A Boyfriend for my Sissy Husband -- part 4

Martin had ordered some champagne from room service which was a very good idea because even though Danielle was excited by everything that was happening to him, he was also very frightened.  The champagne helped to settle his nerves.

"Martin," Danielle said softly, "I need you to know that I've never done this before."

"That's OK," Martin replied coolly, "I've done it lots."

Danielle wasn't exactly sure how this was going to work. If he took off all his clothes, he wouldn't look like a girl anymore and that would spoil the effect for Danielle -- and maybe for Martin too. So while Martin was in the bathroom, Danielle pulled out a sexy nightgown that he managed to stuff in his purse before leaving.  He slipped his nightgown on over his well-padded bra and panties. Danielle freshened his lipstick, put on a bit more perfume and checked himself out in the mirror.  He was very satisfied that he looked pretty and sexy in his nightgown. And with his bra and pads in place, he had all the right curves.  His fantasy was intact; he was a beautiful woman about to have sex with a handsome man.  He slipped on the hotel robe and waited.

Martin emerged from the bathroom looking very sexy. He was also wearing a hotel robe. They made out for a few heavenly minutes. Then Danielle dropped his robe to the floor, revealing his sexy nightgown. Martin looked admiringly at Danielle and gave him a little wolf whistle. "Let's get under the covers," he said.  And so they did. And then the action began.

Martin took control and directed Danielle every step of the way.  And Danielle did everything -- everything -- Martin told him to do.  It started with Danielle stroking and massaging Martin's cock, which made it get stiff.  Danielle was amazed by how big Martin's cock was! It seemed to keep growing and growing the more Danielle played with it. It was at least ten times as big as Danielle's tiny penis.

Then Danielle was instructed to kiss and suck on Martin's cock.  Martin started pumping slowly back and forth in Danielle's mouth. Danielle struggled to fit much of Martin's giant dick in his mouth but he tried his best.  Then Martin's rocking started to get faster and stronger.  After a few minutes, Martin was forcing powerful, deep thrusts into Danielle's mouth, forcefully holding Danielle's head in place so his cock was snaking into Danielle's virgin throat.  And that is when Martin started cumming for the first time.  It seemed to Danielle that a gallon of hot semen was flooding into his mouth.  "Swallow it!  Swallow, bitch!" Martin growled.  Danielle never heard him talk like that but figured it was what real men say when they're excited.

Danielle's ass was next and Martin was ready to do again after just a few minutes rest.  Martin smeared lube on his dick and on Danielle's ass. He positioned Danielle on all fours and then he went to town.  For Danielle, it was very painful at first, having a giant cock rammed up his butt for the very first time. But after a few minutes it started to feel good and Danielle enjoyed the feeling of giving his man such pleasure. Just like before the thrusting start slowly but picked up speed and power as Martin's excitement built. He fucked Danielle hard.  With one arm wrapped around Danielle's waist, he used his free arm to spank Danielle's ass -- hard -- in time with his thrusts. "Say you love me, bitch!  Say it!  Say it now and say it loud!" he yelled at Danielle. Danielle didn't like being called "bitch" but he did as he was told.  "I love you, Martin.  I love you!" he said as loud as he could. As Martin came inside Danielle's ass, Danielle's little dick exploded too, spilling his cum all over the sheets.

Martin wasn't done.  He had taken three Viagra pills as soon as they had checked in.  He shoved his filthy dick back into Danielle's mouth and Danielle didn't protest. After several minutes of more rough thrusting, Danielle could tell Martin was about ready to cum again. Danielle prepared himself to swallow another flood of semen.  But Martin didn't cum in Danielle's mouth. Instead, Martin pulled out of his mouth just before cumming, shooting wads of hot cum into Danielle's face and hair.

Martin climbed out of bed and let out a little chuckle as he looked at the cum soaked sissy mess lying there. "Here," Martin said, handing Danielle his champagne glass, "have a drink."

 "Are you coming back to bed?" Danielle purred.  "I want to snuggle."

