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.

Afternoon Sissy

Whenever I am home alone, I love playing dress-up.  I raid my mother's closet, her lingerie drawer, her make-up, jewerly, perfume -- everything.  She even has a long curly wig that I use to complete my look.

I love dressing up like a girl.  I feel so feminine, so free, so alive.  I love getting my make-up perfect and slipping on the wig.  I especially like wearing my mother's sexy lingerie.  Dressed like this, I enjoy staring at my pretty reflection in the mirror looking back at me.  Sometimes I take photos of myself, like this one, that I can look at late at night when I'm in bed.

But today, disaster struck.  I had the house to myself all afternoon -- I thought.  My mother was at work and my older brother was at football practice.  I was all dolled up, wearing my mother's light pink, lacy nightgown.  I was in the living room, dancing to the radio and watching my performance in the big mirror, when all of sudden in walked my brother and three of his friends from the football team.

"What the fuck!?!?" my brother shouted wen he saw me.

"Who's that?" one friend asked.

"That's my faggot little brother," he answered.  The other boys howled with laughter when they recognized me.

"He sure is pretty," the biggest of the friends said.

"Hey," another one said. "Even though practice was cancelled, I think we can still get a workout this afternoon, if you know what I mean."

"Go ahead," my brother said.  "I don't care.  Do whatever you want with him."

And with that, the three boys dragged me upstairs to my bedroom to be their "Sissy Girlfriend" for the afternoon.  Thet took turns having sex with me while the others held me down.  I tried not to cry, but they were really rough with me and it hurt a lot. 

When they were done with me, one of them said that I was cute enough to be a cheerleader -- and if I was a cheerleader then I could get fucked by the boys on the team all the time.

Hmmm.  Maybe I will...

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!



Mother's Pretty Little Sissy Daughter -- Part 1

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

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

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

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

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

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

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

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

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

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.