Sissy Attitude Adjustment

Poor Sissy Millie just couldn't seem to accept what was happening to him. 

Physically, Sissy Millie was a huge success -- his forced transformation from occasional crossdresser to chemically and surgically feminized sissy was nearly perfect.  His face was smooth and beautiful, his body was soft and slender.  His hair was long and full.  And his boobs were...well...incredible.  Just look at them!  I can't resist squeezing them and playing with them!

Everything was perfect except for his attitude.

You see, Sissy Millie continued to insist that he was "a man."  He kept shouting that his name was Simon and he would never be another man's full-time, live-in sissy slave.

This was a real problem for me.  Sissy Millie's new owner was scheduled to take possession of his sissy in just three weeks.  But Sissy Millie's attitude -- his entire mental state -- needed a major adjustment.  And quickly!

I've been through this many times before and I have never failed to break a sissy. Sissy Millie is going to wish he had cooperated with his transformation and succumbed to his new life before it came to this.  He is going to endure punishment beyond his wildest imagination.  Once it begins, he is going to start begging me to stop the torture -- begging to be allowed to embrace his new life as a sissy maid and sex slave.  But I am not going to stop until I know that Simon is gone and only Sissy Millie remains. And if that takes three weeks, well that's OK with me. 

Sissy Millie has been tightly corseted, bound and perched on that little stool all night long, a 12 inch dildo vibrating and pulsing wildly in his sissy pussy.  Morning has finally arrived after a long, painful and sleepless night.  He is terrified and exhausted. But his worst fears about what are about to happen to him are nothing -- NOTHING -- compared to what this final stage of his transformation will be like. We will completely break his will and his soul.

I feel no guilt about the suffering Sissy Millie will soon endure.  This is all his own damn fault.

Completing my Husband's Sissy Journey -- Part 2

I enjoy having my husband, Colette, as my own, private lesbian lover and slave during the week.  But when the weekend comes, I'm ready to get out and really have some fun.  You see, I now have a boyfriend.  And so does my husband!  

When I first told Colette that I had taken a new male lover, he was very upset.  I let him cry for a few minutes but then ordered him to stop his blubbering.  Having a lover is what I wanted and Colette would just have to deal with it.  When he wouldn't quit sobbing I slapped him a few times until he stopped.

The very next night I invited Marcus, my lover, over to our house to spend  the evening with Colette and me.  I made Colette dress up and look his best before meeting Marcus. Here's a picture of Colette putting on his bra as we both got dressed for the evening.  Colette served us drinks and hors d'oeuvres that he had prepared.  He looked so pretty!  I know he was upset watching Marcus and me making out on the couch right in front of him.  But Colette behaved himself and worked hard to make me proud.


But that was just the beginning.  What Colette didn't know then was that I wanted Colette to share Marcus with me!  Marcus would become Colette's handsome lover too!



When I explained all this to poor little Colette, I thought he was going to explode!  He cried and cried.  He begged me not to do this.  But I had made up my mind.

So now, every Friday and Saturday night, Marcus takes his two beautiful "girlfriends" out on the town.  We go to bars, restaurants, dancing.  We even go on vacation together.  I bought Colette lots of pretty new clothes so he can look his best when we are out on our date nights with Marcus.  Here's a pretty pink dress that I think looks very nice on him.

At first it was very difficult for Colette to participate in our special "double dates."  But he cooperates because it is what I want.  

Tonight, Marcus is going to take us to dinner at the fanciest French restaurant in town.  We are celebrating our one year anniversary as a couple (plus one!)  And then after dinner we are going to go to the nightclub at the Hilton where we can dance and drink until very late.  I bought Colette a special new dress for tonight and we spent the afternoon at the beauty salon having our hair and make up done for our big night out.  Doesn't he look beautiful!  I made Colette pose for photos when we left the salon.  I think he looks pretty happy in these picture.  I think Colette enjoys being the object of Marcus's attention and desire a lot more than he admits!  What do you think?

