Me again!  I could not let this one go, so below is my expanded ending.  I hope the Author does not mind.
----------------------
Old
Automatically Kelly took the proffered hand and shook it. Judith smiled then turned and left the flat.

Updated and new
Automatically Kelly took the proffered hand and shook it. Judith smiled then turned to leave the flat.
Kelly said "Wait."  Judith stopped and looked at her.  Kelly asked "Will you walk around the shops with me?"
Judith asked "Why".  Kelly replied "To have some company, for the first time, just to have some company."
Judith smiled and a second later nodded.

As written
Turning to the mirror Kelly stared at her reflection, her mind racing as she tried to think of a way to escape the situation she found herself in. But it was hopeless and she knew it. Then again, she thought, "It might be quite exciting and just think of the new clothes." She reached into her handbag for her lipstick and touched up her lips as she remembered what Judith had said. "Many years since she saw anyone as attractive as I am eh?" She smiled and picked up her handbag and walked to the door, one more promenade along the street before she had to become boring Gary again.

New
Judith and Kelly walked out into the night and walked back to the town they had just come from.  There were no words between them and Judith let Kelly choose the route.  The mall had less persons in it now so they went through it around the external shops and eventually back to that same cafe and stopped.  Here Judith looked at Kelly and Kelly looked at Judith, Judith nodded and departed and Kelly watched her walk away.  Judith did not look back as she had no need to. Kelly took a deep breath and started the walk back to the flat to change back to his drab clothes.  On the way back Kelly thought it was nice to have a companion for that walk, it felt right to be with another person, a women on that walk.  Yes it felt good.  Walking back Kelly thought about the job she had been blackmailed into and gave a little shudder.  Perhaps she may be able to afford another quality wig, perhaps a blond one or a dark dark brown one, Kelly smiled at that thought as she put her best foot forward hearing her feet click clacking as she walked along gaining a few stares from other people still out and about.

Judith got back to her car and made one phone call.  "We got her!" Ending the call she smiled, started her car and drove away.

Interesting and intriguing story.  A follow up would be really good to see how Kelly took up the new roll and how she performed.
I am glad she was very adamant about being straight.
One twist I would have put into this story would have been for Kelly to ask Judith, just as she is about to leave the house, to walk with her around the shops and for Judith to have accepted the offer.  Few words being spoken on the walk and Judith taking her leave as Kelly heads back to her house.

I think that kind of take on the Titanic would be pretty innetestirg.  I'd have to do more research on the Carpathia.  I'd be happy to work on a collaboration if you know a lot about that particular event.As far as an author website, I'm a huge livejournal fan, so I'm happy for the moment.  If I seem to outgrow this, I would love to take you up on your offer.  One of my livejournal friends who is a graphic designer is already working on a custom header bar and background for me for livejournal, so I'll go with that for the near future.  Thanks for the offer though!Elaine

You know how to write  good stories. But I think that you prefer to write bad stories like that. Nothing forced is good, you know?
I'm sorry.
Silvia.

the story is good but its to short  i would have liked to know more about kelly first and how he started dressing  its intresting as well

An interesting little story about the results of crossdressing. Not quite what you think from the way it begins. Writing is good with detail and description.