"Sure, I'll be there in just a minute," Martin said.  Danielle pulled the sheets up to his chin and promptly fell asleep.

A Sissy every Weekend -- Part 7. After the Dance

Caroline followed me back to the bedroom.  She sat down on the edge of the bed and gently placed a hand on my shoulder.

"I'm sorry I teased you like that," she said.  "I really do appreciate what you did for me tonight.  And I would like to show you how grateful I am."

I had no idea what she was suggesting.

"Now take off your dress and put on your nightie and I will be back in a minute."  Caroline disappeared into the bathroom.

I forced myself to stop crying and dried my eyes with a tissue.  I stripped off the pretty dress, the stockings and the bra and panties I had worn to the dance and slipped on my pink nightgown.  Caroline emerged from the bathroom wearing only her bra and panties and carrying a bottle of lotion and a small towel.  "Now I want you to just lie back and relax," she said as she sat on the edge of the bed.  She looked so beautiful wearing just her underwear.  I tried not to stare but I couldn't help it.

As I laid back, Caroline lifted the bottom of my nightgown.  She squeezed some lotion onto her palm and began to gently stroke my little penis.  I had never felt anything like this before.  Here was the girl I loved so much, wearing only her bra and panties, giving me a hand-job!  My little penis instantly became erect.  As Caroline stroked me I tried not to think about how much different I must be than her boyfriend Robert.  Robert was big and strong and masculine; I as dainty and feminine, my skin was soft and my cock was tiny.

I couldn't believe this was really happening.

Caroline stopped pumping for a moment.  "Now don't make any noise, Sweetie.  We can't let anyone know what we are doing.  Do you promise to be quiet?"  I quickly nodded in agreement.  Caroline resumed playing with my cock with her soft, lotion-covered hands.

"Does that feel good, Tiffany?" Caroline whispered into my ear as she continued to pump my little penis.  "Ohhhh, yes," was all I managed to reply.

And then I started cumming.  My little cock just exploded, spurting and spurting, over and over.  Caroline smiled down at me while I orgasmed.  "Well," Caroline said.  "It looks like someone really enjoyed that!"  She kissed me on the forehead and went into the bathroom to wash her hands.

When Caroline returned she again at on the edge of my bed.  "You really were wonderful to go to the dance with me tonight."  She stroked the my cheek with her soft fingers.  "Now get some sleep."

She moved to her bed. "Oh, by the way.  Robert's parents have invited you, me and Mark out for brunch tomorrow morning.  I already said that we are going. It will be fun and I know Mark will enjoy seeing you again.  And if it all goes well, who knows, maybe I'll be able to show you how grateful I am again."  With that Caroline turned off the light and climbed under her covers.

Caroline was completely manipulating me.  She knew she had me under her spell and I was powerless to resist.  Tomorrow I would be out again -- with a boy who thought I was really a girl.

I struggled to fall asleep, but when I did, I had dreams about Caroline -- and Mark.

A Sissy Every Weekend. Part 1. Going to Aunt Jenny's House

This is a picture of me taken last Saturday when I visited my aunt and my cousins. And while you may think that I am a girl, I am not.  I am a boy.  But this is what I look like every weekend. Let me explain.

During the week, Monday through Friday, I'm pretty much like the other boys at school.  Of course my hair is a little longer and I'm very skinny.  Also I don't like playing sports and don't really have any friends.  But other than that, I'm just another boy at school.  

But all that changes as soon as I come home from school on Friday afternoon. "Hurry up, Sweetie!"  mother will call out as soon as I step through the door. "Time for you to change so we can get to Aunt Jenny's house."  She has already packed weekend bags for both of us and she impatiently waits for me to get dressed. It has been the same every Friday afternoon since I can remember.