I'm sure Marcus will be pleased that our sissy lover looks so pretty tonight.

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.  

Spring Break Sissy

When I told my parents that I was going to Florida for spring break, they were really worried.  They pictured me hanging out at wild, drunken parties and stuff like that.

But actually, my spring break is very different -- but my parents don't need to know that. 

You see, I am spending the entire week as Professor Wilson's sissy!


Here's a photo of me in the hot tub with my Professor and Master.

It all started last fall when I was taking Professor Wilson's Human Sexuality class.  I went to see him during his office hours one afternoon because I needed help understanding an assignment.  He closed the door to his office after I sat down.  Before I could even ask a single question, Professor Wilson asked me, "You're a sissy, aren't you?"

I was shocked and scared by his question.  The truth is that I am a closeted cross-dresser, often having fantasies of submitting myself to be feminized and controled by a dominant man or woman.  But this was my secret.  I had never told anyone this.  How could Professor Wilson possibly know?

"I asked you a question, sissy!" he shouted.  "Don't deny it.  I know what you are.  I can tell.  It's my expertise, after all.  Now I am going to ask you again.  Are you a sissy?"

I lowered my eyes to the floor, and softly answered, "Yes," unable to resist the Professor's command.

"I knew it!" he exclaimed with a self-satisfied smile.  "Well from now on you are going to be MY sissy.  That means you will do whatever I tell you to do.  You will submit to me in all ways.  Do you understand?"

"Yes, Sir," I meekly responded.  Professor Wilson smiled again.

I now visit Professor Wilson at his home every evening and every weekend.   When we are together, he is not nice to me at all.  As I walk in the door, he instructs me on how I should dress for the evening.   I prepare myself as quickly as possible -- make-up, lingerie, a dress, stockings, heels -- the works.  He then proceeds to order me around for the next few hours.  This usually includes cleaning his house, doing his laundry and making his dinner.   If I do anything that displeases him, he throws me over his knee for a harsh spanking.  

When my chores are done and he has finished eating, he has sex with me.  He often orders me to bend over the back of the couch so he can take me from behind.  If there is a big game on TV, he makes me suck on his cock while he watches the game.  Then after he cums and I have cleaned up the mess, he orders me to get out.

My Professor/Master has helped me to understand that, as his sissy, I exist for only one reason -- to serve and please my Master -- and that my feelings have no importance.  I am just an object for him to use for his pleasure.   

Now it is Spring Break and Professor Wilson has arranged for a perfect Master/Sissy vacation.  All year I have growing my hair out and Master has kept me on a strict diet so that I would look extra girlie for our trip.  He rented a beautiful condo that has a view of the Intercoastal Waterway, a big deck and a hot tub.  He packed several pretty outfits for me to wear, lots of sexy lingerie and even two bikinis!

Master has been so nice to me since we arrived at the condo!  Of course I have to do all the chores and follow all of his orders and he has spanked me a few times.  But mostly we are passing our days and night in bed or in the hot tub.  It has been so romantic!  We have been spending hours and hours kissing and having sex.  And after he is done having sex with me, he has been letting me snuggle up against him.  I feel so safe and happy when Master wraps his big strong arms around me. 

Here we are in the tub again.  I am giving him a handjob.  His enormous, hard cock feels so good in my soft, manicured hand.  I am so content and fulfilled serving and pleasing my Master.  

I wish my Sissy Spring Break would never end.

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!

After School Sissy -- Part 2

Stepfather arranged for a lady to come the house to help me look the way he wanted me to.  She was waiting for me at the front door when I got home from school.  We went inside and she had me take off all my clothes.  With her help, I put on a pair of mother's panties and one of her bras.  She gave me a set of breast forms that filled out the cups of mother's bra and she laced me into a tight corset to give me a "prettier shape."    She sat me down at mother's vanity and for the next two hours she gave me a thorough lesson in putting on make-up.   I was taught how to do everything: putting on foundation, plucking my eye brows, putting on fake eye lashes, mascara, eye liner, blush -- everything!.    Here's a photo she took of me while I was practicing putting on lipstick.

