lap, feeling his hard dick poking me through his trousers.  Eventually he takes me by the hand and leads me back into his bedroom where he does terrible things that I can't even talk about.  And all the while he takes photos and videos of me. Then, as evening approaches, he orders me to clean off my make-up and to change back into boy clothes so I can go home. 

This went on all fall and all winter.  I dreaded every weekend but at least the end of the school year was approaching. I figured I would be free from Dr. Thompson's clutches, at least during the summer until school started again.

But those dreams were crushed.  Dr. Thompson spoke to my parents and convinced them that there was a special summer camp for children with my "learning disability." He even managed to get them to pay him $3000 in "camp fees."  But of course, there was no summer camp. Dr. Thompson had just arranged to have me as his full-time sissy travelling companion for five weeks.

Here's a photo of me taken during our long summer vacation together.  I am kept dressed as a girl 24/7.  He makes me wear fancy, silky dresses and high heel shoes everywhere. He even took me to a beauty salon for have my hair and nails done. He enjoys taking me out in public -- restaurants, shopping malls, sightseeing, even on airplanes -- knowing how scared and uncomfortable I am being paraded around like this. If anyone ever asks, he says that I am his daughter. I have to call him Daddy when we're in public.

But when we're alone in our hotel room, we are no longer "father and daughter." He gets very excited by making me look and act like a girl in public. So when we're in the privacy of our hotel room, he becomes a crazed sex monster. He fucks me over and over and over, until he falls asleep. Then it starts all over again the next day.

I have no hope of escaping from this sissy nightmare!  

Sissy Training -- the Final Lesson

Unless a client specifically requests that his new sissy be delivered as a virgin, I always arrange for my sissy creations to have one final important "lesson" before I consider my transformation work to be complete.

My sissies have to submit to a "lesson" in sissy lovemaking given by my good friend, Mr. Rhino.  Mr. Rhino is an enormous and strong black man with the biggest cock I've ever seen.  Seriously,  it's like a baseball bat!

The sissies know what is expected of them, even though they are scared half to death. They are to submissively lie on their backs and allow -- no, invite -- Mr. Rhino to fuck their tight little sissy pussies.  And despite the agonizing pain they experience, they are expected to pant and moan like the little sissy whores their new Masters will want them to be.

Here Mr. Rhino is giving Sissy Sally his final lesson.  Poor Sissy Sally was close to tears as he lay on the bed watching Mr. Rhino undress, exposing his monster dick.

But here's the best part.  When I have other sissies-in-training in my house, I make the more junior sissies sit on chairs next to the bed, watching their more senior sissy sister get his fucking lesson.  It's great fun to watch the junior sissies as they sit and watch in horror. Some burst into tears watching the fucking show as they all know that within a few short months, they will be receiving the same special lesson from Mr. Rhino and that giant black battering ram he has between his legs.

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!

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.

After School Sissy -- Part 3

Last Friday afternoon, when I came home from school, I went straight to my mother's room to do my make-up and put on one of her dresses like I do everyday.  As soon as I was satisfied that I looked pretty and girlish enough, I got busy on my chores before it was time to start making Stepfather's dinner.  As I was dusting upstairs, I went into my bedroom and discovered that my bed was gone.  When Stepfather came home I asked him what happened to my bed.

"Oh, I decided that you wouldn't be needing that old bed any more," he said.  I didn't understand what that meant, but I know he doesn't like it when I ask a lot of questions, so I let go.

After dinner, we went to the den and I climbed onto Stepfather's lap like usual to watch TV.  He wrapped his big arms around me, and started stroking me through the satiny dress I was wearing.  But after just a few minutes he let out a big yawn and announced that he was tired and wanted to go to bed.  "Come with me," he said.  "I have something to show you."

He took my hand and led me up the stairs to his bedroom.  I noticed that one of my mother's nightgowns was laid out on his big bed. 

"I want you to put that on," he said.  I knew better than to argue, so I picked up the silky nightie. 

"Okay," I said.  "I'll take this to my room and I'll try it on."

"No," he replied.  "You can change right here."

