Sunday, October 31, 2010

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!


  1. love this insight and expertise on sissy owning and sissy culture, but i would insist on much more than 3 pounds an hour not that the Sissy would ever have any say in how its spent, or the employer at least paying for the sissies clothing and cosmetics budget!

  2. Linda ... Could You please dress and train me as one of Your sissies ? ... Please? ... That post made me sooo wet x


  3. Love your plan for your sissies. I think you should charge enough that their clothes and make-up are paid for. The outfits you've selected are great and I really like the redhead.

  4. Screaming femininity, sexy, impractical, uncomfortable. Humilliating someway, so no real woman would wear. Thats the kind of outfit i crave to wear.

    I like the way you deal with your sissies. I would love to be part of them.

  5. A lowcut blouse, 13" pleated skirt with garterbelt, stockings and 3" heels would be thing to put a sissy like me in to work in an office of either dom women or alpha males. Or a thin short maids uniform with lace as a cleaner/maid of all things.
    You see Linda Trainer, humiliating attire no ordinary woman would wear is what Your sissy craves and can be controlled by

    1. No way I'm going to be dressed up like that in an office!" I like to see you try that I'm a man, not a sissy! Belinda?" I wear the pants, you wear the dress?" Macho man Mike N.