When she was satisfied with my make-up, she had me put on a silky flowery dress and a pair of strappy high heels that she picked out from my mother's closet.  And lastly she pinned a long wavy blonde wig that was styled to look like my mother's hair.  When the lady was done with me, I didn't just look like a girl, I sort of looked like my mother!

But she wasn't done yet.  She stayed for another hour, giving me lessons on walking and sitting and even talking like a girl.

By the time the lady left, it was almost 6:00, so I had to hurry to get Stepfather's dinner ready before he got home.  It felt funny being being dressed up like a woman but I was in a rush and I didn't really have time to think about.  It was a little hard to move quickly wearing my mother's high heels.  I also tried to be careful not to spill anything on mother's pretty dress.

When Stepfather came home and saw me with my new look, including my glamourous make-up, my big boobs, and my nipped waist, I could tell he was very happy.  He was very friendly and relaxed during dinner.  After dinner, he invited me into the living room to watch TV with him. He had never done that before!  He insisted that I sit really close to him on the couch.  He even put his arm around me.  That seemed kind of strange, but it sure was better than being beaten with his belt!

That night was two months ago.  Since then, I've been dressing up in mother's clothes and doing my make-up, just as the lady taught me, every day after school.  I do my chores and make Stepfather's dinner.  And even though I don't like dressing up like a lady everyday, Stepfather is very nice to me all the time, so I guess I don't mind too much.

But recently, when we watch TV together after dinner, he's been making me sit on his lap.  He wraps his arms around me and I have to lay my head on his shoulder.  Sometimes he kisses my neck which feels really weird.

  

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."

A Sissy Learns his Lesson

Master pressed his Sissy hard against his muscular chest.  His massive arms wrapped tightly around his Sissy's head.

"There, there," Master said softly.  "It's over.  Now stop crying."  Master had just finished administering a severe spanking to his Sissy -- 50 of his hardest hits against his Sissy's bare bottom.  Master was very angry that Sissy had been two minutes late serving him his breakfast in bed this morning.
Sissy forced himself to stop crying as his Master had commanded, even though his bottom still burned from the brutal beating.  His tear dampened cheek now rested against his Master's chest.  Sissy felt so safe and so protected when Master held him like this.  Sissy relaxed as he inhaled deeply, savoring his Master's rich, masculine scent.  Sissy even managed a little smile as he felt his Master's massive cock stirring, stiffening.

"Have you learned your lesson, Sissy?" Master asked.

"Oh yes, Master.  I have.  I am very sorry that I disappointed you.  It will never happen again.  I promise."

Master smiled seeing his Sissy's complete subservience.  "Good," Master said.  "Now get on your knees and suck my dick."

Sissy Goes Outside Part 5

For the last few weeks, I've been with Dick every possible minute.  We spend hours in his apartment where he lets me suck on his cock and please him in other ways.  I love making him cum!  It makes me feel alive and valuable to know that I'm giving my Man the pleasure he deserves.

And now we go out together at night too, several times a week.  We go to the movies and bars and restaurants.  It is so exciting to be the feminized Sissy possession of a big strong man.  I love spending my afternoons making myself pretty for Master Dick.  And I love spending my nights being kissed and fucked by him.

I am working so hard to make myself more feminine and sexy for Dick.  I've been dieting and lost seven pounds.  And I've started taking my sister's birth control pills.  The pills have already started making my skin softer and prettier and my nipples have become very swollen and sensitive.

Dick is nice to me almost all the time.  But sometimes I disappoint him and he has to punish me.  I understand.  It is important that I learn to be a perfect Sissy and to always please my Master.  Sometimes Master Dick has to spank me if I have failed him in some way.  He seems to like spanking me, especially if we are out in public.  I am very grateful to my Master for helping me to become a better Sissy.