I know mother was disappointed -- deeply depressed, actually -- when I was born. She is very close to her sister -- my aunt -- who has three daughters; the twins are four years older than me and Caroline who is about one year older than me.   After Caroline was born my mother had hoped desparately for a little girl of her own so that she could join her sister in endless mother-daughter activities.  But since I was born a boy, that dream was spoiled.  Or it would have been if not for my mother's determination.  Mother simply decided that I would have to be a girl when we got together with my aunt and cousins.  And we all get together -- all six of us -- every weekend. 


And if you wondering, there are no men around at all.  Aunt Jenny is divorced and mother was never married.  So I'm the only one in both our families who isn't a girl. At least not really a girl.

Sometimes I wish I didn't have to pretend to be girl every weekend. But I guess I don't really mind too much. It makes my mother very happy and I love my aunt and my cousins very much. But still sometimes I wish mother would let me be a normal boy...


So my weekends begin on Friday afternoons as I change out of my boy clothes and put on my girl clothes.  Even though my cousins and my aunt all know that I'm a boy, it was decided that I should already be dressed as a girl when I arrive at Aunt Jenny's house. That way it is less confusing for my cousins, I guess. 









I start by slipping on a pair of panties and a padded bra that makes me look like I have little boobs. Wearing just my undies, I brush my hair to look prettier and put on some mascara, a little blush and some lip gloss. 

Today, mother has laid out a white lacey top and a peach colored skirt.  The skirt is very short and I don't really like that, but mother says it makes me look very pretty. She also told me to take my blue and white purse and to wear my blue shoes with the 2 inch heel and the ankle strap. 

Mother fastened a little necklace around my neck. Then she snapped a few photos of me for her scrapbook like she does every Friday once I am dressed.  


Mother tells me that it is time to go so I get into the car and we start the 45 minute drive to where my Aunt Jenny and my cousins live.

Uncle Jim Gets a Sissy

After my parents died in a car accident, I was sent to live with my Uncle Jim.  I had never really liked Uncle Jim.  I had always thought that he was sort of rough and maybe a little strange. I was about to discover how right I was.

Uncle Jim lived alone in a big, old farmhouse far out in the country.  His wife, Darla, had walked out on him many years ago.

No sooner had I brought my suitcase into the house the Uncle Jim announced, "You won't be needing your old clothes.  I got plenty of better clothes for you to wear.  You see, when Darla ran out on me, she left all her old things.  And so now you can take Darla's place.  So why don't you go upstairs and put on one of Darla's pretty dresses while I go out back and burn your old clothes."

I began to protest but Uncle Jim started beating me.  Hard.  I was no match for him; I was small and weak and he was huge and strong.  It didn't take long for him to wrestle my suitcase away from me and to drag me up the stairs to Darla's old closet. He picked out a dress and threw it on the bed.  "Now get changed like I told you to!" he shouted.  "There's underwear and make-up in those drawers and there are pretty shoes in the closet.  Now hurry up, get dressed and get your ass downstairs."  He hit me again before he slammed the door behind him and stomped down the stairs.

I was paralyzed.  I started crying as I sat on the bed, looking at the flowery dress that was lying there. Then I smelled smoke.  I looked out the window and true to his threat, Uncle Jim was burning my clothes in the back yard.  I knew I was in big trouble and that I had better start cooperating or something really bad would happen to me.  I put on one of Darla's bras, a pair of her panties, the dress and some shoes.  I put on some red, red lipstick and some rouge on my cheeks.  I took a deep breath and headed down the stairs to where Uncle Jim would be waiting.

That was nearly a year ago.  I have been living and dressing as Darla all day, everyday, since I arrived.  My hair has grown longer and I am now better at doing my make-up and walking in high heels. Uncle Jim calls me Darla and expects me to do everything a good housewife does. I cook and serve three meals a day for him. I scrub the floors and wash the windows. I vacuum and I dust. I do Uncle Jim's laundry. My chores are endless. I hate my life. As I do my chores, hour after hour, day after day, all I can think about is how wonderful and free my life used to be, when I was a normal boy. But that life is behind me now. I am the Sissy housewife/slave of a demented monster.