So I unzipped my dress (I mean mother's dress) and let it fall to the floor.  Stepfather seemed to enjoy watching me as I did this.  I unlaced my corset and pulled off my stockings.  I was about to take off my bra, but Stepfather said to keep it on.   While I was undressing, Stepfather started rubbing the front of his pants with his hand and was breathing hard.

I carefully pulled the silky nightie over my head, being careful not to mess up my wig or make-up.  The nightie was extremely feminine and sweet.   It had little ruffly cap sleeves and was trimmed with several ribbons and bows.   "Walk around," Stepfather instructed.   "Yeah, that's nice," he said as I paraded around the room. 

After a few minutes he handed me another one of mother's nighties.  "Here," he said.  "Try this one on."  I did as he instructed.  I modeled several nightgowns for him that evening.  He decided that he liked the one I tried on last the best.  It was soft pink with white applique flowers trimming the neckline. 

"Yes," he said.  "Keep that one on."  He kept staring at me, his hand still rubbing his erection through his pants.  I felt so exposed just standing there in th sheer nightie.  I held onto the back of the chair while he continued to stare at me. 

After a few minutes, he came out of his trance.  He said that he was going to go to the bathroom, and that when he came out, he wanted the lights dimmed and the candles lit.  I didn't like where this was going but I didn't argue.

I prepared the room the way he asked and after a few minutes he emerged from the bathroom.  He was completely naked!  He ran at me and literally pushed onto his bed.  He fell on top of me, all of his weight -- and his erection -- pressing down on me.

"This is the way things are going to be from now on, Lydia," he stated, calling me by my mother's name.  "Now spread your legs."

After School Sissy -- Part 1

Everything changed after my mother died.

When we got back home after her funeral, my stepfather told me to make him dinner. He said that now that my mother was gone, that I would have to start "taking her place." I made his dinner without arguing, because he is a very big man with a bad temper.

Over the next few days, I would learn that "taking her place" also meant that I had to do all the chores around the house, including all the cleaning, doing his laundry, mending his clothes, cooking his meals, everything.   I did my best to do these things well, but my stepfather was never satisfied. He beat me several times when he was displeased because I hadn't ironed his shirts as well as my mother had or because his coffee didn't taste the way it had when my mother had made it.

One night while he was beating me with his belt for over-cooking the roast, he said, "Maybe you would be able to do your chores more like your mother if tried dressing like her." So the next day when I got home from school, I went into my mother's closet to look for something to wear.  I pulled out a pink dress that I knew had been one of her favorites.  I took off the jeans and tee shirt I had worn to school and slipped the pink dress on over my head.  I struggled with the zipper in back, but was able to pull it up most of the way.  It felt strange wearning my mother's dress, but I really didn't have time to think about it because my stepfather told me that he wanted to whole house vacuumed before he got home.  So I just got busy with my chores. 

When my stepfather got home and saw me wearing mother's dress, he smiled. That evening he was much nicer to me and didn't complain about any problems with how I performed my chores.  As I finished putting away the dishes, my stepfather said that tomorrow he wanted to see me wearing mother's stockings and high heels with my dress. And he wanted me to wear some make-up too. I had no idea how any of this was supposed to help me do chores better -- but I wasn't going to argue, especially since he was being so much nicer to me.

But I did tell him that I had no idea how to put on make-up.  I was afraid if I tried to do myself and I looked bad, he would just get angry with me again.

"Don't worry," he said.  "I'll have someone come over here to work with you after school to show you how to do it."

Helpless Sissy Love Doll

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Sissy Goes Outside Part 3

It's been two months since my sister and her friends set me up to be caught by the Tasker brothers when I walked in front of their house wearing my sister's clothes.  My life has been a total nightmare ever since.  The boys make me come over to their house every day after school.  My sister thinks it's funny and that I'm getting what I deserve for being such a Sissy.


On that first day, after the boys had dragged me inside, they told me that I was now their "little Sissy sex toy."  They said that I had to do everything they told me to do or they would kill me!  Well if you had ever met either of the Tasker brothers, you would believe their threats.  And for the next two hours they took turns raping me.  One would hold me down while the other would have sex with me.  It felt like they pumped a gallon of cum in my bottom.  When they used my mouth, they forced me to swallow their hot, sticky cum.   It was horrible -- but there was nothing I could do about it. They were both so much bigger and stronger than me.  I was trapped and completely helpless.  I was crying the whole time, begging them to stop -- but they ignored me and just kept fucking me, over and over, like a pair of wild animals.