Master Dick had told me that he had "special plans" for tonight. So I stole this elegant outfit and strappy I I wanted to look my best for my big night with Master Dick, so I borrowed and pretty lacy outfit and sexy strappy shoes from my mother's closet. Then I spent most of the afternoon at the beauty salon and had the girls give me "the works". They even gave my hair some pretty highlights.   I feel so beautiful and feminine!  Dick almost fainted when he saw me!

Dick had made reservation at the fancy French restaurant overlooking the river.  It was all so romantic!  And then, as we were waiting for dessert, Dick got down on one knee.  The whole restaurant went silent and everyone was watching us.  Then, Dick pulled a ring from his pocket and said loudly enough for all to hear, "Will you marry me?  Would you be my Sissy Wife?"

"Oh yes!  Yes!" I exclaimed.  "Of course I'll be your Sissy Wife!"

The people in the restaurant clapped, although they seemed a bit confused by what they just saw and heard.

So now I am going to be married to my Master Dick, who I adore and worship.  I will be able to dedicate the rest of my life to pleasing and serving my Master/Husband.  I am so happy!

And it is all because my sister and her friends caught me dressing in her clothes just a few months ago.  What a lucky Sissy I am!

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!

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..."

A Sissy Gets Ready to Go Home

Charlie had been nothing but trouble for his poor Stepmother.  He had gotten involved with drugs and shoplifting and had gotten expelled from high school just too many times.  And around the house he was rude and obnoxious. 

Fed up with this nonsense, Charlie's Stepmother did the right thing and delivered her rotten stepson to me for some...improvements.

It wasn't easy and it wasn't quick.  But in a little more than two years, Charlie was gone forever and in his place was -- TA DA -- Sissy Charleen!  All it took was some hard work -- and some hormones, some surgery, some sleep and food deprivation, and lots and lots of beatings.  Sissy Charleen was now a quivering, submissive and totally obedient feminized girly-boy.

I enjoyed preparing Sissy Charleen on the day his Stepmother was coming to retrieve him.  Starting very early in the morning, I had the girls from the beauty parlor come over to give Sissy Charleen "the works".  First, a total (and I mean total) body waxing -- ouchy!  Then his hair was shampooed and put up in rollers.  While he sat under the hair dryer, the girls did his make-up and gave him a mani-pedi.  His hair was then brushed out and styled, soft curls pinned back with a pretty bow.  Adorable!

Now, up until this point, little Sissy Charleen had no idea why he was being all gussied up.  As I zipped him into the cutest little pink dress, I explained that his Stepmother had come to take him home and that she was waiting right outside.  Well the little Sissy nearly passed out when I said that!  Sissy Charleen was terrified of being under the control of his Stepmother in his new feminized condition.  Sissy Charleen started to cry and begged me not to return him to his Stepmother.  I sternly instructed him to stop crying, lest he spoil his lovely make-up.  I then reminded him that no one cares what a Sissy wants and that he had best work hard to obey and to please his Stepmother-- or there would be trouble. 

I stepped back to look Sissy Charleen over one last time and to admire my work.  His arms and legs looked so delicate and feminine.  His hair and make-up were perfect.  And the dress I had chosen was simply lovely -- so sweet and innocent.  I gave his hair a final fluffing out and made sure his sparkly heart shaped earrings weren't hidden. He stood there, so prim, so feminine, so terrified, as I invited his Stepmother to enter.  The poor little defeated Sissy's chin quivered as he fought so hard to hold back his tears. 

As she walked into the room and saw her transformed Sissy stepson for the first time, she screamed. "OH MY GOD!"  She nearly collapsed with laughter as she drank in her little Sissy.  Of course Sissy Charleen was dying of humiliation, but he stood there, eyes lowered, as he had been trained.  The Stepmother eyed Sissy Charleen's bust and asked aloud, "Are they real?"  She brazenly walked up to Sissy Charleen and gave his boobs a rough squeeze.  "OH MY GOD!" she screamed again.  "They are real!"  Her riotous laughter resumed.

"Come along, Sissy Charleen.  Time for us to go home.  But first we're going to go downtown so all of your old friends can get to see the new you!"