Uncle Jim gets very mad at me if he catches me daydreaming or not doing my chores vigorously enough.  And he gets furious if he thinks I don't look pretty enough or if I don't sound and walk and laugh enough like Darla did. And when I disappoint him he throws me over his knee and spanks me brutally.

And after I have cleaned the the house from top to bottom and after I have put away the dinner dishes, I have to put on one of Darla's nightgowns and take care of my "husband's" sexual needs.   No matter how awful my household chores are, nothing is as awful as having Uncle Jim's giant naked body on top of me, kissing me and feeling me up all over. But worst of all is when I have to do the things that he says Darla refused to do. I have to put Uncle Jim's cock in my mouth until he gets ready to cum. Sometimes he likes to cum in my mouth and make me swallow it.  But mostly, he likes to pull It out just before he cums and shoots it all over my face. After I clean us both up, Uncle Jim usually climbs on top of me again and falls asleep. That's when I usually start crying until I fall asleep, getting a little rest until my life as a sissy housewife/slave starts again in the morning.  

A Sissy and his Mother Have a Weekend Adventure -- Part 1

My son, Jamie, and I share a big secret.  Jamie is Sissy.  And while he tries his best to act like a boy at school, at home he is my Sissy daughter, Janey.  Over the years, Janey has really blossomed into a delightful young "lady" and I love the special times I get to spend with the daughter I never had.

Last weekend, we had the most wonderful adventure. After Jamie came home from school on Friday afternoon, we drove into the city, which is only a couple of hours away. We checked into our hotel and that's when the real fun began. Jamie stripped off his boy clothes, slipped on a fluffy bathrobe and started becoming my daughter Janey. Over the next hour and a half, Janey and I got ourselves all dolled up for a night in the city.

We finished doing our hair and makeup. I helped Janey zip up the new little black dress that I had bought for him. I let him borrow one of my necklaces and a fun oversized purse. Janey put on his favorite strappy platform sandals and he was ready.  Doesn't he look lovely!?!

We then went to the ballet which we both loved! Then we enjoyed a late dinner at a fancy French restaurant. It was marvelous.  The waiters fawned over my pretty daughter.  One even jokingly begged Janey for a date!  Janey was a good sport and giggled and blushed like a young lady would. 

Exhausted, we went back to the hotel where we slipped into our nighties and went to bed.

On Saturday morning, Janey decided that he wanted to wear his red dress.  It is very simple and yet so elegant.  And Janey knows he looks fabulous in it!  

We had breakfast at the hotel and then went to the art museum which had a wonderful exhibit on ballgowns from the 18th and 19th centuries.  Janey and I both enjoyed this very much.  We spent so much time at this one exhibit that we barely saw anything else in the museum. 

After we were done at the museum, we walked over to the Ritz Hotel where they serve the most delightful afternoon tea. Janey and enjoyed all the little sandwiches and sweets that were served.  Elegantly dressed ladies sat at all the other tables; some tables apeared to have mothers and daughters having tea together -- just like Janey and me!  I felt so fortunate to be able to share this experience with my special Janey.

After tea, we spent the rest of the afternoon shopping. At the lingerie shop I bought Janey some new bras and panties and stockings.  We then found some shoes for Janey at the big department store -- a pair of black patent leather slingbacks with a three inch heel and some cute sandals for the summer. Then we visited a couple of the designer boutiques and I had Janey try on literally dozens of dresses!  In the end we only bought one dress for Janey -- oh, but what a dress. 











We returned back to our hotel exhausted carrying all of our new purchases.  Since we were tired, we decided that we would have dinner downstairs at our hotel.  As we started to get ready for dinner, Janey asked me, "Mother, do you think I can wear my new dress tonight -- the one you bought me this afternoon?"

"Of course, sweety,"  I replied.  "I am sure that your new dress will be just perfect for tonight.  The hotel's restaurant is rather fancy and I am sure people will be dressed very nicely.  So yes, please wear your new dress."