After a couple of hours they started to get tired and bored, so they told me to get out.  But first they told that I had to come back every afternoon.  They told me to be at their front door at 4:00 sharp and to "look real sexy."  And they also told me that next time I better not be such a "Sissy crybaby."

So everyday, as soon as I get home from school, my sister helps me with my make-up and clothes before driving me over to the Taskers' house.  She teases me saying things like, "What a lucky Sissy you are to have two boyfriends," and "You are such a Sissy slut!"  She's given me some of her old dresses and underwear -- and her friends have contributed some old clothes to my new wardrobe as well.  I try very hard to look pretty, because I'm worried that the boys will get angry with me if I don't look nice.  My hair is now a bit longer and I think I am getting better at looking like a real girl.

Now when I go to the Taskers' house, I arrive by 4:00, as instructed.  I stand on the porch until one of them, usually Ben, the younger one, opens the door.  If the weather is nice, Ben makes me pose for photos before he lets me inside.  This is a picture that Ben took of me today on the same sidewalk where they first caught me two months ago.   I'm wearing a dress that my sister bought at Goodwill for me and a pair of shoes from one of her friends.


Recently, they've started making me do chores around their house before they start having sex with me.  Today I had to wash all dishes in the sink and do some laundry before the brothers decided it was "play time" and started taking off their pants.  I've become their sex slave and maid, all in one!

A Sissy's Passage to India

Sissy Kismet was one of my bus depot runaway finds. He was young, small, alone and desperate. Just perfect for me!

I had an outstanding order from an Indian textile billionaire.  He had given me very precise specifications but I just couldn't find the right raw materials to make the Sissy wife he wanted. He also had a practically unlimited budget, so I was motivated not to disappoint this client.

Just as I was about to give up hope, I stumbled upon this perfect little sissy-to-be. It was easy to lure this frightened, exhausted little runaway back to my home where I could perform my feminization magic.

Within 24 hours, my latest acquisition was begging to be returned to his wretched life as a hungry bus depot runaway -- anything to escape the horror of his forced transformation.  I had to do a rush job.  My Indian client wanted to take delivery in just seven months so I pulled out all the stops.  Little Sissy Kismet's life became a non-stop, 24/7 exercise in extreme feminization.   I used massive dosages of hormones, some quick surgeries combined with brutal behavior modification training to perform the rapid transformation.

In preparation for my client taking delivery of his new young Sissy bride, he had purchased a traditional Indian wedding outfit -- complete with a long silk sari, veil and jewelry -- and had it shipped to me.  On the day my client came to inspect his new possession for the first time, I dressed the precious little Sissy in his wedding dress and jewels and carefully did his make-up to make him look both exotic and innocent.  I was delighted with how he looked.

Poor Sissy Kismet was in such a panic waiting for his new Husband and Master to arrive.  The pathetic little thing was literally quivering with terror.  But things really started to be fun when my client arrived.

My rich Indian client was repulsive.  He was a fat, disgusting brute.  He even smelled bad.  But when he first laid eyes on Sissy Kismet, I could tell that I had exceeded his expectations.  As he walked around his Sissy bride, inspecting his purchase, his excitement mounted.  The Sissy just stood there, motionless as he had been trained, his eyes looking down to the floor.  The disgusting businessman gave his Sissy's ass a firm squeeze.  He reached one massive hand down the front of his Sissy's sari, roughly feeling the Sissy's tiny but growing breasts.  Sissy let our an adorable little yelp when that happened.

The businessman started to unbuckle his belt and unzip his pants, but I stopped him.  "Oh no!  You can't do that yet.  Not until you've paid!"

"Fine." the businessman grumbled.  "I'm late for a meeting anyway."  He re-zipped his pants and picked up the briefcase he had brought with him.  "Here," he said as he handed me the case.  I opened it.  Inside were stacks of hundred dollar bills.  My full payment in cash.

