Response from my friend:
I think you are on the mark. The issue of transvestitism was never even
considered in our (former) Pentecostal circles, but rather, their theology
was largely drawn from a reaction against changes in clothing styles back in
the early part of the 20th century. As was not uncommon, they just found a
verse to hang it on.
However, the fact that transvestitism and cross-gender values were a central
part of the Canaanite fertility cult is vividly protrayed by the graffiti
discovered on a large pithos (storage jar) at Kuntillet 'Ajrud about 30
miles or so south of Kadesh Barnea to the south of Judah. There are three figures
in the composition plus an inscription suggesting a bold syncretisim in
which Yahweh is depicted as having an Asherah (a female divine counterpart).
The two foremost figures seem to represent Yahweh and his female consort, a
crude distortion of all sorts of biblical norms in the Torah and elsewhere.
The third figure is a musician. The central figure is clearly androgynous,
since it features both female breasts and male genitalia. Both figures are
linked with Bes, an Egyptian demonic deity, and while bi-sexual deities were
unknown in Egypt, they certainly appeared in the Levant in more than one
instance by the Iron Age.
The passage in
Deuteronomy 22:5 seems very much at home in such an
environment which encouraged trans-gender expressions. If the creation
acount in which God made humans male and female is normative for human
existence, then Canaanite trans-gender expressions would be fundamentally in
tension with such a norm. However, to reduce this passage in Deuteronomy to
a prohibition against women wearing jeans, as many of the early Pentecostals
did, is not only a stretch (no pun intended), but probably ludicrous. After
all, what is good for the goose is good for the gander, and in those days
men wore dresses (well, robes, actually, but you get the idea--they
certainly didn't wear trousers).