Okay okay. There's a story to this, I swear
Well, a story from inside my head.
Originally, he was gonna be asked if he liked the dress and he'd say he neither liked or disliked it, because, well, he's Data. He has no emotions. (this is BEFORE his emotion chip :3)
Buuut, as I was drawing it, it just turned out this way

more dialogue would've cluttered it. There were gonna be more characters, too, but I was lazy.
If you don't get what's happening, Commander Riker sent faulty orders to Data via his Captain's Ready Room.
Enjoy?
Done in Flash.
Comments
Ctarl Says:
I always felt that Riker would on some days just play jokes with Picard.
Cat Megex Says:
But...wouldn't Data have known that it wasn't Picard's voice?
Jandreau Says:
zololover Says:
PICARD'S GONNA RAPE DATA~~!!! DD8 >runs away.......& watches<
rofl i love this~~x3 
Dipswitch Says:
LOL another win. he would do that, too
Aquathros Says:
*gigglesnerk* OMG! Data in girly clothes! ROFLOL!! You win teh internets!
ChibiKeba Says:
Cross dressing Data, you don't get much more hilarious then that
Minstrel Ayreon Says:
OH MAN...LOL!!!!

I must say, even caricatured like this, you really did capture the characters' appearance PERFECTLY! Not to mention the hilarity of the entire scenario.