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 Sweet Sissy Escort

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

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

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

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


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

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

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

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

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



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

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

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

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

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

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.

My Perfect Sissy Housewife

Two years ago, my husband finally admitted to me that he was a crossdresser.  Of course, I had figured that out years earlier -- but I just waited patiently for him to finally admit it to me.  And during those years of waiting, I had been thinking long and hard about how I was going to deal with my husband's crossdressing.

So when he finally said something, I let loose with my well prepared list of demands.  I started by telling him that, from now on, I would be wearing the pants in the family.  My career was really taking off and his was going nowhere.  I decided that I would like to have a sweet little housewife taking care of me and my home full-time.  That would be his job from now on.

And he would not be just any housewife.  Oh no.  He would take the role of a traditional, obedient, submissive homemaker from decades past.  He would live and dress the part.  Every detail would have to be perfect and to my liking -- from his pretty hair-do, to his pleated skirt, to the sheer hostess apron tied aroung his trim little waist to the smile on his pink, glossy lips as he went about his chores.  His endless chores!

At first, he tried to protest but he was simply too much of a sissy to fight me.  I started implementing our "lifestyle changes" right then and there.  I made him hand over his license, credit cards and passport -- and watch as I ran them through the shredder.  Within a week, I had him empty every closet and drawer of his old clothes and reminders of his old life, which I refilled with his new homemaker fashions.  Within a month, we had moved to a new town to make it easier for us to restart our life as a high powered lady executive and her devoted, old fashioned housewife and partner.

That was two years ago and my husband is now been completely transformed, in body and mind, into the gentle, doting housewife I wanted.  He has become completely proficient at doing all his housewifey chores, from cooking, to cleaning,to giving me footrubs, to preparing my martini when I get home in the evening.  Here he is doing the laundry.  He takes such pride in being the perfect housewife.  Look at how happy he is knowing that he is pleasing me.

I have recently started dating one of the senior partners at my law firm.  He will be coming over to my house tonight for a romantic dinner that my hubby-housewife will prepare and serve.  If the date goes well, hopefully my sissy will be serving us breakfast in bed as well.






'

A Sissy Gets Married Off

I had known about my husband's feminine urges since before we were married.  I didn't mind his cross dressing or his need to be submissive to me.

At first this was exciting for me too.  I had always had a dominant streak and my husband's Sissy submission to me fulfilled certain needs I had as well.  But eventually, I tired of the game.  In my strict hands, my husband had progressed from a weak-willed, cross-dressing male to a beautiful, fully feminized submissive Sissy.

I needed to make some changes in my life.  Most importantly, I needed to kick my Sissy husband out of the house so my new lover could move in with me full-time.

My Sissy husband was very upset when I explained that I had arranged to marry him off to a man I had found who was looking for a Sissy wife.  There were lots of tears and he begged for me not to go through with this, but I had made up my mind.  Anyway, who cares what a Sissy wants?

That was six months ago.  I am now very happily living with my handsome lover and my Sissy ex is living with his new Husband and Master.  My Sissy ex's entire life now revolves around pleasing his Husband and Master.  He spends hours each day ensuring that his hair and make-up are perfect as his Husband requires.  He toils around the clock to ensure that the house is spotless, clothes are washed and ironed, and that meals are on the table when his Husband returns home from work.  And of course, my Sissy ex has to satisfy his Husband and Master's endless sexual needs as well.

From the photos I've seen, it looks like my ex is starting to embrace his new life as the Sissy wife to a real man.   He certainly seems to enjoy being treated as a "lady" by his strong and dominant Husband.  Look at how he smiles as his Husband and Master touches him with his rough, strong hands.  Look at how he moans with pleasure when being kissed and having his Husband fondle his big boobs.

I guess it was always his destiny to be the submissive Sissy wife of a real man.


 

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."

Poker Night Sissy

Every Friday night, Master invites five or six of his friends over for poker night.

Master insists that I get all dolled up in a fancy cocktail dress, 5-inch heels and sexy make-up.   My strapless dress barely covers the large breasts Master forced me to get.  He says I have to look my best when his friends are over.

At 8:00 the guests begin to arrive.  I greet them at the door and take their coats.  Always keeping my eyes lowered, I inform them that I am the "sissy of the house" and that I have been instructed to serve my Master's guests in whatever way they require.  As I say this, I can feel their hungry eyes on my exposed cleavage.  I can tell they are smirking at my humiliation and submissiveness.