Sissy Behavior Modification

As a professional Sissy Trainer, I have learned how to be very strict.  And I'm not afraid to dish out severe punishment when required to get my Sissies to comply with my requirements.  I'm not shy about using my cattle prod or landing out a few dozen lashes with my riding crop when I'm dealing with a reluctant Sissy.  But as a woman who stands 5' 7" and weighs 130 pounds, sometimes I just don't have what it takes to give a Sissy the punishment he deserves.

Sissy Daisy was a real problem for me.  Even though his physical transformation had proceeded beautifully, he refused to embrace his future as a submissive Sissy pleasure toy.  He insisted that he was a man!  HA!!!  And he refused to entertain male guests that I frequently invite to my home.  For his disobedience, I tried everything:  beatings, starvation, locking him in a dark closet for days at a time.  But nothing worked.  It was time to bring in an expert.

I brought Sissy Daisy over to visit my friend, Master Steed.  Master Steed, you see, is a sadistic, brutal man who enjoys inflicting pain on bad little Sissies.  He is insanely strong and muscular.  And best of all, he is hung like a horse!  When your Sissy needs some extra encouragement, Master Steed is the one to call.

I dragged Sissy Daisy into Master Steed's home and we waited in the living room.  Sissy stood silently in the corner wearing a pretty sundress while I made myself comfortable on the sofa.  Sissy Daisy was so nervous, not having any idea where he was or what was about to happen to him.  I set up my camcorder on a little tripod because I love having a souvenir of these visits to Master Steed's home.   I was getting very excited just thinking about the show I was about to witness. 

Then Master Steed entered the room, shirtless, his huge muscles bulging.  Sissy Daisy was instantly terrified.  He tried to run from the room but Master Steed was on him immediately.  Master Steed hit the Sissy hard, once in the face and once in the stomach.  Sissy Daisy screamed in pain and his tears began to flow.  In one swift motion, Master Steed ripped the sundress off of my Sissy, leaving him completely naked and exposed.  For the next 20 minutes, Master Steed slapped, spanked, pinched, twisted and otherwise tortured my misbehaving little Sissy. 

And then the best part.  Gripping my Sissy's throat, he spun the Sissy around and rammed his massive dick into his tight little bottom.  Sissy Daisy was sobbing like a little bitch and begging for me to make his punishment stop.  I nearly came myself watching my little Sissy getting raped.

That's when I noticed Sissy Daisy's nipples were getting hard!  That little Sissy bitch was getting excited by being fucked by a real man!

I couldn't stop myself.  I jumped up from the sofa and grabbed Sissy Daisy's hard nipples.  I pinched and twisted them hard while  I shouted into the little boy bitch's face, "I can see that you are really enjoying this, aren't you Sissy?  Your nipples don't lie!  You like having a huge cock up your tight little boy pussy, don't you?"

Well, needless to say, Sissy Daisy has been a delightfully obedient Sissy ever since that day.  No more protests, no more denial.  He'll service my male guests and do whatever else I tell him to do.

And just for fun, once in a while I make Sissy Daisy watch his special video with me.  I certainly wouldn't want him to ever forget that special day. 

A Sissy Girlie-Boy - Part 5

"Get on your knees," Manny instructed.  I did as he said.  He stood and said, "Take off my pants."  I struggled to unbuckle his belt because my hands were shaking so much.  "Hurry up," he said.


I managed to unzip his pants and pulled his pants down.  And that's when I saw it -- the most enormous cock I had ever seen.  It must have been 10 inches long and really thick.  It sprang to life, right in front of my face, as I freed it from his pants.  I fell backwards from the shock of seeing this monster.  "Get up, you stupid Sissy!" Mommy screamed, as she kicked me.


I hurried back to my knees.  I wasn't really sure what I was supposed to do next.  But Manny made it perfectly clear.  "Suck it, bitch," he said, grabbing the back of my head and pulling me hard into his crotch.  At first I didn't open my mouth, but then Manny roared, "I SAID SUCK IT, YOU SISSY BITCH!"