We finished doing our make-up and fixing our hair.  Janey slipped on his new dress and modeled it for me.  "Oh, Janey," I sighed.  "You look...amazing."  A tear started to well up in my eye as I gazed at my beautiful, elegant son.

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.

Custom Ordered Sissy

For the Sissies that I transform for my own fun and amusement, I typically go for a slim, slinky look.  You know, teeny little waist, skinny arms, long lean legs...Mmmmm.  And with this look, I usually go for feminine, lady-like bosom, a B-cup or maybe a C-cup. 

But when I get a custom order for a Sissy, the buyers almost always seem to want really, really big boobs.  Well, the customer is always right -- and I don't disappoint my customers!

Sissy Angelique came to me voluntarily three years ago.  He wanted to be transformed into a pretty girl and had dreams of opening a beauty salon.  Well, half of Sissy Angelique's dreams came true; he is indeed very, very pretty now.  As for returning home to open a beauty salon, well, that was never going to happen. 

I had an order for a Sissy with really big tits.  And I saw that Sissy Angelique had the right physique to look awesome with an enormous rack.  Of course, he totally freaked out when I told him what I was going to do to him.  But by then it was far too late for him to regain any control of his fate.

My client was delighted when I presented Sissy Angelique -- and those huge boobs -- to him.

And now, everywhere Sissy Angelique goes, he attracts stares and lewd comments from men and disgusted looks and derisive comments from women.  And his Master delights in showing off his Sissy's majestic boobs in public, allowing his Sissy to wear only the skimpiest, most revealing tops.  Sissy Angelique begs his Master to allow im to wear a bra and to cover up his massive tits.  But why would his Master agree to that?

Sissy Prepares to "Entertain"

Sissy Amanda's cell phone buzzed.  It was a text message from his wife.  "Leaving now.  Home in 1 hour.  Be ready to entertain."

"Home in just one hour!?!" Sissy Amanda thought with alarm.  He stopped scrubbing the kitchen floor and raced to his little bedroom in the basement.  He stripped off his maid's uniform, sat down at his vanity and got busy making himself look beautiful.  His wife and her lover would be home soon from their romantic weekend in the country and Sissy Amanda had been instructed to always look his best when they returned.  And from the text it was clear that he needed to be prepared to sexually "entertain" them as soon as they arrived.

Sissy Amanda finished doing his make-up and took a moment to look at his reflection in the mirror before putting on his dress.  He looked at his delicately arched eye-brows, at his sexy, smokey eye shadow, at the pink lipstick that coated his soft, full lips.  He burst into tears thinking about what he had become.......

Mother's Pretty Little Sissy Daughter -- Part 1

The day I caught my son crossdressing was the happiest day of my life.

I had come home early from work and found my son, Jesse, sitting at my vanity, putting on make-up.  He was wearing one of my cocktail dresses -- and my stockings, my high heeled sandals and, it appeared, my lingerie.  He hadn't heard me come in, so I just stood silently in the doorway watching him put on mascara, blush and lipstick.  He was completely mesmerized by his own ladylike reflection, completely entranced by the girl in the mirror. He did a very good job with his make-up; clearly he had done this many times before.

Of course, Jesse was very upset and embarrassed when I announced my presence after enjoying the show for several minutes.  He started spewing all sorts of pathetic explanations and denials.  I tried to calm him by saying that it was OK.  He settled down enough that he even let me help him finish doing his make-up.   I encouraged him to stay dressed while we ate dinner.  I treated him like a girl throughout the evening and he seemed to enjoy the experience.

So why was that the happiest day of my life?  Because I had always wanted a a daughter -- and now I had one!

That was two months ago.  Ever since that fateful afternoon, I have been working day and night to convince my little Jesse that he is too pretty to be a boy and that he was always meant to be a girl.  When he is dressed as a boy, I treat him mostly with indifference and I react harshly to any little mistake he makes.  But when he is dressed as a girl, I shower him with the affection he craves and I lavishly praise his every girlish accomplishment.  In this way I have lured him -- trapped him -- into more fully embracing his feminine side, using my love and affection as bait. 

