I agree with the other comment about the wine suddenly appearing after he refused Steve's drink offer earlier.  Now as to the story and to the author generally, let me say, GREAT JOB!  I find your stories to be very interesting; each one has a unique and clever plot-line.  I love the idea that your heroine, in almost all of the stories, gets involved with a relative, an in-law, a co-worker, a boss -- essentially someone they know in their male persona.   So the sex is super-charged!  You write so well, Bethany!  I do, however, have a general suggestion to improve upon this story (and this critique applies as well to many other stories of this genre):  a little less perfection please! Women, as well as men who portray women, are human!!  They get runs in their stockings and chips in their nails, and their shoes don't always match their handbag!  And you'd have to be a rather practiced make-up artist to perfectly apply false eyelashes, liquid eyeliner and three coats of mascara on the lower lashes -- well beyond the capabilities of a part-time closeted transvestite like George!!!

Great story, I loved reading this one a lot.  You write great short stories.  I wish I had that talent.
One little thing kind of jumped out at me while I was reading it:  When George's boss offers him a drink when he first comes in the door, he declines the offer and then when George is getting dressed he all of a sudden has a "sip of white wine".  It is a small sort of disconnect that doesn't really detract from the story's overall well written content.
I love reading your stories.  Please keep writing them.
Ryan