Sunday, July 8, 2012

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! 


  1. I just love these stories and its great that you can even save money because of your sissy, so they do have uses
    Kira x x x

  2. So nice to hear how well sissy step son's training has paid off. S/he's turned out to be quite the little slut, much to hur own horror s/he's now a cock sucking whore, and all for Mommy's benefit and enjoyment! I've started a new series of stories about sissy Bobbi at my blog, please cum by and give them a look.

  3. A marvellous well trained sissy slut you made out of hur while you benefit financially from it! Good on you!

  4. I hope you don't mind me quoting you. Iloved this and it so fitted my latest blog post. If you do mind i will take it off of course...

  5. Delighted that you enjoyed this story and happy for you to use it in your blog. If you can, please Follow my blog and add a link to my post. Enjoy!

  6. one of the best you have done,, i love it so much xx