He is now in the habit of changing out of his boy clothes as soon as he gets home from school.  My son Jesse becomes my daughter Jessica for the evening.  And all through the weekends.  He has become proficient doing his own make-up.  And with my coaching, his mannerisms and his voice have become delightfully feminine as well.  He now has a closet full of his very own dresses and his drawers are overflowing with his own bras and panties and stockings.

Recently, I have started taking my daughter Jessica out of the house at night.  We've started going to restaurants and movies together.  Tonight we are going to the ballet!   I even bought him a pretty new dress to wear.  He's very excited.  Here's a photo of Jessica doing his make-up for our big evening out.  Doesn't he look sweet?

I can't stand the idea of not having my daughter Jessica with me all the time.  I have all sorts of ideas for how we can spend more mother/daughter time together.  I'm hoping that by spending more time as Jessica that Jesse will more fully embrace life as my beautiful, sweet little sissy daughter.    

I think he will learn to love his new life as Jessica.  Don't you?

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."

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..."

Sissy's Sexy New Lingerie

 "Oh Sissy Belinda!  Come here!" my Wife shouted from her bedroom, ringing a bell that could be heard throughout the house.  I had been dreading this moment all night. 

Four hours ago, before going out on a date with her new boyfriend, my Wife handed me a box from a fancy lingerie shop downtown.  "There is a very pretty new bra and panty set in the box.  I want you to be wearing this and looking your sexiest when I get home.  And I want you wearing this pink bow in your hair.  And this lacey glove.  Do you understand?"

"Yes, Ma'am," I meekly replied.  And while my Wife was out on her date, I dressed in the outfit as ordered.  I carefully tucked my pathetic little cockette away to ensure there would be no unsightly bulges.  I worked very hard to make my hair and make-up look sexy too.

My wife had returned home about an hour ago and was entertaining her new lover in the Master bedroom.  I had been waiting in silence in the laundry room, which was now also my bedroom.   And now I had been summoned.

I raced up the stairs to my Wife's master bedroom because my Wife hates to be kept waiting.  There I found my Wife and her lover sitting in bed naked, breathless from having just made love.

"You see, Charles, you didn't believe me.  This is my Sissy husband.  I call him Belinda now," my Wife explained to her muscular and handsome lover.

"No way!" he exclaimed in disbelief.  "That hot chick was your husband?"

"Well, unfortunately, technically he still is my husband, but you neededn't worry about that."  Then to me she said, "Well don't just stand there, Sissy Belinda.  Show us what you got.   Give us some sexy poses and show us what a pretty and pathetic little Sissy you've become.  I want to take some more photos of you."

As instructed, I struck several provocative poses, while my wife snapped away with her camera.  I could see the sheets cover Charles' lap begin to stir as I did my thing.  Obviously he was enjoying my performance and getting excited.

"And Charles, Sissy Belinda doesn't just look and act like a girl.   Oh no, he also sucks cock like a girl.  Isn't that true Sissy?"

"Yes Ma'am," I replied shamefully.  This was not the first time that my Wife had brought a lover home and forced me to "entertain" him.

"Well then, don't just stand there. Get over here and wrap your lips around this," she commanded as she threw back the sheets.  I gasped with when I saw her lover's monstrous cock.  My wife roared wife laughter seeing the shock on my face.  "Get busy Sissy!"

My Curvy Sissy

There is nothing I enjoy more than a slender, waif-like Sissy.  Their skinny little arms so pretty and weak.  Their slender little bodies so defenseless...

But not every Sissy can be carved into lithe little ballerina.

When Sissy Pamela came into my clutches, he was a bit older and a bit larger than the Sissies I usually work with.  But I thought he had potential and so I went to work on him.  Sissy Pamela was brought to me by his wife.  He thought that after he was transformed, that he would return to his wife for a lifetime of lesbian bliss.  Of course that was never going to happen.  His wife was tired of her Sissy husband and had already taken a new lover -- a real man -- and so Sissy Pamela was all mine, no strings attached.