For the next four hours, I serve them drinks and snacks.  The men play cards and drink and smoke and laugh.  Mostly they ignore me, but they often grab my ass or squeeze my boobs when I am serving them. They say mean things to me and call me "whore" and "slut" while they fondle me.  When I'm not serving the men, I stand silently in the corner and wait.

Then, promptly at midnight, the men put down their cards.  The game is over and they count their chips.  They carefully figure out who won, who came in second, third, and so on.  Then they line up, the winner in front.  It is now time for me to do what I have been dreading all evening.  I drop to my knees in front of the winner, I pull down his pants and I open my mouth.

The night's winner jams his big dick into my mouth and I suck and lick it eagerly the way Master trained me. The winner's dick get bigger and harder.  He roughly bucks his hips, ramming his cock in and out of my mouth for several minutes.  Then he grabs the back of my head and forces his cock down my throat.  And then he explodes.  He blasts his hot, sticky cum into and I swallow it all.  All the other men hoot and shout as they watch the winner cum in my mouth.

"Next!" Master yells to everyone's amusement and the next man in line drops his pants.  I put his cock in my mouth and let him rape my face.  I repeat this until each man has unloaded his sperm into my mouth.  And for being the night's winner, I have to give the first man a second blow job.

I feel sick and disgusted, with the load of several men in my stomach and on my face.  "Get yourself cleaned up!"  Master yells at me.  "What a whore!" he adds to the amusement of the others.

I race to the bathroom and quickly wipe off my face and redo my lipstick.  I rush to get the men's coats and to see them out.  They usually have something mean to say or enjoy one final laugh at my expense as they leave.  With the final guest gone, I get busy cleaning up after the night's game.

With the house clean and the clock striking 3:00, I enter Master's bedroom where he has been sleeping.  I pull back the covers and begin performing my last blow job of the night on my Master's massive cock.  "You are such a filthy little sissy slut," Master mutters, half asleep, as I begin to cry.

Sissy Pets -- Part 1

During the past two years, there has been a hot new trend for Sissy owners and collectors. Instead of ordering big breasted, totally transformed artificial girls, some Masters are now ordering partially transformed Sissies. Allowing no surgery and often no hormones, these Masters like to own a forcibly sissified boy who they keep in a permanent state of sexual limbo and torment.   Although these Sissies sometimes have long hair and wear make up, these femme boys are not allowed to pose as girls. They are  Sissies. They are often dressed in cute little Sissy outfits and don't even get to have a girly name.  I call these things "Sissy Pets."


"Sissy Timothy!"  Master bellowed in the crowded restaurant, attracting as much attention as possible. Sissy Timothy scurried back to the table having checked his Master's coat.   Poor Timothy's face was bright red, feeling every eye in the restaurant staring at him as he raced back to his Master's table. The other restaurant guests laughed seeing Timothy in his humiliating sissified state.  His outfit was Sissy perfection -- a silky blouse with an oversized collar,  shorty-shorts, sheer anklet socks and platform sandals.  He was near tears having his sissification being displayed so publicly.

Master ordered their dinners in a loud voice.  "I'll start with a vodka Martini and then I'll have the steak. My Sissy will have a glass of skim milk and the mixed greens, no dressing. I need my Sissy to keep his girlish figure!" he added to the delight of everyone in the restaurant.

While they waited for their food, Mster took out his cell phone and snapped his fingers twice. Sissy Timothy leapt to his feet and immediately began to massage his Master's broad shoulders, while Master conducted some business on the phone.

When their food arrived, Master put away his phone and told Sissy Timothy to sit.  "Sissy, I have some fun plans for us for tomorrow."  Sissy Timothy looked up from his salad with dread.  "After your ballet lesson, I thought we would go to the mall and buy you some pretty new dresses.  Wouldn't you like that?"

"Yes, Master, I would like that very much.  Thank you," Sissy Timothy obediently replied, horrified by the idea of it.  The other restaurant guests listened to the conversation with amusement, fascination and confusion.

My Sissy Assistant -- Part 2

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

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

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

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

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

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

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

My Sissy Assistant -- Part 1

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


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


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


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

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













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

A Sissy's Titties Are Put to Good Use

Look at my pathetic sissy husband now!  And to think that I endured years of abuse from this sissy faggot.

Two years ago, he accidentally left his computer on and I saw that he was visiting this website, Linda's Tormented Sissies and Forced Feminization Captions!  I was absolutely horrified by what I saw in this blog.  It was filled with disgusting stories with graphic pictures about men being forced to become sissy playthings for their cruel Masters and Mistresses.

