Transamerica (2005)

Desperate Housewives standout Felicity Huffman stars as Bree Osbourne, a male-to-female transsexual who learns on the eve before going under the knife to complete her transformation that she sired a son years earlier.  Forced by her analyst (Elizabeth Pena), who forbids her surgery to take place before confronting the issue, Bree embarks on a cross-country road trip to meet her son Toby (Kevin Zegers) in Transamerica (2005). Regardless of your gender, you’ll be happy she did too, because Mr. Zeger’s pleasure pegger is on full view. And if that’s not enough to satiate your carnal desires, Grant Monohon plays a hitchhiker who has zero qualms with flashing his own gorgeous goodies.