Terrified I opened my mouth and put Manny's massive tool inside.  It tasted terrible.  I couldn't believe this nightmare was really happening to me.  But anyway, I must have been doing something right, because Manny started moaning as he pumped his big dick in and out of my mouth, his hands firmly holding my head in place.  "Mmmm, yeah," Manny said.  "That bitch has one sweet Sissy mouth."


"Jackie's really enjoying that, isn't he!" Mommy said with evil delight.


"Come on, Manny," Frank said impatiently.  "Let's go, I need to get back to work."


"Get up on the couch," Manny instructed, pulling his cock from my mouth.  "Get on all fours, like a Sissy doggie and stick your ass in the air."


I did as he commanded.  Manny roughly yanked my tight panties down.  I could feel him rubbing the tip of his cock inside the crack of my ass.  I knew what was coming next.  I squeezed my eyes tightly shut and prayed for this to be over.  And then I felt Manny start to push his big rod into my lubricated bottom.  As the tip of his cock started to enter me, it was painful and horrible but I thought I could tolerate it.  But then he started to push the rest of his massive dick into me.  I screamed in pain as inch after inch of his massive cock drilled deeper and deeper into me.  I was sure that his cock was going to rip me apart from the inside.


"For God's sake, Jackie, SHUT UP!" Mommy shouted over my own screams. 


"Yeah, shut up, Jackie," Manny repeated, laughingly.


The next thing that I remember, Manny wrapped his big arms around me, one around my waist and one across my chest.  With his steel rod pumping inside of me, Manny lifted me off the couch.  I was literally suspended beneath him as he banged away at me.  I continued to scream in pain and begged him to stop.  Still carrying me beneath him, Manny turned away from the couch and towards Frank and Mommy.  It was horrible being fucked by this giant -- but it was made even more horrible that I was now face-to-face with Mommy while it was happening.  And that's when Mommy slapped me -- hard -- across the face.  "Stop that awful screaming!" she shouted into my face.

And then Manny started breathing really hard.  His arms wrapped more tightly around me -- so tightly I could barely breathe.  I knew what was about to happen.  His pumping became harder, almost violent.  His big hard cock became bigger and harder.  And then he came.  I could feel his hot cum blasting into me.  I started to cry.

After a minute, he pulled out of me and literally dropped me on the couch.

"Not too bad," Manny reported to Frank as he left the cubicle, without even looking at me after dumping me on the couch.  "But he gonna have to shut the fuck up.  No one wanna listen to all that."

"Get cleaned up," instructed Frank.  "Customers will be showing up soon."  To Mommy he added, "That Sissy better not make so much noise with my customers."

Mommy just glared at me as I continued to cry.

Sissy's Anniversary Surprise

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An Adopted Sissy Daughter

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

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

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

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

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

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

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

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

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

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

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

I nodded in agreement.

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

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

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

Making a Perfect Housewife

Sissy Candi was an occassional crossdresser who liked going to the local drag bar on Saturday.  Sissy Candi was young and pretty, but also shy and nervous.  He kept mostly to himself, nursing a glass of white wine while watching the drag show and the scene aroung him.

That's exactly how Master Drake found Sissy Candi when he sunk his claws into him.

After luring Sissy Candi to leave the bar with him one Saturday night, Master Drake imprisoned the poor innocent sissy in his home. Master Drake forced Sissy Candi live as a woman 24/7. 

Through relentless beatings and mind games, Master Drake stripped Sissy Candi of any sense of confidence or self.  He lives now in a continuous state of nervous fear and dependence.  Poor Sissy Candi. 

Master Drake forcibly transformed Sissy Candi from a part-time crossdresser who enjoyed exploring his feminine side on Saturday nights to a full-time Sissy Housewife.  Master Drake insists that Sissy Candi act and look like an obedient, docile and devoted 1950's-style housewife who lives only to serve and please her "Husband."