After discovering his internet habit, I started going through his closets and drawers to see what else I would find.  Well, not only did I find a whole suitcase of women's clothing that he must dress up when I'm not home, but I even found a stack of magazines called "Forced Womanhood." Gross.

I didn't waste any time.  Within 48 hours, I "enrolled" the little sissy in a forced fem clinic, arranged for a divorce and got on with my life. 

Now, two years later, I have a whole new life.  My ex-husband is back home -- but he is now my sexy, big boobed sissy slave.  He is now completely docile and obedient.  And serves me -- and my hunky new boyfriend --  whenever and however we desire. 

My boyfriend has an enormous cock.  Monstrous, really.  And he really enjoys tittie fucking my ex!  First he pours some ice cold lube between hubby's tits.  Then he starts ramming away.  Hubby has been trained to press his big boobs together around my boyfriend's cock.  And on every stroke, my sissy hubby has to open his mouth wide to accept the head of my boyfriend's huge cock.   In and out, up and down, back and forth -- my boyfriend's huge dick rams into my ex's mouth -- over and over and over. Until my boyfriend cums.  Then he rams his dick deep into my sissy's mouth and pumps his hot cum down my ex's throat.

Sometimes I get out my camcorder and video my sissy hubby's tittie fucking performances.  Maybe I'll post these videos on Linda's Tormented Sissies site!



750,000 Page Views!!!

Hello all you little Sissies and Sissy Owners and Trainers!

My blog has now had over three quarters of a million page views!  Isn't that exciting!!!

This tells me that there a great many Sissies in need of strict training, manipulation, captivity and humiliation.  And there are many Sissy Owners (and men and women who wish they had a Sissy of their very own) who are very interested in learning more about the art of forcibly transforming a male into a Sissy plaything.  I am delighted to see how large -- and how global -- our community is!

But listen up, all you pathetic little Sissies.  If you are a Sissy and you are visiting my site, I am INSTRUCTING you to leave Comments.  I am very pleased with the Sissies (and Masters/Mistresses) who have been leaving Comments.  But I am VERY disappointed in you Sissies who are visiting this site in secret.  That is not permitted!  Part of your Sissy journey REQUIRES you to put your Sissiness on display for all to see.  Express yourself to your community of Sissy sisters and superior Masters and Mistresses by commenting on the stories and pictures posted.  Share your Sissy feelings about the stories, your Sissy dreams, your Sissy fears.

The little Sissy in the picture is being punished for being disobedient by his cruel and demanding Mistress.  Ouch! You too will be punished if you continue to disappoint me.

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."

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."

My Cute Sissy Dress

When Mistress came home from work this evening, I was wearing my little maid's dress and greeted her with a curtsey, as I did every evening.  I took her bag and coat and brought her a glass of wine while she relaxed in her big chair in the living room.  As she sipped her wine, I busied myself massaging her feet as she told me about her plans for the evening.  

"We're going out tonight," she announced.  "Go put on that cute, pale yellow sissy party dress I bought you last week."  I stood up, curtsied and went to my room to change.

I was nervous as I put on my pretty little dress.  It just screamed "Sissy!"  Where ever we were going tonight, I was sure to attract a lot of attention.  It was made of sheer material and had a ruffly trim on the big collar and cuffs.  The skirt was both comically full and embarrassingly short.  I hated wearing it!  As I slipped out of my maid's outfit, I saw my reflection in the mirror.  I was surprised by how weak and skinny I looked.  I must have a few more pounds last week.  I put on my yellow sissy dress as instructed and returned to the living room.

When I returned to the living room, my Mistress as there, dressed all in tight black leather -- tight leather jeans, tall black boots and her black leather jacket.  I froze with fear when I saw her.  "That's right!" she said with an evil smile.  "Tonight we're going to the biker bar!"

"Oh, please no!," I pleaded.  "Not dressed like this!"

Well Mistress did not like hearing my protest.  She slapped me hard across the face.  "Sissies are NOT allowed to complain!" she screamed at me, slapping me hard across the face again.

"I'm sorry, Mistress. It won't happen again," I replied meekly.

"That's better,  Now get in the car."  And off we went.

