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.

Dressing for Sissy Success

 It's a very exciting moment when your Sissy is ready to be sent off for his first day of work.  I have made arrangements with a few local businesses to hire my Sissies as receptionists and secretaries. 

I have a wonderful arrangement with these local businesses.  For $3.00 per hour (paid directly to me of course) they get the services of a meek and eager-to-please Sissy.  I ensure that all my Sissies are well trained and so it is a real bargain for the employer.  And of course, if the boss wants some "extra service" from his newest employee, well that's fine with me.  I don't care if my Sissies spend half their day on their knees under the boss's desk with a big cock in their mouth.  As far as I'm concerned,  the boss is always right!

The only condition I place on the employers is that I insist that everyone in the workplace know exactly who and what my Sissies.  Sure, many of my Sissies could pass as just another genuinely female bimbo -- but that's not what I want.  I want everyone to know -- from the other girls in the office, to the big hunks on the loading docks, to the salesman that visit the office -- that the sweet little thing serving them is a Sissy.

When it's time to send your Sissy off to work, I think choosing the right wardrobe is terribly important.  Your Sissy's outfit needs to scream femininity.  It needs to be sexy and impractical.  It needs to show off your Sissy's new curves and as much cleavage as possible.  It also needs to be something no genuine woman would wear to the office.  In fact, I try to dress my Sissies in a way that infuriates and insults the other women in the office, making the Sissies' life just as uncomfortable as possible.

Dressed this way, there is no way that your Sissy's life won't start to get complicated.  Some man is going to start hitting on your Sissy -- maybe a Salesman visiting the office, maybe one of the janitors -- who cares.  And my Sissies are trained to never --  never ever -- say no to the advances of a man.

So here are a few of the outfits I have picked out for my working Sissies recently.  It can be so much fun to dress up your little working Sissy like this and then enjoy the show!

The Busy Life of a Sissy Servant

Sissy Daniela feels completely fulfilled by his/her role as the submissive, obedient servant of the Mistress that he/she adores. He happily gave up everything he once had as a man -- his job, his family, his life savings, and most of all his free will -- in order to be able to serve his beloved Mistress 24 hours a day. Sissy Daniela works tirelessly as the Mistress's sissy maid, her sissy secretary and when necessary, her sissy lover. In return for his/her devotion and service, Sissy Daniela receives the Mistress's firm and expert guidance in being transformed physically and mentally into a beautiful, docile sissy servant.

It is not easy being a sissy servant to a demanding and strong Mistress. It is only 5:30 in the morning, but our pretty little Sissy is already awake, bathed, and his/her hair and make-up are done to perfection. Still dressed in only his/her pretty bra and exquisitely tight girdle, Sissy Daniela checks the list of chores for the day. Soon he/she will don the morning service uniform and apron and prepare the Mistress's breakfast, beginning another day of servitude.