And I was delighted with the results!  Sissy Pamela is a deliciously curvy Sissy.  It cost a fortune in plastic surgery bills to get the look exactly right.  His soft white flesh contrasting so prettily with the lingerie I dress him him.  His big soft boobs practically spilling from his bras.  His pretty round ass jiggling ever so slightly when he walks around in his high heels.  Delicious!

After nine months of training and surgery, his transformation was complete.  I told him that his wife had come to pick him up and take him home.  He was so excited!  I squeezed Sissy Pamela into the very sexy outfit you see at the right.  I had it custom made for him.  It's not comfortable but he does look gorgeous in it!  His hair and make-up were done just perfectly.  And then I paraded him into the lobby area where his wife was waiting -- sitting on her handsome lover's lap!  At first, poor Sissy Pamela was too confused to be completely humiliated.  It took a lot of explaining to convince him that he wasn't ever going home, that his wife had left him, that she now had a real man for a lover, and that everyone was now laughing at him.  Tears were flooding down Sissy Pamela's face when he finally realized that all of his dreams -- and his freedom -- were gone forever.

But here's the best part.  Who do you think would be most interested in a soft, curvy, fleshy, jiggly Sissy?  Big black men, of course!  Sissy Pamela has been an excellent investment for me because I can whore him out morning, noon and night to a long list big black bulls who can't get enough of my voluptuous creation.  My best clients are a group of five Offensive Linemen for the local NFL team.  They "visit" Sissy Pamela -- together -- at least twice a week. 

As a captive sex toy for powerful and demanding black men, poor Sissy Pamela's life is a horrifying nightmare of nearly continuous forced sex and abuse.

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.

Sissy Inspection

Before taking final delivery of his newest Sissy, Mr. James gave it a thorough inspection.  He unbuttoned the Sissy's blouse and squeezed and played with the Sissy's enormous breasts.


"Mmmm, that's nice," Mr. James said, enjoying the weight of the Sissy's boobs in his hands.  "So soft..." 

The Sissy sat there -- obedient, passive and still -- just as he had been trained, while his prospective new owner fondled and groped him.

Mr. James pulled aside the Sissy's lacy bra to expose one of his big pink nipples.   Mr. James put the Sissy's nipple into his mouth and started sucking on it.  The Sissy started moaning with pleasure at this as he had been instructed.

Mr. James smiled at this and said, "Oh my, aren't you a dirty little Sissy whore!"

The Sissy said nothing and stared at the ground, suffering from both the humiliating sting and the undeniable truth of what Mr. James had just said to him.

Sissy Trainer Answers Your Questions #2

Here's a problem that some other Sissy Trainers have asked me about:

"What do you do if you can't get your Sissy to sign the papers authorizing breast implant surgery?  I've been able to force my Sissy to do just about everything but I can't get it to sign the papers the hospital requires.  What can I do?"

Yes -- that can be a problem.

Well, first off, I never have this problem.  I have a little "don't ask, don't tell" arrangement with some excellent plastic surgeons in Mexico.  As long as I provide the cash, they are happy to do whatever I ask to the "patients" I bring them.

But most Sissy Trainers aren't as lucky as I am and need to get their Sissies to agree to the surgery -- very inconvenient if your Sissy is being forcibly femininized against his will.

Here's my advice:  If your Sissy won't agree to breast implants -- FINE!  Let him parade around completely flat chested.  Force him to wear outfits that emphasize his lack of boobs -- no padding, no bra.  If you do this right, before long your Sissy will begin to feel incomplete and self conscious about being flat chested and absolutely beg you for the breasts he's lacking.

And once he signs on the dotted line, be sure to outfit him with some sweet DD's -- that's what he gets for not cooperating in the first place!

A Sissy's Education

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

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

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

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

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

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

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

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

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

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

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