The night was just as horrible as you can imagine.  The bar was packed with dozens of big, hairy men -- all in leather and jeans, covered with tattoos and smelling like beer and smoke.  And there was I, in my sweet little yellow Sissy dress.  I was the center of attention.  I was surrounded by men who, at first, were just laughing at me and calling me names.  But soon, some of the men started rubbing against me and feeling me up.  Then they started taking turns kissing me.  They would wrap their big arms around me and hug me so hard I could barely breathe.  I could feel their cocks get hard through their tight jeans as they pressed against me.  This went on for hours.  All the while, Mistress watched with delight from a stool at the other end of the bar.

Sometime around 1:30, I went to the ladies room.  But when I came out, Mistress was gone.  The bartender said that she left with a couple of guys.  I was stranded!  One man offered to drive me home...in the morning.  I didn't have any options.  I left the bar with him and rode on the back of his Harley back to his trailer where we spent the night.  Needless to say, I didn't get much sleep that night as the man took full advantage of having a stranded Sissy in his bed.  

When I finally got home Mistress yelled at me for not having her breakfast ready.  I curtsied, apologized and went into the kitchen to prepare my Mistress's breakfast.      

Rotten Stepson becomes a Perfect Sissy

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

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

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

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

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

Sissy Goes Outside Part 4

Something strange happened last Friday when I went over the Tasker brothers' house.  I wore a pretty dress and did my make-up like always.  I arrived as instructed at 4:00 sharp, and after posing for some photos and scrubbing the toilets, I readied myself for Dick and Ben to start fucking me, using me as their Sissy sex toy.

Dick, who always fucks me first, told Ben that he didn't need any help holding me down.  He told Ben to "get lost" until he was done with me.  Ben seemed confused at first, but eventually left Dick and me alone in the bedroom.  Dick pushed me down onto the bed and climbed on top of me.  Then he started kissing me -- a lot -- on the mouth, on my face, on my neck.  Instead of holding my wrists down he told me to wrap my arms around him.   Then he slowly pushed his giant cock inside my lubricated bottom and started to gently pump it back and forth.  He had never had sex with me like this before.  It didn't even hurt very much this time.

And after he came inside of me, he kept his cock inside of me for a long time and started kissing me again.  Then he whispered, "You are so hot," in my ear.  For some reason I suddenly felt warm all over when he said that.

Then Ben started banging on the bed room door, shouting, "Hey, hurry up in there!  It's my turn!"

At first Dick just kept on kissing me, trying to ignore all the noise his younger brother was making.  But after a few minutes, Dick leapt out of bed and swung open the door.

"About time!" whined Ben.  "What the hell have you been doing in there?"  Ben started taking off his shirt as he headed towards the bed I was lying on.

Dick grabbed Ben's arm and said, "It's not your turn.  I'm not sharing him any more.  He's my Sissy now.  Only mine.  So get lost."

Well, Ben went nuts when his older brother said that and they started fighting.  I wanted to get far away from this fast, so I grabbed my shoes and my purse and left. 

Later that night, Dick called me on my cell phone and told me that I would be spending afternoons only with him from now on.  He said that he was going to move out of his house and start subletting a friend's apartment downtown.  Dick said that I was to meet him there every afternoon at 4:00.   So on Monday afternoon, I did as I was instructed and met Dick at his new apartment.  

Here are some pictures of me that Dick took on the balcony.  I'm wearing a pretty blue dress from my sister's closet and a purse and shoes from one of her friends.  I spent extra time on my hair and make-up because I really wanted to look nice for Dick.

When Dick saw me he told me that I looked "really pretty" and kissed me.  He took my hand and led me inside.  He sat down on the coach and told me to sit on his lap.  He started kissing me again and running his hands all over me.  "You are so sexy," he panted into my ear.  It made me feel a little dizzy when he said that.

After a few minutes of making out on the coach, Dick told me to go down on him.  I slid off his lap and got on my knees between his legs.  I undid his belt and his pants.  Once freed, his enormous cock sprank to life.  I held his rod with one hand and started licking it up and down.  I know he enjoyed that.  I then put his stiff cock in my mouth and started sucking on it.  Dick wasn't forcing me to do anything.  I was trying my best to please him.   I used my hands and lips and tongue to drive him into a frenzy.  When he started to cum, I made sure that I swallowed every drop.

Later Dick carried me into the bedroom and gently made love to me.  I moaned with pleasure as Dick's big tool slowly worked itself in and out of my bottom.  After Dick came inside me, we just lay together in bed, my head resting on his broad chest, his big arms wrapped tightly around me.  I felt so safe and warm.  And I felt so happy knowing that I had pleased my man so completely.