Deuteronomy 22:5
לֹא-יִהְיֶה כְלִי-גֶבֶר עַל-אִשָּׁה, וְלֹא-יִלְבַּשׁ גֶּבֶר שִׂמְלַת אִשָּׁה: כִּי תוֹעֲבַת יְהוָה אֱלֹהֶיךָ, כָּל-עֹשֵׂה אֵלֶּה.
A woman may not dress in a man’s apparel, nor shall a man wear women’s clothing; for doing these things is abhorrent to the Lord your God. [Translation Rabbi Steve Greenberg]

Suggested Discussion Questions:

1. Rashi thinks that cross dressing is a ploy used by a potential adulterer to gain easy access. Ramban and Rashbam both think think that the cross-dressing male is planning a tryst with a woman and using dress up can help him stand out i a crowd. Which do you thinks make more sense?

2. Sexual intent for cross-dressers seems the be the problem in BT Nazir 59a. What does this demonstrate?

Time Period: Biblical (early ancestors to 165 BCE)