"Deliver him to my private plane in the morning," he said to me.  And to his lovely little Sissy he said, "And when we arrive in India, you and I will be married.  Won't that be wonderful!  You will be my little Sissy wife and slave for the rest of your life."

Sissy Goes Outside Part 2

I wasn't happy at all with the outfit the girls had picked out for me.  They had dressed me in a black bra, a while mini skirt and a very sheer blouse.  I felt half naked in the short skirt and sleeveless top.  I had also complained because I didn't like how everybody would be able to see my bra right through the blouse, but my sister just told me to shut up. 


The girls drove me to the corner of Church and Walnut.  I was so scared that I started to feel dizzy.  My sister told me not to cry or I would mess up my mascara.  When we arrived, the girls pushed me out of the car and handed me a black purse to carry.  They said they would be waiting for me at Parker Street, about a ten minute walk away.  The girls were laughing as they drove off.

I started my walk.  At first my heart was racing.  I had never been outside dressed like this.  The air felt cold on my bare arms and legs.  I was very aware how sheer my blouse was and that made me very nervous.  But after a couple of minutes I started to relax a bit.  There were no other people out on the sidewalk and the few cars that drove by didn't seem to notice me at all.  I was even beginning to enjoy the feeling of being out dressed like a girl.  I slowed my pace a bit, stood up a little taller and even tried to put a little wiggle into my hips as I walked.

Before long I was only about two blocks away from Parker Street, my destination.  I could see the girls in their car waiting at the corner.  They started shouting to me things like "You're almost here!"  and "Just a few more feet to go!"  I smiled.  I had survived my ordeal and my secret would be safe!

But it was at that moment that I realized that I was passing in front of the Tasker brothers' house.  Ben Tasker was a senior at my high school and was on the football team.  His older brother Dick worked at the gas station.  Both of them were big, mean and stupid.  And in the blink of an eye, Ben and Dick were standing on the sidewalk in front of me, blocking my way.  "Well look at this," said Dick.  "Looks like we caught outselves a Sissy walking around our neighborhood."

"Yup," replied Ben.  "At first, I didn't believe it when the girls called us.  But here he is, on our sidewalk, just like the girls said he would."


It had all been a big set up.  I had fallen right into my sister's trap.  At that moment I heard the girls drive off, honking their horn and laughing as they left me there with these two thugs.


"Well, let's get you inside, little Sissy," said Dick as he roughly grabbed my arm and started to drag me towards the front door.  I tried to squirm free, but then Dick slapped me hard and warned me to be "a good little Sissy, or else!"  I was too terrified to resist further.


"This is going to be fun!" shouted Ben.


"I get to go first," said Dick as he shut the door behind us.

Sissy Goes Outside Part 1

I liked dressing up in my older sister's clothes and I did it whenever I was home alone.    First, I would put on one of her bras and a pair of her panties.  Next I would go to the bathroom and do my make-up and fluff up my longish hair.  Then I would go through her closet, trying on her dresses, skirts, blouses and shoes.  I even dressed up in her nightgowns and bathing suits.  I would pose in front of her full length mirror, admiring my feminine reflection.

That's exactly what I was doing when disaster struck.

I was all dolled up in my sister's make-up, underwear and a party dress.  The dress was my sister's favorite.  It had a feminine, white ruffled top, a black skirt and a wide belt that gave me a sexy shape.  I was also wearing her sexy new peep-toed pumps with really high heels.  I felt so girlish and sexy.  I was posing and admiring my reflection in her big mirror when I heard a girl's voice scream, "Oh My God!"   I spun around and saw my sister and two of her friends standing behind me. My sister's friends started laughing uncontrollably.  My sister shouted, "What the fuck are you doing in my clothes?!?"

I was too shocked to speak so one of her friends answered for me. "Your brother is a total sissy faggot!"

My sister glared at me for a minute and then said, "Don't move."  She went downstairs followed by her friends. I was so afraid and confused and ashamed that I that just stood there as she ordered.

A few minutes later the three of them returned.  "Well Sissy," she said, "I'll make you a deal.  I won't tell Mom and Dad about this -- but you have to do something for me."

"Sure," I said eagerly.  I would do anything to keep my parents from learning about this.  "What do I have to do?"

"It will be easy," my sister replied.  "All you have to do is to walk down Walnut Avenue, from Church Street to Parker Street." 

"You want me to go outside?  Dressed like this?" I exclaimed.  I had never even thought about going outside before.

"No!  Not in my favorite party dress.  We'll pick out something cute and appropriate for you to wear.  Now don't be such a Sissy," my sister said while her friends giggled.  "Walnut is a quiet street.  Now get into the bathroom so we can fix you up."

I really had no choice so I complied.  And my sister was right -- Walnut was a quiet street.  I should be able to do this.

Well, the girls teased me mercilessly as they made me  strip down to my sister's bra and panties.  They  went to work on my hair and make-up and made me look really pretty -- much better than I had ever done myself.  Then they picked an outfit for me to wear.  The girls helped me dress and then ordered me into the car.  Now I stated to get nervous and I said that I had changed my mind.

"Too late, Sissy!" my sister snarled.  "Shut up and get in the car."

I started to cry as the girls shoved me into the back seat of the car.

Cornered Sissy

It was time for the evening fun to begin. After enjoying the dinner that his Sissy had prepared, Master Night ordered his Sissy to stand beside him.

"Strip," he ordered.  Sissy Dawn knew better than to resist his Master's instructions. But he hesitated for just a moment thinking about the "game" his Master would want to play as soon as his soft white skin was exposed.

Master Night would tolerate no such hesitation. He instantly slapped Sissy Dawn's bottom with all his strength, nearly knocking his feminized boy toy to the ground. "I said strip. NOW!"

"Yes, Master, Sir," the Sissy quickly answered, practically ripping his pretty little dress from his body. "Sorry, Sir.  I apologize for being so slow."

Sissy Dawn's frilly sundress now lay on the floor. The Sissy stood before his Master wearing only his sexy bra and panties. His enormous breasts were practically spilling from his strapless bra.  Master admired the Sissy that had been sculpted exactly to his specifications.  He enjoyed knowing how humiliating it was for his ultra feminized Sissy to be on display wearing nothing but his beautiful, lacy lingerie.

"That's more like it," Master Night said, as his hand began the rub his Sissy's pantied bottom.  "Do you like it when I do this?" Master Night asked.

"Oh yes, Master," the Sissy replied breathlessly, just as he had been taught. "I love it when you fondle me."

"That's because your such a slut," Master answered with a sneer. "You disgust me. Did you know that, Sissy?"

"Yes sir," Sissy Dawn replied. "I do not deserve the privilege of being owned by you."

Master smiled at his Sissy's total submission. Leering at his nearly naked Sissy, Master Night said, "Let's play a game of hide-and-seek." Sissy Dawn's heart started racing with fear. "Ready, set, GO!"  Master shouted.

And with that, Sissy Dawn started racing through the mansion, his big boobs bouncing as he tried to run in his high heeled sandals.

"Ready or not, here I come!" Master shouted, just a few seconds later when the Sissy had only reached the foyer. Sissy Dawn sprinted as fast as his sissified body would let him. He ran through the formal dining room and through butler's pantry. He made it to the study and was about to run up the back staircase when Master caught up with him.

"Sissy, I'm disappointed. That was too easy. I don't think you were even trying," Master said.  "Oh well, I won again!"  And with that, Master pulled the taser from his pocket.

"Please Master, no! Not the taser!" Sissy Dawn pleaded as he backed into a corner of the room, desperate to get even a few inches away from his insane Master and his taser.

"Now Sissy, you know the rules," Master replied sternly.  "If I can find you in less than ten minutes, I get to give you a stingie."

"Please Master!  NO!  It's not fair..."

Master had heard enough. He jammed the taser into his Sissy's crotch and gave his Sissy a long, nasty shock.  Sissy Dawn screamed and collapsed on the floor. And because he was now angry with his Sissy, Master gave another shock to each of Sissy Dawn's giant tits.

Sissy Dawn writhed on the floor from pain. Master took advantage of this to kick his nearly naked Sissy.  Sissy Dawn sobbed uncontrollably as he lay helplessly on the floor.

"The rules are the rules, Sissy. Dont you forget that!"  Master said as he unzipped his pants.  "Now let's have some more fun..."